Isocyanates, Supp. D, July 1983
PROCESS ECONOMICS PROGRAM SRI INTERNATIONAL Menlo Park, California 94025
Abstract 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 trimethylhexamethylenediisocyanate. The experimental nonaromatic isocyanates that we reviewed include 1,6,11undecane triisocyanate, lysine-ethylester triisocyanate, transcyclohexane diisocyanate, and tetramethylxylylenediisocyanate. We evaluated eight phosgenation processes and one nonphosgenation process. We also evaluated two processes which manufacture respectively an adduct of hexamethylene diisocyanate and a blocked isophorone diisocyanate.
PEP'82 YRC/CN
Isocyanates, Supp. D, July 1983
Report No. 1D
ISOCYANATES SUPPLEMENT
D
by YU-REN CHIN wlth contributions by CHIEN NIEH
0 aa m c
I
July 1983
A private report by the
PROCESS ECONOMICS PROGRAM
Menlo Park, California 94025
Isocyanates, Supp. D, July 1983
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, product, and plant for the United States and Western Europe.
ii
Isocyanates, Supp. D, July 1983
CONTENTS
1
INTRODUCTION. .......................
1
2
SUMMARY ..........................
3
General Aspects ...................... Technical Aspects ..................... Economic Aspects. .....................
3 4 5
INDUSTRY STATUS ......................
15
Markets .......................... Producers .........................
15 16
HEXAMETHYLENE DIISOCYANATE. ................
19
Chemistry ......................... Process Description .................... Phosgenation of Hexamethylenediamine. .......... Phosgene and HCl Recovery ................ Process Discussion. .................... Cost Estimates. ......................
19 21 21 23 27 27
HYDROGENATED MDI. .....................
39
Chemistry ......................... Review of Processes .................... Process Description--Manufactureof MDA .......... Cost Estimates--Manufactureof MDA. ............ Process Description--Manufactureof Hydrogenated MD1 fromMDA .......................... Hydrogenation of MDA. .................. Phosgenation of Hydrogenated MDA. ............ Recovery of Phosgene and HCl. .............. Process Discussion--Manufactureof Hydrogenated MD1 fromMDA .......................... Cost Estimates--Manufacture of Hydrogenated MD1 fromMDA ..........................
39 40 43 44
ISOPHORONE DIISOCYANATE ..................
71
Chemistry ......................... Review of Processes .................... Process Description .................... Cyanoketone Production. ................. Isophorone Diamine Production .............. Isophorone Diisocyanate Production. ........... Product Purification and Phosgene Recovery. .......
71 74 74 77 77 78 78
3
4
5
6
iii
49 49 51 52 58 58
Isocyanates, Supp. D, July 1973
CONTENTS
6
7
8
9
ISOPHORONE DIISOCYANATE (Continued) Process Discussion. . . . . . . . . . . . , . . . . . . . . Cost Estimates. . . . . . . . . . . . . . . . . . . . . . .
86 86
XYLYLENE DIISOCYANATE AND HYDROGENATED XYLYLENE DIISOCYANATE. .......................
95
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..........................
95 96 98 98 100 109 109
TRIMETHYLHEXAMETHYLENEDIISOCYANATE ............
145
Chemistry ......................... Review of Processes .................... Process Description--TMHDA from Isophorone. ........ Trimethylcyclohexanol Production. ............ Trimethyl Adiponitrile Production ............ TrimethylhexamethyleneDiamine Production ........ Process Discussion--TMHDA from Isophorone ......... Cost Estimates--TMHDA from Isophorone ........... Process Description--TMHDI from TMHDA ........... Cost Estimates--TMHDI from TMHDA. .............
145 148 148 155 155 156 162 163 170 176
DIMER DIISOCYANATE. ....................
183
Chemistry ......................... Manufacture of Dimer Amine. ................ Manufacture of Dimer Diisocyanate ............. Process Description ................... Cost Estimates. .....................
183 184 188 188 189
116 121 121 127 127 127 134 134 142 142
iv
-
Isocyanates, Supp. D, July 1983
CONTENTS
10
TRIISOCYANATES. . . . . . . . . . . . . . . . . . . . . . .
197
Chemistry . . . . . . . . . . . . . . . . . . . . , Review of Processes . . . . . . . . . . . . . . . . Process Description--1,6,11-UndecaneTriisocyanate. Production of Tetrahydroazepine . . . , . . . . . Production of Undecane Triamine . . . . . . . . . Production of Undecane Triisocyanate. . . , . . . Recovery of Lithium Hydroxide, Phosgene, and HCl. Process Discussion--1,6,11-UndecaneTriisocyanate . Cost Estimates--1,6,11-UndecaneTriisocyanate , . . Process Description--Lysine-ethylester Triisocyanate . . . . . . . . . . . . . . . , . . . Production of Lysine-8-aminoethylesterTri-HCl. . Production of Lysine-ethylester Triisocyanate . . Recovery of Solvents, Phosgene and HCl. . . . . . Process Discussion--Lysine-ethylesterTriisocyanate Cost Estimates--Lysine-ethylesterTriisocyanate . .
. . . . . . . , .
. . . . . . . . .
. . . . . . . . .
. . . . . . . . .
197 201 201 205 205 206 207 216 217
. . . . . .
. . . . . .
. . . . . .
. . . . . .
225 225 227 227 235 235
TRANS-CYCLOHEXANE-1,4-DIISOCYANATE.............
245
Chemistry ......................... Review of Processes .................... Process Description .................... Production of CHDCA ................... Production of CHDI. ................... Purification of CHDI. .................. Process Discussion. .................... Cost Estimates. ......................
245 246 248 248 250 251 257 257
12
TETRAMETRYLXYLYLENE DIISOCYANATE. . . . . . . . . . . . . .
267
13
ADDUCTS ..........................
269
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. .....................
269 272 272 275 278 278 282 282 287 287 291 291
11
V
Isocyanates, Supp. D, July 1983
CONTENTS
14
OTHER NONAROMATIC ISOCYANATES . . . . . . . . . . . . . . .
297
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
297 305 305
. . . . . .
. . . . . .
. . . . . .
. . . . . .
. . . . . .
306 307 307 308 308 309
. .
. .
. .
. .
. .
310 310
APPENDIX A--DESIGN AND COST BASIS. . . . . . . . . . . . . . . .
311
APPENDIX B--PHYSICAL PROPERTIES. . . . . . . . . . . . . . . . .
315
CITEDREFERENCES........................
317
PATENTREFERENCES BYCOMPANY.
325
. . . . . . . . . . . . . . . . .
vi
Isocyanates, Supp. D, July 1983
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........................
329
Hexamethylene Diisocyanate from Hexamethylene Diamine by Phosgenation Effect of Plant Capacity and Operating Level on Product Values of Plant A and Plant B. , . . . . . . .
37
MDA from Aniline and Formaldehyde Effect of Operating Level and Plant Capacity on Production Cost. . . . . . . . . . . . . . . . . . . .
48
Hydrogenated MD1 from MDA Flowsheet........................ Hydrogenated MD1 from MDA Effect of Operating Level and Plant Capacity on Product Value. . . . . . . . . . . . . . . . . . . . . Isophorone Diisocyanate FlowSheet........................
333
67 335
Isophorone Diisocyanate Effect of Operating Level and Plant Capacity on Production Cost. , . . . . . . . . . . . . . . . . . .
93
Xylylene Diamine from Xylene by Ammoxidation and Hydrogenation Flow Sheet. ; . . . . . . . . . . . . . . . . . . . . . .
339
Xylylene Diamine from Xylene by Ammoxidation and Hydrogenation Effect of Operating Level and Plant Capacity on Production Cost. . . . . . . . . . . . . . . . . . . .
115
Hydrogenated Xylylene Diamine from XDA Flowsheet........................
343
Hydrogenated Xylylene Diamine from Xylylene Diamine Effect of Operating Level and Plant Capacity on Production Cost. . . . . . . . . . . . . . . . . . . .
125
Xylylene Diisocyanate from Xylene Diamine by Phosgenation Flowsheet........................
345
vii
Isocyanates, Supp. D, July 1983
ILLUSTRATIONS
7.6
8.1 8.2
8.3
8.4
9.1 9.2
10.1 10.2
10.3
10.4
11.1
Xylylene Diisocyanate from Xylylene Diamine by Phosgenation Effect of Operating Level and Plant Capacity on Production Cost. . . . . . . . . . . . . . . . . . . .
141
Trimethylhexamethylene Diamine from Isophorone FlowSheet........................
347
Trimethylhexamethylene Diamine from Isophorone Effect of Operating Level and Plant Capacity on Production Cost. . . . . . . . . . . . . . . . . , . .
169
Trimethylhexamethylene Diisocyanate from TrimethylhexamethyleneDiamine FlowSheet........................
351
Trimethylhexamethylene Diisocyanate from Trimethylhexamethylene Diamine Effect of Operating Level and Plant Capacity on Production Cost. . . . . . . . . . . . . . . . . . . .
180
Dimer Diisocyanate from Dimer Amine FlowSheet........................
353
Dimer Diisocyanate from Dimer Amine Effect of Operating Level and Plant Capacity on Production Cost. . . . . . . , . . . . . . . . . . , .
196
1,6,11-Undecane Triisocyanate from Caprolactam FlowSheet.; . . . . . . . . . . . . . . . . . . . . . .
357
1,6,11-Undecane Triisocyanate from Caprolactam Effect of Operating Level and Plant Capacity on Production Cost. . . . . . . . , . . . . . . . . . . .
224
Lysine-ethylester Triisocyanate from L-Lysine Monohydrochloride FlowSheet........................
361
Lysine-ethylester Triisocyanate from L-Lysine Monohydrochloride Effect of Operating Level and Plant Capacity on Production Cost. . . . . . . . . . . . . . . . . . . .
242
Trans-1,4-cyclohexane Diisocyanate from Dimethyl-trans-cyclohexane-1,4-dicarboxylate FlowSheet........................
367
viii
Isocyanates, Supp. D, July 1983
ILLUSTRATIONS
11.2
11.3
13.1 13.2
13.3 13.4
14.1 14.2
Trans-1,4-cyclohexane Diisocyanate from Dimethyl-trans-cyclohexane-1,4-dicarboxylate Effect of Operating Level and Plant Capacity on Production Cost. . . , . . . . . . , . . . . . . . . .
264
Trans-1,4-cyclohexane Diisocyanate from Dimethyl-trans-cyclohexane-1,4-dicarboxylate Effect of DMCHD Price on Production Cost. . . . . . . . .
265
Biuret from Hexamethylene Diisocyanate Flowsheet........................
369
Biuret from Hexamethylene Diisocyanate Effect of Operating Level and Plant Capacity on Production Cost, . . . . . . . . . . . . . . . . . . .
286
Blocked Isocyanate from Isophorone DiiSOCyaMte FlowSheet........................
371
Blocked Isocyanate from Isophorone Diisocyanate Effect of Operating Level and Plant Capacity on Production Cost. . . . . . . . . . . . . . . . . . . .
295
Production Related Cost as a Function of Plant Capacity.........................
302
Product Value Related Cost as a Function of Plant Capacity.........................
303
iX
Isocyanates, Supp. D, July 1983
TABLES
2.1 2.2 2.3 2.4
2.5 3.1 4.1
4.2
4.3
4.4
4.5
4.6 4.7
4.8
Nonaromatic Di- and Triisocyanates Summary of Technical Aspects. . . . . . . . . . . . . . .
6
Three Major Nonaromatic Diisocyanates Summary of Economics. . . , . . . . . . . . . . . , . . .
10
Other Commercial Nonaromatic Diisocyanates Surmnaryof Economics. . . . . . , . . . . . . . . . . . .
11
Nonaromatic Di- or Triisocyanates in Development Stage Sunxnaryof Economics. . . , . . . . . . . . . . . . . . .
12
ED1 Biuret and Blocked IPDI Sunxnaryof Economics. . . . . . . . . . . . . . . . . . .
14
World Producers of Nonaromatic Di- or Polyisocyanates as of End-1982. . . . . . . . . . . . . .
17
Hexamethylene Diisocyanate from Hexamethylenediamine by Phosgenation Design Bases and Assumptions. . . . . . . . . . . . . . .
22
Hexamethylene Diisocyanate from Hexamethylenediamine by Phosgenation StreamFlows. . . . . . . . . . . . . . . . . . . . . . .
24
Hexamethylene Diisocyanate from Hexamethylenediamine by Phosgenation MajorEquipment.....................
25
Hexamethylene Diisocyanate from Hexamethylenediamine by Phosgenation Utilities Summary . . . . . . . . . . . . . . . . . . . .
26
Hexamethylene Diisocyanate from Hexamethylenediamine by Phosgenation Total Capital Investment. . . . . . . . . . . . . . . . .
29
HDI from HMDA by Phosgenation Using Tertiary Amine Total Capital Investment. . . . . . . . . . , . . . . . .
31
Hexamethylene DiiSOCyaMte from Hexamethylenediamine by Phosgenation Production Costs. . . . . . . . . . . . . . . . . . . . .
32
HDI from HMDA by Phosgenation Using Tertiary Amine Production Costs. . . . . . . . . . . . . . . . . . . . .
35
Xi
Isocyanates, Supp. D, July 1983
TABLES
Hydrogenated MD1 from MDA PatentSummary......................
41
MDA from Aniline and Formaldehyde Total Capital Investment. . . . . . . . . . . . . . . . .
45
MDA from Aniline and Formaldehyde Production Costs. . . . . , . . . . . . . . . . . . . . .
46
Hydrogenated MD1 from MDA Design Bases and Assumptions. . . . . . . . . . . . . . .
50
Hydrogenated MD1 from MDA StreamFlows. . . . . . . . . . . . . . . . . . . . . . .
53
Hydrogenated MD1 from MDA Major Equipment. . . . . . . . . . . . . . . . . . . . .
55
Hydrogenated MD1 from MDA Utilities Sunnnary. . . . . . . . . . . . . . . . . . . .
57
Hydrogenated MD1 from MDA Total Capital Investment. . . . . . . . . . . . . . . . .
60
Hydrogenated MD1 from ?lDA Production Costs. . . . . . . . . . . . . . . . . . . . .
62
Hydrogenated MDA from MDA Production Costs. . . . . . . . . . . . . . . . . . . . .
65
5.11 Hydrogenated MD1 from Hydrogenated MDA Production Costs. . . . . . . . . . . . . . . . . . . . .
68
5.1 5.2 5.3 5.4 5.5 5.6 5.7 5.8 5.9 5.10
Isophorone Diisocyanate PatentSummary......................
75
Isophorone Diisocyanate Design Bases and Assumptions. . . . . . . . . . . . . . .
76
Isophorone Diisocyanate StreamFlows. . . . . . . . . . . . . . . . . . . . . . .
80
Major
Isophorone DiiSOCyaMte Equipment.....................
82
Isophorone Diisocyanate Utilities Summary . . . . . . . . . . . . . . . . . . . .
85
6.6
Isophorone Diisocyanate Total Capital Investment. . . . . . . . . . . . . . . . .
88
6.7
Isophorone Diisocyanate Production Costs. . . . . . . . . . . . . . . . . . . . .
90
6.1 6.2 6.3 6.4 6.5
xii
Isocyanates, Supp. D, July 1983
7.1
XDI and H$DI from Xylene via XDA and H+DA Patent Summary. . . . . . . . . . . , , , . . . . . . . .
97
Xylylene Diamine from Xylene by Ammoxidation and Hydrogenation Design Bases and Assumptions. . . . . , . . . ......
101
Xylylene Diamine from Xylene Ammoxidation and Hydrogenation Stream Flows. . . . . . . . . . . . . . . . . ......
102
Xylylene Diamine from Xylene by Ammoxidation and Hydrogenation Major Equipment . . . . . . . . . . . . . . . ......
106
Xylylene Diamine from Xylene by Ammoxidation and Hydrogenation Utilities Summary . . . . . . . . . . . . . . ......
108
Xylylene Diamine from Xylene by Ammoxidation and Hydrogenation Total Capital Investment. . . . . . . . . . . ......
110
Xylylene Diamine from Xylene by Ammoxidation and Hydrogenation Production Costs. . . . . . . . . . . . . . . ......
112
Hydrogenated Xylylene Diamine from Xylylene Diamine Design Bases and Assumptions. . . . . . . . . ......
117
Hydrogenated Xylylene Diamine from Xylylene Diamine Stream Flows. . , . . . . . . . . . . . . . . ......
118
7.10 Hydrogenated Xylylene Diamine from Xylylene Diamine Major Equipment. . . . . . . . . . . . . . . ......
119
7.11 Hydrogenated Xylylene Diamine from Xylylene Diamine Utilities Summary . . . . . . . . . . . . . . ......
120
7.12 Hydrogenated Xylylene Diamine from Xylylene Diamine Total Capital Investment. .'. . . . . . . . . ......
122
7.13 Hydrogenated Xylylene Diamine from Xylylene Diamine Production Costs. . . . . . . . . . . . . . . ......
123
7.2
7.3
7.4
7.5
7.6
7.7
7.8
7.9
xiii
Isocyanates, Supp. D, July 1983
TABLES
7.14 Hydrogenated Xylylene Diamine from Xylylene Diamine Production Costs. . . . . . . . . . . . . . . . . . . . . 7.15
126
Xylylene Diisocyanate from Xylylene Diamine by Phosgenation Design Bases and Assumptions. . , . . . . . . . . . . . .
128
7.16 Xylylene Diisocyanate from Xylylene Diamine by Phosgenation Stream Flows. . . . . . . . . . . . . . . . . . . . . . .
130
7.17 Xylylene Diisocyanate from Xylylene Diamine by Phosgenation Major Equipment . . . . . . . . . . . . . . . . . . . . .
131
7.18 Xylylene Diisocyanate from Xylylene Diamine by Phosgenation Utilities Summary . . . . . . . . . . . . . . . . . . . .
133
7.19 Xylylene Diisocyanate from Xylylene Diamine by Phosgenation Total Capital Investment. . . . . . . . . . . . . . . . .
135
7.20 Xylylene Diisocyanate from Xylylene Diamine by Phosgenation Production Costs. . . . . . . . . . . . . . . . . . . . .
137
7.21 Xylylene Diisocyanate from Xylylene Diamine by Phosgenation Production Costs. . . . . . . . . . . . . . . . . . . . .
140
7.22 8.1 8.2 8.3 8.4 8.5
%XDI from H6XDA Cost Features . . . . . . . . . . . . . . . . . . . . . .
143
TrimethylhexamethyleneDiiSOCyaMte PatentSummary......................
150
Trimethylhexamethylene Diamine from Isophorone Design Bases and Assumptions. . . . . . . . . . . . . . .
154
TrimethylhexamethyleneDiamine from Isophorone StreamFlows. . . . . . . . . . . . . . . . . . . . . . .
157
Trimethylhexamethylene Diamine from Isophorone Major Equipment. . . . . . . . . . . . . . . . . . . . .
159
TrimethylhexamethyleneDiamine from Isophorone Utilities Summary . . . . . . . . . . . . . . . . . . . .
161
xiv
Isocyanates, Supp. D, July 1983
TABLES
8.6 8.7 8.8
8.9
TrimethylhexamethyleneDiamine from Isophorone Total Capital Investment. . . . . . . . . . . . . . . . .
164
Trimethylhexamethylene Diamine from Isophorone Production Costs. . . . . . . . . . . . . . . . . . . . .
166
TrimethylhexamethyleneDiisocyanate from TrimethylhexamethyleneDiamine Design Bases and Assumptions. . . . . . . , . . . . . . .
171
Trimethylhexamethylene Diisocyanate from TrimethylhexamethyleneDiamine StreamFlows. . . . . . . . . . . . . . . . . . . . . . .
172
8.10 Trimethylhexamethylene Diisocyanate from TrimethylhexamethyleneDiamine MajorEquipment.....................
173
8.11 TrimethylhexamethyleneDiisocyanate from TrimethylhexamethyleneDiamine Utilities Summary . . . . . . . . . . . . . . . . . . . .
175
8.12 TrimethylhexamethyleneDiisocyanate from TrimethylhexamethyleneDiamine Total Capital Investment. . . . . . . . . . . . . . . . .
177
8.13 Trimethylhexamethylene Diisocyanate from TrimethylhexamethyleneDiamine Production Costs. . . . . . . . . . . . . . . . . . . . .
178
8.14
9.1 9.2 9.3 9.4 9.5 9.6
TrimethylhexamethyleneDiisocyanate from Isophorone Production Costs. . . . . . . . . . . . . . . . . . . . .
181
Dimer Amine Manufacture from Dimer Acid Total Capital Investment. . . . . . . . . . . . . . . . .
185
Dimer Amine Manufacture from Dimer Acid Production Costs. . . . . . . . . . . . . . . . . . . . .
186
Dimer Diisocyanate from Dimer Amine Design Bases and Assumptions. , . . . . . . . . . . . . .
189
Dimer Diisocyanate from Dimer Amine StreamFlows. . . . . . . . . . . . . . . . . . . . . . .
190
Dimer Diisocyanate from Dimer Amine MajorEquipment.....................
191
Dimer Diisocyanate from Dimer Amine Utilities Sunrnary. . . . . . . . . . . . . . . . . . . .
192
xv
Isocyanates, Supp. D, July 1983
TABLES a
Dimer Diisocyanate from Dimer Amine Total Capital Investment. . . . . . . . . . . . . . . . .
193
Dimer Diisocyanate from Dimer Amine Production Costs. . . . . . . . . , . . . . . . . . . . .
194
Aliphatic Triisocyanates Patent Sunmmry. . . . . . . . . . . . . . . . . . . . . .
202
1,6,11-Undecane Triisocyanate from Caprolactam Design Bases and Assumptions. . . . . . . . . . . . . . .
204
1,6,11-Undecane Triisocyanate from Caprolactam Stream Flows. . . . . . . . . . . . . . . . . . . . . . .
209
1,6,11-Undecane Triisocyanate from Caprolactam Major Equipment . . . . . . . . . . . . . . . . . . . . .
211
1,6,11-Undecane Triisocyanate from Caprolactam Utilities Summary . . . . . . . . . . . . . . . . . . . .
215
1,6,11-Undecane Triisocyanate from Caprolactan Total Capital Investment. . . . . . . . . . . . . . . . .
218
1,6,11-Undecane Triisocyanate from Caprolactam Production Costs. . . . . . . . . . . . . . . . . . . . .
221
Lysine-ethylester Triisocyanate from L-Lysine Monohydrochloride Design Bases and Assumptions. . . . . . . . . . . . . . .
226
Lysine-ethylester Triisocyanate from L-Lysine Monohydrochloride Stream Flows. . . . . . . . . . . . . . . . . . . . . . .
229
10.10 Lysine-ethylester Triisocyanate from L-Lysine Monohydrochloride Major Equipment . . . . . . . . . . . . . . . . . . . . .
232
10.11 Lysine-ethylester Triisocyanate from L-Lysine Monohydrochloride Utilities Summary . . . . . . . . . . . . . . . . . . . .
234
10.12 Lysine-ethylester Triisocyanate from L-Lysine Monohydrochloride Total Capital Investment. . . . . . . . . . . . . . . . .
237
10613 Lysine-ethylester Triisocyanate from L-Lysine Monohydrochloride Production Costs. . . . . . . . . . . . . . . . . . . . .
239
9.7 9.8 10.1 10.2 10.3 10.4 10.5 10.6 10.7 10.8
10.9
l
l
a
l xvi
Isocyanates, Supp. D, July 1983
TABLES
10.14 L-Lysine Monohydrochloride from Cyclohexanol Economics........................
243
10.15 L-Lysine Monohydrochloride from Cyclohexanol Raw Material and Utilities Costs. . . . . . . . . . . . .
244
11.1
11.2
11.3
11.4
11.5
11.6
11.7
13.1 13.2
13.3
13.4
Trans-1,4-cyclohexane Diisocyanate from Dimethyl-trans-cyclohexane-1,4-dicarboxylate Patentsunnnary......................
247
Trans-1,4-cyclohexane Diisocyanate from Dimethyl-trans-cyclohexane-1,4-dicarboxylate Design Bases and Assumptions. . . . . . . . . . . . . . .
249
Trans-1,4-cyclohexane Diisocyanate from Dimethyl T-cyclohexane-1,4-dicarboxylate Stream Flows. . . . . . . , . . . . . . . . . . . . . , .
252
Trans-1,4-cyclohexane Diisocyanate from Dimethyl T-cyclohexane-1,4-dicarboxylate Major Equipment . . . . . . . . . . . . . . . . . . . . .
254
Trans-1,4-cyclohexane Diisocyanate from Dimethyl T-cyclohexane-1,4-dicarboxylate Utilities Summary . . . . . . . . . . . . . . . . . . . .
256
Trans-1,4-cyclohexane Diisocyanate from Dimethyl T-cyclohexane-1,4-dicarboxylate Total Capital Investment. . . . . . . . , . . . . . . . ,
259
Trans-1,4-cyclohexane Diisocyanate from Dimethyl T-cyclohexane-1,4-dicarboxylate Production Costs. . . . . . . . . . . . . . . . . . . . .
261
Isocyanate Adducts with Biuret Structure Patentsunmary......................
273
Blocked Isocyanates from Aliphatic, Alicyclic, and Arylaliphatic Isocyanates Patentsummary......................
274
Other Adducts of Aliphatic, Alicyclic, and Arylaliphatic Isocyanates Patentsummary......................
276
Trimer-sor Polycondensed Products of Aliphatic, Alicyclic, or Arylaliphatic Isocyanates PatentSummary........ , . . . . . . . . . . . . .
277
xvii
Isocyanates, Supp. D, July 1983
TABLES
Biuret from Hexamethylene Diisocyanate Design Bases and Assumptions. . . . . . . . . , . . . . .
279
Biuret from Hexamethylene Diisocyanate StreamFlows. . . . . . . . . . . . . . . . . . . . . . .
280
Biuret from Hexamethylene Diisocyanate MajorEquipment.....................
281
Biuret from Hexamethylene Diisocyanate Utilities Summary . . . . . . . . . . . . . . . . . . . .
281
Biuret from Hexamethylene Diisocyanate Total Capital Investment. . . . . . . . . . . . . . . . .
283
13.10 Biuret from Hexamethylene Diisocyanate Production Costs. , . . . . . . . . . . . . . . . . . . .
284
13.11 Blocked Isocyanate from Isophorone Diisocyanate Design Bases and Assumptions. . , . . , . . . . . . . . .
288
13.12 Blocked Isocyanate from Isophorone Diisocyanate StreamFlows. . . . . . . . . . . . . . . . . . . . . . .
289
13.13 Blocked Isocyanate from Isophorone Diisocyanate Major Equipment.....................
290
13.5 13.6 13.7 13.8 13.9
Blocked Isocyanate from Isophorone Diisocyanate Utilities Summary . . . . . . . . . . . . . . . . . . . .
290
13.15 Blocked Isocyanate from Isophorone Diisocyanate Total Capital Investment. . . . . . . . . . . . . . . . .
292
13.16 Blocked Isocyanate from Isophorone Diisocyanate Production Costs. . . . . . . . . . . . . . . . . . . . .
293
13.14
14.1 14.2 B.l
Other Isocyanates by Phosgenation PatentSummary......................
298
Other Isocyanates by Nonphosgenation Processes Patent Summary,.....................
299
Nonaromatic Di- and Triisocyanates Physical Properties ? . . . . . . . . . . . . . . . . . .
316
. ..
xv111
