Page 1
PROCESS ECONOMICS
PROGRAM
Abstract
SRI INTERNATIONAL
Menlo Park, California
94025
Process Economics Program Report No. 1D
ISOCYANATES
(July 1983)
In this report, SRI reviews the technology for making commercial
and experimental nonaromatic isocyanates. The commercial isocyanates
include hexamethylene diisocyanate, hydrogenated MDI, isophorone
diisocyanate, dimer diisocyanate, xylylene diisocyanate, hydrogenated
xylylene diisocyanate, and trimethylhexamethylene diisocyanate. The
experimental nonaromatic isocyanates that we reviewed include 1,6,11-
undecane triisocyanate, lysine-ethylester triisocyanate, trans-
cyclohexane diisocyanate, and tetramethylxylylene diisocyanate.
We evaluated eight phosgenation processes and one nonphosgenation
process. We also evaluated two processes which manufacture respec-
tively an adduct of hexamethylene diisocyanate and a blocked isophorone
diisocyanate.
PEP'82 YRC/CN
Page 2
c I
a 0 a m
Report No. 1D
ISOCYANATES
SUPPLEMENT D
by YU-REN CHIN
wlth contributions by CHIEN NIEH
July 1983
A private report by the
PROCESS ECONOMICS PROGRAM
Menlo Park, California 94025
Page 3
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
major hjdrocarbons and their derivatives on a worldwide basis.
In addition, the SRI DIRECTORY OF CHEMICAL PRODUCERS services
provide detailed lists of chemical producers by company, prod-
uct, and plant for the United States and Western Europe.
ii
Page 4
1
2
3
4
5
6
CONTENTS
INTRODUCTION. ....................... 1
SUMMARY .......................... 3
General Aspects ...................... 3 Technical Aspects ..................... 4 Economic Aspects. ..................... 5
INDUSTRY STATUS ...................... 15
Markets .......................... 15 Producers ......................... 16
HEXAMETHYLENE DIISOCYANATE. ................ 19
Chemistry ......................... 19 Process Description .................... 21 Phosgenation of Hexamethylenediamine. .......... 21 Phosgene and HCl Recovery ................ 23
Process Discussion. .................... 27 Cost Estimates. ...................... 27
HYDROGENATED MDI. .....................
Chemistry ......................... Review of Processes .................... Process Description--Manufacture of MDA .......... Cost Estimates--Manufacture of MDA. ............ Process Description--Manufacture of Hydrogenated MD1 fromMDA .......................... Hydrogenation of MDA. .................. Phosgenation of Hydrogenated MDA. ............ Recovery of Phosgene and HCl. ..............
Process Discussion--Manufacture of Hydrogenated MD1 fromMDA .......................... Cost Estimates--Manufacture of Hydrogenated MD1 fromMDA ..........................
39
39 40 43 44
49 49 51 52
58
58
ISOPHORONE DIISOCYANATE ..................
Chemistry ......................... Review of Processes .................... Process Description .................... Cyanoketone Production. ................. Isophorone Diamine Production .............. Isophorone Diisocyanate Production. ........... Product Purification and Phosgene Recovery. .......
71
71 74 74 77 77 78 78
iii
Page 5
CONTENTS
6 ISOPHORONE DIISOCYANATE (Continued)
Process Discussion. . . . . . . . . . . . , . . . . . . . . Cost Estimates. . . . . . . . . . . . . . . . . . . . . . .
7 XYLYLENE DIISOCYANATE AND HYDROGENATED XYLYLENE DIISOCYANATE. .......................
Chemistry ......................... Review of Processes .................... Process Description--XDA from Xylene. ........... Amnoxidation of Xylene to Isophthalonitrile ....... Hydrogenation of Phthalonitrile .............
Process Discussion--XDA from Xylene ............ Cost Estimates--XDA from Xylene .............. Process Description--H6XDA from XDA ............ Process Discussion--H6XDA from XDA. ........... Cost Estimates--HgXDA from XDA. .............
Process Description--XDI from XDA ............. Phosgenation of XDA ................... Purification of XDI ................... Process Discussion--XDI from XDA. ............ Cost Estimates--XDI from XDA. ..............
Economics of the H6XDI Process. .............. Sunnnary ..........................
8 TRIMETHYLHEXAMETHYLENE DIISOCYANATE ............
Chemistry ......................... Review of Processes .................... Process Description--TMHDA from Isophorone. ........ Trimethylcyclohexanol Production. ............ Trimethyl Adiponitrile Production ............ Trimethylhexamethylene Diamine Production ........
Process Discussion--TMHDA from Isophorone ......... Cost Estimates--TMHDA from Isophorone ........... Process Description--TMHDI from TMHDA ........... Cost Estimates--TMHDI from TMHDA. .............
9 DIMER DIISOCYANATE. ....................
Chemistry ......................... Manufacture of Dimer Amine. ................ Manufacture of Dimer Diisocyanate .............
Process Description ................... Cost Estimates. .....................
iv
86 86
95
95 96 98 98
100 109 109 116 121 121 127 127 127 134 134 142 142
145
145 148 148 155 155 156 162 163 170 176
183
183 184 188 188 189
-
Page 6
CONTENTS
10 TRIISOCYANATES. . . . . . . . . . . . . . . . . . . . . . . 197
Chemistry . . . . . . . . . . . . . . . . . . . . , Review of Processes . . . . . . . . . . . . . . . . Process Description--1,6,11-Undecane Triisocyanate. Production of Tetrahydroazepine . . . , . . . . . Production of Undecane Triamine . . . . . . . . . Production of Undecane Triisocyanate. . . , . . . Recovery of Lithium Hydroxide, Phosgene, and HCl.
Process Discussion--1,6,11-Undecane Triisocyanate . Cost Estimates--1,6,11-Undecane Triisocyanate , . . Process Description--Lysine-ethylester Triisocyanate . . . . . . . . . . . . . . . , . . . Production of Lysine-8-aminoethylester Tri-HCl. . Production of Lysine-ethylester Triisocyanate . . Recovery of Solvents, Phosgene and HCl. . . . . .
Process Discussion--Lysine-ethylester Triisocyanate Cost Estimates --Lysine-ethylester Triisocyanate . .
. . . . 197
. . . . 201
. . . . 201
. . . . 205
. . . . 205
. . . . 206
. . . . 207 , . . . 216 . . . . 217
. . . . 225
. . . . 225
. . . . 227
. . . . 227
. . . . 235
. . . . 235
11 TRANS-CYCLOHEXANE-1,4-DIISOCYANATE. ............
Chemistry ......................... Review of Processes .................... Process Description .................... Production of CHDCA ................... Production of CHDI. ................... Purification of CHDI. ..................
Process Discussion. .................... Cost Estimates. ......................
12 TETRAMETRYLXYLYLENE DIISOCYANATE. . . . . . . . . . . . . . 267
13 ADDUCTS ..........................
Biurets .......................... Blocked Isocyanates ., ................... Adducts with Polyols. ................... Isocyanurates ....................... A Process for Making Biuret from BDI. ...........
Process Description ................... Process Discussion. ................... Cost Estimates. .....................
A Process for Making Blocked IPDI ............. Process Description ................... Process Discussion. ................... Cost Estimates. .....................
245
245 246 248 248 250 251 257 257
269
269 272 272 275 278 278 282 282 287 287 291 291
V
Page 7
CONTENTS
14 OTHER NONAROMATIC ISOCYANATES . . . . . . . . . . . . . . .
Phosgenation Processes, . . . . . . . . . . . . . Nonphosgenation Processes . . . . . . . . . . . . Thermal Decomposition of Substituted Urethane . Thermal Decomposition of Adduct of Furoxan and Vicinal Diketone. . . . . . . . . . . . . . Reaction of N-chloroamide with a Tertiary Amine Oxidation of N-Substituted Formamide. . . . . . Reaction of Amine and Chloroformate . . . . . . Reaction of Amide with Alkali Metal Hypobromite Isocyanates from Substituted Urea . . . . . . . Isocyanates from Carbamic Acid Salt or Acid Chloride. . . . . . . . . . . . . . . . . . . .
Miscellaneous Processes . . . . . . . . . . . . .
. . . . .
. . . . .
. . . . I
. . . . . 306
. . . . . 307
. . . . . 307
. . . . . 308
. . . . . 308
. . . . . 309
. . . . .
. . . . .
APPENDIX A--DESIGN AND COST BASIS. . . . . . . . . . . . . . . .
APPENDIX B--PHYSICAL PROPERTIES. . . . . . . . . . . . . . . . .
CITEDREFERENCES........................
PATENTREFERENCES BYCOMPANY. . . . . . . . . . . . . . . . . .
297
297 305 305
310 310
311
315
317
325
vi
Page 8
ILLUSTRATIONS
4.1
4.2
5.1
5.2
5.3
6.1
6.2
7.1
7.2
7.3
7.4
7.5
Hexamethylene Diisocyanate from Hexamethylene Diamine by Phosgenation Flowsheet........................
Hexamethylene Diisocyanate from Hexamethylene Diamine by Phosgenation Effect of Plant Capacity and Operating Level on Product Values of Plant A and Plant B. , . . . . . . .
MDA from Aniline and Formaldehyde Effect of Operating Level and Plant Capacity on Production Cost. . . . . . . . . . . . . . . . . . . .
Hydrogenated MD1 from MDA Flowsheet........................
Hydrogenated MD1 from MDA Effect of Operating Level and Plant Capacity on Product Value. . . . . . . . . . . . . . . . . . . . .
Isophorone Diisocyanate FlowSheet........................
Isophorone Diisocyanate Effect of Operating Level and Plant Capacity on Production Cost. , . . . . . . . . . . . . . . . . . .
Xylylene Diamine from Xylene by Ammoxidation and Hydrogenation Flow Sheet. ; . . . . . . . . . . . . . . . . . . . . . .
Xylylene Diamine from Xylene by Ammoxidation and Hydrogenation Effect of Operating Level and Plant Capacity on Production Cost. . . . . . . . . . . . . . . . . . . .
Hydrogenated Xylylene Diamine from XDA Flowsheet........................
Hydrogenated Xylylene Diamine from Xylylene Diamine Effect of Operating Level and Plant Capacity on Production Cost. . . . . . . . . . . . . . . . . . . .
Xylylene Diisocyanate from Xylene Diamine by Phosgenation Flowsheet........................
329
37
48
333
67
335
93
339
115
343
125
345
vii
Page 9
ILLUSTRATIONS
7.6 Xylylene Diisocyanate from Xylylene Diamine by Phosgenation Effect of Operating Level and Plant Capacity on Production Cost. . . . . . . . . . . . . . . . . . . .
8.1 Trimethylhexamethylene Diamine from Isophorone FlowSheet........................
8.2 Trimethylhexamethylene Diamine from Isophorone Effect of Operating Level and Plant Capacity on Production Cost. . . . . . . . . . . . . . . . . , . .
8.3 Trimethylhexamethylene Diisocyanate from Trimethylhexamethylene Diamine FlowSheet........................
8.4 Trimethylhexamethylene Diisocyanate from Trimethylhexamethylene Diamine Effect of Operating Level and Plant Capacity on Production Cost. . . . . . . . . . . . . . . . . . . .
9.1 Dimer Diisocyanate from Dimer Amine FlowSheet........................
9.2 Dimer Diisocyanate from Dimer Amine Effect of Operating Level and Plant Capacity on Production Cost. . . . . . . , . . . . . . . . . . , .
10.1 1,6,11-Undecane Triisocyanate from Caprolactam FlowSheet.; . . . . . . . . . . . . . . . . . . . . . .
10.2 1,6,11-Undecane Triisocyanate from Caprolactam Effect of Operating Level and Plant Capacity on Production Cost. . . . . . . . , . . . . . . . . . . .
10.3 Lysine-ethylester Triisocyanate from L-Lysine Monohydrochloride FlowSheet........................
10.4 Lysine-ethylester Triisocyanate from L-Lysine Monohydrochloride Effect of Operating Level and Plant Capacity on Production Cost. . . . . . . . . . . . . . . . . . . .
11.1 Trans-1,4-cyclohexane Diisocyanate from Dimethyl-trans-cyclohexane-1,4-dicarboxylate FlowSheet........................
141
347
169
351
180
353
196
357
224
361
242
367
viii
Page 10
ILLUSTRATIONS
11.2 Trans-1,4-cyclohexane Diisocyanate from Dimethyl-trans-cyclohexane-1,4-dicarboxylate Effect of Operating Level and Plant Capacity on Production Cost. . . , . . . . . . , . . . . . . . . .
11.3 Trans-1,4-cyclohexane Diisocyanate from Dimethyl-trans-cyclohexane-1,4-dicarboxylate Effect of DMCHD Price on Production Cost. . . . . . . . .
13.1 Biuret from Hexamethylene Diisocyanate Flowsheet........................
13.2 Biuret from Hexamethylene Diisocyanate Effect of Operating Level and Plant Capacity on Production Cost, . . . . . . . . . . . . . . . . . . .
13.3 Blocked Isocyanate from Isophorone DiiSOCyaMte FlowSheet........................
13.4 Blocked Isocyanate from Isophorone Diisocyanate Effect of Operating Level and Plant Capacity on Production Cost. . . . . . . . . . . . . . . . . . . .
14.1 Production Related Cost as a Function of Plant Capacity.........................
14.2 Product Value Related Cost as a Function of Plant Capacity.........................
264
265
369
286
371
295
302
303
iX
Page 11
TABLES
2.1 Nonaromatic Di- and Triisocyanates Summary of Technical Aspects. . . . . . . . . . . . . . .
2.2 Three Major Nonaromatic Diisocyanates Summary of Economics. . . , . . . . . . . . . . . , . . .
2.3 Other Commercial Nonaromatic Diisocyanates Surmnary of Economics. . . . . . , . . . . . . . . . . . .
2.4 Nonaromatic Di- or Triisocyanates in Development Stage Sunxnary of Economics. . . , . . . . . . . . . . . . . . .
2.5 ED1 Biuret and Blocked IPDI Sunxnary of Economics. . . . . . . . . . . . . . . . . . .
3.1 World Producers of Nonaromatic Di- or Polyisocyanates as of End-1982. . . . . . . . . . . . . .
4.1 Hexamethylene Diisocyanate from Hexamethylenediamine by Phosgenation Design Bases and Assumptions. . . . . . . . . . . . . . .
6
10
11
12
14
17
22
4.2 Hexamethylene Diisocyanate from Hexamethylenediamine by Phosgenation StreamFlows. . . . . . . . . . . . . . . . . . . . . . . 24
4.3 Hexamethylene Diisocyanate from Hexamethylenediamine by Phosgenation MajorEquipment.....................
4.4 Hexamethylene Diisocyanate from Hexamethylenediamine by Phosgenation Utilities Summary . . . . . . . . . . . . . . . . . . . .
4.5 Hexamethylene Diisocyanate from Hexamethylenediamine by Phosgenation Total Capital Investment. . . . . . . . . . . . . . . . .
4.6 HDI from HMDA by Phosgenation Using Tertiary Amine Total Capital Investment. . . . . . . . . . , . . . . . .
4.7 Hexamethylene DiiSOCyaMte from Hexamethylenediamine by Phosgenation Production Costs. . . . . . . . . . . . . . . . . . . . .
4.8 HDI from HMDA by Phosgenation Using Tertiary Amine Production Costs. . . . . . . . . . . . . . . . . . . . .
25
26
29
31
32
35
Xi
Page 12
TABLES
5.1 Hydrogenated MD1 from MDA PatentSummary......................
5.2 MDA from Aniline and Formaldehyde Total Capital Investment. . . . . . . . . . . . . . . . .
5.3 MDA from Aniline and Formaldehyde Production Costs. . . . . , . . . . . . . . . . . . . . .
5.4 Hydrogenated MD1 from MDA Design Bases and Assumptions. . . . . . . . . . . . . . .
5.5 Hydrogenated MD1 from MDA StreamFlows. . . . . . . . . . . . . . . . . . . . . . .
5.6 Hydrogenated MD1 from MDA Major Equipment. . . . . . . . . . . . . . . . . . . . .
5.7 Hydrogenated MD1 from MDA Utilities Sunnnary . . . . . . . . . . . . . . . . . . . .
5.8 Hydrogenated MD1 from MDA Total Capital Investment. . . . . . . . . . . . . . . . .
5.9 Hydrogenated MD1 from ?lDA Production Costs. . . . . . . . . . . . . . . . . . . . .
5.10 Hydrogenated MDA from MDA Production Costs. . . . . . . . . . . . . . . . . . . . .
5.11 Hydrogenated MD1 from Hydrogenated MDA Production Costs. . . . . . . . . . . . . . . . . . . . .
6.1 Isophorone Diisocyanate PatentSummary......................
6.2 Isophorone Diisocyanate Design Bases and Assumptions. . . . . . . . . . . . . . .
6.3 Isophorone Diisocyanate StreamFlows. . . . . . . . . . . . . . . . . . . . . . .
6.4 Isophorone DiiSOCyaMte Major Equipment.....................
6.5 Isophorone Diisocyanate Utilities Summary . . . . . . . . . . . . . . . . . . . .
6.6 Isophorone Diisocyanate Total Capital Investment. . . . . . . . . . . . . . . . .
6.7 Isophorone Diisocyanate Production Costs. . . . . . . . . . . . . . . . . . . . .
41
45
46
50
53
55
57
60
62
65
68
75
76
80
82
85
88
90
xii
Page 13
7.1 XDI and H$DI from Xylene via XDA and H+DA Patent Summary. . . . . . . . . . . , , , . .
7.2 Xylylene Diamine from Xylene by Ammoxidation and Hydrogenation Design Bases and Assumptions. . . . . , . . .
7.3 Xylylene Diamine from Xylene Ammoxidation and Hydrogenation Stream Flows. . . . . . . . . . . . . . . . .
7.4 Xylylene Diamine from Xylene by Ammoxidation and Hydrogenation Major Equipment . . . . . . . . . . . . . . .
7.5 Xylylene Diamine from Xylene by Ammoxidation and Hydrogenation Utilities Summary . . . . . . . . . . . . . .
7.6 Xylylene Diamine from Xylene by Ammoxidation and Hydrogenation Total Capital Investment. . . . . . . . . . .
7.7 Xylylene Diamine from Xylene by Ammoxidation and Hydrogenation Production Costs. . . . . . . . . . . . . . .
7.8 Hydrogenated Xylylene Diamine from Xylylene Diamine Design Bases and Assumptions. . . . . . . . .
7.9 Hydrogenated Xylylene Diamine from Xylylene Diamine Stream Flows. . , . . . . . . . . . . . . . .
7.10 Hydrogenated Xylylene Diamine from Xylylene Diamine Major Equipment. . . . . . . . . . . . . . .
7.11 Hydrogenated Xylylene Diamine from Xylylene Diamine Utilities Summary . . . . . . . . . . . . . .
7.12 Hydrogenated Xylylene Diamine from Xylylene Diamine Total Capital Investment. .' . . . . . . . . .
7.13 Hydrogenated Xylylene Diamine from Xylylene Diamine Production Costs. . . . . . . . . . . . . . .
. . . . . .
......
......
......
......
......
......
......
......
......
......
......
......
97
101
102
106
108
110
112
117
118
119
120
122
123
xiii
Page 14
TABLES
7.14 Hydrogenated Xylylene Diamine from Xylylene Diamine Production Costs. . . . . . . . . . . . . . . . . . . . .
7.15 Xylylene Diisocyanate from Xylylene Diamine by Phosgenation Design Bases and Assumptions. . , . . . . . . . . . . . .
7.16 Xylylene Diisocyanate from Xylylene Diamine by Phosgenation Stream Flows. . . . . . . . . . . . . . . . . . . . . . .
7.17 Xylylene Diisocyanate from Xylylene Diamine by Phosgenation Major Equipment . . . . . . . . . . . . . . . . . . . . .
7.18 Xylylene Diisocyanate from Xylylene Diamine by Phosgenation Utilities Summary . . . . . . . . . . . . . . . . . . . .
7.19 Xylylene Diisocyanate from Xylylene Diamine by Phosgenation Total Capital Investment. . . . . . . . . . . . . . . . .
7.20 Xylylene Diisocyanate from Xylylene Diamine by Phosgenation Production Costs. . . . . . . . . . . . . . . . . . . . .
7.21 Xylylene Diisocyanate from Xylylene Diamine by Phosgenation Production Costs. . . . . . . . . . . . . . . . . . . . .
7.22 %XDI from H6XDA Cost Features . . . . . . . . . . . . . . . . . . . . . .
8.1 Trimethylhexamethylene DiiSOCyaMte PatentSummary......................
8.2 Trimethylhexamethylene Diamine from Isophorone Design Bases and Assumptions. . . . . . . . . . . . . . .
8.3 Trimethylhexamethylene Diamine from Isophorone StreamFlows. . . . . . . . . . . . . . . . . . . . . . .
8.4 Trimethylhexamethylene Diamine from Isophorone Major Equipment. . . . . . . . . . . . . . . . . . . . .
8.5 Trimethylhexamethylene Diamine from Isophorone Utilities Summary . . . . . . . . . . . . . . . . . . . .
xiv
126
128
130
131
133
135
137
140
143
150
154
157
159
161
Page 15
TABLES
8.6 Trimethylhexamethylene Diamine from Isophorone Total Capital Investment. . . . . . . . . . . . . . . . .
8.7 Trimethylhexamethylene Diamine from Isophorone Production Costs. . . . . . . . . . . . . . . . . . . . .
8.8 Trimethylhexamethylene Diisocyanate from Trimethylhexamethylene Diamine Design Bases and Assumptions. . . . . . . , . . . . . . .
8.9 Trimethylhexamethylene Diisocyanate from Trimethylhexamethylene Diamine StreamFlows. . . . . . . . . . . . . . . . . . . . . . .
8.10 Trimethylhexamethylene Diisocyanate from Trimethylhexamethylene Diamine MajorEquipment.....................
8.11 Trimethylhexamethylene Diisocyanate from Trimethylhexamethylene Diamine Utilities Summary . . . . . . . . . . . . . . . . . . . .
8.12 Trimethylhexamethylene Diisocyanate from Trimethylhexamethylene Diamine Total Capital Investment. . . . . . . . . . . . . . . . .
8.13 Trimethylhexamethylene Diisocyanate from Trimethylhexamethylene Diamine Production Costs. . . . . . . . . . . . . . . . . . . . .
8.14 Trimethylhexamethylene Diisocyanate from Isophorone Production Costs. . . . . . . . . . . . . . . . . . . . .
9.1 Dimer Amine Manufacture from Dimer Acid Total Capital Investment. . . . . . . . . . . . . . . . .
9.2 Dimer Amine Manufacture from Dimer Acid Production Costs. . . . . . . . . . . . . . . . . . . . .
9.3 Dimer Diisocyanate from Dimer Amine Design Bases and Assumptions. , . . . . . . . . . . . . .
9.4 Dimer Diisocyanate from Dimer Amine StreamFlows. . . . . . . . . . . . . . . . . . . . . . .
9.5 Dimer Diisocyanate from Dimer Amine MajorEquipment.....................
9.6 Dimer Diisocyanate from Dimer Amine Utilities Sunrnary . . . . . . . . . . . . . . . . . . . .
164
166
171
172
173
175
177
178
181
185
186
189
190
191
192
xv
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TABLES
9.7
9.8
10.1
10.2
10.3
10.4
10.5
10.6
10.7
10.8
10.9
10.10
10.11
10.12
10613
Dimer Diisocyanate from Dimer Amine Total Capital Investment. . . . . . . . . . . .
Dimer Diisocyanate from Dimer Amine Production Costs. . . . . . . . . , . . . . . .
Aliphatic Triisocyanates Patent Sunmmry. . . . . . . . . . . . . . . . .
1,6,11-Undecane Triisocyanate from Caprolactam Design Bases and Assumptions. . . . . . . . . .
1,6,11-Undecane Triisocyanate from Caprolactam Stream Flows. . . . . . . . . . . . . . . . . .
1,6,11-Undecane Triisocyanate from Caprolactam Major Equipment . . . . . . . . . . . . . . . .
1,6,11-Undecane Triisocyanate from Caprolactam Utilities Summary . . . . . . . . . . . . . . .
1,6,11-Undecane Triisocyanate from Caprolactan Total Capital Investment. . . . . . . . . . . .
1,6,11-Undecane Triisocyanate from Caprolactam Production Costs. . . . . . . . . . . . . . . .
Lysine-ethylester Triisocyanate from L-Lysine Monohydrochloride Design Bases and Assumptions. . . . . . . . . .
. . . . .
. . . . .
. . . . .
. . . . .
. . . . .
. . . . .
. . . . .
. . . . .
. . . . .
. . . . . 226
Lysine-ethylester Monohydrochloride Stream Flows. . .
Lysine-ethylester Monohydrochloride Major Equipment .
Lysine-ethylester Monohydrochloride Utilities Summary
Triisocyanate from L-Lysine
. . . . . . . . . . . . . . . . . . . .
Triisocyanate from L-Lysine
. . . . . . . . . . . . . . . . . . . .
Triisocyanate from L-Lysine
. . . . . . . . . . . . . . . . . . . .
Lysine-ethylester Triisocyanate from L-Lysine Monohydrochloride Total Capital Investment. . . . . . . . . . . . . . . . .
Lysine-ethylester Triisocyanate from L-Lysine Monohydrochloride Production Costs. . . . . . . . . . . . . . . . . . . . .
a 193
194
202 l 204
209
211
215
218 l 221
229
232
234
237 a
239
l xvi
Page 17
TABLES
10.14 L-Lysine Monohydrochloride from Cyclohexanol Economics........................
10.15 L-Lysine Monohydrochloride from Cyclohexanol Raw Material and Utilities Costs. . . . . . . . . . . . .
11.1 Trans-1,4-cyclohexane Diisocyanate from Dimethyl-trans-cyclohexane-1,4-dicarboxylate Patentsunnnary......................
11.2 Trans-1,4-cyclohexane Diisocyanate from Dimethyl-trans-cyclohexane-1,4-dicarboxylate Design Bases and Assumptions. . . . . . . . . . . . . . .
11.3 Trans-1,4-cyclohexane Diisocyanate from Dimethyl T-cyclohexane-1,4-dicarboxylate Stream Flows. . . . . . . , . . . . . . . . . . . . . , .
11.4 Trans-1,4-cyclohexane Diisocyanate from Dimethyl T-cyclohexane-1,4-dicarboxylate Major Equipment . . . . . . . . . . . . . . . . . . . . .
11.5 Trans-1,4-cyclohexane Diisocyanate from Dimethyl T-cyclohexane-1,4-dicarboxylate Utilities Summary . . . . . . . . . . . . . . . . . . . .
11.6 Trans-1,4-cyclohexane Diisocyanate from Dimethyl T-cyclohexane-1,4-dicarboxylate Total Capital Investment. . . . . . . . , . . . . . . . ,
11.7 Trans-1,4-cyclohexane Diisocyanate from Dimethyl T-cyclohexane-1,4-dicarboxylate Production Costs. . . . . . . . . . . . . . . . . . . . .
13.1 Isocyanate Adducts with Biuret Structure Patentsunmary......................
13.2 Blocked Isocyanates from Aliphatic, Alicyclic, and Arylaliphatic Isocyanates Patentsummary......................
13.3 Other Adducts of Aliphatic, Alicyclic, and Arylaliphatic Isocyanates Patentsummary......................
13.4 Trimer-s or Polycondensed Products of Aliphatic, Alicyclic, or Arylaliphatic Isocyanates PatentSummary........ , . . . . . . . . . . . . .
243
244
247
249
252
254
256
259
261
273
274
276
277
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TABLES
13.5
13.6
13.7
13.8
13.9
13.10
13.11
13.12
13.13
13.14
13.15
13.16
14.1
14.2
B.l
Biuret from Hexamethylene Diisocyanate Design Bases and Assumptions. . . . . . . . . , . . . . .
Biuret from Hexamethylene Diisocyanate StreamFlows. . . . . . . . . . . . . . . . . . . . . . .
Biuret from Hexamethylene Diisocyanate MajorEquipment.....................
Biuret from Hexamethylene Diisocyanate Utilities Summary . . . . . . . . . . . . . . . . . . . .
Biuret from Hexamethylene Diisocyanate Total Capital Investment. . . . . . . . . . . . . . . . .
Biuret from Hexamethylene Diisocyanate Production Costs. , . . . . . . . . . . . . . . . . . . .
Blocked Isocyanate from Isophorone Diisocyanate Design Bases and Assumptions. . , . . , . . . . . . . . .
Blocked Isocyanate from Isophorone Diisocyanate StreamFlows. . . . . . . . . . . . . . . . . . . . . . .
Blocked Isocyanate from Isophorone Diisocyanate Major Equipment.....................
Blocked Isocyanate from Isophorone Diisocyanate Utilities Summary . . . . . . . . . . . . . . . . . . . .
Blocked Isocyanate from Isophorone Diisocyanate Total Capital Investment. . . . . . . . . . . . . . . . .
Blocked Isocyanate from Isophorone Diisocyanate Production Costs. . . . . . . . . . . . . . . . . . . . .
Other Isocyanates by Phosgenation PatentSummary......................
Other Isocyanates by Nonphosgenation Processes Patent Summary,.....................
Nonaromatic Di- and Triisocyanates Physical Properties ? . . . . . . . . . . . . . . . . . .
279
280
281
281
283
284
288
289
290
290
292
293
298
299
316
. . . xv111
