ACRYLIC ACID ACRYLIC ESTERS AND PROCESS ECONOMICS PROGRAM. A private report by the. Report No. 6. September 1965

Transcription

1 Report No. 6 ACRYLIC ACID AND ACRYLIC ESTERS by RICHARD G. DENNEY Contributions by Robert E. Johnk September 1965 A private report by the PROCESS ECONOMICS PROGRAM STANFORD RESEARCH INSTITUTE MENLO PARK. CALIFORNIA

2 CONTENTS I INTRODUCTION... II SUMMARY III INDUSTRY STATUS IV CHEMISTRY OF ACRYLIC ACID PRODUCTION V CHEMISTRY OF ACRYLIC ESTERS PRODUCTION VI PROCESSES FOR ACRYLIC ACID MANUFACTURE Acetylene Process Review of Processes.. Process Description.. Process Discussion... Cost Estimates. B-Propiolactone Process. Review of Processes.. Process Description.. Process Discussion... Cost Estimates. Acrylonitrile Process.. Review of Processes.. Process Description.. Process Discussion... Cost Estimates. Propylene Oxidation Process... Review of Processes.. Process Description.. Process Discussion... Cost Estimates. Other Processes. Maleic Acid Process.. Lactic Acid Process.. Ethylene Cyanohydrin Process l,? iii

3 CONTENTS VII PROCESSES FOR LOWER ACRYLIC ESTER MANUFACTURE Acetylene Process.... Review of Processes... Process Description... Process Discussion.... Cost Estimates.... B-Propiolactone Process.. Review of Processes... Process Description... Process Discussion.... Cost Estimates.... Acrylonitrile Process... Review of Processes... Process Description... Process Discussion.... Cost Estimates.... Esterification Process... Review of Processes... Process Description... Process Discussion.... Cost Estimates.... Other Processes.... Saturated Ester Process. Ethylene Cyanohydrin Process VIII PROCESSES FOR HIGHER ACRYLIC ESTER MANUFACTURE Esterification Process.. Review of Processes.. Cost Estimates... Transesterification Process... Review of Processes.. Cost Estimates... IX INTEGRATED PROCESSES iv

4 CONTENTS Appendix A DESIGN AND COST BASIS 273 Appendix B PHYSICAL DATA 275 Appendix C RAW MATERIAL AND PRODUCT SPECIFICATIONS. 279 Appendix D HANDLING AND SAFETY. 283 CITED REFERENCES SUPPLEMENTARY REFERENCES. 302 V

5 ILLUSTRATIONS _.-. --_ 1 Acrylic Acid by High Pressure Catalytic Acetylene Process Side Reactions Effect of Pressure on Reaction Time Acrylic Acid by Acrylonitrile Process (Hypothetical Process) Vapor Phase Propylene Oxidation Effect of Temperature on Propylene Conversion a Vapor Phase Propylene Oxidation Effect of Temperature on Selectivity to Acrylic Acid Vapor Phase Propylene Oxidation Effect of Temperature on per Pass Yield of Acrylic Acid Vapor Phase Propylene Oxidation Effect of Space Velocity on Propylene Conversion Vapor Phase Propylene Oxidation Effect of Conversion on Selectivity to Acrylic Acid Acrylic Acid by Propylene Oxidation......, Lower Acrylic Esters by Stoichiometric-Catalytic Acetylene Process Lower Acrylic Esters Process Acid Hydrolysis of Acrylonitrile to Acrylamide Effect of Reaction Time Lower Acrylic Esters by Acrylonitrile Process vii

6 TABLES Plant Capacities Americas Plant Capacities Asia. Plant Capacities Western Europe Acrylic Acid from Acetylene Summary of Processes Major Process Equipment and Utilities Summary Stream Flows Process Unit and Utilities Investment..,. Total Capital Investment Production Costs Major Process Equipment and Utilities Summary Stream Flows ,.... Process Unit and Utilities Investment.... Total Capital Investment ,. Production Costs Acrylic Acid by Acrylonitrile Process Major Process Equipment and Utilities Summary Acrylic Acid by Acrylonitrile Process Stream Flows Acrylic Acid by Acrylonitrile Process Process Unit and Utilities Investment.... ix

7 - TABLES 18 Acrylic Acid by Acrylonitrile Process Total Capital Investment Acrylic Acid by Acrylonitrile Process Production Costs Acrylic Acid by Acrolein Oxidation Summary of Processes Acrylic Acid by Propylene Oxidation Summary of Processes , Acrylic Acid by Propylene Oxidation Major Process Equipment and Utilities Summary Acrylic Acid by Propylene Oxidation Stream Flows. 24 Acrylic Acid by Propylene Oxidation Process Unit and Utilities Investment Acrylic Acid by Propylene Oxidation Total Capital Investment Acrylic Acid by Propylene Oxidation Production Costs Summary of Processes Lower Acrylic Esters by Catalytic Acetylene Process Summary of Processes , Lower Acrylic Esters by Catalytic Acetylene Process Summary of Union Carbide Processes Major Process Equipment and Utilities Summary Stream Flows. 32 Process Unit and Utilities Investment Total Capital Investment Production Costs..., X

8 TABLES Lower Acrylic Esters by Acrylonitrile Process Process Unit and Utilities Investment Lower Acrylic Esters by Acrylonitrile Process Total Capital Investment Lower Acrylic Esters by Acrylonitrile Process Production Costs Lower Acrylic Esters by Direct Esterification Summary of Processes Major Process Equipment and Utilities Summary.... Stream Flows Process Unit and Utilities Investment Total Capital Investment Production Costs Lower Acrylic Esters from Acrylonitrile Summary of Processes..., Lower Acrylic Esters by Acrylonitrile Process Major Process Equipment and Utilities Summary.,.. Lower Acrylic Esters by Acrylonitrile Process Stream Flows Major Process Equipment and Utilities Summary.... Stream Flows Process Unit and Utilities Investment Total Capital Investment Production Costs xi ,

9 TABLES _ Integrated Acrylic Ester Plant Propylene Oxidation Process Total Capital Investment ,...., Integrated Acrylic Ester Plant Propylene Oxidation Process Allocated Production Costs ,. 259 Integrated Acrylic Ester Plant Catalytic Acetylene Process Total Capital Investment Integrated Acrylic Ester Plant Catalytic Acetylene Process Allocated Production Costs , , 263 Integrated Acrylic Ester Plant Stoichiometric- Catalytic Acetylene Process Total Capital Investment Integrated Acrylic Ester Plant Stoichiometric- Catalytic Acetylene Process Allocated Production Costs xii