polyamides other than nylons 6 and 66 - … · polyamides other than nylons 6 and 66 ... 9.2...
TRANSCRIPT
Report No. 94
POLYAMIDES OTHER THAN NYLONS 6 AND 66
PART II
by YEN-CHEN YEN
November 1974
A private report by the
PROCESS ECONOMICS PROGRAM
STANFORD RESEARCH INSTITUTE MENLO PARK, CALIFORNIA
._ - .-.
CONTENTS, PART I
1 SUMMARY ANDCOMMERCIAL ASPECTS' .............. 1
Scope ........................... 2
Aramids .......................... 2
Nylon Fibers ....................... 7
Nylon Resins ........................ 9
Polyamides Other than Nylons and Aramids. ......... 11 Technical Aspects ..................... 12
2 The usual Introduction, Summary, and Industry Status 3 sections are combined in Section 1 of this report.. . . . . 15
4 REVIEW OF PROCESSES .................... 17
Polymerization Processes. .............. 1 .. 17 Spinning. ......................... 22
Additives ......................... 23
5 ARAMIDS WHOLLY PARA-LINKED. ................ 139
Review of Processes .................... 143
Process Description .................... 154
Process Discussion .................... 170
Cost Estimates. ...................... 171
6 ARAMIDS NOT WHOLLY PARA-LINKED. .............. 183
Review of Processes .................... 184
Process Description .................... 199
Process Discussion .................... 209
Cost Estimates ....................... 209
7 PARTIALLY AROMATIC POLYAMIDES . . . . . . . . . . . . . . . 217
Review of Products and Processes ............. 217
A Process for Making Poly(Hexamethylene Terephthalamide). . 237
Process Description ................... 237
Process Discussion ................... 247
Cost Estimates ..................... 247
A Process for Making Nylon 3M6,T ............. 251
Process Description ................... 251
Process Discussion ................... 259
Cost Estimates ..................... 259
iii
CONTENTS, PART II
8
9
10
11
12
ALICYCLIC POLYAMIDES ................... 263
Review of Processes .................... 263
A Process for Making Nylon PACM,12 ............. 278 Process Description ................... 278 Process Discussion ................... 287 Cost Estimates ..................... 287
ALIPHATIC POLYAMIDES FROM DIAMINES AND DIACIDS ...... 295
Review of Products and Processes ............. 295 Process Description .................... 305
Process Discussion .................... 315
Cost Estimates ...................... 315
ALIPHATIC POLYAMIDES OTHER THAN NYLON 12, 11, OR 4 FROM LACTAMS OR AMINO ACIDS ..................
General ..........................
Nylon3 ..........................
Nylon7 ........... . ..............
Nylon9.. ........................
Nylon13 ......................... Nylon2 ..........................
Nylon8 ..........................
Nylon5 ..........................
Nylon10 .........................
321
321
324
333 334
335 335
336
336
337
NYLON12 .........................
Chemistry .. ........................ Review of Processes .................... Process Description .................... Process Discussion .................... Cost Estimates ......................
339
339 340 347 354 355
NYLON11 .........................
Chemistry ......................... Review of Processes .................... Process Description .................... Process Discussion .................... Cost Estimates ......................
359
359 360 360 368 368
iv
-
a . CONTENTS, PART II
13 NYLON4 .......................... 373
Chemistry ......................... 373
Review of Processes .................... 375 Process Description .................... 380
Process Discussion .................... 387
Cost Estimates ...................... 387
14 OTHER POLYAMIDES ..................... 391
Polyamides Containing Heterocyclic Groups ......... 391
Polyamides from Fatty Acids ................ 392
Unsaturated Polyamides .................. 392 Polyamides Containing Hetero Atoms ............ 392
Polyamides Containing N-Alkoxyalkyl Groups ........ 393 Copolyamides and Polyamide Blends ............. 393 Bicomponent Fibers .................... 393
APPENDIX A DESIGN AND COST BASES . . . . . . . . . . . . . . . 443
APPENDIX B PHYSICAL AND CHEMICAL DATA . . . . . . . . . . . . . 445
APPENDIX C SOME CONVERSIONS . . . . . . . . . . . . . . . . . . 459
APPENDIX D NYLON NOMENCLATURE . . . . . . . . . . . . . . . . . 461
CITED REFERENCES . . . . . . . . . . . . . . . . . . . . . . . . 463
PATENT REFERENCES BY COMPANY . . . . . . . . . . . . . . . . . . 615
V
ILLUSTRATIONS, PART II
0
8.1 Nylon PACM,12 Yarn Manufacture
Flow Sheet . . . . . . . . . . . . . . . . . . . . . . . . . 283
8.2 Nylon PACM,12 Yarn Manufacture
Effect of Operating Level and Plant Capacity
on Production Cost . . . . . . . . . . . . . . . . . . . . . 293
9.1 Nylon 612 Chip Manufacture Operation Cycle of Polycondensation Reactor . . . . . . . . . 306
9.2 Nylon 612 Chip Manufacture Flow Sheet . . . . . . . . . . . . . . . . . . . . . . . . . 311
9.3 Nylon 612 Chip Manufacture Effect of Operating Level and Plant Capacity on Production Cost .'. . . . . . . . . . . . . . . . . . . . 319
11.1 Nylon 12 Chip Manufacture Flow Sheet . . . . . . . . . . . . . . . . . . . . . . . . . 351
11.2 Nylon 12 Chip Manufacture Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . . 358 .
12.1 Nylon 11 Chips by Continuous Process Flow Sheet . . . . . . . . . . . . . . . . . . . . . . . . . 365
12.2 Nylon 11 Chips by Continuous Process Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . . 372
13.1 Nylon 4 Chip Manufacture Flow Sheet . . . . . . . . . . . . . . . . . . . . . . . _. . 383
13.2 Nylon 4 Chip Manufacture Effect of Operating Level and Plant Capacity
on Production Cost . . . . . . . . . . . . . . . . . . . . . 390
a
vii
TABLES, PART II
8.1 Polyamides from Di(p-Aminocyclohexyl) Methane (PACM) and
Its Homologues
Patent Summary....................... 264
8.2 Polyamides from Isophorone Diamine
Patent Summary . . . . . . . . . . , . . . . . . . . . . . . 268
8.3 Other Polyamides Containing Alicyclic Groups Patent Summary. . . . . . . . . . , . . . . . . . . . . . . 270
8.4 Miscellaneous Alicyclic Groups Used in Polyamides Patent and Article References . . . . . . . . . . . . . . . 275
8.5 Nylon PACM, 12 Yarn Manufacture Design Bases and Assumptions . . . . . . , . . . . . . . . . 278
8.6 Nylon PACM,12 Yarn Manufacture Major Process Equipment and Utilities Summary. . . . . . . . 281
8.7 Nylon PACM,12 Yarn Manufacture Stream Flows. . . . . . . . . . . . . . . . . . . . . . . . 285
8.8 Nylon PACM,12 Yarn Manufacture Waste Streams . . . . . . . . . . . . . . . . . . . . . , . 286
8.9 Nylon PACM,lZ Yam Manufacture Total Capital Investment . . . . . . . . . . . . . . . . . . 289
8.10 Nylon PACM,12 Yarn Manufacture
Production Costs . . . . . . . . . . . . . . . . . . . . . . 291
9.1 Aliphatic Polyamides fran Diamines and Diacids
Patent Summary . . . . . . . . . . . . . . . , . . . . .,. . 298
9.2 Polyoxamides Patent Summary. . . . . . . . . . . . . . . , . . . . . . . 304
9.3 Nylon 612 Chip Manufacture Design Bases and Assumptions . . . . . . . . . . . . . . . . 305
9.4 Nylon 612 Chip Manufacture Major Process Equipment and Utilities Summary . . . . . . . 309
9.5 Nylon 612 Chip Manufacture Stream Flows........................ 313
9.6 Nylon 612 Chip Manufacture Waste Streams . . . . . . . . . . . . . . . . . . . . . . . 314
9.7 Nylon 612 Chip Manufacture Total Capital Investment . . . . . . . . . . . . . . . . . . 316
iX
TABLES, PART II
9.8 Nylon 612 Chip Manufacture production Costs , . . . . . . . l . l l l l l l l l l l l l 317
10.1 Monomers for Nylons . . . . . . . l . l l l l l l l . l l l 323
10.2 Polyamides Other Than Nylon 12, 11, 4, or 3 from Amino Acids and Lactams Patent Summary. . . . . . . . . . l - - l l l l l - l l l - 325
10.3 Nylon 3 Patent Summary. . . . . . . . . . . l l l l l l l l l l l l
328
11.1 Nylon 12 Patent summary....................... 341
11.2 Nylon 12 Chip Manufacture Design Bases and Assumptions . . . . . . . . . . . . . . . . 348
11.3 Nylon 12 Chips by Continuous Process Major Process Equipment and Utilities Summary . . . . . . . 351
11.4 Nylon 12 Chips by Continuous Process
Stream Flows........................ 353
11.5 Nylon 12 Chips by Continuous Process
Total Capital Investment . . . . . . . . . . . . . . . . . . 356
11.6 Nylon 12 Chips by Continuous Process
Production Costs . . . . . . . . . . . . . . . . . . . . . . 357
12.1 Nylon 11
Patent Summary . . . . . . . . . . . . . . . . . . . . . . . 361
12.2 Nylon 11 Chips by Continuous Process
Design Bases and Assumptions . . . . . . . . . . . . . . . , 363
12;3 Nylon 11 Chips by Continuous Process
Major Process Equipment and Utilities Summary . . . . . . . 365
12.4 Nylon 11 Chips by Continuous Process
Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . 367
12.5 Nylon 11 Chips by Continuous Process Total Capital Investment . . . . . . . . . . . . . . . . . . 370
12.6 Nylon 11 Chips by Continuous Process Production Costs . . . . . . . . . . . . . . . . . . . . . . 371
13.1 Nylon 4 (Polypyrrolidone) Patent Summary. . . . . . . . . . . . . . . . . . . . . . . 376
13.2 Nylon 4 Chip Manufacture Design Bases and Assumptions . . . . . . . . . . . , . . . . 381
X
TABLES, PART II
13.3
13.4
13.5
13.6
13.7
14.1
14.2
14.3
14.4
14.5
14.6
14.7
14.8
14.9
14.10
14.11
14.12
Nylon 4 Chip Manufacture Major Process Equipment and Utilities Summary . . . . . . .
Nylon 4 Chip Manufacture Stream Flows........................
Nylon 4 Chip Manufacture Waste Streams . . . . . . . . . . . . . . . . . . . . . . .
Nylon 4 Chip Manufacture Total Capital Investment . . . . . . . . . . . . . . . . . .
Nylon 4 Chip Manufacture Production Costs . . . . . . . . . . . . . . , . . . . . . .
Polyamides from Piperazine or its Derivatives Patent Summary. . . . . . . . . . . . . . . . . . . . . , .
Polyamides from Heterocyclic Compounds Patent Summary. . . . . . . . . . . . . . . . . . . . . . .
Polyamides with Heterocyclic Groups Formed During or After Polymerization
Patent Summary. . . . . . . . . . . . . . . . . . . . . . . .
Polyamides from Polymeric Fatty Acids
Patent Summary . . . . . . . . . . . . . . . . . . . . . . .
Polyamides from Unsaturated Fatty Acids
Patent Summary. . . . . . . . . . . . . . . . . . . . . . .
Unsaturated Polyamides Patent Summary . . . . . . . . . . . . . . . . . . . . . . . .
Sulfur-Containing Polyamides Patent Summary. . . . . . . . . . . . . . . . . . . . . . .
Halogen-Containing Polyamides Patent Summary. . . . . . . . . . . . . . . . . . . . . . .
Phosphorus-Containing Polyamides Patent summary.......................
Silicon-Containing Polyamides Patent Summary. . . . . . . . . . . . . . . . . . . . . . .
Boron-Containing Polyamides Patent summary.......................
N-Alkoxyalkyl Polyamides and Related Polymers Patent summary.......................
383
385
386
388
389
395
397
400
401
405
406
407
411
412
413
414
415
xi
TABLES, PART II
14.13 Polyester-Amides Patent Summary ....................... 417
14.14 Polyamide Copolymers
Patent Summary ....................... 423
14.15 Copolymers or Blends Containing Polyamides and Other Polymers Patent Summary. ...................... 425
14.16 Bicomponent Fibers Patent Summary ....................... 431
B.l Properties of Kevlar@ and Certain Other Tire Cord Materials ....................... 447
B.2 Properties of Kevlar@ 49 and Kevlar @ 29 .......... 447
B.3 Properties of Nomex@Yarn ................. 448
B.4 Properties of Certain Nylons as Plastics .......... 449
B.5 Melting Points and Glass Transition Temperatures of Polyamides ....................... 450
B.6 Inherent Viscosities of Certain Polyamides ......... 453
B.7 Properties of N,Methylpyrrolidone ............. 454
B.8 Properties of Hexamethylphosphoramide ........... 455
B.9 Properties of Dimethylacetamide .............. 456
B.10 Heats of Reaction During Polyamide Formation ........ 457
xii