POLYBUTYLENE TEREPHTHALATE AND BUTANEDIOL PROCESS ECONOMICS PROGRAM. Report No. 96A. Supplement. by LLOYD M. ELKIN. November 1977

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1 Report No. 96A POLYBUTYLENE TEREPHTHALATE AND BUTANEDIOL Supplement A by LLOYD M. ELKIN and YU-REN CHIN November 1977 A private report by the PROCESS ECONOMICS PROGRAM STANFORD RESEARCH INSTITUTE I I MENLO PARK, CALIFORNIA

2 CONTENTS 1 INTRODUCTION SUMMARY General Aspects... 3 Economic Aspects... 4 Technical Aspects INDUSTRY STATUS Polybutylene Terephthalate ,4-Butanediol CHEMISTRY ,4-Butanediol from Propylene (Allyl Acetate , ,4-Butanediol from Propylene (Allyl Alcohol , ,4-Butanediol from 1,3-Butadiene Polybutylene Terephthalate from Dimethyl Terephthalate and 1,4-Butanediol ,4-BUTANEDIOL FROM PROPYLENE (Allyl Acetate Review of Processes Process Description Process Discussion Choice of Design Patent Polymerization-Grade Propylene Steam Consumption Oxidation to Carbon Dioxide Materials of Construction Cost Estimates Capital Costs Production Costs...., Possible Yield Factor Changes ,4-BUTANEDIOL FROM PROPYLENE (Allyl Alcohol Review of Processes Process Description vii

3 6 1,4-BUTANEDIOL FROM PROPYLENE (Allyl Alcohol (Continued) Process Discussion Hydrolysis Reactor R Extraction Column C Hydrogenation Reactors R Cost Estimates Capital Costs Production Costs ,4-Butanediol from Propylene Oxide ,4-BUTANEDIOL FROM BUTADIENE Review of Processes Process Description Process Discussion Design Patents Hydrolysis Reactor Steam Consumption Hydrogen Purity Tetrahydrofuran Formation Cost Estimates Capital Costs Production Costs Alternative Cost Case ,4-BUTANEDIOL FROM n-butane VIA MALEIC ANHYDRIDE Review of Processes ,4-Butanediol from Maleic Anhydride via y-butyrolactone y-butyrolactone from Maleic Anhydride ,4-Butanediol from y-butyrolactone ,4-Butanediol from Maleic Anhydride by Direct Hydrogenation ,4-Butanediol from Maleic Anhydride via Maleate ,4-Butanediol Purification 130 Process Description Maleic Anhydride Production Butanediol Production Butanediol Purification Process Discussion Cost Estimates Capital Costs Production Costs viii

4 9 1,4-BUTANEDIOL FROM ACETYLENE AND FORMALDEHYDE (1,4-Butynediol, ATMOSPHERIC PRESSURE PROCESS... Review of Processes... Process Description... Process Discussion... Ethynylation Catalyst... Yield Factors... Cost Estimates... Capital Costs... Production Costs... Updated Capital and Production Costs, and Cost Comparison POLYBUTYLENE TEREPHTHALATE... Review of Processes... Manufacture of PBT... Additives... Catalysts... Polymerization Systems... PBT Compounding... Process Description... Polymer Production... Polymer Finishing... Process Discussion... Cost Estimates... Capital Costs... Production Costs... Costs for PBT with High Molecular Weight... Costs for Other Grades... Comparison with the Batch Process OTHER PROCESSES ,4-Butanediol from Acrolein ,4-Butanediol from Butene-l Miscellaneous Processes CITED REFERENCES PATENT REFERENCES BY COMPANY ix

5 ILLUSTRATIONS 2.1 Evaluated Routes for 1,4-Butanediol, Reaction Sequence Flow Sheet Effect of Operating Level and Plant Capacity on Production Cost ,4-Butanediol from Propylene (Allyl Alcohol Flow Sheet..., ,4-Butanediol from Propylene (Allyl Alcohol Effect of Operating Level and Plant Capacity on Production Cost.., Flow Sheet Effect of Operating Level and Plant Capacity on Production Cost Flow Sheet Effect of Operating Level and Plant Capacity on Production Cost (1,4-Butynediol, Atmospheric Pressure Process Flow Sheet (1,4-Butynediol, Atmospheric Effect of Operating Level and Plant Capacity on Production Cost Polybutylene Terephthalate (Self-Extinguishing and Glass-Filled) from Dimethyl Terephthalate and 1,4-Butanediol Flow Sheet..., Xi

6 10.2 Polybutylene Terephthalate (Self-Extinguishing and Glass-Filled) from Dimethyl Terephthalate and 1,4-Butanediol Effect of Operating Level and Plant Capacity on Production Cost Polybutylene Terephthalate (Plain) from Dimethyl Effect of Operating Level and Plant Capacity on Production Cost xii

7 TABLES 2.1 Polybutylene Terephthalate Cost of Manufacturing Various Grades ,4-Butanediol Cost Comparison., ; Plant Capacities for Polybutylene Terephthalate...,. Plant Capacities for 1,4-Butanediol Patent Summary... Major Equipment and Utilities Summary Stream Flows Summary of Reactor Conditions Total Capital Investment Production Costs ,4-Butanediol from Propylene (Allyl Alcohol Major Equipment and Utilities Summary ,4-Butanediol from Propylene (Allyl Alcohol Stream Flows ,4-Butanediol from Propylene (Allyl Alcohol Summary of Reactor Conditions ,4-Butanediol from Propylene (Allyl Alcohol Intermediate Total Capital Investment xiii

8 ,4-Butanediol from Propylene (Allyl Alcohol Production Costs Allyl Alcohol from Propylene Oxide Total Capital Investment : Allyl Alcohol from Propylene Oxide Production Costs ,4-Butanediol from Allyl Alcohol Total Capital Investment ,4-Butanediol from Allyl Alcohol Production Costs Patent Summary Major Equipment and Utilities Summary Stream Flows..., Summary of Reactor Conditions Conditions in Distillation Columns, Second Section Total Capital Investment Production Costs , Alternative Cost Case Total Capital Investment , Alternative Cost Case Production Costs ,4-Butanediol from Maleic Anhydride Patent Summary Operating Conditions for Hydrogenation...., Major Equipment and Utilities Summary Stream Flows Product Distribution for Hydrogenation xiv

9 Total Capital Investment Production Costs (1,4-Butynediol, Atmospheric Patent Summary..., (1,4-Butynediol, Atmospheric Major Equipment and Utilities Summary......,.... (1,4-Butynediol, Atmospheric Stream Flows (1,4-Butynediol, Atmospheric Reactor Conditions for 1,4-Butynediol (1,4-Butynediol, Atmospheric Total Capital Investment (1,4-Butynediol, Atmospheric Production Costs (1,4-Butynediol, Superatmospheric Total Capital Investment (1,4-Butynediol, Superatmospheric Production Costs Polybutylene Terephthalate from Dimethyl Terephthalate (or Terephthalic Acid) and 1,4-Butanediol Patent Summary Polybutylene Terephthalate Compositions Components Used in Compounding Polybutylene Terephthalate Compositions Patent Summary Polybutylene Terephthalate from Dimethyl Summary of Operating Conditions xv

10 10.5 Polybutylene Terephthalate from Dimethyl Major Equipment and Utilities Summary Polybutylene Terephthalate from Dimethyl Stream Flows Polybutylene Terephthalate (Self-Extinguishing and Glass-Filled) from Dimethyl Terephthalate and 1,4-Butanediol Total Capital Investment Polybutylene Terephthalate (Self-Extinguishing and Glass-Filled) from Dimethyl Terephthalate and 1,4-Butanediol Production Costs Polybutylene Terephthalate (Plain) from Dimethyl Total Capital Investment Polybutylene Terephthalate (Plain) from Dimethyl Production Costs Polybutylene Terephthalate from Dimethyl Production Costs for All Four Grades Polybutylene Terephthalate from Dimethyl Comparison of Economics for Batch and Continuous Polymerizations...., ,4-Butanediol from Acrolein Patent Summary xvi

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