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基本説明
This bestselling standard is an excellent source of technological and economic information on the most important precursors and intermediates used in the chemical industry.
Full Description
This bestselling standard, now in its fifth, completely revised English edition, is an excellent source of technological and economic information on the most important precursors and intermediates used in the chemical industry. Both a handbook and ready reference, this volume has a uniform structure for ease of use, with a number of fold-out flow charts illustrating complex chemical processes, plus summaries and relevant statistical data in the margins. The text is rounded off by a comprehensive list of references and a detailed subject index.
From reviews of previous editions (authored by K. Weissermel/H.-J. Arpe)
"This book is an immensely comprehensive and practical work. University chemistry students would benefit from reading this book as it provides a valuable insight into chemical technology, which is often lacking in undergraduate chemistry courses. The university lecturer can obtain examples of applied organic syntheses and keep up to date with the constant changes in chemical manufacturing. It should appeal most to chemists and engineers in the chemical industry, who should benefit from the technological, scientific and economic interrelationships and their potential developments." (Synthesis - Journal of Synthetic Organic Chemistry)
"It would be unkind and misleading to call this book a poor man's Kirk Othmer, but it could almost be described as an encyclopedia... it is easy to read and one has to admire the authors' dedication and endeavor in getting so much into a single volume. They have provided a book that is interesting reading as well as being an excellent reference. It is a highly recommended book, which I hope the authors will find the energy to continue updating on a regular basis." (Chemistry in Britain)
"...it should be ready to hand to every chemist or process engineer involved directly or indirectly with industrial organic chemistry. It should be in the hand of every higher-graduate student, especially if chemical technology is not part of the study, like in many college universities..." (Tenside-Surfactants-Detergents)
"Whether student or scientist, theorist or practician - everybody interested in industrial organic chemistry will appreciate this work. ..." (farbe + lack)
Contents
Preface to the First Edition xiii
Preface to the Second Edition xvii
Preface to the Third Edition xix
Preface to the Fourth Edition xxi
1 Various Aspects of the Energy and Raw Material Supply 1
1.1 Present and Predictable Energy Requirements 2
1.2 Availability of Individual Sources 3
1.2.1 Oil 3
1.2.2 Natural Gas 4
1.2.3 Coal 5
1.2.4 Nuclear Fuels 5
1.3 Prospects for the Future Energy Supply 7
1.4 Present and Anticipated Raw Material Situation 8
1.4.1 Petrochemical Primary Products 8
1.4.2 Coal Conversion Products 11
2 Basic Products of Industrial Syntheses 15
2.1 Synthesis Gas 15
2.1.1 Generation of Synthesis Gas 15
2.1.1.1 Synthesis Gas via Coal Gasification 16
2.1.1.2 Synthesis Gas from Cracking of Natural Gas and Oil 19
2.1.2 Synthesis Gas Purification and Use 21
2.2 Production of the Pure Synthesis Gas Components 24
2.2.1 Carbon Monoxide 24
2.2.2 Hydrogen 26
2.3 C1 Units 29
2.3.1 Methanol 29
2.3.1.1 Manufacture of Methanol 30
2.3.1.2 Applications and Potential Applications of Methanol 32
2.3.2 Formaldehyde 37
2.3.2.1 Formaldehyde from Methanol 38
2.3.2.2 Uses and Potential Uses of Formaldehyde 40
2.3.3 Formic Acid 42
2.3.4 Hydrocyanic Acid 46
2.3.5 Methylamines 51
2.3.6 Halogen Derivatives of Methane 52
3 Olefins 59
3.1 Historical Development of Olefin Chemistry 59
3.2 Olefins from Cracking of Hydrocarbons 60
3.3 Special Manufacturing Processes for Olefins 63
3.3.1 Ethylene, Propene 63
3.3.2 Butenes 67
3.3.3 Higher Olefins 75
3.3.3.1 Unbranched Higher Olefins 75
3.3.3.2 Branched Higher Olefins 83
3.4 Olefin Metathesis 86
4 Acetylene 91
4.1 Present Significance of Acetylene 91
4.2 Manufacturing Processes for Acetylene 93
4.2.1 Manufacture Based on Calcium Carbide 93
4.2.2 Thermal Processes 94
4.3 Utilization of Acetylene 98
5 1,3-Diolefins 107
5.1 1,3-Butadiene 107
5.1.1 Historical Syntheses of 1,3-Butadiene 108
5.1.2 1,3-Butadiene from C4 Cracking Fractions 109
5.1.3 1,3-Butadiene from C4 Alkanes and Alkenes 111
5.1.4 Utilization of 1,3-Butadiene 114
5.2 Isoprene 117
5.2.1 Isoprene from C5 Cracking Fractions 118
5.2.2 Isoprene from Synthetic Reactions 119
5.3 Chloroprene 122
5.4 Cyclopentadiene 125
6 Syntheses involving Carbon Monoxide 127
6.1 Hydroformylation of Olefins 127
6.1.1 Chemical Basis of Hydroformylation 128
6.1.2 Industrial Operation of Hydroformylation 131
6.1.3 Catalyst Modifications in Hydroformylation 134
6.1.4 Utilization of oxo Products 136
6.1.4.1 Oxo Alcohols 136
6.1.4.2 Oxo Carboxylic Acids 138
6.1.4.3 Aldol and Condensation Products of the Oxo Aldehydes 139
6.2 Carbonylation of Olefins 141
6.3 Koch Carboxylic Acid Synthesis 143
7 Oxidation Products of Ethylene 147
7.1 Ethylene Oxide 147
7.1.1 Ethylene Oxide by the Chlorohydrin Process 148
7.1.2 Ethylene Oxide by Direct Oxidation 149
7.1.2.1 Chemical Principles 149
7.1.2.2 Process Operation 150
7.1.2.3 Potential Developments in Ethylene Oxide Manufacture 152
7.2 Secondary Products of Ethylene Oxide 153
7.2.1 Ethylene Glycol and Higher Ethylene Glycols 154
7.2.1.1 Potential Developments in Ethylene Glycol Manufacture 155
7.2.1.2 Uses of Ethylene Glycol 158
7.2.1.3 Secondary Products: Glyoxal, Dioxolane, 1,4-Dioxane 158
7.2.2 Polyethoxylates 160
7.2.3 Ethanolamines and Secondary Products 161
7.2.4 Ethylene Glycol Ethers 164
7.2.5 Additional Products from Ethylene Oxide 167
7.3 Acetaldehyde 168
7.3.1 Acetaldehyde via Oxidation of Ethylene 169
7.3.1.1 Chemical Basis 169
7.3.1.2 Process Operation 171
7.3.2 Acetaldehyde from Ethanol 172
7.3.3 Acetaldehyde by C3/C4 Alkane Oxidation 173
7.4 Secondary Products of Acetaldehyde 173
7.4.1 Acetic Acid 174
7.4.1.1 Acetic Acid by Oxidation of Acetaldehyde 175
7.4.1.2 Acetic Acid by Oxidation of Alkanes and Alkenes 177
7.4.1.3 Carbonylation of Methanol to Acetic Acid 180
7.4.1.4 Potential Developments in Acetic Acid Manufacture 182
7.4.1.5 Use of Acetic Acid 183
7.4.2 Acetic Anhydride and Ketene 185
7.4.3 Aldol Condensation of Acetaldehyde and Secondary Products 189
7.4.4 Ethyl Acetate 191
7.4.5 Pyridine and Alkyl Pyridines 193
8 Alcohols 197
8.1 Lower Alcohols 197
8.1.1 Ethanol 197
8.1.2 2-Propanol 202
8.1.3 Butanols 205
8.1.4 Amyl Alcohols 209
8.2 Higher Alcohols 209
8.2.1 Oxidation of Paraffins to Alcohols 213
8.2.2 Alfol Synthesis 214
8.3 Polyhydric Alcohols 216
8.3.1 Pentaerythritol 216
8.3.2 Trimethylolpropane 217
8.3.3 Neopentyl Glycol 218
9 Vinyl Halogen and Vinyl Oxygen Compounds 221
9.1 Vinyl Halogen Compounds 221
9.1.1 Vinyl Chloride 221
9.1.1.1 Vinyl Chloride from Acetylene 222
9.1.1.2 Vinyl Chloride from Ethylene 223
9.1.1.3 Potential Developments in Vinyl Chloride Manufacture 226
9.1.1.4 Uses of Vinyl Chloride and 1,2-Dichloroethane 227
9.1.2 Vinylidene Chloride 229
9.1.3 Vinyl Fluoride and Vinylidene Fluoride 229
9.1.4 Trichloro- and Tetrachloroethylene 231
9.1.5 Tetrafluoroethylene 233
9.2 Vinyl Esters and Ethers 234
9.2.1 Vinyl Acetate 234
9.2.1.1 Vinyl Acetate Based on Acetylene or Acetaldehyde 234
9.2.1.2 Vinyl Acetate Based on Ethylene 236
9.2.1.3 Possibilities for Development of Vinyl Acetate Manufacture 238
9.2.2 Vinyl Esters of Higher Carboxylic Acids 240
9.2.3 Vinyl Ethers 241
10 Components for Polyamides 243
10.1 Dicarboxylic Acids 245
10.1.1 Adipic Acid 246
10.1.2 1,12-Dodecanedioic Acid 249
10.2 Diamines and Aminocarboxylic Acids 251
10.2.1 Hexamethylenediamine 251
10.2.1.1 Manufacture of Adiponitrile 251
10.2.1.2 Hydrogenation of Adiponitrile 255
10.2.1.3 Potential Developments in Adiponitrile Manufacture 256
10.2.2 ω-Aminoundecanoic Acid 257
10.3 Lactams 258
10.3.1 Є-Caprolactam 258
10.3.1.1 Є-Caprolactam from the Cyclohexanone Oxime Route 258
10.3.1.2 Alternative Manufacturing Processes for Є-Caprolactam 263
10.3.1.3 Possibilities for Development in Є-Caprolactam Manufacture 265
10.3.1.4 Uses of Є-Caprolactam 266
10.3.2 Laurolactam 268
11 Propene Conversion Products 273
11.1 Oxidation Products of Propene 274
11.1.1 Propylene Oxide 274
11.1.1.1 Propylene Oxide from the Chlorohydrin Process 274
11.1.1.2 Indirect Oxidation Routes to Propylene Oxide 275
11.1.1.3 Possibilities for Development in the Manufacture of Propylene Oxide 279
11.1.2 Secondary Products of Propylene Oxide 283
11.1.3 Acetone 285
11.1.3.1 Direct Oxidation of Propene 286
11.1.3.2 Acetone from 2-Propanol 287
11.1.4 Secondary Products of Acetone 288
11.1.4.1 Acetone Aldolization and Secondary Products 289
11.1.4.2 Methacrylic Acid and Ester 290
11.1.5 Acrolein 295
11.1.6 Secondary Products of Acrolein 296
11.1.7 Acrylic Acid and Esters 299
11.1.7.1 Traditional Acrylic Acid Manufacture 299
11.1.7.2 Acrylic Acid from Propene 301
11.1.7.3 Possibilities for Development in Acrylic Acid Manufacture 303
11.2 Allyl Compounds and Secondary Products 304
11.2.1 Allyl Chloride 304
11.2.2 Allyl Alcohol and Esters 307
11.2.3 Glycerol from Allyl Precursors 309
11.3 Acrylonitrile 312
11.3.1 Traditional Acrylonitrile Manufacture 313
11.3.2 Ammoxidation of Propene 314
11.3.2.1 Sohio Acrylonitrile Process 315
11.3.2.2 Other Propene/Propane Ammoxidation Processes 316
11.3.3 Possibilities for Development of Acrylonitrile Manufacture 317
11.3.4 Uses and Secondary Products of Acrylonitrile 318
12 Aromatics — Production and Conversion 321
12.1 Importance of Aromatics 321
12.2 Sources of Feedstocks for Aromatics 322
12.2.1 Aromatics from Coking of Hard Coal 323
12.2.2 Aromatics from Reformate and Pyrolysis Gasoline 324
12.2.2.1 Isolation of Aromatics 327
12.2.2.2 Special Separation Techniques for Non-Aromatic/Aromatic and Aromatic Mixtures 328
12.2.3 Possibilities for Development of Aromatics Manufacture 333
12.2.4 Condensed Aromatics 334
12.2.4.1 Naphthalene 335
12.2.4.2 Anthracene 336
12.3 Conversion Processes for Aromatics 339
12.3.1 Hydrodealkylation 339
12.3.2 m-Xylene Isomerization 341
12.3.3 Disproportionation, Transalkylation, and Methylation 343
13 Benzene Derivatives 347
13.1 Alkylation and Hydrogenation Products of Benzene 348
13.1.1 Ethylbenzene 348
13.1.2 Styrene 351
13.1.3 Cumene 354
13.1.4 Higher Alkylbenzenes 356
13.1.5 Cyclohexane 357
13.2 Oxidation and Secondary Products of Benzene 359
13.2.1 Phenol 359
13.2.1.1 Manufacturing Processes for Phenol 360
13.2.1.2 Potential Developments in Phenol Manufacture 368
13.2.1.3 Uses and Secondary Products of Phenol 370
13.2.2 Dihydroxybenzenes 374
13.2.3 Maleic Anhydride 378
13.2.3.1 Maleic Anhydride from Oxidation of Benzene 379
13.2.3.2 Maleic Anhydride from Oxidation of Butene 380
13.2.3.3 Maleic Anhydride from Oxidation of Butane 382
13.2.3.4 Uses and Secondary Products of Maleic Anhydride 383
13.3 Other Benzene Derivatives 386
13.3.1 Nitrobenzene 386
13.3.2 Aniline 387
13.3.3 Diisocyanates 390
14 Oxidation Products of Xylene and Naphthalene 397
14.1 Phthalic Anhydride 397
14.1.1 Oxidation of Naphthalene to Phthalic Anhydride 397
14.1.2 Oxidation of o-Xylene to Phthalic Anhydride 399
14.1.3 Esters of Phthalic Acid 401
14.2 Terephthalic Acid 404
14.2.1 Manufacture of Dimethyl Terephthalate and Terephthalic Acid 405
14.2.2 Fiber Grade Terephthalic Acid 407
14.2.3 Other Manufacturing Routes to Terephthalic Acid and Derivatives 409
14.2.4 Uses of Terephthalic Acid and Dimethyl Terephthalate 413
15 Appendix 417
15.1 Process and Product Schemes 417
15.2 Definitions of Terms used in Characterizing Chemical Reactions 459
15.3 Abbreviations for Companies 461
15.4 Sources of Information 462
15.4.1 General Literature 462
15.4.2 More Specific Literature (publications, monographs) 464
Index 487
