TEREPHTHALICACID DIMETHYLTEREPHTHALATE SUPPLEMENT
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1 Report No. 9-A TEREPHTHALICACID DIMETHYLTEREPHTHALATE SUPPLEMENT AND A. contributions by SHIGEYOSHI by LLOYD M. ELKIN TAKAOKA January 1967 A private report by the PROCESS ECONOMICS PROGRAM STANFORD RESEARCH INSTITUTE I MENLO PARK, CALIFORNIA
2 CONTENTS I INTRODUCTION.... II SUMMARY III INDUSTRY STATUS I CHEMISTRY Ammoxidation of p-xylene Terephthalic Acid by Bromine-Promoted Catalytic Air Oxidation ofp-xylene... Terephthalic Acid by Catalytic Oxidation of p-xylene in the Presence of Methyl Ethyl Ketone (MEK) Activator, Terephthalic Acid by Nitric Acid Oxidation of p-xylene.... Terephthalic Acid from Phthalic Anhydride Dimethyl Terephthalate from p-xylene by Successive Oxidations and Esterifications BIS(B-HYDROXYETHYL) TEREPHTHALATE FROM TEREPHTHALONITRILE MADE BY AMMOXIDATION OF P-XYLENE... Review of Processes... Crude Terephthalonitrile Production and Purification... Ammonia Recovery... Bis(2-hydroxyethyl) terephthalate Production and Purification... Process Description... Process Discussion... ;... Crude Terephthalonitrile Production... Ammonia Recovery... Terephthalonitrile Purification... Bis(2-hydroxyethyl) terephthalate Production... Bis(2-hydroxyethyl) terephthalate Purification... Ethylene Glycol Recovery... Capital Cost... Production Cost... Analysis of Effects of Process Changes on Costs... Other Processes for Producing Terephthalonitrile... Ammoxidation of Divinyl Benzene... Reaction of Benzene with Cyanogen... Reaction of p-xylene with NO... Reaction of p-xylene, Sulfur, and Ammonia iii
3 CONTENTS I (continued) Liquid Phase Ammoxidation... Reaction of Benzonitrile with HCN... Intermolecular Rearrangement of Benzonitrile... Reaction of N-alkyl Substituted Aromatic Amines with NO.. Miscellaneous Patents Concerning Terephthalonitrile... GENERAL REIEW OF PROCESSES AND DISCUSSION OF POSSIBLE CHANGES IN THE DESIGNS PRESENTED IN THE ORIGINAL REPORT... Purification of Terephthalic Acid and Dimethyl Terephthalate. Terephthalic Acid by Bromine-Promoted Catalytic Air Oxidation ofp-xylene... Terephthalic Acid by Catalytic Oxidation of p-xylene in the Presence of Methyl Ethyl Ketone (MEK) Activator... Terephthalic Acid from Phthalic Anhydride... Terephthalic Acid by Nitric Acid Oxidation of p-xylene... Dimethyl Terephthalate by Esterification of Terephthalic Acid... Dimethyl Terephthalate by Successive Oxidations and Esterifications APPENDIX A DESIGN AND COST BASIS... APPENDIX B PHYSICALDATA... APPENDIX C HANDLINGANDSAFETY... CITEDREFERENCES... SUPPLEMENTARYREFERENCES.... ERRATATOPEPREPORTNO iv
4 ILLUSTRATIONS Alternate Route, MEX Activator Process Modified Route to TPA via Phthalic Anhydride Terephthalonitrile, apor Pressure versus $
5 TABLES 1 Summary of Process Evaluated (Base Case Design) Plant Capacities--Japan Production of Terephthalonitrile by Ammoxidation of p-xylene Review of Processes Major Process Equipment List Stream Flows Utilities Summary Process Unit and Utilities Investment Total Capital Investment Production Costs Made by Ammoxidation of p-,xylene Effects of Process Changes on Cost Purification of Terephthalic Acid and Dimethyl Terephthalate Review of Processes vii
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