PROCESS ECONOMICS PROGRAM

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1 PROCESS ECONOMICS PROGRAM Abstract Process Economics Program Report No. 171 D SRI INTERNATIONAL Menlo Park, California PESTICIDES AND INTERMEDIATES (January 1989) Chlorothalonil, a fungicide, is produced commercially by the chlorination of isophthalonitrile. lsophthalonitrile is produced by the ammoxidation (oxidative ammonolysis) of m- xylene. Methamidophos, an insecticide, is made from O,O-dimethyl phosphorochloroidothioate and ammonia. The O,O-dimethyl phosphorochloridothioate is produced by reacting phosphorus pentasulfide with methanol and chlorinating the resulting acid. The processes for producing each of these pesticides and their respective intermediates are evaluated in this report. Production and capital cost estimates are also presented for each process. In addition, this report includes summaries of patents relevant to both the production of these compounds and the treatment of any by-product streams resulting from their production. Sections on the industry status of these materials and the basic chemistry of the manufacturing processes are presented. PEP 87 L. Elkin C. Michaels

2 a D E 0 on a 0 - E kl Q a Y I E, Report No. 171 D PESTICIDES AND INTERMEDIATES SUPPLEMENT D by LLOYD M. ELKIN and COLLEEN S. MICHAELS January 1989 m A private report by the 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 D/RECTORY OF CHEMlCAL 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 lsophthalonitrile... 2-l Chlorothalonil Phosphorus Pentasulfide O,O-Dimethyl Phosphorochloridothioate (DMPCT) Methamidophos ECONOMIC ASPECTS Chlorothalonil and lsophthalonitrile Methamidophos, DMPCT, and Phosphorous Pentasulfide TECHNICAL ASPECTS lsophthalonitrile Chlorothalonil Phosphorus Pentasulfide DMPCT Methamidophos... 2-l 1 3 INDUSTRY STATUS... 3-l CHLOROTHALONIL... 3-l The Fungicide Market and Consumption Data... 3-l Production and Plant Capacities Prices Raw Materials New Formulations Future Outlook ISOPHTHALONITRILE Consumption Production Prices Raw Materials Licensing METHAMIDOPHOS The Insecticide Market and Consumption Data Production and Plant Capacities Prices Raw Materials... 3-l 0 Future Outlook... 3-l 1... Ill

5 3 INDUSTRY STATUS (Continued) PHOSPHORUS PENTASULFIDE Consumption Data and Product Demand Production and Plant Capacities... 3-l 5 Prices Raw Materials... 3-l 7 Licensing Future Prospects CHEMISTRY... 4-l ISOPHTHALONITRILE... 4-l CHLOROTHALONIL PHOSPHORUS PENTASULFIDE DMPCT METHAMIDOPHOS ISOPHTHALONITRILE BY AMMOXIDATION OF M-XYLENE... 5-l REVIEW OF PATENTS... 5-l PROCESS DESCRIPTION IPN Production/Recovery (Section 100) Purge Gas Treatment (Section 200) Water Treatment/Ammonia Recovery (Section 300) Offsite Storage PROCESS DISCUSSION... 5-l 6 Yield Structure and Reactor Design Product Purity... 5-l 8 Flaking and Bagging Process Building and Warehouse Carbon Dioxide Absorption into Amine Streams Ammonia Absorber Design Ammonia Recovery from the Aqueous Phase Incineration of Plant Wastes Utilities Consumption Materials of Construction COST ESTIMATES Capital Costs Capital Costs Comparison Production Costs iv

6 CONTENTS 6 CHLOROTHALONIL BY CHLORlNATlON OF ISOPHTHALONITRILE... 6-l REVIEW OF PATENTS... 6-l PROCESS DESCRIPTION TIPN Production and Recovery Section (Section 100) Chlorine Recovery and Gas Treatment Section (Section 200) Waste Treatment Section (Section 300) PROCESS DISCUSSION... 6-l 6 Choice of Design Patents Plant Capacity Purity of Feeds Chlorination Reactor Design Catalyst Desublimation TIPN Product Treatment Reaction Gas Scrubber Carbon Tetrachloride Coolant/Absorbent System Chlorine Recovery and Gas Treatment Process Building and Warehouse Materials of Construction.....-; Glass-lined Carbon Steel Nickel InconeMD MonelQD Waste Treatment Direct Chlorination Without Isolation of the IPN Intermediate CARTAL AND PRODUCTION COST Capital Costs Production Costs Profitability Charge for G&A, Sales, and Research Waste Treatment Costs PHOSPHORUS PENTASULFIDE FROM PHOSPHORUS AND SULFUR... 7-l REVIEW OF PROCESSES... 7-l Reactors... 7-l Product Purification... 7-l Phosphorus Purification Phosphorus Pentasulfide Reactivity PROCESS DESCRIPTION PROCESS DISCUSSION

7 CONTENTS 7 PHOSPHORUS PENTASULFIDE FROM PHOSPHORUS AND SULFUR (Continued) Choice of Design Patents... Phosphorus Purification... Semi-continuous Reaction System... Blending/Surge Vessel, V-l Materials of Construction... Phosphorus Pentasulfide Reactivity... Annealing... Waste Treatment... Stream Factor... CAPlTAL AND PRODUCTION COSTS l l O,O-DIMETHYL PHOSPHOROCHLORlDOTHlOATE FROM PHOSPHORUS PENTASULFIDE, METHANOL, AND CHLORINE... REVIEW OF PROCESSES... Principal Route... O,O-Diiethyl Phosphorodithioic Acid (DMPA)... O,O-Dimethyl Phosphorochloridothioate (DMPCT)... O,O-Dimethyl Phosphoroamidothioate... Methamidophos (OS-Dimethyf Phosphoroamidothioate)... PROCESS DESCRlPTlON... PROCESS DISCUSSION... Choice of Design Patents... Diihioic Acid Reactor, R Chlorination Reactors, R-201, R-202, and R-203A&B... Rotary Kiln Incinerator... Waste Treatment, Total Disposal... Sodium Sulfite By-Product Credit... CAPITAL AND PRODUCTION COSTS... 6-l 6-l 6-l OS-DIMETHYL PHOSPHOROAMIDOTHIOATE (METHAMIDOPHOS) FROM O,O-DIMETHYL PHOSPHOROCHLORlDOTHlOATE AND AMMONIUM HYDROXIDE... 9-l PROCESS REVIEW... 9-l PROCESS DESCRIPTION... 9-l PROCESS DISCUSSION Choice of Design Patent... 9-l 1 Product Purity... 9-l 1 vi

8 CONTENTS 9 OS-DIMETHYL PHOSPHOROAMlDOTHlOATE (METHAMIDOPHOS) FROM O,O-DIMETHYL PHOSPHOROCHLORlDOTHlOATE AND AMMONIUM HYDROXIDE (Continued) Diluent in Formulations Safety Waste Treatment CAPITAL AND PRODUCTION COSTS PROFITABIUTY l 1 9-l l APPENDIX A DESIGN AND COST BASIS... A-l APPENDIX B PRODUCT AND RAW MATERIAL SPECIFICATIONS... B-l APPENDIX C PROPERTIES, TOXICITY, AND SAFETY INFORMATlON... C-l APPENDIX D EQUIPMENT SUPPLIERS... D-l APPENDIX E PATENT SUMMARY TABLES... E-l APPENDIX F APPENDIX G APPENDIX H CITED REFERENCES... PATENT REFERENCES BY COMPANY... FLOWSHEETS... F-l G-l H-l vii

9 ILLUSTRATIONS lsophthalonitrile by Ammoxidation of m-xylene Flow Sheet.,.,,,...,... Flow Sheet Phosphorus Pentasulfide from Phosphorus and Sulfur Flow Sheet O,O-Dimethyl Phosphorochloridothioate (DMPCT) from Phosphorus Pentasulfide, Methanol, and Chlorine Flow Sheet,.,.,...,... OS-Dimethyl Phosphoroamidothioate Methamidophos from O,O-Dimethyl Phosphorochloridothioate and Ammonia Flow Sheet H-l H-5 H-6 H-10 H-13 - ix -

10 TABLES lsophthalonitrile and Chlorothalonil Estimated Manufacturing Costs I... Phosphorus Pentasulfide, O,O-Dimethyl Phosphorochloridothioate (DMPCT), and O,S-Dimethyl Phosphoroamidothioate (Methamidophos) Estimated Manufacturing Costs..,...m...,...,... Chlorothalonil Plant Capacities, *... lsophthalonitrile Plant Capacities, High Purity m-xylene Producers and Plant Capacities U.S. Consumption of Insecticides by Chemical Class *... Organophosphorus Insecticides U.S. Consumption of Selected Insecticides Methamidophos Producers and Plant Capacities, Dimethyl Phosphorochloridothloate Producers and Plant Capacities, *... Phosphorus Pentasulfide U.S. Consumption by End Use Phosphorus Pentasulfide Producers and Plant Capacities, *...*.*... Phosphorus Pentasulfide U.S. Production and Export ( ) *... lsophthalonitrile from m-xylene by Ammoxidation Reactor Conditions Patent Summary Production of lsophthalonitrile Patent Summary lsophthalonitrile from m-xylene by Ammoxidation Process Design Features Patent Summary lsophthalonitrile by Ammoxidation of m-xylene Design Bases l 6 3-l 7 E-3 E-l 3 E-l xi

11 TABLES 5.5 lsophthalonitrile from Ammoxidation of m-xylene Major Equipment,...,...,..., lsophthalonitrile from Ammoxidation of m-xylene Utilities Summary lsophthalonitrile by Ammoxidation of m-xylene Stream Flows.,..,..,..,,,,,..., lsophthalonitrile from Ammoxidation of m-xylene Total Capital Investment lsophthalonitrile from Ammoxidation of m-xylene Capital Investment by Section lsophthalonitrile from Ammoxidation of m-xylene Productlon Costs.,.., lsophthalonitrile from Ammoxidation of m-xylene Direct Costs by Section Working Capital Calculation 15 Million lblyr Isophthalonitrile Plant Chlorothalonil from lsophthalonitrile Patent Summary *... E-l 6 Chlorothalonil from Isophthalonitrile, Chlorine Recovery Patent Summary E-20 Design Bases Major Equipment Utilities Summary,,..., Stream Flows Total Capital Investment Capital Investment by Section m Production Costs....I xii

12 6.10 Chlorothalonil by Chlorination of Isophthalonitrile Direct Costs by Section, Working Capital Calculation a Phosphorus Pentasulfide from Phosphorus and Sulfur Patent Summary..,...,...,.,,,,,,.,,... E Phosphorus Pentasulfide from Phosphorus and Sulfur Design Basis Phosphorus Pentasulf ide from Phosphorus and Sulfur Major Equipment Phosphorus Pentasulfide from Phosphorus and Sulfur Utilities Summary..,.,...,.,., Phosphorus Pentasulfide from Phosphorus and Sulfur Stream Flows Phosphorus Pentasulfide from Phosphorus and Sulfur Summary of Reactor Conditions Phosphorus Pentasulfide from Phosphorus and Sulfur Total Capital Investment Phosphorus Pentasulfide from Phosphorus and Sulfur Capital Investment by Section.,, Phosphorus Pentasulfide from Phosphorus and Sulfur Production Costs Phosphorus Pentasulfide from Phosphorus and Sulfur Direct Costs by Section OS-Dimethyl Phosphoroamidothloate and Related Chemical Intermediates Patent Summary *...*... E O,O-Dimethyl Phosphorochlorldothioate from Design Basis O,O-Dimethyl Phosphorochloridothioate from Phosphorus Pentasulf ide, Methanol, and Chlorine Major Equipment *...* O,O-Dimethyl Phosphorochloridothioate from Utilities Summary *... 8-l 4 xiii

13 TABLES O,O-Dimethyl Phosphorochloridothioate (DMPCT) from Stream Flows O,O-Dimethyl Phosphorochloridothioate (DMPCT) from Reactor Conditions, Dithioic Acid Reactor l 8 O,O-Dimethyl Phosphorochloridothioate (DMPCT) from Reactor Conditions, Chlorination Reactors O,O-Dimethyl Phosphorochloridothioate (DMPCT) from Operations in Batch Reactors O,O-Dimethyl Phosphorochloridothioate from Total Capital Investment * O,O-Dlmethyl Phosphorochloridothioate from Capital Investment by Section *m O,O-Dimethyl Phosphorochloridothioate from Production Costs O,O-Dimethyl Phosphorochloridothioate from Direct Costs by Section OS-Dimethyl Phosphoroamidothioate (Methamidophos) from O,O-Dimethyl Phosphorochloridothioate and Ammonium Hydroxide Design Basis,,.,..,...,,.,...,...,... OS-Dimethyl Phosphoroamidothioate from O,O-Dimethyl Phosphorochloridothioate and Ammonia Major Equipment,...,,...,..,...,... OS-Dimethyl Phosphoroamidothioate from O,O-Dlmethyl Phosphorochoridothioate and Ammonia Utilities Summary OS-Dimethyl Phosphoroamidothioate (Methamidophos) from O,O-Dimethyl Phosphorochloridothioate and Ammonia Stream Flows,,,...,...,,,...,, xiv

14 9.10 TABLES OS-Dimethyl Phosphoroamidothioate (Methamidophos) from O,O-Dimethyl Phosphorochloridothioate and Ammonium Hydroxide Reactor Conditions, Amidation Reactor OS-Dimethyl Phosphoroamidothioate (Methamidophos) from O,O-Dimethyl Phosphorochloridothioate and Ammonium Hydroxide Reactor Conditions, lsomerization Reactor OS-Dimethyl Phosphoroamidothioate (Methamidophos) from O,O-Dimethyl Phosphorochloridothioate and Ammonium Hydroxide Operating Schedule of Batch Reactors *... OS-Dimethyl Phosphoroamidothloate from O,O-Dimethyl Phosphorochloridothloate and Ammonia Total Capital Investment OS-Dimethyl Phosphoroamidothioate from O,O-Dimethyl Phosphorochloridothioate and Ammonia Production Costs.,...,,.,...,,.,,...*.. OS-Dimethyl Phosphoroamidothioate (Methamidophos) from O,O-Dimethyl Phosphorochloridothioate and Ammonium Hydroxide Working Capital for 5 Million lblyr (2,300 tlyr) Methamidophos Plant l xv

PROCESS ECONOMICS PROGRAM. Report No by NICK KORENS ROBERT W. VAN SCOY. January private report by the PARK, CALIFORNIA

PROCESS ECONOMICS PROGRAM. Report No by NICK KORENS ROBERT W. VAN SCOY. January private report by the PARK, CALIFORNIA Report No. 110 SYNTHESIS GAS PRODUCTION by NICK KORENS and ROBERT W. VAN SCOY January 1977 A private report by the PROCESS ECONOMICS PROGRAM STANFORD RESEARCH INSTITUTE I MENLO PARK, CALIFORNIA For detailed