Handbook of Green Chemistry, Green Catalysis, Homogeneous Catalysis [NOOK Book]


Green Chemistry is a vitally important subject area in a world where being as green and environmentally sound as possible is no longer a luxury but a necessity. Its applications include the design of chemical products and processes that ...
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Handbook of Green Chemistry, Green Catalysis, Homogeneous Catalysis

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Green Chemistry is a vitally important subject area in a world where being as green and environmentally sound as possible is no longer a luxury but a necessity. Its applications include the design of chemical products and processes that help to reduce or eliminate the use and generation of hazardous substances.

The Handbook of Green Chemistry comprises 12 volumes, split into subject-specific sets as follows:

Set I: Green Catalysis
- Volume 1: Homogeneous Catalysis
- Volume 2: Heterogeneous Catalysis
- Volume 3: Biocatalysis
Set II: Green Solvents
Set III: Green Processes
Set IV: Green Products

Homogeneous catalysis can lead to cleaner, safer reactions. The volume covers many different aspects of homogeneous catalysis, from industrial applications to atom economy. The fundamentals are explained and examples from everday are used to explain this vitally important field.
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Product Details

  • ISBN-13: 9783527688661
  • Publisher: Wiley
  • Publication date: 4/7/2014
  • Series: Handbook of Green Chemistry
  • Sold by: Barnes & Noble
  • Format: eBook
  • Edition description: Volume 1
  • Edition number: 1
  • Pages: 431
  • File size: 10 MB

Meet the Author

Series Editor
Paul T. Anastas joined Yale University as Professor and serves 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.

Volume Editor
Bob Crabtree took his first degree at Oxford, did his Ph.D. at Sussex and spent four years in Paris at the CNRS. He has been at Yale since 1977. He has chaired the Inorganic Division at ACS, and won the ACS and RSC organometallic chemistry prizes. He is the author of an organometallic textbook, and editor-in-chief of the Encyclopedia of Inorganic Chemistry and Comprehensive Organometallic Chemistry. He has contributed to C-H activation, H2 complexes, dihydrogen bonding, and his homogeneous tritiation and hydrogenation catalyst is in wide use. More recently, he has combined molecular recognition with CH hydroxylation to obtain high selectivity with a biomimetic strategy.

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Table of Contents

About the Editors XIII

List of Contributors XV

1 Atom Economy – Principles and Some Examples 1
Audrey Moores

1.1 Introduction 1

1.2 Principle of Atom Economy 2

1.3 Atom Economical by Design: Examples of Reactions Relying on C–H Activation 6

1.4 Conclusion 12

References 13

2 Catalysis Involving Fluorous Phases: Fundamentals and Directions for Greener Methodologies 17
John A. Gladysz

2.1 Introduction 17

2.2 Directions for Greener Fluorous Methodologies 19

2.3 Solvents for Fluorous Chemistry 21

2.4 Ponytails and Partition Coefficients 23

2.5 Specific Examples of Catalyst Recovery that Exploit Temperature-dependent Solubilities 24

2.6 Specific Examples of Catalyst Recovery that Exploit Fluorous Solid Phases 30

2.7 Summary and Perspective 35

References 36

3 Chemistry and Applications of Iron–TAML Catalysts in Green Oxidation Processes Based on Hydrogen Peroxide 39
Terrence J. Collins, Sushil K. Khetan, and Alexander D. Ryabov

3.1 Introduction 39

3.2 Properties of Fe–TAMLs and Mechanisms of Oxidation with Hydrogen Peroxide 40

3.3 Applications of Fe–TAMLs 61

3.4 Conclusion 73

References 74

4 Microwave-Accelerated Homogeneous Catalysis in Water 79
Luke R. Odell and Mats Larhed

4.1 Introduction 79

4.2 Suzuki–Miyaura Reactions 82

4.3 The Stille Reaction 85

4.4 The Hiyama Cross-Coupling Reaction 86

4.5 The Heck Reaction 86

4.6 Carbonylation Reactions 88

4.7 The Sonogashira Reaction 90

4.8 Aryl–Nitrogen Couplings 91

4.9 Aryl–Oxygen Couplings 92

4.10 Miscellaneous Transformations 92

4.11 Conclusion 94

References 95

5 Ionic Liquids and Catalysis: the IFP Biphasic Difasol Process 101
Hélène Olivier-Bourbigou, Frédéric Favre, Alain Forestière, and François Hugues

5.1 Introduction 101

5.2 The Solvent in Catalytic Reactions 102

5.3 The Catalytic Oligomerization of Olefins 104

5.4 The Biphasic Difasol Process 113

5.5 Conclusion 124

References 124

6 Immobilization and Compartmentalization of Homogeneous Catalysts 127
Christian Müller and Dieter Vogt

6.1 Introduction 127

6.2 Soluble Dendrimer-bound Homogeneous Catalysts 128

6.3 Polymer-bound Homogeneous Catalysts 138

6.4 Conclusion and Outlook 149

References 149

7 Industrial Applications of Homogeneous Enantioselective Catalysts 153
Hans-Ulrich Blaser, Garrett Hoge, Benoît Pugin, and Felix Spindler

7.1 Introduction and Scope 153

7.2 Critical Factors for the Technical Application of Homogeneous Enantioselective Catalysts 155

7.3 Industrial Processes: General Comments 157

7.4 Hydrogenation of C¼C Bonds 159

7.5 Hydrogenation of C¼O Bonds 175

7.6 Hydrogenation of C¼N Bonds 181

7.7 Oxidation Processes 183

7.8 Miscellaneous Transformations (Isomerization, Addition Reactions to C¼C, C¼O and C¼N Bonds, Opening of Oxacycles) 188

7.9 Conclusions and Future Developments 195

References 196

8 Hydrogenation for C– C Bond Formation 205
John F. Bower and Michael J. Krische

8.1 By-product-free C–C Coupling and the Departure from Preformed Organometallic Reagents 205

8.2 Hydrogenative Vinylation of Carbonyl Compounds and Imines 210

8.3 Hydrogenative Allylation of Carbonyl Compounds 217

8.4 Hydrogenative Aldol and Mannich Additions 224

8.5 Hydrogenative Acyl Substitution (Reductive Hydroacylation) 233

8.6 Hydrogenative Carbocyclization 236

8.7 Future Directions 240

References 241

9 Organocatalysis 255
Isabelle McCort-Tranchepain, Morgane Petit, and Peter I. Dalko

9.1 Introduction 255

9.2 Catalysts 256

9.3 Reactions 264

9.4 Conclusion 309

References 309

10 Palladacycles in Catalysis 319
Jairton Dupont and Fabricio R. Flores

10.1 Introduction 319

10.2 Catalyst Precursors for C–C and C–X (Heteroatom) Coupling Reactions 320

10.3 Other Catalytic Reactions Catalyzed by Palladacycles 333

10.4 Conclusion 337

References 338

11 Homogeneous Catalyst Design for the Synthesis of Aliphatic Polycarbonates and Polyesters 343
Geoffrey W. Coates and Ryan C. Jeske

11.1 Introduction 343

11.2 Synthesis of Aliphatic Polycarbonates from Epoxides and Carbon Dioxide 344

11.3 Synthesis of Aliphatic Polyesters 360

References 370

12 The Aerobic Oxidation of p-Xylene to Terephthalic acid: a Classic Case of Green Chemistry in Action 375
Walt Partenheimer and Martyn Poliakoff

12.1 Introduction 375

12.2 Methods of Making Terephthalic Acid Using Stoichiometric Reagents 377

12.3 Methods for Preparing Terephthalic Acid Using Cobalt Acetate and Dioxygen in Acetic Acid 378

12.4 Adding Bromide to Improve Terephthalic Acid Production Using Cobalt and Manganese Acetates in Acetic Acid 385

12.5 Potential Processes Using Water as a Solvent 388

12.6 Summary and Final Comments 392

References 394

Index 399

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