Industrial Organic Chemicals, 2nd Edition

by Harold A. Wittcoff (Nexant ChemSystems Inc., USA); Bryan G. Reuben (Emeritus of Chemical Technology, London South Bank University, UK); Jeffery S. Plotkin (Process Evaluation and Research Planning Program, Nexant ChemSystems Inc., USA)

• ISBN13: 9780471443858
• ISBN10: 0471443859
• Edition: 2nd
• Format: Hardcover
• Copyright: 2004-07-01
• Publisher: Wiley-Interscience

Summary

Broadly describes the essential topics of the organic chemicals industry In the past two decades, the organic chemicals industry has undergone unprecedented restructuring, complicated feedstock problems, and massive shifts of capacity to developing countries. In the developed world, specialty chemicals have gained increasing significance. Although the fundamentals of organic chemical and polymer production have remained largely constant, one needs to be aware of the economic, structural, and political changes in the industry in order to understand its current state. This much-expanded Second Edition of Industrial Organic Chemicals presents the various technologies and processes involved in the organic chemicals industry as an organized body of knowledge. It describes the chemistry of the seven basic building block chemicals and their derivatives, how they are manufactured, their economic importance, uses, and associated environmental issues. Also covered are two topics essential to an understanding of modern industrial chemistry-catalysis and polymer synthesis. Key additions to this Second Edition include discussion of: * Sustainability and "green" chemistry * Dendrimers * Metallocenes * Chemicals in biotechnology * Specialty chemicals for pharmaceuticals, electronics, fire retardation, fuel additives, foods, and other uses * Economic, political, and social concepts for understanding future directions of the industry Industrial Organic Chemicals, Second Edition presents the chemistry of both large-scale and specialty products while taking into account important political, environmental, and economic considerations. It provides both a narrative account of the evolution of today's industry from the viewpoint of authors intimately involved with the changes, and an essential reference for chemists, chemical engineers, plastics engineers, petroleum engineers, managers, executives, and policy makers working in and with the organic chemical industry.

Author Biography

HAROLD A. WITTCOFF has taught industrial organic chemistry at the University of Minnesota while serving as Vice President of Corporate Research for General Mills, Inc. As scientific advisor to Nexant ChemSystems, he has presented 300 courses in industrial chemistry in twenty-eight countries. He is author/coauthor of 130 patents and sixty technical publications.

BRYAN G. REUBEN is Professor Emeritus of Chemical Technology at London South Bank University. He has worked on the research and commercial sides of the Chemical Division of Distillers Company, Ltd. (now BP Chemicals), and was a founding member of both Surrey and London South Bank Universities. He is author/coauthor of about 130 publications and a single patent.

JEFFREY S. PLOTKIN is Director of the Process Evaluation and Research Planning program at Nexant ChemSystems. He previously worked at Exxon Chemical and International Specialty Products (ISP) in both research and marketing positions. He is author/coauthor of about twenty-five technical publications and about thirty patents.

Table of Contents

PREFACE	xxiii
PREFACE TO THE FIRST EDITION	xxv
LIST OF ACRONYMS AND ABBREVIATIONS	xxvii
CHAPTER 0 HOW TO USE INDUSTRIAL ORGANIC CHEMICALS, SECOND EDITION	1	(14)
0.1 Why this Book was Written and how it is Structured	1	(2)
0.2 North American Industry Classification	3	(1)
0.3 Units and Nomenclature	4	(1)
0.4 General Bibliography	4	(11)
0.4.1 Encyclopedias	5	(1)
0.4.2 Books	6	(3)
0.4.3 Journals	9	(1)
0.4.4 Patents	9	(2)
0.4.5 Statistics	11	(1)
0.4.6 CD-ROM and On-Line Databases	12	(3)
CHAPTER 1 THE CHEMICAL INDUSTRY	15	(42)
1.1 The National Economy	15	(5)
1.2 Size of the Chemical Industry	20	(1)
1.3 Characteristics of the Chemical Industry	21	(27)
1.3.1 Maturity	21	(7)
1.3.1.1 Realignment of Business Segments	26	(2)
1.3.2 Participation in International Trade	28	(1)
1.3.3 Competition from Developing Countries	29	(3)
1.3.4 Capital Intensity and Economies of Scale	32	(1)
1.3.5 Criticality and Pervasiveness	33	(2)
1.3.6 Freedom of Market Entry	35	(1)
1.3.7 Strong Health and Safety Regulation	36	(5)
1.3.8 High Research and Development Expenditures	41	(5)
1.3.9 Dislocations	46	(2)
1.4 The Top Chemical Companies	48	(2)
1.5 The Top Chemicals	50	(3)
Notes and References	53	(4)
CHAPTER 2 CHEMICALS FROM NATURAL GAS AND PETROLEUM	57	(43)
2.1 Petroleum Distillation	61	(6)
2.2 Petroleum Refining Reactions	67	(25)
2.2.1 Steam Cracking	67	(9)
2.2.1.1 Choice of Feedstock	70	(1)
2.2.1.2 Economics of Steam Cracking	71	(5)
2.2.1.3 Mechanism of Cracking	76	(1)
2.2.2 Catalytic Cracking	76	(3)
2.2.3 Catalytic Reforming	79	(3)
2.2.4 Oligomerization	82	(2)
2.2.5 Alkylation	84	(1)
2.2.6 Hydrotreating and Coking	84	(2)
2.2.7 Dehydrogenation	86	(1)
2.2.8 Isomerization	87	(1)
2.2.9 Metathesis	87	(5)
2.2.9.1 Metathesis Outside the Refinery	89	(1)
2.2.9.2 Mechanism of Metathesis	90	(2)
2.3 The Refinery-A Perspective	92	(4)
2.3.1 The Function of the Refinery and the Potential Petroleum Shortage	92	(1)
2.3.2 Unleaded Gasoline and the Clean Air Act	93	(3)
2.4 Separation of Natural Gas	96	(1)
Notes and References	96	(4)
CHAPTER 3 CHEMICALS AND POLYMERS FROM ETHYLENE	100	(67)
3.1 Ethylene Polymers	105	(4)
3.1.1 Discovery of Low- and High-Density Polyethylenes	105	(1)
3.1.2 Low-Density Polyethylene	106	(1)
3.1.3 High-Density Polyethylene	107	(1)
3.1.4 Linear Low-Density Polyethylene	108	(1)
3.1.5 Very High Molecular Weight Polyethylene	109	(1)
3.2 Ethylene Copolymers	109	(4)
3.2.1 Chlorosulfonated Polyethylene	109	(1)
3.2.2 Ethylene-Vinyl Acetate	110	(1)
3.2.3 Ionomers	111	(1)
3.2.4 Copolymer from "Incompatible" Polymer Blends	111	(1)
3.2.5 Ethylene-Propylene Elastomers	111	(1)
3.2.6 Ultra-Low-Density Polyethylene	112	(1)
3.2.7 Photodegradable Copolymers	112	(1)
3.3 Oligomerization	113	(6)
3.3.1 Dimerization	113	(1)
3.3.2 Ziegler Oligomerization of Ethylene	114	(1)
3.3.3 Other Ethylene Oligomerization Technologies	115	(1)
3.3.4 The Shell Higher Olefins Process (SHOP)	116	(3)
3.4 Vinyl Chloride	119	(2)
3.5 Acetaldehyde	121	(3)
3.6 Vinyl Acetate	124	(2)
3.7 Ethylene Oxide	126	(6)
3.7.1 Ethylene Glycol	127	(2)
3.7.2 Proposed Non-Ethylene Oxide Processes for Ethylene Glycol Production	129	(3)
3.8 Styrene	132	(3)
3.9 Ethanol	135	(2)
3.10 Major Chemicals from Ethylene-A Summary	137	(2)
3.11 Lesser Volume Chemicals from Ethylene	139	(1)
3.11.1 Hydroformylation-Propionaldehyde, Propionic Acid, and n-Propanol	140	(1)
3.11.2 Ethyl Halides	141	(1)
3.11.3 Acetaldehyde Chemistry	142	(4)
3.11.4 Metal Complexes	146	(1)
3.11.5 Ethylenediamine and Related Compounds	147	(2)
3.11.6 Ethylene Oxide and Ethylene Glycol Derivatives	149	(1)
3.11.6.1 Oligomers	149	(1)
3.11.6.2 Glycol Ethers and Esters	149	(1)
3.11.6.3 Ethylene Carbonate	150	(3)
3.11.6.4 Aminoethyl Alcohols (Ethanolamines) and Derivatives	153	(1)
3.11.6.5 Ethylenimine	154	(1)
3.11.6.6 1,3-Propanediol	155	(1)
3.11.6.7 Ethylene Glycol Derivatives	156	(2)
3.11.7 Vinyl Chloride and Ethylene Dichloride Derivatives	158	(1)
3.11.8 Vinyl Fluoride and Vinylidene Fluoride	159	(1)
3.11.9 Ethylene Dibromide	160	(1)
3.11.10 Ethanol Derivatives	161	(1)
3.11.11 Vinyl Esters and Ethers	162	(1)
Notes and References	163	(4)
CHAPTER 4 CHEMICALS AND POLYMERS FROM PROPYLENE	167	(56)
4.1 On-Purpose Propylene Production Technologies and Propane Dehydrogenation	168	(1)
4.2 Propylene via Deep Catalytic Cracking	169	(1)
4.3 Propylene via Olefin Metathesis	169	(2)
4.4 Propylene via Selective C4C5 Cracking	171	(1)
4.5 Main Polymers and Chemicals from Propylene	172	(3)
4.5.1 Propylene Polymers and Copolymers	172	(3)
4.6 Oligomerization	175	(1)
4.7 Acrylic Acid	176	(5)
4.8 Acrylonitrile	181	(3)
4.8.1 Uses of Acrylonitrile	183	(1)
4.9 Cumene, Cumene Hydroperoxide, and Phenol	184	(3)
4.10 Acetone and Isopropanol	187	(1)
4.10.1 Methyl Methacrylate	188	(5)
4.10.2 Methyl Isobutyl Ketone and other Acetone Derivatives	193	(2)
4.11 Propylene Oxide	195	(3)
4.11.1 Propylene Oxide Applications	198	(1)
4.11.2 Projected Propylene Oxide-Propylene Glycol Processes	199	(1)
4.11.3 Other Novel Syntheses of Propylene Oxide	200	(1)
4.11.3.1 Direct Oxidation	200	(1)
4.11.3.2 Use of Peracids or Hydrogen Peroxide	201	(1)
4.11.3.3 Electrochemical Processes	202	(2)
4.11.3.4 Biotechnological Approaches	204	(1)
4.12 n-Butyraldehyde and Isobutyraldehyde	205	(2)
4.12.1 Uses for Butyraldehyde and Isobutyraldehyde	207	(1)
4.12.2 Other Oxo Products	208	(1)
4.13 Major Chemicals from Propylene-A Perspective	209	(2)
4.14 Lesser Volume Chemicals from Propylene	211	(1)
4.14.1 Allyl Chloride and Epichlorohydrin	211	(3)
4.14.2 Glycerol	214	(1)
4.14.3 Acrylamide	215	(1)
4.14.4 Acrolein	216	(2)
4.14.5 Acrylonitrile Derivatives	218	(1)
Notes and References	218	(5)
CHAPTER 5 CHEMICALS AND POLYMERS FROM THE C4 STREAM	223	(32)
5.1 Chemicals and Polymers from Butadiene	226	(16)
5.1.1 Acrylonitrile-Butadiene-Styrene Resins (ABS)	230	(1)
5.1.2 Hexamethylenediamine	231	(5)
5.1.3 Lesser Volume Chemicals from Butadiene	236	(7)
5.1.3.1 Cyclization	236	(1)
5.1.3.2 Dimerization and Trimerization	237	(2)
5.1.3.3 Diels-Alder Reactions	239	(1)
5.1.3.4 Adipic Acid	240	(1)
5.1.3.5 1,4-Butanediol	241	(1)
5.1.3.6 trans-1,4-Hexadiene	241	(1)
5.1.3.7 Dimethyl-2,6-naphthalene Dicarboxylate	241	(1)
5.1.3.8 Butadiene Monoepoxide	241	(1)
5.2 Chemicals and Polymers from Isobutene	242	(6)
5.2.1 Methyl tert-butyl Ether	243	(1)
5.2.2 Butyl Rubber	244	(1)
5.2.3 Polyisobutenes and Isobutene Oligomers and Polymers	244	(1)
5.2.4 tert-Butanol	245	(1)
5.2.5 Methyl Methacrylate	245	(1)
5.2.6 Lesser Volume Chemicals from Isobutene	245	(3)
5.3 Chemicals and Polymers from 1- and 2-Butenes	248	(1)
5.4 Chemicals from η-Butane	249	(2)
5.4.1 Acetic Acid	249	(1)
5.4.2 Maleic Anhydride	249	(2)
Notes and References	251	(4)
CHAPTER 6 CHEMICALS AND POLYMERS FROM THE C5 STREAM	255	(12)
6.1 Separation of the C5 Stream	256	(3)
6.2 Isoprene	259	(4)
6.3 Cyclopentadiene and Dicyclopentadiene	263	(2)
6.4 Pentene-1 and Piperylene	265	(1)
Notes and References	266	(1)
CHAPTER 7 CHEMICALS AND POLYMERS FROM BENZENE	267	(45)
7.1 Phenol	269	(16)
7.1.1 Phenolic Resins	275	(1)
7.1.2 Bisphenol A	276	(5)
7.1.2.1 Epoxy Resins	277	(1)
7.1.2.2 Polvcarbonate Resins	277	(3)
7.1.2.3 Lesser Volume Uses for Bisphenol A	280	(1)
7.1.3 Cyclohexanone	281	(2)
7.1.4 Alkylphenols	283	(1)
7.1.5 Chlorinated Phenols	283	(1)
7.1.6 2,6-Xylenol and Cresols	284	(1)
7.1.7 Aniline from Phenol	284	(1)
7.2 Cyclohexane	285	(9)
7.2.1 Adipic Acid	285	(5)
7.2.1.1 Nylons from Adipic Acid	289	(1)
7.2.2 Caprolactam	290	(4)
7.3 Aniline	294	(2)
7.3.1 4,4'-Diphenylmethane Diisocyanate (MDI)	296	(3)
7.4 Alkylbenzenes	299	(2)
7.5 Maleic Anhydride	301	(1)
7.6 Chlorinated Benzenes	301	(1)
7.7 Dihydroxybenzenes	302	(6)
7.8 Anthraquinone	308	(1)
Notes and References	309	(3)
CHAPTER 8 CHEMICALS AND POLYMERS FROM TOLUENE	312	(8)
8.1 Hydrodealkylation and Disproportionation	313	(1)
8.2 Solvents	314	(1)
8.3 Dinitrotoluene and Toluene Diisocyanate	314	(2)
8.4 Lesser Volume Chemicals from Toluene	316	(2)
Notes and References	318	(2)
CHAPTER 9 CHEMICALS AND POLYMERS FROM XYLENES	320	(18)
9.1 o-Xylene and Phthalic Anhydride	322	(1)
9.1.1 Uses of Phthalic Anhydride	323	(4)
9.2 m-Xylene and Isophthalic Acid	327	(2)
9.2.1 Uses of Isophthalic Acid	328	(1)
9.3 p-Xylene and Terephthalic Acid-Dimethyl Terephthalate	329	(6)
9.3.1 Oxidation of p-Xylene	329	(2)
9.3.2 Alternate Sources for Terephthalic Acid	331	(1)
9.3.3 Poly(ethylene terephthalate)	332	(2)
9.3.4 Lower Volume Polymers from Terephthalic Acid	334	(1)
9.4 Major Chemicals from Xylenes: A Summary	335	(1)
Notes and References	336	(2)
CHAPTER 10 CHEMICALS FROM METHANE	338	(1)
10.1 Hydrocyanic Acid	338	(3)
10.2 Halogenated Methanes	341	(1)
10.2.1 Chloromethane	342	(1)
10.2.2 Dichloromethane	343	(1)
10.2.3 Trichloromethane	343	(1)
10.2.4 Tetrachloromethane and Carbon Disulfide	344	(3)
10.2.5 Bromomethane	347	(1)
10.3 Acetylene	347	(2)
10.3.1 1,4-Butanediol	349	(3)
10.3.2 Lesser Uses for Acetylene	352	(1)
10.4 Synthesis Gas	353	(1)
10.4.1 Steam Reforming of Methane	354	(1)
10.4.2 Variants of Steam Reforming	355	(1)
10.4.3 Partial Oxidation of Hydrocarbons	356	(1)
10.4.4 Solid Feedstocks	357	(1)
10.4.5 Hydrogen	357	(1)
10.5 Chemicals from Synthesis Gas	358	(1)
10.5.1 Ammonia and Its Derivatives	358	(2)
10.5.1.1 Urea and Melamine Resins	360	(2)
10.5.2 Methanol	362	(2)
10.5.2.1 Formaldehyde	364	(1)
10.5.2.2 Acetic Acid	365	(3)
10.5.2.3 Acetic Anhydride	368	(2)
10.5.2.4 Methanol to Gasoline	370	(1)
10.5.2.5 Methanol to Olefins	371	(2)
10.5.2.6 Lower Volume and Proposed Uses for Methanol	373	(2)
10.5.2.7 C1-Based Development Processes	375	(2)
10.6 Carbon Monoxide Chemistry	377	(1)
10.6.1 Proposed Chemistry Based on Carbon Monoxide	378	(4)
10.7 Gas-to-Liquid Fuels	382	(1)
10.7.1 Sasol GTL Technology	382	(1)
10.7.2 Shell Middle Distillate Synthesis	383	(1)
10.7.3 Other GTL Technologies	383	(1)
Notes and References	384	(3)
CHAPTER 11 CHEMICALS FROM ALKANES	387	(1)
11.1 Functionalization of Methane	388	(1)
11.1.1 Methane to Methanol-Formaldehyde	388	(1)
11.1.2 Dimerization of Methane	389	(1)
11.1.3 Aromatization of Methane	390	(1)
11.2 Functionalization of C2-C4 Alkanes	391	(1)
11.2.1 Oxidation of C2-C4 Alkanes	391	(2)
11.2.2 Dehydrogenation of C2-C4 Alkanes	393	(1)
11.2.3 Aromatization of C2-C4 Alkanes	394	(1)
11.3 Carbon Black	394	(1)
Notes and References	395	(4)
CHAPTER 12 CHEMICALS FROM COAL	399	(1)
12.1 Chemicals from Coke Oven Distillate	400	(4)
12.2 The Fischer-Tropsch Reaction	404	(2)
12.3 Coal Hydrogenation	406	(1)
12.4 Substitute Natural Gas (SNG)	407	(1)
12.5 Synthesis Gas Technology	407	(1)
12.6 Calcium Carbide	408	(1)
12.7 Coal and the Environment	409	(1)
Notes and References	409	(2)
CHAPTER 13 FATS AND OILS	411	(5)
13.1 Fatty Acids	416	(3)
13.2 Fatty Nitrogen Compounds	419	(2)
13.3 "Dimer" Acid	421	(2)
13.4 Aminoamides and Imidazolines	423	(1)
13.5 Azelaic, Pelargonic, and Petroselinic Acids	423	(1)
13.6 Fatty Alcohols	424	(2)
13.7 Epoxidized Oils	426	(1)
13.8 Ricinoleic Acid	426	(2)
13.9 Glycerol	428	(1)
13.10 Alcoholysis of Fats and Oils	428	(1)
13.10.1 Cocoa Butter	429	(1)
13.11 The Future of Fat and Oil Chemistry	430	(1)
13.11.1 Non-Caloric Fat-Like Substances	430	(1)
13.11.2 Alkyl Polyglycosides	430	(1)
13.11.3 Fatty Acid-Based Fuels and Lubricants	431	(1)
Notes and References	432	(3)
CHAPTER 14 CARBOHYDRATES	435	(24)
14.1 Sugars and Sorbitol	435	(7)
14.1.1 Furfural	442	(1)
14.2 Starch	443	(3)
14.3 Cellulose	446	(3)
14.4 Gums	449	(1)
14.5 Fermentation and Biotechnology	450	(3)
14.5.1 Amino Acids	453	(1)
14.5.2 Polymers	454	(1)
14.5.3 Proteins by Recombinant DNA Technology	455	(1)
14.5.4 A Fermentation Scenario	455	(1)
14.5.5 Can Ethanol Be Justified as a Fuel?	456	(1)
Notes and References	457	(2)
CHAPTER 15 HOW POLYMERS ARE MADE	459	(5)
15.1 Polymerization	464	(1)
15.2 Functionality	465	(4)
15.3 Step- and Chain-Growth Polymerizations	469	(2)
15.3.1 Free Radical Polymerization	471	(2)
15.3.2 Chain Transfer	473	(2)
15.3.3 Copolymerization	475	(2)
15.3.4 Molecular Weight	477	(1)
15.3.5 Polymerization Procedures	478	(2)
15.3.6 Ionic Polymerization	480	(6)
15.3.7 Living Polymers	486	(1)
15.3.8 Block Copolymers	486	(3)
15.3.9 Graft Copolymers	489	(1)
15.3.10 Metal Complex Catalysts	489	(4)
15.3.11 Metal Oxide Catalysts	493	(1)
15.3.12 Metallocene and Other Single-Site Catalysts	494	(4)
15.3.12.1 Single-Site Nonmetallocene Catalysts	498	(1)
15.3.12.2 Late Transition Metal Catalysts	498	(2)
15.3.12.3 Commercial Prospects	500	(1)
15.4 Examples of Step Polymerization	501	(1)
15.4.1 Phenoplasts and Aminoplasts	501	(2)
15.4.2 Polyurethanes	503	(3)
15.4.3 Epoxy Resins	506	(2)
15.4.4 Dendritic and Hyperbranched Polymers	508	(4)
15.5 Polymer Properties	512	(1)
15.5.1 Crystallinity	512	(4)
15.5.2 Glass Transition Temperature, Crystalline Melting Point, and Softening Temperature	516	(1)
15.5.3 Molecular Cohesion	517	(1)
15.5.4 Stress-Strain Diagrams	518	(2)
15.6 Classes of Polymers	520	(1)
Notes and References	521	(6)
CHAPTER 16 INDUSTRIAL CATALYSIS	527	(1)
16.1 Catalyst Choice	528	(1)
16.1.1 Reaction Velocity and Selectivity	529	(2)
16.1.2 Recovery of Unchanged Catalyst	531	(1)
16.1.3 Catalyst Deactivation	532	(1)
16.1.4 Access to Nonequilibrium Products	532	(1)
16.2 Homogeneous and Heterogeneous Catalysis	533	(1)
16.2.1 Reactors for Heterogeneous Catalysts	534	(1)
16.2.2 "Immobilization" of Homogeneous Catalysts	535	(1)
16.3 Catalyst Markets	536	(3)
16.4 Catalysis by Acids and Bases	539	(4)
16.5 Dual Function Catalysis	543	(1)
16.6 Catalysis by Metals, Semiconductors, and Insulators	544	(1)
16.6.1 Catalysts for Automobile Emission Control	545	(1)
16.7 Coordination Catalysis	546	(1)
16.7.1 Catalysts for Stereoregular Compounds	547	(2)
16.7.2 Asymmetric Synthesis	549	(1)
16.8 Enzymes	550	(2)
16.8.1 Catalytic Antibodies	552	(1)
16.9 Shape-Selective Catalysts	553	(3)
16.10 Phase-Transfer and Fluorous Biphase Catalysis	556	(2)
16.11 Catalysts of the Future	558	(1)
16.11.1 Catalyst Design	558	(1)
16.11.2 Higher Selectivities	559	(1)
16.11.3 Catalysts with Greater Activity	559	(1)
16.11.4 Pollution Problems	560	(1)
16.11.5 Catalysts for New Reactions	560	(1)
16.11.6 Catalysts that Mimic Natural Catalysts	560	(1)
16.11.7 Catalyst Discovery via High Throughput Experimentation	561	(1)
Notes and References	562	(5)
CHAPTER 17 SUSTAINABILITY AND GREEN CHEMISTRY	567	(2)
17.1 Energy Sources	569	(1)
17.1.1 Wind Power	570	(1)
17.1.2 Wave Power	570	(1)
17.1.3 Solar Power	571	(1)
17.1.3.1 Photovoltaic Cells	571	(1)
17.1.3.2 Artificial Photosynthesis	572	(2)
17.1.4 Methane Hydrate	574	(1)
17.1.5 The Hydrogen Economy	575	(1)
17.1.5.1 Fuel Cells	576	(4)
17.2 Pollution	580	(1)
17.2.1 The Ozone Layer	581	(4)
17.2.2 Global Warming	585	(2)
17.2.3 Trace Chemicals	587	(1)
17.2.3.1 Pesticides	587	(1)
17.2.3.2 Nonpesticide Lipophiles	588	(1)
17.2.4 Air Pollution	589	(1)
17.2.4.1 Sulfur Dioxide and Particulates	589	(1)
17.2.4.2 Automobile Exhaust Emissions	590	(3)
17.2.5 Water Treatment	593	(1)
17.2.6 Solid Wastes	594	(1)
17.2.6.1 Waste Prevention	595	(1)
17.2.6.2 Recycling	595	(1)
17.2.6.3 Combustion-Incineration	596	(2)
17.2.6.4 Sanitary Landfill	598	(1)
17.2.7 Petrochemical Industry Wastes	599	(1)
17.2.8 Other Environmental Problems	600	(1)
17.3 Green Chemistry	601	(1)
17.3.1 The Decline in Acetylene Chemistry	602	(1)
17.3.2 Nylon	603	(1)
17.3.3 Replacement of Phosgene	603	(1)
17.3.4 Monomethylation by Dimethyl Carbonate	604	(1)
17.3.5 Liquid and Supercritical Carbon Dioxide and Water	605	(2)
17.3.6 Ionic Liquids	607	(1)
17.3.7 Photocatalysts	608	(1)
17.3.8 Paired Electrosynthesis	608	(1)
17.3.9 Sertraline Synthesis	609	(2)
17.3.10 Catalytic Dehydrogenation of Diethanolamine	611	(1)
17.3.11 Genetic Manipulation	611	(1)
17.3.12 Polyhydroxyalkanoates	612	(1)
17.4 Valediction	613	(1)
Notes and References	614	(6)
APPENDIX 1 A NOTE ON COST CALCULATIONS	620	(4)
APPENDIX 2 UNITS AND CONVERSION FACTORS	624	(2)
APPENDIX 3 SPECIAL UNITS IN THE CHEMICAL INDUSTRY	626	(3)
INDEX	629