Liquid Phase Aerobic Oxidation Catalysis: Industrial Applications and Academic Perspectives

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. INDICE: Preface XV .List of Contributors XVII .Part I Radical Chain Aerobic Oxidation 1 .1 Overview of Radical Chain Oxidation Chemistry 3Ive 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 15Manfred 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 33Johan 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 41Victor 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 69Damian 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 85Janelle 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 97Patrick Gamez .7.2 2,3,5–Trimethylhydroquinone as a Vitamin E Intermediate via Oxidation of Methyl–Substituted Phenols 106Jan Schütz and Thomas Netscher .References 109 .Part III Pd–Catalyzed Aerobic Oxidation 113 .8 Pd–Catalyzed Aerobic Oxidation Reactions: Industrial Applications and New Developments 115Dian 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 139Reinhard 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 159Yusuke 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 173Yoshiyuki 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 189Grigorii 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 209Ken 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 221Alison 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 239Susan 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 253Lucio 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 267Mark Kuil and Annemarie E.W. Beers .17.2 Chemistry and Catalysis 268Mark Kuil and Annemarie E.W. Beers .17.3 Process Technology 270Mark Kuil and Annemarie E.W. Beers .17.4 New Developments 274Paul 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 291Robert 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 313Jan 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 331Angela Köckritz .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 349Cristina 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 371Véronique 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 399Hannes P. L. Gemoets, Volker Hessel, and Timothy Noël .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

• ISBN: 978-3-527-33781-1
• Editorial: Wiley VCH
• Encuadernacion: Cartoné
• Páginas: 456
• Fecha Publicación: 31/08/2016
• Nº Volúmenes: 1
• Idioma: Inglés