HEXAMETHYLENE DIAMINE

Transcription

1 Report No 31A HEXAMETHYLENE DIAMINE Supplement A by PARK L MORSE September 1972 A private report by the PROCESS ECONOMICS PROGRAM STANFORD RESEARCH INSTITUTE I I MENLO PARK, CALIFORNIA

2 CONTENTS 1 INTRODUCTION, 1 2 SUMMARY # # General Aspects,,,,,, Technical Aspects,,,, (Du Pont),,, HMD by Dimerization with Sodium Amalgam,, HMD by Electrolytic Dimerization, INDUSTRY STATUS,, 13 4 BMD BY HYDROCYANATION OF BUTADIENE, Chemistry,, Review of Processes,, Conversion of Butadiene to 3-Pentenenitrile Isomerization of 2-Methyl-3-Butenenitrile,, Conversion of 3-Pentenenitrile to Adiponitrile, Catalyst Cycle,,,,,, Hydrogenation and Purification,,, Process Description,,,,, Process Discussion,,,,,,, Cost Estimates,,, HMD BY DIMERIZATION OF PROPYLENE AND ALLYL CHLORIDE,, 57 Chemistry,,,,,, Review of Processes,,,,, 1,5-Hexadiene from Propylene and Ally1 Chloride 1,6-Dibromohexane from 1,5-Hexadiene,, HMD from 1,6-Dibromohexane,, Generation of HBr,, Purification and Hydrogenation Process Description,,,,, Process Discussion,, Base Case (Neutralization with Sodium Methoxide), Replacement of Sodium Methoxide with Caustic Cost Estimates,,,,, * 0 s,

3 CONTENTS 6 HMD BY AMALGAM PROCESS 99 Chemistry 99 Review of Processes 100 ICI Technology 101 UCB Technology 114 Mitsui Toatsu-Toyo Koatsu Technology 118 Solvay and Cie Technology 122 Hydrogenation and Purification 124 Process Description 124 Process Discussion 139 Cost Estimates HMD BY ELECTROLYTIC DIMERIZATION OF ACRYLONITRILE 149 Chemistry 149 Review of Processes 150 Monsanto Technology 150 Asahi Chemical Industry Company Technology 165 UCB Technology 176 BASF Technology 179 Other Companies 179 Purification and Hydrogenation 180 Process Description 180 Process Discussion 188 Cost Estimates OTHER ROUTES TO HEXAMETHYLENEDIAMINE Adipic Acid Route Dichlorobutene Route Chlorination Cynation Isomerization Hydrogenation HMDPlant Diol Route Catalytic Dimerization of Acrylonitrile Ammoxidation of Cyclical Compounds,, Caprolactam Route Copper Halide-Dehydroadiponitrile Route Comparison of Processes,, 199, , 203,,, 203,, * vi

4 CONTENTS 9 PURIFICATION AND HYDROGENATION 217 Purification of Adiponitrile 217 Hydrogenation of Adiponitrile 218 Purification of HMD 218 APPENDIX A DESIGN AND COST BASIS AND DEFINITIONS s 225 APPENDIX B PHYSICAL PROPERTIES AND SPECIFICATIONS,, 229 APPENDIX C HANDLING AND SAFETY, 237 APPENDIX D SUMMARY OF WASTE PRODUCTS, 241 CITED REFERENCES, 245 PATENT REFERENCES BY COMPANY, s 281 vii

5 ILLUSTRATIONS New Du Pont Routes for Conversion of Butadiene to Hexamethylenediamine Effect of Operating Level and Plant Capacity on Production Cost Effect of Operating Level and Plant Capacity on Net Production Cost 95 Effect of Acrylonitrile Concentration on Selectivity 109 Effect of Water on Selectivity 110 ICI Fluidized Bed Reactor for 112 Effect of Protonating Agents on Dimerization in Ammonia 117 Toyo Koatsu Reactor for Effect of Operating Level and Plant Capacity on Net Production Cost 147 Effect of Cell Current Density on Power Consumption 157 Schematic Drawing of Monsanto Electrolytic Cell 159 Exploded View of Monsanto Electrolytic Cell 160 Adiponitrile by Electrolytic Dimerization of Acrylonitrile 185 Effect of Operating Level and Plant Capacity on Production Cost 195 Dichlorobutene Route to Adiponitrile 202 ix

6 TABLES Hexamethylenediamine Processes Cost Comparison 5 Comparison of HMD Processes 7 HMD Plant Capacities, 1972,, 13 Patent Summary 19 Effect of Excess Ligand on Hydrocyanation of Butadiene 25 Effect of trans-spentenenitrile Concentrations on Reaction of HCN with 3- and 4-Pentenenitriles 29 Major Process Equipment and Utilities Summary 36 Stream Flows, 41 Total Capital Investment 51 Production Costs 53 Patent Summary, 59 Condensation of Propylene with Allyl Chloride Under Pressure 61 Condensation of Propylene with Allyl Chloride at One Atmosphere 61 Reaction of 1,5-Hexadiene and Hydrogen Bromide in the Presence of Ultraviolet Light 64 Reaction of 1,5-Hexadiene and HBr in the Presence of Peroxides at Atmospheric Pressure 64 Products from Hydrobromination of 1,5-Hexadiene 65 Products from Amination of Dibromohexane 66 Major Process Equipment and Utilities Summary 74 BMD by Dimerization of Propylene and Ally1 Chloride Stream Flows 79 Xi

7 TABLES Total Capital Investment Production Costs Cost Estimates for Production of 1,5-Hexadiene Patent Summary Toyo Koatsu Dimerization Data for Mitsui Toatsu Treatment of Bicarbonate Cake with Acrylonitrile Mitsui Toatsu Analyses of Calcined and Fired Bicarbonate Major Process Equipment and Utilities Summary HMD by Amalgam, Process Stream Flows Total Capital Investment Production Costs Patent Summary Estimated Characteristics and Performance of a Monsanto-Type Electrolytic Cell Asahi Catholyte Emulsion Resistivity and Solubility of Various Aqueous Quaternary Salts (25'C) Estimated Power for Cells having Various Catholytes UCB Data for Semiindustrial Electrolytic Cell Utilities Summary Stream Flows Total Capital Investment Xii

8 TABLES 710 Production Costs 711 Effect on HMD Costs of Changing Catholyte and Current Density 81 Adiponitrile from Adipic Acid Patent Summary 82 Dichlorobutene Route Patent Summary 83 Catalytic Dimerization Products Patent Summary 84 Ammoxidation of Cyclical Compounds Patent Summary 85 Comparison of Commercial HMD Processes 91 Hydrogenation and Purification of ADN and HMD Patent Summary 92 Comparison of Hydrogenation Catalysts Bl Miscellaneous Physical Properties B2 Vapor Pressure Data B3 Estimated Latent Heats of Vaporization B4 Acrylonitrile Characteristics B5 1,3-Butadiene Specifications B6 Typical Cyclohexane Specification B7 Shell Ally1 Chloride Specifications B8 Typical Published Merchant Adipic Acid Specifications Cl Toxicity Ratings Dl Summary of Waste Products in SRI Design Cases Xiii