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Nylon 6,6 Supp. B PROCESS ECONOMICS PROGRAM SRI INTERNATIONAL Abstract Menlo Park, California 94025 Process Economics Program Report No. 54B NYLON 66 (September 1987) This updated report on nylon 66 deals also with its intermediates adipic acid and hexamethylenedlamine. Commercially, adipic acid can be made either from cyclohexane or phenol. Several versions of the cyclohexane process, with variations on catalyst, reactor type, and recovery of waste streams, are evalu- ated. Their economies are generally comparable. The phenol process under most circumstances is less economical than the cyclohexane process. A process under development starting from butadiene is also evaluated. Other processes for making adiplc acid, including one from waste nylon 66 which is used commercially in a small way, and several others of academic interest only, are briefly described and discussed. Hexamethylenediamineis made commercially from adlpic acid, butadiene, or acrylonitrile. The process from adiplc acid is an old one, still surviving because of depreciated equipment and captive adipic acid. The butadiene process can use either the chlorination route or the hydrocyanation route, with the latter being more eco- nomical. The process starting from acrylonitrile involves electro- hydrodimerization. There are three versions: using an undivided cell, using a divided cell and an emulsion, and using a divided cell and a solution. The first-named version is more economical than the other two. All these processes are evaluated in detail In this report. In addition, a process starting from caprolactam, used commercially on a small scale, a process via 1,6-hexanediol once used by Celanese, and several other processes are briefly evaluated or discussed. Nylon 66 is usually produced via the formation of a nylon salt. The manufacture of nylon salt as a 63% solution or in solid form is evaluated. Nylon resins of various forms, standard grade, pigmented grades, compounded grades, and extrusion grade, are evaluated. Both the continuous process and the batch process are considered and discussed. Economics of nylon 66 fibers (carpet staple, carpet yarn, tire cord, textile yarn, hosiery monofilament) are updated from data in previous reports. PEP 85 Y. C. Yen S-Y wu Report No. 5 4 B - 0 NYLON 6 6 SUPPLEMENT 6 YEN-CHEN YEN and SHIH-YUEH WU with contributions by YON-LIEN WU, WEN-FA LIN, CHIH-WEI LEE and REN-BEN CHEN September 1987 A private report by the PROCESS ECONOMICS PROGRAM Menlo Park, California 94025 For detailed marketing data and information, the reader is referred to one of the SRI programs specializing in marketing research. The CHEMICAL ECONOMICS HANDBOOKProgram covers most major chemicals and chemical products produced in the United States and the WORLD PETROCHEMICALS Program covers I I major hydrocarbons and their derivatives on a worldwide basis. In addition, the SRI DIRECTORY OF CHEMICAL PRODUCERS services provide detailed lists of chemical producers by compsny, prod- uct, and plant for the United States and Western Europe. ii Revised Jan. 1988 CONTENTS 1 INTRODUCTION........................ 1 2 SUMMARY .......................... 3 Economic Aspects. ..................... 3 Technical Aspects ..................... 9 Adipic Acid from Cyclohexane--The Base Case ....... 9 Adipic Acid from Cyclohexane--RA by the Hydroperoxide Process .................. 9 Adipic Acid from Cyclohexane--RA by the Boric Acid Process ................... 11 Adipic Acid from Cyclohexane--NitricAcid Oxidation of RAwithReactorCooling ................. 11 Adipic Acid from Phenol ................. 11 Adlpic Acid from Butadiene ................ 11 HMDA from Adiplc Acid .................. 12 BMDA from Butadlene via Chlorination ........... 12 HMDA from Butadlene via Hydrocyanation .......... 13 HMDA from Acrylonitrile via Electrohydrodimerization in Solution ....................... 14 HMDA from Acrylonitrile via Electrohydrodimerization in Emulsion ....................... 15 HMDA from Acrylonitrile via Electrohydrodimerization in an Undivided Cell .................. 15 Nylon Salt Solution from Adlpic Acid and HMDA ...... 16 Solid Nylon Salt ..................... 16 Nylon 66 Resin ...................... 16 Carpet Staple ...................... 17 Carpet Yarn ....................... 17 TireCord ........................ 17 Textile Yarn. ...................... 18 Hosiery Monofilament ................... 18 3 INDUSTRY STATUS ...................... 19 Nylon66 .......................... 19 Hexamethylenediamine .................... 27 AdipicAcid ........................ 27 4 ADIPIC ACID FROM CYCLOHEXARE ................ 33 Chemistry ......................... zi Cyclohexane to KA .................... RAtoAdipicAcid .................... 36 Iii CONTENTS 4 ADIPIC ACID FROM CYCLOHEXANE (Continued) Review of Processes .................... Cyclohexane to KA--Processes ............... Cyclohexane to RA--Reactors ............... 40 Cyclohexane to RA--Product Recovery ........... 41 Cyclohexane to KA--Aqueous Waste Stream Treatment .... 42 RA to Adipic Acid--The Reaction System .......... 43 KA to Adipic Acid--Adipic Acid Recovery ......... 44 ICAto Adipic Acid--Purge Stream Treatment ........ 44 Adipic Adic by One-Step Air Oxidation of Cyclohexane ... 45 Other Processes for Making Adiplc Acid from Cyclohexane .................... Process Description .................... E- Process Discussion ..................... 63 Cost Estimates. ...................... 66 Cyclohexane Oxidation by the Hydroperoxide Process .... 66 Cyclohexane Oxidation by the Boric Acid Process ..... 67 Utilization of Aqueous Waste Stream ........... 68 Oxidation of RA to Adipic Acid Without Large Recycle ... 69 Summary ........... ............. 70 Adipic Acid as a By-product of Caprolactam Production ... 72 5 ADIPIC ACID FROM PHENOL VIA CYCLOHEXANOL .......... 93 Process Description .................... 93 Process Discussion ..................... 100 Cost Estimates. ...................... 100 Adipic Acid from Phenol via Cyclohexanol .......... 102 6 ADIPICACID FROM BUTADIENE ................. 111 Chemistry ......................... 111 Review of Processes .................... 116 Mipic Acid by Carbonylation of Butadiene ........ 116 Catalyst Preparation and Recovery ............ 116 First Hydroesterification ................ 116 Second Hydroesterification ................ 117 Hydrolysis ........................ 117 Purification ....................... 117 An Alternative Second Step ................ 118 Other Processes ..................... 118 iV CONTENTS 6 ADIPIC ACID FROM BUTADIENE (Continued) Process Description .................... 119 Process Discussion ..................... 136 Cost Estimates ....................... 137 7 OTHER PROCESSES FOR MAKING ADIPIC ACID ........... 145 Mipic Acid from Waste Nylon 66 .............. 145 Mipic Acid by Biochemical Processes ............ 145 Mipic Acid from Cyclohexene ................ 146 Mipic Acid by Carbonylation of Diol, Ether, or Lactone . 146 Mlpic Acid by Oxidation of Chlorocyclohexane ....... 146 Mipic Acid from Cyclohexylphenyl Ketone .......... 147 Other Processes ...................... 147 8 HEXAMETHYLENEDIAMINE FROM ADIPIC ACID . 149 Chemistry . ........ 149 Review of Processes . ........ 151 Conversion of Mipic Acid to Adiponitrile ........ 152 Purification of Adiponitrile . ........ 152 Hydrogenation of Adiponitrile to HMDA . ........ 152 Purification of HMDA . ........ 153 Direct Production of HMDA from Mipic Acid ........ 154 Process Description . ........ 154 Process Discussion . ........ 169 Cost Estimates . ........ 170 9 HEXAKETHYLENE DIAMINE FROM BUTADIENE VIA DICHLOROBUTENE AND DICYANOBUTENE ............. 177 Chemistry ......................... 177 Butadiene to Dlchlorobutene ............... 177 Dlchlorobutene to Dicyanobutene ............. 178 Dicyanobutene to Adiponitrile .............. 178 Review of Processes .................... 178 Process Description .................... 179 Process Discussion ..................... 195 Cost Estimates ....................... 195 10 HEXAMETHYLENEDIAMINEFROM BUTADIENE VIA HYDROCYANATION TO ADIPONITRILE .............. 201 Chemistry ......................... 201 Review of Processes .................... 202 V CONTENTS 10 RBXAMETRYLENEDIAMINE FROM BUTADIENE VIA HYDROCYANATION TO ADIPONITRILE (Continued) Process Description . 203 Process Discussion . - . .'. 208 Cost Estimates . , . 208 11 RRXAMRTEIYLENEDIAMINEPROM ACRYLONITRILE VIA ADIPONITRILE BY ELECTRORYDRODIMERIZATION ......... 223 Chemistry ......................... 223 Review of Processes .................... 225 Membrane Cell with Acrylonitrile in Solution ....... 225 Membrane Cell with Acrylonitrile in Aqueous Emulsion ... 226 Undivided Cell ...................... 226 A process for Making RMDA from Acrylonitrile via Adiponitrile by Electrohydrodimerizationin Solution ... 228 Process Description ................... 228 Process Discussion ..................... 242 Cost Estimates. ..................... 242 A Process for Making RMDA via Adiponitrile by Electrohydrodimerizationof Acrylonitrile in Emulsion ... 247 Process Description ................... 247 Process Discussion .................... 257 Cost Estimate ...................... 257 A Process for Making BMDA from Acrylonitrile via Adiponitrile by Electrohydrodimerizationin an Undivided Cell ...................... 262 Process Description ................... 262 Process Discussion .................... 272 Cost Estimates ...................... 272 Comparison of the Processes ................ 273 12 OTRER PROCESSES FOR PREPARATION OF REXAMRTRYLENEDIAMINE
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