Liquid Phase Aerobic Oxidation Catalysis

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
List of Contributors

PART I RADICAL CHAIN AEROBIC OXIDATION
1 Overview of Radical Chain Oxidation Chemistry
2 Noncatalyzed Radical Chain Oxidation: Cumene Hydroperoxide
3 Cyclohexane Oxidation: History of Transition from Catalyzed to Noncatalyzed
4 Chemistry and Mechanism of Oxidation of para-Xylene to Terephthalic Acid Using Co-Mn-Br Catalyst

PART II Cu-CATALYZED AEROBIC OXIDATION
5 Cu-Catalyzed Aerobic Oxidation: Overview and New Developments
6 Copper-Catalyzed Aerobic Alcohol Oxidation
7 Phenol Oxidations

PART III Pd-CATALYZED AEROBIC OXIDATION
8 Pd-Catalyzed Aerobic Oxidation Reactions: Industrial Applications and New Developments
9 Acetaldehyde from Ethylene and Related Wacker-Type Reactions
10 1,4-Butanediol from 1,3-Butadiene
11 Mitsubishi Chemicals Liquid Phase Palladium-Catalyzed Oxidation Technology: Oxidation of Cyclohexene, Acrolein, and Methyl Acrylate to Useful Industrial Chemicals
12 Oxidative Carbonylation: Diphenyl Carbonate
13 Aerobic Oxidative Esterification of Aldehydes with Alcohols: The Evolution from Pd-Pb Intermetallic Catalysts to Au-NiOx Nanoparticle Catalysts for the Production of Methyl Methacrylate

PART IV ORGANOCATALYTIC AEROBIC OXIDATION
14 Quinones in Hydrogen Peroxide Synthesis and Catalytic Aerobic Oxidation Reactions
15 NOx Cocatalysts for Aerobic Oxidation Reactions: Application to Alcohol Oxidation
16 N-Hydroxyphthalimide (NHPI)-Organocatalyzed Aerobic Oxidations: Advantages, Limits, and Industrial Perspectives
17 Carbon Materials as Nonmetal Catalysts for Aerobic Oxidations: The Industrial Glyphosate Process and New Developments

PART V BIOCATALYTIC AEROBIC OXIDATION
18 Enzyme Catalysis: Exploiting Biocatalysis and Aerobic Oxidations for High-Volume and High-Value Pharmaceutical Syntheses

PART VI OXIDATIVE CONVERSION OF RENEWABLE FEEDSTOCKS
19 From Terephthalic Acid to 2,5-Furandicarboxylic Acid: An Industrial Perspective
20 Azelaic Acid from Vegetable Feedstock via Oxidative Cleavage with Ozone or Oxygen
21 Oxidative Conversion of Renewable Feedstock: Carbohydrate Oxidation

PART VII AEROBIC OXIDATION WITH SINGLET OXYGEN
22 Industrial Prospects for the Chemical and Photochemical Singlet Oxygenation of Organic Compounds

PART VIII REACTOR CONCEPTS FOR LIQUID PHASE AEROBIC OXIDATION
23 Reactor Concepts for Aerobic Liquid Phase Oxidation: Microreactors and Tube Reactors

Index