Rights Contact Login For More Details
- Wiley
More About This Title Liquid Phase Aerobic Oxidation Catalysis -Industrial Applications and Academic Perspectives
English
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.
English
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.
English
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
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 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 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
Véronique 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 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
