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2nd Edition
Alternative Solvents for Green Chemistry
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RSC Green Chemistry

Series Editors:
James H Clark, Department of Chemistry, University of York, UK
George A Kraus, Department of Chemistry, Iowa State University, Ames, Iowa,
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USA
Andrzej Stankiewicz, Delft University of Technology, The Netherlands
Peter Siedl, Federal University of Rio de Janeiro, Brazil
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Titles in the Series:

1: The Future of Glycerol: New Uses of a Versatile Raw Material
2: Alternative Solvents for Green Chemistry
3: Eco-Friendly Synthesis of Fine Chemicals
4: Sustainable Solutions for Modern Economies
5: Chemical Reactions and Processes under Flow Conditions
6: Radical Reactions in Aqueous Media
7: Aqueous Microwave Chemistry
8: The Future of Glycerol: 2nd Edition
9: Transportation Biofuels: Novel Pathways for the Production of Ethanol,
Biogas and Biodiesel
10: Alternatives to Conventional Food Processing
11: Green Trends in Insect Control
12: A Handbook of Applied Biopolymer Technology: Synthesis, Degradation
and Applications
13: Challenges in Green Analytical Chemistry
14: Advanced Oil Crop Biorefineries
15: Enantioselective Homogeneous Supported Catalysis
16: Natural Polymers Volume 1: Composites
.

17: Natural Polymers Volume 2: Nanocomposites

18: Integrated Forest Biorefineries
19: Sustainable Preparation of Metal Nanoparticles: Methods and Applications
20: Alternative Solvents for Green Chemistry: 2nd Edition

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Alternative Solvents for Green Chemistry

2nd Edition
Francesca M Kerton
Published on 31 January 2013 on http://pubs.rsc.org | doi:10.1039/9781849736824-FP001

Department of Chemistry, Memorial University of Newfoundland, St John’s,

Newfoundland, Canada
Email: [email protected]

Ray Marriott
University of Bangor, Bangor, Gwynedd, UK
Email: [email protected]
.
Published on 31 January 2013 on http://pubs.rsc.org | doi:10.1039/9781849736824-FP001 View Online

RSC Green Chemistry No. 20

ISBN: 978-1-84973-595-7
ISSN: 1757-7039

A catalogue record for this book is available from the British Library

# FM Kerton and R Marriott 2013

All rights reserved

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or for private study, criticism or review, as permitted under the Copyright,
.

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Published on 31 January 2013 on http://pubs.rsc.org | doi:10.1039/9781849736824-FP005

Preface

Everyone is becoming more environmentally conscious and therefore, chemical

processes are being developed with their environmental burden in mind. Of
course, this also means that more traditional chemical methods are being
replaced with new innovations. This includes new solvents.
Solvents are everywhere, but should they be? They are used in most areas
including synthetic chemistry, analytical chemistry, pharmaceutical production
and processing, the food and flavour industry and the materials and coatings
sectors. But, the principles of green chemistry guide us to use less of them,
or to use safer, more environmentally friendly solvents if they are essential.
Therefore, we should always ask ourselves, do we really need a solvent?
Chapter 3 explains some of the challenges and successes in the field of solvent-
free chemistry, and the answer becomes apparent: not always!
In the introductory chapter, some of the hazards of conventional solvents
.

(e.g. toxicity and flammability) and their significant contribution to waste

streams are highlighted. The general properties of solvents and why and where
they are used are outlined. Additionally, EHS (Environmental, Health and
Safety) assessments and life-cycle analyses for traditional and alternative
solvents are described. It becomes clear that often a less-hazardous VOC is
available and that although only ‘light green’ (or at least ‘less black’) in colour,
they can be used as an interim measure until a more satisfying option becomes
available. In each of the subsequent chapters, where possible, the use of an
alternative solvent is described for a range of chemical applications including
extractions, synthetic and materials chemistry. At the beginning of each of
these chapters, some of the advantages and disadvantages of that medium are
laid out.
Water is often described as Nature’s solvent; therefore Chapter 4 describes
the solvent properties of water. It is already used quite widely on an industrial

RSC Green Chemistry No. 20

Alternative Solvents for Green Chemistry: 2nd Edition
By Francesca M Kerton and Ray Marriott
# FM Kerton and R Marriott 2013
Published by the Royal Society of Chemistry, www.rsc.org

v
 View Online

vi Preface

scale, particularly in emulsion polymerisation processes and hydrodistillations.

However, some of the most exciting results have come in the field of synthetic
chemistry. Recently, ‘on-water’ reactions have shown that hydrophobic
(water-insoluble) compounds can achieve higher rates dispersed in water
compared to reactions in conventional solvents or under solvent free
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conditions. Water can also be used at very high temperatures and under
pressure in a near-critical or supercritical state. Under these conditions, its
properties are significantly altered and unusual chemistry can result. This is
further discussed in Chapter 5, which describes supercritical fluids. The focus
here is on the nonflammable options, that is, carbon dioxide and water.
Modifications that are performed on substrates in order to make them soluble
in supercritical carbon dioxide are outlined. Additionally, the benefits of the
poor solvating power of carbon dioxide, e.g. selective extractions, are
highlighted and its use in tuning reactivity through its variable density is
described.
In addition to water and carbon dioxide, there is an increasing availability of
solvents sourced from renewable feedstocks including ethanol, ethyl lactate
and 2-methyl-tetrahydrofuran. The properties of these solvents and their
potential as replacements to petroleum-sourced solvents are discussed in
Chapter 6. Renewable feedstocks and their transformations are a growing area
of green chemistry and they have significantly impacted the solvent choice
arena. In addition to renewable VOC solvents, nonvolatile ionic liquid and
eutectic mixture solvents have been prepared from renewable feedstocks
and are looking to be very promising alternatives in terms of toxicity and
degradation. These and other room-temperature ionic liquids (RTILs) are
.

discussed in Chapter 7. The field of RTILs has grown dramatically in the last
ten years and the range of anions/cations that can be used to make these
nonvolatile solvents is continually expanding. Although some of these media
may be more expensive than other alternatives, the chance to make task-
specific solvents for particular processes is very exciting. RTILs, alongside
fluorous solvents, have also made a large impact in the area of recyclable
homogeneous catalysts. Fluorous solvents, as described in Chapter 8, show
interesting phase behaviour and allow the benefits of a heterogeneous and
homogeneous system to be employed by adjusting an external variable such as
temperature. Recent advances in this area will be discussed, for example,
supported fluorous chemistry, which avoids the use of large amounts of
fluorous solvents and might be more amenable to industrial scale processes.
Possibly the least explored and newest options available to the green chemist
are liquid polymer solvents (Chapter 9) and switchable and tunable solvents
(Chapter 10). Unreactive low molecular weight polymers or those with low
glass transition temperatures can be used as nonvolatile solvents. In particular,
poly(ethyleneglycols) and poly(propyleneglycols) have been used recently in a
range of applications. Probably the most important recent additions to our
toolbox are switchable solvents. New molecular solvents have been discovered
that can be switched from nonvolatile to volatile or between polar and
 View Online

Preface vii

nonpolar environments by the application of an external stimulus. Gas-

expanded liquids will also be discussed in Chapter 10, as carbon dioxide can be
used as a solubility switch and to reduce the environmental burden of
conventional solvents.
Unfortunately, as will become clear to readers, there is no universal green
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solvent and users must ascertain their best options based on prior chemistry,
cost, environmental benefits and other factors. It is important to try and
minimise the number of solvent changes in a chemical process and therefore,
the importance of solvents in product purification, extraction and separation
technologies has been highlighted.
There have been many in-depth books and reviews published in the area of
green solvents. Hopefully, readers will find this book a readable introduction
to the field. However, some cutting-edge results from the recent literature have
been included in an attempt to give a clearer picture of where green solvents
are today. For more comprehensive information on a particular solvent
system, readers should look to the primary literature and the many excellent
reviews of relevance to this field in journals such as Green Chemistry and
Chemical Reviews.
Certain solvent media can be fascinating in their own right, not just as
‘green’ solvent alternatives! Therefore, we must not be blind to our overall goal
in reducing the environmental burden of a particular process. Hopefully,
readers of this book will be able to make up their own minds about the vast
array of solvents available for a greener process, or even come up with a new
addition for the green chemistry toolbox. Although many advances have been
made during the past decade, the most exciting results are surely yet to come.
.

I would like to thank the editors of the RSC Green Chemistry Series, James
Clark and George Kraus, for the opportunity to contribute to this important
group of books. Also, I would like to acknowledge Merlin Fox (the
commissioning editor) and the staff at RSC Publishing involved with this
series, particularly, Annie Jacob, who has been advising and helping me all
along the way. Finally, I would like to thank my husband, Chris Kozak, for his
patience, support and motivational input during the writing of this book.
Francesca Kerton
St. John’s, Newfoundland, Canada
1st Edition, June 2008
Since publication of the first edition, research in the field of greener solvents
has continued at a pace, with special issues dedicated to field being published
in several journals (for example, issue 6 of Green Chemistry in 2012). I am
happy to welcome a co-author to this edition. Ray has applied his experience in
an industrial setting to overhaul the chapter on industrial applications
(Chapter 11) and provides a new chapter on legislation in this area (Chapter 2).
All chapters have received some updating – some more than others. Switchable
solvents were relatively new phenomena when the first edition was published
and discoveries in this field have grown significantly. I thank Prof. Philip
Jessop for tips in this area. Also, RTIL based research has continued to grow
 View Online

viii Preface
exponentially, and significant research in the use of alternative solvents in
biomass transformations and biocatalysis has been published. More detailed
toxicological studies have been performed on RTILs and applications of
bioderived solvents have become more wide spread. A new chapter on the use
of green solvents in education and solvent awareness for the general public has
Published on 31 January 2013 on http://pubs.rsc.org | doi:10.1039/9781849736824-FP005

been added (Chapter 12).

Finally, I would like to thank the editors and publishers of this book,
especially, Merlin Fox and Rosalind Searle for their patience. My husband,
family and research group are also thanked for their support while I revised the
book.
Francesca Kerton
St. John’s, Newfoundland, Canada
.
Published on 31 January 2013 on http://pubs.rsc.org | doi:10.1039/9781849736824-FP009

Contents
Chapter 1 Introduction 1

1.1 Introduction 1
1.2 Safety Considerations, Life-Cycle Assessment and
Green Metrics 3
1.2.1 Environmental, Health and Safety (EHS) 5
1.2.2 Life Cycle Assessment (LCA) 5
1.2.3 Solvents in the Pharmaceutical Industry and
Immediate Alternatives to Common
Laboratory Solvents 13
1.2.4 Solvents in Analytical Chemistry incl. HPLC 16
1.3 Solvent Properties including Polarity 18
1.4 What Remains to be Done? 24
1.5 Summary 27
.

References 28

Chapter 2 Green Solvents – Legislation and Certification 31

2.1 Introduction 31
2.2 Solvent Registration 32
2.2.1 European Union and Switzerland 32
2.2.2 United States and Canada 33
2.2.3 China and Taiwan 34
2.2.4 Japan 35
2.3 Solvent Emission Regulations 36
2.4 Applications Legislation 39
2.4.1 Food and Beverages 39

RSC Green Chemistry No. 20

Alternative Solvents for Green Chemistry: 2nd Edition
By Francesca M Kerton and Ray Marriott
# FM Kerton and R Marriott 2013
Published by the Royal Society of Chemistry, www.rsc.org

ix
 View Online

x Contents
2.4.2Pharmaceuticals, Nutraceuticals and Herbal
Medicines 41
2.4.3 Cosmetics and Personal Care 44
2.5 Natural or Organic Certification 45
2.6 Summary 47
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References 47

Chapter 3 ‘Solvent-Free’ Chemistry 51

3.1 Introduction 51
3.2 Chemical Examples 53
3.2.1 Inorganic and Materials Synthesis 53
3.2.2 Organic Synthesis 57
3.2.3 Biomass Transformations 72
3.3 Summary and Outlook for the Future 76
References 77

Chapter 4 Water 82

4.1 Introduction 82
4.1.1 Biphasic Systems 84
4.2 Chemical Examples 87
4.2.1 Extraction 87
4.2.2 Chemical Synthesis 88
.

4.2.3 Materials Synthesis 102

4.3 Energy-Related Research in Seawater: Biorefineries
and Hydrogen Production 106
4.4 High-Temperature, Superheated or Near-Critical
Water 108
4.5 Summary and Outlook for the Future 109
References 110

Chapter 5 Supercritical Fluids 115

5.1 Introduction 115

5.2 Chemical Examples 117
5.2.1 Supercritical and Liquid Carbon Dioxide 117
5.2.2 Supercritical Water and Near-Critical Water 132
5.2.3 Supercritical Alcohols 140
5.3 Summary and Outlook for the Future 141
References 142
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