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CHDM and Dimethyl Terephthalate

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CHDM and Dimethyl Terephthalate Abstract Process Economics Program Report 213 COPOLYESTERS (May 1995) Polyesters and copolyesters are similar in that they both have a carboxylate ester in the repeating unit and they both are alternating copolymers of a glycol and a diacid. However, copolyesters contain more than one type of diacid and/or glycol. The additional component(s) in the polymer alters the final physical, thermal, and electrical properties of the resulting copolyester. With the proper selection of the monomer, the resulting copolyester can have advantageous properties. Copolyesters containing 1,4-cyclohexanedimethanol (CHDM) are commercially available and used in specialty packaging applications because of their superior strength and clarity. The CHDM imparts good heat stability and physical strength to the resins. This Report reviews manufacturing processes, presents preliminary process designs, and estimates capital and production costs for CHDM (because we have not covered them in previous PEP Reports) and four polymers containing CHDM. Specifically, we evaluate products made from the following dimethyl esters and glycols: · CHDM and dimethyl terephthalate · CHDM, dimethyl terephthalate (80%), and dimethyl isophthalate (20%) · CHDM (66%), ethylene glycol (34%), and dimethyl terephthalate · CHDM (34%), ethylene glycol (66%), and dimethyl terephthalate The first three products are made in a single multipurpose plant. In this Report we also include separate sections on the industry status, chemistry, and blends and additives for polymers containing CHDM. This report will be useful to resin producers interested in either producing CHDM or using it as a monomer to produce polyesters and copolyesters. PEP’93 AEC/LME CONTENTS GLOSSARY xiii 1 INTRODUCTION 1-1 2 SUMMARY 2-1 1,4-CYCLOHEXANEDIMETHANOL (CHDM) 2-1 MULTIPRODUCT POLYMER PLANT 2-2 PCT (Poly[1,4-Cyclohexylenedimethylene Terephthalate]) 2-2 PCTA 2-3 PCTG 2-3 Economics 2-3 PETG (Glycol-Modified Polyethylene Terephthalate) 2-3 3 INDUSTRY STATUS 3-1 1,4-CYCLOHEXANEDIMETHANOL (CHDM) 3-3 POLY(1,4-CYCLOHEXYLENEDIMETHYLENE TEREPHTHALATE) (PCT) 3-3 GLYCOL-MODIFIED POLYETHYLENE TEREPHTHALATE (PETG) 3-4 4 CHEMISTRY 4-1 1,4-CYCLOHEXANEDIMETHANOL (CHDM) 4-1 POLY(1,4-CYCLOHEXYLENEDIMETHYLENE TEREPHTHALATE) (PCT) 4-1 ACID-MODIFIED PCT (PCTA) 4-3 GLYCOL-MODIFIED PCT (PCTG) 4-3 GLYCOL-MODIFIED POLYETHYLENE TEREPHTHALATE (PETG) 4-4 5 1,4-CYCLOHEXANEDIMETHANOL FROM DIMETHYL TEREPHTHALATE AND HYDROGEN 5-1 REVIEW OF PROCESSES 5-1 PROCESS DESCRIPTION 5-2 PROCESS DISCUSSION 5-13 Choice of Design Patent 5-13 Plant Capacity 5-13 Hydrogen Feed Composition 5-13 Hydrogenation Reactors 5-13 - iii - CONTENTS (Continued) 5 1,4-CYCLOHEXANEDIMETHANOL FROM DIMETHYL TEREPHTHALATE AND HYDROGEN (Concluded) PROCESS DISCUSSION (Concluded) Catalyst Life 5-14 Methanator 5-14 Methane Adsorbers 5-14 Pressure Reduction 5-14 Distillation System 5-14 Nitrogen Blankets 5-14 Materials of Construction 5-15 Waste Streams 5-15 Product Form and Purity 5-15 CAPITAL AND PRODUCTION COSTS 5-15 G&A, Sales, and Research Expenses 5-15 Relative Importance of Production Cost Items 5-16 Effect of Plant Capacity on Production Costs 5-16 Refrigeration Costs 5-16 6 POLY(1,4-CYCLOHEXYLENEDIMETHYLENE TEREPHTHALATE) AND TWO OF ITS ACID- OR GLYCOL-MODIFIED COPOLYMERS 6-1 GENERAL 6-1 REVIEW OF PROCESSES 6-1 PROCESS DESCRIPTION 6-3 Production of PCT 6-5 Production of PCTA 6-6 Production of PCTG 6-6 PROCESS DISCUSSION 6-18 Choice of Design Patent 6-18 Feed Composition 6-18 Copolyester Compositions 6-18 Plant Capacity 6-18 Stream Factor/Switching Products 6-19 Transesterification Reactors 6-19 - iv - CONTENTS (Continued) 6 POLY(1,4-CYCLOHEXYLENEDIMETHYLENE TEREPHTHALATE) AND TWO OF ITS ACID- OR GLYCOL-MODIFIED COPOLYMERS (Concluded) PROCESS DISCUSSION (Concluded) Prepolycondensation and Polycondensation Reactors 6-19 Polycondensation Reactor Design 6-20 Side Reactions 6-21 Catalyst/Additive System 6-21 Water Addition 6-21 Diol Recovery/Purification 6-21 Polymer Processing 6-22 Materials of Construction 6-22 Waste Streams 6-22 Catalyst Addition 6-22 Methanol 6-22 CAPITAL AND PRODUCTION COSTS 6-22 Refrigeration Costs 6-23 Effect of Monomer Cost on Production Costs 6-23 Effect of Operating Capacity on Product Value 6-24 7 COPOLYESTERS FROM DIMETHYL TEREPHTHALATE AND MIXED GLYCOLS 7-1 GENERAL 7-1 REVIEW OF PROCESSES 7-1 Process Conditions 7-2 Catalysts and Additives 7-3 PROCESS DESCRIPTION 7-3 PROCESS DISCUSSION 7-16 Choice of Design Patent 7-16 Plant Capacity 7-16 Feed Streams 7-16 Transesterification Reactors 7-16 Prepolycondensation and Polycondensation Reactors 7-17 Polycondensation Reactor Design 7-17 - v - CONTENTS (Concluded) 7 COPOLYESTERS FROM DIMETHYL TEREPHTHALATE AND MIXED GLYCOLS (Concluded) PROCESS DISCUSSION (Concluded) Side Reactions 7-18 Catalyst/Additive System 7-18 EG Distillation Columns 7-18 Water Addition 7-18 Ethylene Glycol Vacuum Jets 7-19 Rundown Bins and Blending Bin 7-19 Polymer Filters 7-19 Materials of Construction 7-19 Waste Streams 7-19 Catalyst Addition 7-19 Methanol 7-19 CAPITAL AND PRODUCTION COSTS 7-19 Effect of Monomer Cost on Product Value 7-20 Effect of Operating Level on Product Value 7-21 8 BLENDS AND ADDITIVES 8-1 BLENDS 8-1 MOLDING COMPOSITIONS AND ADDITIVES 8-6 APPENDIX A: PATENT SUMMARY TABLES A-1 APPENDIX B: DESIGN AND COST BASES B-1 APPENDIX C: PHYSICAL PROPERTIES C-1 APPENDIX D: EQUIPMENT SUPPLIERS D-1 APPENDIX E: CITED REFERENCES E-1 APPENDIX F: PATENT REFERENCES BY COMPANY F-1 APPENDIX G: PROCESS FLOW DIAGRAMS G-1 - vi - ILLUSTRATIONS 5.1 CHDM from DMT By Hydrogenation Process Flow Diagram G-3 6.1 PCT, PCTA, and PCTG from DMT and CHDM (DMI and EG for Acid and Glycol Modification) Process Flow Diagram G-5 6.2 PCT from DMT and CHDM Effect of Raw Material Costs on Product Value 6-33 6.3 PCTA from DMT, DMI, and CHDM Effect of Raw Material Costs on Product Value 6-34 6.4 PCTG from DMT, CHDM, and EG Effect of Raw Material Costs on Product Value 6-35 6.5 PCT from DMT and CHDM Effect of Operating Level and Plant Capacity on Product Value 6-36 6.6 PCTA from DMT, DMI, and CHDM Effect of Operating Level and Plant Capacity on Product Value 6-37 6.7 PCTG from DMT, CHDM, and EG Effect of Operating Level and Plant Capacity on Product Value 6-38 7.1 PETG from DMT, CHDM, and EG Process Flow Diagram G-7 7.2 PETG from DMT, CHDM, and EG Effect of Raw Material Costs on Product Value 7-25 7.3 PETG from DMT, CHDM, and EG Effect of Operating Level and Plant Capacity on Product Value 7-26 8.1 Properties of Polyesters and Copolyesters of TPA with CHDM and/or EG 8-3 8.2 Properties of Some Blends of Copolyesters Containing CHDM 8-5 - vii - - viii - TABLES 2.1 CHDM and Polyesters/Copolyesters Containing CHDM Cost Summary 2-5 3.1 CHDM World Producers 3-1 3.2 PCT, PCTA, and PCTG World Producers 3-2 3.3 PETG World Producers 3-2 3.4 Heat Deflection Temperatures for PBT, PET, and PCT 3-3 5.1 CHDM from DMT Patent Summary A-3 5.2 CHDM from DMT and Hydrogen Design Bases 5-3 5.3 CHDM from DMT and Hydrogen Stream Flows 5-6 5.4 CHDM from DMT and Hydrogen Major Equipment 5-8 5.5 CHDM from DMT and Hydrogen Utilities Summary 5-10 5.6 CHDM from DMT and Hydrogen Summary of Reactor Conditions 5-11 5.7 CHDM from DMT and Hydrogen Waste Streams 5-12 5.8 CHDM from DMT and Hydrogen Total Capital Investment 5-17 5.9 CHDM from DMT and Hydrogen Capital Investment By Section 5-18 5.10 CHDM from DMT and Hydrogen Production Costs 5-19 5.11 CHDM from DMT and Hydrogen Direct Costs By Section 5-21 6.1 Copolyesters Containing CHDM Patent Summary A-6 - ix - TABLES (Continued) 6.2 Copolyesters Containing CHDM Japanese Patent Summary A-17 6.3 PCT and Some of Its Copolyesters Patent Summary Reaction Conditions A-21 6.4 PCT, PCTA, and PCTG from DMT and CHDM (DMI and EG for Acid and Glycol Modification) Design Bases and Assumptions 6-4 6.5 PCT, PCTA, and PCTG from DMT and CHDM (DMI and EG for Acid and Glycol Modification) Summary of Reactor Conditions 6-7 6.6 PCT, PCTA, and PCTG from DMT and CHDM (DMI and EG for Acid and Glycol Modification) Major Equipment 6-8 6.7 PCT from DMT and CHDM Utilities Summary 6-10 6.8 PCTG from DMT, CHDM, and EG Utilities Summary 6-11 6.9 PCT from DMT and CHDM Stream Flows 6-12 6.10 PCTG from DMT, CHDM, and EG Stream Flows 6-14 6.11 PCT from DMT and CHDM Waste Streams 6-16 6.12 PCTG from DMT, CHDM, and EG Waste Streams 6-17 6.13 PCT, PCTA, and PCTG from DMT and CHDM (DMI and EG for Acid and Glycol Modification) Total Capital Investment 6-25 6.14 PCT from DMT and CHDM Production Costs 6-26 6.15 PCTA from DMT, DMI, and CHDM Production Costs 6-28 - x - TABLES (Continued) 6.16 PCTG from DMT, CHDM, and EG Production Costs 6-30 6.17 PCT, PCTA, and PCTG Product Values Relative Importance of Major Cost Categories 6-32 7.1 List of Patent Summaries Relating To PETG 7-2 7.2 PETG from DMT, EG, and CHDM Design Bases and Assumptions 7-4 7.3 PETG from DMT, EG, and CHDM Summary of Transesterification Reactor Conditions 7-7 7.4 PETG from DMT, EG, and CHDM Summary of Prepolycondensation and Polycondensation Reactor Conditions 7-8 7.5 PETG from DMT, EG, and CHDM Major Equipment 7-9 7.6 PETG from DMT, EG, and CHDM Utilities Summary 7-11 7.7 PETG from DMT, EG, and CHDM Stream Flows 7-12 7.8 PETG from DMT, EG, and CHDM Waste Streams 7-15 7.9 PETG from DMT, EG, and CHDM Total Capital Investment 7-22 7.10 PETG from DMT, EG, and CHDM Production Costs 7-23 8.1 Blends and Additives for PCT, PCTA, PCTG, and PETG Patent Summary A-26 8.2 Typical Properties of Polyesters and Copolyesters of TPA with CHDM and/or EG 8-2 8.3 Properties of Blends of Copolyesters with CHDM 8-4 C.1 Selected Properties of CHDM C-4 C.2 Selected Properties of PCT and Selected Competing Products C-5 - xi - TABLES (Concluded) C.3 Selected Properties for PCTA C-8 C.4 Selected Properties for Selected Grades of PCTG C-9 C.5 Selected Properties for PETG C-10 C.6 Eastar® PETG 6763 Copolyester versus Competition C-11 - xii -.
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