PROCESS ECONOMICS PROGRAM - Markit · PROCESS ECONOMICS PROGRAM Abstract SRI INTERNATIONAL Menlo...
Transcript of PROCESS ECONOMICS PROGRAM - Markit · PROCESS ECONOMICS PROGRAM Abstract SRI INTERNATIONAL Menlo...
PROCESS ECONOMICS
PROGRAM
Abstract
SRI INTERNATIONAL
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.
Hexamethylenediamine is 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
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Report No. 5 4 B
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 HANDBOOK Program 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.
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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--Nitric Acid 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 ......................... Cyclohexane to KA ....................
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RAtoAdipicAcid .................... 36
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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 ICA to 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
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CONTENTS
6 ADIPIC ACID FROM BUTADIENE (Continued)
Process Description .................... 119 Process Discussion ..................... 136 Cost Estimates ....................... 137
7 OTHER PROCESSES FOR MAKING ADIPIC ACID ...........
Mipic Acid from Waste Nylon 66 .............. Mipic Acid by Biochemical Processes ............ Mipic Acid from Cyclohexene ................ Mipic Acid by Carbonylation of Diol, Ether, or Lactone . . Mlpic Acid by Oxidation of Chlorocyclohexane ....... Mipic Acid from Cyclohexylphenyl Ketone .......... Other Processes ......................
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 .............
Chemistry ......................... Butadiene to Dlchlorobutene ............... Dlchlorobutene to Dicyanobutene ............. Dicyanobutene to Adiponitrile ..............
Review of Processes .................... Process Description .................... Process Discussion ..................... Cost Estimates .......................
10 HEXAMETHYLENEDIAMINE FROM BUTADIENE VIA HYDROCYANATION TO ADIPONITRILE ..............
Chemistry ......................... Review of Processes ....................
145
145 145 146 146 146 147 147
177
177 177 178 178 178 179 195 195
201
201 202
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CONTENTS
10 RBXAMETRYLENEDIAMINE FROM BUTADIENE VIA HYDROCYANATION TO ADIPONITRILE (Continued)
Process Description . . . . . . . . . . . . . . . . . . . . 203 Process Discussion . . . - . . . . . . .' . . . . . . . . . . 208 Cost Estimates . . . . . , . . . . . . . . . . . . . . . . . 208
11 RRXAMRTEIYLENEDIAMINE PROM 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 Electrohydrodimerization in Solution ... 228 Process Description ................... 228
Process Discussion ..................... 242 Cost Estimates. ..................... 242
A Process for Making RMDA via Adiponitrile by Electrohydrodimerization of Acrylonitrile in Emulsion ... 247 Process Description ................... 247 Process Discussion .................... 257 Cost Estimate ...................... 257
A Process for Making BMDA from Acrylonitrile via Adiponitrile by Electrohydrodimerization in 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 . . 279
Processes for Making Adiponitrile ............. 279 Amalgam Process Starting with Acrylonitrile ....... 279 Catalytic Dimerization of Acrylonitrile ......... 280 Other Processes for Producing Adiponitrile ........ ' 280
Processes for Making UMDA from Other Raw Materials ..... 280
HMDA from Caprolactam .................. 280 BHDA from Cyclohexane via 1,6-Rexanediol (the Diol Process) ................... 283
RMDA from Propylene and Ally1 Chloride .......... 285 Other Processes for Producing BMDA ........... 287
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13 NTLONSALT ......................... 289
Chemistry ......................... 289 Review of Processes .................... 289
A Process for Producing Nylon Salt Solution ........ 290 Process Description ................... 290 Process Discussion .................... 296 Cost Estimates. ..................... 296
A Process for Producing Solid Nylon Salt .......... 300 Process Description ................... 300 Process Discussion .................... 305 Cost Estimates ...................... 305
14 NTLONRESINS ........................ 309
Chemistry ......................... 309 Review of Processes .................... 309 Process Description .................... 311 Process Discussion ..................... 321 Cost Estimates ....................... 324 Batch Process for Producing Nylon 66 Resin ......... 333 Nylon Resin from Waste Fiber ................ 334
15 NYLON 66 FIBER....................... 343
APPENDIX A PRYSICALDATA . . . . . . . . . . . . . . . . . . . 367
PATENT SUMMARYTABLES. . . . . . . . . . . . . . . . . . . . . . 379
CITEDREFERENCES . . . . . . . . . . . . . . . . . . . . . . . . 481
PATENT REFERENCES. . . . . . . . . . . . . . . . . . . . . . . . 517
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TABLES
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2.1 Adipic Acid (Polymer Grade) Economics .......... 4
2.2 Hexamethylenediamine Economics ............. 6
2.3 Nylon Salt Economics .................. 7
2.4 Nylon Resins (Standard Grade) Economics ......... 8
2.5 Nylon Fiber Economics .................. 10
3.1 Nylon 66 Producers in the United States (1986) . . . . . . . . . . . . . . . . . . . . . . . . . 20
Nylon 66 Producers in Western Europe (1986) . . . . . . . . . . . . . . . . . . . . . . . . . 21
Nylon 66 Producers in Countries Outside of United States and Western Europe (1986) . . . . . . . . . . . . . . . . . . . . . . . . . 22
Consumption of Nylon 66 (1983) . . . . . . . . . . . . . . . . . . . . . . . . . 23
U.S. Nylon Fiber Demand by Market Segment (1983) . . . . . . . . . . . . . . . . . . . . . . . . . 25
U.S. Nylon 66 Fiber Demand by Market Segment . . . . . . 26
U.S. Consumption of Nylon 66 Resins by End-Use (1984) . . . . . . . . . . . . . . . . . . . . . . . . . 26
World Hexamethylenediamine Producers (1986) . . , . . . . . . . . . . . . . . . . . . . . . . 29
Applications of Adipic Acid . . . . . . . . . . . . . . . 30
World Adipic Acid Producers (1986) . . . . . . . . . . . . . . . . . . . . . . . . . 31
3.2
3.3
3.4
3.5
3.6
3.7
3.8
3.9
3.10
4.1
4.2
4.3
Cyclohexanol/Cyclohexanone from Cyclohexane by Catalytic Oxidation Patent Summary . . . . . . . . . . . . . . . . . . . . . 381
Cyclohexanol/Cyclohexanone from Cyclohexane by Hydroperoxide Process Patent Summary . . . . . . . . . . . . . . . . . . . . . 384
Cyclohexanol/Cyclohexanone from Cyclohexane by Boric Acid Process Patent Summary . . . . . . . . . . . . . . . . . . . . . 387
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TABLES
4.4 Treatment of Reaction Product from Cyclohexane Oxidation Patent Summary . . . . . . . . . . . . . . . . . . . . . 389
4.5 Treatment of the Aqueous Waste Stream from Oxidation of Cyclohexane Patent Summary . . . . . . . . . . . . . . . . . . . . . 391
4.6 Adipic Acid from Cyclohexanol/Cyclohexanone by Nitric Acid Oxidation
Patent Summary . . . . . . . . . . . . . . . . . . . . . 396
4.7 Recovery of Adipic Acid from Cyclohexanol/Cyclohexanone Nitric Acid Oxidation
Patent Summary . . . . . . . . . . . . . . . . . . . . . 400
4.8 Treatment of Purge Stream from Adipic Acid Recovery Patent Summary . . . . . . . . . . . . . . . . . . . . . 401
4.9 Purification of Adipic Acid Patent Summary . . . . . . . . . . . . . . . . . . . . . 407
4.10 Adipic Acid from Cyclohexane by One-Step Molecular Oxygen Oxidation Patent Summary . . . . . . . . . . . . . . . . . . . . . 408
4.11 Adipic Acid from Cyclohexanol/Cyclohexanone by Air Oxidation Patent Summary . . . . . . . . . . . . . . . . . . . . . 414
4.12 Cyclohexane to Adipic Acid by Direct Nitric Acid or Nitric Oxides Oxidation
PatentSummary . . . . . . . . . . . . . . . . . . . . . 420
4.13 Adipic Acid by Oxidation with Ozone, Hydrogen Peroxide, Sulfuric Acid, or Other Compound
Patent Summary . . . . . . . . . . . . . . . . . . . . . 422
4.14 Adipic Acid from Cyclohexane Design Bases and Assumptions . . . . . . . . . . . . . . 47
4.15 Adipic Acid from Cyclohexane Stream Flows . . . . . . . . . . . . . . . . . . . . . . 54
4.16 Adipic Acid from Cyclohexane Major Equipment . . . . . . . . . . . . . . . . . . . . . 58
4.17 Adipic Acid from Cyclohexane Utilities Summary . . . . . . . . . . . . . . . . . . . . 62
4.18 Adipic Acid from Cyclohexane Waste Streams . . . . . . . . . . . . . . . . . . . . . . 65
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4.19
4.20
4.21
4.22
4.23
4.24
4.25
4.26
4.27
4.28
4.29
5.1
5.2
5.3
5.4
5.5
5.6
TABLES
Adipic Acid from Cyclohexane Total Capital Investment . . . . . . . . . . . . . . . .
Adipic Acid from Cyclohexane Production Costs . . . . . . . . . . . . . . . . . . . .
Mipic Acid from Cyclohexane by Hydroperoxide Process Major Equipment. . . . . . . . . . . . . . . . . . . . .
Adipic Acid from Cyclohexane by Hydroperoxide Process Production Costs . . . . . . . . . . . . . . . . . . . .
Adipic Acid from Cyclohexane by Boric Acid Process Major Equipment. . . . . . . . . . . . . . . . . . . . .
Adipic Acid from Cyclohexane by Boric Acid Process Production Costs . . . . . . . . . . . . . . . . . . . .
Adipic Acid from Cyclohexane with Recovery of Acids from Aqueous Waste
Major Equipment . . . . . . . . . . . . . . . . . . . . .
Adipic Acid from Cyclohexane with Recovery of Acids from Aqueous Waste Production Costs . . . . . . . . . . . . . . . . . . . .
Adipic Acid from Cyclohexane, Low Recycle Process Major Equipment . . . . . . . . . . . . . . . . . . . . .
Adipic Acid from Cyclohexane, Low Recycle Process Production Costs . . . . . . . . . . . . . . . . . . . .
Adipic Acid from Cyclohexane SummaryofCosts . . . . . . . . . . . . . . . . . . . .
Cyclohexanol by Phenol Hydrogenation Patent Summary . . . . . . . . . . . . . . . . . . . . .
Cyclohexanol from Phenol by Hydrogenation Design gases and Assumptions l l . . . . . . l l . l l l
Cyclohexanol from Phenol by Hydrogenation Stream Flows . . . . . . . . . . . . . . . . . . . l . .
Cyclohexanol from Phenol by Hydrogenation Major Equipment . . . . . . . . . l . . . l l . . . l l l
Cyclohexanol from Phenol by Hydrogenation Utilities Summary . . . . . . . l l . l l . . . l l l l l
Cyclohexanol from Phenol by Hydrogenation Total Capital Investment l l l l l l l l l l l l l l l l
73
76
78
79
81
83
85
86
88
89
91
424
96
97
98
99
1042
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TABLES
5.7
5.8
5.9
6.1
6.2
6.3
6.4
6.5
6.6
6.7
7.1
7.2
7.3
7.4
7.5
7.6
8.1
Cyclohexanol from Phenol by Hydrogenation Production Costs . . . . . . . . . . . . . . . . . . . . 105
Adipic Acid from Phenol via Cyclohexanol Total Capital Investment . . . . . . . . . . . . . . . . 107
Mipic Acid from Phenol via cyclohexanol Production Costs . . . . . . . . . . . . . . . . . . . . 108
Mipic Acid from Butadiene PatentSummary . . . . . . . . . . . . . . . . . . . . . 425
Mipic Acid from Butadiene Design Bases and Assumptions l . . . . . . . . . . . . . 120
Mipic Acid from Butadiene Stream Flows . . . . . . . . . . . . . . . . . . . . . . 127
Adipic Acid from Butadiene Major Equipment. . . . . . . . . . . . . . . . . . . . . 131
Mipic Acid from Butadiene Utilitiee Summary . . . . . . . . . . . . . . . . . . . . 135
Mipic Acid from Butadiene Total Capital Investment . . . . . . . . . . . . . . . . 139
Mipic Acid from Butadiene Production Costs . . . . . . . . . . . . . . . . . . . . 142
Mipic Acid by Biochemical Processes PatentSummary . . . . . . . . . . . . . . . . . . . . . 428
Mipic Acid from Cyclohexene Patent Summary . . . . . . . . . . . . . . . . . . . . . 429
Mipic Acid by Carbonylation of Ether PatentSummary . . . . . . . . . . . . . . . . . . . . . 431
Mipic Acid by Oxidation of Chlorocyclohexane PatentSummary . . . . . . . . . . . . . . . . . . . . . 432
Mipic Acid from Cyclohexylphenyl Ketone Patent Summary . . . . . . . . . . . . . . . . . . . . . 433
Miscellaneous Processes for Making Mipic Acid PatentSummary . . . . . . . . . . . . . . . . . . . . . 434
Miponitrile from Mipic Acid Patent Summary . . . . . . . . . . . . . . . . . . . . . 435
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8.2 Purification of Adiponitrile PatentSummary . . . . . . . . . . . . . . . . . . . . . 438
8.3 Hexamethylenediamine from Miponitrile by Hydrogenation Patent Summary . . . . . . . . . . . . . . . . . . . . . 441
8.4 Purification of Hexamethylenediamine PatentSummary . . . . . . . . . . . . . . . . . . . . . 444
8.5 Hexamethylenediamine Directly from Mipic Acid PatentSummary . . . . . . . . . . . . . . . . . . . . . 446
8.6 Hexamethylenediamine from Mipic Acid Design Bases and Assumptions . . . . . . . . . . . . . . 155
8.7 Hexamethylenediamine from Mipic Acid StreamFlows . . . . . . . . . . . . . . . . . . . . . . 160
8.8 Hexamethylenediamine from Mipic Acid Major Equipment. . . . . . . . . . . . . . . . . . . . . 164
8.9 Hwxamethylenediamine from Mipic Acid Utilities Summary . . . . . . . . . . . . . . . . . . . . 168
8.10 Hexamethylenediamine from Mipic Acid Total Capital Investment . . . . . . . . . . . . . . . . 172
8.11 Hexamethylenediamine from Mipic Acid Production Costs . . . . . . . . . . . . . . . . . . . . 174
9.1 Miponitrile from Butadiene via Dichlorobutene PatentSummary . . . . . . . . . . . . . . . . . . . . . 447
9.2 Hexamethylenediamine from Butadiene via Dichlorobutene and Dicyanobutene Design Bases and Aesumptions . . . . . . . . . . . . . . 180
9.3 Hexamethylenediamine from Butadiene via Dichlorobutene and Dicyanobutene Stream Flows . . . . . . . . . . . . . . . . . . . . . . 186
9.4 Hexamethylenediamine from Butadiene via Dichlorobutene and Dicyanobutene
Major Equipment. . . . . . . . . . . . . . . l . . . . . 190
9.5 Hexamethylenediamine from Bu.tadiene via Dichlorobutene and Dicyanobutene Utilities Summary . . . . . . . . . . . . . . . . . . . . 194
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TABLES
9.6 Hexamethylenediamine from Butadiene via Dichlorobutene and Dicyanobutene Total Capital Investment . . . . . . . . . . . . . l . . 196
9.7 Hexamethylenediamine from Butadiene via Dichlorobutene and Dicyanobutene Production Costs . . . . . . . . . . . . . . . . . . . . 198
10.1 Miponitrile from Butadiene by Hydrocyanation Summary of Du Pont Patents . . . . . . . . . . . . . . . 450
10.2 Miponitrile from Butadiene by Hydrocyanation Summary of Patents to Assignees Other than Du Pont . . . 452
10.3 Hexamethylenediamine from Butadiene via Eydrocyanation to Miponitrile Design Bases and Assumptions . . . . . . . . . . . . . . 209
10.4 Hexamethylenediamine from Butadiene via Hydrocyanation to Miponitrile StreamFlows . . . . . . . . . . . . . . . . . . . . . . 210
10.5 Hexamethylenediamine from Butadiene via Hydrocyanation to Adiponitrile MajorEquipment... . . . . . . . . . . . . . . . . . . 212
10.6 Hexamethylenediamine from Butadiene via Hydrocyanation to Miponitrile Utilities Summary . . . . . . . . . . . . . . . . . . . . 216
10.7 Hexamethylenediamine from Butadiene via Hydrocyanation to Miponitrile Total Capital Investment . . . . . . . . . . . . . . . . 217
10.8 Hexamethylenediamine from Butadiene via Hydrocyanation to Miponitrile Production Costs . . . . . . . . . . . . . . . . . . . . 220
11.1 Miponitrile by Electrohydrodimerieation of Acrylonitrile in Emulsion Summary of Asahi Chemical Patents . . . . . . . . . . . . 454
11.2 Miponitrile by Electrohydrodimerization of Acrylonitrile in an Undivided Cell PatentSummary . . . . . . . . . . . . . . . . . . . . . 456
11.3 HNDA via ADN by Electrohydrodimerization of Acrylonitrile in Solution Design Bases and Assumptions . . . . . . . . . . . . . . 229
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TABLES
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11.4
11.5
11.6
11.7
11.8
11.9
11.10
11.11
UMDA via ADN from Electrohydrodimerization of Acrylonitrile in Solution Stream Flows . . . . . . . . . . . . . . . . . . . . . . 234
UMDA via ADN from Electrohydrodimerization of Acrylonitrile in Solution
Major Equipment . . . . . . . . . . . . . . . . . . . . . 237
UMDA via ADN from Electrohydrodimerization of Acrylonitrile in Solution
Utilities Summary . . . . . . . . . . . . . . . . . . . . 241
DMDA via ADN from Electrohydrodimerization of Acrylonitrile in Solution Total Capital Investment . . . . . . . . . . . . . . . . 243
DMDA via ADN from Electrohydrodimerization of Acrylonitrile in Solution Production Costs . . . . . . . . . . . . . . . . . . . . 244
DMDA via Miponitrile by Electrohydrodimerization of Acrylonitrile in Emulsion
Design Bases and Assumptions . . . . . . . . . . . . . . 248
UMDA via ADN from Electrohydrodimerization of Acrylonitrile in Emulsion Stream Flows . . . . . . . . . . . . . . . . . . . . . . 250
UMDA via ADN from Electrohydrodimerization of Acrylonitrile in Emulsion
Major Equipment . . . . . . . . . . . . . . . . . . . . . 253
11.12 HMDA via AUN from Electrohydrodimerization of Acrylonitrile in Emulsion
Utilities Summary . . . . . . . . . . . . . . . . . . . . 256
11.13 UMLIA via ADN from Electrohydrodimerization of Acrylonitrile in Emulsion
Total Capital Investment . . . . . . . . . . . . . . . . 259
11.14 UMDA via ADN from Electrohydrodimerization of Acrylonitrile in Emulsion Production Costs . . . . . . . . . . . . . . . . . . . . 260
11.15 UMUA via AUN by Electrohydrodimerization of Acrylonitrile in An Undivided Cell Design Bases and Assumptions . . . . . . . . . . . l . . 263
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TABLES
11.16 HMDA via ADN by Electrohydrodimerization of Acrylonitrile in An Undivided Cell Stream Flows . . . . . . . . . . . . . . . . . . . . . . 266
11.17 HMDA via ADN by Electrohydrodimerization of Acrylonitrile in An Undivided Cell Major Equipment . . . . . . . . . . . . . . . . . . . . . 268
11.18 HKDA via ADN by Electrohydrodimerization of Acrylonitrile in An Undivided Cell Utilities Summary . . . . . . . . . . . . . . . . . . . . 271
11.19 BMDA via ADN by Electrohydrodimerization of Acrylonitrile in An Undivided Cell Total Capital Investment . . . . . . . . . . . . . . . . 275
11.20 HMDA via ADN by Electrohydrodimerization of Acrylonitrile in An Undivided Cell Production Costs . . . . . . . . . . . . . . . . . . . . 276
12.1 Adiponitrile from Acrylonitrile by Hydrodimerization with Sodium Amalgam
Patent Summary . . . . . . . . . . . . . . . . . . . . . 458
12.2 Catalytic Dimerization of Acrylonitrile Patent Summary . . . . . . . . . . . . . . . . . . . . . 459
12.3 Adiponitrile by Other Processes Patent Summary . . . . . . . . . . . . . . . . . . . . . 464
12.4 Hexamethylenediamine from Caprolactam PatentSummary . . . . . . . . . . . . . . . . . . . . . 466
12.5 Hexamethylenediamine from Caprolactam Production Costs . . . . . . . . . . . . . . . . . . . . 282
12.6 Hexamethylene from Diol, and Related Processes Patent Summary . . . . . . . . . . . . . . . . . . . . . 467
12.7 Hexamethylenediamine by the Diol Process Production Costs . . . . . . . . . . . . . . . . . . . . 286
12.8 Hexamethylenediamine from Propylene and Ally1 Chloride Patent Summary . . . . . . . . . . . . . . . . . . . . . 470
12.9 Other Processes for Making Hexamethylenediamine Patent Summary . . . . . . . . . . . . . . . . . . . . . 471
xvi
13.1 Nylon Salt Preparation Patent Summary . . . . . . . . . . . . . . . . . . . . . 472
13.2 Nylon Salt Solutionin Aqueous Solution Design gases and Assumptions . . . . . . . . . . . . . . 291
13.3 Nylon Salt in Aqueous Solution Stream Flows . . . . . . . . . . . . . . . . . . . . . . 293
13.4 Nylon Salt in Aqueous Solution MajorEquipment . . . . . . . . . . . . . . . . . . . . . 294
13.5 Nylon Salt in Aqueous Solution Utilities Summary . . . . . . . . . . . . . . . . . . . . 295
13.6 Nylon Salt in Aqueous Solution Total Capital Investment . . . . . . . . . . . . . . . . 297
13.7 Nylon Salt in Aqueous Solution Production Costs . . . . . . . . . . . . . . . . . . . . 298
13.8 Solid Nylon Salt from A Methanol Solution Design gases and Assumptions . . . . . . . . . . . . . . 301
13.9 Solid Nylon Salt from A Methanol Solution Stream Flows . . . . . . . . . . . . . . . . . . . . . . 302
13.10 Solid Nylon Salt from A Nethanol Solution MajorHquipment . . . . . . . . . . . . . . . . . . . . . 303
13.11 Solid Nylon Salt from A Methanol Solution Utilities Summary. . . . . . l . . . . . . . . . . . . . 304
13.12 Solid Nylon Salt from A Methanol Solution Total Capital Investment . . . . . . . . . . . . . . . . 306
13.13 Solid Nylon Salt from A Methanol Solution Production Costs . . . . . . . . . . . . . . . . . . . . 307
14.1 Polycondeneation of Mipic Acid and Hexamethylenediamine to Nylon 66
PatentSummary . . . . . . . . . . . . . . . . . . . . . 473
14.2 Additives to Nylon 66 PatentSummary . . . . . . . . . . . . . . . . . . . . . 475
14.3 Nylon Resin from Nylon Salt Continuous Process Design gases and Assumptions . . . . . . . . . . . . . . 316
14.4 Nylon 66 Resin from Nylon Salt Continuous Process Stream Flows . . . . . . . . l l l . . . . . . . . . . . 317
TABLES
14.5 Nylon 66 Resin from Nylon Salt Continuous Process MajorEquipment. . . . . . . . . . . . . . . . . . . . . 318
14.6 Nylon 66 Resin from Nylon Salt Standard Grade Utilities Summary . . . . . . . . . . . . . . . . . . . . 322
14.7 Nylon 66 Resin from Nylon Salt Utilities Summary for Aftertreatment . . . . . . . . . . 323
14.8 Nylon 66 L&sin from Nylon Salt Continuous Process Total Capital Investment . . . . . . . . . . . . . . . . 327
14.9 ,Nylon 66 Eesin from Nylon Salt Standard Grade Production Costs . . . . . . . . . . . . . . . . . . . . 330
14.10 Nylon 66 Resin from Nylon Salt Incremental Costs of Other Grades . . . . . . . . . . . . 332
14.11 Nylon 66 Eesin from Nylon Salt Batch Process Major Equipment. . . . . . . . . . . . . . . . . . . . . 335
14.12 Nylon 66 Resin from Nylon Salt Batch Process Utilities Summary . . . . . . . . . . . . . . . . . . . . 336
14.13 Nylon 66 Resin from Nylon Salt Batch Process Total Capital Investment . . . . . . . . . . . . . . . . 337
14.14 Nylon 66 Resin from Nylon Salt Batch Process Production Costs . . . . . . . . . . . . . . . . . . . . 339
14sL5 Cost Features of Nylon Eesin from Waste Fiber . . . l . . 341
15.1 Additives to Fibers Including Nylon 66 PatentSumnary . . . . . . . . . . . . . . . . . . . . . 477
15.2 Spinning of Polyamides Including Nylon 66 Patent Summary . . . . . . . . . . . . . . . . . . . . . 478
15.3 Drawing, Texturing, and Crimping of Yarn Fibers Including Nylon 66 PatentSummary . . . . . . . . . . . . . . . . . . . . . 479
15.4 Nylon Fibers to Be Evaluated . . . . . . . . . . . . . . 345
15.5 Carpet Staple from Nylon Salt Solution Total Capital Investment . . . . . . . . . . . . . . . . 346
15.6 Carpet Staple from Nylon Salt Solution Production Costs . . . . . . . . . . . . . . . . . . . . 348
15.7 Carpet Yarn from Nylon Salt Solution Total Capital Investment . . . . . . . . . . . . . . . . 350
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TABLES
15.8 Carpet Yarn from Nylon Salt Solution Production Costs . . . . . . . . . . . . . . . . . . . . 352
15.9 Tire Cord from Nylon Salt Solution Total Capital Investment . . . . . . . . . . . . . . . . 354
15.10 Tire Cord from Nylon Salt Solution Production Costs . . . . . . . . . . . . . . . . . . . . 356
15.11 Textile Yarn from Nylon 66 Chips Total Capital.Investment l . . . . . . . . . . . . . . . 358
15.12 Textile Yarn from Nylon 66 Chips Production Costs . . . . . . . . . . . . . . . . . . . . 360
15.13 Hosiery Monofilament from Nylon 66 Chips Total Capital Investment l . . . . . . . . . . . . . . . 362
15.14 Hosiery Monofilament from Nylon 66 Chips Production Costs . . . . . . . . . . . . . . . . . . . . 364
A.1 Physical Properties of Selected Chemicals . . . . . l . . 369
XIX
ILLUSTRATIONS
4.1 By-product Formation in Cyclohexane Oxidation to KA . . . 35
4.2 Reaction Mechanism for Nitric Acid Oxidation toMipicAcid..................... 37
4.3 Mipic Acid from Cyclohexane Foldout......................... 541
4.4 Boric Acid Recovery Foldout......................... 547
4.5 Recovery of Acids from Aqueous Waste Foldout......................... 549
4.6 Mipic Acid from Cyclohexane, Low Recycle Process Foldout......................... 551
5.1 Cyclohexanol from Phenol Hydrogenation Foldout......................... 553
5.2 Comparative Economics of the Phenol and Cyclohexane Processes for Making Mipic Acid . . . . . . . . . . . . 110
6.1 Mipic Acid from Butadiene Foldout......................... 557
6.2 Mipic Acid from Butadiene Block Flow Diagram . . . . . . . . . l . . . . . . . . l 122
8.1 Hexamethylenediamine from Mipic Acid Foldout......................... 561
9.1 Hexamethylenediamine from Butadiene via Dichlorobutene and Dicyanobutene Foldout......................... 567
10.1 Hexamethylenediamine from Butadiene via Hydrocyanation to Miponitrile Foldout......................... 573
10.2 IIMDA from Butadiene via Hydrogenation to Miponitrile Block Flow Diagram . . . . . . . . . . . . . . . . . . . 204
11.1 Concentration of Acrylonitrile in Electrolyte on Cathode Surface . . l . . . . . l . . . l 227
11.2 HMDA via ADN by Electrohydrodimerieation of Acrylonitrile in Solution
Foldout . . l . l . l l l l . l l . l . . . l . l l m l l 577
ILLUSTRATIONS
11.3
11.4
12.1
12.2
13.1
13.2
14.1
14.2
A.1
A.2
A.3
A.4
A.5
A.6
A.7
A.8
HMDA via ADN by Electrohydrodimerization of Acrylonitrile in Emulsion
Foldout . . . . . . . . l . . . . . . . . . . . . . . l . 583
HMDA via ADN by Electrohydrodlmerization of Acrylonitrile in An Undivided Cell
Foldout l l l . l . l l l l l l l . l l l l . l l . l l l 587
Block Diagram of Diol Process for HMDA . . . . . . . . . 284
Block Diagram of Diol Process for BMDA andMipicAcid . . . . . . . . . . . . . . . . . . . . 284
Manufacture of Nylon Salt Solution Foldout......................... 589
Manufacture of Solid Nylon Salt Foldout......................... 591
Nylon 66 l&sin by Continuous Process Foldout......................... 593
Nylon 66 Eesin by Batch Process Foldout......................... 597
Vapor Pressure of Cyclohexane, Cyclohexanol, and Cyclohexanone . . . . . . . . . . . . . . . . . . . 370
Vapor Pressure of Mipic Acid, Glutaric Acid, and Nitric Acid . . . . . . . . . . . . . . . . . . . . 371
Solubility of Succinic Acid, Mipic Acid and Glutaric Acid in Water . . . . . . . . . . . . . . . . . 372
Vapor Pressure of Methyl Esters Relevant to the Recovery of Mipic Acid by Butadiene Process . . . . . . 373
Vapor Pressure of Compounds Eelevant to the Manufacture of Miponitrile from Mipic Acid . . . . . . 374
Vapor Pressure of Compounds Relevant to the Recovery of Miponitrile by the Butadiene Process . . . 375
Vapor Pressure of Compounds Eelevant to the Recovery of Miponitrile by Electrohydrodimerization of Acrylonitrile . . . . . . . . . . . . . . . . . . . . 376
Vapor Pressure of lDlDA and 1,2-Diaminocyclohexane . . . . 377
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