Liquid Phase Aerobic Oxidation Catalysis: Industrial Applications and Academic Perspectives

Liquid Phase Aerobic Oxidation Catalysis: Industrial Applications and Academic Perspectives

By: Shannon S. Stahl (editor), Paul L. Alsters (editor)Hardback

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Description

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.

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About Author

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.

Contents

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

Product Details

  • publication date: 31/08/2016
  • ISBN13: 9783527337811
  • Format: Hardback
  • Number Of Pages: 456
  • ID: 9783527337811
  • weight: 1114
  • ISBN10: 3527337814

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