Deep Eutectic Solvents

A useful guide to the fundamentals and applications of deep eutectic solvents Deep Eutectic Solvents contains a comprehensive review of the use of deep eutectic solvents (DESs) as an environmentally benign alternative reaction media for chemical transformations and processes. The contributors cover a range of topics including synthesis, structure, properties, toxicity and biodegradability of DESs. The book also explores myriad applications in various disciplines, such as organic synthesis and (bio)catalysis, electrochemistry, extraction, analytical chemistry, polymerizations, (nano)materials preparation, biomass processing, and gas adsorption. The book is aimed at organic chemists, catalytic chemists, pharmaceutical chemists, biochemists, electrochemists, and others involved in the design of eco-friendly reactions and processes. This important book: -Explores the promise of DESs as an environmentally benign alternative to hazardous organic solvents -Covers the synthesis, structure, properties (incl. toxicity) as well as a wide range of applications -Offers a springboard for stimulating critical discussion and encouraging further advances in the field Deep Eutectic Solvents is an interdisciplinary resource for researchers in academia and industry interested in the many uses of DESs as an environmentally benign alternative reaction media.

Auteur

*Diego J. Ram??n is full professor at the University of Alicante, Spain, since 2010. His current research interests lie in the eld of organometallic chemistry and asymmetric synthesis. **Gabriela Guillena is full professor and Head of the Department of Organic Chemistry at the University of Alicante, Spain. Her research is focused on new methodologies and asymmetric organocatalysis.*

Résumé
A useful guide to the fundamentals and applications of deep eutectic solvents

Deep Eutectic Solvents contains a comprehensive review of the use of deep eutectic solvents (DESs) as an environmentally benign alternative reaction media for chemical transformations and processes. The contributors cover a range of topics including synthesis, structure, properties, toxicity and biodegradability of DESs. The book also explores myriad applications in various disciplines, such as organic synthesis and (bio)catalysis, electrochemistry, extraction, analytical chemistry, polymerizations, (nano)materials preparation, biomass processing, and gas adsorption.

The book is aimed at organic chemists, catalytic chemists, pharmaceutical chemists, biochemists, electrochemists, and others involved in the design of eco-friendly reactions and processes. This important book:

-Explores the promise of DESs as an environmentally benign alternative to hazardous organic solvents
-Covers the synthesis, structure, properties (incl. toxicity) as well as a wide range of applications
-Offers a springboard for stimulating critical discussion and encouraging further advances in the field

Deep Eutectic Solvents is an interdisciplinary resource for researchers in academia and industry interested in the many uses of DESs as an environmentally benign alternative reaction media.

Contenu
Preface xiii

**1 Synthesis and Properties 1
**Karine De Oliveira Vigier and Francois Jerome

1.1 Introduction 1

1.2 Synthesis 2

1.3 Properties 4

1.3.1 Freezing Point (*T*f) 4

1.3.2 Density 5

1.3.3 Viscosity 11

1.3.4 Ionic Conductivity 16

1.3.5 Polarity 19

1.3.6 Surface Tension 19

1.4 Summary and Conclusions 21

References 21

**2 Structure and Implications 25
**Oliver S. Hammond and Karen J. Edler

2.1 Introduction 25

2.2 Nanostructure of DES 26

2.2.1 Complex Ion Model 26

2.2.2 An Extended Hydrogen Bond Network Model: Alphabet Soup 27

2.2.3 Noncholinium DES 36

2.3 Conclusions and Implications 38

Abbreviations 40

References 40

**3 Toxicity and Biodegradability of Deep Eutectic Solvents and Natural Deep Eutectic Solvents 43
**Zhen Yang

3.1 Introduction 43

3.2 Toxicity to Microorganisms 44

3.2.1 Toxicity to Bacteria 44

3.2.2 Toxicity to Other Microorganisms 47

3.3 Toxicity to Animals 48

3.3.1 In Vitro Toxicity Tests on Vertebrates and Invertebrates 48

3.3.2 Cytotoxicity 49

3.3.3 In Vivo Acute Toxicity Tests and Pharmacokinetics 53

3.4 Toxicity to Plants 55

3.5 Biodegradability 56

3.6 Summary and Conclusions 57

Abbreviations 58

References 59

**4 Natural Deep Eutectic Solvents: From Their Discovery to Their Applications 61
**Henni Vanda, Robert Verpoorte, Peter G. L. Klinkhamer, and Young H. Choi

4.1 Introduction 61

4.2 Natural Deep Eutectic Solvents is a Concept Based on How Physicochemical Features Could Be Used for Biological Functions 63

4.3 Extraction and Solubilization of NonwaterSoluble Metabolites 66

4.4 Solvents for Macromolecules 69

4.4.1 Application of ILs and DES to Macromolecules 69

4.4.2 Recent NADES Application for DNA, RNA, and Proteins 70

4.5 Application to Enzyme Reactions 75

4.6 Pharmaceutical Applications 76

4.7 Perspective of NADES 76

Abbreviations 79

References 79

**5 Hydrophobic Deep Eutectic Solvents 83
**Samah E.E. Warrag and Maaike C. Kroon

5.1 Introduction 83

5.2 Physiochemical Properties of Hydrophobic DESs 84

5.2.1 Density 85

5.2.2 Viscosity 86

5.3 Thermal Stability Window 86

5.4 Applications of Hydrophobic DESs 87

5.4.1 The Extraction of Fatty Acids and Biomolecules from Water 87

5.4.2 The Removal of Transition Metal Ions from Water 89

5.4.3 Impregnation in Membranes 90

5.4.4 The Removal of Pesticides from Water 90

5.4.5 CO2 Capture 90

5.5 Prediction of the Hydrophobic DESs Phase Behavior 91

5.5.1 The Use of PCSAFT 91

5.6 Outlook and Recommendations 92

Abbreviations 92

References 93

**6 Deep Eutectic Solvents: Exploring Their Role in Nature 95
**Rita Craveiro, Francisca Mano, Alexandre Paiva, and Ana Rita C. Duarte

6.1 (Introduction) DES in Nature 95

6.2 Honey 97

6.2.1 Behind Beehive: How Honey is Really Produced? 98

6.2.2 Honey and Its Properties 99

6.2.3 Honey as the First THEDES 99

6.3 Maple Syrup: How is Maple Syrup Produced? 100

6.3.1 Maple Syrup Nutraceutical Value 101

6.3.2 Maple Syrup and NADES 102

6.4 Sugar Beet 102

6.5 Resurrection Plants 106

6.6 Summary and Conclusions 107

Abbreviations 107

Acknowledgments 108

References 108 **7 Organic Synthesis in DESs 111
***Filippo M...