process economics program - markit · process economics program report no. 167 ......
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PROCESS ECONOMICS
PROGRAM
Abstract
SRI INTERNATIONAL
Menlo Park, California
94025
Process Economics Program Report No. 167
ARAMIDS
(August 1983)
There are two aramids (aromatic polyamides) in commercial produc- tion and one in development. The commercial ones are poly(p-phenylene terephthalamide), made from p-phenylenediamine and terephthaloyl chlo- ride, and poly(m-phenylene isophthalamide), made from m-phenylene- diamine and isophthaloyl chloride. The one in development (by Teijin) is made from terephthaloyl chloride, p-phenylenediamine, and 3,4'- diaminodiphenyl ether. Evaluated in this report are poly(p-phenylene terephthalamide) yarn (1,500 deniers/l,000 filaments), yarn of the same size made of the developmental aramid, and poly(m-phenylene isophthal- amide) staple. These are the most common grades of the respective products. For the poly(m-phenylene isophthalamide), both dry spinning and wet spinning processes are evaluated.
We conclude that the new aramid in development cannot compete in cost with poly(p-phenylene terephthalamide). The wet spinning of poly(m-phenylene isophthalamide) is less economical than the dry spin- ning.
Production of the raw materials for making these aramids is also evaluated in this report. p-Phenylenediamine can be made from aniline, p-chloronitrobenzene, or polyester waste. The process based on aniline is generally the most economical, but both the other two processes are economical under special circumstances.
Terephthaloyl chloride or isophthaloyl choride can be made from xylene (p or m, for the respective products) or from the corresponding acid. The xylene route is the more economical.
m-Phenylenediamine is made from benzene via dinitrobenzene. 3,4'- Diaminodiphenyl ether is made from m-aminophenol and p-chloronitro- benzene. These processes are also evaluated.
PEP'83 YCY/LCH
Report No. 167
I 1 A E 0 m
ARAMIDS
by YEN-CHEN YEN
with contributions by LIN CHAIO HSU
August 1963
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 hidrocarbons 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.
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CONTENTS
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1 INTRODUCTION . . . . . . . . . . . . . . . . . . . . . . . 1
2 SUMMARY .........................
Products and Producers. ................. Cost Features ...................... Brief Description of Processes. ............. p-Phenylenediamine from Aniline ............ p-Phenylenediamine from Polyester ........... Terephthaloyl Chloride from Xylene and Terephthalic Acid ................... Poly(p-phenylene terephthalamide) Yarn. ........ Poly(m-phenylene isophthalamide) Staple by Dry Spinning .................... Poly(m-phenylene isophthalamide) Staple by Wet Spinning .................... 3,4'-Diaminodiphenyl Ether. ..............
An Aramid Made from 3,4'-Diaminodiphenyl Ether, p-Phenylenediamine, and Terephthaloyl Chloride. .....
3 REVIEW OF PROCESSES ...................
Solution Polymerization of Poly(p-phenylene terephthalamide). .................... Spinning of Poly(p-phenylene terephthalamide) ...... Other p-Aramids ..................... A Nonpara Aramid--Poly(m-phenylene isophthalamide). ... Other Nonpara Aramids .................. Spinning of Nonpara Aramids ....... i ....... Other Processes for Making Aramids. ........... Applications. ......................
4 p-PHENYLENEDIAMINE. . . . . . . . . . . . . . . . . . . . 25
Chemistry and Review of Processes . . . From p-Chloronitrobenzene . . . . . . From Aniline. . . , . , . . . . . . . From Terephthalate Ester or Polyester From p-Dichlorobenzene. . . . . . . . Other Processes . . . . . . . . . . . Purification and Stabilization. . . .
A Process for Making p-Phenylenediamine p-Chloronitrobenzene. , . . . . . . . .
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17 19 20 22 22 22 23 24
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CONTENTS
4 p-PEHNYLENEDIAMINE (Continued)
A Process for Making p-Phenylenediamine from Aniline.. .................
Process Description ............ Cost Estimates. ..............
A Process for Making p-Phenylenediamine from Polyester .................. Process Description ............ Process Discussion. ............ Cost Estimates. ..............
Comparison of Processes ...........
5 TEREPBTHALOYL CHLORIDE. ...........
Chemistry and Review of Processes ...... From Xylene via 1,4-Bis(trichloromethyl)- benzene .................. From Terephthalic Acid. .......... Other Processes ..............
A Process for Making Terephthaloyl Chloride fromxylene ................. Process Description ............ Cost Estimates. ..............
A Process for Making p-Terephthaloyl Chloride from Phosgene ................
6 p-ARAMIDS ..................
Process Description ............. Process Discussion. ............. Cost Estimates. ...............
7 m-PHENYLENEDIAMINE AND ISOPHTBALOYL CHLORIDE.
m-Phenylenediamine. . . . . . . . . . . . . . Isophthaloyl Chloride . . . . . . . . . . . .
8 POLY(m-PHENYIENE IS OPHTHALAMIDE). ......
Poly(m-phenylene isophthalamide) Staple by Dry Spinning. ................ Process Description ............. Process Discussion. ............. Cost Estimates. ...............
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33 33 35
68 68 77
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89 100 102
111
111 117
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CONTENTS
8 POLY(m-PHENYLENE ISOPHTHALAMIDE) (Continued)
Poly(m-phenylene isophthalamide) Staple by Wet Spinning. . . . . . . . . . . . . . . . . . . . . . . Process Description . . . . . . . . . . . . . . . . . . . Cost Estimates. . . . . . . . . . . . . . . . . . . . . .
140 140 147
9 3,4'-DIAMINODIPHENYL ETHER AND ARAMID MADE THEREFROM. ..
Chemistry ........................ Process Description ................... Process Discussion. ................... CostEstimates ...................... Aramid Made from 3,4'-Diaminodiphenyl Ether .......
PATENT SIJMMARYTABLES. . . . . . . . . . . . . . . . . . . . . 173
CITEDREFERENCES . . . . . . . . . . . . . . . . . . . . . . . 229
PATENT REFERENCES. . . . . . . . . . . . . . . . . . . . . . . 255
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153 155 164 164 169
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4.1
4.2
4.3
4.4
5.1
5.2
6.1
6.2
6.3
7.1
7.2
8.1
ILLUSTRATIONS
p-Phenylenediamine from Aniline Flowsheet........................
p-Phenylenediamine from Aniline Effect of Operating Level and Plant Capacity on Production Cost and Product Value. . . . . . . . . . .
p-Phenylenediamine from Polyester Flowsheet........................
p-Phenylenediamine from Polyester Effect of Operating Level and Plant Capacity on Production Cost and Product Value. . . . , . . . . . .
Terephthaloyl Chloride from Xylene FlowSheet........................
Terephthaloyl Chloride from Xylene Effect of Operating Level and Plant Capacity on Production Cost and Product Value. . . . . . . . . . .
Poly(p-Phenylene Terephthalamide) Yarn Manufacture Flowsheet........................
Poly(p-Phenylene Terephthalamide) As-Spun Yarn Manufacture (Without Heat Treatment) Effect of Operating Level and Plant Capacity on Production Cost and Product Value. . . . . . . . . . .
Heat Treatment of Poly(p-Phenylene Terephthalamide) Fiber Effect of Operating Level and Plant Capacity on Incremental Production Cost and Product Value. . . . .
m-Phenylenediamine from Benzene Effect of Operating Level and Plant Capacity on Production Cost and Product Value. . . . . . . . . . .
Isophthaloyl Chloride from m-xylene Effect of Operating Level and Plant Capacity on Production Cost and Product Value. . . . . . . . . . .
Poly(m-Phenylene Isophthalamide) Staple by Dry Spinning Flowsheet........................
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126
275
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ILLUSTRATIONS
8.2 Poly(m-Phenylene Isophthalamide) Staple by Dry Spinning Effect of Operating Level and Plant Capacity on Production Cost and Product Value, . . , , , . , . , .
8.3 Poly(m-Phenylene Isophthalamide) Staple by Wet Spinning
139
FlowSheet............... . . . . . . . . . 279
9.1 3,4'-Diaminodiphenyl Ether from p-Chloronitrobenzene and m-Aminophenol Flowsheet........................ 281
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TABLES
2.1 Aramid Producers. ...................
2.2 Grades and Applications of Aramids. ..........
2.3 Cost Features of Aramids. ...............
2.4 Cost Features of p-Phenylenediamine ..........
2.5 Cost Features of Terephthaloyl Chloride . . . . . . . .
2.6 Cost Features of m-Phenylenediamine from Benzene........................
2.7 Cost Features of 3-4'-Diaminodiphenyl Ether from p-Chloronitrobenzene and m-Aminophenol . . . . . .
3.1 Solution Polymerization of p-Aramids, Mainly from p-Phenylenediamine and Terephthaloyl Chloride Patent Summary.....,...............
3.2 Spinning of p-Aramids, Mainly Poly(p-Phenylene Terephthalamide) Patent Sumnary. . . . . . . . . . . . . . . . . . . . .
3.3 p-Aramids Other than Poly(p-Phenylene Terephthalamide) Patent Summary. . . . . . . . . . . . . . . . . . . . .
3.4 Solution Polymerization of Nonpara Aramids, Mainly from m-Phenylenediamine and Isophthaloyl Chloride Patent Summary. . . . . . . . . . . . . . . . . . . . .
3.5 Nonpara Aramids Other than Poly(m-Phenylene Isophthalamide) Patent Sumnary. . . . . . . . . . . . . . . . . . . . .
3.6 Spinning of Nonpara Aramids Patent Sumnary. . . . , . . . . . . . . . . . . . . . .
3.7 Aramids Made by Processes Other than Solution Process Using Diacyl Chlorides Patent Summary. . . . . . . . . . . . . . . . . . . . .
3.8 Films Made from Aramids Patent Sununary. . . . . . . . . . . . . . . . . . . . .
3.9 Application of Aramids Patent Sumnary. . . . . . . . . . . . . . . . . . . . .
4.1 p-Phenylenediamine Manufacture Patent Sumnary. . . . . . . . . . . . . . . . . . . . .
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175
181
185
191
197
205
209
212
216
218
TABLES
4.2 p-Phenylenediamine from p-Chloronitrobenzene Total Capital Investment. . . . . . . . . . . . . . . .
4.3 p-Phenylenediamine from p-Chloronitrobenzene Production Costs. . . . . . . . . . . . . . . . . . . .
4.4 p-Phenylenediamine from Aniline Design Bases and Assumptions. , . , . . , . . , , , . ,
4.5 p-Phenylenediamine from Aniline StreamFlows. . . . . . . . . . . . . . . . . . . . . .
4.6 p-Phenylenediamine from Aniline Major Equipment . . . . . . . . . . . . . . . . . . . .
4.7 p-Phenylenediamine from Aniline Utilities Summary . . . . . . . . . . . . . . . . . . .
4.8 p-Phenylenediamine from Aniline Total Capital Investment. . . . . . . . . . . . . . . .
4.9 p-Phenylenediamine from Aniline Production Costs. . . . . . . . . . . . . . . . . . . .
4.10 p-Phenylenediamine from Polyester Design Bases and Assumptions. . . . . . . . . . . . . .
4.11 Manufacture of p-Phenylenediamine from Polyester StreamFlows. . . . . . . . . . . . . . . . . . . . . .
4.12 p-Phenylenediamine from Polyester MajorEquipment....................
4.13 p-Phenylenediamine from Polyester Utilities Summary . . . . . . . . . . . . . . . . . . .
4.14 p-Phenylenediamine from Polyester Total Capital Investment. . . . . . . . . . . . . . . .
4.15 p-Phenylenediamine from Polyester Production Costs. . . . . . . . . . . . . . . . . . . .
4.16 Cost Effect of Replacing Polyester Waste with Oligomer . . . . . . . . . . . . . . . . . . . . .
5.1 Chlorination of Xylene to CY, o!'-Hexachloroxylene with Light as Catalyst Patent Summary. . . . . . . . . . . . . . . . . . . . .
5.2 Terephthaloyl Chloride from CY, cr'-Hexachloroxylene Patent Summary. . . . . . . . . . . . . . . . . . . . .
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39
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48
50
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58
60
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224
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TABLES
5.3 Terephthaloyl Chloride from Terephthalic Acid Patent Summary. . . . . . . . . . . . . . . . . . . . .
5.4 Other Processes for Preparation of Terephthaloyl Chloride Patent Summary. . . . . . . . . . . . . . . . . . . . .
5.5
5.6
5.7
5.8
5.9
5.10
5.11
5.12
Terephthaloyl Chloride from Xylene Design Bases and Assumptions. . . . . , . . . . . . . .
Terephthaloyl Chloride from Xylene StreamFlows. . . . . . . . . . . . . . . . . . . . . .
69
71
Terephthaloyl Chloride from Xylene Major Equipment . . . . . . . . . . . . . . . . . . . .
Terephthaloyl Chloride from Xylene Utilities Summary . . . . , . . . . . . . . . . . . . .
Terephthaloyl Chloride from Xylene Total Capital Investment. . . . . . . . . . . . . . . .
Terephthaloyl Chloride from Xylene Production Costs. . . . . . . . . . . . . . . . . . . .
74
76
78
80
Terephthaloyl Chloride from Terephthalic Acid and Phosgene Total Capital Investment. . . . . . . . . . . . . . . . 84
226
228
Terephthaloyl Chloride from Terephthalic Acid and Phosgene Production Costs. . . . . . . . . . . . . . . . . . . . 86
6.1 Poly(p-Phenylenediamine Terephthalamide) Yarn Manufacture Design Bases and Assumptions. . . . . , . . . , . . . . 90
6.2 Poly(p-Phenylene Terephthalamide) Yarn Manufacture Stream Flows. . . . . . . . . . . . . , . . . . . . . . 94
6.3 Poly(p-Phenylene Terephthalamide) Yarn Manufacture Major Equipment . . . . . . . . . . . . . . . . . . . . 97
6.4 Poly(p-Phenylene Terephthalamide) Yarn Manufacture Utilities Summary . . . . . . . . . . . . . . . . . . . 99
6.5 Poly(p-Phenylene Terephthalamide) As-Spun Yarn Manufacture (Without Heat Treatment) Total Capital Investment. . . . . . . . . . . . . . . . 103
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TABLES
6.6 Poly(p-Phenylene Terephthalamide) As-Spun Yarn Manufacture (Without Heat Treatment) Production Costs. . . . . . . . . . . . . . . . . . . .
6.7 Heat Treatment of Poly(p-Phenylene Terephthalamide) Yarn Capital Investment. . . . , . , . . , . . . . . . . , .
6.8 Heat Treatment of Poly(p-Phenylene Terephthalamide) Yarn Incremental Production Costs. . . . . . . . , . . . . ,
7.1 m-Phenylenediamine .from Benzene Total Capital Investment. , . . . . . . . . . . . . . .
7.2 m-Phenylenediamine from Benzene Production Costs. . . . . . . . . . . . . . . . . . . .
7.3 Isophthaloyl Chloride from m-Xylene Total Capital Investment. . . . . . . . . . . . . . . .
7.4 Isophthaloyl Chloride from m-Xylene Production Costs. . . . . . . . . . . . . . . . . . . .
7.5 Isophthaloyl Chloride from Phosgene Total Capital Investment. . . . . . . . . . . . . . . .
7.6 Isophthaloyl Chloride from Phosgene Production Costs. . . . . . . . . . . . . . . . . . . .
8.1 Poly(m-Phenylene Isophthalamide) Staple by Dry Spinning Design Bases and Assumptions. . . . . . . . . . . . . .
8.2 Poly(m-Phenylene Isophthalamide) Staple By Dry Spinning StreamFlows. . . . . . . . . . . . . . . . . . . . . .
8.3 Poly(m-Phenylene Isophthalamide) Staple by Dry Spinning MajorEquipment....................
8.4 Poly(m-Phenylene Isophthalamide) Staple by Dry Spinning Utilities. Summary . . . . . . . . . . . . . . . . . . .
8.5 Poly(m-Phenylene Isophthalamide) Staple by Dry Spinning Total Capital Investment. . . . . . . . . . . . . . . .
105
107
108
112
114
118
120
122
124
128
131
133
134
135
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TABLES
8.6 Poly(m-Phenylene Isophthalamide) Staple Manufacture by Dry Spinning Production Costs. . . . . . . . . . . . . . . . . . . .
8.7 Poly(m-Phenylene Isophthalamide) Staple by Wet Spinning Design Bases and Assumptions. . . . . . . . . . . . . .
8.8 Poly(m-Phenylene Isophthalamide) Staple by Wet Spinning Stream Flows. . . . . . . . . . . . . . . . . . . . . .
8.9 Poly(m-Phenylene Isophthalamide) Staple Manufacture by Wet Spinning Major Equipment . . . . . . . . . . . . . . . . . . . .
8.10 Poly(m-Phenylene Isophthalamide) Staple Manufacture by Wet Spinning Utilities Summary . . . . . . . . . . . . . . . . . . .
8.11 Poly(m-Phenylene Isophthalamide) Staple Manufacture by Wet Spinning Total Capital Investment. . . . . . . . . . . . . . . .
8.12 Poly(m-Phenylene Isophthalamide) Staple Manufacture by Wet Spinning Production Costs. . . . . . . . . . . . . . . . . . . .
9.1 3,4'-Diaminodiphenyl Ether from p-Chloronitrobenzene and m-Aminophenol Design Bases and Assumptions. . . . . . . . . . . . . .
9.2 3,4'-Diaminodiphenyl Ether from p-Chloronitrobenzene and m-Aminophenol StreamFlows. . . . . . . . . . . . . . . . . . . . . .
9.3 3,4'-Diaminodiphenyl Ether from p-Chloronitrobenzene and m-Aminophenol Major Equipment . . . . . . . . . . . . . . . . . . . .
9.4 3,4'-Diaminodiphenyl Ether from p-Chloronitrobenzene and m-Aminophenol Utilities Sumnary . . . . . . . . . . . . . . . . . . .
9.5 3,4'-Diaminodiphenyl Ether from p-Chloronitrobenzene and m-Aminophenol Total Capital Investment. . . . . . . . . . . . . . . .
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141
143
145
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148
150
156
158
161
163
165
TABLES
9.6 3,4'-Diaminodiphenyl Ether from p-Chloronitrobenzene and m-Aminophenol Production Costs. . , . . . . . . . . , . . . . . . . .
9.7 Aramid from p-Phenylenediamine, Terephthaloyl Chloride & Diaminophenyl Ether Total Capital Investment, . . . . . . . . . . . . . . .
9.8 Aramid from p-Phenylenediamine, Terephthaloyl Chloride & Diaminophenyl Ether Production Costs. . . . . . . . . . . . . . . . . . . .
167
170
171
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