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Acrylamide, Polyacrylamide

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Acrylamide, Polyacrylamide 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 MENLO PARK. CALIFORNIA I a CONTENTS 1 INTRODUCTION . , . 2 SUMMARY ............................ 3 Acrylamide .......................... 4 General Aspects ...................... 4 Technical Aspects ..................... 6 Acrylamide Polymers ..................... 7 General Aspects ...................... 7 Technical Aspects ..................... 12 3 INDUSTRY STATUS ....................... 19 Production Capacity ...................... 19 Production and Consumption .................. 19 Commercial Acrylamide 24 Commercial Polyacrylamidls' .................................... 24 4 APPLICATIONS OF ACRYLAMIDE AND POLYACRYLAMIDE ........ 27 As Flocculants ........................ 27 For Waste Water Treatment ................. 27 For Potable Water Treatment ................ 29 For Various Process Industries ............... 29 For the Mining Industry .................. 29 In Oil Production . .. .. ........ 30 Mobility Control Agent'& Wa;e; kodi;g'for Oil Recovery 30 Additive for Oil Well Drilling Fluids .......... 31 Aid in Fracturing, Acidifying, and Other'Operations Relating to Oil Production ................ 32 In the Paper and Pulp Industry ................ 33 Additives for Paper .................... 33 Coating for Paper ..................... 35 Other Uses in the Paper and Pulp Industry ......... 36 In the Textile Industry ................... 36 Coating for Materials Other than Paper and Textiles ..... 38 Construction and Civil Engineering Uses ........... 38 Adhesives .......................... 39 Agricultural Uses ...................... 39 Plastics or Plastics Additives ................ 40 OtherUses .......................... 40 - 5 COMPARISON OF PROCESSES ................... 43 Making Acrylamide ....................... 43 Polymerization Processes ................... 46 Producing Anionic Polyacrylamides .............. 46 Polymerization at Site with Purchase of Polymer ....... 48 0 Vii 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 .............. ....... 73 Review of Pa&n; literature ......... ....... 73 Reactant and Reaction Medium ........ ....... 83 Catalyst ....... 83 Reaction CoAditions.............................. ....... 84 Recovery of Acrylamide .......... ....... 84 An Electrochemical Procesi ......... ....... 85 Process Evaluations .............. ....... 85 A Fixed Bed Catalyst Process ........ ....... 86 Process Description ............ ....... 86 Process Discussion ............ ....... 92 Cost Estimate ............... ....... 92 A Suspended Catalyst Process ........ ....... 96 Process Description ............ ....... 96 Process Discussion ............ ....... 102 Cost Estimate ............... ....... 102 Conversion of 50% Solution to Solid Acrylamide ...... 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 . Vlll CONTENTS 8 POLYMERIZATION OF ACRYLAMIDE (Continued) Feedstock for Polymerization ................ 136 Polymerization Equipment .................. 140 Removal of Residual Monomer 143 Photo-activated Polymerization' .............................. 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 149 Process Description........................................ 149 Process Discussion .................... 154 Cost Estimate ...................... 155 A Solution Process for High Molecular Weight Polyacrylamide ..................... 155 Process Description ................... 155 Process Discussion .................... 162 Cost Estimate .... ......... 163 A Solution Process'for'V$ $h'MAlecular Weight Polyacrylamide .................... 163 Process Descriptio; ................... 163 Process Discussion .................... 171 Cost Estimate . ... ..... ....... 171 A Solution Process'fir Eitremeiy'High Molecular Weight Polyacrylamide ...................... 175 Process Description ................... 175 Process Discussion .................... 180 Cost Estimate .. 180 An Emulsion Procesi for Polyic;yiamide.......................... 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 ix CONTENTS 10 DERIVATIVES OF POLYACRYLAMIDE (Continued) Sulfomethylated Polyacrylamide .............. 207 Mannich Reaction Product ................. 209 Hoffman Degradation Product ............... 209 Other Cationic Polyacrylamides .............. 211 Insoluble Polyacrylamides ................ 214 Grafted Polyacrylamides .................. 216 Other Derivatives .................... 216 Process Evaluations .................... 216 Anionic Polyacrylamide by Simultaneous Polymerization and Hydroysis ........................ 216 Process Description .................. 216 Cost Estimate ...................... 222 A Process for Making Partially Hydrolyzed Polyacrylamide With Very High Molecular Weight ............. 226 Process Description .................. 226 Cost Estimate ...................... 226 A Process for Making Partially Hydrolyzed Polyacrylamide With High Molecular Weight ............... 226 Process Description .................. 229 Cost Estimate ...................... 230 A Process for Making a Mannich Reaction Product of Polyacrylamide 230 Process Descriptio: ..................................... 230 Cost Estimate .... ........ 230 Sulfomethylated Poiyac&iaiide'with Medium Molecular 238 Weight .. ........ .... ............. Sulfomethyiated Polyacrylamide in Dilute Solution 238 11 COPOLYMERIZATION OF ACRYLAMIDE ............... 245 Review of Products and Processes .............. 245 Kinetics ......................... 245 Review of Patents on Copolymers ............. 248 Copolymerization Processes ................ 272 Catalysts for Copolymerization .............. 274 Copolymerization Equipment ................ 274 Recovery of Product ................... 274 Process Evaluations .................... 275 Copolymerization of Acrylamide and Sodium Acrylate in Emulsion ........................ 275 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 . 280 A Process for Making a Cationic Copolymer of Aciyiamide and 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 .... ....... .. 295 From AcryloAi;rili through Hydrochloric Acid Hydrolysis.......... 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 xi CONTENTS APPENDIX E DISSOLUTION OF POLYACRYLAMIDE ............ 309 APPENDIX F THERMOCHEMICAL DATA ................. 311 CITED REFERENCES ........................ 313 PATENTREFERENCES BY COMPANY .................. 359 xii 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
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