TEREPHTHALIC ACID AND DIMETHYL TEREPHTHALATE

Transcription

1 Report No. 9C Supplement TEREPHTHALIC ACID AND DIMETHYL TEREPHTHALATE and FUMIHIKO by LLOYD M. ELKIN YAMAGUCHI August 1976 A private report by the PROCESS ECONOMICS PROGRAM STANFORD RESEARCH INSTITUTE I MENLO PARK, CALIFORNIA

2 For detailed marketing data and information, the reader is referred to one of the SRI programs specializing in marketing research. The CHEMICAL ECONOMICS HANDBOOK Program covers most major chemicals and chemical products produced in the United States and the WORLD HYDROCARBONS Program covers major hydrocarbons and their derivatives on a worldwide basis. In addition, the SRI DIRECTORY OF CHEMICAL PRODUCERS services provide detailed lists of chemical producers by company, product, and plant for the United States and Western Europe. ii

3 CONTENTS 1 INTRODUCTION SUMMARY Industry Status... 3 Description of Processes Evaluated... 4 Capital and Production Costs... 7 Future Developments INDUSTRYSTATUS CHEMISTRY TPA from p-xylene by Bromine-Promoted Catalytic Air Oxidation. 17 DMT from p-xylene by Successive Oxidations. 19 Ammoxidation of p-xylene TPA from Phthalic Anhydride (or Benzoic Acid).. 21 TPA from p-xylene by Catalytic Oxidation in the presence of Activators TPA from p-xylene by Liquid Phase Oxidation in the Presence of Large Amounts of Catalyst REVIEW OF PATENTS TPA from p-xylene by Bromine-Promoted Catalytic Air Oxidation TPA from p-xylene by Catalytic Oxidation in the Presence of Activators... TPA from Phthalic Anhydride or Benzoic Acid... TPA from p-xylene by Nitric Acid Oxidation... TPA Purification... DMT from Crude TPA by Esterification with Methanol... DMT Purification... Stabilizers for Molten DMT... Catalyst. Recovery Other Oxidation Processes......, 25. 3l TEREPHTHALIC ACID FROM p-xylene BY BROMINE-PROMOTED CATALYTIC AIR OXIDATION, CONVENTIONAL PROCESS Updated Capital Costs Updated Production Costs Discussion of Factors Affecting Costs Vii

4 CONTENTS 7 DIMETHYL TEREPHTHALATE FROM p-xylene BY SUCCESSIVE OXIDATIONS AND ESTERIFICATIONS... Review of Patents... Oxidation Step... Esterification Step... Purification of DMT... Treatment of Distillation Residues... Recovery of Oxidation Catalyst... Process Description... Process Discussion... Material Balance... Oxidation Reactor Design... Oxygen Consumption... Esterification Reaction Time... Heat of Esterification... Methanol Distillation... DMT Distillation Columns... Column Design... Air Cooled Heat Exchangers... Two-Stage Crystallization... Balance on Generated and Consumed Low Pressure Steam... Stabilizers for Molten DMT... Utility Consumptions... Cost Estimates Capital Costs... Production Costs TEREPHTHALIC ACID FROM p-xylene; COPRODUCTION WITH DIMETHYL TEREPHTHALATE... Introduction 97 Process Description Process Discussion Material Balance Reactions and Physical Changes Occuring in 102 the Heat Treatment Vessels 102 Purification Method Cost Estimates Capital Costs Production Costs Cost Comparison Viii

5 CONTENTS 9 DIMETHYL TEREPHTHALATE FROM CRUDE TEREPHTHALIC ACID BY ESTERIFICATION WITH METHANOL Updated Capital Costs Updated Production Costs Discussion of Factors Affecting Costs TEREPHTHALIC ACID FROM p-xylene BY BROMINE-PROMOTED CATALYTIC AIR OXIDATION, MODIFIED PROCESS Process Description Process Discussion, Purification Section, Batch versus Continuous Operation Process Discussion, Catalyst Recovery Section Batch versus Continuous Operation 127 Chemical Treatment Reactor R-301.,: Water Type Carbon Dioxide Contamination Cost Estimates Capital Costs 128 Production Costs' TEREPHTHALIC ACID FROM p-xylene BY AMMOXIDATION AND HYDROLYSIS. 133 Review of Patents Process Description Process Discussion By-Products in Ammoxidation of p-xylene Overall Yield Utilities Comparison Materials of Construction Cost Estimates Capital Costs 163 Production Costs' CITED REFERENCES PATENT REFERENCES BY COMPANY ix

6 ILLUSTRATIONS 6.1 Terephthalic Acid from p-xylene by Bromine-Promoted Catalytic Air Oxidation, Conventional Process Production Costs Dimethyl from p-xylene by Successive Oxidations Flow Sheet , Dimethyl from p-xylene by Successive Oxidations Production Cost , Terephthalic Acid from p-xylene; Coproduction with Dimethyl Flow Sheet W Terephthalic Acid from p-xylene; Coproduction with Dimethyl Production Cost Dimethyl from Crude Terephthalic Acid by Esterification with Methanol Production Cost Terephthalic Acid from p-xylene by Bromine-Promoted Catalytic Flow Sheet Terephthalic Acid from p-xylene by Bromine-Promoted Catalytic Production Cost Terephthalic Acid from p-xylene by Ammoxidation and Hydrolysis Flow Sheet Terephthalic Acid from p-xylene by Ammoxidation and Hydrolysis Production Cost Xi

7 TABLES Summary of Capital and Production Costs Dimethyl and Terephthalic Acid Plant Capacities in the Americas Dimethyl and Terephthalic Acid Plant Capacities in Western Europe Dimethyl and Terephthalic Acid Plant Capacities in the Eastern Bloc Countries Dimethyl and Terephthalic Acid Plant Capacities in the Middle and Far East Terephthalic Acid from p-xylene by Bromine-Promoted Catalytic Air Oxidation Terephthalic Acid from p-xylene by Catalytic Oxidation in the Presence of Activators Terephthalic Acid from Phthalic Anhydride or Benzoic Acid Terephthalic Acid from p-xylene by Nitric Acid Oxidation Terephthalic Acid Purification Dimethyl from Crude Terephthalic Acid by Esterification with Methanol Dimethyl Purification Stabilizers for Molten Dimethyl Patent Summary ~~~o...~~~~. Catalyst Recovery Other Oxidation Processes xiii

8 TABLES Terephthalic Acid from p-xylene by Bromine-Promoted Catalytic Air Oxidation, Conventional Process Total Capital Investment Terephthalic Acid from p-xylene by Bromine-Promoted Catalytic Air Oxidation, Conventional Process Production Costs Dimethyl from p-xylene by Successive Oxidations Patent Summary: Oxidation Reaction Dimethyl from p-xylene by Successive Oxidations Major Equipment and Utilities Summary Dimethyl from p-xylene by Successive Oxidations Stream Flows Dimethyl from p-xylene by Successive Oxidations Sumnary of Reactor Conditions Dimethyl from p-xylene by Successive Oxidations Total Capital Investment Dimethyl from p-xylene by Successive Oxidations Production Costs Terephthalic Acid from p-xylene; Coproduction with Dimethyl Major Equipment and Utilities Summary Terephthalic Acid from p-xylene; Coproduction with Dimethyl Stream Flows......, Terephthalic Acid from p-xylene; Coproduction with Dimethyl Total Capital Investment xiv

9 TABLES 8.4 Terephthalic Acid from p-xylene; Coproduction with Dimethyl Production Costs Dimethyl from Crude Terephthalic Acid by Esterification with Methanol Total Capital Investment Dimethyl from Crude Terephthalic Acid by Esterification with Methanol Production Costs Terephthalic Acid from p-xylene by Bromine-Promoted Catalytic Major Equipment and Utilities Summary Terephthalic Acid from p-xylene by Bromine-Promoted Catalytic Stream Flows Terephthalic Acid from p-xylene by Bromine-Promoted Catalytic Total Capital Investment Terephthalic Acid from p-xylene by Bromine-Promoted Catalytic Production Costs Terephthalonitrile from p-xylene by Ammoxidation, Reactor Conditions 11.2 Terephthalonitrile from p-xylene by Ammoxidation, Process Design Features 11.3 Terephthalic Acid from Terephthalonitrile 11.4 Terephthalic Acid from p-xylene by Ammoxidation and Hydrolysis Major Equipment and Utilities Summary Terephthalic Acid from p-xylene by Ammoxidation and Hydrolysis Stream Flows xv

10 TABLES 11.6 Terephthalic Acid from p-xylene by Ammoxidation and Hydrolysis Summary of Reactor Conditions Terephthalic Acid from p-xylene by Ammoxidation and Hydrolysis Total Capital Investment Terephthalic Acid by Ammoxidation and Hydrolysis Production Costs xvi