- E ISOCYANATES PART II PROCESS ECONOMICS PROGRAM. A private report by the. Menlo Park, California Report No. 1 C SUPPLEMENT YEN-CHEN YEN
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1 - E 0 Report No. 1 C ISOCYANATES PART II SUPPLEMENT C YEN-CHEN YEN July 1979 A private report by the PROCESS ECONOMICS PROGRAM Menlo Park, California 94025
2 CONTENTS 6 ISOCYANATES BY CARBONYLATION... Review of Processes... Manufacture of TDI from DNT by Carbonylation Based on Mitsui Toatsu Patents... Process Description... Process Discussion... Cost Estimates... A Carbonylation Process for Making PMPPI from Nitrobenzene... Process Description... Process Discussion... Cost Estimates... 7 OTHER ISOCYANATES.... Review of Patents... Commercial Isocyanates... Production of Methyl Isocyanate... Process Description... Process Discussion... Cost Estimates PROCESSES FOR PRODUCING ISOCYANATES Phosgenation Carbonylation Cyanate Process Azide Process Dissociation of Urethane Dissociation of Carbamyl Chloride.... Dissociation of Thiourethane Dissociation of Substituted Urea in the Presence of Acid Dissociation of Aminamide Dissociation of Formamide Dissociation of 1,2-Diaxetidinone.... Reactions Similar to Phosgenation.... Using Oxalyl Chloride Using Carbonyl Fluoride Using Trichloromethylchloroformate.. Reaction Between Amine, Carbonyl Sulfide and Chlorothiofonnate iii
3 CONTENTS 8 PROCESSES FOR PRODUCING ISOCYANATES (Continued)... Reaction Between N,N'-Dialkylurea and Diphenylcarbonate... Isocyanates From Other Isocyanates... From Other Organic Isocyanates... From Chlorocarbonylisocyanates... From Chlorosulfonylisocyanates... From Phosphorus Isocyanates... From Iodine Isocyanates... Rearrangement of N-Cbloro-beta-lactam... Rearrangement of N-Halogenazetidonine... From Chlorocyanide... From Hydroxamic Acid... From Isocyanic Acid... Oxidation of Isonitrile... From Silicon Compounds... Reaction Between Substituted Urea and Nitrous Acid... Other Dissociation Reactions... From Imidoyl Chloride... From Phenylchloroformate... From Trichlorocyanuric Acid... From Furoxan... From Chloroalkylidene Carbamic Acid and a Sulfonic Acid. From Chlorosulfonic Acid and Nitrile Chloride... 9 ADDUCTS OF ISOCYANATES... Reactions of Isocyanates on Heating... Reactions with Water... Reactions with a Compound with Active Hydrogen... Reaction with Amines... Reaction with Alcohols... Reaction with Phenols... Reaction with Acids, Ureas, Amides, Urethanes, et al... Dimers... Blocked Isocyanates... Isocyanurates or Isocyanate Trimers... Carbodiimide Isocyanates... Biuret Isocyanates... TDIAdducts... MDI/PMPPI Adducts... Other Adducts... Manufacture of Isocyanate Adducts iv
4 CONTENTS APPENDIX A DESIGN AND COST BASES APPENDIX B TOXICITY AND EXPOSURE STANDARDS CITED REFERENCES PATENT REFERENCES BY COMPANY V
5 ILLUSTRATIONS PMPPI by Carbonylation FlowDiagram PMPPI by Carbonylation Effect of Operating Level and Plant Capacity on Production Cost TDI by Carbonylation Flow Magram TDI by Carbonylation Effect of Operating Level and Plant Capacity on Production Cost Methyl Isocyanate Production Flow Diagram Methyl Isocyanate Production Effect of Operating Level and Plant Capacity on Production Cost Vii
6 TABLES CARBONYLATION OF NITRO COMPOUNDS To ISOCYANATES Summary of Patents to Olin Corporation... Summary of Patents to Sumitomo Chemicals... Summary of Patents to Others... URETHANE BY CARBONYLATION Summary of Patents to Mitsui Toatsu... Summary of Patents to Firms Other than Mitsui Toatsu... Removal of Selenium from a Urethane Solution PatentSwry... Decomposition of Urethanes or Disubstituted Ureas to Isocyanates TDI BY CARBONYLATION Design Bases and Assumptions... StreamFlows... Major Equipment.... Utilities summary... Capital Investment... Production Costs... PMPPI FROM NITROBENZENE BY CARBONYLATION Design Bases and Assumptions... StreamFlows... Major Equipment.... Utilities Summary... Capital Investment... Production Costs... Halogenated Isocyanates by Halogenation Patent Suxmnary ix
7 TABLES Halogenated Isocyanates by Phosgenation of Halogenated Amines Halogenated Isocyanates from Halogenated Compounds by Processes Other than Phosgenation PatentSummary Halogenated Isocyanates by Other Processes PatentSummary Sulfonated Aromatic Isocyanates PatentSummary Sulfonyl Isocyanates Other Sulfur-Containing Isocyanates Phosphorus~ontaining Isocyanates Isocyanates Similar to MD1 and PMPPI and their Precursors 7.10 Other Aromatic Isocyanates 7.11 Xylylene Diisocyanate and Its Diamine and Dinitrile Precursors 7.12 Arylaliphatic Isocyanates 7.13 Methyl Isocyanate and Lower Alkyl Isocyanates PatentSummary Unsaturated Aliphatic Isocyanates 7.15 Other Aliphatic Isocyanates 7.16 Alicyclic Isocyanates X
8 TABLES Heterocyclic Isocyanates Acyl Isocyanates Carbonyl Diisocyanates 269 Cost Features of Some Commercial Isocyanates METHYL ISOCYANATE THROUGH CARBAMYL CHLORIDE DECOMPOSITION Design Bases and Assumptions... StreamFlows... Major Equipment... Utilities Summary... Capital Investment... Production Costs... Phosgenation Process for Making Isocyanates Phosgenation of Isocynates by the Cyanate Process PatentSummary... Preparation of Isocyanate by the Azide Process Other Processes for Preparing Isocyanates TDI Dimer PatentSummary... Blocked Isocyanates Blocked Isocyanates Not Made from Isocyanates Trimers of Isocyanates Carbodiimide Polyisocyanates Xi
9 TABLES 9.6 Biuret Polyisocyanates Adducts of Isocyanates, Mainly TDI Adducts of MD1 or PMPPI Adducts of Aliphatic or Alicyclic Isocyanates Modified Polyisocyanate and Isocyanate Adducts Polyisocyanate Addition Products Useful as Polyols 343 xii
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