Catalysis underpins most modern industrial organic processes. It has become an essential tool in creating a 'greener' chemical industry by replacing more traditional stoichiometric reactions, which have high energy consumption and high waste production, with mild processes which increasingly resemble Nature's enzymes. Metal-Catalysis in Industrial Organic Processes is a definitive reference source, written by practising experts in the field, that provides detailed and up-to-date information on key aspects of metal catalysis. The major industrial processes, involving oxidation, hydrogenation,…mehr
Catalysis underpins most modern industrial organic processes. It has become an essential tool in creating a 'greener' chemical industry by replacing more traditional stoichiometric reactions, which have high energy consumption and high waste production, with mild processes which increasingly resemble Nature's enzymes. Metal-Catalysis in Industrial Organic Processes is a definitive reference source, written by practising experts in the field, that provides detailed and up-to-date information on key aspects of metal catalysis. The major industrial processes, involving oxidation, hydrogenation, carbonylation, C-C bond formation, metathesis and polymerization, and their mechanisms, are concisely discussed. In addition two appendices describe the basics of homogeneous and heterogeneous catalysis. Numerous exercises referring to problems of the catalytic processes, and research perspectives complete the book. "There is hardly any other field of chemistry that is so clearly connected to industrial application as organometallic chemistry and catalysis.....An interestingly written textbook that explains the most important metal-catalyzed industrial processes at a suitably thorough level, but is nevertheless compact enough to be read as a whole, promises to be a very useful resource." Angewandte Chemie International Ed., 2007, 46, 3791-3792 (Lukas J. GooBen) "The field of industrial catalysis is obviously enormous and yet has been well covered here in fewer than 300 pages. This makes the book an accessible work that describes many of the more important processes in sufficient depth, rather than an unwieldy tome. "A particularly appealing aspect of the book is the inclusion of 'discussion points' throughout the book. These would be useful, for instance, as themes for round-table discussions with advanced level undergraduate and postgraduate students, indeed I have used some of them for precisely this purpose. In some of the chapters these are supplemented with invaluable extra 'hints' to help get the ball rolling. In summary I wholeheartedly recommend this excellent textbook to anybody with an interest in catalysis, either from an industrial or academic perspective." Platinum Metals Review, 2007, 51 (4), 187-188 (Robin B Bedford)
Preface Glossary Chapter 1: Introduction - Catalysis in the Chemical Industry Sunley 1.1: Catalysis in the Chemical Industry 1.2: Selection of a Chemical Process: What Does the Catalyst Do? 1.3: Developing Metal-Catalysis - the Role of Fundamental Understanding References Chapter 2: Formation of C-O Bonds by Oxidation 2.1: Review - The Basic Chemistry of Oxygen 2.2: Cyclohexane Oxidation to Cyclohexanol and Cyclohexanone and to Adipic Acid: on the Way to Nylon-6,6 2.3: p-Xylene Oxidation to Terephthalic Acid. Polyethylene Terephthalate: on the Way to Fibres for Shirts 2.4: Ethylene Oxide by Ag-catalyzed Oxidation of Ethylene: for Antifreeze and Detergents 2.5: Propylene Oxide: to Biocompatible Propylene Glycol 2.6: Hydrogen Peroxide Route to Propylene Oxide 2.7: Asymmetric Epoxidation, Dihydroxylation and Sulfide Oxidation: New Routes to Chiral Agrochemicals and Pharmaceuticals 2.8: Acrolein and Acrylic Acid from Propylene: for Super-Absorbent Polymers, Paints, and Fibres 2.9: Methacrolein and Methacrylic Acid from Isobutene 2.10: Ammoxidation Reactions. Propylene to Acrylonitrile: for Engineering Plastics, Polymers 2.11: Maleic Anhydride and Phthalic Anhydride: for THF, Spandex, Swim-suits and Ladies' Tights 2.12: Silicalite Process to e-Caprolactam 2.13: Oxidation of Phenol to Catechol and Hydroquinone 2.14: Benzene Oxidation to Phenol: Making Phenolic Resins for Building 2.15: Oxidation Processes in which the Metal Directly Functionalizes the Olefinic Substrate 2.16: Enzymatic and Microbiological Oxidations. Microbial Hydroxylation of Progesterone Annex 1: Alkane Feedstocks. Alternative Routes to Acetic Acid and Acrylonitrile Annex 2: Adsorption Effects on the Catalytic Performances of TS-1. Zeolites as Solid Solvents References Chapter 3: Hydrogenation Reactions 3.1: Introduction and Basic Chemistry: Activation of Hydrogen and Transfer to Substrate Isomerization Reactions 3.2: Hydrotreating in Petroleum Chemistry 3.3: Mono-unsaturated Fatty Esters by Partial Hydrogenation of Natural Oils 3.4: Hydrogenation of Adiponitrile to Hexamethylenediamine 3.5: Making L-DOPA by Enantioselective Hydrogenation of Acetamidoarylacrylic Acids 3.6: Enantioselective Hydrogenation of N-Arylimines in the Synthesis of the Chiral Herbicide, (S )-Metolachlor 3.7: Isomerization Reactions: Diethylgeranylamine and Diethylnerylamine for the Production of (_)-Menthol 3.8: Enantioselective Hydrogen Transfer 3.9: Ethylbenzene Dehydrogenation to Styrene Discussion Points References Chapter 4: Syntheses Based on Carbon Monoxide 4.1: Introduction 4.2: Carbonylation Reactions of Alcohols and Esters 4.3: Hydroxy/Alkoxy-Carbonylation of Alkenes and Dienes 4.4: Polyketones 4.5: Oxidative Carbonylation of Methanol to Dimethyl Carbonate and Dimethyl Oxalate 4.6: Hydroformylation of Olefins 4.7: CO Hydrogenation Annex 1: Concerning the Mechanism of the Fischer-Tropsch Reaction Annex 2: Some Hints for Discussion Points References Chapter 5: Carbon-Carbon Bond Formation 5.1: Introduction 5.2: Alkylation and Related Reactions 5.3: Carbon-Carbon Bond Formation through Activation of Aryl- or Vinyl-Halide bonds: Fine Chemicals 5.4: Chemistry of Allyl Compounds. Butadiene as Substrate 5.5: Oligomerization of Olefins 5.6: Carbene Chemistry and Asymmetric Synthesis: Chrysanthemic Esters Annex 1: Devising New Synthetic Pathways Annex 2: Hints to Improve or to Develop Alternative Processes for the Synthesis of Aromatics Catalyzed by Transition Metals Annex 3: Perspectives in C-C Bond Forming Organic Syntheses References Chapter 6: Metathesis of Olefins 6.1: Introduction - History and Basic Chemistry of Metathesis 6.2: The Carbene-Metallacyclobutane Mechanism of Metathesis 6.3: Industrial Applications of Metathesis 6.4: Homogeneous Ruthenium Alkylidene Complexes 6.5: Speciality Polymers 6.6: Fine Chemicals and Pharmaceuticals 6.7: Recent Progress 6.8: Future Outlook References Chapter 7: Polymerization Reactions 7.1: An Introductory Overview 7.2: Industrial Aspects of Polyolefin Production 7.3: Solid-State Polymerization Catalysts 7.4: Soluble Olefin Polymerization Catalysts 7.5: Supported Metallocene Catalysts 7.6: Copolymerization of Linear and Cyclic Olefins 7.7: Copolymerisation of Olefins with Polar Monomers and with CO Annex 1: Polymer Stereochemistry Studied by 13C NMR Spectroscopy Annex 2: Stereospecific Polymerization of Conjugated Diolefins: Butadiene and Isoprene Annex 3: Some Hints to Help Start the Discussions Acknowledgements References Appendix 1: Basic Organometallic Chemistry Related to Catalytic Cycles References Appendix 2: Some Basic Aspects of Surface Science Related to Heterogeneously Catalyzed Reactions References Subject Index
Preface Glossary Chapter 1: Introduction - Catalysis in the Chemical Industry Sunley 1.1: Catalysis in the Chemical Industry 1.2: Selection of a Chemical Process: What Does the Catalyst Do? 1.3: Developing Metal-Catalysis - the Role of Fundamental Understanding References Chapter 2: Formation of C-O Bonds by Oxidation 2.1: Review - The Basic Chemistry of Oxygen 2.2: Cyclohexane Oxidation to Cyclohexanol and Cyclohexanone and to Adipic Acid: on the Way to Nylon-6,6 2.3: p-Xylene Oxidation to Terephthalic Acid. Polyethylene Terephthalate: on the Way to Fibres for Shirts 2.4: Ethylene Oxide by Ag-catalyzed Oxidation of Ethylene: for Antifreeze and Detergents 2.5: Propylene Oxide: to Biocompatible Propylene Glycol 2.6: Hydrogen Peroxide Route to Propylene Oxide 2.7: Asymmetric Epoxidation, Dihydroxylation and Sulfide Oxidation: New Routes to Chiral Agrochemicals and Pharmaceuticals 2.8: Acrolein and Acrylic Acid from Propylene: for Super-Absorbent Polymers, Paints, and Fibres 2.9: Methacrolein and Methacrylic Acid from Isobutene 2.10: Ammoxidation Reactions. Propylene to Acrylonitrile: for Engineering Plastics, Polymers 2.11: Maleic Anhydride and Phthalic Anhydride: for THF, Spandex, Swim-suits and Ladies' Tights 2.12: Silicalite Process to e-Caprolactam 2.13: Oxidation of Phenol to Catechol and Hydroquinone 2.14: Benzene Oxidation to Phenol: Making Phenolic Resins for Building 2.15: Oxidation Processes in which the Metal Directly Functionalizes the Olefinic Substrate 2.16: Enzymatic and Microbiological Oxidations. Microbial Hydroxylation of Progesterone Annex 1: Alkane Feedstocks. Alternative Routes to Acetic Acid and Acrylonitrile Annex 2: Adsorption Effects on the Catalytic Performances of TS-1. Zeolites as Solid Solvents References Chapter 3: Hydrogenation Reactions 3.1: Introduction and Basic Chemistry: Activation of Hydrogen and Transfer to Substrate Isomerization Reactions 3.2: Hydrotreating in Petroleum Chemistry 3.3: Mono-unsaturated Fatty Esters by Partial Hydrogenation of Natural Oils 3.4: Hydrogenation of Adiponitrile to Hexamethylenediamine 3.5: Making L-DOPA by Enantioselective Hydrogenation of Acetamidoarylacrylic Acids 3.6: Enantioselective Hydrogenation of N-Arylimines in the Synthesis of the Chiral Herbicide, (S )-Metolachlor 3.7: Isomerization Reactions: Diethylgeranylamine and Diethylnerylamine for the Production of (_)-Menthol 3.8: Enantioselective Hydrogen Transfer 3.9: Ethylbenzene Dehydrogenation to Styrene Discussion Points References Chapter 4: Syntheses Based on Carbon Monoxide 4.1: Introduction 4.2: Carbonylation Reactions of Alcohols and Esters 4.3: Hydroxy/Alkoxy-Carbonylation of Alkenes and Dienes 4.4: Polyketones 4.5: Oxidative Carbonylation of Methanol to Dimethyl Carbonate and Dimethyl Oxalate 4.6: Hydroformylation of Olefins 4.7: CO Hydrogenation Annex 1: Concerning the Mechanism of the Fischer-Tropsch Reaction Annex 2: Some Hints for Discussion Points References Chapter 5: Carbon-Carbon Bond Formation 5.1: Introduction 5.2: Alkylation and Related Reactions 5.3: Carbon-Carbon Bond Formation through Activation of Aryl- or Vinyl-Halide bonds: Fine Chemicals 5.4: Chemistry of Allyl Compounds. Butadiene as Substrate 5.5: Oligomerization of Olefins 5.6: Carbene Chemistry and Asymmetric Synthesis: Chrysanthemic Esters Annex 1: Devising New Synthetic Pathways Annex 2: Hints to Improve or to Develop Alternative Processes for the Synthesis of Aromatics Catalyzed by Transition Metals Annex 3: Perspectives in C-C Bond Forming Organic Syntheses References Chapter 6: Metathesis of Olefins 6.1: Introduction - History and Basic Chemistry of Metathesis 6.2: The Carbene-Metallacyclobutane Mechanism of Metathesis 6.3: Industrial Applications of Metathesis 6.4: Homogeneous Ruthenium Alkylidene Complexes 6.5: Speciality Polymers 6.6: Fine Chemicals and Pharmaceuticals 6.7: Recent Progress 6.8: Future Outlook References Chapter 7: Polymerization Reactions 7.1: An Introductory Overview 7.2: Industrial Aspects of Polyolefin Production 7.3: Solid-State Polymerization Catalysts 7.4: Soluble Olefin Polymerization Catalysts 7.5: Supported Metallocene Catalysts 7.6: Copolymerization of Linear and Cyclic Olefins 7.7: Copolymerisation of Olefins with Polar Monomers and with CO Annex 1: Polymer Stereochemistry Studied by 13C NMR Spectroscopy Annex 2: Stereospecific Polymerization of Conjugated Diolefins: Butadiene and Isoprene Annex 3: Some Hints to Help Start the Discussions Acknowledgements References Appendix 1: Basic Organometallic Chemistry Related to Catalytic Cycles References Appendix 2: Some Basic Aspects of Surface Science Related to Heterogeneously Catalyzed Reactions References Subject Index
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