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APPENDIX 1.
U.S. Energy Conversion Factors
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APPENDIX 2.
Chemical Nomenclature
465
466 APPENDIX 2
Appendix 2. Chemical Nomenclature
Most of the chemicals referred to in this book have been called by their traditional names, which are still principally used by industrial researchers and by U.S. scientists. In contrast, these chemicals have systematic IUPAC (International Union of Pure and Applied Chemistry) names, which are widely used by European scientists, as well as by many other non-U.S. chemists and engineers. IUPAC has study groups and committees that continuously study the clarification and systematization of the names for chemical compounds, and their recommendations are published in the journal of Pure and Applied Chemistry. The following papers are of particular interest:
1. "Nomenclature of Organic Chemistry," Pure App1. Chern., 11: 1 (1965).
2. M. L. McGlashan, "Manual of Symbols and Terminology for Physicochemical Quantities and Units," Pure App1. Chern., 21:1 (1970).
3. J. Chatt, "Nomenclature of Inorganic Chemistry. 11.2 The Nomenclature of Hydrides of Nitrogen and Derived Cations, Anions, and Ligands," Pure App1. Chem., 54: 2545 (1982).
4. W. H. Powell, "Revision of the Extended Hantzach-Widman System of Nomenclature for Heteromonocycles," Pure Appl. Chem., 55:409 (1983).
5. v. Gold, "Glossary of Terms used in Physical Organic Chemistry," Pure App1. Chem., 55:1281 (1983).
Examples of pertinent chemical compounds are given below so that the traditional name can be compared with the IUPAC name. It will be evident that in some cases, e.g. anhydrides, the IUPAC name is hardly ever used, while in other cases, e.g. simple aldehydes, the usage is fairly evenly divided.
Traditional Name
Acetaldehyde Acetaldehyde dimethylacetal Acetic acid Acetone Acrolein or Acrylaldehyde Acrylonitrile Benzil or Diphenyldiketone Biacetal Butyraldehyde Caprolactam or 1,6-Hexanolactam Chloroform Crotonaldehyde Cumene Diacetone alcohol
IUPAC Name
Ethana1 l,l-Dimethoxyethane Ethanoic acid Propanone 2-Propen-l-al Propenonitrile 1, 2-Diphenylethan-l,2-dione 2,3-Butanedione Butanal 6-Hexanelactam Trichloromethane 2-buten-l-al Isopropylbenzene 4-Hydroxy-4-methylpentan-2-one
APPENDIX 2
Traditional Name
Diethanolamine Dimethyl terephthalate
Ethylbenzene Ethylene glycol Formaldehyde Formamide Formic acid Glyceraldehyde Glycerine or Glycerol Glycolaldehyde or
Glycolic aldehyde or Hydroxyacetaldehyde
Glyoxal Hemiacetal Hexamethylenediamine Isobutyryl chloride or
Isopropyl carbonyl chloride Isopropyl alcohol 2,5-Lutidine or
2,5-Dimethylpyridine Maleic anhydride Methacrylic acid Methyl acetate Methyl acetoacetate Methylethylketone Pentaerythritol Phthalic anhydride
2-Picoline or a-Picoline or 2-Methylpyridine
Propylene Stilbene Styrene Vinyl acetate Vinyl chloride o-Xylene p-Xylene
IUPAC Name
Bis(2-hydroxyethyl)amine Dimethyl-l,4-benzene-
dicarboxylate Phenyl ethane l,2-Ethanediol Methanal Methanamide Methanoic acid 2,3-Dihydroxypropanal l,2,3-Propane-triol 2-Hydroxyethanal
Ethanedial l-Methoxyethanol l,6-Diaminohexane 2-Methylpropanoyl chloride
2-Propanol 2,5-Dimethylazine
467
cis-Butendioic anhydride 2-Methyl-2-Propenoic acid l-Methoxyethanal l-Methoxybutan-l,3-dione Butanone Tetrakis(hydroxymethyl)methane l,2-Benzene-dicarboxylic
anhydride 2-methylazine
Propene l,2-Diphenylethene Phenylethene Ethenylethanoate Chloroethene l,2-Dimethylbenzene l,4-Dimethylbenzene
INDEX
Acetate esters, 84, 226, 263, 446 Acetaldehyde
condensation, 273 synthesis, 262
Acetic acid, 250, 263 Acetic anhydride, 15 Acidity function of aqueous HF,
235 Acyl
halides, 233 intermediates, 271, 301
Alcohol/ester fuels, 81-96 costs, 94 production, 86-89
Alcohol/gasoline blends, 92 Aldehyde intermediates, 204-210 Aldol
condensation, 203 products, 263
Alkaline earth oxides, 105 Alkanolamines, 443 Alkanols, 84 Alkoxide formation, 367 Alkoxyacetic acid, 229 Alkylation
of amines, 434-444 in petroleum industry, 227 of pyridine, 438
Alkylbenzenes, 159-160 Alkylpyridines, 442 Alloy catalysts, 67 Alpha-elimination, 332 Alpha olefins, 193 Alpha parameter, 137 Amberlyst 15, 199, 309, 388 Ammonia, 9
synthesis catalyst, 135
Anaerobic preservation, 251 Antiknock compounds, 307 Aromatics
formed from ethylene, 156-159 Azeotropes, 311, 445
Backbonding, 113 Backmixed reactor
single, 256 two stage countercurrent, 256
Backshifting, 41 Barrel
gallons in, 7 per stream day, 311
Benfield process, 44 BF3, 224 Bifunctional catalyst, 100, 151 Bi-Gas process, 46 Biomass
to methanol, 47 to synthesis gas, 37-50
Burnout studies, 344
Cl-C3 alcohols, 81-96 homologation of, 274
Cl-C3 esters, 81-96 Cl-C3 olefins, 403 Cl-C3 paraffins, 403 Cannizzaro reaction, 224 Carbamates, 444 Carbenium ions, 331 Carbomethoxylation, 193 Carbon dioxide
adsorption, 105 effect on Fischer-Tropsch,
342-349
469
470
Carbon monoxide adsorption
on copper oxide, 104 isotherms, 61 on metals, 98-99 on oxides, 103 on zinc oxide, 104
relative cost, 29 Carbon tetrachloride, 430 Carbonium ion, 229, 277, 365,
395, 408, 456-458 Carbonyl,
IR bands of, 104 Carbony1ation, 201, 205
of C2-C4 alcohols, 276 of C3-C4 alcohols, 279 of formaldehyde, 224-236 metal-catalyzed, 225 of methanol, 249-260, 267 pathways, 280 techniques, 235
Carboxyl, 103 Carboxylation, 196, 245 Catacarb, 44 Catalytic cracker, 310 CeCu5, 70 CeCuZn, 70 CeNi5, 65 Chabazite, 325 Chain growth, 171 Chain growth probability, 143 Chemicals
connnodity, 9 production of, 3 specialty, 32
Chemisorption measurements, 55, 161
Chlorination, 420-427 of methyl chloride, 425 processes for, 421
Chloroform, 429 Ch10romethanes, 419-431 CRx species, 142 Coal, 13-16, 29
anthracite, 14-15 depletion, 23 gasification, 44 to methanol, 47 production, 14-15 slurry, 23, 46
Coal (continued) to synthesis gas, 37-50
CO (see carbon monoxide) Cobalt
INDEX
carbonyl catalysts, 203-219, 262, 287
on copper-based catalysts, 53-63 -zinc oxide catalysts, 60 -ZSM-5, 154, 156
Coking, 40, 327, 354, 423 CoMo, 38
sulfided, 44 Consumption of energy, 8 CoO/ZnO/A1203, 54 Copper
catalysts, 237, 239, 435, 447 chromite catalyst, 104, 238
COSORB process, 254 Crude oil (see also Petroleum)
costs, 9, 29 gasification of, 42 refined products of, 8 source of US, 12 to synthesis gas, 43
Cu(CO>3+, 226 CuO/Cr203/A1203' 54 Cu/ZnO, 31, 3~, 108, 240, 447 CuO/ZnO/A1203, 54, 70, 240 Cyclopentylmethanol, 205
Deactivation, 241 Decarboxylation, 241 Dehydration
of alcohols, 263, 362 catalysts, 363-377, 434
Dehydrogenation of alcohols, 292, 366
Deuterium adsorption, 98 DGA process, 44 Dicyclopentadiene, 203 Dicyclopentadienedimethanol, 203 Diels-Alder reaction, 204 Diesel fuel, synthesis, 148 Difunctional compounds, 243 Diglycolic acid, 227, 230, 231 Diisopropylamine, 449 Dimethyl terephthalate, 446 Dimethylether, 407 Disproportionation, 451 d-orbitals, 187
INDEX
E1 elimination, 277, 365 Economic data
of chloromethane process, 432 of formic acid process, 258 of methy1tertiarybuty1 process,
314-318 of tertiaryamy1methy1 process,
315-318 Electrical power, 4-7
cost estimates, 6 generation, 27
Energy chemical, 41 consumption, 8, 19, 27 conversion factors, 465 production of, 3 sources of, 3-4, 20 supply, 21 usage, 5, 16
conservation, 1 efficiency, 17 forecasts, 18, 25-27 growth, 19
Ester formation, 82, 197, 307-322 fuels, 81
Esterification, 221, 238, 263 of carboxylic acids, 445
Ethanol dehydration, 379-389 formation, 267
Ethene, (see also Ethylene) to esters, 197-201
Ether formation, 228, 263, 367 Etherification, 308, 445 Ethylene, 8, 170
to ethylene glycol, 29 to hydrocarbons, 154 production, 363 relative cost, 29, 362 synthesis, 338-353
Ethylene glycol amination of, 442 new processes for, 29-31 via glycolic acid, 221-247 from synthesis gas, 221
Ethylene oxide, 29 to ethylene glycol, 442 to glycol ethers, 444
Ethylenediamine from ethanolamine, 444 from ethylene oxide, 443
Ethy1isopropy1amine, 454
Fe(K) catalyst, 169 Ferric molybdate, 415 Fischer-Tropsch, 97-128
over AW-500, 336-357 over Co-ZSM-5, 154 over Fe203, 135 homogeneous, 287 reactions, 130
471
selectivity, 136-141, 154, 179, 183, 338
slurry phase, 129-149 support effects, 179-189 over supported ruthenium, 183 over ZSM-5/Fe(K), 170
Fixed-bed reactor, 363, 448 Fluidized-bed reactor, 335 Fluorocarbon matrix, 199 Fluxional behavior, 216 Food supply enhancement, 252 Formaldehyde, 9
intermediate, 333 to diglyco1ic acid, 230 from methanol, 413-418
silver process, 413-415 molybdate process, 415-417
preparation, 222 as preservative, 252 relative cost, 29
Formamide, 251 Formyl intermediates, 115, 222 Formate, 100, 103, 107, 113, 203,
263, 290 Formic acid, 113, 249
as catalyst, 224, 253 synthesis of, 249-260
Fossil fuels to chemicals, 26-29 and economics, 7-9 depletion of, 22 gasification, 41-48
Friedel-Crafts catalysts, 421, 433
Gasification reactions, 41 Gasoline
alcohol blends, 318-320
472
Gasoline (continued) cost, 7, 9 ester blends, 91-93 from methanol, 29 -range hydrocarbons, 162,
169-170 tax apportionment in, 7
GNP, 16 Glycolate ester, 223 Glycolic acid, 221-247
formation, 225, 234
lH NMR, 215, 292 Hammett acidity function, 232 HBF4, 226 HCo(CO)4, 206, 280 H2/CO, see Synthesis gas Hemiacetals, 228 Heteroatoms, 433 Heterolytic dissociation, 101 Heteropoly compounds, 395 Hexamethylenediamine, 444 Higher alcohols, 56 Hofmann orientation, 365, 369 Hollow fiber permeation system,
254 Homogeneous reactions
alcohol homologation, 261 Fischer-Tropsch, 287 water gas shift, 108
Homologation, 261-283 of Cl-C3 alcohols, 274 selectivities, 267-272
Hydrocarbon synthesis over cobalt/CuZnAlO.3, 56 over Co-ZSM-5, 154
from ethylene, 156 from ethanol, 361-394 from Fischer-Tropsch, 135 from methanol, 323-359, 395-411 over small pore zeolites,
325-326 over ZSM-5/Fe(K), 170
Hydrocarbonylation, 271 Hydrochlorination, 420-423
catalysts for, 421 Hydrodesulfurization, 38 Hydroelectric power 4-7 Hydroesterification, 194 Hydroformylation, 203, 275
INDEX
Hydrogen adsorption, 98, 101 in amine alkylation, 450-455 bracketing technique, 180 cyanide, 251 D2 exchange, 101 transfer, 329
Hydrogen fluoride as catalyst, 226
Hydrogenation of aldehydes, 269 asymmetric, 289 catalysts, 435 of olefins, 203 of esters, 221, 236 of oxalate esters, 223 transfer, 292
with alcohols, 295 Hydrogenolysis, 115, 290 Hydrolysis of methyl formate, 255 Hydroxycarbonyl, 100, 103
in Fischer-Tropsch, 116 Hydroxyesters, 227 Hydroxyl groups, 106, 367, 414 Hy-Gas process, 44
Industrial energy conservation by, 19 energy usage by, 27 oil prices, 7
Infrared spectroscopy, 101, 162, 213-216, 417
Insertion of metal into C-H, 303 Intermetallic catalysts, 65 Iodine promoters, 262, 266, 290 Ionic mechanism, 309 Iron chromium catalysts, 41, 108 Iron oxide, 102 Iso-olefins, 307 Isopropanol, 449 Isopropylamine, 449-453
KBW process, 44-45 Keggin unit, 397 Kinetic behavior
supported Ru catalysts, 182 Kinetics
methanol to olefins, 329-332 Kolbel-Englehardt synthesis, 116 Kolbel Fischer-Tropsch data, 146
INDEX
Koppers-Totzek process, 44
Lactic acid, 245, 251 LaNi5, 65 LaRh03, 116 Lurgi process, 44
Magnesia, 105 Mechanism
carboalkylation, 195-196 Fischer-Tropsch, 171 hydrochlorination of methanol,
423 water gas shift
homogeneous, 111, 112 on metals, 102 on oxides, 109
Metal catalysts, 98-100, 183, 435 water gas shift reaction on,
98 Methane
synthesis, 184 via radical process, 409
to chloromethanes, 420-421 to synthesis gas, 37-50
Methanol, 9 catalysts for, 31, 449-453 to chemicals, 31-33 to chloromethanes, 419-432 to gasoline, 29 homologation, 262 to hydrocarbons, 395-411 to olefins, 307, 323-359 relative cost, 29 production, 31 synthesis, 31, 56-57, 65-79,
117, 449-453 yields, 56-62, 70-77
Methoxyacetic acid, 229 Methoxy group, 410, 414 Methoxylation, 312 Methyl formate, 224, 253 Methyl migration, 280 Methylbutylamine, 448 Methylene chloride, 429 Methylene glycol, 227 Methyltertiarybutyl ether
process schematic, 313 production economics, 314-318 properties of, 319
473
Methyltertiarybutyl ether (continued)
synthesis, 307-312 MTBE, see methyltertiarybutyl ether Multi-step reactions, 222
Nafion, 195, 375 Naphtha, 8, 38
gasification of, 42 Natural gas, 11-13, 29
production, 13 proved reserves, 13 reforming, 39
Natural gas policy act, 11 Nickel catalysts
for methane reforming, 40 NMR, 213-218, 297-302 Nomenclature, 467 Nuclear power, 4-7
location, 6 operating capacity, 6 reactors, 5-7
Nucleophilic attack, 100, 110, 278, 280, 438
Nylons, 444
Octane enhancement, 92, 307 Octane number, 170, 175, 319 OECD, 4 Ohio Valley, 4 Oil wells, 10 Olefins
carbomethoxylation of, 193 to esters, 197 hydrogenation, 204 low molecular weight, 323 synthesis,
from ethanol, 361-394 from methanol, 323-359 from synthesis gas, 167-176,
183 OPEC, 4 Organorhodiums, 287 Outer sphere mechanism, 288 Oxalic acid, 223 Oxidation
of butane, 250 of heavy oil, 40 of hydrocarbons, 249 of methanol, 413
474
Oxidation (continued) partial, 41
Oxidative addition, 287-305 Oxide catalysts, 100-107,
366-369, 434 Oxyhydrocarbons, 302
3lp NMR, 213-217, 297 Palladium catalysts, 193, 223,
435, 451 Paraform, 29 Paraformaldehyde, 235 Partial oxidation of oil, 43 Peat
to methanol, 49 to synthesis gas 48
Pentaerythritol, 250 Pentaphenylphosphole, 206 Perfluoroalkanesulfonic acids,
193-202 Peroxide contamination, 209 Petroleum production
in Saudi Arabia, 9 in US, 9 in USSR, 9
Phase transfer reactions, 290 Phosphate catalysts, 370 Photocatalyzed
water gas shift, 112 Photochemical homolysis, 112 Photoelectron spectroscopy
angle-resolved, 104 pKa of phosphines, 207 Polyethers, 287 Polyglycolides, 223 Polyphosphoric acid, 376 Population growth, 19 Potassium
effect on acidity, 175 promotion by, 168
Pressure Swing process, 254 PRISM, 254 Production
of chemicals, 3-36 of energy, 3-36, 8 of petroleum, 10
Propane, 338-353 Propene (see also Propylene)
to esters, 197-201 Propionic acid, 252
Propylene, 8 relative cost, 29 synthesis, 338-353
Proved reserves of crude oil, 11 of natural gas, 13 of petroleum, 10
Purification of formic acid, 257 of synthesis gas, 444
Pyridine alkylation, 438 Pyrolysis gasoline, 313
Rectisol process, 44 Redox potentials, 181 Redox process, 416 Reducibility
of catalyst supports, 185 Reductive elimination, 272 Reformer
feedstocks, 38 reactor, 39
Regioselectivity, 193, 293 Reppe technology, 193 Resin catalysts, 309, 374
INDEX
properties of, 379 Resin-supported catalysts, 194, 311 Reynolds number, 310 Rh(I), 288 Rheinpreussen, 147 Ruthenium catalysts, 81-96,
182-183, 236
SASOL, 46, 146, 181 Saytzeff olefins, 365 Schulz-Flory analysis, 116
distribution, 142-144, 163 Scientific Design/Bethlehem Steel
process, 249 Selective decoupling, 215 Selective poisoning, 366 Selexol process, 44 Semiconductors, 186 Shell gasification process, 42 Silage preservative, 251-252 Silver catalysts, 413 Sintered Fe203, 135 Si02/A1203, 167 Slurry phase reactors, 131-133 SMSI, 183
INDEX
SN2 process, 278 Sodium formate, 250 Solar Energy Research Institute,
48 Soluble acids, 198 Solvent effects, 288 Specialty chemicals, 32-33 Standard of living, 21 Steam reforming
of hydrocarbons, 37-42 of methane, 38
Super-giant fields, 10 Support effects, 179 Surfactants, 290 Synthesis gas
to chemicals, 30 composition of, 40 to esters, 81-96 to ethylene glycol, 221 to Fischer-Tropsch products,
129, 151, 167, 179 to formic acid, 249 to methanol, 53-63 to n-paraffins, 130 production of, 37-50, 254 purification of, 38 relative cost, 29
Synthetic fuels, 15 Synthetic Fuels Corp., 15, 46
TAME, see tertiaryamylmethyl ether
Temperature programmed desorption, 101
Tennessee-Eastman, 15, 45, 446 Tertiary olefins, 307 Tertiaryamylmethyl ether
process schematic, 315 production economics, 315-318 properties of, 319 synthesis, 308, 312-316
Texaco gasification process, 42, 47
Thorium-copper catalysts, 65-79 ThCu5, 70 ThNi5, 70 Trans-alkylation, 453 Trickle bed reactors, 237 Triflic, 195 Trimethyloxonium ion, 333
Tungstophosphoric acid, 397 TVA, 3
Urea, 9
Vacuum residuum, 29 gasification of, 42
Water adsorption
on metals, 99 on oxides, 102
chemisorbed, 103 effect on Fischer-Tropsch,
338-351 physisorbed, 102
Water gas shift catalysts alumina, 108 cobalt-molybdenum, 108 copper-zinc oxide, 108 high temperature, 100 iron-chromium, 41, 108 low temperature, 100 metals, 98 oxides, 100
475
Water gas shift reaction, 38, 41, 85, 97-128, 130
homogeneous, 108 on metals, 98 on oxides, 100 on ZSM-5/Fe(K), 169
Water tolerances gasoline/alcohol blends, 318-320
Wells drilled, 10
Westinghouse process, 44, 46 Winkler process, 44 WPPSS, 6
Zeolite catalysts, 372 Co-ZSM-5, 154 hydrophobicity, 372 ruthenium, 113 small pore, 325-326 ZSM-5, 33, 151, 167, 372, 435
acidity control of, 172 preparation of, 152
ZnO, 38, 101, 181 ZnO/A1203, 59
