METHACRYLIC ACID METHACRYLIC ESTERS

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1 Report No. 11 A METHACRYLIC ACID METHACRYLIC ESTERS Supplement A by DONALD C. THOMAS Contributions by Brij M. Sood and Leslie A. Carmichael May 1974 A private report by the PROCESS ECONOMICS PROGRAM STANFORD RESEARCH INSTITUTE I I MENLO PARK, CALIFORNIA

2 CONTENTS 1 INTRODUCTION SUMMARY...,... 3 Methyl Methacrylate COMPARISON OF PROCESSES INDUSTRY STATUS METHYL METHACRYLATE VIA ACETONE CYANOHYDRIN Review of Processes Hydrogen Cyanide Production Acetone Cyanohydrin Production Hydrolysis and Esterification Recovery of Methyl Methacrylate Handling and Disposition of Ammonium Bisulfate Process Description Hydrogen Cyanide Production Acetone Cyanohydrin Production Hydrolysis and Esterification Purification Sulfuric Acid Regeneration Process Discussion Waste Treatment Cost Estimates METHYL METHACRYLATE FROM ISOBUTYLENE VIA METHACRYLONITRILE Review of Processes Production Treatment of Ammoxidation By-Products Hydrolysis and Esterification Process Description Production Acetone Cyanohydrin Production Hydrolysis, Esterification, Purification, and Sulfuric Acid Regeneration Process Discussion Cost Estimates Vii

3 CONTENTS 7 METHYL METHACRYLATE FROM ISOBUTYLENE VIA METHACRYLIC ACID Review of Processes... Oxidation of Isobutylene to Methacrolein and... Oxidation of Methacrolein to Recovery and Purification of Esterification of... Process Description... Synthesis... Recovery and Refining... Esterification... Process Discussion... Methacrolein Synthesis... Synthesis... Extraction... Esterification... Data Needed... Possible Areas of Improvement... Cost Estimates... Capital Costs... Production Costs a MISCELLANEOUS PROCESSES FOR METHACRYLIC ACID AND METHYLMETHACRYLATE Methyl Methacrylate from Isobutyraldehyde Oxidative Dehydrogenation Oxyhalodehydrogenation Dehydrogenation with Sulfur from Isobutylene by Oxidation with Nitrogen Tetroxide Methyl Methacrylate from Propylene, Isobutylene, or Propane via Methylacetylene Methylacetylene Production Methyl Methacrylate Production Methyl Methacrylate from Propylene by Oxidative Carbonylation and Methyl Methacrylate by Other Processes HEAVY ESTERS OF METHACRYLIC ACID Viii

4 CONTENTS APPENDIX A DESIGN AND COST BASIS APPENDIX B PHYSICALDATA APPENDIX C PRODUCT SPECIFICATIONS CITED REFERENCES PATENT REFERENCES BY COMPANY IX

5 ILLUSTRATIONS Manufacture of Methyl Methacrylate Comparison of Process Routes Acetone Cyanohydrin from Acetone and Hydrogen Cyanide Equilibrium Conversion of HCN as a Function of Temperature Acetone Cyanohydrin from Acetone and Hydrogen Cyanide Reaction Time as a Function of Temperature Flow Sheet Effect of Plant Capacity on Total Fixed Capital Effect of Plant Capacity and Operating Level on Production Cost Effect of Raw Material Costs on Production Cost Flow Sheet Effect of Plant Capacity on Total Fixed Capital Effect of Plant Capacity, Operating Level, and Isobutylene Cost on Production Cost Flow Sheet Xi

6 ILLUSTRATIONS 7.2 Solvent Extraction of from Water by Pentane Upper and Lower Layer Distribution Coefficient as a Function of Content in the Lower Layer at 20 C Effect of Plant Capacity on Total Fixed Capital Effect of Isobutylene Cost on Production Cost Effect of Plant Capacity and Operating Level on Production Cost Pyrolysis of Propylene xii

7 TABLES Methyl Methacrylate Manufacture Summary of Economics Methyl Methacrylate Manufacture Plant Capacities ,., Bases and Assumptions Major Process Equipment and Utilities Summary Stream Flows Waste Stream Summary Total Capital Investment Production Costs from Isobutylene Patent Summary Bases and Assumptions Major Process Equipment and Utilities Summary Stream Flows Waste Stream Summary Xiii

8 TABLES Total Capital Investment Production Costs Methacrolein by Vapor Phase Oxidation of Isobutylene, Molybdenum-Bismuth Catalyst Patent Summary Methacrolein and by Vapor Phase Oxidation of Isobutylene, Molybdenum-Bismuth Catalyst Patent Summary Methacrolein by Vapor Phase Oxidation of Isobutylene, Molybdenum Catalyst Not Containing Bismuth Patent Summary Methacrolein by Vapor Phase Oxidation of Isobutylene, Catalyst Not Containing Molybdenum Patent Summary Methacrolein and by Vapor Phase Oxidation of Isobutylene, Catalyst Not Containing Molybdenum Patent Summary by Vapor Phase Oxidation of Methacrolein Patent Summary Extraction of from its Aqueous Solution Patent Summary Methyl Methacrylate from Patent Summary _ Bases and Assumptions Major Process Equipment and Utilities Summary xiv

9 TABLES B.l B.2 B.3 c.1 Stream Flows Waste Stream Summary , Total Capital Investment Production Costs Dehydration of o-hydroxyisobutyric Acid or Methyl o-hydroxyisobutyrate Patent Summary Butyl Methacrylate by Liquid Phase Transesterification of Methyl Methacrylate Patent Summary Typical Properties of Methacrylate Monomers Distribution of Between Water and Certain Organic Solvents at Room Temperature Liquid-Liquid Equilibria in the System Methacrylic Acid, Water, and Diethyl Ether at 15'C Shipping Specifications for Methacrylate Monomers xv

PROCESS ECONOMICS PROGRAM

Abstract..-. PROCESS ECONOMICS PROGRAM SRI INTERNATIONAL Mm10 Park, California 9402E Process Economics Program Report No. 11C METHACRYLIC ACID AND METHACRYLIC ESTERS (September 1984) For the last fifteen