Article No : a13_227
Hydrocarbons
KARL GRIESBAUM, Universit€at Karlsruhe (TH), Karlsruhe, Federal Republic of Germany
ARNO BEHR, Henkel KGaA, Dusseldorf,€ Federal Republic of Germany
DIETER BIEDENKAPP, BASF Aktiengesellschaft, Ludwigshafen, Federal Republic of Germany
HEINZ-WERNER VOGES, Huls€ Aktiengesellschaft, Marl, Federal Republic of Germany
DOROTHEA GARBE, Haarmann & Reimer GmbH, Holzminden, Federal Republic of Germany
CHRISTIAN PAETZ, Bayer AG, Leverkusen, Federal Republic of Germany
GERD COLLIN, Ruttgerswerke€ AG, Duisburg, Federal Republic of Germany
DIETER MAYER, Hoechst Aktiengesellschaft, Frankfurt, Federal Republic of Germany
HARTMUT Ho€KE, Ruttgerswerke€ AG, Castrop-Rauxel, Federal Republic of Germany
1. Saturated Hydrocarbons ...... 134 3.7. Cumene ...... 163 1.1. Physical Properties ...... 134 3.8. Diisopropylbenzenes ...... 164
1.2. Chemical Properties ...... 134 3.9. Cymenes; C4- and C5-Alkylaromatic 1.3. Production ...... 134 Compounds ...... 165 1.3.1. From Natural Gas and Petroleum ...... 135 3.10. Monoalkylbenzenes with Alkyl Groups
1.3.2. From Coal and Coal-Derived Products . . . . . 138 >C10 ...... 166 1.3.3. By Synthesis and by Conversion of other 3.11. Diphenylmethane ...... 167 Hydrocarbons ...... 139 4. Biphenyls and Polyphenyls ...... 168 1.4. Uses ...... 140 4.1. Biphenyl...... 168 1.5. Individual Saturated Hydrocarbons ... 142 4.2. Terphenyls...... 171 2. Olefins ...... 144 4.3. Polyphenyls ...... 172 2.1. Monoolefins ...... 144 5. Hydrocarbons from Coal Tar ...... 172 2.1.1. Properties ...... 145 5.1. Acenaphthene ...... 172 2.1.2. Production of Higher Olefins ...... 145 5.2. Indene ...... 174 2.1.2.1. Production from Paraffins ...... 146 5.3. Fluorene...... 175 2.1.2.2. Oligomerization of Lower Olefins ...... 149 5.4. Fluoranthene ...... 176 2.1.3. Uses of Higher Olefins...... 154 5.5. Phenanthrene...... 177 2.1.4. Economic Aspects of Higher Olefins .... 157 5.6. Pyrene ...... 178 2.2. Dienes and Polyenes...... 157 6. Toxicology and Occupational Health ... 179 2.2.1. Low Molecular Mass 1,3-Dienes ...... 157 6.1. Alkanes ...... 179 2.2.2. Synthesis of Dienes and Polyenes by 6.2. Alkenes ...... 180 Oligomerization...... 158 6.3. Alkylbenzenes ...... 180 2.2.3. Synthesis of Dienes and Polyenes by 6.4. Biphenyls and Polyphenyls ...... 181 Metathesis...... 159 6.5. Hydrocarbons from Coal Tar ...... 181 3. Alkylbenzenes ...... 160 6.5.1. Biological Effects ...... 181 3.1. Trimethylbenzenes...... 160 6.5.1.1. Carcinogenicity and Mutagenicity ...... 181 3.2. Tetramethylbenzenes ...... 161 6.5.1.2. Mammalian Toxicity and Toxicokinetics . 182 3.3. Penta- and Hexamethylbenzene ...... 162 6.5.1.3. Ecotoxicology ...... 182 3.4. Diethylbenzenes ...... 162 6.5.2. Safety Regulations...... 182 3.5. Triethylbenzenes and More Highly References ...... 182 Ethylated Benzenes ...... 162 3.6. Ethylmethylbenzenes (Ethyltoluenes)... 163