Aqueous Microwave Assisted Chemistry: Synthesis and Catalysis

Overview

The demands for green and sustainable synthetic methods in the fields of healthcare and fine chemicals, combined with the pressure to produce these substances expeditiously and in an environmentally benign fashion, pose significant challenges to the synthetic chemical community. Green chemistry can avoid pollution by utilizing techniques that are environmentally friendly by design and one of the best green techniques is the use of microwave (MW) assisted aqueous synthetic protocols. Fusing MW technique with water...

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Overview

The demands for green and sustainable synthetic methods in the fields of healthcare and fine chemicals, combined with the pressure to produce these substances expeditiously and in an environmentally benign fashion, pose significant challenges to the synthetic chemical community. Green chemistry can avoid pollution by utilizing techniques that are environmentally friendly by design and one of the best green techniques is the use of microwave (MW) assisted aqueous synthetic protocols. Fusing MW technique with water (as a benign reaction medium) can offer an extraordinary synergistic effect with greater potential than these two individual components in isolation. Selective microwave heating can be exploited to develop a high yield protocol and the use of water expedites the MW-protocol with more energy efficiency. This book provides an overview of the various processes developed using aqueous microwave chemistry and is written for chemists, chemical engineers and researchers in the early stages who want to develop sustainable and green processes. Written by well known microwave experts, the book is a comprehensive examination of the field and is the first book that deals strictly with aqueous microwave chemistry and represents a significant effort towards green chemistry. It covers all the microwave-assisted aqueous reactions in depth, including heterocycle synthesis, metal catalysis, enzyme catalysis, polymer synthesis, nanomaterials synthesis and nano-catalysis. Each chapter contains representative experimental procedures, helping the reader quickly replicate some of the experiments to gain hands-on experience.

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Editorial Reviews

From the Publisher
""Both (editors) are known for their work in the area of micorwave-assisted synthesis, and Varma is considered a prominent elder statesman of the field." "For someone interested in getting into the field....this book may well prove to have value for the money."
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Product Details

  • ISBN-13: 9781849730389
  • Publisher: Royal Society of Chemistry, The
  • Publication date: 5/28/2010
  • Series: RSC Green Chemistry Series , #7
  • Pages: 240
  • Product dimensions: 6.30 (w) x 9.30 (h) x 0.80 (d)

Meet the Author

Dr Vivek Polshettiwar was born in Mangli (India) in 1979. He obtained his Ph.D. (2005) under the supervision of Prof. M. P. Kaushik from Jiwaji University and DRDE, Gwalior. He investigated nanostructured silica-catalysis, with Prof. J. J. E. Moreau and Prof. P. Hesemann in 2006 during his postdoctoral research at ENSCM, Montpellier (France). He also worked as project leader in Jubilant Chemsys, Noida for short time.. Then he moved to the U. S. Environmental Protection Agency (2007-2009) to research nano-catalysis and MW-assisted new synthetic methods for green chemistry with Prof. R. S. Varma. Currently, he is working as senior research scientist at KAUST catalysis center directed by Prof. J. M. Basset. His research interests are in the area of advanced nano-materials for perfect catalysis. He has over 50 publications including various review articles and book chapters.

Prof. Rajender S. Varma was born in India (Ph.D., Delhi University 1976). After postdoctoral research at Robert Robinson Laboratories, Liverpool, UK, he was a faculty member at Baylor College of Medicine and Sam Houston State University prior to joining the US Environmental Protection Agency in 1999. He has over 35 years of research experience in management of multi-disciplinary programs that include nanomaterials and development of environmentally friendlier alternatives for synthetic methods using microwaves, and ultrasound etc. He has published over 300 scientific papers and has been awarded 6 US Patents.

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Table of Contents

Chapter 1 Fundamentals of Aqueous Microwave Chemistry Vivek Polshetlhvar Rajender S. Vavma 1

1.1 Introduction 1

1.2 Green Chemistry Approach 2

1.3 Water as Green Solvent 3

1.4 Why Microwaves? 4

1.4.1 Thermal Effect 4

1.4.2 Non-thermal Effect 5

1.4.3 Selectivity towards Water 6

1.4.4 Selectivity towards Catalyst 7

1.4.5 Catalyst as Susceptors 7

1.4.6 Stability of Catalyst 7

1.5 Conclusion 7

References 8

Chapter 2 Metal-catalyzed Reactions in Water under MW Irradiation Victorio Cadierno Pascale Crochet Sergio E. García-Garrido

2.1 Introduction 10

2.2 Addition Reactions 11

2.3 Isomerization Reactions 17

2.4 Substitution Reactions 19

2.5 Cyclization Reactions 28

2.6 Reduction and Oxidation Reactions 38

2.7 Miscellaneous Reactions 44

2.8 Representative Experimental Examples 45

2.8.1 Addition Reactions 45

2.8.2 Isomerization Reactions 46

2.8.3 Substitution Reactions 46

2.8.4 Cyclization Reactions 47

2.8.5 Reduction and Oxidation Reactions 48

2.8.6 Miscellaneous Reactions 48

2.9 Conclusions 49

Acknowledgements 49

References 49

Chapter 3 Microwave-assisted Coupling Reactions in Aqueous Media Aziz Fihri Christophe Len 55

3.1 Introduction 55

3.2 Suzuki-Miyaura Reaction 56

3.3 Heck Reaction 71

3.4 Sonogashira Reactions 75

3.5 Stille Reactions 78

3.6 Hiyama Reactions 78

3.7 Cyanation Reactions 79

3.8 Carbonylation Reactions 80

3.9 Representative Experimental Syntheses 83

3.9.1 Synthesis of 4,5-Dimethoxy-2-vinyl-2'-pivaloylamino-biphenyl 83

3.9.2 Synthesis of 4-Phenyltoluene 83

3.9.3 Synthesis of m-Carboxycinnamic Acid in Homogeneous Heck Reactions in D2O 84

3.9.4 Synthesis of Ethyl 3-(6-Methoxy-2-naphthyl) propanoate 84

3.9.5 Synthesis of 5-Chloro-2-phenylethynyl-pyridine 84

3.9.6 Synthesis of 4-Methoxybenzonitrile 85

3.9.7 Aminocarbonylation and Hydroxycarbonylation 85

3.10 Conclusion 86

References 86

Chapter 4 Microwave-assisted Synthesis of Bio-active Heterocycles in Aqueous Media Vivek Polshettiwar Rajender S. Varma 91

4.1 Introduction 91

4.2 MW-assisted Nitrogen-containing Heterocycle Synthesis in Water 92

4.3 MW-assisted Synthesis of Oxygen- and Sulfur-containing Heterocycles in Water 106

4.4 MW-assisted Miscellaneous Reactions in Water 112

4.5 Representative Experimental Procedures 118

4.5.1 Synthesis of Dihydropyrimidinones 118

4.5.2 Synthesis of 2-Aminochromene Derivatives 118

4.5.3 Synthesis of Dioxane-functionalized Molecules 118

4.5.4 Synthesis of Sulfonyl-benzothiazole-based Bio-active Compounds 119

4.5.5 Synthesis of a Series of new β-Aminoketones 119

4.6 Conclusions 119

References 119

Chapter 5 Microwave-assisted Enzymatic Reactions in Aqueous Media Hua Zhao 123

5.1 Introduction 123

5.2 Microwave-assisted Enzymatic Reactions in Water (or Aqueous Buffer) 125

5.2.1 Effect of Microwave Irradiation on Enzyme Activity in Aqueous Solutions 125

5.2.2 Microwave-assisted Enzymatic Protein Digestion 130

5.3 Microwave-assisted Enzymatic Reactions in Aqueous Solutions of Organic Solvents 132

5.4 Microwave-assisted Enzymatic Reactions in Ionic Liquids 133

5.5 Non-thermal Effect of Microwave Irradiation on Enzymes 136

5.6 Prospects of Microwave Irradiation in Aqueous Phase Biocatalysis 137

5.7 Experimental 137

5.7.1 Enzymatic Hydrolysis of Starch in Water under Microwave Irradiation 137

5.7.2 Enzymatic Transglycosylation of Lactose in Hexanol-Water (70:30, v/v) under Microwave Irradiation 138

5.7.3 Enzymatic Digestion of Proteins (Cytochrome c, Myoglobin, Lysozyme, and Ubiquitin) 138

Acknowledgements 138

References 138

Chapter 6 Microwave-assisted Synthesis of Polymers in Aqueous Media Catherine Marestin Régis Mercier 145

6.1 Introduction 145

6.2 Radical Polymerization in Aqueous Medium 146

6.2.1 Free-Radical Polymerization 146

6.2.2 Radical Polymerization in Dispersed Media 151

6.2.3 Controlled/Living Radical Polymerization in Dispersed Media 155

6.3 Step-growth Polymerization in Aqueous Media 157

6.3.1 Synthesis of Poly(ether)s 157

6.3.2 Synthesis of Poly(amide)s and Poly(imide)s 158

6.3.3 Synthesis of Polytriazoles 160

6.3.4 C-C Coupling Polymerizations 160

6.4 Miscellaneous Polymer Synthesis in Aqueous Media 162

6.4.1 Cationic Polymerization 162

6.4.2 Polymer Modifications 162

6.4.3 Solid-phase Peptide Synthesis in Water 169

6.5 Experimental 170

6.5.1 PMMA Grafting onto a Polysaccharide 170

6.5.2 PMMA Synthesis in Emulsion Polymerization 170

6.5.3 Synthesis of PMMA Nanoparticles 171

6.5.4 Synthesis of Polyacrylamide-Calcium Phosphate Nanocomposites 171

6.5.5 Nitroxide-assisted Synthesis of Styrene in Miniemulsion 171

6.5.6 Synthesis of Poly(ether)s 171

6.5.7 Synthesis of Poly(imide)s 171

6.5.8 Polymerization by C-C Coupling 172

6.5.9 Cationic Polymerization 172

6.5.10 Polymer Modification by Click Chemistry 172

References 172

Chapter 7 Microwave-assisted Synthesis of Nanomaterials in Aqueous Media Babita Baruwati Vivek Polshettiwar Rajender S. Varma 176

7.1 Introduction 176

7.2 Synthesis of Metal Nanoparticles using Water under Microwave Irradiation 178

7.2.1 Gold (Au) Nanoparticles 178

7.2.2 Silver (Ag) Nanoparticles 182

7.2.3 Palladium (Pd) and Platinum (Pt) Nanoparticles 185

7.3 Synthesis of Metal Oxide Nanoparticles in Aqueous Medium under MW Irradiation Conditions 186

7.3.1 Synthesis of Titania (TiO2) Nanoparticles 187

7.3.2 Synthesis of ZnO Nanoparticles 189

7.3.3 Synthesis of Ferrite Nanoparticles 191

7.3.4 Synthesis of Quantum Dots in Aqueous Medium under Microwave Conditions 194

7.4 Nanoparticles as Catalysts 195

7.5 Ruthenium Hydroxide Nano-catalyst for Microwave-assisted Hydration of Nitriles in Water 202

7.6 Glutathione-based Nano-organocatalyst for Microwave-assisted Synthesis of Heterocycles in Water 203

7.7 Representative Experimental Procedures 205

7.7.1 Synthesis of Gold Nanoparticles 205

7.7.2 Synthesis of Silver Nanoparticles 206

7.7.3 Synthesis of Different TiO2 Nanoparticles 207

7.7.4 Synthesis of ZnO Nanostructures 207

7.7.5 Selected Methods for Production of Ferrite Nanoparticles 208

7.8 Conclusion 209

References 209

Subject Index 217

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