process economics program · turing processes for the following polymers are evaluated:...
TRANSCRIPT
PROCESS ECONOMICS
PROGRAM SRI INTERNATIONAL
Menlo Park, California
94025
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PROCESS ECONOMICS
PROGRAM SRI INTERNATIONAL
Menlo Park, California
94025
Abstract
Process Economics Program Report No. 86A
HIGH TEMPERATURE POLYMERS
(July 1980)
This supplementary report on high temperature polymers is an exten-
sion of the initial report (issued August 1975) that covered polyimide,
polyamide-imide, and polyphenylene oxide. In this supplement, manufac-
turing processes for the following polymers are evaluated: polysulfone,
polyethersulfone, polyphenylene sulfide, and a polyarylate made from
terephthaloyl chloride, isophthaloyl chloride, and bisphenol A. Pro-
cesses for making the monomer materials, 4,4'-dichlorodiphenyl sulfone
and terephthaloyl and isophthaloyl chloride are also evaluated.
At the present time, the market for these polymers is relatively
small, i.e., less than 10 million lb/yr in each case, and the prices are
relatively high--ranging .from about $2.40 to $8.95 per pound for base
grade products. The growth prospects for the products are not clear.
However, polyphenylene sulfide sales have grown 60%-70%/yr in recent
times.
The unique properties of these products enable them to compete in
applications where ceramics, g lass, or metals might normally be used.
These products are also being used to replace conventional plastics
in applications where upgraded performance is desired.
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0
Report No. 86A
HIGH TEMPERATURE POLYMERS
SUPPLEMENT A
by LLOYD M. ELKIN
July 1980
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
major hkdrocarbons 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
CONTENTS
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INTRODUCTION. . . . . . . . . . . . . . . . . . . . . . . 1
SUMMARY ......................
General Aspects .................. Economic Aspects. ................. Technical Aspects ................. 4,4'-Dichlorodiphenyl Sulfone .......... Polysulfone ................... Polyethersulfone. ................ Polyphenylene Sulfide .............. Terephthaloyl (or Isophthaloyl) Chloride. .... Polyarylate ...................
INDUSTRY STATUS . . . . . . . . . . ; . . . . . . . . . . 13
CHEMISTRY .....................
4,4'-Dichlorodiphenyl Sulfone ........... Polysulfone ........ , ........... Polyethersulfone. ................. Polyphenylene Sulfide ............... Terephthaloyl (or Isophthaloyl) Chloride. ... ; . Polyarylate ....................
4,4'-DICHLORODIPHENYL SULFONE FROM CHLOROBENZENE, SULFUR TRIOXIDE, AND THIONYL CHLORIDE .......
Process Review. .................. Process Description ................ Process Discussion. ................ Choice of Design Patent ............. Batch Process ................... Excess Thionyl Chloride ............. Material of Construction. ............
Cost Estimates. ..................
POLYSULFONE FROM 4,4'-DICHLORODIPHENYL SULFONE AND BISPHENOL A ....................
Review of Processes ................ Process Description ................ Process Discussion. ................
Batch Versus Continuous ............. Molecular Weight of the Polymer ......... Solvent Recovery System .............
Cost Estimates. .................. Polyphenylsulfone ......... .' .......
. . .
. . . 3
. . . 6
. . . 6
. . . 8
. . . 9
. . . 9
. . . 10
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. . . 11
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. . . 44
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. . . 45
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. . .
. . .
. . .
. . .
. . .
. . .
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3
17
23
49
49 65 76 76 76 76 76 83
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CONTENTS
7 POLYETHERSULFONE FROM 4,4'-DICHLORODIPHENYL SULFONE
Review of Processes ................... Process Description ................... Process Discussion. ................... Dioxothiolan. ..................... Polymerization. .................... Polymerization Reactor Heat Exchangers. ........ Precipitation of Potassium Chloride .......... Unaccounted for Losses. ................ Materials of Construction ...............
Cost Estimates. .....................
8 POLYPHENYLENE SULFIDE FROM p-DICHLOROBENZENE AND SODIUMSULFIDE......................
Review of Processes ......... .......... LO5 Process Description ......... .......... 121 Process Discussion. ......... .......... 130 Choice of Design Patents. ..... .......... 130
Raw Material Supply ........ .......... 131 Water Present During Polymerization .......... 131 Heat of Polymerization. ...... .......... 131
Melt Flow ............. .......... 132 Heavy Ends. ............ .......... 133 Materials of Construction ..... .......... 133
Cost Estimates. ........... .......... 133 Glass-Filled (40 wt%> Pellets ... .......... 133 Non-Glass-Filled Powder ...... .......... 134 Cost Summary and Comparison .... .......... 135
9 TEREPHTHALOYL CHLORIDE (OR ISOPHTHALOYL CHLORIDE) FROM TEREPHTHALIC ACID (OR ISOPHTHALIC ACID) AND PHOSGENE. ..
Review of Processes ................... Process Description ................... Process Discussion. ................... Choice of Design Patent ................ Overall Yields. .................... Solvent Losses. .................... Reactor Pressure. ................... Catalyst. ....................... Terephthaloyl Chloride Purification Column C-104. ... Hydrochloric Acid ................... Solidification Method .................
Cost Estimates. .....................
89 89 97 97 97 98 98 99 99 99
105
147
147 152 159 159 159 160 160 160 160 161 161 161
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CONTENTS
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10 POLYARYLATE FROM TEREPHTHALOYL CHLORIDE, ISOPHTHALOYL CHLORIDE, AND BISPHENOL A ................
Review of Processes ................... Process Description ................... Process Discussion. ................... Choice of Design Patent ................ Main Raw Materials. .................. Reaction Conditions .................. Polymer Recovery. ................... Additives ....................... Addition of Glass Fiber ................ Steam and Electricity Consumption ...........
Cost Estimates. .....................
APPENDIX A DESIGN AND COST BASIS . . . . . . . . . . . . . 191
APPENDIX B PHYSICAL PROPERTIES OF PRODUCTS . . . . . . . . 195
APPENDIX C EQUIPMENT SUPPLIERS . . . . . . . . . . . . . . 197
CITEDREFERENCES . . . . . . . . . . , . . . . . . . . . . . . 199
PATENT REFERENCES BY COMPANY . . . . . . . . . . . . . . . . . 219
167
167 175 184 184 184 184 185 185 185 186 186
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a V
ILLUSTRATIONS
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5.1
5.2
6.1
6.2
7.1
7.2
8.1
8.2
8.3
9.1
9.2
4,4'-Dichlorodiphenyl Sulfone from Chlorobenzene, Sulfur Trioxide, and Thionyl Chloride Flowsheet.....................
4,4'-Dichlorodiphenyl Sulfone from Chlorobenzene, Sulfur Trioxide, and Thionyl Chloride Effect of Operating Level and Plant Capacity on Production Cast . . . . . . . . . . . . . . . . .
Polysulfone from 4,4'-Dichlorodiphenyl Sulfone and Bisphenol A Flow sheet.....................
Polysulfone from 4,4' -Dichlorodiphenyl Sulfone and Bisphenol A Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . .
Polyethersulfone from 4,4'-Dichlorodiphenyl Sulfone Flow sheet.....................
Polyethersulfone from 4,4'-Dichlorodiphenyl Sulfone Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . .
Polyphenylene Sulfide from p-Dichlorobenzene and Sodium Sulfide Flow sheet.....................
Polyphenylene Sulfide from p-Dichlorobenzene and Sodium Sulfide (40 wt% Glass-Filled) Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . .
Polyphenylene Sulfide from p-Dichlorobenzene and Sodium Sulfide (Non-Glass-Filled) Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . .
Terephthaloyl Chloride from Terephthalic Acid and Phosgene Flow sheet.....................
Terephthaloyl Chloride from Terephthalic Acid and Phosgene Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . .
227
48
229
82
235
104
239
140
141
245
165
vii
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ILLUSTRATIONS
10.1 Polyarylate frcm Terephthaloyl Chloride, Isophthaloyl Chloride, and Bisphenol A Flow Sheet.....................
10.2 Polyarylate from Terephthaloyl Chloride, Isophthaloyl Chloride, and Bisphenol A Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . .
viii
249
190
TABLES
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2.1
2.2
3.1
3.2
5.1
5.2
5.3
5.4
5.5
5.6
6.1 Polysulfones Products and Raw Materials . . . . . . . . . . . . .
6.2 Polysulfones
6.3
Patent summary...................
Polysulfone from 4,4' -Dichlorodiphenyl Sulfone and Bisphenol A
6.4
Polysulfone, Polyethersulfone, Polyphenylene Sulfide, and Polyarylate Manufacturing/Marketing Company, Polymer Structure, Raw Materials. . . . . . . . . . . . . . . . . . . .
Polysulfone, Polyethersulfone, Polyphenylene Sulfide, and Polyarylate Summary of Estimated Costs . . . . . . . . . . . . .
Industry Status, . . . . . . . . . . . . . . . . . .
Properties (Partial List) of Some High Performance Polymer Products . . . . . . . . . . . . . . . . . .
4,4'-Dichlorodiphenyl Sulfone from Chlorobenzene, Sulfur Trioxide, and Thionyl Chloride Patent summary...................
4,4'-Dichlorodiphenyl Sulfone from Chlorobenzene, Sulfur Trioxide, and Thionyl Chloride Major Equipment and Utilities Summary. . . . . . . .
4,4'-Dichlorodiphenyl Sulfone from Chlorobenzene, Sulfur Trioxide, and Thionyl Chloride Stream Flows . . . . . . . . . . . . . . . . . . . .
4,4'-Dichlorodiphenyl Sulfone from Chlorobenzene, Sulfur Trioxide, and Thionyl Chloride Summary of Reactor Conditions. . . . . . . . . . . .
4,4'-Dichlorodiphenyl Sulfone from Chlorobenzene, Sulfur Trioxide, and Thionyl Chloride Total Capital Investment . . . . . . . . . . . . . .
4,4'-Dichlorodiphenyl Sulfone from Chlorobenzene, Sulfur Trioxide, and Thionyl Chloride Production Costs . . . . . . . . . . . . . . . . . .
Major Equipment and Utilities Summary. . . . . . . .
Polysulfone from 4,4' -Dichlorodiphenyl Sulfone and Bisphenol A Stream Flows. . . . . . . . . . . . . . . . . . . .
4
7
15
15
24
36
39
42
46
47
50
51
70
73
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6.5
6.6
6.7
7.1
7.2
7.3
7.4
7.5
8.1
8.2
8.3
8.4
8.5
TABLES
Polysulfone from 4,4'-Dichlorodiphenyl Sulfone and Bisphenol A Summary of Reactor Conditions. . . . . . . . . . . .
Polysulfone from 4,4'-Dichlorodiphenyl Sulfone and Bisphenol A Total Capital Investment . , . . . . , . , . . . . .
Polysulfone from 4,4'-Dichlorodiphenyl Sulfone and Bisphenol A Production Costs . . . . . . . . . . . . . . . . . .
Polyethersulfone from 4,4'-Dichlorodiphenyl Sulfone Major Equipment and Utilities Summary. . . . . . . .
Polyethersulfone from 4,4'-Dichlorodiphenyl Sulfone Stream Flows. . . . . . . . . . . . . . . . . . . .
Polyethersulfone from 4,4'-Dichlorodiphenyl Sulfone Summary of Polymerization Reactor Conditions . . . .
Polyethersulfone from 4,4'-Dichlorodiphenyl Sulfone Total Capital Investment . . . . . . . . . . . . . .
Polyethersulfone from 4,4'-Dichlorodiphenyl Sulfone Production Costs . . . . . . . . . . . . . . . . . .
Polyphenylene Sulfide from p-Dichlorobengene and Sodium Sulfide Patent summary...................
Polyphenylene Sulfide (Glass Filled, 40 wt%) Pellets from p-Dichlorobenzene and Sodium Sulfide Major Equipment and Utilities Summary. . . . . . . .
Polyphenylene Sulfide from p-Dichlorobenzene and Sodium Sulfide Stream Flows. . . . . . . . . . . . . . . . . . . .
Polyphenylene Sulfide from p-Dichlorobenzene and Sodium Sulfide Summary of Reactor Conditions. . . . . . . . . . . .
Polyphenylene Sulfide (Glass-Filled, 40 wt%> Pellets from p-Dichlorobenzene and Sodium Sulfide Total Capital Investment . . . . . . . . . . . . . .
X
0 75
78
80
93
95
96
100
102
106
125
128
129
136
TABLES
8.6
8.7
8.8
9.1
9.2
9.3
9.4
9.5
9.6
10.1
10.2
10.3
10.4
Polyphenylene Sulfide (Glass-Filled, 40 wt%) Pellets from p-Dichlorobenzene and Sodium Sulfide Production Costs . . . . . . . . . . . . . . . . . .
Polyphenylene Sulfide (Non-Glass-Filled) Powder from p-Dichlorobenzene and Sodium Sulfide Total Capital Investment . . . . . . . . . . . . . .
Polyphenylene Sulfide (Non-Glass-Filled) Powder from p-Dichlorobenzene and Sodium Sulfide Production Costs . . . . . . . . . . . . . . . . . .
Terephthaloyl and Isophthaloyl Chloride Manufacture Patent summary...................
Terephthaloyl Chloride from Terephthalic Acid and Phosgene Major Equipment and Utilities Summary. . . . . . . .
Terephthaloyl Chloride from Terephthalic Acid and Phosgene Stream Flows . . . . . . . . . . . . . . . . . . . .
Terephthaloyl Chloride from Terephthalic Acid and Phosgene Summary of Reactor Conditions. . . . . . . . . . . .
Terephthaloyl Chloride from Terephthalic Acid and Phosgene Total Capital Investment . . . . . . . . . . . . . .
Terephthaloyl Chloride from Terephthalic Acid and Phosgene Production Costs . . . . . . . . . . . . . . . . . .
Polyarylate from Terephthaloyl Chloride, Isophthaloyl Chloride, and Bisphenol A Patent summary...................
Other Polyarylates Patent Summary . . . . . . . . . . . . . . . . . . .
Polyarylate from Terephthaloyl Chloride, Isophthaloyl Chloride, and Bisphenol A Major Equipment and Utilities Summary. . . . . . . .
Polyarylate from Terephthaloyl Chloride, Isophthaloyl Chloride, and Bisphenol A Stream Flows . . . . . . . . . . . . . . . . . . . .
138
142
144
148
155
157
158
163
164
168
172
179
181
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10.5
10.6
10.7
TABLES
Polyarylate from Terephthaloyl Chloride, Isophthaloyl Chloride, and Bisphenol A Summary of Reactor Conditions. . . . . . . . . . . .
Polyarylate from Terephthaloyl Chloride, Isophthaloyl Chloride, and Bisphenol A Total Capital Investment . . . . . . . . . . . . . .
Polyarylate from Terephthaloyl Chloride, Isophthaloyl Chloride, and Bisphenol A Production Costs . . . . . . . . . . . . . . . . . .
183
187
188
Xii