ACRYLAMIDE AND POLYACRYLAMIDE - IHS Markit … · Polymerization Processes ... Anionic...
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Report No. 99 ACRYLAMIDE AND POLYACRYLAMIDE by YEN-CHEN YEN June 1976 A private report by the PROCESS ECONOMICS PROGRAM STANFORD RESEARCH INSTITUTE I MENLO PARK. CALIFORNIA
Transcript of ACRYLAMIDE AND POLYACRYLAMIDE - IHS Markit … · Polymerization Processes ... Anionic...
Report No. 99
ACRYLAMIDE AND POLYACRYLAMIDE
by YEN-CHEN YEN
e
June 1976
a A private report by the
PROCESS ECONOMICS PROGRAM
l STANFORD RESEARCH INSTITUTE
I
MENLO PARK. CALIFORNIA
a
CONTENTS
1 INTRODUCTION . . . . . . , . . . . . . . . . . . . . . . . . .
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2 SUMMARY ............................
Acrylamide .......................... General Aspects ...................... Technical Aspects .....................
Acrylamide Polymers ..................... General Aspects ...................... Technical Aspects .....................
3 INDUSTRY STATUS .......................
Production Capacity ...................... Production and Consumption .................. Commercial Acrylamide Commercial Polyacrylamidls' ....................................
4 APPLICATIONS OF ACRYLAMIDE AND POLYACRYLAMIDE ........
As Flocculants ........................ For Waste Water Treatment ................. For Potable Water Treatment ................ For Various Process Industries ............... For the Mining Industry ..................
In Oil Production . .. .. Mobility Control Agent'& Wa;e; kodi;g'for Oil Recovery
........
Additive for Oil Well Drilling Fluids .......... Aid in Fracturing, Acidifying, and Other'Operations Relating to Oil Production ................
In the Paper and Pulp Industry ................ Additives for Paper .................... Coating for Paper ..................... Other Uses in the Paper and Pulp Industry .........
In the Textile Industry ................... Coating for Materials Other than Paper and Textiles ..... Construction and Civil Engineering Uses ........... Adhesives .......................... Agricultural Uses ...................... Plastics or Plastics Additives ................ OtherUses ..........................
5 COMPARISON OF PROCESSES ...................
Making Acrylamide ....................... Polymerization Processes ................... Producing Anionic Polyacrylamides .............. Polymerization at Site with Purchase of Polymer .......
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4 4 6 7 7 12
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19 19 24 24
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27 27 29 29 29 30 30 31
32 33 33 35 36 36 38 38 39 39 40 40
43
43 46 46 48
CONTENTS
6 ACRYLAMIDE BY THE SULFURIC ACID PROCESS ........... 53
Chemistry .......................... 53
Review of Processes ..................... 53
Process Description ..................... 62
Process Discussion ..................... 68
Cost Estimate ........................ 68
7 ACRYLAMIDE BY CATALYTIC HYDRATION OF ACRYLONITRILE . . . . . 73
Chemistry .............. Review of Pa&n; literature
.
Reactant and Reaction Medium ......... ........
Catalyst Reaction CoAditions .............................. Recovery of Acrylamide An Electrochemical Procesi
.......... .........
Process Evaluations .............. A Fixed Bed Catalyst Process ........ Process Description ............ Process Discussion ............ Cost Estimate ...............
A Suspended Catalyst Process ........ Process Description ............ Process Discussion ............ Cost Estimate ...............
Conversion of 50% Solution to Solid Acrylamide
....... 73
....... 73
....... 83
....... 83
....... 84
....... 84
....... 85
....... 85
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....... 92
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....... 96
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....... 102
....... 102 ...... 102
8 POLYMERIZATION OF ACRYLAMIDE . . . . ............. 109
Mechanism . . . . . . . . . . . . . ............. 109
Catalyst for Polymerization . . . . ............. 110
Inorganic Compounds Acting Alone 111 Organic Compounds Containing P, B, As,orMetals
................. 111
Organic Compounds . . . . . . . . ............. 111 Redox Compounds . . . . . . . . . ............. 112
Kinetics . . . . . . . . . . . . . . ............. 115 Polymerization Processes . . . . . ............. 118 Bulk Polymerization . . . . . . . ............. 118 Solution Polymerization . . . . . ............. 119 Precipitation Polymerization . . ............. 130 Suspension Polymerization . . . . ............. 132 Emulsion Polymerization . . . . . ............. 132
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CONTENTS
8 POLYMERIZATION OF ACRYLAMIDE (Continued)
Feedstock for Polymerization ................ 136 Polymerization Equipment .................. 140 Removal of Residual Monomer Photo-activated Polymerization' ..............................
143 143
Radiation Polymerization .................. 144 Polymerization with Other Kinds of Initiation ....... 148
9 EVALUATION OF PROCESSES FOR ACRYLAMIDE POLYMERIZATION ... 149
A Solution Process for Medium Molecular Weight Polyacrylamide Process Description ........................................
149 149
Process Discussion .................... 154 Cost Estimate ...................... 155
A Solution Process for High Molecular Weight Polyacrylamide ..................... Process Description
155 ................... 155
Process Discussion .................... 162 Cost Estimate .... .........
A Solution Process'for'V$ $h'MAlecular Weight 163
Polyacrylamide Process Descriptio;
.................... 163 ................... 163
Process Discussion .................... 171 Cost Estimate . ... ..... .......
A Solution Process'fir Eitremeiy'High Molecular Weight 171
Polyacrylamide ...................... 175 Process Description ................... 175 Process Discussion .................... 180 Cost Estimate ..
An Emulsion Procesi for Polyic;yiamide .......................... 180 180
Process Description ................... 180 Process Discussion .................... 188 Cost Estimate ....................... 189
A Precipitation Process for Polyacrylamide ......... 189 Process Description ................... 189 Process Discussion .................... 197 Cost Estimate ....................... 197
10 DERIVATIVES OF POLYACRYLAMIDE ............... 201
Review of Products and Processes .............. 201 Partially Hydrolyzed Polyacrylamide ........... 201 Methylolated Polyacrylamide ............... 205
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CONTENTS
10 DERIVATIVES OF POLYACRYLAMIDE (Continued)
Sulfomethylated Polyacrylamide ..............
Mannich Reaction Product .................
Hoffman Degradation Product ...............
Other Cationic Polyacrylamides .............. Insoluble Polyacrylamides ................
Grafted Polyacrylamides ..................
Other Derivatives ....................
Process Evaluations ....................
Anionic Polyacrylamide by Simultaneous Polymerization and Hydroysis ........................ Process Description ..................
Cost Estimate ......................
A Process for Making Partially Hydrolyzed Polyacrylamide With Very High Molecular Weight .............
Process Description ..................
Cost Estimate ......................
A Process for Making Partially Hydrolyzed Polyacrylamide With High Molecular Weight ...............
Process Description ..................
Cost Estimate ...................... A Process for Making a Mannich Reaction Product of Polyacrylamide Process Descriptio: .....................................
Cost Estimate .... ........ Sulfomethylated Poiyac&iaiide'with Medium Molecular Weight .. ........ . .... Sulfomethyiated Polyacrylamide in Dilute Solution
.............
11 COPOLYMERIZATION OF ACRYLAMIDE ...............
Review of Products and Processes ..............
Kinetics ......................... Review of Patents on Copolymers .............
Copolymerization Processes ................
Catalysts for Copolymerization .............. Copolymerization Equipment ................ Recovery of Product ...................
Process Evaluations ....................
Copolymerization of Acrylamide and Sodium Acrylate in Emulsion ........................
207 209 209 211 214 216 216 216
216 216 222
226 226 226
226 229 230
230 230 230
238 238
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245 245 248 272 274 274 274 275
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CONTENTS
11 COPOLYMERIZATION OF ACRYLAMIDE (Continued)
Copolymerization of Acrylamide and Acrylic Acid in the Presence of Salt . . . . . . . . . . . . . . . . . . . . . 275 Copolymerization of Acrylamide, Methacrylic Acid and Maleic Anhydride . . . . . . . . . . . . . . . . . . . . . 278 A Process for Making a Cationic Polyacrylamide Containing Diallyldimethylammonium Chloride . . . . . . . . . . . . . 278 A Process for Making a Cationic Polyacrylamide Containing Quaternized Dimethylaminoethyl Methacrylate . . . . . A Process for Making a Cationic Copolymer of Aciyiamide and
280
2-Methyl-5-Vinylpyridine . . . . . . . . . . . . . . . . . 281
12 POLYACRYLAMIDE FROM POLYACRYLONITRILE ............ 285
Process Description ..................... 285 Process Discussion ..................... 290 Cost Estimate ........................ 290
13 OTHER PROCESSES FOR MAKING ACRYLAMIDE AND POLYACRYLAMIDE ... 295
Acrylamide .... ....... .. From AcryloAi;rili through Hydrochloric Acid Hydrolysis ..........
295 295
From Acrylylchloride ................... 295 From Hydracrylamide or B-Alkoxy-propionamide ....... 295 From 8-Dialkylamino-propionamide ............. 296 From Aldehyde Cyanhydrin .................. 296 From Acrylic Anhydride .................. 296 From Ethylene, Carbon Monoxide and Ammonia ........ 296 By Pyrolysis of Acetoxypropionamide ............ 296 From Alkyl Acrylate ..................... 296
Polyacrylamide from Polyacrylate or Polyacrylylchloride ... 296
APPENDIX A DESIGN AND COST BASES . . . . . . . . . . . . . . . . 297
APPENDIX B PHYSICAL PROPERTIES OF ACRYLAMIDE AND ACRYLAMIDE SOLUTIONS . . . . . . . . . . . . . . . . 299
APPENDIX C PROPERTIES OF POLYACRYLAMIDE . . . . . . . . . . . . 303
APPENDIX D TOXICITY . . . . . . . . . . . . . . . . . . . . . . 307
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APPENDIX E DISSOLUTION OF POLYACRYLAMIDE ............ 309
APPENDIX F THERMOCHEMICAL DATA ................. 311
CITED REFERENCES ........................ 313
PATENT REFERENCES BY COMPANY .................. 359
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ILLUSTRATIONS
5.1 Manufacture of Acrylamide Comparison of Process Economics . . . . . . . . . . . . . . 44
5.2 Polymerization of Acrylamide Comparison of Process Economics . . . . . . . . . . . . . . 47
5.3 Anionic Polyacrylamide Manufacture (27% Hydrolyzed) Comparison of Process Economics . . . . . . . . . . . . . . 50
6.1 Acrylamide by the Sulfuric Acid Process . . . . . . . . . . 375
6.2 Acrylamide by the Sulfuric Acid Process Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . . . 72
7.1 Acrylamide by Hydration of Acrylonitrile Using Fixed Bed Catalyst . . . . . . . . , . . . . . . . . . . . . . . 377
7.2 Acrylamide by Hydration of Acrylonitrile Using Fixed Bed Catalyst Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . . . 95
7.3 Acrylamide by Hydration of Acrylonitrile Using Suspended Catalyst . . . . . . . . . . . . . . . . . . , . 379
7.4 Acrylamide by Hydration of Acrylonitrile Using Suspended Catalyst Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . . . 105
7.5 Conversion of 50% Solution to Solid Acrylamide . . . . . . 107
9.1 Polyacrylamide with Medium Molecular Weight by a Solution Process . . . . . . . . . . . . . . . . . . . . . . 381
9.2 Polyacrylamide with Medium Molecular Weight by a Solution Process Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . . . 158
9.3 Polyacrylamide with High Molecular Weight by a Solution Process . . . . . . . . . . . . . . . . . . . . . . 383
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ILLUSTRATIONS
9.4 Polyacrylamide with High Molecular Weight by a Solution Process Effect of Operating Level and Plant Capacity on Production Cost , . . . . . . . . . . . . . . . . . . . . . 166
9.5 Polyacrylamide with Very High Molecular Weight by a Solution Process . . , . . . . . . . . . . . . . . . . . . 385
9.6 Polyacrylamide with Very High Molecular Weight by a Solution Process Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . . . 174
9.7 Polyacrylamide with Extremely High Molecular Weight by a Solution Process . . . . . . . . . . . . . . . . . . . . . 387
9.8 Polyacrylamide with Extremely High Molecular Weight by a Solution Process Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . . . 183
9.9 Polyacrylamide by an Emulsion Process . . . . . . . . . . . 389
9.10 Polyacrylamide by an Emulsion Process Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . . . 192
9.11 Polyacrylamide by a Precipitation Process . . . . . . . . . 391
9.12 Polyacrylamide by a Precipitation Process Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . . . 200
10.1 Anionic Polyacrylamide by Simultaneous Polymerization and Hydrolysis . . . . . . . . . . . . . . . 393
10.2 Anionic Polyacrylamide by Simultaneous Polymerization and Hydrolysis Effect of Operating Level and Plant Capacity on Production Cost . . . . . , . . . . . . . . . . . . . . . . 225
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ILLUSTRATIONS
10.3
10.4
10.5
10.6
10.7
12.1
12.2
c.1
Partially Hydrolyzed Polyacrylamide with Very High Molecular Weight Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . , . . . . . . . . . . . . . 228
Anionic Polyacrylamide with High Molecular Weight . . . . . . . . . . . . . . . . . . . . . . . . . . 231
Partially Hydrolyzed Polyacrylamide with High Molecular Weight Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . . . 234
Cationic Polyacrylamide by Mannich Reaction Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . . . 237
Sulfomethylated Polyacrylamide Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . . . 241
Anionic Polyacrylamide from Polyacrylonitrile . . . . . . . 395
Anionic Polyacrylamide from Polyacrylonitrile Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . . . 293
Viscosity of Polyacrylamide Aqueous Solution . . . . . . . 305
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TABLES
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2.1
2.2
2.3
2.4
2.5
3.1
3.2
3.3
5.1
5.2
6.1
6.2
6.3
6.4
Cost of Acrylamide Manufacture . . . . . . . . . . . . . . 5
Cost of Nonionic Acrylamide Homopolymer Manufacture . . . . . . . . . . . . . . . . . . . . . . . 10
Cost of Anionic Polyacrylamide Manufacture by After-treatment . . . . . . . . . . . . . . . . . . . . . 11
Cost of Anionic Acrylamide Copolymer Manufacture . . . . . . . . . . . . . . . . . . . . . . . 13
Cost of Cationic Polyacrylamide Manufacture . . . . . . . 14
Producers of Acrylamide . . . . . s . . . . . . . . . . . 20
Producers of Polyacrylamide . . . . . . . . . . . . . . . 21
Estimated End-Use Pattern for Polyacrylamides . . . . . . 23
Comparison of Processes for Polymerization of Acrylamide . . . . . . . . . . . . . . . . . . . . . . . . 45
Comparison of Processes for Producing Anionic Polyacrylamide . . . . . . . . . . . . . . . . . . . . . . 49
Acrylamide by Sulfuric Acid Process--Hydrolysis and Neutralization Patent Summary . . . . . . . . . . . . . . . . . . . . . . 54
Acrylamide by Sulfuric Acid Process--Purification and Related Operations Patent Summary . . . . . . . . . . . . . . . . . . . . . . 58
Acrylamide by Sulfuric Acid Process Design Bases and Assumptions . . . . . . . . . . . . . . . 64
Acrylamide by Sulfuric Acid Process Major Process Equipment and Utilities Summary . . . . . . 65
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TABLES
6.5
6.6
6.7
7.1
7.2
7.3
7.4
7.5
7.6
7.7
7.8
7 ..9
Acrylamide by Sulfuric Acid Process Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . 67
Acrylamide by Sulfuric Acid Process Total Capital Investment . . . . . . . . . . . . . . . . . . 70
Acrylamide by Sulfuric Acid Process Production Costs . . . . . . . . . . . . . . . . . . . . . . 71
Acrylamide by Catalytic Hydration of Acrylonitrile Patent Summary . . . . . . . . . . . . . . . . . . . . . . . 74
Acrylamide by Catalytic Hydration of Acrylonitrile-- Purification, Concentration and Handling Patent Summary . . . . . . . . . . . . . . . . . . . . . . . 82
Acrylamide by Hydration of Acrylonitrile Using Fixed Bed Catalyst Design Bases and Assumptions . . . . . . . . . . , . . . . . 87
Acrylamide by Hydration of Acrylonitrile Using Fixed Bed Catalyst Major Process Equipment and Utilities Suwtary . . . . . . . 88
Acrylamide by Hydration of Acrylonitrile Using Fixed Bed Catalyst Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . 90
Acrylamide by Hydration of Acrylonitrile Using Fixed Bed Catalyst Total Capital Investment . . . :. . . . . . . . . . . . . . 93
Acrylamide by Hydration of Acrylonitrile Using Fixed Bed Catalyst Production Costs . . . . . . . . . . . . . . . . . . . . . . 94
Acrylonitrile by Hydration of Acrylonitrile Using Suspended Catalyst Design Bases and Assumptions . . . . . . . . . . . . . . . . 97
Acrylamide by Hydration of Acrylonitrile Using Suspended Catalyst Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . 98
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7.10 Acrylamide by Hydration of Acrylonitrile Using Suspended Catalyst Major Process Equipment and Utilities Summary . . . . . . . 99
7.11 Acrylamide by Hydration of Acrylonitrile Using Suspended Catalyst Total Capital Investment . . . . . . . . . . . . . . . . . 103
7.12 Acrylamide by Hydration of Acrylonitrile Using Suspended Catalyst Production Costs . . . . . . . . . . . . . . . . . . . . . 104
7.13 Conversion of 50% Solution to Solid Acrylamide Stream Flows . . . . . . . . . . . . . . . . . . . . . . . 108
7.14 Acrylamide by Hydration of Acrylonitrile Using Suspended Catalyst Comparison of Costs for Producing Solution or Solid Acrylamide . . . . . . . . . . . . . . . . . . . . . 108
8.1 Polymerization of Acrylamide in Aqueous Solution Patent Summary . . . . . . . . . . . . . . . . . . . . . . 120
8.2 Recovery of Polyacrylamide as Solid from an Aqueous Reaction Product Patent Summary . . . . . . . . . . . . . . . . . . . . . . 127
8.3 Means for Improving the Dissolution of Polyacrylamide Patent Summary . . . . . . . . . . . . . . . . . . . . . . 129
8.4 Stabilizers for Polyacrylamide Patent Summary . . . . . . . . . . . . . . . . . . . . . . 131
8.5 Precipitation Processes for Acrylamide Polymerization Patent Summary . . . . . . . . . . . . . . . . . . . . . . 133
8.6 Polymerization of Acrylamide in Suspension of an Organic No-Solvent Liquid Patent Summary . . . . . . . . . . . . . . . . . . . . . . 134
8.7 Polymerization of Acrylamide in Oil-in-Water Emulsion Patent Summary . . . . . . . . . . . . . . . . . . . . . . 137
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TABLES
8.8 Polymerization of Acrylamide in Water-in-Oil Emulsion Patent Summary . . . . . . . , . . . . . . . . . . . . . . . 138
8.9 Equipment for Polymerization Patent Summary . . . . . . . . . . . . . . . . . . . . . . . 141
8.10 Photo-Activated Polymerization of Acrylamide Patent Summary . . . . . . . . . . . . . . . . . . . . . . . 145
8.11 Radiation Polymerization of Acrylamide Patent Sunrnary . . . . . . . . . . . . . . . . . . . . . . . 147
9.1 Processes for the Manufacture of Polyacrylamide Design Bases and Assumptions . . . . . . . . . . . . . . . . 150
9.2 Polyacrylamide with Medium Mol Wt by a Solution Process s
Major Process Equipment and Utilities Summary . . . . . . . 151
9.3 Polyacrylamide with Medium Mol Wt by a Solution Process Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . 152
9.4 Polyacrylamide with Medium Mol Wt by a Solution Process Total Capital Investment . . . . . . . . . . . . . . . . . . 156
9.5 Polyacrylamide with Medium Mol Wt by a Solution Process Production Costs . . . . . . . . . . . . . . . . . . . . . . 157
9.6 Polyacrylamide with High Mol Wt by a Solution Process Major Process Equipment and Utilities Sumnary . . . . . . . 159
9.7 Polyacrylamide with High Mol Wt by a Solution Process Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . . 160
9.8 Polyacrylamide with High Mol Wt by a Solution Process Total Capital Investment . . . . . . . . . . . . . . . . . . 164
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TABLES
9.9 Polyacrylamide with High Mol Wt by a Solution Process Production Costs . . . . . . . . . . . . . . . . . . . . . . 165
9.10 Polyacrylamide with Very High Mol Wt by a Solution Process Major Process Equipment and Utilities Summary . . . . . . . 167
9.11 Polyacrylamide with Very High Mol Wt by a Solution Process Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . 169
9.12 Polyacrylamide with Very High Mol Wt by a Solution Process Total Capital Investment . . . . . . . . . . . . . . . . . 172
9.13 Polyacrylamide with Very High Mol Wt by a Solution Process Production Costs . . . . . . . . . . . . . . . . . . . . . 173
9.14 Polyacrylamide with Extremely High MoL Wt by a Solution Process Major Process Equipment and Utilities Summary . . . . . . . 176
9.15 Polyacrylamide with Extremely High Mol Wt by a Solution Process Stream Flows . . . . . . . . . . . . . . . . . . . . . . . 178
9.16 Polyacrylamide with Extremely High Mol Wt by a Solution Process Total Capital Investment . . . . . . . . . . . . . . . . . 181
9.17 Polyacrylamide with Extremely High Mol Wt by a Solution Process Production Costs . . . . . . . . . . . . . . . . . . . . . 182
9.18 Polyacrylamide by an Emulsion Process Major Process Equipment and Utilities Summary . . . . . . . 184
9.19 Polyacrylamide by an Emulsion Process Stream Flows . . . . . . . . . . . . . . . . . . . . . . . 186
9.20 Polyacrylamide by an Emulsion Process Total Capital Investment . . . . . . . . . . . . . . . . . 190
9.21 Polyacrylamide by an Emulsion Process Production Costs . . . . . . . . . . . . . . . . . . . . . . 191
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TABLES
9.22 Polyacrylamide by a Precipitation Process Major Process Equipment and Utilities Summary . . . . . . . 193
9.23 Polyacrylamide by a Precipitation Process Stream Flows . . . . . . . . . . . . . . . . . . . . . . . 195
9.24 Polyacrylamide by a Precipitation Process Total Capital Investment . . . . . . . . . . . . . . . . . 198
9.25 Polyacrylamide by a Precipitation Process Production Costs . . . . . . . . . . . . . . . . . . . . . . 199
10.1 Hydrolysis of Polyacrylamide Patent Surmnary . . . . . . . . . . . . . . . . . . . . . . 203
10.2 Partially Hydrolyzed Polyacrylamide by Simultaneous Polymerization and Hydrolysis Patent Summary . . . . . . . . . . . . . . . . . . . . . . 204
10.3 Methylolation of Polyacrylamide Patent Sunrnary . . . . . . . . . . . . . . . . . . . . . . 206
10.4 Sulfomethylation of Polyacrylamide Patent Summary . . . . . . . . . . . . . . . . . . . . . . 208
10.5 Cationic Polyacrylamide Derivative by Mannich Reaction Patent Summary . . . . . . . . . . . . . . . . . . . . . . 210
10.6 Hoffman Degradation of Polyacrylamide Patent Summary . . . . . . . . . . . . . . . . . . . . . . 212
10.7 Various Cationic Polymers Derived from Polyacrylamides Patent Summary . . . . . . . . . . . . . . . . . . . . . . 213
10.8 Insolubilization of Polyacrylamide Patent Summary . . . . . . . . . . . . . . . . . . . . . . 215
10.9 Grafted Polyacrylamide Patent Summary . . . . . . . . . . . . . . . . . . . . . . 217
10.10 Other Polyacrylamide Derivatives Patent Summary . . . . . . . . . . . . . . . . . . . . . . 218
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TABLES
0
0
10.11 Evaluation of Several Polyacrylamide Derivatives Design Bases and Assumptions . . . . . . . . . . . . . . . . 219
10.12 Anionic Polyacrylamide by Simultaneous Polymerization and Hydrolysis Major Process Equipment and Utilities Summary . . . . . . . . 220
10.13 Anionic Polyacrylamide by Simultaneous Polymerization and Hydrolysis Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . 221
10.14 Anionic Polyacrylamide by Simultaneous Polymerization and Hydrolysis Total Capital Investment . . . . . . . . . . . . . . . . . . 223
10.15 Anionic Polyacrylamide by Simultaneous Polymerization and Hydrolysis Production Costs . . . . . . . . . . . . . . . . . . . . . . 224
10.16 Partially Hydrolyzed Polyacrylamide with Very High Molecular Weight Production Costs . . . . . . . . . . . . . . . . . . . . . . 227
10.17 Partially Hydrolyzed Polyacrylamide with High Molecular Weight Total Capital Investment . . . . . . . . . . . . . . . . . . 232
10.18 Partially Hydrolyzed Polyacrylamide with High Molecular Weight Production Costs . . . . . . . . . . . . . . . . . . . . . . 233
10.19 Mannich Reaction Product of Polyacrylamide Total Capital Investment . . . . . . . . . . . . . . . . . . 235
10.20 Mannich Reaction Product of Polyacrylamide Production Costs . . . . . . . . . . . . . . . . . . . . . . 236
10.21 Sulfomethylated Polyacrylamide with Medium Molecular Weight (Solid) Total Capital Investment . . . . . . . . . . . . . . . . . . 239
10.22 Sulfomethylated Polyacrylamide with Medium Molecular Weight (Solid) Production Costs . . . . . . . . . . . . . . . . . . . . . . 240
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TABLES
10.23 Sulfomethylated Polyacrylamide Produced at Site Total Capital Investment . . . . . . . . . . . . . . . . . . 243
10.24 Sulfomethylated Polyacrylamide Produced at Site Production Costs . . . . . . . . . . . . . . . . . . . . . . 244
11.1 Reactivity Ratios of Monomers in Copolymerization . . . . . 246
11.2 Copolymers of Acrylamide and Acrylic Acid or Acrylate Patent Summary . . . . . . . . . . . . . . . . . . . . . . . 249
11.3 Cationic Polyacrylamide from Acrylamide and (Metha)AcryLic Derivatives Patent Sunrnary . . . . . . . . . . . . . . . . . . . . . . . 251
11.4 Copolymers of Acrylamide and (Metha)Acrylic Esters Patent Summary . . . . . . . . . . . . . . . . . . . . . . . 252
11.5 Copolymers of Acrylamide and Other Unsaturated Amides Patent Sunrnary . . . . . . . . . . . . . . . . . . . . . . . 254
11.6 Copolymers of Acrylamide and Diallyl Compounds Patent Summary . . . . . . . . . . . . . . . . . . . . . . . 258
11.7 Copolymers of Acrylamide and Dibasic Unsaturated Acids Patent Summary . . . . . . . . . . . . . . . . . . . . . . . 259
11.8 Copolymers of Acrylamide and Styrene Patent Summary . . . . . . . . . . . . . . . . . . . . . . . 260
11.9 Copolymers of Acrylamide and N-substituted Lactams Patent Summary . . . . . . . . . . . . . . . . . . . . . . . 261
11.10 Copolymers of Acrylamide and Acrylonitrile Patent Summary . . . . . . . . . . . . . . . . . . . . . . . 262
11.11 Copolymers of Acrylamide and Acrolein Patent Summary . . . . . . . . . . . . . . . . . . . . . . . 263
11.12 Copolymers of Acrylamide and Olefins Patent Summary . . . . . . . . . . . . . . . . . . . . . . . 264
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11.13 Copolymers of Acrylamide and Vinyl Esters Patent Summary . . . . . . . . . . . . . . . . . . . . . . 265
11.14 Copolymers of Acrylamide and Sulfur--Containing Compounds Patent Sunxnary . . . . . . . . . . . . , . . . . . . . . . 266
11.15 Silicon-Containing Polyacrylamide Patent Summary . . . . . . . . . . . . . . . . . . . . . . 267
11.16 Phosphorus-Containing Acrylamide Copolymers Patent Summary . . . . . . . . . . . . . . . . . . . . . . 268
11.17 Acrylamide Grafted on Starch Patent Summary . . . . . . . . . . . . . . . . . . . . . . 269
11.18 Acrylamide Grafted on Polymers Patent Summary . . . . . . . . . . . . . . . . . . . . . . 270
11.19 Miscellaneous Copolymers Containing Acrylamide Patent Summary . . . . . . . . . . . . . . . . . . . . . . 271
11.20 Anionic Copolymers of Acrylamide and Acrylic Acid Design Bases and Assumptions . . . . . . . . . . . . . . . 276
11.21 Anionic Copolymers of Acrylamide and Acrylic Acid Cost Estimates . . . . . . . . . . . . . . . . . . . . . . 277
11.22 Cationic Polyacrylamides Design Bases and Assumptions . . . . . . . . . . . . . . . 279
11.23 Cationic Polyacrylamides Cost Estimates . . . . . . . . . . . . . . . . . . . . . . 282
12.1 Anionic Copolymer Via Polyacrylonitrile Design Bases and Assumptions . . . . . . . . . . . . . . . 286
12.2 Anionic Copolymer Via Polyacrylonitrile Major Process Equipment and Utilities Swmnary . , . . . . . 287
12.3 Anionic Copolymer Via Polyacrylonitrile Stream Flows . . . . . . . . . . . . . . . . . . . . . . . 289
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12.4 Anionic Copolymer Via Polyacrylonitrile Total Capital Investment . . . . . . . . . . . . . . . . . . 291
12.5 Anionic Copolymer Via Polyacrylonitrile Production Costs , . . . , , , . . . . . . . . . . . . . . . 292
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