Green Solvents, Volume 6 Ionic Liquids

by Anastas, Paul T.; Wasserscheid, Peter; Stark, Annegret

• ISBN13: 9783527325924
• ISBN10: 3527325921
• Edition: 1st
• Format: Hardcover
• Copyright: 2013-09-30
• Publisher: Wiley-VCH

Summary

The shift towards being as environmentally-friendly as possible has resulted in the need for this important volume on the role of ionic liquids in green chemistry. Edited by Peter Wasserscheid, one of the pioneers of ionic liquid research, and Annegret Stark, this is an essential resource for anyone wishing to gain an understanding of the world of green chemistry, as well as for chemists, environmental agencies and chemical engineers.

Author Biography

Paul T. Anastas joined Yale University as Professor and iserves as the Director of the Center for Green Chemistry and Green Engineering at Yale. From 2004-2006, Paul Anastas has been the Director of the Green Chemistry Institute in Washington, D.C. Until June of 2004 he served as Assistant Director for Environment at e White House Office of Science and Technology Policy where his responsibilities included a wide range of environmental science issues including furthering international public-private cooperation in areas of Science for Sustainability such as Green Chemistry. In 1991, he established the industry-government-university partnership Green Chemistry Program, which was expanded to include basic research, and the Presidential Green Chemistry Challenge Awards. He has published and edited several books in the field of Green Chemistry and developed the 12 principles of Green Chemistry.

Table of Contents

Ionic Liquids and Green Chemistry – an Extended Preface XIII

About the Editors XXI

List of Contributors XXIII

Part I Green Synthesis 1

1 The Green Synthesis of Ionic Liquids 3
Maggel Deetlefs and Kenneth R. Seddon

1.1 The Status Quo of Green Ionic Liquid Syntheses 3

1.2 Ionic Liquid Preparations Evaluated for Greenness 4

1.3 Which Principles of Green Chemistry are Relevant to Ionic Liquid Preparations? 6

1.4 Atom Economy and the E-factor 7

1.5 Strengths, Weaknesses, Opportunities, Threats (SWOT) Analyses 8

1.6 Conductive Heating Preparation of 1-Alkyl-3-methylimidazolium Halide Salts 8

1.7 Purification of 1-Alkyl-3-methylimidazolium Halide Salts 12

1.8 Ionic Liquid Syntheses Promoted by Microwave Irradiation 15

1.9 Syntheses of Ionic Liquids Promoted by Ultrasonic Irradiation 20

1.10 Simultaneous Use of Microwave and Ultrasonic Irradiation to Prepare Ionic Liquids 23

1.11 Preparation of Ionic Liquids Using Microreactors 25

1.12 Purification of Ionic Liquids with Non-halide Anions 28

1.13 Decolorization of Ionic Liquids 31

1.14 Conclusion 34

References 36

Part II Green Synthesis Using Ionic Liquids 39

2 Green Organic Synthesis in Ionic Liquids 41
Peter Wasserscheid and Joni Joni

2.1 General Aspects 41

2.2 Friedel–Crafts Alkylation 54

References 59

3 Transition Metal Catalysis in Ionic Liquids 65
Peter Wasserscheid

3.1 Solubility and Immobilization of Transition Metal Complexes in Ionic Liquids 65

3.2 Ionic Liquid–Catalyst Interaction 67

3.3 Distillative Product Isolation from Ionic Catalyst Solutions 70

3.4 New Opportunities for Biphasic Catalysis 72

3.5 Green Aspects of Nanoparticle and Nanocluster Catalysis in Ionic Liquids 75

3.6 Green Aspects of Heterogeneous Catalysis in Ionic Liquids 77

3.7 Green Chemistry Aspects of Hydroformylation Catalysis in Ionic Liquids 79

3.8 Conclusion 85

References 85

4 Ionic Liquids in the Manufacture of 5-Hydroxymethylfurfural from Saccharides. An Example of the Conversion of Renewable Resources to Platform Chemicals 93
Annegret Stark and Bernd Ondruschka

4.1 Introduction 93

4.2 HMF Manufacture 99

4.3 Goals of Study 105

4.4 HMF Manufacture in Ionic Liquids – Results of Detailed Studies in the Jena Laboratories 105

4.5 Conclusion 117

References 118

5 Cellulose Dissolution and Processing with Ionic Liquids 123
Uwe Vagt

5.1 General Aspects 123

5.2 Dissolution of Cellulose in Ionic Liquids 127

5.3 Rheological Behavior of Cellulose Solutions in Ionic Liquids 129

5.4 Regeneration of the Cellulose and Recycling of the Ionic Liquid 131

5.5 Cellulosic Fibers 131

5.6 Cellulose Derivatives 134

5.7 Fractionation of Biomass with Ionic Liquids 134

5.8 Conclusion and Outlook 135

References 135

Part III Ionic Liquids in Green Engineering 137

6 Green Separation Processes with Ionic Liquids 139
Wytze (G. W.) Meindersma, Ferdy (S. A. F.) Onink, and André B. de Haan

6.1 Introduction 139

6.2 Liquid Separations 141

6.3 Environmental Separations 158

6.4 Combination of Separations in the Liquid Phase with Membranes 163

6.5 Gas Separations 164

6.6 Engineering Aspects 168

6.7 Design of a Separation Process 172

6.8 Conclusions 175

References 176

7 Applications of Ionic Liquids in Electrolyte Systems 191
William R. Pitner, Peer Kirsch, Kentaro Kawata, and Hiromi Shinohara

7.1 Introduction 191

7.2 Electrolyte Properties of Ionic Liquids 193

7.3 Electrochemical Stability 196

7.4 Dye-sensitized Solar Cells 198

References 200

8 Ionic Liquids as Lubricants 203
Marc Uerdingen

8.1 Introduction 203

8.2 Why Are Ionic Liquids Good Lubricants? 204

8.3 Applications, Conclusion and Future Challenges 217

References 218

9 New Working Pairs for Absorption Chillers 221
Matthias Seiler and Peter Schwab

9.1 Introduction 221

9.2 Absorption Chillers 222

9.3 Requirements and Challenges 223

9.4 State of the Art and Selected Results 226

9.5 Abbreviations 228

References 228

Part IV Ionic Liquids and the Environment 233

10 Design of Inherently Safer Ionic Liquids: Toxicology and Biodegradation 235
Marianne Matzke, Jürgen Arning, Johannes Ranke, Bernd Jastorff, and Stefan Stolte

10.1 Introduction 235

10.2 (Eco)toxicity of Ionic Liquids 239

10.3 Biodegradability of Ionic Liquids 265

10.4 Conclusion 290

References 295

11 Eco-efficiency Analysis of an Industrially Implemented Ionic Liquid-based Process – the BASF BASIL Process 299
Peter Saling, Matthias Maase, and Uwe Vagt

11.1 The Eco-efficiency Analysis Tool 299

11.2 The Methodological Approach 299

11.3 The Design of the Eco-efficiency Study of BASIL 303

11.4 Selected Single Results 304

11.5 The Creation of the Eco-efficiency Portfolio 309

11.6 Scenario Analysis 311

11.7 Conclusion 312

11.8 Outlook 313

References 314

12 Perspectives of Ionic Liquids as Environmentally Benign Substitutes for Molecular Solvents 315
Denise Ott, Dana Kralisch, and Annegret Stark

12.1 Introduction 315

12.2 Evaluation and Optimization of R&D Processes: Developing a Methodology 317

12.3 Assessment of Ionic Liquid Synthesis – Case Studies 322

12.4 Assessment of the Application of Ionic Liquids in Contrast to Molecular Solvents 329

12.5 Conclusions 335

References 336

Index 341