PROCESS ECONOMICS PROGRAM

Transcription

1 PROCESS ECONOMICS PROGRAM SRI INTERNATIONAL Process Economics Abstract Program Report No. 92A Menlo Park, California Flame Retardants (December 1989) This report evaluates the manufacture of two major types of flame retardants: brominated organics and organophosphorus products. In particular the costs of manufacturing decabromodiphenyl oxide, tetrabromobisphenol A, triaryl phosphate esters, alkyl diary1 phosphate esters, and halogenated phosphate esters are reported. In addition to the cost estimates, this report includes summaries of pertinent patents for the products mentioned above. A section on the Industry status is included. We also discuss and summarize the technology of flame retardance mechanisms, various test methods, and the status of the brominated products toxicity issue.

2 Report No. 92A FLAME RETARDANT CHEMICALS SUPPLEMENT A by GREG BOHLMANN E Cl I I m A private report by the December 1989 PROCESS ECONOMICS PROGRAM Menlo Park, California 94025

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

4 CONTENTS 1 INTRODUCTION l-l 2 SUMMARY... 2-l GENERAL ASPECTS... 2-l DECABROMODIPHENYL OXIDE... 2-l TETRABROMOBISPHENOL A TRIARYL PHOSPHATE ESTERS ALKYL DIARYL PHOSPHATE ESTERS HALOGENATED TRIALKYL PHOSPHATE ESTERS TECHNICAL ASPECTS Decabromodiphenyl oxide Tetrabromobisphenol A Triaryl Phosphate Esters Alkyl Diary1 Phosphate Esters ECONOMIC ASPECTS INDUSTRY STATUS... 3-l OVERVIEW... 3-l INDUSTRY PROFILE... 3-l FLAME RETARDANT MANUFACTURERS RAW MATERIALS TECHNOLOGY AND TOXICITY... 4-l FLAME RETARDANCY... 4-l FLAME RETARDANCE MECHANISMS FLAME RETARDANT SYSTEMS Thermoplastics Foams Thermosets TOXICITY TOXICITY TESTS

5 4 TECHNOLOGY AND TOXICITY (Concluded) CONTENTS PRODUCT TOXICITY... REGULATORY ACTIVITIES... PHOSPHATE ESTER TOXICITY... 5 DECAMOMODIPHENYL OXIDE... REVIEW OF PROCESSES... Bromination Reaction... Product Purification... PROCESS DESCRIPTION... PROCESS DISCUSSION... Product Flexibility... Choice of Design Patents... Reaction Conditions... Raw Materials... Hydrogen Bromide By-Product... Wash Water Recycle... Materials of Construction... Waste Treatment... CAPITAL AND PRODUCTION COSTS... Charge for G&A, Sales, and Research... Discussion of Product Value... Effect of Operating Level and Plant Capacity... 8 TETRABROMOBISPHENOL A... REVIEW OF PROCESSES... PROCESS DESCRIPTION l 1 4-l 1 5-l l l 1 5-l l l l 6-l 6-2 PROCESS DISCUSSION Choice of Design Patents Bromination Reactor Product Purity Raw Materials Methyl Bromide By-Product......, l 1 -iv-

6 CONTENTS 8 TETRABROMOBISPHENOL A (Concluded) PROCESS DISCUSSION (Concluded) Hydrogen Bromide By-Product Product Precipitation Materials of Construction CAPlTAL AND PRODUCTION COSTS... 6-l 2 Charge for G&A, Sales, and Research Discussion of Product Value Effect of Operating Level and Plant Capacity TRIARYL PHOSPHATE ESTERS... 7-l REVIEW OF PROCESSES... 7-l PROCESS DESCRIPTION PROCESS DISCUSSION Choice of Design Patents Multiproduct Design Basis Purity of Feeds Alkylation Reaction Phosphorylation Reaction HCI Absorber Product Recovery Materials of Construction Waste Treatment CAPITAL AND PRODUCTION COSTS... 7-l 8 Charge for G&A, Sales, and Research... 7-l 8 Discussion of Product Value... 7-l 9 8 ALKYL DIARYL PHOSPHATE ESTERS... 8-l REVIEW OF PROCESSES... 8-l PROCESS DESCRIPTION PROCESS DISCUSSION Multiproduct Design Basis Choice of Design Patents

7 CONTENTS 8 ALKYL DIARYL PHOSPHATE ESTERS (Concluded) PROCESS DISCUSSION (concluded) Product Recovery Waste Treatment Capital and Production Costs Charge for G&A, Sales, and Research... a-7 Discussion of Product Value HALOGENATED TRIALKYL PHOSPHATE ESTERS ,..., l REVIEW OF PROCESSES... 9-l PROCESS DESCRIPTION PROCESS DISCUSSION... 9-l 2 Multiproduct Design Basis Choice of Design Patents Heats of Reaction Product Recovery... 9-l 2 Waste Treatment CAPITAL AND PRODUCTION COSTS Charge for G&A, Sales, and Research Discussion of Product Value Appendix A: TEST METHODS... A-l TEST METHODS CLASSED BY PHENOMENA... A-3 Ease of Ignition... A-3 Flame Spread... A-3 Heat-Release Rate... A-4 Smoke Obscuration... A-4 Smoke Toxicity... A-4 Test Methods for Classes of Materials... A-4 Building Materials... A-4 Plastics... A-4 Upholstered Furniture and Mattresses... A-5 Electrical Wire, Components, and Products... A-5 -vi-

8 CONTENTS Appendix B: PATENT SUMMARY TABLES **... B-l Appendix C: DESIGN AND COST BASES... C-l DESIGN CONDITIONS... c-3 COST BASES... c-3 Capital Investment... c-3 Production Costs... c-4 Effect of Operating Level on Production Costs... C-5 Appendix D: PHYSICAL PROPERTIES OF SELECTED FLAME RETARDANTS... D-l Appendix E: EQUIPMENT SUPPLIERS..,...*... E-l Appendix F: CITED REFERENCES F-l Appendix G: PATENT REFERENCES BY COMPANY......, G-l Appendix H: PROCESS FLOW DIAGRAMS H-l -vii-

9 5.1 Decabromodiphenyl Oxide from Diphenyl Oxide H-l 5.2 Decabromodiphenyl Oxide from Diphenyl Oxide Effect of Operating Level and Plant Capacity on Production Cost Tetrabromobisphenol A from Bisphenol A H Tetrabromobisphenol A from Bisphenol A Effect of Operating Level and Plant Capacity on Production Cost., Triaryl Phosphate Esters H Triaryl Phosphate Esters Product Value Versus Phenol Price a Alkyl Diary1 Phosphate Esters H m... H-l 1 -ix-

10 TABLES 2.1 Flame Retardants Manufacturer, Chemical Structure. and Raw Materials....,.,.....,.,,,., Summary of Estimated Costs Brominated Organics *...* Summary of Estimated Costs Triaryl Phosphate Esters...., Summary of Estimated Costs Alkyl Diary1 Phosphate Esters * Summary of Estimated Costs......, ,... 2-l U.S., Western European, and Japanese Flame Retardant Consumption.,...I., Estimated U.S. Flame Retardant Consumption Western European Consumption of Flame Retardants Estimated Japanese Consumption of Flame Retardants U.S. Consumption of Flame Retardants by Resin, Major Producers Worldwide Additive Brominated Organic Flame Retardants , Major Producers Worldwide Reactive Brominated Organic Flame Retardants , Major Producers Worldwide Nonhalogenated Phosphate Ester Flame Retardants Major Producers Worldwide Halogenated Phosphate Ester Flame Retardants l Major U.S. Producers Other Phosphorus Organic Flame Retardants l U.S. Bromine Producers U.S. Phosphorus Oxychloride Producers.*..., Decabromodiphenyl Oxide Patent Summary B-3

11 TABLES Decabromodiphenyl Oxide by Bromination of Diphenyl Oxide Design Bases and Reaction Conditions., Decabromodiphenyl Oxide from Diphenyl Oxide Major Equipment I Decabromodiphenyl Oxide from Diphenyl Oxide Utilities Summary,,..., Decabromodiphenyl Oxide from Diphenyl Oxide Stream Flows * Decabromodiphenyl Oxide from Diphenyl Oxide Bromination Batch Cycle Decabromodiphenyl Oxide from Diphenyl Oxide Total Capital Investment Decabromodiphenyl Oxide from Diphenyl Oxide Production Costs * Tetrabromobisphenol A Patent Summary B-12 Tetrabromobisphenol a from Bisphenol A Design Bases and Reaction Conditions , , 6-5 Tetrabromobisphenol A from Bisphenol A Major Equipment, , ,.,...,....., Tetrabromobisphenol A from Bisphenol A Utilities Summary * Tetrabromobisphenol A Stream Flows,.,..,...,.,...,...,,...,..,..,, 6-9 Tetrabromobisphenol A from Bisphenol A Total Capital Investment.,...,..., Tetrabromobisphenol A from Bisphenol A Production Costs ~...~~...~ Triaryl Phosphate Esters Patent Summary ,...m...,... B-18 Mixed Isopropylphenols by Alkylation of Phenol with Propylene Design Bases and Reaction Conditions., ,.,....., t-butylphenol by Alkylation of Phenol With lsobutylene Design Bases and Reaction Conditions Mixed lsopropylphenyl Phosphates by Phosphorylation of Mixed Isopropyl Phenols Design Bases and Reaction Conditions

12 TABLES 7.5 t-butylphenyl Diphenyl Phosphate by Phosphorylation of Mixed t-butylphenol and Phenol Design Bases and Reaction Conditions Synthetic Triaryl Ester from Isopropylphenol and Phenol Stream Flows #...# t-butylphenyl Diphenyl Phosphate Stream Flows #...# Triaryl Phosphate Esters Major Equipment *.m Triaryl Phosphate Esters Utilities Summary.....I Triaryl Phosphate Esters Alkylation Batch Cycle ,..,.,...,...I Triaryl Phosphate Esters Phosphorylation Batch Cycle Triaryl Phosphate Esters Total Capital Investment...* Triaryl Phosphate Esters Capital Investment by Section..,...a..., Triaryl Phosphate Esters Triaryl Ester From Isopropyl Phenol Production Costs # Triaryl Phosphate Esters t-butylphenyl Diphenyl Phosphate Production Costs * Alkyl Diary1 Phosphates Patent Summary *.*...a Alkyl Diary1 and Halogenated Phosphate Esters Major Equipment,..., Alkyl Diary1 Phosphate Esters Utilities Summary n Alkyl Diary1 Phosphate Esters Total Capital Investment Alkyl Diary1 Phosphate Esters: P-Ethylhexyl Diphenyl Phosphate Production Costs l 0 7-l l B XIII-

13 TABLES Alkyl Diary1 Phosphate Esters; lsodecyl Diphenyl Phosphate Production Costs Patent Summary Halogenated Alkyl Phosphate Ester Mixture Patent Summary ~...~ Major Equipment #... Utilities Summary m... Raw Material Yields and Requirements,...., , Halogenated Trialkyl Phosphate Ester Mixture from Phosphorus Trichloride, Neopentyl Glycol, Bromine and Ethylene Oxide Design Bases and Reaction Conditions.,...., , Firemastere 838 Stream Flows,...,... FiremasteP 636 Batch Cycle,...,,...,...,,..,...,... Total Capital Investment #... Tris(Dichloroisopropyl) Phosphate Production Costs Tris(2-Chloroisopropyl) Phosphate Production Costs.,...m...,. Tris(Chloroethyl) Phosphate Production Costs l 1 B-25 B l l Firemaster@ 836 Production Costs *... D-l Decabromodiphenyl Oxide D xiv-

14 TABLES D-2 D-3 D-4 D-5 D-6 D-7 D-6 D-9 D-10 D-11 D-12 D-13 Decabromodiphenyl Oxide--Electrical Grade... Tetrabromobisphenol A... Mixed Isopropyl Phenyl Phosphate... t-butyl Phenyl Diphenyl Phosphate... Trixylenyl Phosphate... Tricresyl Phosphate... P-Ethylhexyl Diphenyl Phosphate... lsodecyl Diphenyl Phosphate... Tri (6,6 -Dichloroisopropyl) Phosphate 1, 3-Dichloro-2-Propanol Phosphate (3: 1)... Tri (6-Dichloroisopropyl) Phosphate 2-Dichloro-2-Propenol Phosphate (3: 1)... Tri (6-Chloroethyl) Phosphate P-Chloroethanol Phosphate (3:l)... Mixed Brominated Chlorinated Alkyl Phosphate D-5 D-6 D-7 D-8 D-9 D-10 D-11 D-12 D-13 D-14 D-15 D-16 -xv-