Liquid Phase Aerobic Oxidation Catalysis: Industrial Applications and Academic Perspectives

Content: 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 Schutz 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     Further Reading 158     10 1,4-Butanediol from 1,3-Butadiene 159 Yusuke Izawa and Toshiharu Yokoyama     10.1 Introduction 159     10.2 Chemistry and Catalysis 160     10.3 Process Technology 164     10.4 New Developments 168     10.5 Summary and Conclusions 169     References 170     11 Mitsubishi Chemicals Liquid Phase Palladium-Catalyzed Oxidation Technology: Oxidation of Cyclohexene, Acrolein, and Methyl Acrylate to Useful Industrial Chemicals 173 Yoshiyuki Tanaka, Jun P. Takahara, Tohru Setoyama, and Hans E. B. Lempers     11.1 Introduction 173     11.2 Chemistry and Catalysis 174     11.3 Prospects for Scale-Up 180     11.4 Conclusion 187     References 187     12 Oxidative Carbonylation: Diphenyl Carbonate 189 Grigorii L. Soloveichik     12.1 Introduction 189     12.2 Chemistry and Catalysis 192     12.3 Prospects for Scale-Up 201     12.4 Conclusions and Outlook 203     Acknowledgments 204     References 205     13 Aerobic Oxidative Esterification of Aldehydes with Alcohols: The Evolution from Pd   Pb Intermetallic Catalysts to Au   NiOx Nanoparticle Catalysts for the Production ofMethylMethacrylate 209 Ken Suzuki and Setsuo Yamamatsu     13.1 Introduction 209     13.2 Chemistry and Catalysis 210     13.3 Process Technology 214     13.4 New Developments 215     13.5 Conclusion and Outlook 217     References 218     Part IV Organocatalytic Aerobic Oxidation 219     14 Quinones in Hydrogen Peroxide Synthesis and Catalytic Aerobic Oxidation Reactions 221 Alison E.Wendlandt and Shannon S. Stahl     14.1 Introduction 221     14.2 Chemistry and Catalysis: Anthraquinone Oxidation (AO) Process 223     14.3 Process Technology 227     14.4 Future Developments: Selective Aerobic Oxidation Reactions Catalyzed by Quinones 229     References 234     15 NOx Cocatalysts for Aerobic Oxidation Reactions: Application to Alcohol Oxidation 239 Susan L. Zultanski and Shannon S. Stahl     15.1 Introduction 239     15.2 Chemistry and Catalysis 241     15.3 Prospects for Scale-Up 247     15.4 Conclusions 249     References 249     16 N-Hydroxyphthalimide (NHPI)-Organocatalyzed Aerobic Oxidations: Advantages, Limits, and Industrial Perspectives 253 Lucio Melone and Carlo Punta     16.1 Introduction 253     16.2 Chemistry and Catalysis 254     16.3 Process Technology 257     16.4 New Developments 262     Acknowledgments 264     References 264     17 Carbon Materials as Nonmetal Catalysts for Aerobic Oxidations: The Industrial Glyphosate Process and New Developments 267     17.1 Introduction 267 Mark Kuil and Annemarie E.W. Beers     17.2 Chemistry and Catalysis 268 Mark Kuil and Annemarie E.W. Beers     17.3 Process Technology 270 Mark Kuil and Annemarie E.W. Beers     17.4 New Developments 274 Paul L. Alsters     17.5 Concluding Remarks 283     References 283     Part V Biocatalytic Aerobic Oxidation 289     18 Enzyme Catalysis: Exploiting Biocatalysis and Aerobic Oxidations for High-Volume and High-Value Pharmaceutical Syntheses 291 Robert L. Osborne and Erika M. Milczek     18.1 Introduction 291     18.2 Chemistry and Catalysis 293     18.3 Process Technology 302     18.4 New Developments 304     References 306     Part VI Oxidative Conversion of Renewable Feedstocks 311     19 From Terephthalic Acid to 2,5-Furandicarboxylic Acid: An Industrial Perspective 313 Jan C. van derWaal, Etienne Mazoyer, Hendrikus J. Baars, and Gert-Jan M. Gruter     19.1 Introduction 313     19.2 Chemistry and Catalysis 314     19.3 Process Technology 320     19.4 New Developments 325     19.5 Conclusion 327     List of Abbreviations 327     References 327     20 Azelaic Acid fromVegetable Feedstock via Oxidative Cleavage with Ozone or Oxygen 331 Angela Kockritz     20.1 Introduction 331     20.2 Chemistry and Catalysis 336     20.3 Prospects for Scale-Up 341     20.4 Concluding Remarks and Perspectives 342     References 344     21 Oxidative Conversion of Renewable Feedstock: Carbohydrate Oxidation 349 Cristina Della Pina, Ermelinda Falletta, and Michele Rossi     21.1 Introduction 349     21.2 Chemistry and Catalysis 351     21.3 Prospects for Scale-Up 362     21.4 Concluding Remarks and Perspectives 366     References 367     Part VII Aerobic Oxidation with Singlet Oxygen 369     22 Industrial Prospects for the Chemical and Photochemical Singlet Oxygenation of Organic Compounds 371 Veronique Nardello-Rataj, Paul L. Alsters, and Jean-Marie Aubry     22.1 Introduction 371     22.2 Chemistry and Catalysis 373     22.3 Prospects for Scale-Up 383     22.4 Conclusion 392     Acknowledgments 392     References 393     Part VIII Reactor Concepts for Liquid Phase Aerobic Oxidation 397     23 Reactor Concepts for Aerobic Liquid Phase Oxidation:Microreactors and Tube Reactors 399 Hannes P. L. Gemoets, Volker Hessel, and Timothy Noel     23.1 Introduction 399     23.2 Chemistry and Catalysis 400     23.3 Prospects for Scale-Up 413     23.4 Conclusions 417     References 417     Index 421