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-phenylenediamineand 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-phenyleneisophthalamide),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-Phenylenediaminecan 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
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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.
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. ......................
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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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. ...............
9 3,4'-DIAMINODIPHENYL ETHER AND ARAMID MADE THEREFROM. ..
Chemistry ........................ Process Description ................... Process Discussion. ................... CostEstimates ...................... Aramid Made from 3,4'-Diaminodiphenyl Ether .......
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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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
Viii
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.....,...............