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 The Properties of Energetic Materials Sensitivity Physical
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Mohammad Hossein Keshavarz

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Mohammad H. Keshavarz, Thomas M. Klapötke
The Properties of Energetic Materials
De Gruyter Studium
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Mohammad H. Keshavarz, Thomas M. Klapötke

The Properties of
Energetic
Materials
|
Sensitivity, Physical and Thermodynamic Properties

2nd edition
Authors
Prof. Dr. Mohammad H. Keshavarz Prof. Dr. Thomas M. Klapötke
Malek-ashtar University of Technology Ludwig-Maximilians-Universität
Department of Chemistry Department of Chemistry/
83145 115 Shahin-shahr Energetic Materials Research
Iran Butenandstr. 5-13
[email protected] 81377 Munich
Germany
[email protected]

ISBN 978-3-11-074012-7
e-ISBN (PDF) 978-3-11-074015-8
e-ISBN (EPUB) 978-3-11-074024-0

Library of Congress Control Number: 2021941395

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.

© 2021 Walter de Gruyter GmbH, Berlin/Boston

Cover image: Jag_cz / iStock / Getty Images Plus
Typesetting: VTeX UAB, Lithuania
Printing and binding: CPI books GmbH, Leck

www.degruyter.com
Preface
For a chemist who is concerned with the synthesis of new energetic compounds, it is
essential to be able to assess physical and thermodynamic properties, as well as the
sensitivity of possible new energetic compounds before synthesis is attempted. Vari-
ous approaches have been developed to predict important aspects of the physical and
thermodynamic properties of energetic materials including (but not exclusively): crys-
tal density, heat of formation, melting point, enthalpy of fusion and enthalpy of sub-
limation of an organic energetic compound. Since an organic energetic material con-
sists of metastable molecules capable of undergoing very rapid and highly exothermic
reactions, many methods have been developed to estimate the sensitivity of an ener-
getic compound with respect to detonation-causing external stimuli such as heat, fric-
tion, impact, shock, and electrostatic discharge. This book introduces these methods
and demonstrates those methods which can be easily applied.

https://doi.org/10.1515/9783110740158-201
Preface to the second edition
Everything said in the preface to the first edition still holds and essentially does not
need any addition or correction. In this revised second edition, we have updated the
manuscript and added some recent aspects of energetic materials:
1. Some errors which unfortunately occurred in the first edition have been corrected
and the references have been updated where appropriate.
2. Recent works have been reviewed and discussed in each chapter. Moreover, new
sections have been inserted including:
(a) Chapter 1 – The use of group additivity methods for prediction of crystal den-
sity of energetic neutral and ionic liquids or salts
(b) Chapter 2 – The condensed phase heat of formation of energetic ionic liquids
and salts
(c) Chapter 3 – Melting points of ionic liquids
(d) Chapter 4 – Group additivity method for prediction of enthalpy and entropy
of fusion
(e) Chapter 5 – Group additivity method for prediction of the heat of sublimation
(f) Chapter 6 – Impact sensitivity of quaternary ammonium-based energetic
ionic liquids or salts
(g) Chapter 7 – Simple prediction of electrostatic spark sensitivity based on the
new ESZ KTTV instrument
(h) Chapter 8 – Critical diameter of solid pure and composite high explosives
(i) Chapter 9 – Friction sensitivity of quaternary ammonium-based energetic
ionic liquids
(j) Chapter 10 – Thermal stability of selected classes of energetic ionic liquids
and salts
(k) Chapter 11 – A general correlation between electric spark sensitivity and im-
pact sensitivity of nitroaromatics and nitramines as well as the relationship
between shock sensitivity of nitramine energetic compounds based on small-
scale gap test and their electric spark sensitivity

Mohammad Hossein Keshavarz

Thomas M. Klapötke

https://doi.org/10.1515/9783110740158-202
About the authors
Mohammad Hossein Keshavarz

Mohammad Hossein Keshavarz born in 1966, studied chemistry at Shiraz University and received
his BSc in 1988. He also received a MSc and PhD at Shiraz University in 1991 and 1995. From 1997
until 2008, he was Assistant Professor, Associate Professor and Professor of Physical Chemistry
at the University of Malek-ashtar in Shahin-shahr of Iran. Since 1997 he is Lecturer and researcher
at the Malek-ashtar University of Technology, Iran. He is the editor of two research journals in the
Persian language. Keshavarz has published over 400 scientific papers in international peer reviewed
journals, 5 book chapters and eight books in the field of the assessment of energetic materials (four
books in Persian language and four books in English language.

Thomas M. Klapötke

Thomas M. Klapötke received his PhD in 1986 (TU Berlin), post-doc in Fredericton, New Brunswick,
habilitation in 1990 (TU Berlin). From 1995 until 1997 Klapötke was Ramsay Professor of Chemistry
at the University of Glasgow in Scotland. Since 1997 he has held the Chair of Inorganic Chemistry at
LMU Munich. In 2009 Klapötke was appointed a Visiting Professor at CECD, University of Maryland
and in 2014 he was appointed a Adjunct Professor at the University of Rhode Island. Klapötke is a
Fellow of the RSC (C. Sci., C. Chem. F. R. S. C.), a member of the ACS and the Fluorine Division of the
ACS, a member of the GDCh, and a Life Member of both the IPS and the National Defense Industrial
Association. Most of Klapötke’s scientific collaborations are between LMU and ARL (US Army Re-
search Laboratory) in Aberdeen, MD and ARDEC (Armament Research Development and Engineering
Center) in Picatinny, NJ. Klapötke also collaborates with ERDC in Champaign, IL. And Prof Ang, How-
Ghee (NTU, Singapore). He is the executive editor of the Journal of Engineering Science and Military
Technologies, the Subject Editor in the area of explosives synthesis of the Central European Journal
of Energetic Materials and an editorial board member of Propellants, Explosives and Pyrotechnics
(PEP), Journal of Energetic Materials, the Chinese Journal of Explosives and Propellants and the In-
ternational Journal of Energetic Materials and Chemical Propulsion (IJEMCP). Klapötke has published
over 850 papers, 33 book chapters and 17 books.

https://doi.org/10.1515/9783110740158-203
Contents
Preface | V

Preface to the second edition | VII

About the authors | IX

1 Crystal density | 1
1.1 Group additivity method | 3
1.1.1 The method of atomic contributions | 7
1.1.2 Benzene-derived energetic compounds using atomic volumes | 8
1.1.3 The method of group additivity for estimating densities of energetic
ionic liquids and salts | 9
1.2 Quantum mechanical approach | 11
1.2.1 Quantum mechanical approach for neutral energetic compounds | 11
1.2.2 Energetic ionic liquids and salts as room temperature energetic
materials | 13
1.3 Empirical methods for the calculation of the crystal density
of different classes of energetic materials | 14
1.3.1 Nitroaromatic energetic compounds | 14
1.3.2 Acyclic and cyclic nitramines, nitrate esters and nitroaliphatic
compounds | 16
1.3.3 Improved method for the prediction of the crystal densities
of nitroaliphatics, nitrate esters and nitramines | 18
1.3.4 Reliable correlation for the prediction of the crystal densities
of polynitro arenes and polynitro heteroarenes | 19
1.3.5 The extended correlation for the prediction of the crystal density
of energetic compounds | 20
1.3.6 Energetic azido compounds | 22
1.4 Empirical methods for the assessment of the crystal density
of hazardous ionic molecular energetic materials using the
molecular structures | 24
1.4.1 Two general empirical methods | 24
1.4.2 The effects of various substituents on the density of tetrazolium nitrate
salts | 25
1.4.3 Predicting the density of tetrazole–N-oxide salts | 26
1.5 Summary | 27

2 Heat of formation | 29
2.1 Condensed and gas phase heats of formation
of energetic compounds | 29
XII | Contents

2.1.1 QM, MM and group additivity approaches | 30

2.1.2 Empirical approaches or QSPR methods on the basis
of structural parameters | 33
2.2 Energetic compounds with high nitrogen contents | 40
2.2.1 Using the molecular structure | 45
2.2.2 Gas phase information | 46
2.3 The condensed phase heat of formation of energetic ionic liquids and
salts | 47
2.3.1 Complex approach | 47
2.3.2 QSPR methods | 48
2.4 Summary | 52

3 Melting point | 53
3.1 Group additivity, QSPR and quantum mechanical methods | 54
3.2 Simple empirical methods on the basis of molecular structure | 55
3.2.1 Nitroaromatic compounds | 56
3.2.2 Polynitro arene and polynitro heteroarene compounds | 57
3.2.3 Nitramines, nitrate esters, nitrate salts and nitroaliphatics | 59
3.2.4 Nonaromatic energetic compounds | 59
3.2.5 Improved method for predicting the melting points of energetic
compounds | 60
3.2.6 Organic molecules containing hazardous peroxide groups | 64
3.2.7 Organic azides | 65
3.2.8 General method for the prediction of melting points of energetic
compounds including organic peroxides, organic azides, organic
nitrates, polynitro arenes, polynitro heteroarenes, acyclic and cyclic
nitramines, nitrate esters and nitroaliphatic compounds | 67
3.2.9 Cyclic saturated and unsaturated hydrocarbons | 74
3.3 Melting points of ionic liquids | 77
3.3.1 Group additivity approach | 78
3.3.2 QSPR approaches based on complex descriptors | 80
3.3.3 Simple approach based on the structure of cations and anions | 80
3.4 Summary | 81

4 Enthalpy and entropy of fusion | 85

4.1 Different approaches for the prediction of the enthalpy of fusion | 85
4.1.1 Group additivity method for prediction of the enthalpy of fusion | 86
4.1.2 Nitroaromatic carbocyclic energetic compounds | 87
4.1.3 Nitroaromatic energetic compounds | 88
4.1.4 Nonaromatic energetic compounds containing nitramine, nitrate
and nitro functional groups | 90
 Contents | XIII

4.1.5 Improved method for the reliable prediction of the enthalpy of fusion
of energetic compounds | 91
4.1.6 A reliable method to predict the enthalpy of fusion of energetic
materials | 94
4.2 Different methods to predict the entropy of fusion | 95
4.3 Summary | 103

5 Heat of sublimation | 105

5.1 Group additivity method for prediction of the heat of
sublimation | 106
5.2 Quantum mechanical and complex approaches for predicting
the heat of sublimation | 113
5.3 The use of structural parameters | 114
5.3.1 Nitroaromatic compounds | 114
5.3.2 Nitramines | 115
5.3.3 Nitroaromatics, nitramines, nitroaliphatics and nitrate esters | 116
5.3.4 General method for polynitro arenes, polynitro heteroarenes, acyclic
and cyclic nitramines, nitrate esters, nitroaliphatics, cyclic and acyclic
peroxides, as well as nitrogen-rich compounds | 117
5.4 Summary | 119

6 Impact sensitivity | 121

6.1 Complex methods | 122
6.2 Simple methods on the basis of molecular structure for neutral
energetic compounds | 124
6.2.1 Oxygen balance correlations | 125
6.2.2 Elemental composition and molecular moieties | 125
6.3 Impact sensitivity of quaternary ammonium-based energetic ionic
liquids or salts | 136
6.4 Summary | 137

7 Electric spark sensitivity | 141

7.1 Measurement of electric spark sensitivity | 141
7.2 Different methods for predicting electric spark sensitivity | 142
7.3 Simple methods for predicting electrostatic spark sensitivity based on
the RDAD instrument | 143
7.3.1 Polynitroaromatic compounds | 143
7.3.2 Cyclic and acyclic nitramines | 144
7.3.3 General correlation for polynitroaromatics as well as cyclic
and acyclic nitramines | 144
7.4 Simple prediction of electrostatic spark sensitivity based on the new
ESZ KTTV instrument | 145
XIV | Contents

7.4.1 Polynitro arenes based on ESZ KTTV | 146

7.4.2 Nitramines based on ESZ KTTV | 148
7.4.3 Quaternary ammonium-based energetic ionic liquids or salts based on
ESZ KTTV | 149
7.5 Some aspects of predictive methods | 151
7.6 Summary | 151

8 Shock sensitivity | 153

8.1 Small-scale gap test | 153
8.2 Large-scale gap test | 155
8.3 Critical diameter of solid pure and composite high explosives | 156
8.4 Summary | 159

9 Friction sensitivity | 161

9.1 Friction sensitivity of nitramines | 161
9.2 Friction sensitivity of quaternary ammonium-based energetic ionic
liquids | 162
9.3 Summary | 164

10 Heat sensitivity | 165

10.1 Thermal kinetics correlations | 166
10.1.1 Nitroparrafins | 167
10.1.2 Nitramines | 167
10.1.3 Polynitro arenes | 168
10.1.4 Organic energetic compounds | 169
10.2 Heat of decomposition and temperature
of thermal decomposition | 171
10.2.1 Heat of decomposition of nitroaromatics | 171
10.2.2 Heats of decomposition of organic peroxides | 173
10.2.3 Onset temperature of polynitro arenes and organic peroxides as well as
maximum loss temperature of organic azides | 174
10.3 Deflagration temperature | 177
10.3.1 Fnonadd
+
| 178
10.3.2 Fnonadd | 178
−

10.3.3 Energetic compounds containing both Fnonadd

+
and Fnonadd
−
| 179
10.4 Thermal stability of selected classes of energetic ionic liquids and
salts | 179
10.4.1 Predicting activation energy of thermolysis of some selected ionic
liquids | 180
10.4.2 Decomposition temperature of imidazolium-based energetic ionic
liquids or salts | 181
 Contents | XV

10.5 Decomposition temperature of azole-based energetic

compounds | 185
10.6 Summary | 186

11 Relationships between different sensitivities | 189

11.1 Relationship between impact sensitivity of energetic compounds and
activation energies of thermal decomposition | 189
11.1.1 Nitroaromatics | 190
11.1.2 Nitramines | 190
11.2 Relationship between electric spark sensitivity and impact sensitivity of
nitroaromatics | 191
11.3 A general correlation between electric spark sensitivity and impact
sensitivity of nitroaromatics and nitramines | 192
11.4 Relationship between electric spark sensitivity and activation energy of
the thermal decomposition of nitramines | 193
11.5 Correlation of the electrostatic sensitivity and activation energies for the
thermal decomposition of nitroaromatics | 194
11.6 Relationship between the activation energy of thermolysis and friction
sensitivity of cyclic and acyclic nitramines | 195
11.7 Relationship between shock sensitivity of nitramine energetic
compounds based on small-scale gap test and their electric spark
sensitivity | 196
11.8 Summary | 198

Problems | 199

Answers to Problems | 209

List of symbols | 213

A Glossary of compound names and heats of formation for pure as well as

composite explosives | 225

B Calculation of the gas phase standard enthalpies of formation | 229

C Glossary of compound names as well as the measured and calculated values

of the condensed phase heats of formation for some energetic ionic liquids
and salts | 237

Bibliography | 241

Index | 267
1 Crystal density
Crystal density 1–27
Empirical methods 14
– Acyclic and cyclic nitramines, nitrate esters and nitroaliphatic compounds 16
– Energetic azido compounds 22
– Energetic compounds 20
– Nitroaromatic energetic compounds 14
– Polynitro arenes and polynitro heteroarenes 19
Group additivity method 3
– Atomic contributions 7
– Benzene-derived energetic compounds using atomic volumes 8
– Energetic ionic liquids and salts 9
Ionic molecular energetic materials 24
– Tetrazole–N-oxide salts 26
– Tetrazolium nitrate salts 25
Quantum mechanical approach 11
– Energetic ionic liquids and salts as room temperature energetic materials 13

Organic compounds containing energetic groups such as nitro, nitramine, and nitrate
ester functional groups have wide applications in military and civilian applications
as propellants, explosives, and pyrotechnics because they can release their stored
chemical energy upon external stimuli such as heat, impact, shock, friction, and
electrostatic discharge [1–7]. Ionic molecular energetic materials containing high
nitrogen content are attractive for scientists and industries. They may be used as
energetic compounds because they have high density, positive heats of formation,
and thermal stability [8]. They frequently consist of high nitrogen content cations
such as substituted imidazole, triazole, and tetrazole derivatives and bulky anions
containing energetic groups, e. g. –NO2 , –N3 , and –CN. They can be considered as
eco-friendly, low-melting, and thermally stable ionic compounds [2]. Considerable
efforts have been done in recent years to introduce new organic and ionic molecular
energetic materials with high density because their higher density is always desirable
for packing more energy per unit volume.
The crystal density and condensed phase heat of formation of an energetic com-
pound are two important physicothermal properties, and are essential values in order
to be able predict the detonation performance using a thermodynamic equilibrium
code such as CHEETAH [9], or through empirical methods [1, 10–17]. The perfor-
mance characteristics of energetic compounds are proportional to their densities,
e. g. the Chapman–Jouguet pressure is proportional to the square of the initial den-
sity [1, 10]. Thus, it is essential to use suitable methods such as gas pycnometry or
low-temperature single crystal x-ray diffraction to determine the crystal density of
an energetic compound. New molecules which are candidates for possible use as
energetic materials can be synthesized, characterized, and formulated by reliable
predictive methods, and theoretical molecular design may be used to develop new

https://doi.org/10.1515/9783110740158-001
2 | 1 Crystal density

energetic materials before synthesis is attempted. The synthesis of molecules with

significantly increased energy in comparison with current materials, as well as the
synthesis of very insensitive materials which have reasonable energies, have been
two important goals for scientists in recent years. Since it is essential to have reliable
methods to predict the density of energetic compounds, different approaches have
been developed to assess the crystal density of an energetic compound at 25 °C.
Attempts have been made to predict the crystal densities of proposed new ener-
getic compounds with satisfactory accuracy. A predicted crystal density that differs
by less than 0.03 g/cm3 from the experimentally obtained value should be defined
as “excellent”. A value that deviates between 0.03 and 0.05 g/cm3 from the experi-
mental value is still “informative” [18]. Quantum-mechanically determined molecu-
lar volumes [19–22], group additivity [23–25], empirical methods [26–29], quantitative
structure–property relationships (QSPR) based on complex descriptors [30, 31] and
molecular dynamics (MD) [32] are usual different approaches which have developed to
predict the crystal densities of different types of Ca Hb Nc Od energetic compounds. The
group additivity method is a simple approach because it requires only a set of atoms
and group volumes that can be summed to obtain an estimate of the effective molecu-
lar volume using a simple computer code [24]. Tedious investigations have been under-
taken over the last 30 years or so to expand the list of atom and functional group vol-
umes [24, 25]. Although group additivity methods are simple to use with low cost, the
predicted value which is obtained may show very large deviation from the experitmen-
tally obtained value for some energetic compounds. Moreover, such methods can only
be used for those energetic compounds for which the values of all groups contained in
the compound have been specified. Quantum mechanical and empirical methods (or
QSPR) based on the structures of energetic compounds are more reliable approaches
to estimate the density of an energetic compound. The QSPR methods are based on
complex descriptors which develop a mathematical relationship connecting a macro-
scopic property of a series of compounds to microscopic descriptors derived from their
molecular structures using an experimental data set. They require computer codes
and expert users, as well as complex descriptors. The descriptors used in QSPR models
can be empirical, or computed on the basis of the molecular structure. Various statis-
tical tools including multilinear regression (MLR), nonlinear regression (NLR), partial
least squares (PLS), artificial neural network (ANN), genetic algorithm (GA) or support
vector machine (SVM) are frequently used to derive the mathematical equations (or al-
gorithms) linking the property and descriptors [33, 34]. MD is a computer simulation of
the physical movements of atoms and molecules in the context of N-body simulation.
Due to the higher reliability of quantum mechanical and empirical methods (or QSPR)
based on molecular/ionic structures, these approaches have been developed in recent
years for neutral and ionic liquid energetic compounds, which are described in this
chapter. Some efforts have been made to assess the detonation performance of newly
designed explosives and ionic molecular energetic materials with high detonation per-
formance in recent years [13, 15, 35–46]. Since high reliability is an important param-
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