ACRYLAMIDE AND POLYACRYLAMIDE

Transcription

1 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

2 CONTENTS 1 INTRODUCTION......, 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 Vii

3 CONTENTS 6 ACRYLAMIDE BY THE SULFURIC ACID PROCESS Chemistry Review of Processes Process Description Process Discussion Cost Estimate ACRYLAMIDE BY CATALYTIC HYDRATION OF ACRYLONITRILE 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 POLYMERIZATION OF ACRYLAMIDE Mechanism Catalyst for Polymerization Inorganic Compounds Acting Alone Organic Compounds Containing P, B, As,orMetals 111 Organic Compounds Redox Compounds Kinetics Polymerization Processes Bulk Polymerization Solution Polymerization Precipitation Polymerization Suspension Polymerization Emulsion Polymerization Vlll

4 CONTENTS 8 POLYMERIZATION OF ACRYLAMIDE (Continued) Feedstock for Polymerization Polymerization Equipment Removal of Residual Monomer 143 Photo-activated Polymerization' Radiation Polymerization Polymerization with Other Kinds of Initiation EVALUATION OF PROCESSES FOR ACRYLAMIDE POLYMERIZATION A Solution Process for Medium Molecular Weight Polyacrylamide Process Description Process Discussion Cost Estimate A Solution Process for High Molecular Weight Polyacrylamide Process Description Process Discussion Cost Estimate A Solution Process'for'V$ $h'malecular Weight Polyacrylamide Process Descriptio; Process Discussion Cost Estimate A Solution Process'fir Eitremeiy'High Molecular Weight Polyacrylamide Process Description Process Discussion Cost Estimate An Emulsion Procesi for Polyic;yiamide Process Description Process Discussion Cost Estimate A Precipitation Process for Polyacrylamide Process Description Process Discussion Cost Estimate DERIVATIVES OF POLYACRYLAMIDE Review of Products and Processes Partially Hydrolyzed Polyacrylamide Methylolated Polyacrylamide ix

5 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

6 CONTENTS 11 COPOLYMERIZATION OF ACRYLAMIDE (Continued) Copolymerization of Acrylamide and Acrylic Acid in the Presence of Salt Copolymerization of Acrylamide, Methacrylic Acid and Maleic Anhydride A Process for Making a Cationic Polyacrylamide Containing Diallyldimethylammonium Chloride A Process for Making a Cationic Polyacrylamide Containing Quaternized Dimethylaminoethyl Methacrylate A Process for Making a Cationic Copolymer of Aciyiamide and 2-Methyl-5-Vinylpyridine POLYACRYLAMIDE FROM POLYACRYLONITRILE Process Description Process Discussion Cost Estimate OTHER PROCESSES FOR MAKING ACRYLAMIDE AND POLYACRYLAMIDE Acrylamide From AcryloAi;rili through Hydrochloric Acid Hydrolysis From Acrylylchloride From Hydracrylamide or B-Alkoxy-propionamide From 8-Dialkylamino-propionamide From Aldehyde Cyanhydrin From Acrylic Anhydride From Ethylene, Carbon Monoxide and Ammonia By Pyrolysis of Acetoxypropionamide From Alkyl Acrylate Polyacrylamide from Polyacrylate or Polyacrylylchloride APPENDIX A DESIGN AND COST BASES APPENDIX B PHYSICAL PROPERTIES OF ACRYLAMIDE AND ACRYLAMIDE SOLUTIONS APPENDIX C PROPERTIES OF POLYACRYLAMIDE APPENDIX D TOXICITY xi

7 CONTENTS APPENDIX E DISSOLUTION OF POLYACRYLAMIDE APPENDIX F THERMOCHEMICAL DATA CITED REFERENCES PATENT REFERENCES BY COMPANY xii

8 ILLUSTRATIONS 5.1 Manufacture of Acrylamide Comparison of Process Economics Polymerization of Acrylamide Comparison of Process Economics Anionic Polyacrylamide Manufacture (27% Hydrolyzed) Comparison of Process Economics Acrylamide by the Sulfuric Acid Process Acrylamide by the Sulfuric Acid Process Production Cost Acrylamide by Hydration of Acrylonitrile Using Fixed Bed Catalyst , Acrylamide by Hydration of Acrylonitrile Using Fixed Bed Catalyst Production Cost Acrylamide by Hydration of Acrylonitrile Using Suspended Catalyst , Acrylamide by Hydration of Acrylonitrile Using Suspended Catalyst Production Cost Conversion of 50% Solution to Solid Acrylamide Polyacrylamide with Medium Molecular Weight by a Solution Process Polyacrylamide with Medium Molecular Weight by a Solution Process Production Cost Polyacrylamide with High Molecular Weight by a Solution Process xiii

9 ILLUSTRATIONS 9.4 Polyacrylamide with High Molecular Weight by a Solution Process Production Cost, Polyacrylamide with Very High Molecular Weight by a Solution Process.., Polyacrylamide with Very High Molecular Weight by a Solution Process Production Cost Polyacrylamide with Extremely High Molecular Weight by a Solution Process Polyacrylamide with Extremely High Molecular Weight by a Solution Process Production Cost Polyacrylamide by an Emulsion Process Polyacrylamide by an Emulsion Process Production Cost Polyacrylamide by a Precipitation Process Polyacrylamide by a Precipitation Process Production Cost Anionic Polyacrylamide by Simultaneous Polymerization and Hydrolysis Anionic Polyacrylamide by Simultaneous Polymerization and Hydrolysis Production Cost....., xiv

10 ILLUSTRATIONS c.1 Partially Hydrolyzed Polyacrylamide with Very High Molecular Weight Production Cost , Anionic Polyacrylamide with High Molecular Weight Partially Hydrolyzed Polyacrylamide with High Molecular Weight Production Cost Cationic Polyacrylamide by Mannich Reaction Production Cost Sulfomethylated Polyacrylamide Production Cost Anionic Polyacrylamide from Polyacrylonitrile Anionic Polyacrylamide from Polyacrylonitrile Production Cost Viscosity of Polyacrylamide Aqueous Solution xv

11 TABLES Cost of Acrylamide Manufacture Cost of Nonionic Acrylamide Homopolymer Manufacture Cost of Anionic Polyacrylamide Manufacture by After-treatment Cost of Anionic Acrylamide Copolymer Manufacture Cost of Cationic Polyacrylamide Manufacture Producers of Acrylamide..... s Producers of Polyacrylamide Estimated End-Use Pattern for Polyacrylamides Comparison of Processes for Polymerization of Acrylamide Comparison of Processes for Producing Anionic Polyacrylamide Acrylamide by Sulfuric Acid Process--Hydrolysis and Neutralization Patent Summary Acrylamide by Sulfuric Acid Process--Purification and Related Operations Patent Summary Acrylamide by Sulfuric Acid Process Design Bases and Assumptions Acrylamide by Sulfuric Acid Process Major Process Equipment and Utilities Summary xvii

12 TABLES Acrylamide by Sulfuric Acid Process Stream Flows Acrylamide by Sulfuric Acid Process Total Capital Investment Acrylamide by Sulfuric Acid Process Production Costs Acrylamide by Catalytic Hydration of Acrylonitrile Patent Summary Acrylamide by Catalytic Hydration of Acrylonitrile-- Purification, Concentration and Handling Patent Summary Acrylamide by Hydration of Acrylonitrile Using Fixed Bed Catalyst Design Bases and Assumptions , Acrylamide by Hydration of Acrylonitrile Using Fixed Bed Catalyst Major Process Equipment and Utilities Suwtary Acrylamide by Hydration of Acrylonitrile Using Fixed Bed Catalyst Stream Flows Acrylamide by Hydration of Acrylonitrile Using Fixed Bed Catalyst Total Capital Investment... : Acrylamide by Hydration of Acrylonitrile Using Fixed Bed Catalyst Production Costs Acrylonitrile by Hydration of Acrylonitrile Using Suspended Catalyst Design Bases and Assumptions Acrylamide by Hydration of Acrylonitrile Using Suspended Catalyst Stream Flows xviii

13 TABLES 7.10 Acrylamide by Hydration of Acrylonitrile Using Suspended Catalyst Major Process Equipment and Utilities Summary Acrylamide by Hydration of Acrylonitrile Using Suspended Catalyst Total Capital Investment Acrylamide by Hydration of Acrylonitrile Using Suspended Catalyst Production Costs Conversion of 50% Solution to Solid Acrylamide Stream Flows Acrylamide by Hydration of Acrylonitrile Using Suspended Catalyst Comparison of Costs for Producing Solution or Solid Acrylamide Polymerization of Acrylamide in Aqueous Solution Patent Summary Recovery of Polyacrylamide as Solid from an Aqueous Reaction Product Patent Summary Means for Improving the Dissolution of Polyacrylamide Patent Summary Stabilizers for Polyacrylamide Patent Summary Precipitation Processes for Acrylamide Polymerization Patent Summary Polymerization of Acrylamide in Suspension of an Organic No-Solvent Liquid Patent Summary Polymerization of Acrylamide in Oil-in-Water Emulsion Patent Summary xix

14 TABLES 8.8 Polymerization of Acrylamide in Water-in-Oil Emulsion Patent Summary , Equipment for Polymerization Patent Summary Photo-Activated Polymerization of Acrylamide Patent Summary Radiation Polymerization of Acrylamide Patent Sunrnary Processes for the Manufacture of Polyacrylamide Design Bases and Assumptions Polyacrylamide with Medium Mol Wt by a Solution Process s Major Process Equipment and Utilities Summary Polyacrylamide with Medium Mol Wt by a Solution Process Stream Flows Polyacrylamide with Medium Mol Wt by a Solution Process Total Capital Investment Polyacrylamide with Medium Mol Wt by a Solution Process Production Costs Polyacrylamide with High Mol Wt by a Solution Process Major Process Equipment and Utilities Sumnary Polyacrylamide with High Mol Wt by a Solution Process Stream Flows Polyacrylamide with High Mol Wt by a Solution Process Total Capital Investment xx

15 TABLES 9.9 Polyacrylamide with High Mol Wt by a Solution Process Production Costs Polyacrylamide with Very High Mol Wt by a Solution Process Major Process Equipment and Utilities Summary Polyacrylamide with Very High Mol Wt by a Solution Process Stream Flows Polyacrylamide with Very High Mol Wt by a Solution Process Total Capital Investment Polyacrylamide with Very High Mol Wt by a Solution Process Production Costs Polyacrylamide with Extremely High MoL Wt by a Solution Process Major Process Equipment and Utilities Summary Polyacrylamide with Extremely High Mol Wt by a Solution Process Stream Flows Polyacrylamide with Extremely High Mol Wt by a Solution Process Total Capital Investment Polyacrylamide with Extremely High Mol Wt by a Solution Process Production Costs Polyacrylamide by an Emulsion Process Major Process Equipment and Utilities Summary Polyacrylamide by an Emulsion Process Stream Flows Polyacrylamide by an Emulsion Process Total Capital Investment Polyacrylamide by an Emulsion Process Production Costs xxi

16 TABLES 9.22 Polyacrylamide by a Precipitation Process Major Process Equipment and Utilities Summary Polyacrylamide by a Precipitation Process Stream Flows Polyacrylamide by a Precipitation Process Total Capital Investment Polyacrylamide by a Precipitation Process Production Costs Hydrolysis of Polyacrylamide Patent Surmnary Partially Hydrolyzed Polyacrylamide by Simultaneous Polymerization and Hydrolysis Patent Summary Methylolation of Polyacrylamide Patent Sunrnary Sulfomethylation of Polyacrylamide Patent Summary Cationic Polyacrylamide Derivative by Mannich Reaction Patent Summary Hoffman Degradation of Polyacrylamide Patent Summary Various Cationic Polymers Derived from Polyacrylamides Patent Summary Insolubilization of Polyacrylamide Patent Summary Grafted Polyacrylamide Patent Summary Other Polyacrylamide Derivatives Patent Summary xxii

17 TABLES Evaluation of Several Polyacrylamide Derivatives Design Bases and Assumptions Anionic Polyacrylamide by Simultaneous Polymerization and Hydrolysis Major Process Equipment and Utilities Summary Anionic Polyacrylamide by Simultaneous Polymerization and Hydrolysis Stream Flows Anionic Polyacrylamide by Simultaneous Polymerization and Hydrolysis Total Capital Investment Anionic Polyacrylamide by Simultaneous Polymerization and Hydrolysis Production Costs Partially Hydrolyzed Polyacrylamide with Very High Molecular Weight Production Costs Partially Hydrolyzed Polyacrylamide with High Molecular Weight Total Capital Investment Partially Hydrolyzed Polyacrylamide with High Molecular Weight Production Costs Mannich Reaction Product of Polyacrylamide Total Capital Investment Mannich Reaction Product of Polyacrylamide Production Costs Sulfomethylated Polyacrylamide with Medium Molecular Weight (Solid) Total Capital Investment Sulfomethylated Polyacrylamide with Medium Molecular Weight (Solid) Production Costs xx111

18 TABLES Sulfomethylated Polyacrylamide Produced at Site Total Capital Investment Sulfomethylated Polyacrylamide Produced at Site Production Costs Reactivity Ratios of Monomers in Copolymerization Copolymers of Acrylamide and Acrylic Acid or Acrylate Patent Summary Cationic Polyacrylamide from Acrylamide and (Metha)AcryLic Derivatives Patent Sunrnary Copolymers of Acrylamide and (Metha)Acrylic Esters Patent Summary Copolymers of Acrylamide and Other Unsaturated Amides Patent Sunrnary Copolymers of Acrylamide and Diallyl Compounds Patent Summary Copolymers of Acrylamide and Dibasic Unsaturated Acids Patent Summary Copolymers of Acrylamide and Styrene Patent Summary Copolymers of Acrylamide and N-substituted Lactams Patent Summary Copolymers of Acrylamide and Acrylonitrile Patent Summary Copolymers of Acrylamide and Acrolein Patent Summary Copolymers of Acrylamide and Olefins Patent Summary xxiv

19 TABLES Copolymers of Acrylamide and Vinyl Esters Patent Summary Copolymers of Acrylamide and Sulfur--Containing Compounds Patent Sunxnary , Silicon-Containing Polyacrylamide Patent Summary Phosphorus-Containing Acrylamide Copolymers Patent Summary Acrylamide Grafted on Starch Patent Summary Acrylamide Grafted on Polymers Patent Summary Miscellaneous Copolymers Containing Acrylamide Patent Summary Anionic Copolymers of Acrylamide and Acrylic Acid Design Bases and Assumptions Anionic Copolymers of Acrylamide and Acrylic Acid Cost Estimates Cationic Polyacrylamides Design Bases and Assumptions Cationic Polyacrylamides Cost Estimates Anionic Copolymer Via Polyacrylonitrile Design Bases and Assumptions Anionic Copolymer Via Polyacrylonitrile Major Process Equipment and Utilities Swmnary., Anionic Copolymer Via Polyacrylonitrile Stream Flows xxv

20 TABLES 12.4 Anionic Copolymer Via Polyacrylonitrile Total Capital Investment Anionic Copolymer Via Polyacrylonitrile Production Costs,...,,, xxvi