Pesticides and Intermediates, Supp. D, January 1989 PROCESS ECONOMICS PROGRAM SRI INTERNATIONAL Abstract Menlo Park, California 94025 Process Economics Program Report No. 171 D 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 mxylene. 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 Pesticides and Intermediates, Supp. D, January 1989 aD E a- 0 0 on Report No. 171D PESTICIDES AND INTERMEDIATES a 0- a- E kl a Q SUPPLEMENT D by LLOYD M. ELKIN and COLLEEN S. MICHAELS Y I E, January 1989 aa m A private report by the PROCESS ECONOMICS PROGRAM Menlo Park, California 94025 Pesticides and Intermediates, Supp. D, January 1989 For detailed marketing data and information, the reader is referred to one of the SRI programs specializing in marketing research. The CHEMICAL ECONOMlCS HANDBOOK Programcovers 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 Pesticides and Intermediates, Supp. D, January 1989 CONTENTS a- aa a l-l 1 INTRODUCTION . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2 SUMMARY ....................................................... GENERAL ASPECTS ............................................... lsophthalonitrile ................................................... 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 2-l 2-l 2-2 2-2 2-3 2-4 2-4 2-4 2-6 2-7 2-7 2-9 2-9 2-10 2-l 1 3 INDUSTRY STATUS ................................................ CHLOROTHALONIL................................................. The Fungicide Market and Consumption Data .......................... 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 .................................................... Future Outlook .................................................... 3-l 3-l 3-l 3-2 3-3 3-3 3-4 3-4 3-4 3-4 3-4 3-6 3-6 3-7 3-7 3-6 3-9 3-9 3-l 0 3-l 1 ... Ill Pesticides and Intermediates, Supp. D, January 1989 3 INDUSTRY STATUS (Continued) PHOSPHORUSPENTASULFIDE ....................................... Consumption Data and Product Demand .............................. Production and Plant Capacities ..................................... Prices ........................................................... Raw Materials .................................................... Licensing ........................................................ Future Prospects .................................................. 4 CHEMISTRY ...................................................... ISOPHTHALONITRILE............................................... CHLOROTHALONIL................................................. PHOSPHORUSPENTASULFIDE ....................................... DMPCT .......................................................... METHAMIDOPHOS ................................................. 5 ISOPHTHALONITRILEBY AMMOXIDATION OF M-XYLENE ................. REVIEW OF PATENTS .............................................. PROCESS DESCRIPTION ............................................ IPN Production/Recovery (Section 100) ............................... Purge Gas Treatment (Section 200) .................................. Water Treatment/Ammonia Recovery (Section 300) ..................... Offsite Storage ................................................... PROCESS DISCUSSION ............................................. Yield Structure and Reactor Design .................................. Product Purity .................................................... 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 3-13 3-14 3-l 5 3-17 3-l 7 3-18 3-18 4-l 4-l 4-4 4-5 4-6 4-8 5-l 5-l 5-2 5-3 5-6 5-9 5-10 5-l 6 5-18 5-l 8 5-18 5-18 5-19 5-19 5-19 5-20 5-20 5-21 5-21 5-21 5-22 5-22 0 a I Pesticides and Intermediates, Supp. D, January 1989 CONTENTS 6 CHLOROTHALONILBY CHLORlNATlONOF ISOPHTHALONITRILE............ REVIEW OF PATENTS .............................................. PROCESS DESCRIPTION ............................................ TIPN Production and Recovery Section (Section 100) ................... Chlorine Recovery and Gas Treatment Section (Section 200) ............. Waste Treatment Section (Section 300) .............................. PROCESS DISCUSSION ............................................. 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 PRODUCTIONCOST ................................... Capital Costs ..................................................... Production Costs .................................................. Profitability ....................................................... Charge for G&A, Sales, and Research ................................ Waste Treatment Costs ............................................ 6-l 6-l 6-2 6-4 6-7 6-6 6-l 6 6-16 6-16 6-17 6-17 6-18 6-16 6-19 6-19 6-19 6-19 6-20 6-21 6-21 6-21 6-21 6-21 6-22 6-22 6-22 6-22 6-23 6-23 6-24 6-24 7 PHOSPHORUSPENTASULFIDEFROM PHOSPHORUSAND SULFUR .......... REVIEW OF PROCESSES ........................................... Reactors ......................................................... Product Purification ................................................ Phosphorus Purification ............................................ Phosphorus Pentasulfide Reactivity ................................... PROCESS DESCRIPTION ............................................ PROCESS DISCUSSION ............................................. 7-l 7-l 7-l 7-l 7-2 7-2 7-2 7-12 .. Pesticides and Intermediates, Supp. D, January 1989 CONTENTS 7 6 9 PHOSPHORUSPENTASULFIDEFROM PHOSPHORUSAND SULFUR (Continued) Choice of Design Patents ........................................... Phosphorus Purification ............................................ Semi-continuous Reaction System ................................... Blending/Surge Vessel, V-l 11 ...................................... Materials of Construction ........................................... Phosphorus Pentasulfide Reactivity ................................... Annealing ........................................................ Waste Treatment .................................................. Stream Factor .................................................... CAPlTAL AND PRODUCTIONCOSTS .................................. 7-12 7-13 7-13 7-14 7-l 4 7-14 7-15 7-15 7-l 6 7-17 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-101 ........................................ Chlorination Reactors, R-201, R-202, and R-203A&B ................... Rotary Kiln Incinerator .............................................. Waste Treatment, Total Disposal .................................... Sodium Sulfite By-Product Credit .................................... CAPITAL AND PRODUCTIONCOSTS .................................. 6-l 6-l 6-l 6-2 6-2 6-4 6-4 6-5 6-21 6-21 6-21 6-22 6-22 6-23 6-23 6-23 OS-DIMETHYL PHOSPHOROAMIDOTHIOATE(METHAMIDOPHOS) FROM O,O-DIMETHYL PHOSPHOROCHLORlDOTHlOATE AND AMMONIUM HYDROXIDE ........................................... PROCESS REVIEW ................................................. PROCESS DESCRIPTION ............................................ PROCESS DISCUSSION ............................................. Choice of Design Patent ........................................... Product Purity .................................................... 9-l 9-l 9-l 9-11 9-l 1 9-l 1 vi Pesticides and Intermediates, Supp. D, January 1989 CONTENTS 9 OS-DIMETHYL PHOSPHOROAMlDOTHlOATE(METHAMIDOPHOS) FROM O,O-DIMETHYL PHOSPHOROCHLORlDOTHlOATE AND AMMONIUM HYDROXIDE (Continued) Diluent in Formulations . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Safety . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Waste Treatment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . CAPITAL AND PRODUCTIONCOSTS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . PROFITABIUTY . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 9-l 1 9-l 1 9-11 9-l 2 9-12 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 EQUIPMENTSUPPLIERS ................................... D-l APPENDIX E PATENT SUMMARY TABLES ................................ E-l APPENDIX F CITED REFERENCES ...................................... F-l APPENDIX G PATENT REFERENCESBY COMPANY ........................ G-l APPENDIX H FLOWSHEETS ........................................... H-l vii Pesticides and Intermediates, Supp. D, January 1989 ILLUSTRATIONS 0 5.1 6.1 7.1 6.1 9.1 lsophthalonitrile by Ammoxidation of m-Xylene Flow Sheet .,.,,,.......,........................................ H-l Chlorothalonil by Chlorination of lsophthalonitrile Flow Sheet . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . H-5 Phosphorus Pentasulfide from Phosphorus and Sulfur Flow Sheet . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . H-6 O,O-Dimethyl Phosphorochloridothioate (DMPCT) from Phosphorus Pentasulfide, Methanol, and Chlorine Flow Sheet ,.,.,....,............................................ H-10 OS-Dimethyl Phosphoroamidothioate Methamidophos from O,O-Dimethyl Phosphorochloridothioate and Ammonia Flow Sheet . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . H-13 - ix - Pesticides and Intermediates, Supp. D, January 1989 TABLES - 2.1 lsophthalonitrile and Chlorothalonil Estimated Manufacturing Costs . . . . . . . . . . . . . . . ..I.................. 2-5 Phosphorus Pentasulfide, O,O-Dimethyl Phosphorochloridothioate (DMPCT) , and O,S-Dimethyl Phosphoroamidothioate (Methamidophos) Estimated Manufacturing Costs ..,......m......,............,...... 2-6 Chlorothalonil Plant Capacities, 1963 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..*....... 3-3 lsophthalonitrile Plant Capacities, 1967 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3-5 High Purity m-Xylene Producers and Plant Capacities . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3-7 3.4 U.S. Consumption of Insecticides by Chemical Class . . . . . . . ..*....... 3-6 3.5 Organophosphorus Insecticides U.S. Consumption of Selected Insecticides . . . . . . . . . . . . . . . . . . . . . . . . . . 3-9 Methamidophos Producers and Plant Capacities, 1963 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3-10 Dimethyl Phosphorochloridothloate Producers and Plant Capacities, 1983 . . . . . . . . . . . . . . . . . . . ..*........ 3-12 Phosphorus Pentasulfide U.S. Consumption by End Use . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3-14 Phosphorus Pentasulfide Producers and Plant Capacities, 1966 . . . . . . . . . . . . ..*...*.*......... 3-l 6 Phosphorus Pentasulfide U.S. Production and Export (1965-1967) . . . . . . . . . . . . . . . . . . . ..*...... 3-l 7 2.2 a- 3.1 3.2 3.3 3.6 3.7 3.6 3.9 3.10 5.1 5.2 5.3 5.4 lsophthalonitrile from m-Xylene by Ammoxidation Reactor Conditions Patent Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . E-3 Production of lsophthalonitrile Patent Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . E-l 3 lsophthalonitrile from m-Xylene by Ammoxidation Process Design Features Patent Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . E-l 6 lsophthalonitrile by Ammoxidation of m-Xylene Design Bases . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5-4 xi Pesticides and Intermediates, Supp. D, January 1989 TABLES 5.5 5.6 5.7 5.6 5.9 5.10 5.11 5.12 6.1 6.2 6.3 6.4 6.5 6.6 6.7 6.8 6.9 lsophthalonitrile from Ammoxidation of m-Xylene Major Equipment ,................,.......,.......,.............. 5-11 lsophthalonitrile from Ammoxidation of m-Xylene Utilities Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5-13 lsophthalonitrile by Ammoxidation of m-Xylene Stream Flows .,..,..,..,,,,,...,................................ 5-14 lsophthalonitrile from Ammoxidation of m-Xylene Total Capital Investment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5-24 lsophthalonitrile from Ammoxidation of m-Xylene Capital Investment by Section . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5-25 lsophthalonitrile from Ammoxidation of m-Xylene Productlon Costs .,..,........................................... 5-26 lsophthalonitrile from Ammoxidation of m-Xylene Direct Costs by Section . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5-26 Working Capital Calculation 15 Million lblyr Isophthalonitrile Plant . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5-29 Chlorothalonil from lsophthalonitrile Patent Summary . . . . . . . . . . . . . . . . . . ..*........................... E-l 6 Chlorothalonil from Isophthalonitrile, Chlorine Recovery Patent Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . E-20 Chlorothalonil by Chlorination of lsophthalonitrile Design Bases . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 6-3 Chlorothalonil by Chlorination of lsophthalonitrile Major Equipment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 6-10 Chlorothalonil by Chlorination of lsophthalonitrile Utilities Summary ,,...........,................................. 6-12 Chlorothalonil by Chlorination of lsophthalonitrile Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 6-13 Chlorothalonil by Chlorination of lsophthalonitrile Total Capital Investment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 6-25 Chlorothalonil by Chlorination of lsophthalonitrile Capital Investment by Section . . . . . . . . . . . . . . . . ..m.................. 6-26 Chlorothalonil by Chlorination of lsophthalonitrile Production Costs . . ..I........................................... 6-27 xii Pesticides and Intermediates, Supp. D, January 1989 Chlorothalonil by Chlorination of Isophthalonitrile Direct Costs by Section ,......................................... 6-29 6.11 Working Capital Calculation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..a 6-30 7.1 Phosphorus Pentasulfide from Phosphorus and Sulfur Patent Summary ..,...,...,.,,,,,,.,,........................... E-21 6.10 7.2 7.3 7.4 7.5 7.6 7.7 7.8 7.9 7.10 6.1 6.2 8.3 6.4 Phosphorus Pentasulfide from Phosphorus and Sulfur Design Basis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7-4 Phosphorus Pentasulfide from Phosphorus and Sulfur Major Equipment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7-7 Phosphorus Pentasulfide from Phosphorus and Sulfur Utilities Summary ..,.,....,.,.,................................. 7-9 Phosphorus Pentasulfide from Phosphorus and Sulfur Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7-10 Phosphorus Pentasulfide from Phosphorus and Sulfur Summary of Reactor Conditions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7-11 Phosphorus Pentasulfide from Phosphorus and Sulfur Total Capital Investment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7-19 Phosphorus Pentasulfide from Phosphorus and Sulfur Capital Investment by Section .,,.................................. 7-20 Phosphorus Pentasulfide from Phosphorus and Sulfur Production Costs . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7-21 Phosphorus Pentasulfide from Phosphorus and Sulfur Direct Costs by Section . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7-23 OS-Dimethyl Phosphoroamidothloate and Related Chemical Intermediates Patent Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..*........*...... E-24 O,O-Dimethyl Phosphorochlorldothioate from Phosphorus Pentasulfide, Methanol, and Chlorine Design Basis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 8-7 O,O-Dimethyl Phosphorochloridothioate from Phosphorus Pentasulfide , Methanol, and Chlorine Major Equipment . . . . . . . . . . . . . . . . . . . . . . . . . . . ..*.....*............ 8-12 O,O-Dimethyl Phosphorochloridothioate from Phosphorus Pentasulfide, Methanol, and Chlorine Utilities Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ...*... 8-l 4 xiii Pesticides and Intermediates, Supp. D, January 1989 TABLES 8.5 6.6 8.7 8.8 8.9 8.10 8.11 6.12 9.1 9.2 9.3 9.4 O,O-Dimethyl Phosphorochloridothioate (DMPCT) from Phosphorus Pentasulfide, Methanol, and Chlorine Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 8-15 O,O-Dimethyl Phosphorochloridothioate (DMPCT) from Phosphorus Pentasulfide, Methanol, and Chlorine Reactor Conditions, Dithioic Acid Reactor . . . . . . . . . . . . . . . . . . . . . . . . . . . 8-l 8 O,O-Dimethyl Phosphorochloridothioate (DMPCT) from Phosphorus Pentasulfide, Methanol, and Chlorine Reactor Conditions, Chlorination Reactors . . . . . . . . . . . . . . . . . . . . . . . . . . . 8-19 O,O-Dimethyl Phosphorochloridothioate (DMPCT) from Phosphorus Pentasulfide, Methanol, and Chlorine Operations in Batch Reactors . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 8-20 O,O-Dimethyl Phosphorochloridothioate from Phosphorus Pentasulfide, Methanol, and Chlorine Total Capital Investment . . . . . . . . . . . . . . . . . . . . . ..*.................. 8-24 O,O-Dlmethyl Phosphorochloridothioate from Phosphorus Pentasulfide, Methanol, and Chlorine Capital Investment by Section . . . . . . . . . . . . . . . . . . . . . . . . . . . ..*m...... 8-25 O,O-Dimethyl Phosphorochloridothioate from Phosphorus Pentasulfide, Methanol, and Chlorine Production Costs . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 8-26 O,O-Dimethyl Phosphorochloridothioate from Phosphorus Pentasulfide, Methanol, and Chlorine Direct Costs by Section . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 8-26 OS-Dimethyl Phosphoroamidothioate (Methamidophos) from O,O-Dimethyl Phosphorochloridothioate and Ammonium Hydroxide Design Basis ,,.,..,.....,,.,...,.....,......................... 9-2 OS-Dimethyl Phosphoroamidothioate from O,O-Dimethyl Phosphorochloridothioate and Ammonia Major Equipment ,....,,....,..,......,.......................... 9-5 OS-Dimethyl Phosphoroamidothioate from O,O-Dlmethyl Phosphorochoridothioate and Ammonia Utilities Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 9-6 OS-Dimethyl Phosphoroamidothioate (Methamidophos) from O,O-Dimethyl Phosphorochloridothioate and Ammonia Stream Flows ,,,....,...,,,....,,............................... 9-7 xiv Pesticides and Intermediates, Supp. D, January 1989 TABLES l 0 9.5 OS-Dimethyl Phosphoroamidothioate (Methamidophos) from O,O-Dimethyl Phosphorochloridothioate and Ammonium Hydroxide Reactor Conditions, Amidation Reactor . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 9.6 9-6 OS-Dimethyl Phosphoroamidothioate (Methamidophos) from O,O-Dimethyl Phosphorochloridothioate and Ammonium Hydroxide Reactor Conditions, lsomerization Reactor . . . . . . . . . . . . . . . . . . . . . . . . . . . 9.7 9-9 OS-Dimethyl Phosphoroamidothioate (Methamidophos) from O,O-Dimethyl Phosphorochloridothioate and Ammonium Hydroxide Operating Schedule of Batch Reactors . . . . . . . . . . . . . ..*.............. 9.8 9-l 0 OS-Dimethyl Phosphoroamidothloate from O,O-Dimethyl Phosphorochloridothloate and Ammonia Total Capital Investment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 9.9 9-14 OS-Dimethyl Phosphoroamidothioate from O,O-Dimethyl Phosphorochloridothioate and Ammonia Production Costs .,.........,,.,.....,,.,,....................*.. 9-15 OS-Dimethyl Phosphoroamidothioate (Methamidophos) from O,O-Dimethyl Phosphorochloridothioate and Ammonium Hydroxide Working Capital for 5 Million lblyr (2,300 tlyr) Methamidophos Plant . . . . . 9-17 9.10 a xv
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