James G. Speight
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James G. Speight
Handbook of Petrochemical Processes (eBook, PDF)
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This book provides a simplified approach to a very diverse chemical subject dealing with the chemistry and technology of various petroleum and petrochemical process. It presents valuable information containing insights into petrochemical reactions and products, process technology, and polymer synthesis.
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This book provides a simplified approach to a very diverse chemical subject dealing with the chemistry and technology of various petroleum and petrochemical process. It presents valuable information containing insights into petrochemical reactions and products, process technology, and polymer synthesis.
Dieser Download kann aus rechtlichen Gründen nur mit Rechnungsadresse in A, B, BG, CY, CZ, D, DK, EW, E, FIN, F, GR, HR, H, IRL, I, LT, L, LR, M, NL, PL, P, R, S, SLO, SK ausgeliefert werden.
Produktdetails
- Produktdetails
- Verlag: Taylor & Francis
- Seitenzahl: 580
- Erscheinungstermin: 13. Juni 2019
- Englisch
- ISBN-13: 9781498729710
- Artikelnr.: 57000024
- Verlag: Taylor & Francis
- Seitenzahl: 580
- Erscheinungstermin: 13. Juni 2019
- Englisch
- ISBN-13: 9781498729710
- Artikelnr.: 57000024
Dr. James G. Speight has doctorate degrees in Chemistry, Geological Sciences, and Petroleum Engineering and is the author of more than 75 books in petroleum science, petroleum engineering, and environmental sciences.
Dr. Speight has fifty years of experience in areas associated with (i) the properties, recovery, and refining of reservoir fluids, conventional petroleum, heavy oil, and tar sand bitumen, (ii) the properties and refining of natural gas, gaseous fuels, (iii) the production and properties of petrochemicals, (iv) the properties and refining of biomass, biofuels, biogas, and the generation of bioenergy, and (v) the environmental and toxicological effects of fuels. His work has also focused on safety issues, environmental effects, remediation, and safety issues as well as reactors associated with the production and use of fuels and biofuels. He is the author of more than 70 books in petroleum science, petroleum engineering, biomass and biofuels, environmental sciences.
Although he has always worked in private industry which focused on contract-based work, he has served as Adjunct Professor in the Department of Chemical and Fuels Engineering at the University of Utah and in the Departments of Chemistry and Chemical and Petroleum Engineering at the University of Wyoming. In addition, he was a Visiting Professor in the College of Science, University of Mosul, Iraq and has also been a Visiting Professor in Chemical Engineering at the following universities: University of Missouri-Columbia, the Technical University of Denmark, and the University of Trinidad and Tobago.
In 1996, Dr. Speight was elected to the Russian Academy of Sciences and awarded the Gold Medal of Honor that same year for outstanding contributions to the field of petroleum sciences. In 2001, he received the Scientists without Borders Medal of Honor of the Russian Academy of Sciences and was also awarded Dr. Speight the Einstein Medal for outstanding contributions and service in the field of Geological Sciences. In 2005, the Academy awarded Dr. Speight the Gold Medal - Scientists without Frontiers, Russian Academy of Sciences, in recognition of Continuous Encouragement of Scientists to Work Together Across International Borders. In 2007 Dr. Speight received the Methanex Distinguished Professor award at the University of Trinidad and Tobago in recognition of excellence in research.
Dr. Speight has fifty years of experience in areas associated with (i) the properties, recovery, and refining of reservoir fluids, conventional petroleum, heavy oil, and tar sand bitumen, (ii) the properties and refining of natural gas, gaseous fuels, (iii) the production and properties of petrochemicals, (iv) the properties and refining of biomass, biofuels, biogas, and the generation of bioenergy, and (v) the environmental and toxicological effects of fuels. His work has also focused on safety issues, environmental effects, remediation, and safety issues as well as reactors associated with the production and use of fuels and biofuels. He is the author of more than 70 books in petroleum science, petroleum engineering, biomass and biofuels, environmental sciences.
Although he has always worked in private industry which focused on contract-based work, he has served as Adjunct Professor in the Department of Chemical and Fuels Engineering at the University of Utah and in the Departments of Chemistry and Chemical and Petroleum Engineering at the University of Wyoming. In addition, he was a Visiting Professor in the College of Science, University of Mosul, Iraq and has also been a Visiting Professor in Chemical Engineering at the following universities: University of Missouri-Columbia, the Technical University of Denmark, and the University of Trinidad and Tobago.
In 1996, Dr. Speight was elected to the Russian Academy of Sciences and awarded the Gold Medal of Honor that same year for outstanding contributions to the field of petroleum sciences. In 2001, he received the Scientists without Borders Medal of Honor of the Russian Academy of Sciences and was also awarded Dr. Speight the Einstein Medal for outstanding contributions and service in the field of Geological Sciences. In 2005, the Academy awarded Dr. Speight the Gold Medal - Scientists without Frontiers, Russian Academy of Sciences, in recognition of Continuous Encouragement of Scientists to Work Together Across International Borders. In 2007 Dr. Speight received the Methanex Distinguished Professor award at the University of Trinidad and Tobago in recognition of excellence in research.
Contents
Preface..............................................................................................................................................xv
About the
Author............................................................................................................................xvii
Chapter 1 The Petrochemical
Industry..........................................................................................1
1.1
Introduction........................................................................................................1
1.2 Historical Aspects and
Overview.....................................................................
10
1.3 The Petrochemical
Industry.............................................................................
11
1.4
Petrochemicals..................................................................................................
17
1.4.1 Primary
Petrochemicals......................................................................
19
1.4.2 Products and End
Use.........................................................................
19
1.5 Production of
Petrochemicals...........................................................................20
1.6 The
Future........................................................................................................24
References...................................................................................................................29
Chapter 2 Feedstock Composition and
Properties.......................................................................
31
2.1
Introduction......................................................................................................
31
2.2 Natural
Gas.......................................................................................................
31
2.2.1 Composition and
Properties................................................................
33
2.2.2 Natural Gas
Liquids............................................................................
42
2.2.3 Gas
Condensate...................................................................................
43
2.2.4 Gas
Hydrates.......................................................................................44
2.2.5 Other Types of
Gases..........................................................................46
2.2.5.1
Biogas..................................................................................
47
2.2.5.2 Coalbed
Methane.................................................................48
2.2.5.3 Coal
Gas..............................................................................49
2.2.5.4 Geopressurized
Gas............................................................. 51
2.2.5.5 Landfill
Gas.........................................................................
51
2.2.5.6 Refinery
Gas........................................................................
53
2.2.5.7 Synthesis
Gas.......................................................................
57
2.2.5.8 Tight
Gas.............................................................................
58
2.3
Petroleum..........................................................................................................
59
2.3.1 Composition and
Properties................................................................
59
2.3.1.1 Opportunity Crude
Oil........................................................ 61
2.3.1.2 High Acid Crude
Oil........................................................... 61
2.3.1.3 Foamy
Oil............................................................................
62
2.3.1.4 Tight
Oil...............................................................................
62
2.3.2 Other Petroleum-Derived
Feedstocks.................................................63
2.3.2.1
Naphtha................................................................................63
2.3.2.2
Kerosene..............................................................................64
2.3.2.3 Fuel
Oil................................................................................65
2.3.2.4 Gas
Oil.................................................................................
67
2.3.2.5
Residua.................................................................................
67
2.3.2.6 Used Lubricating
Oil...........................................................68
2.4 Heavy Oil, Extra Heavy Oil, and Tar Sand
Bitumen.......................................68
2.4.1 Heavy
Oil............................................................................................69
2.4.2 Extra Heavy
Oil...................................................................................69
2.4.3 Tar sand
Bitumen................................................................................
71
References...................................................................................................................
74
Chapter 3 Other Feedstocks-Coal, Oil Shale, and
Biomass..................................................... 79
3.1
Introduction......................................................................................................
79
3.2
Coal..................................................................................................................
81
3.2.1 Coal
Feedstocks..................................................................................82
3.2.2 Properties and
Composition................................................................83
3.2.3
Conversion...........................................................................................83
3.2.4 Coal Tar
Chemicals.............................................................................85
3.3 Oil
Shale...........................................................................................................90
3.3.1 Shale Oil
Production...........................................................................90
3.3.2 Shale Oil
Properties............................................................................
91
3.3.2.1 Hydrocarbon
Products.........................................................92
3.3.2.2 Nitrogen-Containing
Compounds.......................................93
3.3.2.3 Oxygen-Containing
Compounds.........................................94
3.3.2.4 Sulfur-Containing
Compounds...........................................94
3.4
Biomass............................................................................................................94
3.4.1 Biomass
Feedstocks............................................................................97
3.4.1.1
Carbohydrates......................................................................99
3.4.1.2 Vegetable
Oils......................................................................99
3.4.1.3 Plant
Fibers..........................................................................99
3.4.2
Biorefining.........................................................................................
100
3.4.2.1
Pyrolysis............................................................................
103
3.4.2.2
Gasification........................................................................
103
3.4.2.3 Anaerobic
Digestion.......................................................... 107
3.4.2.4
Fermentation......................................................................
110
3.4.3 Chemicals from
Biomass..................................................................
111
3.4.3.1 Gaseous
Products............................................................... 111
3.4.3.2 Liquid
Products..................................................................
112
3.4.3.3 Solid
Products....................................................................
114
3.5
Waste..............................................................................................................
114
References.................................................................................................................
115
Chapter 4 Feedstock
Preparation...............................................................................................
119
4.1
Introduction....................................................................................................
119
4.2 Gas
Streams....................................................................................................
120
4.2.1
Sources..............................................................................................
121
4.2.1.1 Gas Streams from Natural
Gas.......................................... 121
4.2.1.2 Natural Gas Liquids and Liquefied Petroleum Gas........... 123
4.2.1.3 Gas Streams from Crude
Oil.............................................124
4.2.2 Gas
Processing..................................................................................
127
4.2.2.1 Acid Gas
Removal............................................................. 128
4.2.2.2 Recovery of Condensable Hydrocarbon Derivatives......... 137
4.2.2.3 Water
Removal..................................................................
142
4.2.2.4 Nitrogen
Removal.............................................................. 145
4.2.2.5 The Claus
Process.............................................................. 145
4.3 Petroleum
Streams..........................................................................................
147
4.3.1 Refinery
Configuration......................................................................
149
4.3.2 Cracking
Processes...........................................................................
150
4.3.2.1 Thermal Cracking
Processes............................................. 150
4.3.2.2 Catalytic Cracking
Processes............................................ 153
4.3.3 Dehydrogenation
Processes...............................................................
155
4.3.4 Dehydrocyclization
Processes........................................................... 157
4.4 Streams from Coal, Oil Shale, and
Biomass.................................................. 158
4.4.1
Coal...................................................................................................
158
4.4.1.1 Coal
Gas............................................................................
158
4.4.1.2 Coal
Liquids......................................................................
158
4.4.2 Oil
Shale............................................................................................
159
4.4.2.1 Oil Shale
Gas.....................................................................
159
4.4.2.2 Shale
Oil............................................................................
160
4.4.3
Biomass.............................................................................................
161
4.4.3.1
Biogas................................................................................
161
4.4.3.2
Bio-liquids.........................................................................
161
References.................................................................................................................
162
Chapter 5 Feedstock Preparation by
Gasification......................................................................
165
5.1
Introduction....................................................................................................
165
5.2 Gasification
Chemistry...................................................................................
168
5.2.1 General
Aspects................................................................................
169
5.2.2
Pretreatment......................................................................................
170
5.2.3
Reactions...........................................................................................
171
5.2.3.1 Primary
Gasification.......................................................... 174
5.2.3.2 Secondary
Gasification...................................................... 174
5.2.3.3 Water-Gas Shift
Reaction.................................................. 176
5.2.3.4 Carbon Dioxide
Gasification............................................. 177
5.2.3.5
Hydrogasification...............................................................
178
5.2.3.6
Methanation.......................................................................
178
5.3 Gasification
Processes....................................................................................
179
5.3.1
Gasifiers.............................................................................................
180
5.3.2 FT
Synthesis......................................................................................
181
5.3.3
Feedstocks.........................................................................................
183
5.3.3.1 Heavy
Feedstocks..............................................................
183
5.3.3.2 Solvent Deasphalter
Bottoms............................................. 184
5.3.3.3 Asphalt, Tar, and
Pitch...................................................... 184
5.3.3.4 Petroleum
Coke.................................................................. 186
5.3.3.5
Coal....................................................................................
188
5.3.3.6
Biomass..............................................................................
189
5.3.3.7 Solid
Waste........................................................................
191
5.3.3.8 Black
Liquor......................................................................
193
5.4 Gasification in a
Refinery...............................................................................
193
5.4.1 Gasification of Heavy
Feedstocks..................................................... 195
5.4.2 Gasification of Heavy Feedstocks with
Coal.................................... 195
5.4.3 Gasification of Heavy Feedstocks with
Biomass.............................. 196
5.4.4 Gasification of Heavy Feedstocks with
Waste.................................. 198
5.5 Gas Production and Other
Products............................................................... 198
5.5.1 Gaseous
Products..............................................................................
199
5.5.1.1 Synthesis
Gas.....................................................................
199
5.5.1.2 Low Btu
Gas......................................................................200
5.5.1.3 Medium Btu
Gas................................................................200
5.5.1.4 High Btu
Gas.....................................................................
201
5.5.2 Liquid
Products.................................................................................
201
5.5.3 Solid
Products...................................................................................202
5.6 The
Future......................................................................................................202
References.................................................................................................................204
Chapter 6 Chemicals from Paraffin
Hydrocarbons...................................................................209
6.1
Introduction....................................................................................................209
6.2
Methane..........................................................................................................
211
6.2.1 Physical
Properties............................................................................
212
6.2.2 Chemical
Properties..........................................................................
213
6.2.3 Chemicals from
Methane..................................................................
215
6.2.3.1 Carbon
Disulfide................................................................
216
6.2.3.2
Ethylene.............................................................................
217
6.2.3.3 Hydrogen
Cyanide............................................................. 218
6.2.3.4 Chloromethane
Derivatives............................................... 218
6.2.3.5 Synthesis
Gas.....................................................................220
6.2.3.6
Urea....................................................................................223
6.2.3.7 Methyl
Alcohol..................................................................223
6.2.3.8
Formaldehyde....................................................................226
6.2.3.9 Aldehyde
Derivatives.........................................................229
6.2.3.10 Ethylene
Glycol..................................................................229
6.2.3.11
Nitration.............................................................................230
6.2.3.12
Oxidation...........................................................................230
6.2.3.13 Carboxylic
Acids............................................................... 231
6.2.3.14
Alkylation..........................................................................
231
6.2.3.15
Thermolysis.......................................................................
232
6.2.4 Oxidative
Coupling...........................................................................
233
6.3
Ethane.............................................................................................................
235
6.3.1 Physical
Properties............................................................................
235
6.3.2 Chemical
Properties..........................................................................236
6.3.3 Chemicals from
Ethane.....................................................................
237
6.4
Propane...........................................................................................................238
6.4.1 Physical
Properties............................................................................238
6.4.2 Chemical
Properties..........................................................................
239
6.4.3 Chemicals from
Propane...................................................................240
6.4.3.1
Oxidation...........................................................................240
6.4.3.2
Chlorination.......................................................................240
6.4.3.3
Dehydrogenation................................................................
241
6.4.3.4
Nitration.............................................................................
247
6.5 Butane
Isomers...............................................................................................
247
6.5.1 Physical
Properties............................................................................249
6.5.2 Chemical
Properties..........................................................................249
6.5.3 Chemicals from
Butane.....................................................................250
6.5.3.1
Oxidation...........................................................................250
6.5.3.2 Production of
Aromatics.................................................... 252
6.5.3.3
Isomerization.....................................................................
252
6.5.4 Chemicals from
Isobutane................................................................
252
6.6 Liquid Petroleum Fractions and
Residues...................................................... 252
6.6.1
Naphtha.............................................................................................254
6.6.1.1 Physical
Properties............................................................254
6.6.1.2 Chemical
Properties.......................................................... 255
6.6.1.3 Chemicals from
Naphtha...................................................256
6.6.2
Kerosene............................................................................................
257
6.6.2.1 Physical
Properties............................................................ 257
6.6.2.2 Chemical
Properties.......................................................... 257
6.6.2.3 Chemicals from
Kerosene................................................. 258
6.6.3 Gas
Oil..............................................................................................
258
6.6.3.1 Physical
Properties............................................................ 258
6.6.3.2 Chemical
Properties.......................................................... 259
6.6.3.3 Chemicals from Gas
Oil.................................................... 259
6.6.4 Fuel
Oil..............................................................................................260
6.6.4.1 Physical
Properties............................................................ 261
6.6.4.2 Chemical
Properties.......................................................... 261
6.6.4.3 Chemicals from Fuel
Oil................................................... 262
6.6.5
Resids................................................................................................
262
6.6.5.1 Physical
Properties............................................................263
6.6.6 Used Lubricating
Oil.........................................................................263
6.6.7 Naphthenic
Acids..............................................................................263
6.6.8 Chemicals from Liquid Petroleum Fractions and
Residues..............264
6.6.8.1
Oxidation...........................................................................265
6.6.8.2
Chlorination.......................................................................265
6.6.8.3
Sulfonation.........................................................................265
6.6.8.4 Other
Products...................................................................266
References.................................................................................................................266
Chapter 7 Chemicals from Olefin
Hydrocarbons......................................................................269
7.1
Introduction....................................................................................................269
7.2 Chemicals from
Ethylene...............................................................................
271
7.2.1
Alcohols............................................................................................
273
7.2.2
Alkylation..........................................................................................
275
7.2.3 Halogen
Derivatives..........................................................................
276
7.2.4 Oxygen
Derivatives...........................................................................277
7.2.4.1 Ethylene
Glycol..................................................................
279
7.2.4.2
Ethoxylates.........................................................................
281
7.2.4.3
Ethanolamines...................................................................282
7.2.4.4
1,3-Propanediol..................................................................282
7.2.4.5
Acetaldehyde.....................................................................283
7.2.5
Carbonylation....................................................................................285
7.2.6
Chlorination......................................................................................286
7.2.6.1 Vinyl
Chloride...................................................................286
7.2.6.2 Perchloroethylene and
Trichloroethylene..........................287
7.2.7
Hydration...........................................................................................287
7.2.8
Oligomerization.................................................................................288
7.2.9
Polymerization..................................................................................289
7.2.10 1
-Butylene..........................................................................................290
7.2.11
Polymerization..................................................................................290
7.3 Chemicals from
Propylene.............................................................................
291
7.3.1
Oxidation...........................................................................................294
7.3.2
Ammoxidation...................................................................................296
7.3.3
Oxyacylation......................................................................................299
7.3.4
Chlorination......................................................................................300
7.3.5
Hydration...........................................................................................300
7.3.6 Addition of Organic
Acids................................................................302
7.3.7
Hydroformylation..............................................................................302
7.3.8
Disproportionation............................................................................303
7.3.9
Alkylation..........................................................................................303
7.4 Chemicals from C4
Olefins.............................................................................303
7.4.1
Butylene.............................................................................................304
7.4.1.1
Oxidation...........................................................................306
7.4.1.2
Hydration...........................................................................308
7.4.1.3
Isomerization.....................................................................309
7.4.1.4
Metathesis..........................................................................309
7.4.1.5
Oligomerization.................................................................
310
7.4.2
Isobutylene........................................................................................
310
7.4.2.1
Oxidation...........................................................................
311
7.4.2.2
Epoxidation........................................................................
311
7.4.2.3 Addition of
Alcohols......................................................... 312
7.4.2.4
Hydration...........................................................................
312
7.4.2.5
Carbonylation....................................................................
312
7.4.2.6 Dimerization...........
Preface..............................................................................................................................................xv
About the
Author............................................................................................................................xvii
Chapter 1 The Petrochemical
Industry..........................................................................................1
1.1
Introduction........................................................................................................1
1.2 Historical Aspects and
Overview.....................................................................
10
1.3 The Petrochemical
Industry.............................................................................
11
1.4
Petrochemicals..................................................................................................
17
1.4.1 Primary
Petrochemicals......................................................................
19
1.4.2 Products and End
Use.........................................................................
19
1.5 Production of
Petrochemicals...........................................................................20
1.6 The
Future........................................................................................................24
References...................................................................................................................29
Chapter 2 Feedstock Composition and
Properties.......................................................................
31
2.1
Introduction......................................................................................................
31
2.2 Natural
Gas.......................................................................................................
31
2.2.1 Composition and
Properties................................................................
33
2.2.2 Natural Gas
Liquids............................................................................
42
2.2.3 Gas
Condensate...................................................................................
43
2.2.4 Gas
Hydrates.......................................................................................44
2.2.5 Other Types of
Gases..........................................................................46
2.2.5.1
Biogas..................................................................................
47
2.2.5.2 Coalbed
Methane.................................................................48
2.2.5.3 Coal
Gas..............................................................................49
2.2.5.4 Geopressurized
Gas............................................................. 51
2.2.5.5 Landfill
Gas.........................................................................
51
2.2.5.6 Refinery
Gas........................................................................
53
2.2.5.7 Synthesis
Gas.......................................................................
57
2.2.5.8 Tight
Gas.............................................................................
58
2.3
Petroleum..........................................................................................................
59
2.3.1 Composition and
Properties................................................................
59
2.3.1.1 Opportunity Crude
Oil........................................................ 61
2.3.1.2 High Acid Crude
Oil........................................................... 61
2.3.1.3 Foamy
Oil............................................................................
62
2.3.1.4 Tight
Oil...............................................................................
62
2.3.2 Other Petroleum-Derived
Feedstocks.................................................63
2.3.2.1
Naphtha................................................................................63
2.3.2.2
Kerosene..............................................................................64
2.3.2.3 Fuel
Oil................................................................................65
2.3.2.4 Gas
Oil.................................................................................
67
2.3.2.5
Residua.................................................................................
67
2.3.2.6 Used Lubricating
Oil...........................................................68
2.4 Heavy Oil, Extra Heavy Oil, and Tar Sand
Bitumen.......................................68
2.4.1 Heavy
Oil............................................................................................69
2.4.2 Extra Heavy
Oil...................................................................................69
2.4.3 Tar sand
Bitumen................................................................................
71
References...................................................................................................................
74
Chapter 3 Other Feedstocks-Coal, Oil Shale, and
Biomass..................................................... 79
3.1
Introduction......................................................................................................
79
3.2
Coal..................................................................................................................
81
3.2.1 Coal
Feedstocks..................................................................................82
3.2.2 Properties and
Composition................................................................83
3.2.3
Conversion...........................................................................................83
3.2.4 Coal Tar
Chemicals.............................................................................85
3.3 Oil
Shale...........................................................................................................90
3.3.1 Shale Oil
Production...........................................................................90
3.3.2 Shale Oil
Properties............................................................................
91
3.3.2.1 Hydrocarbon
Products.........................................................92
3.3.2.2 Nitrogen-Containing
Compounds.......................................93
3.3.2.3 Oxygen-Containing
Compounds.........................................94
3.3.2.4 Sulfur-Containing
Compounds...........................................94
3.4
Biomass............................................................................................................94
3.4.1 Biomass
Feedstocks............................................................................97
3.4.1.1
Carbohydrates......................................................................99
3.4.1.2 Vegetable
Oils......................................................................99
3.4.1.3 Plant
Fibers..........................................................................99
3.4.2
Biorefining.........................................................................................
100
3.4.2.1
Pyrolysis............................................................................
103
3.4.2.2
Gasification........................................................................
103
3.4.2.3 Anaerobic
Digestion.......................................................... 107
3.4.2.4
Fermentation......................................................................
110
3.4.3 Chemicals from
Biomass..................................................................
111
3.4.3.1 Gaseous
Products............................................................... 111
3.4.3.2 Liquid
Products..................................................................
112
3.4.3.3 Solid
Products....................................................................
114
3.5
Waste..............................................................................................................
114
References.................................................................................................................
115
Chapter 4 Feedstock
Preparation...............................................................................................
119
4.1
Introduction....................................................................................................
119
4.2 Gas
Streams....................................................................................................
120
4.2.1
Sources..............................................................................................
121
4.2.1.1 Gas Streams from Natural
Gas.......................................... 121
4.2.1.2 Natural Gas Liquids and Liquefied Petroleum Gas........... 123
4.2.1.3 Gas Streams from Crude
Oil.............................................124
4.2.2 Gas
Processing..................................................................................
127
4.2.2.1 Acid Gas
Removal............................................................. 128
4.2.2.2 Recovery of Condensable Hydrocarbon Derivatives......... 137
4.2.2.3 Water
Removal..................................................................
142
4.2.2.4 Nitrogen
Removal.............................................................. 145
4.2.2.5 The Claus
Process.............................................................. 145
4.3 Petroleum
Streams..........................................................................................
147
4.3.1 Refinery
Configuration......................................................................
149
4.3.2 Cracking
Processes...........................................................................
150
4.3.2.1 Thermal Cracking
Processes............................................. 150
4.3.2.2 Catalytic Cracking
Processes............................................ 153
4.3.3 Dehydrogenation
Processes...............................................................
155
4.3.4 Dehydrocyclization
Processes........................................................... 157
4.4 Streams from Coal, Oil Shale, and
Biomass.................................................. 158
4.4.1
Coal...................................................................................................
158
4.4.1.1 Coal
Gas............................................................................
158
4.4.1.2 Coal
Liquids......................................................................
158
4.4.2 Oil
Shale............................................................................................
159
4.4.2.1 Oil Shale
Gas.....................................................................
159
4.4.2.2 Shale
Oil............................................................................
160
4.4.3
Biomass.............................................................................................
161
4.4.3.1
Biogas................................................................................
161
4.4.3.2
Bio-liquids.........................................................................
161
References.................................................................................................................
162
Chapter 5 Feedstock Preparation by
Gasification......................................................................
165
5.1
Introduction....................................................................................................
165
5.2 Gasification
Chemistry...................................................................................
168
5.2.1 General
Aspects................................................................................
169
5.2.2
Pretreatment......................................................................................
170
5.2.3
Reactions...........................................................................................
171
5.2.3.1 Primary
Gasification.......................................................... 174
5.2.3.2 Secondary
Gasification...................................................... 174
5.2.3.3 Water-Gas Shift
Reaction.................................................. 176
5.2.3.4 Carbon Dioxide
Gasification............................................. 177
5.2.3.5
Hydrogasification...............................................................
178
5.2.3.6
Methanation.......................................................................
178
5.3 Gasification
Processes....................................................................................
179
5.3.1
Gasifiers.............................................................................................
180
5.3.2 FT
Synthesis......................................................................................
181
5.3.3
Feedstocks.........................................................................................
183
5.3.3.1 Heavy
Feedstocks..............................................................
183
5.3.3.2 Solvent Deasphalter
Bottoms............................................. 184
5.3.3.3 Asphalt, Tar, and
Pitch...................................................... 184
5.3.3.4 Petroleum
Coke.................................................................. 186
5.3.3.5
Coal....................................................................................
188
5.3.3.6
Biomass..............................................................................
189
5.3.3.7 Solid
Waste........................................................................
191
5.3.3.8 Black
Liquor......................................................................
193
5.4 Gasification in a
Refinery...............................................................................
193
5.4.1 Gasification of Heavy
Feedstocks..................................................... 195
5.4.2 Gasification of Heavy Feedstocks with
Coal.................................... 195
5.4.3 Gasification of Heavy Feedstocks with
Biomass.............................. 196
5.4.4 Gasification of Heavy Feedstocks with
Waste.................................. 198
5.5 Gas Production and Other
Products............................................................... 198
5.5.1 Gaseous
Products..............................................................................
199
5.5.1.1 Synthesis
Gas.....................................................................
199
5.5.1.2 Low Btu
Gas......................................................................200
5.5.1.3 Medium Btu
Gas................................................................200
5.5.1.4 High Btu
Gas.....................................................................
201
5.5.2 Liquid
Products.................................................................................
201
5.5.3 Solid
Products...................................................................................202
5.6 The
Future......................................................................................................202
References.................................................................................................................204
Chapter 6 Chemicals from Paraffin
Hydrocarbons...................................................................209
6.1
Introduction....................................................................................................209
6.2
Methane..........................................................................................................
211
6.2.1 Physical
Properties............................................................................
212
6.2.2 Chemical
Properties..........................................................................
213
6.2.3 Chemicals from
Methane..................................................................
215
6.2.3.1 Carbon
Disulfide................................................................
216
6.2.3.2
Ethylene.............................................................................
217
6.2.3.3 Hydrogen
Cyanide............................................................. 218
6.2.3.4 Chloromethane
Derivatives............................................... 218
6.2.3.5 Synthesis
Gas.....................................................................220
6.2.3.6
Urea....................................................................................223
6.2.3.7 Methyl
Alcohol..................................................................223
6.2.3.8
Formaldehyde....................................................................226
6.2.3.9 Aldehyde
Derivatives.........................................................229
6.2.3.10 Ethylene
Glycol..................................................................229
6.2.3.11
Nitration.............................................................................230
6.2.3.12
Oxidation...........................................................................230
6.2.3.13 Carboxylic
Acids............................................................... 231
6.2.3.14
Alkylation..........................................................................
231
6.2.3.15
Thermolysis.......................................................................
232
6.2.4 Oxidative
Coupling...........................................................................
233
6.3
Ethane.............................................................................................................
235
6.3.1 Physical
Properties............................................................................
235
6.3.2 Chemical
Properties..........................................................................236
6.3.3 Chemicals from
Ethane.....................................................................
237
6.4
Propane...........................................................................................................238
6.4.1 Physical
Properties............................................................................238
6.4.2 Chemical
Properties..........................................................................
239
6.4.3 Chemicals from
Propane...................................................................240
6.4.3.1
Oxidation...........................................................................240
6.4.3.2
Chlorination.......................................................................240
6.4.3.3
Dehydrogenation................................................................
241
6.4.3.4
Nitration.............................................................................
247
6.5 Butane
Isomers...............................................................................................
247
6.5.1 Physical
Properties............................................................................249
6.5.2 Chemical
Properties..........................................................................249
6.5.3 Chemicals from
Butane.....................................................................250
6.5.3.1
Oxidation...........................................................................250
6.5.3.2 Production of
Aromatics.................................................... 252
6.5.3.3
Isomerization.....................................................................
252
6.5.4 Chemicals from
Isobutane................................................................
252
6.6 Liquid Petroleum Fractions and
Residues...................................................... 252
6.6.1
Naphtha.............................................................................................254
6.6.1.1 Physical
Properties............................................................254
6.6.1.2 Chemical
Properties.......................................................... 255
6.6.1.3 Chemicals from
Naphtha...................................................256
6.6.2
Kerosene............................................................................................
257
6.6.2.1 Physical
Properties............................................................ 257
6.6.2.2 Chemical
Properties.......................................................... 257
6.6.2.3 Chemicals from
Kerosene................................................. 258
6.6.3 Gas
Oil..............................................................................................
258
6.6.3.1 Physical
Properties............................................................ 258
6.6.3.2 Chemical
Properties.......................................................... 259
6.6.3.3 Chemicals from Gas
Oil.................................................... 259
6.6.4 Fuel
Oil..............................................................................................260
6.6.4.1 Physical
Properties............................................................ 261
6.6.4.2 Chemical
Properties.......................................................... 261
6.6.4.3 Chemicals from Fuel
Oil................................................... 262
6.6.5
Resids................................................................................................
262
6.6.5.1 Physical
Properties............................................................263
6.6.6 Used Lubricating
Oil.........................................................................263
6.6.7 Naphthenic
Acids..............................................................................263
6.6.8 Chemicals from Liquid Petroleum Fractions and
Residues..............264
6.6.8.1
Oxidation...........................................................................265
6.6.8.2
Chlorination.......................................................................265
6.6.8.3
Sulfonation.........................................................................265
6.6.8.4 Other
Products...................................................................266
References.................................................................................................................266
Chapter 7 Chemicals from Olefin
Hydrocarbons......................................................................269
7.1
Introduction....................................................................................................269
7.2 Chemicals from
Ethylene...............................................................................
271
7.2.1
Alcohols............................................................................................
273
7.2.2
Alkylation..........................................................................................
275
7.2.3 Halogen
Derivatives..........................................................................
276
7.2.4 Oxygen
Derivatives...........................................................................277
7.2.4.1 Ethylene
Glycol..................................................................
279
7.2.4.2
Ethoxylates.........................................................................
281
7.2.4.3
Ethanolamines...................................................................282
7.2.4.4
1,3-Propanediol..................................................................282
7.2.4.5
Acetaldehyde.....................................................................283
7.2.5
Carbonylation....................................................................................285
7.2.6
Chlorination......................................................................................286
7.2.6.1 Vinyl
Chloride...................................................................286
7.2.6.2 Perchloroethylene and
Trichloroethylene..........................287
7.2.7
Hydration...........................................................................................287
7.2.8
Oligomerization.................................................................................288
7.2.9
Polymerization..................................................................................289
7.2.10 1
-Butylene..........................................................................................290
7.2.11
Polymerization..................................................................................290
7.3 Chemicals from
Propylene.............................................................................
291
7.3.1
Oxidation...........................................................................................294
7.3.2
Ammoxidation...................................................................................296
7.3.3
Oxyacylation......................................................................................299
7.3.4
Chlorination......................................................................................300
7.3.5
Hydration...........................................................................................300
7.3.6 Addition of Organic
Acids................................................................302
7.3.7
Hydroformylation..............................................................................302
7.3.8
Disproportionation............................................................................303
7.3.9
Alkylation..........................................................................................303
7.4 Chemicals from C4
Olefins.............................................................................303
7.4.1
Butylene.............................................................................................304
7.4.1.1
Oxidation...........................................................................306
7.4.1.2
Hydration...........................................................................308
7.4.1.3
Isomerization.....................................................................309
7.4.1.4
Metathesis..........................................................................309
7.4.1.5
Oligomerization.................................................................
310
7.4.2
Isobutylene........................................................................................
310
7.4.2.1
Oxidation...........................................................................
311
7.4.2.2
Epoxidation........................................................................
311
7.4.2.3 Addition of
Alcohols......................................................... 312
7.4.2.4
Hydration...........................................................................
312
7.4.2.5
Carbonylation....................................................................
312
7.4.2.6 Dimerization...........
Contents
Preface..............................................................................................................................................xv
About the
Author............................................................................................................................xvii
Chapter 1 The Petrochemical
Industry..........................................................................................1
1.1
Introduction........................................................................................................1
1.2 Historical Aspects and
Overview.....................................................................
10
1.3 The Petrochemical
Industry.............................................................................
11
1.4
Petrochemicals..................................................................................................
17
1.4.1 Primary
Petrochemicals......................................................................
19
1.4.2 Products and End
Use.........................................................................
19
1.5 Production of
Petrochemicals...........................................................................20
1.6 The
Future........................................................................................................24
References...................................................................................................................29
Chapter 2 Feedstock Composition and
Properties.......................................................................
31
2.1
Introduction......................................................................................................
31
2.2 Natural
Gas.......................................................................................................
31
2.2.1 Composition and
Properties................................................................
33
2.2.2 Natural Gas
Liquids............................................................................
42
2.2.3 Gas
Condensate...................................................................................
43
2.2.4 Gas
Hydrates.......................................................................................44
2.2.5 Other Types of
Gases..........................................................................46
2.2.5.1
Biogas..................................................................................
47
2.2.5.2 Coalbed
Methane.................................................................48
2.2.5.3 Coal
Gas..............................................................................49
2.2.5.4 Geopressurized
Gas............................................................. 51
2.2.5.5 Landfill
Gas.........................................................................
51
2.2.5.6 Refinery
Gas........................................................................
53
2.2.5.7 Synthesis
Gas.......................................................................
57
2.2.5.8 Tight
Gas.............................................................................
58
2.3
Petroleum..........................................................................................................
59
2.3.1 Composition and
Properties................................................................
59
2.3.1.1 Opportunity Crude
Oil........................................................ 61
2.3.1.2 High Acid Crude
Oil........................................................... 61
2.3.1.3 Foamy
Oil............................................................................
62
2.3.1.4 Tight
Oil...............................................................................
62
2.3.2 Other Petroleum-Derived
Feedstocks.................................................63
2.3.2.1
Naphtha................................................................................63
2.3.2.2
Kerosene..............................................................................64
2.3.2.3 Fuel
Oil................................................................................65
2.3.2.4 Gas
Oil.................................................................................
67
2.3.2.5
Residua.................................................................................
67
2.3.2.6 Used Lubricating
Oil...........................................................68
2.4 Heavy Oil, Extra Heavy Oil, and Tar Sand
Bitumen.......................................68
2.4.1 Heavy
Oil............................................................................................69
2.4.2 Extra Heavy
Oil...................................................................................69
2.4.3 Tar sand
Bitumen................................................................................
71
References...................................................................................................................
74
Chapter 3 Other Feedstocks-Coal, Oil Shale, and
Biomass..................................................... 79
3.1
Introduction......................................................................................................
79
3.2
Coal..................................................................................................................
81
3.2.1 Coal
Feedstocks..................................................................................82
3.2.2 Properties and
Composition................................................................83
3.2.3
Conversion...........................................................................................83
3.2.4 Coal Tar
Chemicals.............................................................................85
3.3 Oil
Shale...........................................................................................................90
3.3.1 Shale Oil
Production...........................................................................90
3.3.2 Shale Oil
Properties............................................................................
91
3.3.2.1 Hydrocarbon
Products.........................................................92
3.3.2.2 Nitrogen-Containing
Compounds.......................................93
3.3.2.3 Oxygen-Containing
Compounds.........................................94
3.3.2.4 Sulfur-Containing
Compounds...........................................94
3.4
Biomass............................................................................................................94
3.4.1 Biomass
Feedstocks............................................................................97
3.4.1.1
Carbohydrates......................................................................99
3.4.1.2 Vegetable
Oils......................................................................99
3.4.1.3 Plant
Fibers..........................................................................99
3.4.2
Biorefining.........................................................................................
100
3.4.2.1
Pyrolysis............................................................................
103
3.4.2.2
Gasification........................................................................
103
3.4.2.3 Anaerobic
Digestion.......................................................... 107
3.4.2.4
Fermentation......................................................................
110
3.4.3 Chemicals from
Biomass..................................................................
111
3.4.3.1 Gaseous
Products............................................................... 111
3.4.3.2 Liquid
Products..................................................................
112
3.4.3.3 Solid
Products....................................................................
114
3.5
Waste..............................................................................................................
114
References.................................................................................................................
115
Chapter 4 Feedstock
Preparation...............................................................................................
119
4.1
Introduction....................................................................................................
119
4.2 Gas
Streams....................................................................................................
120
4.2.1
Sources..............................................................................................
121
4.2.1.1 Gas Streams from Natural
Gas.......................................... 121
4.2.1.2 Natural Gas Liquids and Liquefied Petroleum Gas........... 123
4.2.1.3 Gas Streams from Crude
Oil.............................................124
4.2.2 Gas
Processing..................................................................................
127
4.2.2.1 Acid Gas
Removal............................................................. 128
4.2.2.2 Recovery of Condensable Hydrocarbon Derivatives......... 137
4.2.2.3 Water
Removal..................................................................
142
4.2.2.4 Nitrogen
Removal.............................................................. 145
4.2.2.5 The Claus
Process.............................................................. 145
4.3 Petroleum
Streams..........................................................................................
147
4.3.1 Refinery
Configuration......................................................................
149
4.3.2 Cracking
Processes...........................................................................
150
4.3.2.1 Thermal Cracking
Processes............................................. 150
4.3.2.2 Catalytic Cracking
Processes............................................ 153
4.3.3 Dehydrogenation
Processes...............................................................
155
4.3.4 Dehydrocyclization
Processes........................................................... 157
4.4 Streams from Coal, Oil Shale, and
Biomass.................................................. 158
4.4.1
Coal...................................................................................................
158
4.4.1.1 Coal
Gas............................................................................
158
4.4.1.2 Coal
Liquids......................................................................
158
4.4.2 Oil
Shale............................................................................................
159
4.4.2.1 Oil Shale
Gas.....................................................................
159
4.4.2.2 Shale
Oil............................................................................
160
4.4.3
Biomass.............................................................................................
161
4.4.3.1
Biogas................................................................................
161
4.4.3.2
Bio-liquids.........................................................................
161
References.................................................................................................................
162
Chapter 5 Feedstock Preparation by
Gasification......................................................................
165
5.1
Introduction....................................................................................................
165
5.2 Gasification
Chemistry...................................................................................
168
5.2.1 General
Aspects................................................................................
169
5.2.2
Pretreatment......................................................................................
170
5.2.3
Reactions...........................................................................................
171
5.2.3.1 Primary
Gasification.......................................................... 174
5.2.3.2 Secondary
Gasification...................................................... 174
5.2.3.3 Water-Gas Shift
Reaction.................................................. 176
5.2.3.4 Carbon Dioxide
Gasification............................................. 177
5.2.3.5
Hydrogasification...............................................................
178
5.2.3.6
Methanation.......................................................................
178
5.3 Gasification
Processes....................................................................................
179
5.3.1
Gasifiers.............................................................................................
180
5.3.2 FT
Synthesis......................................................................................
181
5.3.3
Feedstocks.........................................................................................
183
5.3.3.1 Heavy
Feedstocks..............................................................
183
5.3.3.2 Solvent Deasphalter
Bottoms............................................. 184
5.3.3.3 Asphalt, Tar, and
Pitch...................................................... 184
5.3.3.4 Petroleum
Coke.................................................................. 186
5.3.3.5
Coal....................................................................................
188
5.3.3.6
Biomass..............................................................................
189
5.3.3.7 Solid
Waste........................................................................
191
5.3.3.8 Black
Liquor......................................................................
193
5.4 Gasification in a
Refinery...............................................................................
193
5.4.1 Gasification of Heavy
Feedstocks..................................................... 195
5.4.2 Gasification of Heavy Feedstocks with
Coal.................................... 195
5.4.3 Gasification of Heavy Feedstocks with
Biomass.............................. 196
5.4.4 Gasification of Heavy Feedstocks with
Waste.................................. 198
5.5 Gas Production and Other
Products............................................................... 198
5.5.1 Gaseous
Products..............................................................................
199
5.5.1.1 Synthesis
Gas.....................................................................
199
5.5.1.2 Low Btu
Gas......................................................................200
5.5.1.3 Medium Btu
Gas................................................................200
5.5.1.4 High Btu
Gas.....................................................................
201
5.5.2 Liquid
Products.................................................................................
201
5.5.3 Solid
Products...................................................................................202
5.6 The
Future......................................................................................................202
References.................................................................................................................204
Chapter 6 Chemicals from Paraffin
Hydrocarbons...................................................................209
6.1
Introduction....................................................................................................209
6.2
Methane..........................................................................................................
211
6.2.1 Physical
Properties............................................................................
212
6.2.2 Chemical
Properties..........................................................................
213
6.2.3 Chemicals from
Methane..................................................................
215
6.2.3.1 Carbon
Disulfide................................................................
216
6.2.3.2
Ethylene.............................................................................
217
6.2.3.3 Hydrogen
Cyanide............................................................. 218
6.2.3.4 Chloromethane
Derivatives............................................... 218
6.2.3.5 Synthesis
Gas.....................................................................220
6.2.3.6
Urea....................................................................................223
6.2.3.7 Methyl
Alcohol..................................................................223
6.2.3.8
Formaldehyde....................................................................226
6.2.3.9 Aldehyde
Derivatives.........................................................229
6.2.3.10 Ethylene
Glycol..................................................................229
6.2.3.11
Nitration.............................................................................230
6.2.3.12
Oxidation...........................................................................230
6.2.3.13 Carboxylic
Acids............................................................... 231
6.2.3.14
Alkylation..........................................................................
231
6.2.3.15
Thermolysis.......................................................................
232
6.2.4 Oxidative
Coupling...........................................................................
233
6.3
Ethane.............................................................................................................
235
6.3.1 Physical
Properties............................................................................
235
6.3.2 Chemical
Properties..........................................................................236
6.3.3 Chemicals from
Ethane.....................................................................
237
6.4
Propane...........................................................................................................238
6.4.1 Physical
Properties............................................................................238
6.4.2 Chemical
Properties..........................................................................
239
6.4.3 Chemicals from
Propane...................................................................240
6.4.3.1
Oxidation...........................................................................240
6.4.3.2
Chlorination.......................................................................240
6.4.3.3
Dehydrogenation................................................................
241
6.4.3.4
Nitration.............................................................................
247
6.5 Butane
Isomers...............................................................................................
247
6.5.1 Physical
Properties............................................................................249
6.5.2 Chemical
Properties..........................................................................249
6.5.3 Chemicals from
Butane.....................................................................250
6.5.3.1
Oxidation...........................................................................250
6.5.3.2 Production of
Aromatics.................................................... 252
6.5.3.3
Isomerization.....................................................................
252
6.5.4 Chemicals from
Isobutane................................................................
252
6.6 Liquid Petroleum Fractions and
Residues...................................................... 252
6.6.1
Naphtha.............................................................................................254
6.6.1.1 Physical
Properties............................................................254
6.6.1.2 Chemical
Properties.......................................................... 255
6.6.1.3 Chemicals from
Naphtha...................................................256
6.6.2
Kerosene............................................................................................
257
6.6.2.1 Physical
Properties............................................................ 257
6.6.2.2 Chemical
Properties.......................................................... 257
6.6.2.3 Chemicals from
Kerosene................................................. 258
6.6.3 Gas
Oil..............................................................................................
258
6.6.3.1 Physical
Properties............................................................ 258
6.6.3.2 Chemical
Properties.......................................................... 259
6.6.3.3 Chemicals from Gas
Oil.................................................... 259
6.6.4 Fuel
Oil..............................................................................................260
6.6.4.1 Physical
Properties............................................................ 261
6.6.4.2 Chemical
Properties.......................................................... 261
6.6.4.3 Chemicals from Fuel
Oil................................................... 262
6.6.5
Resids................................................................................................
262
6.6.5.1 Physical
Properties............................................................263
6.6.6 Used Lubricating
Oil.........................................................................263
6.6.7 Naphthenic
Acids..............................................................................263
6.6.8 Chemicals from Liquid Petroleum Fractions and
Residues..............264
6.6.8.1
Oxidation...........................................................................265
6.6.8.2
Chlorination.......................................................................265
6.6.8.3
Sulfonation.........................................................................265
6.6.8.4 Other
Products...................................................................266
References.................................................................................................................266
Chapter 7 Chemicals from Olefin
Hydrocarbons......................................................................269
7.1
Introduction....................................................................................................269
7.2 Chemicals from
Ethylene...............................................................................
271
7.2.1
Alcohols............................................................................................
273
7.2.2
Alkylation..........................................................................................
275
7.2.3 Halogen
Derivatives..........................................................................
276
7.2.4 Oxygen
Derivatives...........................................................................277
7.2.4.1 Ethylene
Glycol..................................................................
279
7.2.4.2
Ethoxylates.........................................................................
281
7.2.4.3
Ethanolamines...................................................................282
7.2.4.4
1,3-Propanediol..................................................................282
7.2.4.5
Acetaldehyde.....................................................................283
7.2.5
Carbonylation....................................................................................285
7.2.6
Chlorination......................................................................................286
7.2.6.1 Vinyl
Chloride...................................................................286
7.2.6.2 Perchloroethylene and
Trichloroethylene..........................287
7.2.7
Hydration...........................................................................................287
7.2.8
Oligomerization.................................................................................288
7.2.9
Polymerization..................................................................................289
7.2.10 1
-Butylene..........................................................................................290
7.2.11
Polymerization..................................................................................290
7.3 Chemicals from
Propylene.............................................................................
291
7.3.1
Oxidation...........................................................................................294
7.3.2
Ammoxidation...................................................................................296
7.3.3
Oxyacylation......................................................................................299
7.3.4
Chlorination......................................................................................300
7.3.5
Hydration...........................................................................................300
7.3.6 Addition of Organic
Acids................................................................302
7.3.7
Hydroformylation..............................................................................302
7.3.8
Disproportionation............................................................................303
7.3.9
Alkylation..........................................................................................303
7.4 Chemicals from C4
Olefins.............................................................................303
7.4.1
Butylene.............................................................................................304
7.4.1.1
Oxidation...........................................................................306
7.4.1.2
Hydration...........................................................................308
7.4.1.3
Isomerization.....................................................................309
7.4.1.4
Metathesis..........................................................................309
7.4.1.5
Oligomerization.................................................................
310
7.4.2
Isobutylene........................................................................................
310
7.4.2.1
Oxidation...........................................................................
311
7.4.2.2
Epoxidation........................................................................
311
7.4.2.3 Addition of
Alcohols......................................................... 312
7.4.2.4
Hydration...........................................................................
312
7.4.2.5
Carbonylation....................................................................
312
7.4.2.6 Dimerization...........
Preface..............................................................................................................................................xv
About the
Author............................................................................................................................xvii
Chapter 1 The Petrochemical
Industry..........................................................................................1
1.1
Introduction........................................................................................................1
1.2 Historical Aspects and
Overview.....................................................................
10
1.3 The Petrochemical
Industry.............................................................................
11
1.4
Petrochemicals..................................................................................................
17
1.4.1 Primary
Petrochemicals......................................................................
19
1.4.2 Products and End
Use.........................................................................
19
1.5 Production of
Petrochemicals...........................................................................20
1.6 The
Future........................................................................................................24
References...................................................................................................................29
Chapter 2 Feedstock Composition and
Properties.......................................................................
31
2.1
Introduction......................................................................................................
31
2.2 Natural
Gas.......................................................................................................
31
2.2.1 Composition and
Properties................................................................
33
2.2.2 Natural Gas
Liquids............................................................................
42
2.2.3 Gas
Condensate...................................................................................
43
2.2.4 Gas
Hydrates.......................................................................................44
2.2.5 Other Types of
Gases..........................................................................46
2.2.5.1
Biogas..................................................................................
47
2.2.5.2 Coalbed
Methane.................................................................48
2.2.5.3 Coal
Gas..............................................................................49
2.2.5.4 Geopressurized
Gas............................................................. 51
2.2.5.5 Landfill
Gas.........................................................................
51
2.2.5.6 Refinery
Gas........................................................................
53
2.2.5.7 Synthesis
Gas.......................................................................
57
2.2.5.8 Tight
Gas.............................................................................
58
2.3
Petroleum..........................................................................................................
59
2.3.1 Composition and
Properties................................................................
59
2.3.1.1 Opportunity Crude
Oil........................................................ 61
2.3.1.2 High Acid Crude
Oil........................................................... 61
2.3.1.3 Foamy
Oil............................................................................
62
2.3.1.4 Tight
Oil...............................................................................
62
2.3.2 Other Petroleum-Derived
Feedstocks.................................................63
2.3.2.1
Naphtha................................................................................63
2.3.2.2
Kerosene..............................................................................64
2.3.2.3 Fuel
Oil................................................................................65
2.3.2.4 Gas
Oil.................................................................................
67
2.3.2.5
Residua.................................................................................
67
2.3.2.6 Used Lubricating
Oil...........................................................68
2.4 Heavy Oil, Extra Heavy Oil, and Tar Sand
Bitumen.......................................68
2.4.1 Heavy
Oil............................................................................................69
2.4.2 Extra Heavy
Oil...................................................................................69
2.4.3 Tar sand
Bitumen................................................................................
71
References...................................................................................................................
74
Chapter 3 Other Feedstocks-Coal, Oil Shale, and
Biomass..................................................... 79
3.1
Introduction......................................................................................................
79
3.2
Coal..................................................................................................................
81
3.2.1 Coal
Feedstocks..................................................................................82
3.2.2 Properties and
Composition................................................................83
3.2.3
Conversion...........................................................................................83
3.2.4 Coal Tar
Chemicals.............................................................................85
3.3 Oil
Shale...........................................................................................................90
3.3.1 Shale Oil
Production...........................................................................90
3.3.2 Shale Oil
Properties............................................................................
91
3.3.2.1 Hydrocarbon
Products.........................................................92
3.3.2.2 Nitrogen-Containing
Compounds.......................................93
3.3.2.3 Oxygen-Containing
Compounds.........................................94
3.3.2.4 Sulfur-Containing
Compounds...........................................94
3.4
Biomass............................................................................................................94
3.4.1 Biomass
Feedstocks............................................................................97
3.4.1.1
Carbohydrates......................................................................99
3.4.1.2 Vegetable
Oils......................................................................99
3.4.1.3 Plant
Fibers..........................................................................99
3.4.2
Biorefining.........................................................................................
100
3.4.2.1
Pyrolysis............................................................................
103
3.4.2.2
Gasification........................................................................
103
3.4.2.3 Anaerobic
Digestion.......................................................... 107
3.4.2.4
Fermentation......................................................................
110
3.4.3 Chemicals from
Biomass..................................................................
111
3.4.3.1 Gaseous
Products............................................................... 111
3.4.3.2 Liquid
Products..................................................................
112
3.4.3.3 Solid
Products....................................................................
114
3.5
Waste..............................................................................................................
114
References.................................................................................................................
115
Chapter 4 Feedstock
Preparation...............................................................................................
119
4.1
Introduction....................................................................................................
119
4.2 Gas
Streams....................................................................................................
120
4.2.1
Sources..............................................................................................
121
4.2.1.1 Gas Streams from Natural
Gas.......................................... 121
4.2.1.2 Natural Gas Liquids and Liquefied Petroleum Gas........... 123
4.2.1.3 Gas Streams from Crude
Oil.............................................124
4.2.2 Gas
Processing..................................................................................
127
4.2.2.1 Acid Gas
Removal............................................................. 128
4.2.2.2 Recovery of Condensable Hydrocarbon Derivatives......... 137
4.2.2.3 Water
Removal..................................................................
142
4.2.2.4 Nitrogen
Removal.............................................................. 145
4.2.2.5 The Claus
Process.............................................................. 145
4.3 Petroleum
Streams..........................................................................................
147
4.3.1 Refinery
Configuration......................................................................
149
4.3.2 Cracking
Processes...........................................................................
150
4.3.2.1 Thermal Cracking
Processes............................................. 150
4.3.2.2 Catalytic Cracking
Processes............................................ 153
4.3.3 Dehydrogenation
Processes...............................................................
155
4.3.4 Dehydrocyclization
Processes........................................................... 157
4.4 Streams from Coal, Oil Shale, and
Biomass.................................................. 158
4.4.1
Coal...................................................................................................
158
4.4.1.1 Coal
Gas............................................................................
158
4.4.1.2 Coal
Liquids......................................................................
158
4.4.2 Oil
Shale............................................................................................
159
4.4.2.1 Oil Shale
Gas.....................................................................
159
4.4.2.2 Shale
Oil............................................................................
160
4.4.3
Biomass.............................................................................................
161
4.4.3.1
Biogas................................................................................
161
4.4.3.2
Bio-liquids.........................................................................
161
References.................................................................................................................
162
Chapter 5 Feedstock Preparation by
Gasification......................................................................
165
5.1
Introduction....................................................................................................
165
5.2 Gasification
Chemistry...................................................................................
168
5.2.1 General
Aspects................................................................................
169
5.2.2
Pretreatment......................................................................................
170
5.2.3
Reactions...........................................................................................
171
5.2.3.1 Primary
Gasification.......................................................... 174
5.2.3.2 Secondary
Gasification...................................................... 174
5.2.3.3 Water-Gas Shift
Reaction.................................................. 176
5.2.3.4 Carbon Dioxide
Gasification............................................. 177
5.2.3.5
Hydrogasification...............................................................
178
5.2.3.6
Methanation.......................................................................
178
5.3 Gasification
Processes....................................................................................
179
5.3.1
Gasifiers.............................................................................................
180
5.3.2 FT
Synthesis......................................................................................
181
5.3.3
Feedstocks.........................................................................................
183
5.3.3.1 Heavy
Feedstocks..............................................................
183
5.3.3.2 Solvent Deasphalter
Bottoms............................................. 184
5.3.3.3 Asphalt, Tar, and
Pitch...................................................... 184
5.3.3.4 Petroleum
Coke.................................................................. 186
5.3.3.5
Coal....................................................................................
188
5.3.3.6
Biomass..............................................................................
189
5.3.3.7 Solid
Waste........................................................................
191
5.3.3.8 Black
Liquor......................................................................
193
5.4 Gasification in a
Refinery...............................................................................
193
5.4.1 Gasification of Heavy
Feedstocks..................................................... 195
5.4.2 Gasification of Heavy Feedstocks with
Coal.................................... 195
5.4.3 Gasification of Heavy Feedstocks with
Biomass.............................. 196
5.4.4 Gasification of Heavy Feedstocks with
Waste.................................. 198
5.5 Gas Production and Other
Products............................................................... 198
5.5.1 Gaseous
Products..............................................................................
199
5.5.1.1 Synthesis
Gas.....................................................................
199
5.5.1.2 Low Btu
Gas......................................................................200
5.5.1.3 Medium Btu
Gas................................................................200
5.5.1.4 High Btu
Gas.....................................................................
201
5.5.2 Liquid
Products.................................................................................
201
5.5.3 Solid
Products...................................................................................202
5.6 The
Future......................................................................................................202
References.................................................................................................................204
Chapter 6 Chemicals from Paraffin
Hydrocarbons...................................................................209
6.1
Introduction....................................................................................................209
6.2
Methane..........................................................................................................
211
6.2.1 Physical
Properties............................................................................
212
6.2.2 Chemical
Properties..........................................................................
213
6.2.3 Chemicals from
Methane..................................................................
215
6.2.3.1 Carbon
Disulfide................................................................
216
6.2.3.2
Ethylene.............................................................................
217
6.2.3.3 Hydrogen
Cyanide............................................................. 218
6.2.3.4 Chloromethane
Derivatives............................................... 218
6.2.3.5 Synthesis
Gas.....................................................................220
6.2.3.6
Urea....................................................................................223
6.2.3.7 Methyl
Alcohol..................................................................223
6.2.3.8
Formaldehyde....................................................................226
6.2.3.9 Aldehyde
Derivatives.........................................................229
6.2.3.10 Ethylene
Glycol..................................................................229
6.2.3.11
Nitration.............................................................................230
6.2.3.12
Oxidation...........................................................................230
6.2.3.13 Carboxylic
Acids............................................................... 231
6.2.3.14
Alkylation..........................................................................
231
6.2.3.15
Thermolysis.......................................................................
232
6.2.4 Oxidative
Coupling...........................................................................
233
6.3
Ethane.............................................................................................................
235
6.3.1 Physical
Properties............................................................................
235
6.3.2 Chemical
Properties..........................................................................236
6.3.3 Chemicals from
Ethane.....................................................................
237
6.4
Propane...........................................................................................................238
6.4.1 Physical
Properties............................................................................238
6.4.2 Chemical
Properties..........................................................................
239
6.4.3 Chemicals from
Propane...................................................................240
6.4.3.1
Oxidation...........................................................................240
6.4.3.2
Chlorination.......................................................................240
6.4.3.3
Dehydrogenation................................................................
241
6.4.3.4
Nitration.............................................................................
247
6.5 Butane
Isomers...............................................................................................
247
6.5.1 Physical
Properties............................................................................249
6.5.2 Chemical
Properties..........................................................................249
6.5.3 Chemicals from
Butane.....................................................................250
6.5.3.1
Oxidation...........................................................................250
6.5.3.2 Production of
Aromatics.................................................... 252
6.5.3.3
Isomerization.....................................................................
252
6.5.4 Chemicals from
Isobutane................................................................
252
6.6 Liquid Petroleum Fractions and
Residues...................................................... 252
6.6.1
Naphtha.............................................................................................254
6.6.1.1 Physical
Properties............................................................254
6.6.1.2 Chemical
Properties.......................................................... 255
6.6.1.3 Chemicals from
Naphtha...................................................256
6.6.2
Kerosene............................................................................................
257
6.6.2.1 Physical
Properties............................................................ 257
6.6.2.2 Chemical
Properties.......................................................... 257
6.6.2.3 Chemicals from
Kerosene................................................. 258
6.6.3 Gas
Oil..............................................................................................
258
6.6.3.1 Physical
Properties............................................................ 258
6.6.3.2 Chemical
Properties.......................................................... 259
6.6.3.3 Chemicals from Gas
Oil.................................................... 259
6.6.4 Fuel
Oil..............................................................................................260
6.6.4.1 Physical
Properties............................................................ 261
6.6.4.2 Chemical
Properties.......................................................... 261
6.6.4.3 Chemicals from Fuel
Oil................................................... 262
6.6.5
Resids................................................................................................
262
6.6.5.1 Physical
Properties............................................................263
6.6.6 Used Lubricating
Oil.........................................................................263
6.6.7 Naphthenic
Acids..............................................................................263
6.6.8 Chemicals from Liquid Petroleum Fractions and
Residues..............264
6.6.8.1
Oxidation...........................................................................265
6.6.8.2
Chlorination.......................................................................265
6.6.8.3
Sulfonation.........................................................................265
6.6.8.4 Other
Products...................................................................266
References.................................................................................................................266
Chapter 7 Chemicals from Olefin
Hydrocarbons......................................................................269
7.1
Introduction....................................................................................................269
7.2 Chemicals from
Ethylene...............................................................................
271
7.2.1
Alcohols............................................................................................
273
7.2.2
Alkylation..........................................................................................
275
7.2.3 Halogen
Derivatives..........................................................................
276
7.2.4 Oxygen
Derivatives...........................................................................277
7.2.4.1 Ethylene
Glycol..................................................................
279
7.2.4.2
Ethoxylates.........................................................................
281
7.2.4.3
Ethanolamines...................................................................282
7.2.4.4
1,3-Propanediol..................................................................282
7.2.4.5
Acetaldehyde.....................................................................283
7.2.5
Carbonylation....................................................................................285
7.2.6
Chlorination......................................................................................286
7.2.6.1 Vinyl
Chloride...................................................................286
7.2.6.2 Perchloroethylene and
Trichloroethylene..........................287
7.2.7
Hydration...........................................................................................287
7.2.8
Oligomerization.................................................................................288
7.2.9
Polymerization..................................................................................289
7.2.10 1
-Butylene..........................................................................................290
7.2.11
Polymerization..................................................................................290
7.3 Chemicals from
Propylene.............................................................................
291
7.3.1
Oxidation...........................................................................................294
7.3.2
Ammoxidation...................................................................................296
7.3.3
Oxyacylation......................................................................................299
7.3.4
Chlorination......................................................................................300
7.3.5
Hydration...........................................................................................300
7.3.6 Addition of Organic
Acids................................................................302
7.3.7
Hydroformylation..............................................................................302
7.3.8
Disproportionation............................................................................303
7.3.9
Alkylation..........................................................................................303
7.4 Chemicals from C4
Olefins.............................................................................303
7.4.1
Butylene.............................................................................................304
7.4.1.1
Oxidation...........................................................................306
7.4.1.2
Hydration...........................................................................308
7.4.1.3
Isomerization.....................................................................309
7.4.1.4
Metathesis..........................................................................309
7.4.1.5
Oligomerization.................................................................
310
7.4.2
Isobutylene........................................................................................
310
7.4.2.1
Oxidation...........................................................................
311
7.4.2.2
Epoxidation........................................................................
311
7.4.2.3 Addition of
Alcohols......................................................... 312
7.4.2.4
Hydration...........................................................................
312
7.4.2.5
Carbonylation....................................................................
312
7.4.2.6 Dimerization...........