HYDROCARBON CHEMISTRY
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1 HYDROCARBON CHEMISTRY George A. Olah Loker Hydrocarbon Research Institute and Department of Chemistry University of Southern California Los Angeles, California Ärpäd Molnär Department of Organic Chemistry Jözsef Attila University Szeged, Hungary A WILEY-INTERSCIENCE PUBLICATION JOHN WILEY & SONS, INC. New York / Chichester / Brisbane / Toronto / Singapore
2 CONTENTS Preface Introduction xv xvii 1 Introduction and General Aspects Hydrocarbons and Their Classes / Energy-Hydrocarbon Relationship / Hydrocarbon Sources and Separation / Natural Gas / Petroleum or Crude Oil / Heavy Oils, Shale, and Tar Sand / Coal and Its Liquefaction / Petroleum Refining and Upgrading / Distillation of Crude Petroleum / Hydrocarbon Refining and Conversion Processes / Finite, Nonrenewable Hydrocarbon Resources Hydrocarbon Synthesis / Syngas (CO H 2 )-based Fischer-Tropsch Synthesis / Methyl Alcohol Conversion / Carbon Dioxide Conversion / Direct Mediane Conversion / Chemical Nature of Hydrocarbon Conversion Reactions / Homolytic (Free-Radical) Reactions / Heterolytic (Ionic) Reactions / Use of Hydrocarbons / Refined Petroleum Products / Transportation Fuels / Chemicals and Plastics / 23 References and Notes / 24 v
3 VI CONTENTS 2. Hydrocarbons from Petroleum and Natural Gas 2.1. Cracking / Cracking Processes / Mechanism of Cracking / Comparison of Cracking Operations / Reforming / Thermal Reforming / Catalytic Reforming / 38 Hydroforming / 38 Metal-Catalyzed Reforming / Dehydrogenation with Olefin Production / Thermal Dehydrogenation / Catalytic Dehydrogenation to Alkenes / Practical Applications / 45 C-C 3 Alkenes / 45 C Alkenes / ,3-Butadiene and Isoprene / 46 Higher Olefins / 47 Styrene / Upgrading of Natural-Gas Liquids / Aromatics Production / Catalytic Dehydrogenation and Dehydrocyclization / Practical Applications / 53 References / Synthesis from C, Sources 3.1. Nature's Cj Chemistry and Chemical Reduction ofc0 2 / Fischer-Tropsch Chemistry / Catalysts / Mechanism / Related Processes / Direct Coupling of Methane / Catalytic Oxidative Condensation / High-Temperature Self-Coupling / Hydrocarbons through Methane Derivatives / Hydrocarbons through Methanol / 80 Methanol Synthesis / 80 Methanol Conversion to Hydrocarbons / Hydrocarbons through Methyl Halides / 89
4 CONTENTS VÜ References / Hydrocarbons through Sulfurated Methanes / Isomerization Acid-catalyzed Isomerization / Alkanes / 103 Mechanism / Arylalkanes / 111 Side-Chain Isomerization / 111 Positional Isomerization / Alkenes and Dienes / Base-Catalyzed Isomerization / Alkenes / The Reversible Acetylene-Allene Transformation / Metal-Catalyzed Isomerization / Alkanes / Alkenes / Pericyclic Rearrangements / Practical Applications / Isomerization of C 4 -C 6 Hydrocarbons / 132 Alkanes / 132 Alkenes Isomerization of Xylenes / 133 References / Alkylation Acid-Catalyzed Alkylation / Alkylation of Alkanes with Alkenes / Alkylation of Alkanes under Superacidic Conditions / 150 Alkylolysis (Alkylative Cleavage) / Alkylation of Alkenes and Alkynes / 154 Alkylation of Alkenes with Organic Halides / 154 Alkylation of Alkynes / 156 Alkylation with Carbonyl Compounds: The Prins Reaction / Alkylation of Aromatics / 157 Catalysts / 159 Alkylation with Alkyl Halides / 161
5 VÜi CONTENTS Alkylation with Alkenes / 166 Alkylation with Alkanes / 169 Alkylation with Alcohols / 172 Transalkylation and Dealkylation / Base-Catalyzed Alkylation / Alkylation through Organometallics / Miscellaneous Alkylations / Practical Applications / Isoalkane-Alkene Alkylation / Ethylbenzene / Cumene / Xylenes / p-ethyltoluene / Detergent Alkylates / 187 References / Addition Hydration / Alkenes and Dienes / Alkynes / Practical Applications / 202 Production ofalcohols by Hydration ofalkenes / 202 Production of Octane-Enhancing Oxygenates / 204 Acetaldehyde / HX Addition / Hydrohalogenation / 205 Alkenes / 205 Dienes / 209 Alkynes / Hypohalous Acids and Hypohalites / Hydrogen Cyanide / Practical Applications / 215 Ethyl Chloride / 215 Hydrochlorination of 1,3-Butadiene / 216 Vinyl Chloride / 216 Ethylene Chlorohydrin / 216 Propylene Chlorohydrin / 216 Adiponitrile / 217 Acrylonitrile / Halogen Addition / Alkenes / Dienes / 222
6 CONTENTS ix Alkynes / Practical Applications / 225 Vinyl Chloride / 225 Chlorination of1,3-butadiene / Ammonia and Amine Addition / Alkenes / Dienes / Alkynes / Hydrometalation / Hydroboration / 229 Alkenes / 230 Dienes / 233 Alkynes / Hydroalanation / Hydrosilylation / 235 Alkenes / 237 Dienes / 238 Alkynes / Hydrozirconation / Halometalation / Solvometalation / Solvomercuration / Oxythallation / Carbometalation / Cycloaddition / 245 References / Carbonylation Hydroformylation / Alkenes / Dienes and Alkynes / Synthesis of Aldehydes and Alcohols by the Oxo Reaction / Carboxylation / Koch Reaction / Carboxylation Catalyzed by Transition Metals / 277 Alkenes and Dienes / 278 Alkynes / 279 Alcohols / Carboxylation of Saturated Hydrocarbons / 280
7 X CONTENTS Practical Applications / 281 Neocarboxylic Acids / 281 Hydrocarboxymethylation of Long-Chain Alkenes / 281 Propionic Acid / 282 Acrylic Acid and Acrylates / 282 Acetic Acid / 282 Dimethyl Carbonate / Aminomethylation / 283 References / Oxidation-Oxygenation Oxidation of Alkanes / Oxidation to Alcohols and Carbonyl Compounds / 291 Autoxidation of Alkanes / 291 Oxidation ofmethane / 293 Oxidation of Other Saturated Hydrocarbons / Oxidations Resulting in Carbon-Carbon Bond Cleavage / 308 Metal Oxidants / 308 Electrophilic Reagents / 309 Oxygenolysis / Oxidation of Alkenes / Epoxidation / 313 Direct Oxidation with Stoichiometric Oxidants / 313 Metal-Catalyzed Epoxidation / 317 Epoxidation Catalyzed by Metalloporphyrins / 320 Asymmetrie Epoxidation / Reactions with Molecular Oxygen / 324 Autoxidation / 324 Reactions with Singlet Oxygen / Bis-hydroxylation / Vinylic Oxidation / 334 Oxidation to Carbonyl Compounds / 334 Vinylic Acetoxylation / Oxidative Cleavage / 340 Ozonation / 340 Other Oxidants / Allylic Oxidation / 346 Allylic Hydroxylation and Acyloxylation / 346
8 CONTENTS Xi Oxidation to a,ß-unsaturated Carbonyl Compounds / Oxidation of Alkynes / Oxidation to Carbonyl Compounds / Oxidative Cleavage / Oxidation of Aromatics / Ring Oxygenation / 353 Oxidation to Phenols / 353 Ring Acyloxylation / 357 Oxidation to Quinones / 358 Oxidation to Arene Oxides andarene Diols / 359 Oxidation with Singlet Oxygen / Oxidative Ring Cleavage / Benzylic Oxidation / 362 Oxidation of Methyl-Substituted Aromatics / 362 Oxidation of Other Arenes / 364 Benzylic Acetoxylation / Practical Applications / Oxidation of Alkanes / 366 AceticAcid / 366 Oxidation of Cyclohexane / 366 Oxidation of Cyclododecane / 367 sec-alcohols / Oxygenation of Alkenes and Dienes / 367 Ethylene Oxide / 367 Propylene Oxide / 369 Acetaldehyde and Acetone / 370 Vinyl Acetate / 371 l,4-diacetoxy^2-butene / 371 Acrolein and Acrylic Acid / 371 Methacrolein and Methacrylic Acid / Ammoxidation / 372 Acrylonitrile / 372 Other Processes / Oxidation of Arenes / 374 Phenol and Acetone / 374 Benzole Acid / 375 Terephthalic Acid / 375 Maleic Anhydride / 376 Phthalic Anhydride / 378 Anthraquinone / 380
9 XÜ CONTENTS References / Heterosubstitution Electrophilic (Acid-Catalyzed) Substitution / Substitution of Alkanes / 415 Halogenation / 415 Nitration / 416 Sulfuration / Substitution of Aromatic Hydrocarbons / 417 Halogenation / 418 Nitration / 419 Sulfonation / Practical Applications / 422 Chlorobenzene / 422 Nitration ofbenzene and Toluene / 422 Sulfonation ofbenzene and Alkylbenzenes / Free-Radical Substitution / Halogenation of Alkanes and Arylalkanes / 423 Chlorination of Alkanes / 424 Fluorination of Alkanes / 426 Side-Chain Chlorination of Arylalkanes / Allylic Chlorination / Sulfochlorination / Nitration / Practical Applications / 430 Chlorination of Alkanes / 430 Side-Chain Chlorination of Toluene / 431 Allyl Chloride / 432 Sulfochlorination of Alkanes / 432 Nitroalkanes / Amination / Heterosubstitution through Organometallics / Transition Metals / Alkali Metals and Magnesium / 435 References / Reduction-Hydrogenation Heterogeneous Catalytic Hydrogenation / Catalysts / Hydrogenation of Alkenes / 447
10 CONTENTS XÜi Mechanism / 448 Stereochemistry / Hydrogenation of Dienes / Transfer Hydrogenation / Hydrogenation of Alkynes / Hydrogenation of Aromatics / Homogeneous Catalytic Hydrogenation / Catalysts / Hydrogenation of Alkenes and Dienes / 460 Mechanism / 460 Selectivity and Stereochemistry / 462 Asymmetrie Hydrogenation / Hydrogenation of Alkynes / Hydrogenation of Aromatics / Chemical and Electrochemical Reduction / Reduction of Alkenes / Reduction of Alkynes / Reduction of Aromatics / 473 Mechanism / 474 Selectivity / Ionic Hydrogenation / Hydrogenation of Alkenes and Dienes / Hydrogenation of Aromatics / Hydrogenolysis of Saturated Hydrocarbons / Metal-Catalyzed Hydrogenolysis / Ionic Hydrogenolysis / Practical Applications / Selective Hydrogenation of Petroleum-Refining Streams / 489 C 2 Hydrorefining / 489 C 3 Hydrorefining / 489 C 4 Hydrorefining / 489 Gasoline Hydrorefining / Cyclohexane / Various Hydrogenations / 491 References Metathesis Acyclic Alkenes / Ring-Opening Metathesis Polymerization / 512
11 XiV CONTENTS Practical Applications / 515 References / Oligomerization and Polymerization Oligomerization / Acid-Catalyzed Oligomerization / 524 Practical Applications / Base-Catalyzed Oligomerization / Metal-Catalyzed Oligomerization / 528 Cyclooligomerization / 530 Practical applications / Polymerization / Cationic Polymerization / Anionic Polymerization / Free-Radical Polymerization / Coordination Polymerization / 550 Catalysts / 550 Active Centers and Mechanisms / 554 Stereoregular Polymerization of Propylene / 558 Stereoregular Polymerization ofdienes / Conducting Polymers / Practical Applications / 570 Ethylene Polymers / 570 Polypropylene / 572 Polybutylenes / 572 Styrene Polymers / 573 Polydienes / 575 References / 575 Index 595
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