Industrial Organic Chemicals -- Contents -- Preface -- Preface to the First Edition -- Preface to the Second Edition -- Acknowledgments -- Bryan Godel Reuben 1934-2012 -- List of Acronyms and Abbreviations -- Introduction: How to Use Industrial Organic Chemicals, Third Edition -- I.1 Why This Book Was Written and How It Is Structured -- I.2 North American Industry Classification System -- I.3 Units and Nomenclature -- I.4 General Bibliography -- I.4.1 Encyclopedias -- I.4.2 Books -- I.4.3 Journals -- I.4.4 Patents -- I.4.5 Statistics and Internet Sources of Information -- 1. The Evolution of the Organic Chemicals Industry -- 1.1 The National Economy -- 1.2 Size of the Chemical Industry -- 1.3 Characteristics of the Chemical Industry -- 1.3.1 Capital Intensity and Economies of Scale -- 1.3.2 Criticality and Pervasiveness -- 1.3.3 Freedom of Market Entry -- 1.3.4 Strong Regulation -- 1.3.4.1 European Legislation -- 1.3.4.2 Political Factors -- 1.3.5 High but Declining Research and Development Expenditures -- 1.3.6 Dislocations -- 1.4 The Top Companies -- 1.5 The Top Chemicals -- Endnotes -- 2. Globalization of the Chemical Industry -- 2.1 Overcapacity -- 2.1.1 Economic Cycles -- 2.2 Restructuring, Mergers, and Acquisitions -- 2.2.1 SuICIde of a UK Company -- 2.2.2 Private Equity -- 2.3 Participation in International Trade -- 2.4 Competition from Developing Countries -- Endnotes -- 3. Transporting Chemicals -- 3.1 Shipping Petroleum -- 3.2 Shipping Gas -- 3.3 Shipping Chemicals -- 3.3.1 Gases -- 3.3.2 Liquids -- 3.3.3 Solids -- 3.4 Health and Safety -- 3.5 Economic Aspects -- 3.6 Trade in Specific Chemicals -- 3.7 Top Shipping Companies -- Endnotes -- 4. Chemicals from Natural Gas and Petroleum -- 4.1 Petroleum Distillation -- 4.2 Shale Gas -- 4.2.1 Shale Gas Technology -- 4.3 Naphtha Versus Gaseous Feedstocks -- 4.4 Heavier Oil Fractions.

4.5 Steam Cracking and Petroleum Refining Reactions -- 4.5.1 Steam Cracking -- 4.5.2 Choice of Feedstock -- 4.5.3 Economics of Steam Cracking -- 4.6 Catalytic Cracking -- 4.7 Mechanisms of Steam and Catalytic Cracking -- 4.8 Catalytic Reforming -- 4.9 Oligomerization -- 4.10 Alkylation -- 4.11 Hydrotreating and Coking -- 4.12 Dehydrogenation -- 4.13 Isomerization -- 4.14 Metathesis -- 4.14.1 Metathesis Outside the Refinery -- 4.14.2 Mechanism of Metathesis -- 4.15 Function of the Refinery and the Potential Petroleum Shortage -- 4.15.1 Unleaded Gasoline and the Clean Air Act -- 4.16 Separation of Natural Gas -- 4.17 Oil from Tar Sands -- Endnotes -- 5. Chemicals and Polymers from Ethylene -- 5.1 Ethylene Polymers -- 5.1.1 Discovery of Low and High Density Polyethylenes -- 5.1.2 Low Density Polyethylene -- 5.1.3 High Density Polyethylene -- 5.1.4 Linear Low Density Polyethylene -- 5.1.5 Very High Molecular Weight Polyethylene -- 5.1.6 Metallocene Polyethylenes -- 5.1.7 Very Low Density Polyethylene -- 5.1.8 Bimodal HDPE -- 5.1.9 "Green" Polyethylene -- 5.2 Ethylene Copolymers -- 5.2.1 Chlorosulfonated Polyethylene -- 5.2.2 Ethylene-Vinyl Acetate -- 5.2.3 Ionomers -- 5.2.4 Copolymer from "Incompatible" Polymer Blends -- 5.2.5 Ethylene-Propylene Elastomers -- 5.2.6 Polyolefin Elastomers -- 5.3 Oligomerization -- 5.3.1 Dimerization -- 5.3.2 Ziegler Oligomerization of Ethylene -- 5.3.3 Other Ethylene Oligomerization Technologies -- 5.3.4 Shell Higher Olefins Process (SHOP) -- 5.4 Vinyl Chloride -- 5.5 Acetaldehyde -- 5.6 Vinyl Acetate -- 5.7 Ethylene Oxide -- 5.7.1 Ethylene Glycol -- 5.7.2 Proposed Non-Ethylene Oxide Processes for Ethylene Glycol Production -- 5.8 Styrene -- 5.9 Ethanol -- 5.10 Major Chemicals from Ethylene - A Summary -- 5.11 Lesser Volume Chemicals from Ethylene -- 5.11.1 Hydroformylation - Propionaldehyde, Propionic Acid, and n-Propanol.

5.11.2 Ethyl Halides -- 5.11.3 Acetaldehyde Chemistry -- 5.11.4 Metal Complexes -- 5.11.5 Ethylenediamine and Related Compounds -- 5.11.6 Ethylene Oxide and Ethylene Glycol Derivatives -- 5.11.6.1 Oligomers -- 5.11.6.2 Glycol Ethers and Esters -- 5.11.6.3 Ethylene Carbonate -- 5.11.6.4 Aminoethyl Alcohols (Ethanolamines) and Derivatives -- 5.11.6.5 Ethyleneimine -- 5.11.6.6 1,3-Propanediol -- 5.11.6.7 Ethylene Glycol Derivatives -- 5.11.7 Vinyl Chloride and Ethylene Dichloride Derivatives -- 5.11.8 Vinyl Fluoride and Vinylidene Fluoride -- 5.11.9 Ethylene Dibromide -- 5.11.10 Ethanol Derivatives -- 5.11.11 Vinyl Esters and Ethers -- Endnotes -- 6. Chemicals and Polymers from Propylene -- 6.1 On-Purpose Propylene Production Technologies and Propane Dehydrogenation -- 6.1.1 Propylene Via Enhanced Fluidized Catalytic Cracking -- 6.1.2 Propylene Via Selective C4/C5 Cracking -- 6.2 Main Polymers and Chemicals from Propylene -- 6.2.1 Propylene Polymers and Copolymers -- 6.3 Oligomerization -- 6.4 Acrylic Acid -- 6.4.1 Biorenewable Processes to Acrylic Acid -- 6.4.2 Acrylic Acid Markets -- 6.5 Acrylonitrile -- 6.5.1 Uses of Acrylonitrile -- 6.6 Cumene/Phenol and Cumene Hydroperoxide -- 6.7 Acetone and Isopropanol -- 6.7.1 Methyl Methacrylate -- 6.7.2 Methyl Isobutyl Ketone and Other Acetone Derivatives -- 6.8 Propylene Oxide -- 6.8.1 Other Propylene Oxide Processes -- 6.8.1.1 Acetoxylation of Propylene -- 6.8.1.2 Direct Oxidation -- 6.8.1.3 Use of Peracids -- 6.8.1.4 Electrochemical Processes -- 6.8.1.5 Biotechnological Approaches -- 6.8.2 Propylene Oxide Applications -- 6.9 n-Butyraldehyde and Isobutyraldehyde -- 6.9.1 Uses for Butyraldehyde, Isobutyraldehyde, and n-Butanol -- 6.9.2 Other Oxo Products -- 6.10 Major Chemicals from Propylene - A Perspective -- 6.11 Lesser Volume Chemicals from Propylene -- 6.11.1 Allyl Chloride and Epichlorohydrin.

6.11.2 Glycerol -- 6.11.3 Acrylamide -- 6.11.4 Acrolein -- 6.11.5 Acrylonitrile Derivatives -- Endnotes -- 7. Chemicals from the C4 Stream -- 7.1 Chemicals and Polymers from Butadiene -- 7.1.1 Tires -- 7.1.2 Styrene-Butadiene Elastomers -- 7.1.3 Polybutadienes and Other Elastomers -- 7.1.4 Acrylonitrile-Butadiene-Styrene Resins -- 7.1.5 Hexamethylenediamine -- 7.1.6 Lesser Volume Chemicals from Butadiene -- 7.1.6.1 Cyclization -- 7.1.6.2 Dimerization and Trimerization -- 7.1.6.3 Diels-Alder Reactions -- 7.1.6.4 Adipic Acid -- 7.1.6.5 1,4-Butanediol -- 7.1.6.6 trans-1,4-Hexadiene -- 7.1.6.7 Dimethyl-2,6-naphthalene Dicarboxylate -- 7.1.6.8 Butadiene Monoepoxide -- 7.2 Chemicals and Polymers from Isobutene -- 7.2.1 Methyl tert-Butyl Ether -- 7.2.2 Butyl Rubber -- 7.2.3 Polyisobutenes and Isobutene Oligomers and Polymers -- 7.2.4 tert-Butanol -- 7.2.5 Methyl Methacrylate -- 7.2.6 Lesser Volume Chemicals from Isobutene -- 7.3 Chemicals and Polymers from 1- and 2-Butenes -- 7.4 Chemicals from n-Butane -- 7.4.1 Acetic Acid -- 7.4.2 Maleic Anhydride -- 7.4.3 Succinic, Malic, Fumaric, and Tartaric Acids -- Endnotes -- 8. Chemicals from the C5 Stream -- 8.1 Separation of the C5 Stream -- 8.2 Isoprene -- 8.2.1 Natural Rubber -- 8.2.2 Vulcanization -- 8.2.3 Production of Petrochemical Isoprene -- 8.2.4 Applications of Isoprene -- 8.3 Cyclopentadiene and Dicyclopentadiene -- 8.4 Pentene-1 and Piperylene -- Endnotes -- 9. Chemicals from Benzene -- 9.1 Phenol -- 9.1.1 Phenolic Resins -- 9.1.2 Bisphenol A -- 9.1.2.1 Epoxy Resins -- 9.1.2.2 Polycarbonate Resins -- 9.1.2.3 Lesser Volume Uses for Bisphenol A -- 9.1.2.4 Environmental Problems -- 9.1.3 Cyclohexanone -- 9.1.4 Alkylphenols -- 9.1.5 Chlorinated Phenols -- 9.1.6 2,6-Xylenol/Cresols -- 9.1.7 Aniline from Phenol -- 9.2 Cyclohexane -- 9.2.1 Adipic Acid -- 9.2.1.1 Nylons from Adipic Acid -- 9.2.2 Caprolactam.

9.3 Aniline -- 9.3.1 4,40-Diphenylmethane Isocyanate -- 9.4 Alkylbenzenes -- 9.5 Maleic Anhydride -- 9.6 Chlorinated Benzenes -- 9.7 Dihydroxybenzenes -- 9.7.1 Hydroquinone -- 9.7.2 Resorcinol -- 9.7.3 Catechol -- 9.8 Anthraquinone -- 9.8.1 Hydrogen Peroxide -- Endnotes -- 10. Chemicals from Toluene -- 10.1 Hydrodealkylation, Disproportionation, and Transalkylation -- 10.2 Solvents -- 10.3 Dinitrotoluene and Toluene Diisocyanate -- 10.4 Lesser Volume Chemicals from Toluene -- Endnotes -- 11. Chemicals from Xylenes -- 11.1 o-Xylene and Phthalic Anhydride -- 11.1.1 Plasticizers -- 11.1.2 Alkyd Resins -- 11.1.3 Unsaturated Polyester Resin -- 11.2 m-Xylene and Isophthalic Acid -- 11.2.1 Uses of Isophthalic Acid -- 11.3 p-Xylene and Terephthalic Acid/Dimethyl Terephthalate -- 11.3.1 Oxidation of p-Xylene -- 11.3.2 Alternate Sources for Terephthalic Acid -- 11.3.3 Poly(ethylene terephthalate) -- 11.3.4 Lower Volume Polymers from Terephthalic Acid -- Endnotes -- 12. Chemicals from Methane -- 12.1 Hydrocyanic Acid -- 12.2 Halogenated Methanes -- 12.2.1 Chloromethane -- 12.2.2 Dichloromethane -- 12.2.3 Trichloromethane -- 12.2.4 Fluorocarbons -- 12.2.5 Tetrachloromethane and Carbon Disulfide -- 12.2.6 Bromomethane -- 12.3 Acetylene -- 12.3.1 1,4-Butanediol and 2-Methyl-1,3-propanediol -- 12.3.2 Lesser Uses for Acetylene -- 12.4 Synthesis Gas -- 12.4.1 Steam Reforming of Methane -- 12.4.2 Variants of Steam Reforming -- 12.4.3 Partial Oxidation of Hydrocarbons -- 12.4.4 Solid Feedstocks -- 12.4.5 Hydrogen -- 12.5 Chemicals from Synthesis Gas -- 12.5.1 Ammonia and Its Derivatives -- 12.5.1.1 The Crisis of Nitrogen Depletion -- 12.5.1.2 Ammonia Manufacture -- 12.5.1.3 Urea and Melamine Resins -- 12.5.2 Methanol -- 12.5.2.1 Formaldehyde -- 12.5.2.2 Acetic Acid -- 12.5.2.3 Acetic Anhydride -- 12.5.2.4 Methanol to Gasoline -- 12.5.2.5 Methanol to Olefins.

12.5.2.6 Lower Volume and Proposed Uses for Methanol.