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Thomas M. Klapötke
Chemistry of High-Energy Materials
Also of interest
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ISSN 0334-6455, e-ISSN 2191-0324
Thomas M. Klapötke

Chemistry of High-
Energy Materials

5th Edition
Author
Prof. Dr. Thomas M. Klapötke
Ludwig-Maximilians University Munich
Department of Chemistry
Butenandtstr. 5–13 (Building D)
81377 Munich, Germany
[email protected]

ISBN 978-3-11-062438-0
e-ISBN (PDF) 978-3-11-062457-1
e-ISBN (EPUB) 978-3-11-062469-4

Library of Congress Control Number: 2019946369

Bibliographic information published by the Deutsche Nationalbibliothek

The Deutsche Nationalbibliothek lists this publication in the Deutsche Nationalbibliografie; detailed
bibliographic data are available on the Internet at http://dnb.dnb.de.

© 2019 Walter de Gruyter GmbH, Berlin/Boston

Typesetting: Meta Systems Publishing & Printservices GmbH, Wustermark
Printing and binding: CPI books GmbH, Leck
Cover image: antorti / E+ / Getty Images

www.degruyter.com
“We will not waver; we will not tire; we will not falter;
And we will not fail. Peace and freedom will prevail.”

G. W. Bush,
Presidential Address to the Nation,
October 7 th 2001
Preface to this 5th English edition
Everything which has been said in the preface to the first German, as well as in
the first to fourth English editions still holds true, and essentially does not need
any addition or correction. In this revised fifth edition in English, the manuscript
has been updated and various recent aspects of energetic materials have been
added:
(i) Some errors which were unfortunately present in the fourth edition have been
corrected and the references have also been updated where appropriate.
(ii) Chapters on the critical diameter, colored smokes, delay compositions, sensi-
tivities, gun erosion, TKX-50, liners, thermobaric weapons and nitrocellulose
have been updated.
(iii) Four new chapters on Aging (6.7), Air Bags (13.6), Spent Acid (10.4) and Toxici-
ty Measurements (13.7) have been added.

In addition to the people thanked in the German and first four English editions,
the author would like to thank Dr. Manfred Bohn (ICT), Dr. Johann Glück (ZF), Dr.
Paul Wanninger (PWX), Mr. Moritz Mühlemann (BIAZZI), Mr. Marcel Holler (Bayern
Chemie), Ms. Cornelia Unger (LMU) and Ms. Teresa Küblböck (LMU) for many in-
spired discussions.

Munich, July 2019 Thomas M. Klapötke

https://doi.org/10.1515/9783110624571-203
Preface to the 4th English edition
Everything which has been said in the preface to the first German, as well as in
the first to third English editions, still holds and essentially does not need any
addition or correction. In this revised fourth edition in English, the manuscript has
been updated and various recent aspects of energetic materials have been added:
(i) Some errors, which were unfortunately present in the third edition, have been
corrected, and the references have also been updated where appropriate.
(ii) The chapters on shaped charges, visible pyrotechnics, smokes (addition of
P3N5 ), primary explosives (MTX-1), composite and double-base propellants,
and Gurney energy have been updated.
(iii) Four new chapters on Electric Detonators (5.4), Detonation velocity from Laser
Induced Air Shock (9.7), Thermally Stable Explosives (9.8), and Explosive
Welding (13.5) have been added.

In addition to the people thanked in the German and first three English editions,
the author would like to thank Professor Dr. Mohammad H. Keshavarz, Dr. Tomasz
Witkowski, Col. Dr. Ahmed Elbeih, Cpt. Mohamed Abd-Elghany, M.Sc. and Lt. An-
dreea Voicu, M.Sc. for many inspired discussions.

Munich, July 2017 Thomas M. Klapötke

https://doi.org/10.1515/9783110624571-204
Preface to the 3rd English edition
Everything which has been said in the preface to the first German and first and
second English editions still holds and essentially does not need any addition or
correction. In this revised third edition in English the manuscript has been up-
dated and various recent aspects of energetic materials have been added:
(i) some errors which unfortunately occurred in the first and second editions have
been corrected and the references have also been updated where appropriate.
(ii) The chapters on critical diameters, delay compositions, visible light (blue)
pyrotechnics, polymer-bonded explosives (PBX), HNS, thermodynamic calcula-
tions, DNAN, smoke (yellow) formulations and high-nitrogen compounds have
been updated.
(iii) Five new short chapters on Ignition and Initiation (chapters 5.2 and 5.3), the
Plate Dent Test (chapter 7.4), Underwater Explosions (chapter 7.5) and the
Trauzl Test (chapter 6.6) have been added.

In addition to the people thanked in the German and first and second English
editions, the author would like to thank Dr. Vladimir Golubev and Tomasz Witkow-
ski (both LMU) for many inspired discussions concerning hydrocode calculations.
The author is also indebted to and thanks Dr. Manuel Joas (DynITEC, Troisdorf,
Germany) for his help with the preparation of chapters 5.2 and 5.3.

Munich, October 2015 Thomas M. Klapötke

https://doi.org/10.1515/9783110624571-205
Preface to the 2nd English edition
Everything said in the preface to the first German and first English editions still
holds and essentially does not need any addition or correction. In this revised sec-
ond edition in English we have up-dated the manuscript and added some recent
aspects of energetic materials:
(i) We have tried to correct some mistakes which can not be avoided in a first
edition and also updated the references where appropriate.
(ii) The chapters on Ionic Liquids, Primary Explosives, NIR formulations, Smoke
Compositions and High-Nitrogen Compounds were updated.
(iii) Two new short chapters on Co-Crystallization (9.5) and Future Energetic Materi-
als (9.6) have been added.

In addition to the people thanked in the German and first English edition, the
author would like to thank Dr. Jesse Sabatini and Dr. Karl Oyler (ARDEC, Picatinny
Arsenal, NJ) for many inspired discussions concerning pyrotechnics.

Munich, May 2012 Thomas M. Klapötke

https://doi.org/10.1515/9783110624571-206
Preface to the first English edition
Everything said in the preface to the first German edition remains valid and essen-
tially does not need any addition or correction. There are several reasons for trans-
lating this book into English:
– The corresponding lecture series at LMU is now given in English in the post-
graduate M.Sc. classes, to account for the growing number of foreign students
and also to familiarize German students with the English technical terms.
– To make the book available to a larger readership world-wide.
– To provide a basis for the authorʼs lecture series at the University of Maryland,
College Park.

We have tried to correct some omissions and errors which can not be avoided in a
first edition and have also updated the references where appropriate. In addition,
five new chapters on Combustion (Ch. 1.4), NIR formulations (Ch. 2.5.5), the Gurney
Model (Ch. 7.3), dinitroguanidine chemistry (Ch. 9.4) and nanothermites (Ch. 13.3)
have been included in the English edition. The chapter on calculated combustion
parameters (Ch. 4.2.3) has been extended.
In addition to the people thanked in the German edition, the author would like
to thank Dr. Ernst-Christian Koch (NATO, MSIAC, Brussels) for pointing out various
mistakes and inconsistencies in the first German edition. For inspired discussions
concerning the Gurney model special thanks goes to Joe Backofen (BRIGS Co., Oak
Hill). Dr. Anthony Bellamy, Dr. Michael Cartwright (Cranfield University), Neha
Mehta, Dr. Reddy Damavarapu and Gary Chen (ARDEC) and Dr. Jörg Stierstorfer
(LMU) are thanked for ongoing discussions concerning secondary and primary ex-
plosives.
The author also thanks Mr. Davin Piercey, B.Sc. for corrections and for writing
the new chapter on nanothermites, Dr. Christiane Rotter for her help preparing the
English figures and Dr. Xaver Steemann for his help with the chapter on detonation
theory and the new combustion chapter. The author thanks the staff of de Gruyter
for the good collaboration preparing the final manuscript.

Munich, January 2011 Thomas M. Klapötke

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Preface to the first German edition
This book is based on a lecture course which has been given by the author for
more than 10 years at the Ludwig-Maximilian University Munich (LMU) in the post-
graduate Master lecture series, to introduce the reader to the chemistry of highly
energetic materials. This book also reflects the research interests of the author. It
was decided to entitle the book “Chemistry of High-Energy Materials” and not sim-
ply “Chemistry of Explosives” because we also wanted to include pyrotechnics,
propellant charges and rocket propellants into the discussion. On purpose we do
not give a comprehensive historical overview and we also refrained from extensive
mathematical deductions. Instead we want to focus on the basics of chemical ex-
plosives and we want to provide an overview of recent developments in the re-
search of energetic materials.
This book is concerned with both the civil applications of high-energy materi-
als (e.g. propellants for carrier or satellite launch rockets and satellite propulsion
systems) as well as the many military aspects. In the latter area there have been
many challenges for energetic materials scientists in recent days some of which
are listed below:
– In contrast to classical targets, in the on-going global war on terror (GWT), new
targets such as tunnels, caves and remote desert or mountain areas have be-
come important.
– The efficient and immediate response to time critical targets (targets that move)
has become increasingly important for an effective defense strategy.
– Particularly important is the increased precision (“we want to hit and not to
miss the target”, Adam Cumming, DSTL, Sevenoaks, U.K.), in order to avoid
collateral damage as much as possible. In this context, an effective coupling
with the target is essential. This is particularly important since some evil re-
gimes often purposely co-localize military targets with civilian centers (e.g. mil-
itary bases near hospitals or settlements).
– The interest in insensitive munitions (IM) is still one of the biggest and most
important challenges in the research of new highly energetic materials.
– The large area of increasing the survivability (for example by introducing
smokeless propellants and propellant charges, reduced signatures of rocket
motors and last but not least, by increasing the energy density) is another vast
area of huge challenge for modern synthetic chemistry.
– Last but not least, ecological aspects have become more and more important.
For example, on-going research is trying to find suitable lead-free primary ex-
plosives in order to replace lead azide and lead styphnate in primary composi-
tions. Moreover, RDX shows significant eco- and human-toxicity and research
is underway to find suitable alternatives for this widely used high explosive.
Finally, in the area of rocket propulsion and pyrotechnical compositions, re-
placements for toxic ammonium perchlorate (replaces iodide in the thyroid

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 Preface to the first German edition xiii

gland) which is currently used as an oxidizer are urgently needed. Despite all
this, the performance and sensitivity of a high-energy material are almost al-
ways the key-factors that determine the application of such materials – and
exactly this makes research in this area a great challenge for synthetically ori-
ented chemists.

The most important aspect of this book and the corresponding lecture series at
LMU Munich, is to prevent and stop the already on-going loss of experience, knowl-
edge and know-how in the area of the synthesis and safe handling of highly ener-
getic compounds. There is an on-going demand in society for safe and reliable
propellants, propellant charges, pyrotechnics and explosives in both the military
and civilian sector. And there is no one better suited to provide this expertise than
well trained and educated preparative chemists.
Last but not least, the author wants to thank those who have helped to make
this book project a success. For many inspired discussions and suggestions the
authors wants to thank the following colleagues and friends: Dr. Betsy M. Rice, Dr.
Brad Forch and Dr. Ed Byrd (US Army Research Laboratory, Aberdeen, MD), Prof.
Dr. Manfred Held (EADS, TDW, Schrobenhausen), Dr. Ernst-Christian Koch (NATO
MSIAC, Brussels), Dr. Miloslav Krupka (OZM, Czech Republic), Dr. Muhamed Suces-
ca (Brodarski Institute, Zagreb, Croatia), Prof. Dr. Konstantin Karaghiosoff (LMU
Munich), Prof. Dr. Jürgen Evers (LMU Munich), as well as many of the past and
present co-workers of the authors research group in Munich without their help this
project could not have been completed.
The author is also indebted to and thanks Dipl.-Chem. Norbert Mayr (LMU Mu-
nich) for his support with many hard- and soft-ware problems, Ms. Carmen Nowak
and Ms. Irene S. Scheckenbach (LMU Munich) for generating many figures and for
reading a difficult manuscript. The author particularly wants to thank Dr. Stephanie
Dawson (de Gruyter) for the excellent and efficient collaboration.

Munich, July 2009 Thomas M. Klapötke

Contents

Preface to this 5th English edition vii

Preface to the 4th English edition viii

Preface to the 3rd English edition ix

Preface to the 2nd English edition x

Preface to the first English edition xi

Preface to the first German edition xii

1 Introduction 1
1.1 Historical Overview 1
1.2 New Developments 11
1.2.1 Polymer-Bonded Explosives 11
1.2.2 New High (Secondary) Explosives 15
1.2.3 New Primary Explosives 25
1.2.4 New Oxidizers for Solid Rocket Motors 35
1.2.5 Initial Characterization of New Energetic Materials 41
1.3 Definitions 42
1.4 Combustion, Deflagration, Detonation – A Short Introduction 49
1.4.1 Fire and Combustion 49
1.4.2 Deflagration and Detonation 51

2 Classification of Energetic Materials 55

2.1 Primary Explosives 55
2.2 High (Secondary) Explosives 60
2.3 Propellant Charges 69
2.4 Rocket Propellants 72
2.4.1 Chemical Thermal Propulsion (CTP) 89
2.5 Pyrotechnics 91
2.5.1 Detonators, Initiators, Delay Compositions and Heat-Generating
Pyrotechnics 91
2.5.2 Light-Generating Pyrotechnics 95
2.5.3 Decoy Flares 104
2.5.4 Smoke Munitions 111
2.5.5 Near-Infrared (NIR) Compositions 122
xvi Contents

3 Detonation, Detonation Velocity and Detonation Pressure 125

4 Thermodynamics 137
4.1 Theoretical Basis 137
4.2 Computational Methods 143
4.2.1 Thermodynamics 143
4.2.2 Detonation Parameters 147
4.2.3 Combustion Parameters 151
4.2.4 Example: Theoretical Evaluation of New Solid Rocket
Propellants 160
4.2.5 Example: EXPLO5 Calculation of the Gun Propellant Properties of
Single, Double and Triple Base Propellants 167
4.2.6 Semiempirical Calculations (EMDB) 169

5 Initiation 173
5.1 Introduction 173
5.2 Ignition and Initiation of Energetic Materials 175
5.3 Laser Ignition and Initiation 177
5.4 Electric Detonators 183

6 Experimental Characterization of Explosives 187

6.1 Sensitivities 187
6.2 Long-Term Stabilities 214
6.3 Insensitive Munitions 216
6.4 Gap Test 217
6.5 Classification 218
6.6 Trauzl Test 220
6.7 Aging of Energetic Materials 223

7 Special Aspects of Explosives 235

7.1 Shaped Charges 235
7.2 Detonation Velocities 244
7.3 Gurney Model 250
7.3.1 Example: Calculation of the Gurney Velocity for a General Purpose
Bomb 255
7.4 Plate Dent Tests vs. Fragment Velocities 256
7.5 Underwater explosions 262

8 Correlation between the Electrostatic Potential and the Impact

Sensitivity 269
8.1 Electrostatic Potentials 269
8.2 Volume-Based Sensitivities 272
 Contents xvii

9 Design of Novel Energetic Materials 275

9.1 Classification 275
9.2 Polynitrogen Compounds 277
9.3 High-Nitrogen Compounds 283
9.3.1 Tetrazole and Dinitramide Chemistry 284
9.3.2 Tetrazole, Tetrazine and Trinitroethyl Chemistry 291
9.3.3 Ionic Liquids 296
9.4 Dinitroguanidine Derivatives 300
9.5 Co-Crystallization 302
9.6 Future Energetics 303
9.7 Detonation Velocities from Laser-induced Air Shock 317
9.8 Thermally Stable Explosives 323

10 Synthesis of Energetic Materials 331

10.1 Molecular Building Blocks 331
10.2 Nitration Reactions 332
10.3 Processing 337
10.4 Safe Handling of Spent Acid 338

11 Safe Handling of Energetic Materials in the Laboratory 343

11.1 General 343
11.2 Protective Equipment 344
11.3 Laboratory Equipment 347

12 Energetic Materials of the Future 349

13 Related Topics 357

13.1 Thermobaric Weapons 357
13.2 Agent Defeat Weapons 360
13.3 Nanothermites 362
13.3.1 Example: Iron Oxide / Aluminum Thermite 369
13.3.2 Example: Copper Oxide / Aluminum Thermite 370
13.3.3 Example: Molybdenum Trioxide / Aluminum Thermite 371
13.4 Homemade Explosives 371
13.5 Explosive Welding 372
13.6 Gas Generators (Air Bags) 373
13.7 Toxicity Measurements 376

14 Study Questions 381

15 Literature 385
xviii Contents

16 Appendix 397
Important reaction types in organic nitrogen chemistry 397
Curing of a diol (HTPB) with isocyanate binder 401
Important reaction types in inorganic nitrogen chemistry 401
Collection of formulas 411

Author 417

Index 419
1 Introduction

1.1 Historical Overview

In this chapter we do not want to be exhaustive in scope, but rather to focus on

some of the most important milestones in the chemistry of explosives (Tab. 1.1).
The development of energetic materials began with the accidental discovery of
blackpowder in China (∼ 220 BC). In Europe this important discovery remained
dormant until the 13 th and 14 th centuries, when the English monk Roger Bacon
(1249) and the German monk Berthold Schwarz (1320) started to research the prop-
erties of blackpowder. At the end of the 13th century, blackpowder was finally intro-
duced into the military world. However, it was not until 1425 that Corning greatly
improved the production methods and blackpowder (or gunpowder) was then in-
troduced as a propellant charge for smaller and later also for large calibre guns.
Even today, ca. 100,000 pounds of blackpowder are still used in the US military
per year.
One application in which BP is still in use is in “time blasting fuses”. They were
invented as early as 1831, and contain approx. 4.7 g/m BP in the core (see Fig. 1.1a).
The burn rate is about 135 m/s, and since they are RF safe (radio frequency), they
are very popular with the military.

Fig. 1.1a: Time Blasting Fuse.

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2 1 Introduction

Tab. 1.1: Historical overview of some important secondary explosives.

substance acronym development application density/g cm–3 explosive

power b

blackpowder BP 1250–1320 1425–1900 ca. 1.0

nitroglycerine NG 1863 in propellant 1.60 170
charges
dynamite Dy 1867 civil/commer- varies varies
cial only
picric acid PA 1885–1888 WW I 1.77 100
nitroguanidine NQ 1877 most in TLPs 1.71 99
trinitrotoluene TNT 1880 WW I 1.64 116
nitropenta PETN 1894 WW II 1.77 167
hexogen RDX 1920–1940 WW II 1.81 169
octogen HMX 1943 WW II 1.91 169
(β polymorph)
hexanitrostilbene HNS 1913 1966 1.74
triaminotrinitro- TATB 1888 1978 1.93
benzene
HNIW CL-20 1987 under evaluation 2.1
(ε polymorph)
a
rel. to PA

The next milestone was the first small-scale synthesis of nitroglycerine (NG) by
the Italian chemist Ascanio Sobrero (1846). Later, in 1863 Imanuel Nobel and his
son Alfred commercialized NG production in a small factory near Stockholm
(Tab. 1.1). NG is produced by running highly concentrated, almost anhydrous, and
nearly chemically pure glycerine into a highly concentrated mixture of nitric and
sulfuric acids (HNO3 / H 2SO4 ), while cooling and stirring the mixture efficiently. At
the end of the reaction, the nitroglycerine and acid mixture is transferred into a
separator, where the NG is separated by gravity. Afterwards, washing processes
using water and alkaline soda solution remove any residual acid.
Nitroglycerin (NG) showed itself to be extremely dangerous for blasting. Alfred
Nobel scrambled to find a solution, and in doing so, invented dynamite. His solu-
tion was to solidify the NG by adding diatomaceous earth (mineral powder). It was
not understood why this worked. It is now known that liquid HEs are sensitized
by cavitation bubble collapse. Liquid HEs are dangerous, because they are often
insensitive in pure form, but highly sensitized by aeration.
Initially NG was very difficult to handle because of its high impact sensitivity
and unreliable initation by blackpowder. Among many other accidents, one explo-
sion in 1864 destroyed the Nobel factory completely, killing Alfred’s brother Emil.
In the same year, Alfred Nobel invented the metal blasting cap detonator, and
replaced blackpowder with mercury fulminate (MF), Hg (CNO)2 . Although the
Swedish-German Scientist Johann Kunkel von Löwenstern had described Hg (CNO)2
 1.1 Historical Overview 3

C
N
O O
N
C Hg

Fig. 1.1b: Molecular structure of mercury fulminate, Hg (CNO)2.

H CH2ONO2 H ONO2
H C O NO2 H C O
O
C C H
H ONO2 H
H C O NO2 C C C C
ONO2 H H
O O
H C O NO2 C C H H C O
H H ONO2 CH2ONO2 n

NG NC

Fig. 1.2: Molecular structures of nitroglycerine (NG) and nitrocellulose (NC).

as far back as in the 17th century, it did not have any practical application prior to
Alfred Nobel’s blasting caps. It is interesting to mention that it was not until the
year 2007 that the molecular structure of Hg (CNO)2 was elucidated by the LMU
research team (Fig. 1.1b) [1, 2]. Literature also reports the thermal transformation
of MF, which, according to the below equation, forms a new mercury containing
explosive product which is reported to be stable up to 120 °C.

3 Hg (CNO)2 → Hg3(C2N2O2 )3

After another devastating explosion in 1866 which completely destroyed the NG

factory, Alfred Nobel focused on the safe handling of NG explosives. In order to
reduce the sensitivity, Nobel mixed NG (75 %) with an absorbent clay called “Kie-
selguhr” (25 %). This mixture called “Guhr Dynamite” was patented in 1867. Despite
the great success of dynamite in the civil sector, this formulation has never found
significant application or use in the military sector.
One of the great advantages of NG (Fig. 1.2) in comparison to blackpowder
(75 % KNO3 , 10 % S8 , 15 % charcoal) is that it contains both the fuel and oxidizer
in the same molecule which guarantees optimal contact between both components,
whereas in blackpowder, the oxidizer (KNO3 ) and the fuel (S8 , charcoal) have to
be physically mixed.
At the same time as NG was being researched and formulated several other
research groups (Schönbein, Basel and Böttger, Frankfurt-am-Main) worked on the
nitration of cellulose to produce nitrocellulose (NC). In 1875 Alfred Nobel discov-
ered that when NC is formulated with NG, they form a gel. This gel was further
refined to produce blasting gelatine, gelatine dynamite and later in 1888 ballistite
(49 % NC, 49 % NG, 2 % benzene and camphor), which was the first smokeless
powder. (Cordite which was developed in 1889 in Britain, had a very similar com-
4 1 Introduction

position.) In 1867 it was proven that mixtures of NG or dynamite and ammonium

nitrate (AN) showed enhanced performance. Such mixtures were used in the civil
sector. In 1950 manufacturers started to develop explosives which were waterproof
and solely contained the less hazardous AN. The most prominent formulation was
ANFO (Ammonium Nitrate Fuel Oil) which found extensive use in commercial
areas (mining, quarries etc.). Since the 1970s aluminium and monomethylamine
were added to such formulations to produce gelled explosives which could deto-
nate more easily. More recent developments include production of emulsion explo-
sives which contain suspended droplets of a solution of AN in oil. Such emulsions
are water proof, yet readily detonate because the AN and oil are in direct contact.
Generally, emulsion explosives are safer than dynamite and are simple and cheap
to produce.
Picric acid (PA) was first reported in 1742 by Glauber, however it was not used
as an explosive until the late 19th century (1885–1888), when it replaced blackpow-
der in nearly all military operations world-wide (Fig. 1.3). PA is prepared best by
dissolving phenol in sulfuric acid and the subsequent nitration of the resulting of
phenol-2,4-disulfonic acid with nitric acid. The direct nitration of phenol with nitric
acid is not possible because the oxidizing HNO3 decomposes the phenol molecule.
Since the sulfonation is reversible, the —SO3 H groups can then be replaced with
—NO2 groups by refluxing the disulfonic acid in concentrated nitric acid. In this
step the third nitro group is introduced as well. Although pure PA can be handled
safely, a disadvantage of PA is its tendency to form impact sensitive metal salts
(picrates, primary explosives) when in direct contact with shell walls. PA was used
as a grenade and as mine filling.
Tetryl was developed at the end of the 19th century (Fig. 1.3) and represents
the first explosive of the nitroamino (short: nitramino) type. Tetryl is best obtained
by dissolving monomethylaniline in sulfuric acid and then pouring the solution
into nitric acid, while cooling the process.
The above mentioned disadvantages of PA are overcome by the introduction of
trinitrotoluene (TNT). Pure 2,4,6-TNT was first prepared by Hepp (Fig. 1.3) and its
structure was determined by Claus and Becker in 1883. In the early 20th century
TNT almost completely replaced PA and became the standard explosive during
WW I. TNT is produced by the nitration of toluene with mixed nitric and sulfuric
acid. For military purposes TNT must be free of any isomer other than the 2,4,6-
isomer. This is achieved by recrystallization from organic solvents or from 62 %
nitric acid. TNT is still one of the most important explosives for blasting charges
today. Charges are produced through casting and pressing. However, cast charges
of TNT often show sensitivity issues and do not comply with the modern insensitive
munition requirements (IM). For this reason alternatives to TNT have been suggest-
ed. One of these replacements for TNT is NTO (filler) combined with 2,4-dinitroani-
sole (DNAN, binder).
Nitroguanidine (NQ) was first prepared by Jousselin in 1887 (Fig. 1.3). How-
ever, during WW I and WW II it only found limited use, for example in formulations
 1.1 Historical Overview 5

H3C NO2
OH N CH3
O2N NO2 O2N NO2 O2N NO2

NO2 NO2 NO2

PA Tetryl TNT

NH2 O2N O H2C CH2 O NO2

H2N C C
N NO2 O2N O H2C CH2 O NO2

NQ PETN

O2N
H2
NO2 N C NO2
N H2C N
H2C CH2
N CH2
N N O2N C N
O2N C NO2 H2
H2 NO2

RDX HMX

NO2 O2N NO2

H2N NH2
H
O2N C C NO2
H
O2N NO2
NO2 O2N NH2

HNS TATB

Fig. 1.3: Molecular structures of picric acid (PA), tetryl, trinitrotoluene (TNT), Nitroguanidine (NQ),
pentaerythritol tetranitrate (PETN), hexogen (RDX), octogen (HMX), hexanitrostilbene (HNS) and
triaminotrinitrobenzene (TATB).

with AN in grenades for mortars. In more recent days NQ has been used as a com-
ponent in triple-base propellants together with NC and NG. One advantage of the
triple-base propellants is that unlike double-base propellants the muzzle flash is
reduced. The introduction of about 50 % of NQ to a propellant composition also
results in a reduction of the combustion temperature and consequently reduced
erosion and increased lifetime of the gun. NQ can be prepared from dicyandiamide
and ammonium nitrate via guanidinium nitrate which is dehydrated with sulfuric
acid under the formation of NQ:
6 1 Introduction

H2N N NH4NO3 H2SO4 NH2

C C C(NH2)3 NO3 H2N C
H2N N H2N CN H2O N NO2

The most widely used explosives in WW II other than TNT were hexogen (RDX)
and pentaerythritol tetranitrate (nitropenta, PETN) (Fig. 1.3). Since PETN is more
sensitive and chemically less stable than RDX, RDX was (and is) the most common-
ly used high explosive. PETN is a powerful high explosive and has a great shatter-
ing effect (brisance). It is used in grenades, blasting caps, detonation cords and
boosters. PETN is not used in its pure form because it is too sensitive. A formulation
of 50 % TNT and 50 % PETN is known as “pentolite”. In combination with plasti-
cized nitrocellulose PETN is used to form polymer bonded explosives (PBX). The
military application of PETN has largely been replaced by RDX. PETN is prepared
by introducing pentaerythritol into concentrated nitric acid while cooling and stir-
ring the mixture efficiently. The then formed bulk of PETN crystallizes out of the
acid solution. The solution is then diluted to about 70 % HNO3 in order to precipi-
tate the remaining product. The washed crude product is purified by recrystalliza-
tion from acetone.
Hexogen (RDX) was first prepared in 1899 by Henning for medicinal use. (N.B.
NG and PETN are also used in medicine to treat angina pectoris. The principal
action of these nitrate esters is vasodilation (i.e. widening of the blood vessels).
This effect arises because in the body the nitrate esters are converted to nitric oxide
(NO) by mitochondrial aldehyde dehydrogenase, and nitric oxide is a natural va-
sodilator.) In 1920 Herz prepared RDX for the first time by the direct nitration of
hexamethylene tetramine. Shortly afterwards Hale (Picatinny Arsenal, NJ) devel-
oped a process that formed RDX in 68 % yield. The two processes most widely used
in WW II were
1. the Bachmann process (KA process) in which hexamethylene tetramine dini-
trate reacts with AN and a small amount of nitric acid in an acetic anhydride
medium to form RDX (type B RDX). The yields are high, however, 8–12 % of
HMX form as a side product.
2. the Brockman process (type A RDX) essentially produces pure RDX.

After WW II octogen (HMX) started to become available. Until today, most high
explosive compositions for military use are based on TNT, RDX and HMX (Tab. 1.2).
Since 1966 hexanitrostilbene (HNS) and since 1978 triaminotrinitrobenzene
(TATB) are produced commercially (Fig. 1.3). Both secondary explosives show ex-
cellent thermal stabilities and are therefore of great interest for the NAVY (fuel
fires) and for hot deep oil drilling applications (Fig. 1.3). Especially HNS is known
as a heat- and radiation-resistant explosive which is used in heat-resistant explo-
sives in the oil industry. The brisance of HNS is lower than that of RDX, but the
melting point of approx. 320 °C is much higher. HNS can directly be prepared from
 1.1 Historical Overview 7

Tab. 1.2: Composition of some high explosive formulations.

name composition

Composition A 88.3 % RDX, 11.7 % non-energetic plasticizers

Composition B 60 % RDX, 39 % TNT, 1 % binder (wax)
Composition C4 90 % RDX, 10 % polyisobutylene
octol 75 % HMX, 25 % RDX
torpex a 42 % RDX, 40 % TNT, 18 % aluminum
PBXN-109 64 % RDX, 20 % aluminum, 16 % binder and plasticizer
OKFOL 96.5 % HMX, 3.5 % wax
a
An Australian improved development of torpex is known under the name H6 and also contains hex-
ogen (RDX), trinitrotoluene (TNT) and aluminum. H6 was used as a high explosive formulation in the
MOAB bomb (Massive Ordnance Air Blast bomb). MOAB (also known as GBU-43/B) is with a load of
approx. 9500 kg high explosive formulation (30 % TNT, 45 % RDX, 20 % AL, 5 % wax) one of the largest
conventional bombs ever used.

Tab. 1.2a: Desired properties of potential HNS replacements

Thermal Stability No changes after 100 h at 260 °C

Detonation Velocity > 7500 m/s
Specific Energy * > 975 kJ/kg
Impact Sensitivity > 7.4 J
Friction Sensitivity > 235 N
Total Costs < 500 Euro/kg
Critical diameter ≥ HNS

* specific energy. F = pe · V = n · R · T

trinitrotoluene through oxidation with sodium hypochlorite in a methanol/THF so-

lution:

2 C6 H 2(NO2 )3CH 3 + 2 NaOCl → C6 H 2(NO2 )3—CH═CH—C6 H 2(NO2 )3 + 2 H 2O + 2 NaCl

Since oil deposits which are located closer to the surface are becoming rare, deeper
oil reserves now have to be explored where (unfortunately) higher temperatures
are involved. Therefore, there is an ongoing search for explosives which are even
more thermally stable (decomposition temperatures > 320 °C) than HNS, but at the
same time show better performance (Tab. 1.2a). Higher thermal stabilities usually
result in compounds with lower sensitivities which are therefore safer to handle.
According to J. P. Agrawal, new energetic materials with high thermal stabili-
ties can be achieved by incorporating the following points in the compounds:
– Salt formation
– Introduction of amino groups
– Introduction of conjugation
– Condensation with a triazole ring.
8 1 Introduction

O2N

NO2

O2N HN

O2N
N
O2N
O2N NO2
N
HN
O2N HN

N N
H NO2
NO2 O2N
3-picrylamino-1,2,4-triazole (PATO) 2,6-Bis(picrylamino)-3,5-dinitro-pyridine (PYX)
m.p. 310 ºC m.p. 360 ºC

Fig. 1.3a: Molecular structures of PATO and PYX.

OH O Cl

O2N NO2 O2N NO2 O 2N NO2

Pyridine POCl3

NO2 NO2 NO2

N
H

NaF
N
H2N NH2
O 2N NO2
NO2 NO2 NO2 NO2
HNO3
HN N NH HN N NH

O 2N NO2 O2N NO2 O2N NO2 O2N NO2

Fig. 1.3b: Synthetic route for PYX.

Two possible replacements for HNS which are presently under investigation are
PYX and PATO.
Various picryl and picrylamino substituted 1,2,4–triazoles which were formed
by condensing 1,2,4-triazole or amino-1,2,4-triazole with picryl chloride (1-chloro-
2,4,6-trinitrobenzene) were studied in detail by Coburn & Jackson. One of these
molecules is PATO (3-picrylamino-1,2,4-triazole), a well known, thermally stable
explosive, which is obtained by the condensation of picryl chloride with 3-amino-
1,2,4-triazole (Fig. 1.3a). Another promising candidate for a high-temperature ex-
plosive is PYX (Fig. 1.3a). The synthesis for PYX is shown in Fig. 1.3b.
 1.1 Historical Overview 9

O2N NO2 O2N NO2

N N
N N N N
H N N H
N H H N
O2N NO2 O2N NO2

Fig. 1.3c: Molecular structure of BTDAONAB.

Tab. 1.2b: Comparative data of the thermal and explosive properties of TATB, HNS, BTDAONAB and
BeTDAONAB.

Property TATB HNS BTDAONAB BeTDAONAB

density / g/cc 1.94 1.74 1.97 1.98

Sensitivity to temperature / °C 360 318 350 260
DTA (exo) / °C 360 353 550 275
DSC (exo) / °C 371 350 268
ΩCO / % –18.6 –17.8 –6.8 –5.9
IS / J 50 5 21 21
FS / N > 353 240 353 362
VoD / m s–1 7900 7600 8600 8700
pC–J / kbar 273 244 341 354

Agrawal et al. reported the synthesis of BTDAONAB (Fig. 1.3c) which does not melt
below 550 °C and is considered to be a better and thermally more stable explosive
than TATB. According to the authors, this material has a very low impact (21 J), no
friction sensitivity (> 360 N) and is thermally stable up to 550 °C. These reported
properties makes BTDAONAB superior to all of the nitro-aromatic compounds
which have been discussed. BTDAONAB has a VoD of 8300 m/s while TATB is
about 8000 m/s [Agrawal et al., Ind. J. Eng. & Mater Sci., 2004, 11, 516–520; Agraw-
al et al., Central Europ. J. Energ. Mat. 2012, 9(3), 273–290.]
Moreover, recently another nitro-aromatic compound (BeTDAONAB), similar to
Agrawal’s BTDAONAB has been published by Keshavaraz et al., which is also very
insensitive (Fig 1.3d). In this compound, the terminal triazole moieties have been
replaced by two more energetic (more endothermic) tetrazole units [Keshavaraz et
al., Central Europ. J. Energ. Mat. 2013, 10(4), 455; Keshavaraz et al., Propellants,
Explos. Pyrotech., DOI: 10.1002/prep.201500017]. Table 1.2b shows a comparison of
the thermal and explosive properties of TATB, HNS, BTDAONAB and BeTDAONAB.
TATB is obtained from trichloro benzene by nitration followed by a reaction
of the formed trichlorotrinitro benzene with ammonia gas in benzene or xylene
solution.
As shown above, the number of chemical compounds which have been used for
high explosive formulations until after WW II is relatively small (Tab. 1.1 and 1.2). As
10 1 Introduction

COOH Nitration COOH NH2

92-95 ºC Oleum, NaN3
4h reflux, 4 h

O2N NO2 O2N NO2

Cl Cl Cl
4-Chlorobenzoic acid 4-Chloro-3,5-dinitrobenzoic acid 4-Chloro-3,5-dinitroaniline

Nitration
85-90 ºC
2.5 h

O2N NO2 O2N NO2

Cl N N Cl

O 2N NO2 O2N NO2

4,4'-Dichloro-2,2',3,3',5,5',6,6'-octanitroazobenzene (DCONAB)

5-Amino-1,2,3,4-tetrazole
Reflux, 5 h

O2N NO2 O2N NO2

N N N N
N N N N
N H H N
N N
H H
O2N NO2 O2N NO2

Fig. 1.3d: Synthetic route for the synthesis of BeTDAONAB.

we can also see from Table 1.1 and 1.2 the best performing high explosives (RDX and
HMX; TNT is only used because of its melt-cast applications) possess relatively high
densities and contain oxidizer (nitro and nitrato groups) and fuel (C—H back bone)
combined in one and the same molecule. One of the most powerful new high explo-
sive is CL-20 which was first synthesized in 1987 by the Naval Air Warfare Center
(NAWF) China Lake (Fig. 1.7, Tab. 1.1). CL-20 is a cage compound with significant
cage strain which also contains nitramine groups as oxidizers and possesses a densi-
ty of about 2 g cm–3. This already explains the better performance in comparison
with RDX and HMX. However, due to the relatively high sensitivity of the (desirable)
ε polymorph as well as possible phase transition problems and high production costs
(ca. $ 1,000/Lb; cf. RDX ca. $ 20.—/kg; GAP ca. $ 500/kg) so far CL-20’s wide and
general application has not been established.
 1.2 New Developments 11

1.2 New Developments

1.2.1 Polymer-Bonded Explosives

Since about 1950 polymer-bonded (or plastic-bonded) explosives (PBX) have been
developed in order to reduce sensivity and to facilitate safe and easy handling. PBX
also show improved processibility and mechanical properties. In such materials
the crystalline explosive is embedded in a rubber-like polymeric matrix. One of the
most prominent examples of a PBX is Semtex. Semtex was invented in 1966 by
Stanislav Brebera, a chemist who worked for VCHZ Synthesia in Semtin (hence the
name Semtex), a suburb of Pardubice in the Czech Republic. Semtex consists of
varying ratios of PETN and RDX. Usually polyisobutylene is used for the polymeric
matrix, and phthalic acid n-octylester is the plasticizer. Other polymer matrices
which have been introduced are polyurethane, polyvinyl alcohol, PTFE (teflon),
Viton, Kel-F, PBAN, HTPB and various polyesters. PBAN (polybutadiene acrylo-
nitrile) was used in the space shuttle composite propellant.
Often, however, problems can arise when combining the polar explosive (RDX)
with the non-polar polymeric binder (e.g. polybutadiene or polypropylene). In or-
der to overcome such problems, additives are used to facilitate mixing and intermo-
lecular interactions. One of such polar additives is dantacol (DHE) (Fig. 1.4).

HO N N OH

Fig. 1.4: Structure of Dantacol (DHE).

One disadvantage of the polymer-bonded explosives of the first generation, is that

the non-energetic binder (polymer) and plasticizer lessened the performance. To
overcome this problem energetic binders and plasticizers have been developed.
The most prominent examples for energetic binders are (Fig. 1.5, a):
– poly-GLYN, poly(glycidyl)nitrate
– poly-NIMMO, poly(3-nitratomethyl-3-methyl-oxetane)
– GAP, glycidylazide polymer
– poly-AMMO, poly(3-azidomethyl-3-methyl-oxetane),
– poly-BAMO, poly(3,3-bis-azidomethyl-oxetane).

Examples for energetic plasticizers are (Fig. 1.5, b):

– NENA derivatives, alkylnitratoethylnitramine,
– EGDN, ethyleneglycoldinitrate,
12 1 Introduction

H2C O NO2 CH3 H2C N3

CH2 CH O O CH2 C CH2 CH2 C O

n H2C O NO2 n H n
poly-GLYN poly-NIMMO GAP

CH3 H2C N3
O CH2 C CH2 O CH2 C CH2
H2C N3 n H2C N3 n
(a) poly-AMMO poly-BAMO

NO2 H2C O NO2

R N CH2 CH2 O NO2 H3C C CH2 O NO2
H2C O NO2

NENA MTN

O NO2 H2C O NO2

O2N O CH2 CH CH2 CH2 O NO2 H2C O NO2

(b) BTTN EGDN

N
NH4NO3 R  Me (92 %)
R NH2  CH2O  NH3   Et (90 %)
N N R NO3 CH2CH2OH (82 %)
N

Ac2O / HNO3

R  Me (72 %) R
AcO N N N
Et (80 %)
CH2CH2ONO2 (76 %) NO2 NO2 NO2

HCl / CF3COOH

R  Me (85 %) R
Cl N N N
Et (85 %)
CH2CH2ONO2 (55 %) NO2 NO2 NO2

NaN3 /acetone

R  Me (78 %) R
N3 N N N
Et (88 %)
CH2CH2ONO2 (82 %) NO2 NO2 NO2

ONO2
N3 N N N

azide NO2 NO2 NO2 nitrato

nitramine
(c) ANTTO

Fig. 1.5: Energetic binders (a) and energetic plasticizers (b). Synthesis of the NENA compound,
ANTTO (c) (ANTTO = azido nitrato trinito triaza octane).
 1.2 New Developments 13

Fig. 1.5a: Ring-opening reactions (ROP) for the synthesis of energetic polymers.

– MTN, metrioltrinitrate,
– BTTN, butane-1,2,4-trioltrinitrate.

Fig. 1.5a shows a general synthesis route for various energetic polymers using the
ring-opening polymerization (ROP) strategy).
For binders in particular − but also for plasticizers − it is important to know
the glass transition temperature. The value of the glass transition temperature
should be as low as possible but at least −50 °C. If the temperature of a polymer
drops below Tg , it behaves in an increasingly brittle manner. As the temperature
rises above Tg , the polymer becomes more rubber-like. Therefore, knowledge of Tg
is essential in the selection of materials for various applications. In general, values
of Tg well below room temperature correspond to elastomers and values above
room temperature to rigid, structural polymers.
In a more quantitative approach for the characterization of the liquid-glass
transition phenomenon and Tg, it should be noted that in cooling an amorphous
material from the liquid state, there is no abrupt change in volume such as that
which occurs on cooling a crystalline material below its freezing point, Tf . Instead,
at the glass transition temperature, Tg, there is a change in the slope of the curve
of specific volume vs. temperature, moving from a low value in the glassy state to
14 1 Introduction

Liquid 2

Rubbery 1
Specific volume

state

Glassy state

Crystalline state

Temperature Tg Tf

Fig. 1.5b: Specific volume vs. temperature plot for a crystalline solid and a glassy material with a
glass transition temperature (Tg ).
Endotherm

Tg T

Fig. 1.5c: DSC plot illustrating the glass transition process for a glassy polymer which does not
crystallize and is being slowly heated from below Tg .

a higher value in the rubbery state over a range of temperatures. This comparison
between a crystalline material (1) and an amorphous material (2) is illustrated in
the figure below. Note that the intersection of the two straight line segments of
curve (2) defines the quantity Tg (Fig. 1.5b).
Differential scanning calorimetry (DSC) can be used to determine experimentally
the glass transition temperature. The glass transition process is illustrated in Fig. 1.5c
for a glassy polymer which does not crystallize and is being slowly heated from a
temperature below Tg . Here, the drop which is marked Tg at its midpoint, represents
the increase in energy which is supplied to the sample to maintain it at the same
temperature as the reference material. This is necessary due to the relatively rapid
 1.2 New Developments 15

increase in the heat capacity of the sample as its temperature is increases pass Tg .
The addition of heat energy corresponds to the endothermal direction.
The typical formulation of a cast polymer-bonded explosive is shown below
(reproduced with kind permission of Dr. Paul Wanninger):

percentage ingredient comment

85–90 % AP, RDX, HMX, Al

10–15 % HTPB, plasticizer HTPB is the binder
0.2 % Lecithin Lecithin is used to reduce the rheological yield point
0.2 % Antioxidants An antioxidant is added for long-life stability
10−3–10−4 % Catalyst The amount of catalyst determines the curing time
0.05–0.1 % bonding agent Different bonding agents for RDX, HMX and AP or Al are
recommended to improve the mechanical properties

Typical properties of melt cast, cast, and pressed PBX formulations are shown be-
low (reproduced with kind permission of Dr. Paul Wanninger):

melt cast PBX cast PBX pressed PBX

Ingredients TNT, RDX, HMX, NTO RDX, HMX + polymer RDX, HMX +
thermoplast
Technical process melting and casting mixing under HE + Binder + solvent,
vacuum and casting pressing at up to
under vacuum, 1500 bar
polymerization
Density (in % of TMD) 98 99.5 97−98
Density gradient high very low varies
Vulnerability high very low medium
Homogenicity low high medium

1.2.2 New High (Secondary) Explosives

New secondary explosives which are currently under research, development or

testing include 5-nitro-1,2,4-triazol-3-one (NTO), 1,3,3-trinitroazetidine (TNAZ), hexa-
nitrohexaazaisowurtzitane (HNIW, CL-20) and octanitrocubane (ONC) (Fig. 1.7). NTO
has already found application as a very insensitive compound in gas generators
for automobile inflatable air bags and in some polymer-bonded explosive formula-
tions. (N.B. Initially NaN3 was used in air bag systems, however, nowadays guani-
dinium nitrate is often used in combination with oxidizers such as AN in some
non-azide automotive inflators.) It is used to enhance burning at low flame temper-
atures. Low flame temperatures are desired in order to reduce the formation of NOx
16 1 Introduction

H OH H OSO2CH3
O C C
(CH3)3CNH2 CH3SO2Cl
H2C CH CH2Cl H2C CH2 H2C CH2
N EtN3 N
C(CH3)3 C(CH3)3

NaNO2

O2N NO2 O2N NO2 NaOH H NO2

C HNO3 C NaNO2 C
H2C CH2 H2C CH2 H2C CH2
N Ac2O N K3Fe(CN)6 N
NO2 C(CH3)3 C(CH3)3

Fig. 1.6: Synthesis of 1,3,3-trinitroazetidine (TNAZ).

gasses in inflators. NTO is usually produced in a two-step process from semicarba-

zide hydrochloride with formic acid via the intermediate formation of 1,2,4-triazol-
5-one (TO) and subsequent nitration with 70 % nitric acid:
H H NO2
O • HCl N N
HCOOH 70 % HNO3
H2N C O O
NH NH2 N N
N N
H H
TO NTO

Another interesting new and neutral high explosive is BiNTO, which can be synthe-
sized as shown in the below equation from commercially available NTO in a one-
step reaction.
O O O

NH N N
HN Paraformaldehyde HN NH
N N N
HCl
O2N O 2N NO2

BiNTO

TNAZ was first synthesized in 1983 and has a strained four-membered ring back-
bone with both C-nitro and nitramine (N—NO2 ) functionalities. There are various
routes that yield TNAZ all of which consist of several reaction steps. One possible
synthesis of TNAZ is shown in Figure 1.6. It starts from epichlorohydrine and tBu-
amine. As far as the author of this book is aware, there has been no wide-spread
use for TNAZ so far.
CL-20 (1987, A. Nielsen) and ONC (1997, Eaton) are without doubt the most
prominent recent explosives based on molecules with considerable cage-strain.
While CL-20 is now already produced in 100 kg quantities (e.g. by SNPE, France or
Thiokol, USA, ca. $ 1000.—/Lb) on industrial pilot scale plants, ONC is only avail-
able on a mg to g scale because of its very difficult synthesis. Despite the great
 1.2 New Developments 17

H NO2
O N
N
C H2C CH2
C NO2
N C
N O2N NO2
H

NTO TNAZ

O2N NO2 O2N NO2

O2N N N NO
2 O2N NO2
O O
N N O O
O2N NO2
N N NO2 O2N N N NO2
O2N
O2N NO2
CL-20 ONC TEX

Fig. 1.7: Molecular structures of 5-nitro-1,2,4-triazol-3-one (NTO), 1,3,3-trinitroazetidine (TNAZ),

hexanitrohexaazaisowurtzitane (CL-20), octanitrocubane (ONC) and 4,10-dinitro-2,6,8,12-tetraoxa-
4,10-diazaisowurtzitane (TEX).

[HCOOH] C6H5CH2N NCH2C6H5

6 C6H5CH2NH2  3 CHOCHO C6H5CH2N NCH2C6H5
CH3CN/ H2O
C6H5CH2N NCH2C6H5

H2 / Pd-C
Ac2O

O2NN NNO2 CH3CON NCOCH3

nitration
O2NN NNO2 CH3CON NCOCH3

O2NN NNO2 C6H5CH2N NCH2C6H5

Fig. 1.8: Synthesis of hexanitrohexaazaisowurtzitane (CL-20).

enthusiasm for CL-20 since its discovery over 20 years ago it has to be mentioned
that even today most of the high explosive formulations are based on RDX (see
Tab. 1.2). There are several reasons why CL-20 despite its great performance has
not yet been introduced successfully:
– CL-20 is much more expensive than the relatively cheap RDX.
– CL-20 has some sensitivity issues (see insentitive munitions).
– CL-20 exists in several polymorphic forms and the desired ε polymorph (be-
cause of its high density and detonation velocity) is thermodynamically not
the most stable one.

Interconversion of the ε form into a more stable but perhaps also more sensitive
other polymorph would result in a loss of performance and an increase in sentitivity.
CL-20 is obtained by the condension of glyoxal with benzylamine in an acid
catalyzed reaction to yield hexabenzylhexaazaisowurtzitane (Fig. 1.8). Afterwards
18 1 Introduction

H2N NO2
C C
H2N NO2

FOX-7

NH O • H SO NH O
2 4 NO2
• xH O
2 N H2SO4
O2N NO2 NH4 HN
H2N N NH2 H2O H2N N NH2
H H NO2
2
FOX-12
(a)

O O O O O O
H2N NH2
NaOMe HNO3
EtO OEt HN NH HN NH
MeOH H2SO4 aq NH3
H2N NH2 H3C OCH3 O2N NO2
O2N NO2
CH3

O2N NO2 O2N NO2

O O O O
HNO3 H2O
N NH HN NH H2N NH2
H2SO4 H
CO2
CH3
O2N NO2 O2N NO2

HO OH

N N NO2
HO OH
CH3
N N

(b) CH3

Fig. 1.9: Molecular structures of FOX-7 and FOX-12 (a). Two alternative synthetic routes for the syn-
thesis of FOX-7 (b).

the benzyl groups are replaced under reducing conditions (Pd-C catalyst) by easily
removable acetyl substituents. Nitration to form CL-20 takes place in the final reac-
tion step.
Another very insensitive high explosive which is structurally closely related to
CL-20 is 4,10-dinitro-2,6,8,12-tetraoxa-4,10-diazaisowurtzitane (TEX, see Fig. 1.7),
which was first described by Ramakrishnan and his co-workers in 1990. It displays
one of the highest densities of all nitramines (2.008 g cm–3 ) [1c].
 1.2 New Developments 19

Tab. 1.3: Characteristic performance and sensitivity data of FOX-7 and FOX-12 in comparison with
RDX.

FOX-7 FOX-12 RDX

detonation pressure, pC-J / kbar 340 260 347

detonation velocity, D / m s–1 8870 7900 8750

impact sensitivity / J 25 > 90 7.5

friction sensitivity / N > 350 > 352 120
ESD / J ca. 4.5 >3 0.2

60
heat flow, endothermic down (mW)

50

40

30

20

10 a-FOX-7 b-FOX-7 g-FOX-7

–10

100 150 200 250 300

temperature (°C)

Fig. 1.10: DSC-Plot of FOX-7.

The chemist N. Latypov of the Swedish defense agency FOI developed and synthe-
sized two other new energetic materials. These two compounds have become
known as FOX-7 and FOX-12 (Fig. 1.9, a). FOX-7 or DADNE (diamino dinitro ethene)
is the covalent molecule 1,1-diamino-2,2-dinitro ethene: (O2N)2C═C(NH 2 )2 . The syn-
thesis of FOX-7 always includes several reaction steps. Two alternative ways to pre-
pare FOX-7 are shown in Figure 1.9 (b). FOX-12 or GUDN (guanylurea dinitramide)
is the dinitramide of guanylurea: [H 2N—C(═NH 2 )—NH—C(O)—NH 2 ]+[N(NO2 )2 ]–.
It is interesting that FOX-7 has the same C/H/N/O ratio as RDX or HMX. Al-
though neither FOX-7 nor (and in particular not) FOX-12 meet RDX in terms of per-
formance (detonation velocity and detonation pressure). Both compounds are
much less sensitive than RDX and might be of interest due to their insensitive
munition (IM) properties. Table 1.3 shows the most characteristic performance and
sensitivity data of FOX-7 and FOX-12 in comparison with RDX.
FOX-7 exists in at least three different polymorphic forms (α, β and γ). The α
modification converts reversibly into the β form at 389 K (Fig. 1.10) [2]. At 435 K
20 1 Introduction

the β polymorph converts into the γ phase and this interconversion is not reversi-
ble. The γ form can be quenched at 200 K. When heated the γ form decomposes at
504 K. Structurally, the three polymorphs are closely related and quite similar, with
the planarity of the individual FOX-7 layers increasing from α via β to γ (i.e. γ pos-
esses the most planar layers) (Fig. 1.11).
Another member of the family of nitramine explosives is the compound dinitro-
glycoluril (DINGU) which was first reported as early as 1888. The reaction between
glyoxal (O═CH—CH═O) and urea yields glycoluril which can be nitrated with
100 % nitric acid to produce DINGU. Further nitration with a mixture of HNO3 /N2O5
yields the corresponding tetramine SORGUYL. The latter compound is of interest
because of its high density (2.01 g cm–3 ) and its high detonation velocity (9150 m s–1 )
(Fig. 1.12). SORGUYL belongs to the class of cyclic dinitroureas. These compounds
generally show a higher hydrolytic activity and may therefore be of interest as
“self-remediating” energetic materials.
A new neutral nitrimino-functionalized high explosive which was first mentioned
in 1951 (J. Am. Chem. Soc. 1951, 73, 4443, see also Damavarapu et al., OPR & D,
2016, 683–686) and which was recently suggested as a RDX replacement in C4 and
Comp.B by Damavarapu (ARDEC) is bisnitraminotriazinone (DNAM). This compound
has a melting point of 228 °C and a remarkably high density of 1.998 g/cc. Due to the
high density and the not too negative enthalpy of formation (ΔH °f = –111 kJ mol–1 )
DNAM has a detonation velocity of 9200 m s–1 but still desirably low sensitivities
(IS = 82.5 cm, FS = 216 N, ESD = 0.25 J). The synthesis of DNAM can be achieved in
50–60 % yield by nitration of melamine using in-situ generated AcONO2 as the
effective nitrating agent (Fig. 1.13a) or by direct nitration of melamine. One possible
concern about DNAM is that the compound hydrolyzes rapidly at 80° with libera-
tion of nitrous oxide. At room temperature, the hydrolysis requires one to two days
and is acid catalyzed.
The reaction of DNAM with NaHCO3 , CsOH and Sr(OH)2 · 8 H 2O yields the corre-
sponding mono-deprotonated salts NaDNAM, CsDNAM and Sr (DNAM)2 , respec-
tively.
Pyrazine derivatives are six-membered heterocyclic compounds containing two
nitrogen atoms in the ring system. As high-nitrogen heterocylic compounds, they
have an ideal structure for energetic materials (EMs). Some of them have a high
formation enthalpy, fine thermal stability and good safety characteristics. The basic
structure of energetic pyrazine compounds is that of 3,5-dinitro-2,6-diaminopyra-
zine (I in Fig. 1.13). One of the most prominent members in this family is the
1-oxide 3,5-dinitro-2,6-pyrazinediamine-1-oxide (also known as LLM-105, Fig. 1.13).
LLM-105 has a high density of 1.92 g cm–3 and it shows a detonation velocity of
8730 m s–1 and a detonation pressure of 359 kbar which are comparable to those
of RDX (density = 1.80 g cm–3, exptl. values: VoD = 8750, PC-J = 347 kbar). LLM-105
is a lot less impact sensitive than RDX and is not sensitive towards electrostatics
and friction [1d].
 1.2 New Developments 21

O
N
C
H

b
(a)
c
a

(b)
b

c
a

c
(c) b

Fig. 1.11: Crystalline packing of α-FOX-7 (a), β-FOX-7 (b) and γ-FOX-7 (c).
22 1 Introduction

O O

O2N N N H O2N N N NO2

H N N NO2 O2N N N NO2

O O

DINGU SORGUYL

Fig. 1.12: Molecular structures of dinitroglycoluril (DINGU) and the corresponding tetramine
(SORGUYL).

N N O2N N NO2
NaOMe HNO3
MeOH H2SO4
Cl N Cl Cl N OMe Cl N OMe

O2N N NO2 O2N N NO2

NH3 H2O2
CF3COOH
H2N N NH2 H2N N NH2
O

Fig. 1.13: Synthesis of LLM-105 starting from 2,6-dichloropyrazine. 3,5-dinitro-2,6-diaminopyrazine

is oxidized to 3,5-dinitro-2,6-pyrazinediamine-1-oxide (LLM-105) in the final step.

NH2
O
N N

HNO3 H2N N NH2

HN NH
Ac2O AcONO2
 15 °C  10 °C N N N
H
NO2 NO2

DNAM

Fig. 1.13a: Synthesis of DNAM.

The synthesis of LLM-116 is shown in Fig. 1.13c.

Another N-oxide which has recently been suggested by Chavez et al. (LANL)
as an insensitive high explosive is 3,3′-diaminoazoxy furazan (DAAF). Though the
detonation velocity and detonation pressure of DAAF are rather low (7930 m s–1,
306 kbar @ 1.685 g/cc), the low sensitivity (IS > 320 cm, FS > 360 N) and a critical
diameter of < 3 mm make this compound promising. The synthesis of DAAF is
shown in Fig 1.13b [see also E.-C. Koch, Propellants, Explosives, Pyrotech, 2016,
41, 529–538].
 1.2 New Developments 23

H2N NH2 H2N NHOH H2N N O H2N NO2

H2SO4
N N 30% H2O2 N N N N N N
O O O O
DAF Hydroxylamine Nitroso ANF

O
H2N N N NH2

N N N N
O O
DAAF

Fig. 1.13b: Synthesis of DAAF.

Fig. 1.13c: Synthesis of LLM-116.

There are various methods to prepare LLM-105. Most methods start from commer-
cially available 2,6-dichloropyrazine (Fig. 1.13) and oxidize dinitropyrazinediamine
in the final step to the 1-oxide (LLM-105).
Organic peroxides are another class of explosives which has been researched
recently. This class of explosives (organic, covalent peroxides) includes the follow-
ing compounds:
– H 2O2
– peracids, R—C(O)—OOH
– peresters, R—C(O)—OO—R′
– perethers, R—O—O–R′
– peracetals, R′2 C—(OOR)2.
– peroxyanhydride, R—C(O)—O—O—C(O)—R′

Triacetone triperoxide (TATP, Fig. 1.14) is formed from acetone in sulfuric acid
solution when acted upon by 45 % (or lower concentration) hydrogen peroxide (the
acid acts as a catalyst). Like most other organic peroxides TATP has a very high
impact (0.3 J), friction (0.1 N) and thermal sensitivity. TATP has the characteristics
of a primary explosive. For this reason and because of its tendency to sublime
(high volatility) it is not used in practice (apart from terrorist and suicide bomber
activities).
24 1 Introduction

N
O O
O O O O O
O O O O
O O O OH
HO O O
O O
O O N

TATP HMTD MEKP DADP

Fig. 1.14: Molecular structures of triacetone triperoxide (TATP), hexamethylene triperoxide diamine
(HMTD), methyl ethyl ketone peroxide (MEKP) and diacetone diperoxide (DADP).

Because of the use of TATP by terrorists, a reliable and fast detection of this materi-
al is desirable. In addition to conventional analytical methods such as mass spec-
trometry and UV (ultra violet) spectroscopy specially trained explosive detection
dogs (EDD) play an important role in the detection of organic peroxides. However,
fully trained EDDs are expensive (up to $ 60 k) and can only work for 4 h per day.
Although the high vapor pressure helps the dogs to detect the material, it is also a
disadvantage because of the limited time-span in which the dog is able to find it
(traces may sublime and disappear forever). Matrices in which the compounds can
be imbedded are sought after for safe training of explosive detection dogs. These
matrices should not have any volatility or any characteristic smell for the dogs. In
this respect zeolites may be of interest [1e, f]. The ongoing problem with zeolites is
that they need to be loaded with solutions and the solvents (e.g. acetone) may not
completely vaporize before the peroxide.
Typical organic peroxides, which have been or may be used by terrorists are
so-called homemade explosives (HMEs): triacetone triperoxide (TATP), hexameth-
ylene triperoxide diamine (HMTD), methyl ethyl ketone peroxide (MEKP) and diac-
etone diperoxide (DADP) (Fig. 1.14).
The following class of N-oxide compounds is considerably more stable than
the above mentioned peroxides. For example, the oxidation of 3,3′-azobis(6-amino-
1,2,4,5-tetrazine) in H 2O2 / CH 2Cl2 in the presence of trifluoroacetic acid anhydride
yields the corresponding N-oxide (Fig. 1.15). This compound has a desirable high
density and only modest impact and frictiteon sensitivity.
Another oxidizing reagent that has proven useful at introducing N-oxides is
commercially available Oxone® (2 KHSO5 · KHSO4 · K2SO4 ). The active ingredient
in this oxidizing agent is potassium peroxomonosulfate, KHSO5 , which is a salt of
Caro’s acid, H 2SO5 . Examples of oxidation reactions involving Oxone® are shown
in Figure 1.16, including the interconversion of an amine (R3N) into an N-oxide.
(N.B. Sometimes, mCPBA [meta-chloro perbenzoic acid] or CF3COOH are also used
as an oxidizing agent for form N-oxides.)
Another tetrazine derivative, 3,6-bis(1 H-1,2,3,4-tetrazole-5-ylamino)-s-tetrazine,
has recently been prepared from (bis(pyrazolyl)tetrazine (Fig. 1.15). It is interesting
to note that the tetrazine derivatives potentially form strong intermolecular interac-
 1.2 New Developments 25

O
N N O N N
N N N NH2 [O] N N N NH2
H2N N N N H2N N N N
N N N N O
(a) O

H N N H
N N N N N
N N N N N N
N N N N HN HN N
(b) N N

Fig. 1.15: Synthesis of an N-oxide (a) and preparation of 3,6-bis(1H-1,2,3,4-tetrazole-5-ylamino)-s-

tetrazine (b).

R 3N O RCO2H RCO2 Me

R3N
RCHO RCH(OMe)2

O
R RSR
KHSO5 RSO2R
R

R 3P R R
R3 B

(RO)3B R3P O RCO2H

Fig. 1.16: Oxidation reactions with Oxone® as the oxidant (see for example: B. R. Travis,
M. Sivakumar, G. O. Hollist, B. Borhan, Org. Lett. 2003, 5, 1031–1034).

tions via π-stacking. This can influence many of the physical properties in a posi-
tive way, for example by reducing the electrostatic sensitivity.

1.2.3 New Primary Explosives

In early days Alfred Nobel already replaced mercury fulminate (MF, see above),
which he had introduced into blasting caps, with the safer to handle primary explo-
sives lead azide (LA) and lead styphnate (LS) (Fig. 1.17). However, the long-term
use of LA and LS has caused considerable lead contamination in military training
grounds which has stimulated world-wide activities in the search for replacements
that are heavy-metal free. In 2016 the US military still used ca. 2000–3000 kg LA
per year. In 2006 Huynh und Hiskey published a paper proposing iron and copper
complexes of the type [cat]+2 [MII(NT)4(H 2O)2 ] ([cat] + = NH 4+, Na+; M = Fe, Cu;
26 1 Introduction

O
O2N NO2
Pb 2
O
NO2

NO2
N
C cat  NH4, Na
[cat] 2 (H2O)2 M 2
N
N M  Fe, Cu
N
4

CH3
O N
N
[Cu] 2 O N N C Pb(N3)2
N
N
2

O O
N O2N N
N
Cu C NO2 K O
N N
N
NO2
DBX-1 KDNP

Fig. 1.17: Molecular structures of lead styphnate (LS), lead azide (LA), an iron and
copper nitrotetrazolate complexes as well as copper(I) 5-nitrotetrazolate (DBX-1) and
potassium-7-hydroxy-6-dinitrobenzofuroxane (KDNP).

NT = 5-nitrotetrazolate) as environmentally friendly, “green” primary explosives

(Fig. 1.17) [3].
In 2007 the LMU Munich research group reported on the compound copper
bis(1-methyl-5-nitriminotetrazolate) with similarly promising properties (Fig. 1.17)
[4]. Because they have only been discovered recently, none of the above mentioned
complexes has found application yet, but they appear to have substantial potential
as lead-free primary explosives.
Another environmentally compatible primary explosive is copper(I) 5-nitrotet-
razolate (Fig. 1.17). This compound has been developed under the name of DBX-1
by Pacific Scientific EMC and is a suitable replacement for lead azide. DBX-1 is
thermally stable up to 325 °C (DSC). The impact sensitivity of DBX-1 is 0.04 J (ball-
drop instrument) compared with 0.05 J for LA. The compound is stable at 180 °C
 1.2 New Developments 27

ca. 0.147 in

Fig. 1.18: Typical design of a stab detonator; 1: initiating charge, stab mix, e.g.
NOL –130 (LA, LS, tetrazene, Sb2S3, Ba(NO3 )2 ); 2: transfer charge (LA); 3: out-
put charge (RDX).

for 24 hrs in air and for 2 months at 70 °C. DBX-1 can be obtained from NaNT and
Cu(I)Cl in HCl/H2O solution at a higher temperature. However, the best preparation
for DBX-1 in a yield of 80–90 % is shown in the following equation where sodium
ascorbate, NaC6H7O6 , is used as the reducing agent:

reducing agent, H2O, 15 min, ΔT

CuCl2 + NaNT ――――――――――――――→ DBX-1

The mercury salt of NT, Hg (NT)2 , is also known under the name DXN-1 or DXW-1.
A possible replacement for lead styphnate is potassium-7-hydroxy-6-dinitro-
benzofuroxane (KDNP) (Fig. 1.17). KDNP is a furoxane ring containing explosive
and can best be prepared from commercially available bromo anisol according to
the following equation. The KN3 substitutes the Br atom in the final reaction step
and also removes the methyl group:

O O
O2N NO2
nitration 2 KN3
KDNP
DT, CH3OH
Br
NO2

A typical stab detonator (Fig. 1.18) consists of three main components:

1. initiating mixture or initiating charge (initiated by a bridgewire),
2. transfer charge: primary explosive (usually LA),
3. output charge: secondary explosive (usually RDX).
28 1 Introduction

A typical composition for the initiating charge is:

20 % LA,
40 % LS (basic),
5 % tetrazene,
20 % barium nitrate,
15 % antimony sulfide, Sb2S3 .

It is therefore desirable, to find suitable heavy metal-free replacements for both

lead azide and lead styphnate. Current research is addressing this problem. The
following replacements in stab detonators are presently being researched:
1. initiating charge LA → DBX-1
LS → KDNP
2. transfer charge: LA → triazine triazide (TTA) or APX
3. output charge: RDX → PETN or BTAT

Primary explosives are substances which show a very rapid transition from defla-
gration to detonation and generate a shock-wave which makes transfer of the deto-
nation to a (less sensitive) secondary explosive possible. Lead azide and lead styph-
nate are the most commonly used primary explosives today. However, the long-term
use of these compounds (which contain the toxic heavy metal lead) has caused
considerable lead contamination in military training grounds. Costly clean-up
operations require a lot of money that could better be spent improving the defense
capability of the country’s forces. A recent article published on December 4th 2012 in
the Washington Post (http://www.washingtonpost.com/blogs/federal-eye/wp/2012/
12/03/new-report-warns-of-high-lead-risk-for-military-firing-range-workers/) entitled
“Defense Dept. Standards On Lead Exposure Faulted” stated: “… it has found over-
whelming evidence that 30-year-old federal standards governing lead exposure at
Department of Defense firing ranges and other sites are inadequate to protect work-
ers from ailments associated with high blood lead levels, including problems with
the nervous system, kidney, heart and reproductive system.”
Devices using lead primary explosives − from primers for bullets to detonators
for mining − are manufactured in the tens of millions every year in the United
States. In the US alone, over 750 lbs. of lead azide are consumed every year for
military use.
Researchers from LMU Munich have now synthesized in collaboration with AR-
DEC at Picatinny Arsenal, N.J. a compound named K2DNABT (Fig. 1.18a), a new
heavy metal-free primary explosive which has essentially the same sensitivity (im-
pact, friction and electrostatic sensitivity) as that of lead azide, but does not con-
tain toxic lead. Instead of lead, it contains the ecologically and toxicologically be-
nign element potassium instead. Preliminary experimental detonation tests (dent-
plate tests) and high-level computations have shown that the performance of
K2DNABT even exceeds that of lead azide. Therefore, there is great hope that toxic
 1.2 New Developments 29

+
O2N K
N

N N
N N N
N
Cu+ NO2
N N
N N N
N
+
K N
NO2

K2DNABT DBX–1

Fig. 1.18a: Chemical structures of K2DNABT and DBX-1.

lead azide and / or lead styphnate can be replaced in munitions and detonators
with this physiologically and ecologically benign compound.
In theory, unprotected 1,1′-diamino-5,5′-bistetrazole can be nitrated. However,
the amination of 5,5′-bistetrazole is a procedure which results in only low yields
and also requires considerable effort, therefore an alternative route was developed.
The bisnitrilimine would appear to be a suitable precursor, however, unfortunately
unprotected bisnitrilimine is not known and only the corresponding diphenyl de-
rivative is known. Therefore another derivative was prepared which contains a
more easily removable protecting group than the phenyl group. The synthetic
sprocess for the synthesis of K2 DNABT starts from the easily preparable dimethyl
carbonate. This is reacted with hydrazine hydrate to form the carbazate 1. The sub-
sequent condensation reaction with half an equivalent of glyoxal forms com-
pound 2, which is subsequently oxidized with NCS (N-chlorosuccinimide) to the
corresponding chloride. Substitution with sodium azide offers the diazide (in only
38 % yields) which then is cyclized with hydrochloric acid in ethereal suspension.
The carboxymethyl protected 1,1′-diamino-5,5′-bistetrazole is then gently nitrated
with N2O5 (Fig. 1.18b).
An alkaline aquatic work-up with KOH precipitates dipotassium 1,1′-dinitrami-
no-5,5′-bistetrazolate. The products of the individual stages can be purified by re-
crystallization, or used as obtained. No column chromatography must be used.
Fortunately K2DNABT shows low water solubility, which (i) facilitates its isolation
and purification and (ii) avoids future toxicity problems due to potential ground
water pollution.
A primary explosive is an explosive that is extremely sensitive to stimuli such
as impact, friction, heat or electrostatic discharge. Only very small amounts of en-
ergy are required to initiate such a material. Generally, primary explosives are con-
sidered to be materials which are more sensitive than PETN. Primary explosives
are described as being the initiating materials that initiate less sensitive energetic
materials such as secondary explosives (e.g. RDX/HMX) or propellants. A small
quantity − usually only milligrams − is required to initiate a larger charge of explo-
30 1 Introduction

O
O O H
N2H4 1/2 eq. glyoxal N N O NCS
95 % NH2 90 % O N N 72 %
H
O O O N
1 H 2 O NCS =
Cl
O N
O

O Cl O N3
H H
O NaN3 N N O HCI
N N
O N N O N N
H 38 % H Et2O
3 N3 4 O
Cl O

O O
+
O O 2N K
O N
O2N N
HN
KOH N N
N N N N
N N N2O5 61 %
N N N N
N N
N N N N N N
N N N N
+
K N NO2
NH N NO2
O O
K2DNABT
5 6
O O

Fig. 1.18b: Synthetic pathway for the formation of K2DNABT.

sive which is safer to handle. Primary explosives are widely used in primers, detona-
tors and blasting caps. The most commonly used primary explosives are lead azide
and lead styphnate. Lead azide is the more powerful of the two and is used as a
pure substance typically in detonators as a transfer charge, or in formulations for
initiation mixes (e.g. NOL-130). Lead styphnate is mostly used in formulations for
initiation and primer mixes and is rarely found as a neat material in applications.
Although lead azide has been used extensively for decades, it is a very poison-
ous material that reacts with copper, zinc or alloys containing these metals, form-
ing other azides that can be highly sensitive and dangerous to handle. Further-
more, lead-based materials have been clearly found to cause environmental and
health related problems. Lead-based materials are included on the EPA Toxic
Chemical List (EPA List of 17 Toxic Chemicals); they are additionally regulated un-
der the Clean Air Act as Title II Hazardous Air Pollutants, as well as classified as
toxic pollutants under the Clean Water Act, and are on the Superfund list of haz-
ardous substances. Under the Clean Air Act, the USEPA (US Environmental Protec-
tion Agency) revised the National Ambient Air Quality Standard (NAAQS) to
0.15 μg/m3, which is ten times more stringent than the previous standard. Lead is
both an acute and chronic toxin, and the human body has difficulty in removing
it once it has been absorbed and dissolved in the blood. Consequently, a chief
concern is the absorption of lead by humans who are exposed to the lead-contain-
ing constituents of the initiating mix, as well as the combustion by-products of
lead-based compositions. The health effects of lead are well documented however,
recent studies have shown that there are no safe exposure levels for lead, particu-
larly for children. There is a direct correlation between lead exposure and develop-
 1.2 New Developments 31

Fig. 1.18c: Primer performance test setup.

ment, including IQ loss (even at the revised lead NAAQS, exposure levels are con-
sistent with an IQ loss of over 2 points), behavioral issues and even hearing loss.
Their use during training and testing deposits heavy metals on ranges and can
impact sustainable use of these ranges.
These initiator and transfer charge compositions also require expensive han-
dling procedures during production and disposal. The manufacturing of any lead-
based primary explosives, such as lead azide or lead styphnate, results in the pro-
duction of significant quantities of highly toxic, hazardous waste. In addition, the
handling and storage of these compounds is also a concern.
Due to its environmental and health impact, there is a need to develop green
primary explosives, to replace lead-based compounds. Current research seeks to
replace lead azide and lead-based formulations in commonly used detonators, and
in the M55 stab detonators and percussion primers, such as M115, M39, M42, etc.
in particular. One important strategy for developing lead-free alternatives focuses
on the use of high-nitrogen compounds. High-nitrogen compounds are widely con-
sidered to be viable, environmental-friendly energetic, since the predominant deto-
nation product is non-toxic nitrogen (N2 ) gas. At the same time, high-nitrogen com-
pounds possess high enthalpies of formation (ΔHf ), which lead to high energy
outputs. In developing/testing viable lead replacements, the following criteria
must be considered for new compounds. The material:
– must be safe to handle and possess a rapid deflagration to detonation transition
– be thermally stable to temperatures above 150 °C and must have a melting
point greater than 90 °C
– should possess high detonation performance and sensitivity
– should have long term chemical stability
– should not contain toxic heavy metals or other known toxins
– be easy to synthesize and affordable.
32 1 Introduction

Fig. 1.18d: Performance of K2DNABT/ RDX after initiation by an electrical igniter.

Tab. 1.3a: Comparison of the sensitivities of K2DNABT with other primary explosives.

sample Impact / in Friction / N ESD / mJ Density / g cm−3 VoD / m s−1

LA 7−11 0.1 4.7 4.8 5300

LS 5 0.1 0.2 3.00 4900
DBX-1 4 0.1 3.1 2.58 ca. 7000
K2DNABT 2 0.1 0.1 2.2 ca. 8330

For primer performance testing, primers are sealed in an air-tight test apparatus
and initiated by dropping an 8 or 16 oz steel ball onto the primary explosive. Pres-
sure transducers measure the output (Fig. 1.18c).
The sensitivity of K2DNABT was tested and was found to be very sensitive to
impact, friction and ESD, as all primary explosives are. K2DNABT is more sensitive
compared to lead azide, lead styphnate and DBX-1 (as shown in Tab. 1.3a).
To compare the performance of K2DNABT with that of lead azide, 40 mg of
K2DNBT was loaded in a small aluminum holder and 1 g of RDX was pressed in a
standard detonator copper shell. This was initiated by an electrical igniter. The
performance of K2DNABT/RDX was shown to pass the requirements expected of a
primary explosive mixture as can be seen in Fig. 1.18d.
A modified Small Scale Shock Reactivity Test (SSRT) was performed with
K2DNABT as well as with lead azide for comparison. In these tests, 500 mg of each
compound was ignited by an igniter and it was found that K2DNABT showed more
indentation than lead azide on the witness plate (Fig 1.18e).
When performed electrically, K2DNABT is comparable to lead styphnate in per-
formance. Primer mixes have been also been formulated and require testing.
Future work requires optimization of the system in order for K2DNABT to be
considered as a replacement for lead azide in detonators. From the initial results,
K2DNABT appears to be a good possible replacement for lead styphnate when initi-
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the Common Prayer-book and the Bible. In this region, where the
snuffle of the Yankee mixes with the haspirations of the Cockney, the
really Parisianized Englishman is never seen, and if compelled to
pass through it he hurries with muffled face in trembling haste, like
Mahomet rushing down the demon-haunted defiles of El Hidjr.
"Milan is bravely raising a monument to Napoleon III., whilst the
popular feeling of young Italy runs strong against the French. The
main reasons appear to be the abstraction of Nice, and the
domineering tone assumed by the late Empire. Moreover, 'the
peoples' (Kossuth still lives at Turin) do not readily pardon their
benefactors. Witness the aversion of Spain and Portugal for England
since the Peninsular War. In the next campaign the general voice of
the younger and more fiery sort, and of that solid power, the Left
Centre, will compel the constitutional Government of Victor
Emmanuel, despite all his prepossessions and prejudices, to side
with Germany against France. This was written years ago, but it is,
methinks, still true.
"I was astonished to find the Italianissimo feeling so rampant in
Upper Italy, and the people so excited upon the subject, when their
Government have set them an example of calmness, common sense,
moderation, and constitutional spirit of compromise, which go far to
redeem the character of the Latin race, even in this, the darkest day
of its history. Because Dante made the Quarnero Gulf finish Italy,
and because Petrarch established the Alps as the surroundings of his
fair land, their new geographical politicians would absorb Trieste and
Istria; and when Jove shall wax wroth, he will probably grant them
their silly prayer.
"Trieste has a mixed population. North of Ponte Rosso is Germania,
composed of the authorities, the employés, and a few wealthy
merchants. They have a maniacal idea of Germanizing their little
world, a mania which secures for them abundant trouble and ill-will,
for eight millions cannot denationalize thirty-two millions. There are
twelve thousand Italians at Trieste who speak a corrupted Venetian;
eleven thousand of these are more or less poor, one thousand are
perhaps too rich. However, their civilization is all Roman, and they
take a pride in it, whilst the exaltés and the Italianissimi hate their
rulers like poison. In this they are joined by the mass of the wealthy
and influential Israelites, who divide the commerce with the Greeks.
The former subscribe handsomely to every Italian charity or
movement; and periodically and anonymously memorialize the King
of Italy. The lower class take a delight in throwing large squibs, here
called by courtesy 'torpedoes,' amongst the unpatriotic petticoats
who dare to throng the Austrian balls. The immediate suburbs,
country, and villages are Slav, and even in the City some can barely
speak Italian. This people detests all its fellow-citizens with an
instinctive odium of race, and with a dim consciousness that it has
been ousted from its own. Thus the population may be said to be
triple. Politics are lively, and the Italianissimi thrive because the
constitutional Government, which has taken the place of the old
patriarchal despotism, is weak, acting as if it feared them. Austria of
to-day is feeble and gentlemanly, and as such is scarcely a match for
the actual Italy. Let us lay out a little map of politics immediately
around our small corner of the world.
"Being devoted Austrians, we have many anxieties concerning the
political health of this admirable country. Austria, once so famed for
the astute management, the 'Politiké,' which kept in order the most
heterogeneous of households between Bohemia and Dalmatia, and
from Hungary to the Milanese, is suffering from a complication of
complaints. The first is the economic: her deficit for 1877 is already
laid at twenty-six millions of florins; she lives on paper, and she
habitually outruns the constable. Secondly, are the modus vivendi
with Hungary, the Convention, the Bank, and half a dozen other
troubles, which result from the 'chilling dualism' of Count Beust
(1867). The inevitable rivalry of a twofold instead of a threefold
empire is now deepening to downright hostility. The Slavs complain
that the crown of the Empire is being dragged through the mire by
the 'Magyarists;' and on December 9th, the Vienna Chamber of
Deputies heard for the first time a proposal to substitute Trialism for
Dualism. Third, and last, is the Eastern Question, in which the poor
invalid is distracted by three physicians proposing three several
cures. Doctor Hungary wants only the integrity (!) of Turkey: alliance
with England, war with Russia. Doctor Germany, backed by the
Archduke Albert, and aided by the army, looks to alliance with
Russia, and to the annexation of Bosnia and the Herzegovina when
Turkey falls to pieces. Lastly, Doctor Progressist, with the club of the
Left, advocates the cold-water treatment, absolute passivity: no
annexation, no occupation, no intervention. The triad division seems
inveterate: even the Constitutionalist party must split into three—a
Centrum, a Left, and a Fortschritts partei. Hence Prince Gortschakoff,
not without truth, characterized this mosaic without coherence as
'no longer a State, but only a Government.'
"Austria, like England, is suffering from the manifold disorders and
troubles that accompany a change of life. At home we have thrown
over for ever the rule of Aristocracy; and we have not yet resigned
ourselves to what must inevitably come—Democracy pure and
simple. Accordingly, we sit between two stools, with the usual
proverbial result. Austria, in 1848, sent to the Limbo of past things
the respectable 'paternal government,' with its carcere, its carcere
duro, and its carcere durissimo; and threatened to make sausage-
meat of M. Ochsenhausen von Metternich. Constitutionalism,
adopted by automatism, found the Austrians utterly unfit for
freedom; and the last thirty years have only proved that
constitutionalism may be more despotic than despotism. Austria has
ever been the prey of minorities, German and Magyar. Her Beamter
class has adopted the worst form of Latin Bureaucratie. Her Press
has one great object in life, that of 'Germanizing' unwilling Slavs. Her
fleet has lost Tegetthoff and Archduke Max. Her army, once the best
drilled in Europe, and second to none in the ingens magnitudo
corporum, has been reduced by short service to a host of beardless
boys; and the marvels of the Uchatius gun will not prevent half the
regiments being knocked up by a fortnight's work. But these are the
inevitable evils of a transition system, and if Austria can only tide
over her change of life, she will still enjoy a long, hearty, and happy
old age.
"Hence Austro-Hungary is freely denounced as 'disturbing the
European Areopagus.' Hence Paskievich declared in 1854 that the
road to Stamboul leads through Vienna. Hence Fadajeff, the
Panslavist, significantly points out that Europe contains forty millions
of Slavs who are not under the White Czar. These ancient Scythians
have hitherto shown very little wisdom. Instead of cultivating some
general language,—for instance, the old Slavonic, which would have
represented Latin,—they are elaborating half a dozen different local
dialogues; and, at the last Slav Congress, the Pan-Slav Deputies,
greatly to the delight of the Pan-Germanists, were obliged to
harangue one another in German. If 'Trialism' be carried out in the
teeth of Hungary, what and where can be the capital of the Jugo-
Slavs—the Southern and Latin, as opposed to the Pravo-Slavs or
orthodox? Where shall be the seat of its Houses? Prague is purely
Czech, utterly distasteful to Slavonia, Croatia, and Dalmatia. Laibach
in Krain is the only place comparatively central; but that means that
all would combine to reject Laibach. Meanwhile the Slavs declare
that they are treated as Helots, and that they will stand this
treatment no longer.
"Austria will hardly declare war against Russia even at the bidding of
the Turko-Hungarian alliance—even if menaced with her pet
bugbear, the formation of a strong Slav kingdom, or kingdoms, on
her south-eastern frontier. She is thoroughly awake to the danger
threatened by her friends, that of falling into her four component
parts, each obeying the law of gravitation—Styria, Upper and Lower,
absorbing herself in Germany, and Dalmatia and Istria merging into
Italy. She has made all her preparations for occupying Bosnia, which
the Turks are abandoning, and for which it is generally believed they
will not fight. Count Andrassy, the rebel of 1848, the Premier of
1876-78, will keep his own counsel and carry out his own plans. He
has been unjustly charged with a vacillating and uncertain policy; as
if a man who is being frantically pulled diametrically in four opposite
directions were not obliged to stoop at times in order to conquer.
"Italy has of late made strong representations at Vienna against the
possible occupation of Bosnia by Austria. She knows that the step
would for ever debar her from the possessions of Dalmatia; and that
the old kingdom, the mother of Emperors, will never rest satisfied till
her extensive seaboard is subtended by a proportionate interior. Italy
would prefer to occupy Bosnia in propriâ personâ; but, that being
hardly possible, she would leave it occupied, or, worst of all,
occupied by the Turks. Italy is the deadliest enemy of Austria, and
wears the dangerous aspect of a friend. Such is the present
standpoint of the Empire,[4] and you see she is still, as she has been
for years, a 'political necessity.' We, her well-wishers, can only say to
her, in olden phrase, Tu, felix Austria, nube,—'Yea, marry, and take
unto thyself the broad and fertile lands lying behind the Dinaric
Alps.'
"Meanwhile, Italy, the rival sister of France, the recipient of many
favours from her, and, par consequence, her bitterest foe, bides her
time, remains quiet as a church mouse, and, like the Scotchman's
owl, thinks hard. She is at present the last, the only hope of
Latinism. She has shown, since 1870, a prudence, a moderation, an
amount of common sense, comparatively speaking, which have
surprised the world. Ethnologists, who scoffed at 'Panlatinism,' were
overhasty in determining that the game of the Latin race was 'up;'
and that the three progressive families of the future are the English
(including the German and the Anglo-American), the Slav, and the
sons of the Flowery Land. The present standpoint of Italy is this. She
has a treaty with Russia which makes her a spectator. She has
returned an overwhelming majority of the progressists, who aim at
converting her into a Republic; and Italy, classical and mediæval, has
never attained her full development except under Republican rule.
Meanwhile, her 'citizens and patriots' look forward to recovering
Nice, where, in 1860, some 26,000 votes against 160 were polled in
favour of annexation to France. She wants an Algeria, and would like
to find it at Tunis, with Carthage for capital. And finally, she would
fain round off her possessions by annexing from Austria the
Trentine, the county of Gorizia, the peninsula of Istria, including the
chief emporium, Trieste, and even the kingdom of Dalmatia.
"It was not a little amusing to note the expression of simple
amazement with which the general Press of England acknowledged
the discovery that Italy 'actually contemplates' this extension of
territory. Would they be surprised to hear that such has been her
object for the last six hundred years; that in her darkest hour she
has never abandoned her claim; that during the last half-century she
has urged it with all her might, and that at the present moment she
is steadily labouring to the same end? We, who derive experience
from the pages of history, firmly believe that the prize would even
now be in her hands were it not for Prussia, who calculates upon the
gravitation of the Austro-German race, and who already speaks of
Trieste as 'our future seaport.' But why, we ask, cannot Italy rest
contented with Venice, which, after a century of neglect, might by
liberal measures again become one of the principal commercial
centres of Europe?
"Under Augustus the whole of Istria was annexed to the tenth region
of Italy; the south-eastern limits being the Flumen Arsæ, the
modern Arsa, that great gash in the Eastern flank beyond which
began Liburnia. Hence Dante sang ('Inferno,' ix. 113-115)—
'Si come a Pola presso del Quarnaro
Che Italia chiude e i suoi termini bagna,
Fanno i sepolcri tutto 'l loco varo.'
Hence Petrarch (Sonnet cxiv.) declares of his Laura, whose praises
he cannot waft all the world over—
'——udralo il bel paese,
Ch' Apennin parte, e 'l mar circonda e 'l Alpe.'
And who can forget the glorious verse of Alfieri, the first to discern
Italy in the 'geographical expression' of the eighteenth century?—
'Giorno verrà, tornerà giorno in cui
Redivivi ornai gli Itali staranno,
In campo armati,' etc., etc., etc.
"Italy bases her claim to the larger limit, upon geography, ethnology,
and sentiment, as well as upon history. Only the most modest of
patriots contend that the Isonzo river, the present boundary of
Austria, was a capricious creation of Napoleon I. The more ambitious
spirits demand the whole southern watershed of the Julian Alps; nor
are they wanting who, by 'Alps' understanding the Dinaric chain,
would thus include the whole kingdom of Dalmatia inherited from
the Romans.
"Ethnologically, again, Istria declares herself Italian, not Austrian.
Her 290,000 souls (round number) consist of 166,000 Latins to
109,000 Slavs, the latter a mongrel breed that emigrated between
A.D. 800 and 1657; and a small residue of foreigners, especially
Austro-German officials. The Italians are, it is true, confined to the
inner towns and to the cities of the seaboard; still, these scattered
centres cannot forget that to their noble blood Istria has owed all
her civilization, all her progress, and all her glories in arts and arms.
Lastly, 'sentiment,' as a factor of unknown power in the great sum of
what constitutes 'politics,' is undervalued only by the ignorant
vulgus. The Istrians are more Italian than the Italians. Since the first
constitution of 1848, they have little to complain of the Government
in theory, much in practice. Austria, after the fashion of Prussia,
unwisely attempts to 'Germanize' her Italian subjects, who in Istria
outnumber the Teutons by five to one. The true policy of Austria
would be to Italianize the Italians, to Slavonize the Slavs, and to
Magyarize the Hungarians; in other words, to elicit the good qualities
of her four component races, instead of attempting to unrace them.
And her first practical step should be to abolish all idea of
'Germanizing.' If she did not try for it, it might settle itself.
"The chief danger of Italy, at present, is wishing to go too fast. She
would run before she can walk steadily: she forgets the past: she
ignores that her independence and unity were won for, and not by,
her; that each defeat was to her a conquest. She had the greatest
statesman in Europe, Cavour; who so disposed his game, opening it
in 1854 with the Crimean War, and following it up with a seat for
Piedmont amongst the Great Powers in the Congress of Paris, that it
led by a mathematical certainty to Solferino in 1859, and to securing
Rome for a capital in 1870. But 'milor Camillo' is dead, and Prince
Bismarck, who rules in his stead, bluntly says, 'No one can doubt,
even beyond the Alps, that an attack upon Trieste and Istria would
meet the point of a sword which is not Austrian.' Italy must put her
house in order before she can aspire to extend her grounds. Her
income is insufficient for her expenses; her gold is paper; her
currency is forced, and her heavy taxes breed general discontent.
She has a noble estate for agriculture, but her peasants prefer the
stocking to the stocks, the Funds, or the Bank. Her Civil Service is
half paid, and compelled to pay itself. Her Custom-house duties are
a scandal to a civilized power, and her post-office is a farce. Her
army cannot compare, in fighting qualities, with that of Prussia,
Austria, or even France. Her sailors are not tailors, but she cannot
afford a first-rate armour-clad fleet; she was beaten at Lissa, and
her seaboard would easily be blockaded by a great maritime power.
Moreover, she has that dual Government at Rome, and a terrible
skeleton in the cupboard,—her treatment of the Pope.
"The Liberal press and the 'indignation meetings' of Italy have been
alternatively severe and sarcastic upon entente cordiale between the
Vatican and the Seraglio. But the Papal logic is clear and sound. It
says, 'The reverence of Constantine for the Keys transferred the seat
of civil empire to the Byzantium, whereas Anti-Christ Russia founded
the pseudo-throne of Saint Peter in the far north. We fought against
the Moslem when he was an aggressor. Innocent XI., not to mention
the crusader-Popes, preached the liberation of Vienna. Pius I.
worked up to the Battle of Lepanto. But things are now changed.
You, Bulgarian and Bosnian Catholics, have religious liberty, and you
will have political liberty when you deserve it! Meanwhile, obey the
Sultan, who has nothing to do with Christianity, and shun Anti-Christ
—the Czar.' Good logic, I say, cold and clear-drawn; but powerless to
purge away the sentiments, the prejudices, and the passions of
mankind.
"Italy drives the coach too fast. Patriotic Italians declare that
England has no right to hold Malta. Cyprus was under Venice; ergo,
they think it should be under Italy. The Trentine, the Southern Tyrol,
Istria, and Dalmatia, are in the same conditions. The Latin kingdom
has achieved a great position in Japan. She sends her travellers to
explore New Guinea. She aims at being the most favoured nation in
Egypt, where she lately received a severe schiaffo. The Italian
national expedition landed in the dominions of the Khedive without
having had the decency to call upon him in Cairo. You know how the
Egyptian noticed the affront. Finally, she talks of herself as one of
the Powers, ready to occupy the insurgent districts which the Porte
cannot reduce. Such is the actual standpoint of United Italy.
"I will now sketch the state of Hungary, whose ambition threatens to
make her aggressive, entitled, by the press of England, the
'backbone of the Austrian monarchy;' and praised for the 'superior
political organization' with which she has crushed her Slav rivals.
"Since the days, now forgotten, when Prince Esterhazy first flashed,
in London society, his diamond jacket upon the dazzled eyes of the
'upper ten thousand,' the name of Hungarian has been a passport to
favour amongst us. We meet him in the shape of a Kinsky, an
Erdŏdy, or a Hunyadi,—well born, well clad, and somewhat
unlearned, except in the matter of modern languages. But he is a
good rider, a keen sportsman, and a cool player for high stakes—
qualities in one point (only) much resembling Charity. He looks like a
gentleman in a drawing-room and in the hunting-field; he is quite at
home at a fancy ball; he wears his frogged jacket, his tights and his
tall boots, his silks, satins, and furs, with an air; his manners are
courteous, cordial, and pleasant; in money matters he has none of
the closeness of the cantankerous Prussian, none of the meanness
of the Italian; and, lastly, he makes no secret of his sympathy with
England, with the English, and with all their constitution-manias.
What can you want more? You pronounce him a nice fellow, and all,
woman especially, re-echo your words, 'He is such a gentleman!' and
—he received the Prince of Wales so enthusiastically!
"But there is another side (politically speaking) to this fair point of
view. The Hungarian is a Tartar with a coat of veneer and varnish.
Hungary is, as regards civilization, simply the most backward country
in Europe. Buda-Pest is almost purely German, the work of the
Teutons, who, at the capital, do all the work; you hardly ever hear in
the streets a word of Magyar, and the Magyars have only managed
to raise its prices and its death-rate to somewhat double those of
London. The cities, like historic Gran on the Danube, have attempts
at public buildings and streets; in the country towns and villages the
thoroughfares are left to Nature; the houses and huts, the rookeries
and doggeries are planted higgledy-piggledy, wherever the tenants
please; and they are filthier than any shanty in Galway or Cork, in
Carinthia or Krain. The Ugrian or Ogre prairies have no roads, or
rather they are all road; and the driver takes you across country
when and where he wills. The peasantry are 'men on horseback,'—in
this matter preserving the customs of their Hun and Tartar
ancestors. They speak a tongue of Turkish affinity, all their
sympathies are with their blood-kinsmen the Turks, and they have
toiled to deserve the savage title of 'white Turks,' lately conferred
upon them by Europe.
"Fiume, the only seaport of Hungary, is a study of Hungarian
nationality. The town is neatly built, well paved, and kept tolerably
clean by Slav and Italian labour, the former doing the coarse, the
latter the fine work. The port is, or rather is to be, bran-new.
Because Austria chooses to provide a worse than useless, and
frightfully expensive—in fact, ruinous—harbour for Trieste, whose
anchoring roads were some of the best in Europe, therefore (admire
the consequence) Hungary demands a similar folly for her
emporium, Fiume, whose anchoring roads are still better. After
throwing a few million of florins into the water, the works are
committed to the charge of the usual half-dozen men and boys;
moreover, as the port is supposed to improve, so its shipping and its
business fall off in far quicker ratio. Commerce cannot thrive
amongst these reckless, feckless people. There is no spirit of
enterprise, no union to make force, no public spirit; the dead cities
of the Zuyder Zee are bustling New England centres in comparison
with Fiume; and the latter, which might have become the emporium
of the whole Dalmatian coast, and a dangerous rival to Trieste, is
allowing her golden opportunity to pass away never to return. For
when Dalmatia shall have been vitalized by the addition of Bosnia
and the Herzegovina, her glorious natural basins—harbours that can
hold all the navies of the world—will leave Fiume mighty little to do
except what she does now, look pretty and sit in the sun.
"All Englishmen who have lived long amongst Hungarians remark the
similarity of the Magyar and the southern Irish Catholic. Both are
imaginative and poetical, rather in talk than in books; neither race
ever yet composed poetry of the highest class. Both delight in
music; but, as the 'Irish Melodies' are mostly Old English, so the
favourites of Hungary are gypsy songs. Both have the 'gift of the
gab' to any extent, while their eloquence is notably more flowery
than fruity. Both are sharp and intelligent, affectionate and warm-
hearted; easily angered and appeased, delighted with wit, and to be
managed by a bon mot; superficial, indolent, sensitive, punctilious,
jealous, quarrelsome, passionate, and full of fight. Both are ardent
patriots, with an occasional notable exception of treachery; both are
brilliant soldiers; the Hungarians, who formerly were only cavalry
men, now form whole regiments of the Austrian Line. They are
officered by the Germans, who will not learn the language, justly
remarking, 'If we speak Magyar, we shall be condemned for ever to
Magyar corps, and when the inevitable split takes place, where shall
we then be?' Both are bold and skilful riders; and, as the expatriated
Irish Catholic was declared by Louis Le Grand—an excellent authority
upon such matters—to be 'one of the best gentlemen in Europe,' so
Europe says the same of the Hungarian haute volée.
"As regards politics and finance, Buda-Pest is simply a modern and
eastern copy of Dublin. The Hungarian magnate still lives like the
Squireen and Buckeen of the late Mr. Charles Lever's 'earliest style;'
he keeps open house, he is plundered by all hands, and no Galway
landowner of the last generation was less fitted by nature and
nurture to manage his own affairs. Hence he is drowned in debt, and
the Jew usurer is virtually the owner of all those broad acres which
bear so little. An 'Encumbered Estates Bill' would tell strange tales;
but the sabre is readily drawn in Hungary, and the 'chosen people,'
sensibly enough, content themselves with the meat of the oyster,
leaving the shells to the owner.
"This riotous, rollicking style of private life finds its way into public
affairs; and as a model of 'passionate politics,' the Hungarian is
simply perfect. He has made himself hateful to the sober-sided
German and to the dull Slav; both are dead sick of his
outrecuidance; the former would be delighted to get rid of the
selfish and short-sighted irrepressibles, who are ever bullying and
threatening secession about a custom tax, or a bank, or a question
of union. They are scandalized by seeing the academical youth, the
jeunesse dorée of Magyar universities, sympathizing with Turkish
atrocities, declaring Turkey to be the defender of European
civilization, fackelzuging the Turkish Consul, insulting the Russians,
and sending a memorial sabre to a Sirdar Ekrem (Commander-in-
Chief), whose line of march was marked by the fire-blackened walls
of Giaour villages, and by the corpses of murdered Christians, men
and women and babes. Could the Austro-Germans only shake off the
bugbear of Panslavism, they would cut the cable, allow the ne'er-do-
well Hungarian craft to drift away water-logged into hypostatic union
with that big ironclad the Turk; they would absorb the whole of
Bosnia, the Herzegovina, and Albania; they would cultivate the Slav
nationality, and they would rely upon racial difference of dialect and
religion to protect them against the real or imaginary designs of
Russia. Prince Eugène of Savoy, in the last century, a man of wit,
was of that opinion, and so are we.
"Hungary, indeed, is a tinder-box like Montenegro, and much more
dangerous, because her supply of combustible is on a larger scale.
The last bit of puerile folly has been to press for an Austrian military
occupation of Servia; and why? Because an Austrian monitor, being
in a part of the river where 'No thoroughfare' is put up, was fired
upon with ball cartridges by a schildwache (sentinel) from the fort
walls, and exploded, bungler that she was, one of her own shells.
The Hungarians had been raving at the idea of 'occupation' in
Bulgaria, but the moment they saw an opportunity of breaking the
Treaty of Paris, they proposed doing so at once. By-the-by, now that
Prince Wrede, a personâ ingratâ, is removed from Belgrade, you will
hear no more of Servian outrages against Austria. To the 'Magyarists'
we may trace most of the calumnies against the brave and
unfortunate Servian soldiery—lies of the darkest dye, so eagerly
swallowed by the philo-Turk members of the English Press, and
danger of Hungary and her politics of passion. Russians and Turks
might be safely put into the ring together, like 'Down-Easters' in a
darkened room, and be allowed to fight it out till one cried, 'Enough!'
"If these views of Hungary and the Hungarians be true—and they
are our views—you will considerably discount the valuation set upon
them by the Turcophile Press. They were once a barrier against
Tartar savagery, a Finnish race, invited by the Byzantine Emperors to
act as a buffer against Mohammedanism. The three orders of
Magyars—Magnates, Moderates, and Miserables—hate Russia for the
sensible and far-seeing part which she played in 1848-49; all
excitement is apt to spread; even so in a street dog-fight, every cur
thinks itself bound to assist, and to bite and wrangle something or
other, no matter what. And where, we may ask, is the power that
can muzzle these Eastern ban-dogs? who shall take away the
shillelaghs of these Oriental Paddies?
"A taste of Hungarian quality has been given by M. Vambéry in the
columns of the Daily Telegraph. M. Vambéry was born in Hungary, of
Israelitish German parents. Like the sons of Israel generally, he
hates Russia, and he loves England, and probably he has good and
weighty reasons both for his hate and for his love. He was daring
enough to tell us, in his first book of travels, that after dinner with
the Turkish Minister at Teheran—and a very good dinner it was—he
just disguised himself as a dervish, and travelled perfectly incog. for
months and months under Russian eyes, partly through Russian
territory. The Russians must have known every step taken by M.
Vambéry. He saw only what he was allowed to do; and thus Mr.
Schuyler, whose name has, we regret to say, been altered by the
irreverent Turcophile to 'Squealer,' roundly declares that he never
visited the places which he has so well described. You will therefore
regard M. Vambéry's opinions upon the subject of Turkey with
suspicion, and reserve all your respect for his invaluable publications
upon the Turanian dialects, his spécialité. Lieutenant Payer's book
will disappoint you; its main merit is that of having been written by a
Magyar.
"Do not believe these Ugrians to be 'the backbone of the Austrian
Empire,' whatever they may be to its element of weakness, the
Monarchy. And if you are driven to own that the Hungarians 'play the
leading part in the events of Southern Europe,' understand that the
chief end and aim of Magyarist policy is to ruin the Slavs. I am a
strong Austrian, with a great admiration for the Hungarians, who are
to me, personally and individually, most attractive; but this does not
blind me to the disadvantages they, en masse, bring to Austria. I
believe the Slav to be the future race of Europe, even as I hold the
Chinese to be the future race of the East. In writing politics and
history which may live after one is long forgotten, one must speak
the truth, and bury repulsions and attractions.
"Were I Emperor of Austria, I should have the police organized on
English principles. I should punish with death the first two or three
cases of brutal crime. The people are excellent. It speaks highly for
the independent Triestines that, with weak laws, and authorities that
act as though they dreaded them, the worst crimes are only
stabbing when drunk, and suicide; and the latter is entirely owing to
the excitability of the climate and the utter throwing off of religion,
whilst all moral disgrace or dread is removed by the applause
conferred on the suicide, and sympathy with the surviving family—
which last is good and noble. I have seen thousands accompanying
a felo de se to the grave, with verses and laurel leaves and a band
of music, as if he had done something gallant and brave. Indeed,
one was considered very narrow-minded for not joining in his eulogy.
"They say that forty years ago Trieste was a charming place to live
in; but that, with increase of trade, luxury and money flowed in and
faith flowed out. Let us say that the population is 150,000, with
suburbs; 20,000 are practical Catholics, 30,000 are freethinkers, and
90,000 are utterly indifferent. In fact, the national religion is dying
out; and when that is so in a Catholic land, there is nothing to
replace it except Socialism. After repeated outrages and torpedo-
throwing, the Habeas Corpus would have been at once suspended in
free England, and the French would have placed the City under
martial law. The Empire-Kingdom does not, however, disfranchise
the turbulent City by suppressing the local Diet till such time as the
public expression of disloyal feeling shall have disappeared. A more
manly policy would suit better. Trieste is also allowed to retain
peculiar privileges. She is still a free port; her octrois are left to her
for squandering and pillage, and are so heavy that till lately the
adjoining villages consumed sugar which came viâ Holland all round
and through Europe. Trieste has three towns, as well as three races.
The oldest is the Citta Vecchia, which dates before the days of
Strabo. Filthy in the extreme, it is a focus of infection. Smallpox is
rarely absent from it, and it swells the rate of mortality to the
indecent figure of 40 to 50 per 1000 per annum; London being 22,
and Madras 36. The climate is peculiar. It has three winds—the Bora
(Boreas), the Baltic current, the winter wind, cold, dry, highly
electrical, very exciting, and so violent that sometimes the quays
have been roped, and some of the walls have iron rails let in to
prevent people from being blown into the sea. And there have been
some terrible accidents in my time. An English engineer has been
blown from the quay into the hold of a ship (thirty feet). I saw him
in the hospital, a mere jelly, but nothing more; he is well and at
work. A cab and horse have been upset, and also a train. The
summer wind is the Scirocco, straight from Africa, wet, warm, and
debilitating; whilst the contraste means the two blowing together,
and against each other, with all the disadvantages of both.
"Trieste is a political and coy personage, hotly wooed by Italy and by
Germany. The latter openly declares that she is part of the new
Teutonic Empire, and that the eight millions or so of Austro-Germans
ought to belong body and soul to the Fatherland. Meanwhile she is
enjoyed by the Empire-Kingdom, greatly against the grain. A
powerful rival is rising a few miles to the south, in the person of
Croatian Fiume, which has long ago repented her of having cast her
lot with Hungary. The Flanatic Bay of the ancients is magnificent,
almost equalling the scenery of Naples. A French company is
building a port, which will avoid much of the expense and some of
the errors fatal to Trieste; and but for the inveterate backwardness
of the people, the utter ignorance of what progress means, and the
miserable local jealousies, Fiume, connected by a railway with Agram
or Zagabria, might already have risen upon the decline of Trieste;
but Fiume does not see her advantage, and we retain our
supremacy.
"Beyond the Sinus Flanaticus begins the kingdom of Dalmatia, with a
line of natural harbours between Zara and the Bocche di Cattaro,
which are perhaps the finest in the European world. Unhappily, at
present these ports have nothing to export or import. After long and
careful consideration of the question, based upon the impartial
hearing of both sides discussed, we have come to the conclusion,
firstly, that the dualism of 1867 has not been successful; secondly,
that Austria should have been a Triregno; thirdly, that H.I.M. Franz
Josef might still be crowned King of Bohemia as well, and thus
establish a nucleus about which the divided families of Slavs,
especially the estimable Slovenes, the Wends who founded Venice,
could and would group themselves. I am essentially Austrian by
sympathy; but I do not like the Germans to chuckle when they tell
me that the last great Slavonic Congress, which met in 1845, was
compelled, after various failures, to make speeches in German;
because the laughers ignore the fact that Panslavism is still rampant
in Austria, and the clergy puff up the patriotic movement with all
their might, and that schools and colleges are teaching the rising
generation its rights as well as its wrongs. None but an inveterate
theorist, who holds that the Slav race is not to be the race of the
future, would neglect the importance of a people constituting nearly
half the total of Austro-Hungary—nineteen millions out of the thirty-
four which remained after the cession of Venice in 1866.
"The evil action of this unfair dualism is now causing profound
discontent. Dalmatia is the narrowest kingdom in Europe—300 miles
long by 0 to 15 miles broad, the cypher representing the two spots
where Turkey touches the sea. She is a face without a head; the
latter would be Bosnia and the Herzegovina. She has a profusion of
ports which have nothing to port, and a fine seafaring population
ready for, and capable of, any amount of carrying trade, but
condemned to be professors, custom-house officers, and fishers of
sardines. Bosnia, with her unworked mines and forests, her
unimproved flocks and herds, and her hundred other sources of
neglected wealth, is the complement of, a political necessity to,
Dalmatia. Some day she must become Dalmatian, and the sooner
she connects herself with Austro-Hungary by a plébiscite, or some
such civilized instrument, the better it will be for both. The only
drawback to this movement in the far west of the Ottoman Empire is
that it appears to be somewhat premature. Russia has her hands full
in Eastern Asia, and Austria has for some time a hole in her pocket.
No one knows how sick the famous Sick Man really is since his last
attack of Russomania, following his chronic Russophobia[5]—an
attack brought on by our own disgraceful (Liberal) abandonment of
the Black Sea Treaties. None know, save those who have sat by his
bedside, looked at his tongue, and have felt his pulse. He was
breaking fast when he determined to risk a national bankruptcy.
Finding the so-called 'tax of blood' too heavy, he was already talking
of a Christian recruitment, which would have been the beginning of
the end; and the paroxysm induced by sending a few thousand
troops to ravage and lay waste his discontented outlying estates, has
reduced him to the last gasp. For the rebellion, although premature,
is a reality—it will not be put down by paper; it means to last till
next spring, and when the fighting season comes it will call for the
armed intervention of Europe.
"The integrity of the Ottoman Empire has been, since the days of
Chatham, a fortieth article of faith to English statesmen; although
since the publication of Macfarlane's 'Turkey and her Destiny,' every
traveller from Mostar to Bussorah, from Candia to Circassia, has
shown up the miserable misrule which oppresses those fair and
fruitful regions. The British Cabinet till now has not opened its eyes
to ask 'How long?' or has had originality enough or irreverence
sufficient to pull down the old idol, and to propose a remedy for the
present condition of things. The official mind was made up; there
was no more to be said upon the subject. A Government that
preferred peace and present prosperity to the discharge of an
arduous and distasteful duty, laid down its law, determined to let
sleeping dogs lie, till that little matter of the Turkish debt, the
neatest thing done by the arch-enemy of the Ottoman, came like a
thunderbolt and 'roused the spirit of the British Lion.'
"Meanwhile the action of Austria has been sadly trammelled by the
Dualism which she has brought upon herself. The German
population of the Empire naturally dislikes being swamped by the
new influx of Slavs, but it has not proved itself unpatriotic. The
contrary is the case with the kingdom of Hungary—the five millions
of Magyar who, strengthened by the position and the character of
Count Andrassy, have opposed themselves with all their might to the
development of Dalmatia. This is a mistake, because sooner or later
Dalmatia will develop herself without them. The reason that Austro-
German officers joining Hungarian regiments avoid as much as
possible studying the language is that they fear not being allowed to
exchange, and they do not see their way in case of a separation
between the Empire and the Kingdom.
"The British philo-Turk, if any there be now, would characterize the
absorption of Bosnia and Herzegovina—I would even add
Montenegro and Albania, with the frontier of Greece—as a spoliation
of Turkey. Let him prove that it is not a just and right retaliation for
the centuries of injury which she has inflicted, which she still inflicts,
and which she will ever inflict, upon the sacred causes of civilization
and progress. If any casuist declare that the misrule of a
Government, as in the case of Oude, does not justify the annexation
by Powers professing faith in the development of man, in the religion
of humanity; if he put forward that old saw, that 'the end does not
justify the means,' let him be answered that Europe has duties which
she owes to herself; that the first rule of conduct is her own safety,
and that the second is the support of her co-religionists in Europe
and Asia, throughout the Ottoman Empire. The Christian population
equals, if not exceeds, the Mohammedan, and the evident hope with
which it looks forward to emancipation from Islamism deserves the
most careful consideration.
"For the last ten years the relations of Great Britain with Turkey have
been peculiar and unsatisfactory. The Ottoman voice has openly
said, 'The last Englishman who cared for us was Lord Palmerston.
You will assist us if it be to your interest, no matter how we treat
you, well or ill. You do not fight for an idea, like France. You will not
fight for love of us, as in the days of Silistria and Eupatoria. We
prefer an open enemy to a false friend. Go to! We have had enough
of you.' And they showed their especial contempt by their treatment
of English subjects in Turkey; the debts owed to them by the Turk
remain unpaid, and in Syria our fellow-countrymen were the last to
receive the compensation for the destruction of their property in the
massacre of 1860.
"Again, the present is, if any, the moment for us to act, or to
encourage action in others. The stride of the young Colossus is
temporarily, not lastingly, stayed. In future times[6] quien sabe? (but
God avert it!) we may be so hampered by civil disturbances between
Capital and Labour, so trammelled by intestine troubles in Ireland, or
so engaged in external war, that moral force only will not suffice to
give our voice any weight in the European world. And the effect
would be allowing Russia, a vigilant enemy of overpowering
resolution, to annex Turkey in Europe without any attempt to
preserve the last rag of balance of power by strengthening the
hands of Austria.
"Again, there are thousands of our fellow-countrymen scattered over
the surface of Turkey, and were England known to be incapacitated
from using arms, yet having arms and money, it is to be feared that
the first Russian gun fired from Constantinople would be the signal
of a miserable butchery. But it will be said that the Sultan has begun
the task of reform; his last rescript has been more favourable to the
Rayyahs than anything ever issued by Turkey. I reply, it is easy to
have dust thrown in our eyes provided we open them for the
purpose. What have all the Hatts Shereef or Humayoun yet done for
the Christian Turk? We must be made, after the image of David
Urquhart, to believe in such pie-crust promises. Grant we that H.I.M.
the Sultan is sincere, yet he cannot act himself, and there is no one
to act for him. The Turkish official, and, for the matter of that, the
unofficial, society is much like her army. The private is an excellent
man, sober, honest, truthful, brave, and docile to a degree. Promote
him, and he runs through the several grades of bad comparison, not
repenté, but with an agility which surprises the slow northern mind.
As a non-commissioned officer he is bad; higher he is worse; and
command makes him worst. The same with the French peasant; give
him a small emploi, a bit of gold lace, and he falls from an angel to a
demon in a week, without stopping to look round.
"Now back to notre premier amour, Trieste. I associate with
politicians and clever men all day, with open eyes and ears; and an
occasional peep at a despatch makes one learn a great deal, and
form strong opinions. I am neither philo-Turk nor Russ. I am John
Bull to the backbone, with personal Austrian sympathies, and a
strong leaning to all that is of Arab blood.
"This port was once a favourite with the British bird of passage,
especially when embarking with the Austro-Hungarian Lloyd for
Alexandria. But the Northerner did not approve of the line. He liked
his beef and mutton in huge joints, not in slices and cutlets; he
preferred his potatoes in their jackets to pommes de terre à la
maître d'hôtel; in fact, he grumbled about everything, and at Suez
he transferred himself on board the P. and O. like one that had found
a home. The stranger has also been put to flight by the hotel-
managers. This city is one of the dearest in Europe. The shilling, the
lira, and the franc have become the florin; but these gentlemen gild
refined gold, and charge highly for the operation. There are three
establishments which call themselves first-rate, and which
Englishmen would consider decently comfortable. Unhappily, they
belong to companies, not individuals, and they are farmed out to
managers, who squeeze you as the tax-gatherer does the Rayyah.
There are no tables of charges hung up in the rooms, so you pay
according to length of purse, real or supposed. Thus the late Lord
Dalling had a bill of £45 for two days, during which he never dined in
the house, and the present Prince Ypsilante was plundered at the
same time of 950 florins. It is said that he sent for the manager,
and, after settling his account, warmly complimented him upon
being the greatest rascal he had ever had to do with. So the late
Lord Hertford, when paying off his Parisian architect, politely
regretted that he had never had le déplaisir de sa connaissance.
"All the world here is reading M. Charles Yriarte. That popular writer,
the Ipsilon of the Revue des deux Mondes, who spent the winter of
1873-4 in Istria and Dalmatia, Montenegro and Herzegovina,
published his trip in the illustrated journal, the Tour du Monde; and,
the time being propitious, it was translated into Italian at Milan, with
a variety of notes, taking the Italianissimo view of the matter, and
converting a delightful tale of travel into a rabid wrangle of politics.
The Austrian Government has shown a want of knowledge of human
nature, put the book à l'index, confiscating every copy found in the
libraries; consequently we are all devouring it en cachette."

Red Sea. [Here we change from Central Europe to the massacre

at Jeddah in 1858 (the source of the official wigging),
and the cause of cholera.]
"In 1858 there was a cruel, cowardly massacre of the few Europeans
and Christians, including the English and French Consuls, which was
revenged by the French with two bombardments and a fine of
2,241,016 francs. It arose from our suppression of the slave-trade,
and jealousy at finding that the Europeans, whose exports and
imports are worth about £3,000,000, were absorbing the commerce;
moreover, these two feelings still exist. Our present Vice-Consul, Mr.
Wylde, is a man well fitted to the post, which is anything but a
pleasant one. His open-hearted, straightforward, and fearless ways
of dealing with the natives succeed perfectly. He knows what the
native disposition is, and how to treat it, whilst he is of a joyous
temperament and quite insensible to any danger. Still (as he
laughingly remarked to me one day) it would doubtless be much
more comfortable if the morning and evening shell (instead of gun)
were fired into the town; and, joking apart, every passing Man-of-
war ought to have orders to look in en passant, just to call on the
authorities, and to see what the delightful natives have been up to
since the last ship passed. Some day the Wali Pasha of the Hejaz
may be a fanatical hater of Europeans, the Kaimmakám of Jeddah
may be a weak-minded good-intentioned man who cannot keep
things in order, or intestine troubles may draw away the troops; and
these visits are more necessary in places where perpetual orders
from home necessitate an interference with the slave-trade, which
the Arabs are ever ready to resist. There ought to be cruisers
perpetually visiting and reporting upon the condition of all the
outlying little ports, where at present British subjects are unfairly left
to take care of themselves.

"How Cholera spreads—The Jeddah Massacre of 1858.

"One must read 'Une Mission au Hedjaz Arabie,' par Dr. Buez (Paris:
Masson, 1873, Académie de Médecine), which treats of the
epidemics which the Hajj engenders,—the focus of infection for
Egypt, the Mediterranean, and consequently for Europe. At any rate,
one may note the nine conclusions.
"1. Arabia, and especially El Hejaz, with its pure air, does not
originated the morbid elements which express themselves in
dysentery and typhus, cholera and plague. Small-pox, however, in
certain places is always to be dreaded.
"2. Cholera is at present the special genesis of India.
"3. Steamers, though on the whole beneficial to the general health
of the pilgrims, produce new sanitary conditions, and aid greatly in
propagating the choleraic element, thus becoming a permanent and,
at times, a real danger to Europe. The same is the case with
railroads, but to a much less extent.
"4. All the great outbreaks in the Hejaz, notably that of 1865, when
five hundred per diem died at Mecca during the Hajj, were imported,
indirectly or directly, from India, and then spread over the civilized
world.
"5. The problem of preserving Egypt, Syria, the Levant, and Europe
from cholera is to be resolved only through the strictest surveillance,
by competent men, over pilgrims bound from India to the Hejaz, and
to Egypt from the Red Sea ports—Jeddah, Rais, Rabegh, Yambu,
Líth, Gonfodah, Jisán, Hodaydah, Lohayah, Mocha, etc.
"6. The question is complicated by the existence of choleraic foci,
which may be termed secondary and local, as opposed to primitive
or original, where the epidemic has lingered, and possibly has
incubated till again exasperated by occult conditions—telluric,
atmospheric, or hygienic. This fact demands increased measures of
surveillance. They may not be thoroughly satisfactory, but because
we cannot close all the doors we need not leave all the largest open.
"7. At the period of embarking from the Red Sea ports, where
bakshish is the key to most consciences, the local Health Office and
the member of the Sanitary Council annually sent from Stamboul
after the International Conference of 1866 should be assisted by a
special commission of European physicians, who could, moreover,
modify and improve the different 'Passenger Acts.'
"8. 'Long Desert,' a march of twenty-one days, is the best of cordon
sanitaires, alone able to 'purge' infected caravans.
"9. Ergo, when the Hejaz is attacked by cholera the sea-road should
be peremptorily closed to all pilgrims, an operation whose difficulties
have been greatly and needlessly exaggerated; nor should it be
reopened till after at least one pilgrimage season has passed away
without accident.
"To these wise conclusions I would add a truth. All quarantinary
measures are unpopular with Moslems, who regard them as
inventions of the evil one, or, as the vulgar say, 'flying in the face of
Providence.' Moreover, at Mecca it is every man's interest to conceal
the outbreak; and there is always a danger of the earliest cases
finding their way to Jeddah before the existence of cholera is
suspected at the port. Indeed, clean bills have been given under
such circumstances. Evidently, the only remedy for this evil is to
make the special sanitary commission of European physicians meet
annually at Mecca.
"Now, if such great meteoric changes can be effected by a mere
riband of water let into the sand, what will happen when we
submerge a great part of the African Sáhara (whose eastern limits
are unknown), and thereby create a sea, perhaps, bigger than the
Mediterranean? We cannot calculate the possible amount of climatic
modification which such a new offset of the Atlantic might induce;
and some clever men think that the Sáhara Sea is likely to affect
many parts of the Mediterranean basin, and even the whole
southern seaboard of Europe, with changes which may be
deleterious in the extreme. The scirocco from Africa is the summer
wind par excellence of the 'White Sea,' as the Arabs call it, blowing
through half the year, and that half the most dangerous—if we
submerge the desert, say with a foot or two of water upon rotting
vegetation, what will its effect be upon the world's health?

"A new Passenger Act is, I believe, about to appear; let us hope that
it will abate one part of the nuisance. At present we can never feel
safe on board these crowded cattle-pens. An epidemic might break
out any moment; in case of shipwreck all would be lost; and even if
the screw were injured, or the main shaft were to break, hundreds
on board would die of starvation.
"Each ship should be compelled to carry a condensing apparatus and
cooking-ranges, calculated to accommodate the pilgrims; while one
passenger per two tons (registered) should be the maximum of
freightage. Before departure, the devotees ought to be severally and
carefully inspected by the Port Surgeons; at Aden the health officer
should take them in charge; and in case of infectious disease having
appeared on the voyage, they should be quarantined at Perim or at
the Kumarán Islands, off Lohayya. No one after a certain age should
be allowed to embark—the Korán allows him to send a substitute;
and the same is the case with the infirm and with invalids. Each
person should prove that he carries at least four hundred rupees in
ready money, and that he has left with his family sufficient to
support it according to its station: such is the absolute order of the
Hanafi school, to which all these Bengalis belong. On arriving at
Jeddah, all should take out passports from her Majesty's Consulate,
paying a fee of one rupee per head, and the same for visas after
return: the French and the Dutch charge a dollar. Proclamations in
Hindostani and Persian should be issued at the several Presidencies,
and be published in the local papers every year before the annual
preparations for the pilgrimage begin. I am certain that all sensible
Hindí Moslems would be grateful for a measure relieving them from
exorbitant charities, and from the reproach that Hindustan is the
'basest of kingdoms;' whilst we should only be doing our duty,—a
little late, it is true, but better now than neglecting till the evil shall
have become inveterate. That everlasting incuriousness and laissez-
aller of the Anglo-Indian are the only reasons why precautions were
not taken twenty-five years ago.

The Massacre.

"I took some trouble to investigate the causes which led to the
horrible massacre of June 15, 1858. This is far from being an old tale
of times which will not return; it is an example of what may occur
any day in the present excited state of the Moslem world. Moreover,
the conditions under which it occurred are precisely those of the
present moment, and an ugly symptom has just appeared.[7] The
village moplah (Malabar Moslem), who murdered Mr. Conolly, has
been allowed to escape from surveillance at Jeddah, to embark at
Líth, and probably to return to India viâ Makalla in Hadramant. But
as popular memory in England is short upon such subjects, it is
necessary to give a résumé of the facts.
"The innovation of appointing European Consuls to Jeddah, the 'Gate
of the Holy City,' was resented by the Moslems, both on the grounds
of religion and of private interests, especially when protected foreign
subjects began to absorb the greater parts of the commerce. Several
ballons d'essai were launched. In 1848 an attempt was made to
assassinate, near the Medinah Gate, M. Fulgence Fresnel, the
famous Arabist, who was often consulted upon questions of casuistry
by the D.D.'s of Mecca. The criminal was saved by a certain Abdullah
Muhtásib, a Fellah of Lower Egypt, who began life as a baker, and
who rose to be farmer of the octroi and Chief of the Police; thus
being able to bribe and bully à discretion. In 1849, Mr. Consul Ogilvie
was openly insulted in the bazar, and obtained no redress. During
my first visit to Jeddah, Mr. Consul Cole had avoided all troubles by
his firmness and conciliatory manners; but, after his departure, the
so-called 'War of the Sherífs' (1854) suggested a grand opportunity
for despoiling the Christians. Abdullah Muhtásib again appeared as
the villain of the play. He was, however, arrested, and exiled to
Masáwwah by the Wali of the Hejaz, Namik Pasha.
"In 1856 Abdullah Muhtásib returned triumphant from his exile, and
the Sepoy war of 1857 once more offered him a tempting
opportunity. Actively assisted by his son, he brought into the plot the
Kadi (Abd el Kadir Effendi), the Sayyid el Amúli, the Shaykh Bagafur,
Abdullah Bakarum, and the wealthy merchant Yusuf Banaji.
Presently, in June, 1858, during the height of the pilgrimage, it
became known that Captain Pullen, H.M.S. Cyclops, intended to
carry off the Irania, an English ship upon which Turkish colours had
been hoisted. Abdullah Muhtásib and his friends met at the Custom-
house café, and sat, en permanence, to direct the issue of their
conspiracy. At two p.m. on June 15, the ship was worked out, the
boats of the Cyclops left, and the coast was clear.
"Violent harangues in the bazar roused the cry of 'Death to the
Infidel!' The plot burst like a barrel of gunpowder, and at six p.m.
the massacre began. The Sayyid el Amúli took charge of Mr. Page,
whom he beheaded with his own hand; the body was thrown into
the streets to be hacked to pieces by the mob; the house was
plundered, and the flagstaff was torn up. M. Sabatier, however, is in
error when he reports that the English dragoman and kawwás were
murdered: one died lately, and the other, a very old man, is still
living.
"Meanwhile, two bands of ruffians attacked the other objects of their
hate. One rushed to the French Consulate, and broke in the doors
when they were closed by the kawwás. Madame Eveillard was first
stabbed, and then her husband was cut down, despite the heroic
defence of the daughter, Mdlle. Elsie, who, after seizing one of the
chief murderers by the beard, and severely biting his arm, was
wounded by a yataghan in the face. She and the lady's-maid, saved
by the tardy arrival of the kaimmakám (commandant) and two
Government kawwáses, were taken from the blood-bespattered
home to a Turkish house. Monsieur Emérat,[8] the Chancellor, after
bravely fighting for fifteen minutes, was preserved in the same way,
and, sabred in three places, was led by his faithful Algerian, Haji
Mahommed, to the quarters of Hasan Bey, commanding the artillery.
M. de Lesseps was, therefore, misinformed about Mdlle. Eveillard
saving herself by drawing the cushions of the divan over her body,
and by simulating death whilst the murderers slashed at her legs. He
says nothing of the kaimmakám, and he attributes the honour of
saving the two lives to a negro boy and the old Algerine soldier.[9]
The flagstaff was torn down, the tricolour trampled upon, and the
Consulate given over to plunder.
"The other band rushed to the house of Sabá Mascondi, the richest
of the Greek merchants, and therefore the most obnoxious of all the
Christians. My husband well remembers this amiable and inoffensive
man. He had been repeatedly warned, but he refused to believe a
massacre possible till he and his party, some twenty men, mostly
from Lemnos, met one evening. At length, when it was reported that
the Consulates were being pillaged, three of them went out to
inquire. Meanwhile the armed mob rushed in, and instantly cut down
eight; the rest jumping out of the windows, and flying over the
terraces and down the street, to reach the sea. Poor Sabá veiled his
head, and also tried to escape. M. Sabatier heard two accounts of
his death: one was that he was killed in the house of the English
dragoman (an error); the other, that he was recognized in his rude
disguise by the son of Abdullah Muhtásib, who blew out his brains
with a pistol. This is a fact.
"The French Consul-General also relates that the Cyclops, anchored
only three miles off, perceiving a tumult in the town, armed her
boats and sent them to find out the cause; that the crews were fired
upon, and that they returned, without further action, to their ship. It
is hard to believe this. A few shells thrown into Jeddah would have
cleared every street in half an hour. No justification was wanted for
resenting so gross an insult, and instant measures might have saved
some unhappy lives. But in those days we were still under the
glamour of that most unfortunate Crimean War, and modern England
does not, as a rule, encourage her officers to incur any manner of
responsibility.
"The first act of retribution was on the early morning of July 25,
when the Cyclops, at the distance of twenty-five hundred yards,
bombarded Jeddah for two hours. This was repeated till noon on the
26th, when the new Governor-General, Namik Pasha, arrived. The
people, of course, evacuated the town; a few houses were injured, a
minaret was knocked crooked, and some fifteen boats were
destroyed.
"Presently France, who, whatever may have been her sins of
omission and commission, has ever shown a noble jealousy of her
national honour, determined not to be played with after this fashion;
and she sent, not a 'person of rank,' but M. Sabatier, the fittest head
and hand for the work. The inapt and treacherous politic of the Porte
on this occasion bears a fraternal resemblance to her manœuvres
adopted after the massacre of Damascus (1860), with this
difference: at Beyrout there was no Sabatier, but there was a certain
trickster of the first order, Fuad Pasha, whose reckless ambition had
caused the catastrophe. The Sultan appointed, as his Commissioner,
one Ismail Pasha, who hastened off to the Hejaz, and, in concert
with the feeble and negligent Namik Pasha, put to death half a
dozen poor devils, complied a voluminous Mazbatah (procès
verbale), and hurried back to Constantinople with thirty-nine
'compromised' individuals. Heavy bribes had induced him to estimate
the damage done to Christian property at twenty thousand francs. 'Il
était difficile de faire associer les consuls de France et d'Angleterre à
meilleur marché,' is M. Sabatier's only comment upon this part of the
proceeding.
"As Ismail Pasha persisted in conversation with his two fellow-
Commissioners, that his part of the work had been thoroughly done,
and that he was expected at Stamboul, M. Sabatier and Captain
Pullen, R.N., set out in the Cyclops, with the English and French flags
flying together on the mainmast, and reached Jeddah on October
12th, 1859. Here they found Commodore Seymour with the Pelorus
(twenty-one guns); the corvette Assaye (ten guns); and the
Chesapeake (fifty-one guns) expected. Five days afterwards, Namik
Pasha arrived from Mecca; and, as the Turkish Commissioner had
admitted that all the local authorities were accessories to the
murder, M. Sabatier proceeded to examine all witnesses, Moslems as
well as Christians. Even he, accustomed for long years to the
abstruse chicanery of the East, must have been surprised to hear
the Turkish authorities laying the blame upon Captain Pullen; as if a
mere question of maritime and international law could have borne
such fruits. Even he, so well inured to the contempt of European
intelligence—which is an article of faith with all Orientals—must have
been startled, as well as shocked, to see the abominable Abdullah
Muhtásib sitting side by side with Hasan Bey, the wretched
commandant of artillery, when the Consulate of France was still a
mere shell, and the walls were bespattered with the blood of his
fellow-countrymen.
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