Green and sustainable chemistry in practice: Development and industrialization of a novel process for polycarbonate production from CO 2 without using phosgene

Polymer Journal

Volumn 39, Issue 2, 2007, Pages 91-114

  Fukuoka, Shinsuke ^a   Tojo, Masahiro ^a   Hachiya, Hiroshi ^a   Aminaka, Muneaki ^a   Hasegawa, Kazumi ^a  

^a ASAHI KASEI CORPORATION   (Japan)

Author keywords

Cl free PC; EO; High purity MEG; Polycarbonate from CO2; Realized GSC; Reduction of CO2 emissions; Without using phosgene

Indexed keywords

CARBON DIOXIDE; CARBON MONOXIDE; EMISSION CONTROL; ENERGY CONSERVATION; MONOMERS; POLYCARBONATES; TOXIC MATERIALS; WASTEWATER;

AROMATIC POLYCARBONATES (PC); MONOETHYLENE GLYCOLS (MEG); PHOSGENES; SUSTAINABLE CHEMISTRY;

PROCESS ENGINEERING;

EID: 34247142739     PISSN: 00323896     EISSN: 13490540     Source Type: Journal    
DOI: 10.1295/polymj.PJ2006140     Document Type: Review

References (186)

1. a) S. Fukuoka, Chem. Ind., 757 (1997).
2. b) Eur. Chem. News, 44 (1999).
3. c) S. Fukuoka, M. Kawamura, K. Komiya, M. Tojo, H. Hachiya, K. Hasegawa, M. Aminaka, H. Okamoto, I. Fukawa, and S. Konno, Green Chem., 5, 497 (2003).
4. d) S. Fukuoka, Kobunshi, 54, 114 (2005).
5. e) Kagaku Keizai, 52(6), 100 (2005).
6. f) S. Fukuoka, 'Green Production Technology' in "Environmental Process Engineering (Japanese)," N. Kojima and K. Sone, The Society of Chemical Engineers, Japan, Ed., Maruzen Co., Tokyo, 2006, chap. 8.
7. 2 as a Raw Material' in "Reports of Achievements in Industrialization Awarded the Okochi Memorial Prize 2005," OKOCHI MEMORIAL FOUNDATION, April 1, 2006, pp 1-15 (Japanese), p 76 (Abstract: English).
8. H. Schnell, L. Bottenbruch, and H. Crimm, Belg. Pat. 532,543 (1954); U.S. Patent 3,028,365 (1962) both assigned to Bayer AG.
9. a) H. Schnell, Angew. Chem., 68, 633 (1956).
10. b) H. Schnell, Ind. Eng. Chem., 51, 157 (1959).
11. H. Schnell, "Chemistry and Physics of Polycarbonates," Wiley-Interscience, New York, 1964.
12. D. W. Fox, Aust. Patent 221,192 (1959); U.S. Patent 3,153,008 (1964) both assigned to General Electric Co.
13. D. W. Fox and W. Christopher, "Polycarbonates," Reinhold Publishing Corp., New York, 1962.
14. V. Serini, 'Polycarbonates' in "Ullman's Encyclopedia of Industrial Chemistry, Fifth Completely Revised Edition," B. Elvers, S. Hawkins, and G. Schulz, Ed., VCH Verlagsgesellschaft mbH, Weinheim, 1992, vol. A21, p 207.
15. "Polycarbonate Resin Handbook (Japanese)," S. Honma, Ed., Nikkan Kogyo Sinbunsya, Tokyo, 1992, p 1.
16. D. Freitag, U. Grigo, P. R. Mueller, and W. Nouvertne, 'POLYCARBONATES' in "Encyclopedia of Polymer Science and Engineering," H. F. Mark, N. M. Bikales, C. G. Overberger, G. Menges, and J. I. Kroschwitz, Ed., John Wiley & Sons, New York, 1988, vol. 11, p 648, p 651.
17. P. J. Baker, 'Polymers, Polycarbonate' in "Encyclopedia of Chemical Processing and Design," J. J. Macketta and W. C. Cunningham, Ed., Marcel Dekker, Inc., New York, 1992, vol. 40, p 136, p 138.
18. J. A. King, Jr., 'Synthesis of Polycarbonates' in "Handbook of Polycarbonate Science and Technology," D. G. Legrand and J. T. Bendler, Edt., Marcel Dekker, Inc., New York, 2000, chap. 2, p 9.
19. a) J. E. Hallgren, U.S. Patent 4,096,168 (June 20, 1978) and U.S. Patent 4,201,721 (May 6, 1980), both assigned to General Electric Co.
20. b) A. J. Chalk, U.S. Patent 4,096,169 (June 20, 1978) and U.S. Patent 4,187,242 (Feb. 5, 1980), both assigned to General Electric Co.
21. a) H. Kezuka and F. Okuda, U.S. Patent 5,336,803 (Aug. 9, 1994), assigned to Idemitsu Kosan Co.
22. b) R. V. Chaudhari, A. A. Keller, S. P. Gupte, B. M. Bhanage, M. S. Qureshi, B. Moasser, E. J. Pressman, S. Sivaram, C. V. Avadhani, and S. Kanagasabapathy, U.S. Patent 6,222,002 (April 24, 2001), assigned to General Electric Co.
23. c) K. Okuyama, J. Sugiyama, R. Nagahata, M. Asai, M. Ueda, and K. Takeuchi, Macromolecules, 36, 6953 (2003).
24. D. J. Brunelle, 'POLYCARBONATES' in "Kirk-Othmer Encyclopedia of Chemical Technology, Fifth Edition," A. Seidel, Editor-in-chief, Wiley-Interscience, New Jersey, 2006, vol. 19, p 797, p 815.
25. D. J. Brunelle, 'Advances in Polycarbonate: An Overview' in ACS Symposium Series 898 "Advances in Polycarbonates," D. J. Brunelle and M. R. Korn, Ed., American Chemical Society, Washington, DC, 2005, chap. 1, p 2.
26. For example, a) J. E. Hallgren, G. M. Lucas, and R. O. Matthews, J. Organomet. Chem., 204, 135 (1981).
27. b) J. E. Hallgren and R. O. Matthews, J. Organomet. Chem., 212, 135 (1981).
28. c) J. A. King, Jr, T. E. Kraft, and G. R. Faler, U.S. Patent 5,142,086 (Aug. 25, 1992), assigned to General Electric Co.
29. d) E. J. Pressman and J. A. King, Jr, U.S. Patent 5,284,964 (Feb. 8, 1994), assigned to General Electric Co.
30. e) M. Takagi, H. Miyagi, Y. Ohgomori, and H. Iwane, U.S. Patent 5,498,789 (March 12, 1996), assigned to Mitsubishi Chemical Corp.
31. f) H.-J. Buysch, J. Dohm, C. Hesse, J. Rechner, and D. Kaufmann, U.S. Patent 5,502,232 (March 26, 1996), assigned to Bayer A.G.
32. g) E. Yishisato, World Patent WO 99/6142 (Feb. 11, 1999), assigned to Teijin Ltd.
33. h) C. Hesse, U. Notheis, and J. Rechner, World Patent WO 99/8787 (Feb. 25, 1999), assigned to Bayer A.G.
34. i) E. J. Pressman, B. F. Johnson, P. O. Moreno, and R. A. Battista, Rechner, World Patent WO 2000/040541 (July 13, 2000), assigned to General Electric Co.
35. a) S. Fukuoka, H. Ogawa, and T. Watanabe, Jap. Patent 1-165551 A1 (Dec. 22, 1987); 7-68178 B1 (July 26, 1995), assigned to Asahi Kasei Chemicals Corp.
36. b) S. Fukuoka, H. Ogawa, and T. Watanabe, Jap. Patent 8-134022 A1 (Dec. 22, 1987); P2748242 (Feb. 20, 1998), assigned to Asahi Kasei Chemicals Corp.
37. c) S. Fukuoka, Jap. Patent 4-257646 A1 (Sep. 11, 1992); 7-91237 B1 (Oct. 4, 1995), assigned to Asahi Kasei Chemicals Corp.
38. d) S. Fukuoka, Jap. Patent 4-261142 A1 (Sep. 17, 1992); 7-68181 B1 (July 26, 1995), assigned to Asahi Kasei Chemicals Corp.
39. K. Nakadai, '6.1.7 Ethylene Oxide, Ethylene Glycol' in "Petrochemical Process (Sekiyu Kagaku Purosesu in Japanese)," Japan Petroleum Institute Ed., Kodansya Scientific Co. 2001, pp 120-125.
40. a) P. P. McClellan, U.S. Patent 2,873,282 (Feb. 10, 1959), assigned to Jefferson Chemical Co.
41. b) E. Yasui and T. Shibata, Jap. Patent 38-23175 B1 (Oct. 10, 1963), assigned to Toa Gosei. Co.
42. c) A. H. Emmons, U.S. Patent 3,535,342 (Oct. 20, 1970), assigned to Dow Chemical Co.
43. d) F. Ohta and S. Tobita, Jap. Patent 48-27314 Bl (Aug. 21, 1973), assigned to Nisso Yuka Co.
44. e) A. Kato, S. Nagasawa, and T. Noro, Jap. Patent 50-14632 A1 (Feb. 15, 1975), assigned to Toa Gosei Co.
45. f) 'Ethylene Carbonate and Propylene Carbonate' in "Encyclopedia of Chemical Processing and Design," J. J. McKetta et al., Ed., Marcel Decker, Inc. 1984, Vol. 20, pp. 177-199.
46. g) M. Tojo and S. Fukuoka, Jap. Patent 3-120270 A1 (May 22, 1991); 8-32700 B1 (March 29, 1996), assigned to Asahi Kasei Chemicals Corp.
47. a) L. K. Frevel and J. A. Gilpin, U.S. Patent 3,642,858 (Feb. 15, 1972), assigned to Dow Chemical Co.
48. b) H.-J. Buysch, H. Krimm, and H. Rudolph, U.S. Patent 4,181,676 (Jan. 1, 1980), assigned to Bayer AG.
49. c) S. W. King and B. C. Ream, Eur. Patent 0 478 073 A2 (April 1, 1992), assigned to Union Carbide Chemicals & Plastics Co.
50. U. Romano and U. Melis, U.S. Patent 4,062,884 (Dec. 13, 1977), assigned to ANIC, S.p.A.
51. a) R. G. Duranleau, E. C. Y. Nieh, and J. F. Knifton, U.S. Patent 4,691,041 (Sep. 1, 1987), assigned to Texaco Inc.
52. b) J. F. Knifton and R. G. Duranleau, J. Mol. Cat., 1991, 67, 389.
53. a) S. Fukuoka, Y. Sasaki, and M. Tojo, Jap. Patent 4-198141 A1 (July 17, 1992) (Application: Nov. 29, 1990); P2529025 (June 14, 1996), assigned to Asahi Kasei Chemicals Corp.
54. b) About 8 months later, an analogous U.S. Patent was applied. H.-J. Buysch, A. Klausener, and F.-J. Mais, U.S. Patent 5,231,212 (July 27, 1993) (Foreign Application Priority: Sep. 3, 1991), assigned to Bayer AG.
55. c) M. Tojo and S. Fukuoka, Jap. Patent 63-238043 A1 (Oct. 4, 1988); 7-37422 B2 (April 26, 1995), assigned to Asahi Kasei Chemicals Corp.
56. d) H. Minoura and H. Nakajima, Jap. Patent 3-109358 A1 (May 9, 1991); P2955866 (July 23, 1999), assigned to Asahi Kasei Chemicals Corp.
57. e) M. Tojo and S. Fukuoka, Jap. Patent 4-9356 A1 (Jan. 14, 1992); 7-91232 B2 (Oct. 4, 1995), assigned to Asahi Kasei Chemicals Corp.
58. f) Y. Sasaki, K. Komiya, and S. Fukuoka, Jap. Patent 4-54156 A1 (Feb. 21, 1992); 7-91233 B2 (Oct. 4, 1995), assigned to Asahi Kasei Chemicals Corp.
59. g) Y. Sasaki, K. Komiya, and S. Fukuoka, Jap. Patent 4-103561 A1 (April 6, 1992); 7-110840 B2, P2086543 (Sep. 2, 1996), assigned to Asahi Kasei Chemicals Corp.
60. h) S. Fukuoka, Y. Sasaki, and M. Tojo, Jap. Patent 4-198141 A1 (July 17, 1992); P2529025 (June 14, 1996), assigned to Asahi Kasei Chemicals Corp.
61. i) S. Fukuoka, M. Tojo, and Y. Sasaki, Jap. Patent 4-230243 A1 (Aug. 19, 1992); 7-68180 B2 (July 26, 1995), assigned to Asahi Kasei Chemicals Corp.
62. j) S. Fukuoka and K. Komiya, Jap. Patent 5-78284 A1 (March 30, 1993); P3016289 (Dec. 24, 1999), assigned to Asahi Kasei Chemicals Corp.
63. k) H. Okamoto and S. Fukuoka, Jap. Patent 6-16596 A1 (Jan. 25, 1994); P3214576 (July 27, 2001), assigned to Asahi Kasei Chemicals Corp.
64. l) M. Tojo, S. Fukuoka, and M. Kawamura, Jap. Patent 9-183744 A1 (July 15, 1997); P3652035 (March 4, 2005), assigned to Asahi Kasei Chemicals Corp.
65. m) M. Tojo, S. Fukuoka, and M. Kawamura, Jap. Patent 9-194435 A1 (July 29,1997), assigned to Asahi Kasei Chemicals Corp.
66. n) M. Tojo, S. Fukuoka, and M. Kawamura, World Patent WO 97/23445 A1 (July 3, 1997); U.S. Patent 5.847,189 (Dec. 8, 1998), Eur. Patent 0889025 B1 (April 3, 2002), all assigned to Asahi Kasei Chemicals Corp.
67. o) M. Tojo, S. Fukuoka, and M. Kawamura, Jap. Patent 9-176061 A1 (Dec. 28, 1995), assigned to Asahi Kasei Chemicals Corp.
68. p) S. Kawazoe and M. Tojo, Jap. Patent 9-221436 A1 (Feb. 14, 1996); P3773294 (Feb. 24, 1996), assigned to Asahi Kasei Chemicals Corp.
69. q) M. Tojo and K. Onishi, World Patent WO 99/64382 (Dec. 16, 1999); U.S. Patent 6,346,638 B1 (Feb. 12, 2002), assigned to Asahi Kasei Chemicals Corp.
70. r) M. Tojo, K. Onishi, and K. Tomoyasu, Jap. Patent 2002-308804 A1 (Oct. 23, 2002), assigned to Asahi Kasei Chemicals Corp.
71. s) M. Tojo and K. Onishi, U.S. Patent 6,479,689 B1 (Nov. 12, 2002), assigned to Asahi Kasei Chemicals Corp.
72. t) M. Tojo and H. Miyaji, World Patent WO 2005/123638 (Dec. 29, 2005), assigned to Asahi Kasei Chemicals Corp.
73. a) M. M. Mauri, U. Romano, and F. Rivetti, ING. CHIM. ITAL., 21, N. 1-3, GEN-MAR, 6 (1985).
74. b) F. Rivetti, U. Romano, G. Garone, and M. Ghirardini, U.S. Patent 5,527,943 (June 18, 1996), assigned to Enichem Synthesis S.p.A.
75. c) U. Romano, R. Tessel, G. Cipriani, and L. Micucci, U.S. Patent 4,218,391 (Aug. 19, 1980), assigned to ANIC, S.p.A.
76. d) U. Romano, F. Rivetti, and N. D. Muzio, U.S. Patent 4,318,862 (Mar. 9, 1982), assigned to ANIC, S.p.A.
77. a) T. Matsuzaki, Syokubai (Catalysis), 41, 53 (1999).
78. b) M. Misono, Kagaku Keizai, 49(11), 38 (2002).
79. a) E. P. Boden, G. Kailasam, L. N. Lewis, and I. Vie Fernandez, World Patent WO 03/016256 (Feb. 27, 2003), assigned to General Electric Comp.
80. b) E. P. Boden and Vie Fernandez, World Patent WO 03/016258 (Feb. 27, 2003), assigned to General Electric Comp.
81. P. Tundo, F. Trotta, G. Moraglio, and F. Ligorati, Ind. Eng. Chem. Res., 27, 1565 (1988).
82. a) S. Fukuoka, M. Tojo, and M. Kawamura, World Patent WO 91/09832 A1 (July 11, 1991) (Priority: Dec. 28, 1989), assigned to Asahi Kasei Chemicals Corp.
83. b) S. Fukuoka, M. Tojo, and M. Kawamura, Jap. Patent 4-224547 A1 (Aug. 13, 1992); 7-91234 B2 (Oct. 4, 1995), assigned to Asahi Kasei Chemicals Corp.
84. a) G. Illuminati, U. Romano, and R. Tesei, U.S. Patent 4,182,726 (Jan. 8, 1980), assigned to Snamprogetti, S.p.A.
85. b) Y. Harano and T. Mitani, Jap. Patent 61-291545A1 (Dec. 22, 1986); 62-8091 B1 (Feb. 20, 1987), assigned to Daicel Chemical Co.
86. c) V. Mark, U.S. Patent 4,554,110 (Nov. 19, 1985), assigned to General Electric Co.
87. d) V. Mark, U.S. Patent 4,552,704 (Nov. 12, 1985), assigned to General Electric Co.
88. e) V. Mark, U.S. Patent 4,609,501 (Sep. 2, 1986), assigned to General Electric Co.
89. f) H. Krimm, H.-J. Buysch, and H. Rudolph, Eur. Patent 0 000 879 A1 (March 7, 1979), assigned to Bayer AG.
90. g) H. Krimm, H.-J. Buysch, and H. Rudolph, U.S. Patent 4,252,737 (Feb. 24, 1981), assigned to Bayer AG.
91. h) H.-J. Buysch, N. Schon, and J. Rechner, U.S. Patent 5,284,965 (Feb. 8, 1994), assigned to Bayer AG.
92. i) Y. Kiso and Y. Matsunaga, U.S. Patent 5,034,557 (July 23, 1991), assigned to Mitsui Petrochemical Ind.
93. j) T. Onoda, K. Tano, and Y. Hara, Jap. Patent 61-5467 B1 (Feb. 18, 1986), assigned to Mitsubishi Chemical Co.
94. k) E. Yoshisato and T. Yoshitomi, Jap. Patent 9-59209 A1 (March 4, 1997), assigned to Teijin Ltd.
95. J. E. Hallgren, U.S. Patent 4,410,464 (Oct. 18, 1983), assigned to General Electric Co.
96. a) N. Schon, R. Langer, and H.-J. Buysch, U.S. Patent 5,334,742 (Aug. 2, 1994) (Priority Application: Aug. 13, 1992), assigned to Bayer AG.
97. b) N. Schon, R. Langer, H.-J. Buysch, P. Wagner, and R. Langer, U.S. Patent 5,344,954 (Sep. 6, 1994) (Priority Application: Aug. 13, 1992), assigned to Bayer AG.
98. c) R. Paludetto, G. Paret, G. Donatti, and F. Rivetti, Ital. Patent 01255746 (Nov. 15, 1995) (Application April 1, 1992), assigned to Enichem Synthesis S.p.A.
99. d) F. Rivetti, R. Paludetto, and U. Romano, U.S. Patent 5,705,673 (Jan. 6, 1998), (Priority Application: Jan. 16, 1996) assigned to Enichem S.p.A.
100. e) M. H. Oyevaar, B. W. To, M. F. Doherty, and M. F. Malone, U.S. Patent 6,093,842 (July 25, 2000), assigned to General Electric Co.
101. f) M. Inaba, K. Hasegawa, and K. Sawa, Jap. Patent 9-40616 A1 (Feb. 10, 1997), assigned to Mitsubishi Chemical Co.
102. g) M. Inaba, K. Sawa, and T. Tanaka, Jap. Patent 9-59225 A1 (March 4, 1997), assigned to Mitsubishi Chemical Co.
103. h) M. Inaba, K. Sawa, and T. Tanaka, Jap. Patent 9-110805 A1 (April 28, 1997), assigned to Mitsubishi Chemical Co.
104. i) H. Tsuneki, Y. Onda, A. Moriya, and H. Yoshida, Eur. Patent 0 684 221 A1 (Nov. 29, 1995), assigned to Nippon Syokubai Co.
105. j) H. Kudoh, H. Kobayasi, T. Minami, K. Kaeruishi, K. Shimogawara, and K. Ajimura, Jap. Patent 2001-64234 A1 (March 13, 2001), assigned to Chiyoda Kako Co.
106. k) H. Kudoh, H. Kobayasi, T. Minami, K. Kaeruishi, K. Ajimura, and K. Shimogawara, Jap. Patent 2001-64235 A1 (March 13, 2001), assigned to Chiyoda Kako Co.
107. l) S. M. Bouwens and M. Vieveen, U.S. Patent 6,596,894 (July 22, 2003), assigned to General Electric Co.
108. m) S. M. Bouwens and M. Vieveen, U.S. Patent 6,596,895 (July 22, 2003), assigned to General Electric Co.
109. n) S. M. Bouwens and M. Vieveen, U.S. Patent 6,600,061 (July 29, 2003), assigned to General Electric Co.
110. a) T. Watanabe and S. Fukuoka, Jap. Patent 57-176932 A1 (Dec. 30, 1981); 64-3181B2 (Jan. 19, 1989), assigned to Asahi Kasei Chemicals Corp.
111. b) T. Watanabe and S. Fukuoka, Jap. Patent 57-183745 A1 (May 6, 1981); 64-5588 B2 (Jan. 31, 1989), assigned to Asahi Kasei Chemicals Corp.
112. c) S. Fukuoka, R. Deguchi, and M. Tojo, U.S. Patent 5,166,393 (Nov. 24, 1992); Jap. Patent 1-93560 A1 (April 12, 1989); 5-44938 B2 (July 7, 1993), assigned to Asahi Kasei Chemicals Corp.
113. d) S. Fukuoka and R. Deguchi, Jap. Patent 3-200746 A1 (Sep. 2, 1991); 7-91230 B2 (Oct. 4, 1995), assigned to Asahi Kasei Chemicals Corp.
114. e) S. Fukuoka and R. Deguchi, Jap. Patent 3-236354 A1 (Oct. 22, 1991); 7-91231 B2 (Oct. 4, 1995), assigned to Asahi Kasei Chemicals Corp.
115. f) S. Fukuoka, M. Tojo, and M. Kawamura, Jap. Patent 3-291257 A1 (Dec. 20, 1991) (Priority Dec. 28, 1989); 7-91236 B2 (Oct. 4, 1995), assigned to Asahi Kasei Chemicals Corp.
116. g) S. Fukuoka, M. Tojo, and M. Kawamura, Jap. Patent 4-9358 A1 (Jan. 14, 1992) (Priority Dec. 28, 1989); 7-91235 B2 (Oct. 4, 1995), assigned to Asahi Kasei Chemicals Corp.
117. h) S. Fukuoka, M. Tojo, and M. Kawamura, Jap. Patent 4-211038 A1 (Aug. 3, 1992) (Priority Feb. 21, 1990); 7-68182 B2 (July 26, 1995), assigned to Asahi Kasei Chemicals Corp.
118. i) S. Fukuoka, M. Tojo, and M. Kawamura, U.S. Patent 5,210,268 (May 11, 1993); Eur. Patent 461274 B1 (June 15, 1994), assigned to Asahi Kasei Chemicals Corp.
119. j) S. Fukuoka, M. Tojo, and M. Kawamura, Jap. Patent 4-224547 A1 (Dec. 26, 1990); 7-91234 B2, assigned to Asahi Kasei Chemicals Corp.
120. k) S. Fukuoka, M. Tojo, and M. Kawamura, Jap. Patent 4-230242 A1 (Aug. 19, 1992); 7-68179 B2 (July 26, 1985), assigned to Asahi Kasei Chemicals Corp.
121. l) S. Fukuoka, M. Tojo, and M. Kawamura, Jap. Patent 4-235951 A1 (Aug. 25, 1992); 7-72158 B2 (Aug. 2, 1995), assigned to Asahi Kasei Chemicals Corp.
122. m) K. Komiya, M. Tojo, and S. Fukuoka, World Patent WO 97/11049 (March 27, 1997) (Priority Sept. 22, 1995); Eur. Patent 0 855 384 A1 (July 29, 1998); U.S. Patent., 5,872,275; Jap. Patent P3204983 (June 29, 2001), assigned to Asahi Kasei Chemicals Corp.
123. n) M. Tojo, K. Onishi, and K. Komiya, Jap. Patent 11-92429 A1 (April 6, 1999); World Patent WO 99/14183 (March 25, 1999) (Priority Sept. 16, 1997); Eur. Patent 1 016 648 A1 (July 5, 2000), assigned to Asahi Kasei Chemicals Corp.
124. o) M. Tojo and H. Miyaji, World Patent WO 2005/123657 (Dec. 29, 2005), assigned to Asahi Kasei Chemicals Corp.
125. p) S. Fukuoka, H. Hachiya, and K. Matsuzaki, World Patent WO 2006/001256 (Jan. 5, 2006), assigned to Asahi Kasei Chemicals Corp.
126. q) S. Fukuoka, H. Hachiya, and K. Matsuzaki, World Patent WO 2006/001257 (Jan. 5, 2006), assigned to Asahi Kasei Chemicals Corp.
127. r) S. Fukuoka, H. Hachiya, and K. Matsuzaki, World Patent WO 2006/006566 (Jan. 19, 2006), assigned to Asahi Kasei Chemicals Corp.
128. s) S. Fukuoka, H. Hachiya, and K. Matsuzaki, World Patent WO 2006/006568 (Jan. 19, 2006), assigned to Asahi Kasei Chemicals Corp.
129. t) S. Fukuoka, H. Hachiya, and K. Matsuzaki, World Patent WO 2006/006585 (Jan. 19, 2006), assigned to Asahi Kasei Chemicals Corp.
130. u) S. Fukuoka, H. Hachiya, and K. Matsuzaki, World Patent WO 2006/006588 (Jan. 19, 2006), assigned to Asahi Kasei Chemicals Corp.
131. v) S. Fukuoka, H. Miyaji, H. Hachiya, and K. Matsuzaki, World Patent WO 2006/022294 (March 2, 2006), assigned to Asahi Kasei Chemicals Corp.
132. w) S. Fukuoka, H. Miyaji, H. Hachiya, and K. Matsuzaki, World Patent WO 2006/025424 (March 9, 2006), assigned to Asahi Kasei Chemicals Corp.
133. x) S. Fukuoka, H. Miyaji, H. Hachiya, and K. Matsuzaki, World Patent WO 2006/025478 (March 9, 2006), assigned to Asahi Kasei Chemicals Corp.
134. y) S. Fukuoka, H. Miyaji, H. Hachiya, and K. Matsuzaki, World Patent WO 2006/030724 (March 23, 2006), assigned to Asahi Kasei Chemicals Corp.
135. z) S. Fukuoka, H. Miyaji, H. Hachiya, and K. Matsuzaki, World Patent WO 2006/033288 (March 30, 2006), assigned to Asahi Kasei Chemicals Corp.
136. aa) S. Fukuoka, H. Miyaji, H. Hachiya, and K. Matsuzaki, World Patent WO 2006/0233291 (March 30, 2006), assigned to Asahi Kasei Chemicals Corp.
137. bb) S. Fukuoka, H. Miyaji, H. Hachiya, and K. Matsuzaki, World Patent WO 2006/035642 (April 6, 2006), assigned to Asahi Kasei Chemicals Corp.
138. cc) S. Fukuoka, H. Miyaji, H. Hachiya, and K. Matsuzaki, World Patent WO 2006/041025 (April 20, 2006), assigned to Asahi Kasei Chemicals Corp.
139. dd) S. Fukuoka, H. Miyaji, H. Hachiya, and K. Matsuzaki, World Patent WO 2006/043491 (April 27, 2006), assigned to Asahi Kasei Chemicals Corp.
140. K. Komiya, S. Fukuoka, M. Aminaka, K. Hasegawa, H. Hachiya, H. Okamoto, T. Watanabe, H. Yoneda, I. Fukawa, and T. Dozono, 'New Process for Producing Polycarbonate Without Phosgene and Methylene Chloride' in "Green Chemistry Designing Chemistry for the Environment," ACS Symposium Series 626, P. Anastas and T. C. Williamson, Ed., American Chemical Society, Washington, DC, 1996, chap. 2.
141. a) P. J. Flory, U.S. Patent 2,172,374 (Sep. 12, 1939), assigned to E. I. DuPont Co.
142. b) H. J. Hagemeyer, Jr., U.S. Patent 3,043,808 (July 10, 1962), assigned to Eastman Kodak Co.
143. a) S. Fukuoka, T. Watanabe, and T. Dozono, Jap. Patent 1-158033 A1 (June 21, 1989) (Priority Sept. 28, 1987); 7-94546 B2 (Oct. 11, 1995); World Patent WO 89/02904 (April 6, 1989); U.S. Patent 4,948,871 (Aug. 14, 1990); Eur. Pat 0 338 085 B1 (June 22, 1994), assigned to Asahi Kasei Corp.
144. b) I. Fukawa, S. Fukuoka, K. Komiya, and Y. Sasaki, Jap. Patent 3-223330 (Oct. 2, 1991) (Priority March 28, 1989); P2546724 (Aug. 8, 1996).
145. c) I. Fukawa, S. Fukuoka, K. Komiya, and Y. Sasaki, U.S. Patent 5,204,377 (Apr. 20, 1993); Eur. Patent 0403 657 B1 (Jan. 28, 1998), to Asahi Kasei Corp.
146. d) I. Fukawa, S. Fukuoka, K. Komiya, and Y. Sasaki, U.S. Patent 5,214,073 (May 25, 1993), to Asahi Kasei Corp.
147. e) K. Komiya, S. Fukuoka, and A. Yamaguchi, Jap. Patent 4-72326 A1 (March 6, 1992); 7-86138 B1 (Sept. 20, 1995), to Asahi Kasei Corp.
148. f) K. Komiya, Jap. Patent 6-271659 A1 (Sep. 27, 1994); P3208210 (July 6, 2001), to Asahi Kasei Corp.
149. a) S. Sivaram, J. C. Sehra, V. S. Iyer, and K. Ravindranath, U.S. Patent 5,266,659 (Nov. 30, 1993); S. Sivaram and S. B. Halt, Eur. Patent 0 801 089 A1 (Oct. 15, 1997), and Eur. Patent 0 9080 483 A1 (April 14, 1999), all assigned to Council of Scientific & Industrial Research, India.
150. b) B. B. Idage, S. Sivaram, G. S. Varadarajan, and J. A. King, Jr., U.S. Patent 5,717,056 (Feb. 10, 1998) and U.S. Patent 5,905,135 (May 18, 1999), Eur. Patent 0 949 288 A1 (Oct. 13, 1999); S. Sivaram and S. B. Halt, U.S. Patent 5,710,238 (Jan. 20, 1998), all assigned to General Electric Co.
151. c) R. Hisanishi and M. Okamura, Jap. Patent 6-228299 A1 (Aug. 16, 1994); S. Kuze, K. Tanaka, A. Shishikura, and R. Hisanishi, Jap. Patent 9-235368 A1 (Sep. 9, 1997); S. Kuze and K. Tanaka, Jap. Patent 10-7785 A1 (Jan. 13, 1998); S. Kuze, M. Ito, and Y. Ishikawa, Jap. Patent 10-130384 A1 (May 19, 1998); M. Ito, Jap. Patent 11-217430 (Aug. 10, 1999); Jap. Patent 11-236444 A1 (Aug. 31, 1999); M. Ito, World Patent WO 99/26995 A1 (June 3, 1999); M. Okamoto and M. Ito, World Patent WO 99/36458 A1 (July 22, 1999); M. Ito and S. Kuze, World Patent WO 99/48947 A1 (Sep. 30, 1999); M. Ito, Jap. Pat., 2001-247671 A1 (Sep. 11, 2001), 2002-155162 A1 (May 28, 2002) and 2002-220456 A1 (Aug. 9, 2002); M. Ito and A. Shishikura, Jap. Patent 2002-241484 A1 (Aug. 28, 2002), all assigned to Idemitsu Petrochemical Co.
152. d) M. G. Ormand and S. Munjal, U.S. Patent 5,864,006 (Jan. 26, 1999), assigned to Dow Chemical Co.
153. e) K. Matsumoto, Jap. Patent 6-322097 A1 (Nov. 22, 1994); T. Sakurai and N. Kido, Jap. Patent 2001-247670 A1 and 2001-247672 A1 (Sep. 11, 2001), all assigned to Teijin Ltd.
154. f) V. S. Iyer, J. C. Sehra, K. Ravindranath, and S. Sivararam, Macromolecules, 26, 1186 (1993).
155. g) S. M. Gross, G. W. Roberts, D. J. Kiserow, and J. M. DeSimone, Macromolecules, 34, 3916 (2001).
156. a) K. Tominari, A. Kanazawa, and Y. Shigeta, Jap. Patent 2-153923 A1; 2-153924 A1; 2-153925 A1; 2-193926 A1; and 2-193927 A1 (all June 13, 1990), all assigned to GE Plastics Japan Co.
157. b) M. Kimura, H. Nakano, M. Nakajima, and K. Hayashi, Jap. Patent 2000-159879 A1 and 2000-159880 A1 (all June 13, 2000), all assigned to Mitsubishi Chemical Co. and Mitsubishi Gas Chemical Co.
158. c) T. Tayama, M. Kawai, K. Hayashi, and T. Kawakami, Jap. Patent 2000-178354 A1 (June 27, 2000), assigned to Mitsubishi Chemical Co. and Mitsubishi Gas Chemical Co.
159. a) I. Fukawa and T. Tanabe, Jap. Patent 3-252421 A1 (Nov. 11, 1991); 7-98862 B2 (Oct. 25, 1995), assigned to Asahi Kasei Chemicals Corp.
160. b) K. Komiya, M. Aminaka, and Y. Kawakami, Jap. Patent 8-225641 A1 (Sep. 13, 1996), assigned to Asahi Kasei Chemicals Corp.
161. c) H. Hachiya and K. Komiya, Jap. Patent 8-231844 A1 (Sept. 10, 1996); P3393167 (Jan. 24, 2003), assigned to Asahi Kasei Chemicals Corp.
162. d) K. Komiya, S. Fukuoka, and Y. Kawakami, Jap. Patent 8-325372 A1, 8-325373 A1 (Nov. 10, 1996), assigned to Asahi Kasei Chemicals Corp.
163. e) K. Komiya, Y. Kawakami, and H. Okamoto, Eur. Patent 0 710 687 B1 (Nov. 11, 2001), assigned to Asahi Kasei Chemicals Corp.
164. f) K. Komiya, Y. Kawakami, and H. Okamoto, U.S. Patent 5,589,564 (Dec. 31, 1996), assigned to Asahi Kasei Chemicals Corp.
165. g) K. Komiya, Y. Kawakami, and H. Okamoto, U.S. Patent 5,596,067 (Jan. 21, 1997), assigned to Asahi Kasei Chemicals Corp.
166. h) K. Komiya, K. Hasegawa, and S. Fukuoka, Jap. Patent 6-56984 A1 (March 1, 1994); P3100008 (Aug. 18, 2000), assigned to Asahi Kasei Chemicals Corp.
167. i) K. Komiya, K. Hasegawa, and M. Aminaka, Jap. Patent 10-330474 A1 (Dec. 15, 1998); P2989578 (Oct. 8, 1999), assigned to Asahi Kasei Chemicals Corp.
168. j) K. Komiya, S. Fukuoka, and M. Kawamura, Jap. Patent P3202993 (June 22, 2001); World Patent WO 97/22650 (June 26, 1997); U.S. Patent 5,840,826 (Nov. 24, 1998); Eur. Pat 0 867 459 B1 (March 10, 2004), assigned to Asahi Kasei Chemicals Corp.
169. k) K. Komiya and S. Fukuoka, Jap. Patent 9-255772 (Sep. 30, 1997): P3724905 (Sep. 30, 2005); U.S. Patent 5,747,609 (May 5, 1998); Eur. Pat 0 892 001 B1 (Aug. 7, 2002), assigned to Asahi Kasei Chemicals Corp.
170. l) K. Komiya and S. Fukuoka, Jap. Patent U.S. Patent 6,429,276 (Aug. 6, 2002); Eur. Pat 1 048 685 B1 (Dec. 14, 2005), assigned to Asahi Kasei Chemicals Corp.
171. m) K. Komiya, S. Fukuoka, M. Aminaka, and K. Hasegawa, Jap. Patent P3577695 (July 23, 2004); U.S. Patent 6,320,015 (Nov. 20, 2001); Eur. Pat 1 095 957 B1 (June 16, 2004), assigned to Asahi Kasei Chemicals Corp.
172. n) S. Fukuoka, H. Hachiya, and K. Matsuzaki, World Pat WO 2005/121210 (Dec. 22, 2005), assigned to Asahi Kasei Chemicals Corp.
173. o) S. Fukuoka, H. Hachiya, and K. Matsuzaki, World Patent WO 2005/121211 (Dec. 22, 2005), assigned to Asahi Kasei Chemicals Corp.
174. p) S. Fukuoka, H. Hachiya, and K. Matsuzaki, World Patent WO 2005/123805 (Dec. 29, 2005), assigned to Asahi Kasei Chemicals Corp.
175. q) S. Fukuoka, H. Hachiya, and K. Matsuzaki, World Patent WO 2006/064656 (June 22, 2006), assigned to Asahi Kasei Chemicals Corp.
176. r) S. Fukuoka, H. Hachiya, and K. Matsuzaki, World Patent WO 2006/064664 (June 22, 2006), assigned to Asahi Kasei Chemicals Corp.
177. s) S. Fukuoka, H. Hachiya, and K. Matsuzaki, World Patent WO 2006/064667 (June 22, 2006), assigned to Asahi Kasei Chemicals Corp.
178. t) S. Fukuoka, H. Hachiya, and K. Matsuzaki, World Patent WO 2006/067993 (June 29, 2006), assigned to Asahi Kasei Chemicals Corp.
179. u) S. Fukuoka, H. Hachiya, and K. Matsuzaki, World Patent WO 2006/067994 (June 29, 2006), assigned to Asahi Kasei Chemicals Corp.
180. P. T. Anastas and J. C. Warner, "Green Chemistry: Theory and Practice," Oxford University Press, Oxford, 1998.
181. The newspapers say that the construction costs of the PC production new plants are as follows: (a) Phosgene process
182. (i) About 20 thousand million yen (¥) for 60,000 ton/year plant of "T. Co." in Singapore. Sekiyu-Kagaku-Shinbun (Japanese) [The "Petro-Chemical Press" (weekly)], Dec. 6, 1999.
183. (ii) About 20 thousand million ¥ for 40,000 ton/year plant of "S.D. Co." in Japan. Kagaku Kogyo Nippo (Japanese) [The Chemical Daily], Oct. 7, 1993.
184. (b) Non-phosgene Asahi Kasei process About 9 thousand million yen (¥) for 50,000 ton/year plant of Chimei-Asahi Corp. in Taiwan. Kagaku Kogyo Nippo (Japanese) [The Chemical Daily], Nov. 8, 1999.
185. 2 and NaOH (raw materials) are wasted as NaCl. At least this point shows that Asahi Kasei Process is more economical than the phosgene process.
186. European Chemical News (ECN) describes our process in the article of Polycarbonate" July 2002/Process Review pp. 32-34, the extraction is as follows: "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."