Liquid Phase Aerobic Oxidation Catalysis

The first book to place recent academic developments within the context of real life industrial applications, this is a timely overview of the field of aerobic oxidation reactions in the liquid phase that also illuminates the key challenges that lie ahead.
As such, it covers both homogeneous as well as heterogeneous chemocatalysis and biocatalysis, along with examples taken from various industries: bulk chemicals and monomers, specialty chemicals, flavors and fragrances, vitamins, and pharmaceuticals. One chapter is devoted to reactor concepts and engineering aspects of these methods, while another deals with the relevance of aerobic oxidation catalysis for the conversion of renewable feedstock.
With chapters written by a team of academic and industrial researchers, this is a valuable reference for synthetic and catalytic chemists at universities as well as those working in the pharmaceutical and fine chemical industries seeking a better understanding of these reactions and how to design large scale processes based on this technology.

Shannon Stahl is a Professor of Chemistry at the University of Wisconsin-Madison, USA, since 1999. After undergraduate studies at the University of Illinois at Urbana-Champaign, USA, he attended the California Institute of Technology, USA, for doctoral studies. He worked on Pt-catalyzed oxidation of methane to methanol in the laboratory of Prof. John E. Bercaw and obtained his Ph.D. in 1997. From 1997-1999, he conducted postdoctoral research in the lab of Prof. Stephen J. Lippard at Massachusetts Institute of Technology, USA, investigating the enzyme methane monooxygenase. He has published >120 research articles and is the recipient of numerous awards, including the Humboldt Senior Research Award, ACS Cope Scholar Award, Sloan Research Fellowship, and he is a Fellow of the AAAS. His research group specializes in the development and mechanistic characterization of catalytic aerobic oxidation reactions.

Paul Alsters is a Principal Scientist at DSM Ahead R&D B.V. - Innovative Synthesis (Geleen, The Netherlands). He received his Ph.D. at the University of Utrecht, The Netherlands, in 1992, working on C-O coupling reactions of organopalladium compounds under the guidance of Prof. G. van Koten. He did postdoctoral work on asymmetric titanium mediated nucleophilic additions to aldehydes in the laboratory of R.O. Duthaler at Ciba-Geigy in Basel, Switzerland. He joined DSM in 1993. His main areas of interest are development of scalable break-through methods for new or existing products, and liquid-phase catalysis, with an emphasis on C-X or C-C coupling reactions and oxidation catalysis. His research activities frequently operate at the interplay of catalysis/synthesis and other sciences, in particular materials science. He is the (co-)author of >70 articles or book chapters and (co-)inventor of >20 patents.

Preface XV

List of Contributors XVII

Part I Radical Chain Aerobic Oxidation 1

1 Overview of Radical Chain Oxidation Chemistry 3
Ive Hermans

1.1 Introduction 3

1.2 Chain Initiation 6

1.3 Chain Propagation 7

1.4 Formation of Ring-Opened By-Products in the Case of Cyclohexane Oxidation 11

1.5 Complications in the Case of Olefin Autoxidation 12

1.6 Summary and Conclusions 13

References 14

2 Noncatalyzed Radical Chain Oxidation: Cumene Hydroperoxide 15
Manfred Weber, Jan-Bernd Grosse Daldrup, and Markus Weber

2.1 Introduction 15

2.2 Chemistry and Catalysis 15

2.3 Process Technology 21

2.4 New Developments 27

References 30

3 Cyclohexane Oxidation: History of Transition from Catalyzed to Noncatalyzed 33
Johan Thomas Tinge

3.1 Introduction 33

3.2 Chemistry and Catalysis 34

3.3 Process Technology 35

3.4 New Developments 38

Epilogue 39

References 39

4 Chemistry and Mechanism of Oxidation of para-Xylene to Terephthalic Acid Using Co–Mn–Br Catalyst 41
Victor A. Adamian and William H. Gong

4.1 Introduction 41

4.2 Chemistry and Catalysis 42

4.3 Process Technology 58

4.4 New Developments 61

4.5 Conclusions 62

References 63

Part II Cu-Catalyzed Aerobic Oxidation 67

5 Cu-Catalyzed Aerobic Oxidation: Overview and New Developments 69
Damian Hruszkewycz, Scott McCann, and Shannon Stahl

5.1 Introduction 69

5.2 Chemistry and Catalysis 70

5.3 Process Technology 74

5.4 New Developments: Pharmaceutical Applications of Cu-Catalyzed Aerobic Oxidation Reactions 76

References 82

6 Copper-Catalyzed Aerobic Alcohol Oxidation 85
Janelle E. Steves and Shannon S. Stahl

6.1 Introduction 85

6.2 Chemistry and Catalysis 86

6.3 Prospects for Scale-Up 91

6.4 Conclusions 93

References 94

7 Phenol Oxidations 97

7.1 Polyphenylene Oxides by Oxidative Polymerization of Phenols 97
Patrick Gamez

7.2 2,3,5-Trimethylhydroquinone as a Vitamin E Intermediate via Oxidation of Methyl-Substituted Phenols 106
Jan Schütz and Thomas Netscher

References 109

Part III Pd-Catalyzed Aerobic Oxidation 113

8 Pd-Catalyzed Aerobic Oxidation Reactions: Industrial Applications and New Developments 115
Dian Wang, Jonathan N. Jaworski, and Shannon S. Stahl

8.1 Introduction 115

8.2 Chemistry and Catalysis: Industrial Applications 117

8.3 Chemistry and Catalysis: Applications of Potential Industrial Interest 122

8.4 Chemistry and Catalysis: New Developments and Opportunities 128

8.5 Conclusion 133

References 133

9 Acetaldehyde from Ethylene and Related Wacker-Type Reactions 139
Reinhard Jira

9.1 Introduction 139

9.2 Chemistry and Catalysis 140

9.3 Process Technology (Wacker Process) 148

9.4 Other Developments 151

References 155

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Liquid Phase Aerobic Oxidation Catalysis Industrial Applications and Academic Perspectives

Summary

Author Biography

Table of Contents

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