Green Solvents, Volume 5 E-Book

• Herausgeber: Wiley-VCH
• Kategorie: Wissenschaft und neue Technologien
• Serie: Handbook of Green Chemistry
• Sprache: Englisch

Seitenzahl: 768

Veröffentlichungsjahr: 2014

Beschreibung

The shift towards being as environmentally-friendly as possible has resulted in the need for this important volume on the topic of reactions in water. Edited by one of the leaders in the field, Professor C.-J. Li, 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.

Leseprobe

CONTENTS

Cover

Related Titles

Title Page

Copyright

About the Editors

List of Contributors

Chapter 1: The Principles of and Reasons for Using Water as a Solvent for Green Chemistry

1.1 Introduction

1.2 Binding of Two Species Together Driven by the Hydrophobic Effect in Water

1.3 Aromatic Chlorination

1.4 Acylation of Cyclodextrins by a Bound Ester

1.5 Mimics of Metalloenzymes Using the Hydrophobic Effect in Water

1.6 Mimics of the Enzyme Ribonuclease

1.7 Mimics of Enzymes that Use Pyridoxamine Phosphate and Pyridoxal Phosphate as Coenzymes

1.8 Artificial Enzymes Carrying Mimics of Thiamine Pyrophosphate

1.9 Enolizations and Aldol Condensations

1.10 Hydrophobic Acceleration of Diels–Alder Reactions

1.11 Selectivities in Water Induced by the Hydrophobic Effect – Carbonyl Reductions

1.12 Selectivities in Water Induced by the Hydrophobic Effect – Oxidations

1.13 Using Hydrophobic Effects in Water to Determine the Geometries of Transition States for Some Important Reactions

1.14 Conclusion

References

Chapter 2: Green Acid Catalysis in Water

2.1 Introduction

2.2 Lewis Acids in Water

2.3 Chiral Lewis Acid-catalyzed Asymmetric Reactions in Water

2.4 Brønsted Acid Catalysis in Pure Water

2.5 Conclusion and Perspective

References

Chapter 3: Green Bases in Water

3.1 Introduction

3.2 Types of Bases and Their Use from a Green Point of View

3.3 Liquid–Liquid Processes

3.4 Solid–Liquid Processes

References

Chapter 4: Green Oxidation in Water

4.1 Introduction

4.2 Water-soluble Ligands

4.3 Oxidations Catalyzed by Metalloporphyrins and Metallophthalocyanines

4.4 Epoxidation and Dihydroxylation of Olefins in Aqueous Media

4.5 Alcohol Oxidations in Aqueous Media

4.6 Aldehyde and Ketone Oxidations in Water

4.7 Sulfoxidations in Water

4.8 Conclusion

References

Chapter 5: Green Reduction in Water

5.1 Introduction

5.2 Water-soluble Ligands

5.3 Hydrogenation in Water

5.4 Transfer Hydrogenation in Water

5.5 Role of Water

5.6 Conclusion

References

Chapter 6: Coupling Reactions in Water

6.1 Introduction

6.2 Reaction of Carbonyl Compounds and Derivatives

6.3 Reaction of Alkenes and Alkynes

6.4 Reaction of Organic Halides and Derivatives

6.5 Conclusion

References

Chapter 7: “On Water” for Green Chemistry

7.1 Introduction

7.2 Pericyclic Reactions

7.3 Addition of Heteronucleophiles to Unsaturated Carbonyl Compounds

7.4 Enantioselective Direct Aldol Reactions

7.5 Coupling Reactions

7.6 Oxidation

7.7 Bromination Reactions

7.8 Miscellaneous Reactions

7.9 Theoretical Studies

7.10 Conclusion

References

Chapter 8: Pericyclic Reactions in Water. Towards Green Chemistry

8.1 Introduction

8.2 Pericyclic Reactions in Aqueous Media

8.3 Conclusion

References

Chapter 9: Non-conventional Energy Sources for Green Synthesis in Water (Microwave, Ultrasound, and Photo)

9.1 Introduction

9.2 MW-assisted Organic Transformations in Aqueous Media

9.3 Sonochemical Organic Transformations in Aqueous Media

9.4 Photochemical Transformations in Aqueous Media

9.5 Conclusion

References

Chapter 10: Functionalization of Carbohydrates in Water

10.1 Introduction

10.2 C–C Bond Formation Reactions

10.3 C–N Bond Formation Reactions

10.4 Functionalization of Hydroxy Groups

10.5 Glyco-organic Substrates and Reactions in Aqueous Sugar Solutions

10.6 Conclusion

References

Chapter 11: Water Under Extreme Conditions for Green Chemistry

11.1 Introduction

11.2 Background

11.3 Recent Progress in HTW Synthesis

References

Chapter 12: Water as a Green Solvent for Pharmaceutical Applications

12.1 Introduction – Is Water a Green Solvent?

12.2 Water-based Enzymatic Processes

12.3 Processes in Which the Product is Isolated by pH Adjustment to the Isoelectric Point

12.4 Carbon–Carbon Bond-forming Cross-coupling Reactions in Water

12.5 Pharmaceutical Processes Using Mixed Aqueous Solvents

12.6 Conclusion

References

Chapter 13: Water as a Green Solvent for Bulk Chemicals

13.1 Introduction

13.2 Hydroformylation – an Overview

13.3 Water as Solvent for Hydroformylation

13.4 Water as Solvent in the Production of 2,7-Octadien–1-ol (Kuraray Process)

13.5 Conclusion

References

Index

End User License Agreement

List of Tables

Table 2.1

Table 5.1

Table 5.2

Table 5.3

Table 6.1

Table 7.1

Table 7.2

Table 7.3

Table 7.4

Table 7.5

Table 7.6

Table 7.7

Table 7.8

Table 7.9

Table 8.1

Table 10.1

Table 10.2

Table 10.3

Table 10.4

Table 10.5

Table 10.6

Table 10.7

Table 10.8

Table 10.9

Table 10.10

Table 11.1

Table 11.2

Table 12.1

Table 12.2

Table 13.1

Table 13.2

List of Illustrations

Scheme 1.1

Scheme 1.2

Scheme 1.3

Scheme 1.4

Scheme 1.5

Scheme 1.6

Scheme 1.7

Scheme 1.8

Scheme 1.9

Scheme 1.10

Scheme 1.11

Figure 1.1

Scheme 1.12

Scheme 1.13

Scheme 2.1

Scheme 2.2

Scheme 2.3

Scheme 2.4

Scheme 2.5

Scheme 2.6

Scheme 2.7

Scheme 2.8

Scheme 2.9

Scheme 2.10

Scheme 2.11

Scheme 2.12

Scheme 2.13

Scheme 2.14

Scheme 2.15

Scheme 2.16

Scheme 2.17

Figure 2.1

Scheme 2.18

Scheme 2.19

Scheme 2.20

Scheme 2.21

Figure 2.2

Scheme 2.22

Scheme 2.23

Scheme 2.24

Scheme 2.25

Scheme 2.26

Scheme 2.27

Scheme 2.28

Scheme 2.29

Scheme 2.30

Scheme 2.31

Scheme 2.32

Scheme 2.33

Scheme 2.34

Scheme 2.35

Scheme 2.36

Scheme 2.37

Scheme 2.38

Scheme 2.39

Scheme 3.1

Scheme 3.2

Scheme 3.3

Scheme 3.4

Scheme 3.5

Scheme 3.6

Scheme 3.7

Scheme 3.8

Scheme 3.9

Scheme 3.10

Scheme 3.11

Scheme 3.12

Scheme 3.13

Scheme 3.14

Scheme 3.15

Scheme 3.16

Scheme 3.17

Scheme 3.18

Scheme 3.19

Scheme 3.20

Scheme 3.21

Scheme 3.22

Scheme 4.1

Scheme 4.2

Scheme 4.3

Scheme 4.4

Scheme 4.5

Scheme 4.6

Scheme 4.7

Scheme 4.8

Scheme 4.9

Scheme 4.10

Scheme 4.11

Scheme 4.12

Scheme 4.13

Scheme 4.14

Scheme 4.15

Scheme 4.16

Scheme 4.17

Scheme 4.18

Scheme 4.19

Scheme 4.20

Scheme 4.21

Scheme 4.22

Scheme 4.23

Scheme 4.24

Scheme 5.1

Scheme 5.2

Scheme 5.3

Scheme 5.4

Scheme 5.5

Scheme 5.6

Scheme 5.7

Scheme 5.8

Scheme 5.9

Scheme 5.10

Scheme 5.11

Scheme 5.12

Scheme 5.13

Scheme 5.14

Scheme 5.15

Scheme 5.16

Scheme 5.17

Scheme 5.18

Scheme 5.19

Scheme 5.20

Scheme 5.21

Scheme 5.22

Scheme 5.23

Scheme 5.24

Scheme 5.25

Scheme 5.26

Scheme 5.27

Scheme 5.28

Scheme 5.29

Scheme 5.30

Scheme 5.31

Scheme 5.32

Scheme 5.33

Scheme 6.1

Scheme 6.2

Scheme 6.3

Scheme 6.4

Scheme 6.5

Scheme 6.6

Scheme 6.7

Scheme 6.8

Scheme 6.9

Scheme 6.10

Scheme 6.11

Scheme 6.12

Scheme 6.13

Scheme 6.14

Scheme 6.15

Scheme 6.16

Scheme 6.17

Scheme 6.18

Scheme 6.19

Scheme 6.20

Scheme 6.21

Scheme 6.22

Scheme 6.23

Scheme 6.24

Scheme 6.25

Scheme 6.26

Scheme 6.27

Scheme 6.28

Scheme 6.29

Scheme 6.30

Scheme 6.31

Scheme 6.32

Scheme 6.33

Scheme 6.34

Scheme 6.35

Scheme 6.36

Scheme 6.37

Scheme 6.38

Scheme 6.39

Scheme 6.40

Scheme 6.41

Scheme 6.42

Scheme 6.43

Scheme 6.44

Scheme 6.45

Scheme 6.46

Scheme 6.47

Scheme 6.48

Scheme 6.49

Scheme 6.50

Scheme 6.51

Scheme 6.52

Scheme 6.53

Scheme 6.54

Scheme 6.55

Scheme 6.56

Scheme 6.57

Scheme 6.58

Scheme 6.59

Scheme 6.60

Scheme 6.61

Scheme 6.62

Scheme 6.63

Scheme 6.64

Scheme 6.65

Scheme 6.66

Scheme 6.67

Scheme 6.68

Scheme 6.69

Scheme 6.70

Scheme 6.71

Scheme 6.72

Scheme 6.73

Scheme 6.74

Scheme 6.75

Scheme 6.76

Scheme 6.77

Scheme 6.78

Scheme 6.79

Scheme 6.80

Scheme 6.81

Figure 7.1

Scheme 7.1

Scheme 7.2

Scheme 7.3

Scheme 7.4

Scheme 7.5

Scheme 7.6

Scheme 7.7

Scheme 7.8

Scheme 7.9

Scheme 7.10

Scheme 7.11

Scheme 7.12

Scheme 7.13

Scheme 7.14

Scheme 7.15

Scheme 7.16

Scheme 7.17

Scheme 7.18

Scheme 7.19

Scheme 7.20

Scheme 7.21

Scheme 7.22

Figure 7.2

Scheme 8.1

Scheme 8.2

Scheme 8.3

Scheme 8.4

Scheme 8.5

Scheme 8.6

Figure 8.1

Scheme 8.7

Figure 8.2

Figure 8.3

Scheme 8.8

Scheme 8.9

Scheme 8.10

Scheme 8.11

Scheme 8.12

Scheme 8.13

Figure 8.4

Scheme 8.14

Scheme 8.15

Scheme 8.16

Scheme 8.17

Scheme 8.18

Scheme 8.19

Scheme 8.20

Scheme 8.21

Scheme 8.22

Scheme 8.23

Scheme 8.24

Scheme 8.25

Scheme 8.26

Scheme 8.27

Scheme 8.28

Scheme 8.29

Scheme 8.30

Scheme 8.31

Scheme 8.32

Scheme 8.33

Scheme 8.34

Figure 8.5

Scheme 8.35

Scheme 8.36

Scheme 8.37

Scheme 8.38

Scheme 8.39

Scheme 8.40

Scheme 9.1

Scheme 9.2

Scheme 9.3

Scheme 9.4

Scheme 9.5

Scheme 9.6

Scheme 9.7

Scheme 9.8

Scheme 9.9

Scheme 9.10

Scheme 9.11

Scheme 9.12

Scheme 9.13

Scheme 9.14

Scheme 9.15

Scheme 9.16

Scheme 9.17

Scheme 9.18

Scheme 9.19

Scheme 9.20

Scheme 9.21

Scheme 9.22

Scheme 9.23

Scheme 9.24

Scheme 9.25

Scheme 9.26

Scheme 9.27

Scheme 9.28

Scheme 9.29

Scheme 9.30

Scheme 9.31

Scheme 9.32

Scheme 10.1

Scheme 10.2

Scheme 10.3

Scheme 10.4

Scheme 10.5

Scheme 10.6

Scheme 10.7

Scheme 10.8

Scheme 10.9

Scheme 10.10

Scheme 10.11

Scheme 10.12

Scheme 10.13

Scheme 10.14

Scheme 10.15

Scheme 10.16

Scheme 10.17

Scheme 10.18

Scheme 10.19

Scheme 10.20

Scheme 10.21

Scheme 10.22

Scheme 10.23

Scheme 10.24

Scheme 10.25

Scheme 10.26

Scheme 10.27

Scheme 10.28

Scheme 10.29

Scheme 10.30

Scheme 10.31

Scheme 10.32

Scheme 10.33

Scheme 10.34

Scheme 10.35

Scheme 10.36

Scheme 10.37

Scheme 10.38

Scheme 10.39

Scheme 10.40

Scheme 10.41

Scheme 10.42

Scheme 10.43

Scheme 10.44

Scheme 10.45

Scheme 10.46

Scheme 10.47

Scheme 10.48

Scheme 10.49

Scheme 10.50

Scheme 10.51

Figure 11.1

Figure 11.2

Figure 11.3

Scheme 11.1

Figure 11.4

Figure 11.5

Figure 11.6

Figure 11.7

Scheme 11.2

Scheme 11.3

Scheme 11.4

Scheme 11.5

Scheme 11.6

Scheme 12.1

Scheme 12.2

Scheme 12.3

Scheme 12.4

Scheme 12.5

Scheme 12.6

Scheme 12.7

Scheme 12.8

Scheme 12.9

Scheme 12.10

Scheme 12.11

Scheme 12.12

Scheme 12.13

Scheme 12.14

Scheme 12.15

Scheme 12.16

Scheme 12.17

Scheme 12.18

Figure 12.1

Scheme 13.1

Scheme 13.2

Figure 13.1

Scheme 13.3

Scheme 13.4

Figure 13.2

Figure 13.3

Scheme 13.5

Scheme 13.6

Figure 13.4

Guide

Cover

Table of Contents

About the Editors

Chapter 1

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Handbook of Green Chemistry

Volume 5Reactions in Water

Edited by

Chao-Jun Li

All books published by Wiley-VCH are carefully produced. Nevertheless, authors, editors, and publisher do not warrant the information contained in these books, including this book, to be free of errors. Readers are advised to keep in mind that statements, data, illustrations, procedural details or other items may inadvertently be inaccurate.

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© 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Boschstr. 12, 69469 Weinheim, Germany

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ISBN: 978-3-527-31591-7

About the Editors

Series Editor

Paul T. Anastas joined Yale University as Professor and serves as the Director of the Center for Green Chemistry and Green Engineering there. From 2004–2006, Paul was the Director of the Green Chemistry Institute in Washington, D.C. Until June 2004 he served as Assistant Director for Environment at the 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

Chao-Jun Li (FRSC, UK) received his PhD at McGill University (1992) and was an NSERC Postdoctoral fellow at Stanford University (1992–1994). He was an Assistant Professor (1994), Associate Professor (1998) and Full Professor (2000–2003) at Tulane University, where he received a NSF CAREER Award (1998) in organic synthesis and the 2001 US Presidential Green Chemistry Challenge Award (Academic). In 2003, he became a Canada Research Chair (Tier I) in Organic/Green Chemistry and a Professor of Chemistry at McGill University in Canada. He serves as the Co-Chair of the Canadian Green Chemistry and Engineering Network, the Director of CFI Infrastructure for Green Chemistry and Green Chemicals, and Co-Director the FQRNT Center for Green Chemistry and Catalysis (Quebec). He is the current Associate Editor for Americas for the journal of Green Chemistry (published by the Royal Society of Chemistry). He has been widely recognized as the leader in Green Chemistry for Organic Synthesis in developing innovative and fundamentally new organic reactions that defy conventional reactivities and have high synthetic efficiency.

List of Contributors

Ronald Breslow

Columbia University

Department of Chemistry

3000 Broadway

New York, NY 10027

USA

Peter Dunn

Pfizer UK

Pfizer Green Chemistry Lead

Ramsgate Road

Sandwich

Kent CT13 9NJ

UK

Jan B.F.N. Engberts

University of Groningen

Stratingh Institute

Nijenborgh 4

9747 AG Groningen

The Netherlands

José M. Fraile

Universidad de Zaragoza-CSIC

Instituto de Ciencia de Materiales de Aragón

Facultad de Ciencias

Departamento de Química Orgánica

50009 Zaragoza

Spain

Jean-Pierre Genêt

ENSCP

UMR 7573

Laboratoire de Synthèse Sélective Organique et Produits Naturels

11 rue P. et M. Curie

72231 Paris Cedex 05

France

Clara I. Herrerías

Universidad de Zaragoza-CSIC

Instituto de Ciencia de Materiales de Aragón

Facultad de Ciencias

Departamento de Química Orgánica

50009 Zaragoza

Spain

Ferenc Joó

Hungarian Academy of Sciences

Research Group of Homogeneous Catalysis

and

University of Debrecen

Institute of Physical Chemistry

1 Egyetem tér

4010 Debrecen

Hungary

Ágnes Kathó

University of Debrecen

Institute of Physical Chemistry

1 Egyetem tér

4010 Debrecen

Hungary

Jaap E. Klijn

University of Groningen

Stratingh Institute

Nijenborgh 4

9747 AG Groningen

The Netherlands

Sh Kobayashi

The University of Tokyo

School of Science and Graduate School of Pharmaceutical Sciences

Department of Chemistry

Hongo

Bunkyo-ku

Tokyo 113-0033

Japan

Lucie Leseurre

ENSCP

UMR 7573

Laboratoire de Synthèse Sélective Organique et Produits Naturels

11 rue P. et M. Curie

72231 Paris Cedex 05

France

Li Liu

Chinese Academy of Sciences

Institute of Chemistry

Center for Chemical Biology

Beijing National Laboratory for Molecular Science (BNLMS)

Beijing 100080

China

André Lubineau

Université Paris-Sud 11

Institut de Chimie Moléculaire et des Matériaux d'Orsay

CNRS UMR 8182

Laboratoire de Chimie Organique Multifonctionnelle, Bâtiment 420

15 rue Georges Clémenceau

91405 Orsay

France

José A. Mayoral

Universidad de Zaragoza-CSIC

Instituto de Ciencia de Materiales de Aragón

Facultad de Ciencias

Departamento de Química Orgánica

50009 Zaragoza

Spain

Véronique Michelet

ENSCP

UMR 7573

Laboratoire de Synthèse Sélective Organique et Produits Naturels

11 rue P. et M. Curie

72231 Paris Cedex 05

France

Chikako Ogawa

The University of Tokyo

School of Science and Graduate School of Pharmaceutical Sciences

Department of Chemistry

Hongo

Bunkyo-ku

Tokyo 113-0033

Japan

Present address:

Eisai Research Institute

Lead Identification

4 Corporate Drive

Andover, MA 01810

USA

Vivek Polshettiwar

US Environmental Protection Agency

National Risk Management Research Laboratory

Sustainable Technology Division

26 W. Martin Luther King Drive

Cincinnati, OH 45268

USA

Yves Queneau

INSA-Lyon

Laboratoire de Chimie Organique

Bâtiment J. Verne

20 avenue A. Einstein

69621 Villeurbanne

France

and

Université Lyon 1

Institut de Chimie et Biochimie Moléculaires et Supramoléculaires

INSA-Lyon

CNRS, UMR 5246

CPE-Lyon

Bâtiment CPE

43 boulevard du 11 novembre 1918

69622 Villeurbanne

France

Natalie A. Rebacz

University of Michigan

Chemical Engineering Department

2300 Hayward

Ann Arbor, MI 48109

USA

Phillip E. Savage

University of Michigan

Chemical Engineering Department

2300 Hayward

Ann Arbor, MI 48109

USA

Marie-Christine Scherrmann

Université Paris-Sud 11

Institut de Chimie Moléculaire et des Matériaux d'Orsay

CNRS UMR 8182

Laboratoire de Procédés et Substances Naturelles

Bâtiment 410

15 rue Georges Clémenceau

91405 Orsay

France

Roger A. Sheldon

Delft University of Technology

Department of Biotechnology

Julianalaan 136

2628 BL Delft

The Netherlands

Rajender S. Varma

US Environmental Protection Agency

National Risk Management Research Laboratory

Sustainable Technology Division

26 W. Martin Luther King Drive

Cincinnati, OH 45268

USA

Dong Wang

Chinese Academy of Sciences

Institute of Chemistry

Center for Chemical Biology

Beijing National Laboratory for Molecular Science (BNLMS)

Beijing 100080

China

Xiaofeng Wu

University of Liverpool

Liverpool Centre for Materials and Catalysis

Department of Chemistry

Liverpool L69 7ZD

UK

Jianliang Xiao

University of Liverpool

Liverpool Centre for Materials and Catalysis

Department of Chemistry

Liverpool L69 7ZD

UK

1The Principles of and Reasons for Using Water as a Solvent for Green Chemistry

Ronald Breslow

1.1 Introduction

Chemical reactions used to manufacture important compounds such as medicinals are essentially always carried out in solution, and this is also true of the research work that is used to invent the new compounds and to develop appropriate ways to manufacture them. In the past, continuing into the present, the solvents used are normally volatile organic compounds (VOCs), and these pose an environmental problem. Their vapors can contribute to the greenhouse effect that causes global warming, and in some cases the solvent vapors can catalyze the destruction of the ozone layer that protects the Earth and its living inhabitants from short-wavelength ultraviolet solar radiation. The vapors may also be toxic to humans, plants, or animals, or they may cause diseases.