Handbook of Green Chemistry - Green Catalysis / Edition 1

Handbook of Green Chemistry - Green Catalysis / Edition 1

by Paul T. Anastas
ISBN-10:
3527324976
ISBN-13:
9783527324972
Pub. Date:
02/17/2009
Publisher:
Wiley
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Overview

Handbook of Green Chemistry - Green Catalysis / Edition 1

The shift towards being as environmentally-friendly as possible has resulted in the need for this important volume on homogeneous catalysis. Edited by the father and pioneer of Green Chemistry, Professor Paul Anastas, and by the renowned chemist, Professor Robert Crabtree, this volume covers many different aspects, from industrial applications to atom economy. It explains the fundamentals and makes use of everyday examples to elucidate this vitally important field.

An essential collection for anyone wishing to gain an understanding of the world of green chemistry, as well as for chemists, environmental agencies and chemical engineers.

The Handbook of Green Chemistry comprises of 9 volumes in total, split into 3 subject-specific sets. The three sets are available individually. All 9 volumes are available individually, too.

Set I: Green Catalysis 
  - Volume 1: Homogeneous Catalysis 
  - Volume 2: Heterogeneous Catalysis 
  - Volume 3: Biocatalysis

Set II: Green Solvents
  - Volume 4: Supercritical Solvents
  - Volume 5: Reactions in Water
  - Volume 6: Ionic Liquids

Set III: Green Processes
  - Volume 7: Green Synthesis
  - Volume 8: Green Nanoscience
  - Volume 9: Designing Safer Chemicals

The Handbook of Green Chemistry is also available as Online Edition.

Podcasts
Listen to two podcasts in which Professor Paul Anastas and Journals Editor Paul Trevorrow discuss the origin and expansion of Green Chemistry and give an overview of The Handbook of Green Chemistry.

Product Details

ISBN-13: 9783527324972
Publisher: Wiley
Publication date: 02/17/2009
Series: Handbook of Green Chemistry Series
Pages: 355
Product dimensions: 6.90(w) x 9.60(h) x 0.90(d)

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 C—C Bonds 159

7.5 Hydrogenation of C—O Bonds 175

7.6 Hydrogenation of C=N Bonds 181

7.7 Oxidation Processes 183

7.8 Miscellaneous Transformations (Isomerization, Addition Reactions to C—C, C—O and C=N 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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