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Home , Acrylonitrile, Dehydrogenation, Sulfolene

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ABR (~) 179 to 142 ABS (Acrylonitrile-butadiene-) 51, Adipic acid 161 (t) from bezene 14(f) from butadiene 12(f) from 100 from cyclohexane 40 from oxidation 88(t) from propene 11 (f) from (Wacker process) 87-90 hexamethylenediamine from 40 Acetic acid 14(f) from acetaldehyde oxidation 100 from acrylonitrile 41 from carbonylation 128, 136-137 from adipic acid 154 from butadiene -154 from cumene 76 from isopropanol dehydrogenation 65 from Oxo 42 from propene oxidation 97 from olefins by hydration 140-143 111ethyl isobutyl ketone from 153-154 linear, production 176 from 153 Alfin Catalysts 179 Acetoxylation 90-92 Alkyd resins 14(f), 16(f) 90, 149 Alkylamines from and alkyl halides 82 acrylonitrile from 150 from ammonia and methanol 81 vinyl acetate from 149 monomethylamine 81 vinyl chloride from 149 Alkylation reactions Acetylsalicylic acid 1 amines with methanol 81 11 (f) ammonia and amines with alkyl halides 80- from propene 92 81 Acrylicacid 11 (f), 92, 149-150 74-79 from acetylene 150 carbon 66 from ethylene 150 catalysts 67-71 from 150 hereto 66 from propene oxidation 92,149 isobutane 72-74 Acrylonitrile phenol with 79 from actaldehyde 151 phenol with methanol 80 from acetylene 95, 151 toluene with methanol 80 from propene 95 Alkyl halides 67,82 hydrodimerization 41 ammonia and amine alkylation 67 Activation energy 19 a-halo acids 82 Activity, catalytic 182 Alkylphenols 80 Addition reactions Allyl chloride from propene chlorination 151 ammonia to 144 Aminoundecanoic acid 173 chlorine to ethylene 147 Ammonia to acetone 153 nitrate from 126 to acetylene 151 from synthesis gas 18, 125-126 hydrogen cyanide to butadiene 147 synthesis of 125 hydrogen cyanide to ethylene oxide 151 urea from 126 to acetylene 148 Ammoxidation water to ethylene 140 propene 95 water to ethylene oxide 143 108 water to olefins 140-14 3 Aniline production 14(f),42 195 196 INDEX

Anionic 167-168 Catalysts Anthraquinone from oxidation 107 activity 182 API (gravity) 5 bonding theories 23-26 Aromatization reactions 55-59 calcination of 185 Associated gas 2 characterization of (heterogeneous) 186 analysis 2(t) characterization of (homogeneous) 190- treatment, acid gases, humidity 2 191 coordination 23, 168 Benzene coordination numbers 18-20 alkylation with olefins 74-76 heterogeneous 19 alkyl benzene sulfonates 76 hetergenized homogeneous 21 chemicals from 14(f) homogeneous 21 cumene from 75 mechanical strength 186 detergent alkylates from 76-79 -bound metal complexes 22 detergent alkylate properties 77(t) pore size and pore size distribution 186 from 74 preparation (of heterogeneous) 183-185 from toluene disproportionation 59 preparation (of homogeneous) 190 from toluene dealkylation 59 stability 28, 183 hydrogenation of 39 structure' and reactivity 20 from 104 surface analysis of 186 Pacol process for linear alkylates 78(f) 54-63 phenol from 102 catalysts 55-62 Benzoic acid process 62-63 from benzene 103 reactions 55 hydrogenation of 40 Cationic polymerization 166-167 Benzothiophene, hydrodesulfurization of 43 Chloroprene polymerization 180 Bisphenol A 76,174 Coal Bituminous coal 6 gasification of 109 Bituminous sands 8 H/C ratio 6(t) Athabasca bitumen analysis 8(t) hydrogenation 49 Butadiene rank 6 analysis 53 Coordination compounds 23 adiponitrile from 154 in polymerization 168 chemicals from 12(f) , alternating, block, random 157 copolymers of 179 Cossee and Arlman, steretspecific polymeriza• polymerization of 168, 179 tion 170 production 50 Cresol, from toluene alkylation with methanol n-Butanal 68 n-butanol from 129 Crosslinking of 159 1,4-Butanediol 12(f) Crude oils 4-6 analysis 5(t) butadiene from 50 classification 4 in alkylation of isobut?ne 72 Crystal field theory for bonding in coordination production of I - 175 compounds 25 Butyl rubber 51 energy levels of d orbitals 25(t) Cumene 75 Caprolactam 39,40 from benzene alkylation with propene 75 polymerization 157, 173 hydroperoxide 165 Carbonylation reactions Cyclohexane, dehydrogenation of 56 of ethylene 135 Cyclohexane carboxylic acid to E-caprolactam of methanol 136-137 40 Monsanto process 137(f) Cyclohexanol from phenol 39 Cylcooctadiene from butadiene 12(f) definition 19 Cyclopentene polymerization 173, 180 heterogeneous 19 homogeneous 21 Dealkylation 59 INDEX 197

Dehydrogenation hydration of 143 of alcohols 64-65 Ethylhexanol of C-4 and C-5 and alkenes 50-52 from n-butanal 129 of ethanol 64 in esterification of phthalic anhydride 105 of ethylbenzene 63-64 of higher n-alkanes 52-54 Formaldehyde of isopropanol 65 from methanol dehydrogenation 64 of methanol 64 from methanol oxidation 98 Dichlorobutene 25 Urea-formaldehyde resins 127 Dichloroethane dehydrochlorination to vinyl- Fischer-Tropsch synthesis 118-124 chloride 147 mechanism 120 1,4-Dicyanobutene from butadiene 154 product distribution 124(t) Diethylbenzene 74 product selectivity 119 Dihydronaphthalene, in hydrogenation of coal Free radial polymerization 165 49 Dimerization of olefins 146 Gases I-butene from ethylene 175 associated 2(t) Dimethylarnine 81 natural 2(t),2-3. Dimethyl terephthalate 106 synthesis 17, 115 Disproportionation of toluene 59 Gas hourly space velocity 182 Elimination reactions 138 from epichlorohydrin 152 160 from fatty acids 152 Epichlorohydrin from propene 151 Epoxy resins 151 n-Hexane, reforming of (analysis) 56(t) Ethane cracking for ethylene 9,9(t) Hexarnethylenediarnine Ethanol (Ethyl ) from ethylene hydra• from hydrodirnerization of acrylonitrile 41 tion 140-141 from hydrogenation of adiponitrile 41 Ethanolamine Hydration 140-143 from ethylene oxide 144 ethylene 141 natural gas treatment 3 ethylene oxide 142 Ethylbenzene production 74 process for ethylene using heterogeneous Ethylene catalysts 141 (f) acetaldehyde from 87 process for ethylene using sulfuric acid in alkylation reactions 74 141(f) carbonylation of 135 propene 142 chemicals from 10(f) Hydrocracking 46-48 ethylbenzene from 74 catalysts 47 ethylene oxidefrom 85 product analysis from a hydrocracking unit from cracking 9(t) 47(t) hydration of with heterogeneous catalysts reactions 46-47 141(f) Hydrocyanation hydration to ethanol 140 acetone 153 linear polyethylene from 177 butadiene 155 oxidative carbonylation of 128 Hydrodealkylation of toluene 48 sulfuric acid hydration process of 141 Hydrodenitrogenation 45-46 polymerization 165,177 Hydrodesulfurization 43-45 Hydrodimerization, acrylonitrile to adiponitrile from ethylene oxide 143-144 41 from synthesis gas 17 Hydroformylation (see Oxo process) glycol ethers 144 commercial processes for propylene 130 Ethylene oxide mechanism 132-134 from 150 olefins 42, 129-134 ethanolamines from 144 Hydrogen ammonia synthesis 18,125 Ethylene glycol from 143 Hydrogen donor process 49 from ethylene 85-87 Hydrogenation 198 INDEX

adipic acid 40 Methacrylic acid 153 adiponitrile 41 Methanol aldehydes and ketones 42 alkylation of ammonia and amines 81 alkenes and 43 alkylation of phenol 80 aromatic compounds 38-40 alkylation of toluene 80 benzene 39 carbonylation to acetic acid 136 benzoic acid 40 dehydrogenation 64 catalysts 36 homologation to ethanol 124 coal and coal liquids 43,49 MTBE from 143 hexamethylenediamine 41 oxidation 97 nitrobenzene 42 synthesis 115-11 7 phenol 39 synthesis conditions 116(t) reactions 37-50 Methanol to gasoline process (MTG) 123 Hydrogenolysis 81 compounds 45 Methyl-I-butyl ether from methanol and iso- compounds 43 butene 143 Hydroliquefaction Methylisobutyl ketone 153-154 coal and coal liquids 49-50 Methylmethacrylate from acetone 153 catalysts 49 Methylphenols 80 Hydroprocessing Molecular orbital theory (coordination com- coal liquids 43, 49 pounds) 25 hydrodenitrogenation 45-46 Monochlorobenzene 14 hydrodesulfurization 43-45 156 Monomethylamine 81 Indole, hydrodenitrogenation 46 Monsanto carbonylation process 137 (f) Initiators 156 MTG process 124 Insertion reaction 32,169 Isobutane Naptha alkylate properties 73(t) catalytic reforming of 54-59 alkylation with isobutene 72 composition 5 alkylation with propene and butenes 73 phthalic anhydride from 105 Isobutene 11 Natural gas in alkylation of isobutane 72 acid gases in 4 MTBE from 143 analysis 2(f) polymerization with cationic initiators 166 analysis of treated gas 4(f) Isoprene heavy hydrocarbons in 3 from C-5 alkenes 51-52 humidity removal 3 polymerization 168, 179 steam reforming of 110-114 rubber (NBR) 51 dehydrogenation to acetone 65 Nitrobenzene, hydrogenation to aniline 42 from hydration of propene 142 6 14(f), 15(f), 157 Isopropylbenzene (see cumene) 14,75 Nylon 66 (f), 40, 161(t)

KAacid 14 Oil sands (see also sands) 8 Oil shale Ligands, crystal field theory 24, 25 analysis 13(t) Linear alcohols from ethylene 176 composition 7 Linear alkyl benzene a-Olefins properties 77(t) for alkylating benzene 76 sulfonates 14,77 production of 176 Liquid hourly space velocity (LHSV) 182 Oligomerization ethylene 176 Maleic anhydride from benzene oxidation olefins 146 101(t),104 Oligomers 158 Mercaptans, hydrodesulfurization of 43 Oxidation Mesityloxide 153 anthraquinone 100 INDEX 199

aromatic hydrocarbons 101(t) from isoprene using n-butyllithium 168 ethylene 85-88 geometrical isomers 180 natural gas 4 Polymerization Oxidative addition 23 addition 163-168 Oxidative carbonylaticm 128 condensation 163 Oxo process (see also hydroformylation) 17, coordination 168 129-134 Free radical 165 Commercial processes for propylene 130 ring opening 17 3 Ruhrchemie Oxo process 131 (f) techniques, bulk, emulsion, solution, suspen• Shell Oxo process 131 (f) sion 174 UCC Oxo process 131 (f) polymers addition, condensation 157 Pacol process for linear alkylbenzene produc- branched, linear 158 tion 78(f) polymer-bound metal complexes 22(t) Partial oxidation, hydrocarbons 110 termination of 164,167,172 Pauling linus, valency bond theory 24 160, 161 (t) Peat 6 thermosetting 160 Peracetic acid from acetaldehyde oxidation Polymethylenemethllcryiate 161 145 Polypropylene . Phenol isotactic, mechanism 171 alkylation 79-80 production 178 . (ormaldehyde resins 159 properties 178(t) frbm benzene 14(t),102 tactic forms 169(f) fromcumene 72 Polypropylene glycol 145 from toluene 103 from propylene oxide 145 Phenylethyl alcohol 1 Polystyrene 161 Phthalic anhydride polymer-bound metal complexes from 22 from and o-xylene 101(t) 76 plasticizers from 105 Polyvinyl acetate 161 production 105 Polyvinyl chloride 161 Phthalonitrile 16(f) Propene acetone from 97 thermoplastics, properties 161, 162(t) acrylic acid and acrolein from 92 thermosetting 160 acrylonitrile from 95 Plexiglas 153 alkylation of benzene with 75 Polyacetals 162 alkylation of isobutane with 72 Polyamides allylchloride from 151 from amino acids and lactams 163 chemicals from 11 (f) nylon 6 157 hydration of 142 nylon 66 40 hydrocarbonylation of 129,130(1) mechanism 132-134 by Jl-allyl complexes 168 oxidation 95 production 179 polymerization 171, 17 8 Polybutyleneterephthalate 162(t),163 Propylene, oxide from 95 Polycarbonates 104, 162(t) from ethylene hydrocarbonyla- Polychloroprene 180 tion 135 Polysters 16,106,163 n-Propylbenzene 76 Polyethylene Propylene (see propene) by free radical polymerization 165 Propylene glycol from propylene oxide 145 linear, production 177 Propylene oxide from propylene oxidation properties 177(t) 95-96 Polyethylene terephthalate 158,162 Pyridine, hydrodenitrogenation of 45 Polyformaldehyde 158 Pyrole, hydrodenitrogenation of 45 Polyhexamethylenediamine 161 Polyisoprene 179 Raschig-Hooker process for phenol 102 copolymers 180 Reactors 187-192 200 INDEX

differential 188 oxidation to benzoic acid and phenol 103 integral 187 Trimethylamine 82 stirred tank 191 Trimethylpentane 72 tubular 192 Trioxane from formaldehyde 158 Reductive elimination 31 Reforming, catalytic 54-62 Urea production 126 catalysts 55 urea-Formaldehyde resins 127 process 60(f), 62(f) product analysis 61 (t) Valence bond theory 24 reactions 55-62 Vinyl acetate Residence time 182 from acetylene and acetic acid 149 from ethylene and acetic acid 90 Salicylic acid 1 from methanol and acetic acid 149 acrylonitrile - styrene 161 from methanol and synthesis gas 17,91 SBR (styrene - butadiene rubber) 50, 179 Vinyl chloride Shale oil 7 from acetylene 148 Selectivity 182 from ethylene oxychlorination 147 Silica, acid catalysts 68, 140 oxychlorination process 148(f) Steam reforming 110-114 Vinyl fluoride catalysts 112 from acetylene 148 natural gas 113 from vinyl chloride 148 process 113 Vulcanization 159 raw synthesis gas composition 114(t) Styrene Wacker process 87-90 copolymers with butadiene 157, 161(t), 179 mechanism 88 from ethylbenzene dehydrogenation 63 process conditions 87, 88(t) polymerization 167 Water-gas shift reaction 110 Suberic acid from butadiene 12(f) Substitution reactions 138 from butadiene chemicals from 16(f) Synthesis gas 17, 109 from catalytic reforming 54 catalysts 112 from toluene alkylation with methanol 80- composition 114(t) 81 methanol from 115 from toluene disproportionation 51 production and purification 110-111 thermodynamic equilibrium values 81(t) production economics by different routes o-Xylene, phthalic anhydride from 16(f),105 111(t) m-Xylene, isophthatic acid from 16(f) reactions 17-18 p-Xylene Synthetic crudes 7,35 ammoxidation 108 from coal liquefaction 7 terephthalic acid from 16(f),106 from oil shales 7 Synthetic fibers 160 Yield 182

Tar sands 8 Zeolites 124 analysis 8(t) acidity 70 polymers 160 benzene alkylation 74 properties 161-162(t) phenol alkylation 80 Terephthalic acid pore dimensions 70(t) (f) from p-xylene oxidation 16(f), 106-107 Sodalite unit 69 oxidation conditions 101(t) structural units 69 Tetralin for coal hydrogenation 49 synthesis 68 Thiophene, hydrodesulfurization 43 Ziegler catalysts 168-169 Toluene a -olefins I 76 alkylation with methanol 80 ethylene oligomerization 77,176 chemicals 15(f) linear alcohols 176 dealkylation (hydrodealkylation) 48,59 propylene polymerization 171 disproportionation 59