A novel non-phosgene polycarbonate production process using by-product CO2 as starting material

Green Chemistry

Volumn 5, Issue 5, 2003, Pages 497-507

  Fukuoka, Shinsuke ^a   Kawamura, Mamoru ^a   Komiya, Kyosuke ^a   Tojo, Masahiro ^a   Hachiya, Hiroshi ^a   Hasegawa, Kazumi ^a   Aminaka, Muneaki ^a   Okamoto, Hirosige ^a   Fukawa, Isaburo ^a   Konno, Shigenori ^a  

^a ASAHI KASEI CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4,4' ISOPROPYLIDENEDIPHENOL; CARBON DIOXIDE; CARBON MONOXIDE; CARCINOGEN; CHLORINE; COKE; DICHLOROMETHANE; ETHYLENE GLYCOL; ETHYLENE OXIDE; HYDROCARBON; OXYGEN; PHOSGENE; POLYCARBONATE;

CHEMICAL INDUSTRY; CONFERENCE PAPER; ECOLOGY; ENERGY CONSERVATION; ENVIRONMENT; TECHNOLOGY;

EID: 0345293143     PISSN: 14639262     EISSN: None     Source Type: Journal    
DOI: 10.1039/b304963a     Document Type: Conference Paper

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80. (d) Y. Sasaki, K. Komiya and S. Fukuoka, Jap. Pat., 4-54156 A1, Feb. 21, 1992; 7-91233 B2, Oct. 4, 1995, to Asahi Kasei Corp;
81. (e) Y. Sasaki, K. Komiya and S. Fukuoka, Jap. Pat., 4-103561 A1, April 6, 1992; 7-110840 B2, P2086543, Sep. 2, 1996, to Asahi Kasei Corp;
82. (f) S. Fukuoka, Y. Sasaki and M. Tojo, Jap. Pat., 4-198141 A1, July 17, 1992; P2529025, June 14, 1996, to Asahi Kasei Corp;
83. (g) S. Fukuoka, M. Tojo and Y. Sasaki, Jap. Pat., 4-230243 A1, Aug. 19, 1992; 7-68180 B2, July 26, 1995, to Asahi Kasei Corp;
84. (h) S. Fukuoka and K. Komiya, Jap. Pat., 5-78284 A1, March 30, 1993; P3016289, Dec. 24, 1999, to Asahi Kasei Corp;
85. H. Okamoto and S. Fukuoka, Jap. Pat., 6-16596 A, Jan. 25, 1994; P3214576, July 27, 2001, to Asahi Kasei Corp;
86. (j) M. Tojo, S. Fukuoka and M. Kawamura, Jap. Pat., 9-183744 A1, July 15, 1997, to Asahi Kasei Corp;
87. (k) M. Tojo, S. Fukuoka and M. Kawamura, Jap. Pat., 9-194435 A1, July 29, 1997, to Asahi Kasei Corp;
88. (l) M. Tojo, S. Fukuoka and M. Kawamura, World Pat., WO 97/23445 A1, July 3, 1997; US Pat., 5 847 189, Dec. 8, 1998, Eur. Pat., 0889025 B1, April 3, 2002, to Asahi Kasei Corp;
89. (l) M. Tojo, S. Fukuoka and M. Kawamura, World Pat., WO 97/23445 A1, July 3, 1997; US Pat., 5 847 189, Dec. 8, 1998, Eur. Pat., 0889025 B1, April 3, 2002, to Asahi Kasei Corp;
90. (m) M. Tojo, S. Fukuoka and M. Kawamura, Jap. Pat., 9-176061 A1, Dec. 28, 1995, to Asahi Kasei Corp;
91. (n) S. Kawazoe and M. Tojo, Jap. Pat., 9-221436 A1, Feb. 14, 1996, to Asahi Kasei Corp;
92. (o) M. Tojo and K. Onishi, World Pat., WO 99/64382, Dec. 16, 1999; US Pat., 6 346 638 B1, Feb. 12, 2002, to Asahi Kasei Corp;
93. (o) M. Tojo and K. Onishi, World Pat., WO 99/64382, Dec. 16, 1999; US Pat., 6 346 638 B1, Feb. 12, 2002, to Asahi Kasei Corp;
94. (p) M. Tojo, K. Onishi and K. Tomoyasu, Jap. Pat., 2002-308804 A1, Oct. 23, 2002, to Asahi Kasei Corp;
95. (q) M. Tojo and K. Onishi, US Pat., 6479689 B1, Nov. 12, 2002, to Asahi Kasei Corp.
96. (a) T. Watanabe and S. Fukuoka, Jap. Pat., 57-176932 A1, Dec. 30, 1981; 64-3181B2, Jan. 19, 1989, to Asahi Kasei Corp;
97. (b) T. Watanabe and S. Fukuoka, Jap. Pat., 57-183745 A1, May 6, 1981; 64-5588 B2, Jan. 31, 1989, to Asahi Kasei Corp;
98. (c) S. Fukuoka, R. Deguchi and M. Tojo, US Pat., 5 166 393, Nov. 24, 1992; Jap. Pat., 1-93560 A1, April 12, 1989; 5-44938 B2, July 7, 1993, to Asahi Kasei Corp;
99. (c) S. Fukuoka, R. Deguchi and M. Tojo, US Pat., 5 166 393, Nov. 24, 1992; Jap. Pat., 1-93560 A1, April 12, 1989; 5-44938 B2, July 7, 1993, to Asahi Kasei Corp;
100. (d) S. Fukuoka and R. Deguchi, Jap. Pat., 3-200746 A1, Sep. 2, 1991; 7-91230 B2, Oct. 4, 1995, to Asahi Kasei Corp;
101. (e) S. Fukuoka and R. Deguchi, Jap. Pat., 3-236354 A1, Oct. 22, 1991; 7-91231 B2, Oct. 4, 1995, to Asahi Kasei Corp;
102. (f) S. Fukuoka, M. Tojo and M. Kawamura, Jap. Pat., 3-291257 A1, Dec. 20, 1991 (Priority Dec. 28, 1989); 7-91236 B2, Oct. 4, 1995, to Asahi Kasei Corp;
103. (g) S. Fukuoka, M. Tojo and M. Kawamura, Jap. Pat., 4-9358 A1, Jan. 14, 1992 (Priority Dec. 28, 1989); 7-91235 B2, Oct. 4, 1995, to Asahi Kasei Corp;
104. (h) S. Fukuoka, M. Tojo and M. Kawamura, Jap. Pat., 4-211038 A1, Aug. 3, 1992 (Priority Feb. 21, 1990); 7-68182 B2, July 26, 1995, to Asahi Kasei Corp;
105. (i) S. Fukuoka, M. Tojo and M. Kawamura, US Pat., 5 210268, May 11, 1993; Eur. Pat., 461274 B1, June 15, 1994, to Asahi Kasei Corp;
106. (i) S. Fukuoka, M. Tojo and M. Kawamura, US Pat., 5 210268, May 11, 1993; Eur. Pat., 461274 B1, June 15, 1994, to Asahi Kasei Corp;
107. (j) S. Fukuoka, M. Tojo and M. Kawamura, Jap. Pat., 4-224547 A1, Dec. 26, 1990; 7-91234 B2, to Asahi Kasei Corp;
108. (k) S. Fukuoka, M. Tojo and M. Kawamura, Jap. Pat., 4-230242 A1, Aug. 19, 1992; 7-68179 B2, July 26, 1985, to Asahi Kasei Corp;
109. (l) S. Fukuoka, M. Tojo and M. Kawamura, Jap. Pat., 4-235951 A1, Aug. 25, 1992; 7-72158 B2, Aug. 2, 1995, to Asahi Kasei Corp;
110. (m) K. Komiya, M. Tojo and S. Fukuoka, World Pat., WO 97/11049, March 27, 1997 (Priority Sept. 22, 1995); Eur. Pat., 0 855 384 A1, July 29, 1998; US Pat., 5 872 275, to Asahi Kasei Corp;
111. (m) K. Komiya, M. Tojo and S. Fukuoka, World Pat., WO 97/11049, March 27, 1997 (Priority Sept. 22, 1995); Eur. Pat., 0 855 384 A1, July 29, 1998; US Pat., 5 872 275, to Asahi Kasei Corp;
112. (m) K. Komiya, M. Tojo and S. Fukuoka, World Pat., WO 97/11049, March 27, 1997 (Priority Sept. 22, 1995); Eur. Pat., 0 855 384 A1, July 29, 1998; US Pat., 5 872 275, to Asahi Kasei Corp;
113. (n) M. Tojo, K. Onishi and K. Komiya, Jap. Pat., 11-92429 A1, April 6, 1999; World Pat., WO 99/14183, March 25, 1999 (Priority Sept. 16, 1997); Eur. Pat., 1 016 648 A1, July 5, 2000, to Asahi Kasei Corp.
114. (n) M. Tojo, K. Onishi and K. Komiya, Jap. Pat., 11-92429 A1, April 6, 1999; World Pat., WO 99/14183, March 25, 1999 (Priority Sept. 16, 1997); Eur. Pat., 1 016 648 A1, July 5, 2000, to Asahi Kasei Corp.
115. (n) M. Tojo, K. Onishi and K. Komiya, Jap. Pat., 11-92429 A1, April 6, 1999; World Pat., WO 99/14183, March 25, 1999 (Priority Sept. 16, 1997); Eur. Pat., 1 016 648 A1, July 5, 2000, to Asahi Kasei Corp.
116. (a) I. Fukawa S. Fukuoka K. Komiya and Y. Sasaki, Jap. Pat., 3-223330, Oct. 2, 1991 (Priority March 28, 1989); P 2546724, Aug. 8, 1996;
117. (b) I. Fukawa, S. Fukuoka, K. Komiya and Y. Sasaki, US Pat., 5 204 377, Apr. 20, 1993; Eur. Pat., 0 403 657 B1, Jan. 28, 1998, to Asahi Kasei Corp;
118. (b) I. Fukawa, S. Fukuoka, K. Komiya and Y. Sasaki, US Pat., 5 204 377, Apr. 20, 1993; Eur. Pat., 0 403 657 B1, Jan. 28, 1998, to Asahi Kasei Corp;
119. (c) I. Fukawa, S. Fukuoka, K. Komiya and Y. Sasaki, US Pat., 5 214 073, May 25, 1993, to Asahi Kasei Corp;
120. (d) K. Komiya, S. Fukuoka and A. Yamaguchi, Jap. Pat., 4-72326 A1, March 6, ]y; 7-86138 B1, Sept. 20, ]y, to Asahi Kasei Corp;
121. (e) K. Komiya, Jap. Pat., 6-271659 A1, Sep. 27, ]y; P3208210, 6 July ]y, to Asahi Kasei Corp.
122. (a) I. Fukawa and T. Tanabe, Jap. Pat., 3-252421 A1, Nov. 11, ]y; 7-98862 B2 Oct. 25, ]y, to Asahi Kasei Corp;
123. (b) K. Komiya, M. Aminaka and Y. Kawakami, Jap. Pat., 8-225641 A1, Sep. 13, ]y, to Asahi Kasei Corp;
124. (c) H. Hachiya and K. Komiya, Jap. Pat., 8-231844 A1, Sept. 10, 1996; P3393167, Jan. 24, 2003, to Asahi Kasei Corp;
125. (d) K. Komiya, S. Fukuoka and Y. Kawakami, Jap. Pat., 8-325372 A1, 8-325373 A1, Nov. 10, 1996, to Asahi Kasei Corp;
126. (e) K. Komiya, Y. Kawakami and H. Okamoto, Eur. Pat., 0 710 687 B1, Nov. 11, 2001, to Asahi Kasei Corp;
127. (f) K. Komiya, Y. Kawakami and H. Okamoto, US Pat., 5 589 564, Dec. 31, 1996, to Asahi Kasei Corp;
128. (g) K. Komiya, Y. Kawakami and H. Okamoto, US Pat., 5 596 067, Jan. 21, 1997, to Asahi Kasei Corp;
129. (h) K. Komiya, K. Hasegawa and S. Fukuoka, Jap. Pat., 6-56984 A1 March 1, 1994; P3100008, Aug. 18, 2000, to Asahi Kasei Corp;
130. (i) K. Komiya, K. Hasegawa and M. Aminaka, Jap. Pat., 10-330474 A1, Dec. 15, 1998; P2989578, Oct. 8, 1999, to Asahi Kasei Corp;
131. (j) K. Komiya, S. Fukuoka and M. Kawamura, US Pat., 5 840826, Nov. 24, 1998, to Asahi Kasei Corp.
132. P. T. Anastas and J. C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, Oxford, 1998.
133. The newspapers say that new construction costs of the PC production plants are as follows: (a) Phosgene process (1) About 20 thousand million yen for 60 000 ton/year plant for "T. Co." in Singapore. Sekiyu-Kagaku-Shinbun (Japanese) [The "Petro-Chemical Press" (weekly)], Dec. 6. 1999. (2) About 20 thousand million yen for 40 000 ton/year plant for "S.D. Co." in Japan. Kagaku Kogyo Nippo (Japanese) [The Chemical Daily], Oct. 7. 1993. (b) Non-phosgene Asahi Kasei process About 9 thousand million yen for 50 000 ton/year plant for Chimei-Asahi Corp. in Taiwan. Kagaku Kogyo Nippo (Japanese) [The Chemical Daily], Nov. 8, 1999.
134. The newspapers say that new construction costs of the PC production plants are as follows: (a) Phosgene process (1) About 20 thousand million yen for 60 000 ton/year plant for "T. Co." in Singapore. Sekiyu-Kagaku-Shinbun (Japanese) [The "Petro-Chemical Press" (weekly)], Dec. 6. 1999. (2) About 20 thousand million yen for 40 000 ton/year plant for "S.D. Co." in Japan. Kagaku Kogyo Nippo (Japanese) [The Chemical Daily], Oct. 7. 1993. (b) Non-phosgene Asahi Kasei process About 9 thousand million yen for 50 000 ton/year plant for Chimei-Asahi Corp. in Taiwan. Kagaku Kogyo Nippo (Japanese) [The Chemical Daily], Nov. 8, 1999.
135. The newspapers say that new construction costs of the PC production plants are as follows: (a) Phosgene process (1) About 20 thousand million yen for 60 000 ton/year plant for "T. Co." in Singapore. Sekiyu-Kagaku-Shinbun (Japanese) [The "Petro-Chemical Press" (weekly)], Dec. 6. 1999. (2) About 20 thousand million yen for 40 000 ton/year plant for "S.D. Co." in Japan. Kagaku Kogyo Nippo (Japanese) [The Chemical Daily], Oct. 7. 1993. (b) Non-phosgene Asahi Kasei process About 9 thousand million yen for 50 000 ton/year plant for Chimei-Asahi Corp. in Taiwan. Kagaku Kogyo Nippo (Japanese) [The Chemical Daily], Nov. 8, 1999.
136. 2 and NaOH (raw materials) are wasted as NaCl. At least this point shows that the Asahi Kasei Process is more economical than the phosgene process.
137. J. Plotkin and E. Glatzer describe our process in the article "Polycarbonate", European Chemical News (ECN), July 2002/Process Review pp. 32-34 as follows (the extract is shown): "Phosgene is a toxic chemical that requires rigorous process design standards to protect the health and safety of workers. Investment requirements are increased by the need for close analytical monitoring and control, equipment designs for lethal service, and treatment of vent streams by caustic scrubbing or incineration. Toughening of environmental restrictions worldwide has added impetus to the search for non-phosgene routes to polycarbonate. In addition to phosgene concerns, the interfacial polymerization process typically uses a chlorinated solvent, methylene chloride, another material with exposure limits. A further incentive to eliminate the use of phosgene is the economic penalty incurred because the chlorine content of the phosgene is wasted and converted to sodium chloride. Caustic soda is consumed in the conversion, and the disposal of waste salt solutions presents ecological problems in itself. In a second stage reactor, the ethylene carbonate is transesterified with methanol to give two products - dimethyl carbonate and ethylene glycol. Since a large portion of ethylene oxide is normally converted to ethylene glycol for use in polyester production, this approach in essence converts methanol to dimethyl carbonate with virtually no addition raw material costs. And, as an extra bonus, selectivity to ethylene glycol is very high, avoiding diethylene glycol and triethylene glycol, which are by-products of conventional ethylene glycol processes via hydrolysis of ethylene oxide".