A Green Copolymerization of Carbon Dioxide and Propylene Oxide

Ree M; Bae JY; Jung JH; Shin TJ

Korea Polymer Journal, Vol.7, No.6, 333-349, December, 1999

Propylene oxide (PO) was used as solvent for its copolymerization with CQ₂ using zinc glutarate catalyst, producing high molecular weight polycarbonate in an exceptionally high yield never achieved before. Both the PO used as solvent and the excessive CO₂ are fully recoverable, respectively, and re-usable for the next batches of their copolymerization, indicating that this is a clean, green polymerization process to fix CO₂ into the polycarbonate. The product yield was further improved in the large-scaled copolymerization. Zinc glutarate was prepared through several synthetic routes and, however, one from zinc oxide exhibited the highest catalytic activity in the copolymerization.

[References]

Santer BD, Taylor KE, Wigley TM, Johns TC, Jones PD, Karoly DJ, Mitchell JF, Oort AH, Penner JE, Ramaswamy V, Schwarzkopf MD, Stouffer RJ, Tett S, Nature, 382(6586), 39 (1996)
Kacholia K, Reck RA, Climate Change, 35, 53 (1997)
Hanschild M, Wenzel H, Environmental Assessment of Products, Chapman & Hall, London, vol. 2 (1997)
Hill JW, Kolb DK, Chemistry for Changing Times, 7th Ed., Prentice Hall, Englewood, NJ (1995)
Houghton JT, Callander BA, Varney SK, Climate Change 1992: The Supplementary Report to the IPCC Scientific Assessment, Cambridge Univ., Cambridge (1992)
Lee YB, Choi JH, J. Korean Ind. Eng. Chem., 7(5), 813 (1996)
Paul J, Pradier CM, Carbon Dioxide Chemistry: Environmental Issues, Royal Soc. Chem., Cambridge (1994)
Hanisch C, Environ. Sci. Technol., 32, 20A (1998)
Inoue S, Koinuma H, Tsuruda T, Makromol. Chem., 130, 210 (1969)
Inoue S, Koinuma H, Tsuruda T, Polym. Lett., 7, 287 (1969)
Inoue S, Kobayashi M, Koinuma H, Tsuruta T, Makromol. Chem., 155, 61 (1972)
Soga K, Imai E, Hattori I, Polym. J., 13, 407 (1981)
Kuran W, Pasynkiewicz S, Skupinska J, Rokicki A, Makromol. Chem., 177, 11 (1976)
Kuran W, Pasynkiewicz S, Skupinska J, Makromol. Chem., 178, 2149 (1977)
Rokicki A, Kuran W, Makromol. Chem., 180, 2153 (1979)
Gorecki P, Kuran W, J. Polym. Sci. C: Polym. Lett., 23, 299 (1985)
Kuran W, Listos T, Macromol. Chem. Phys., 195, 977 (1994)
Kobayashi M, Inoue S, Tsuruda T, Macromolecules, 4, 658 (1971)
Kuran W, Rokicki A, Wilinska E, Makromol. Chem., 180, 361 (1979)
Hino Y, Yoshida Y, Inoue S, Polym. J., 16, 159 (1984)
Kobayashi M, Tang YL, Tsuruda T, Inoue S, Makromol. Chem., 169, 69 (1973)
Kuran W, Pasynkiewicz S, Skupinska J, Makromol. Chem., 177, 1283 (1976)
Shoji A, Watanabe T, Yoshida Y, Ishihara K, Koinuma H, Copolymerization of Carbon Dioxide and Epoxide with the Catalyst System of Diethyl Zinc and Fullerol, Faculty of Engineering, Toyo Univ., Kawagoe, Saitama 350 Japan
Kobayashi M, Inoue S, TsurutaT, J. Polym. Sci. A: Polym. Chem., 11, 2383 (1973)
Nishimura M, Kasai M, Tsuchida E, Makromol. Chem., 179, 1913 (1978)
Tsuchida E, Kasai M, Makromol. Chem., 181, 1612 (1980)
Chen LB, Chen HS, Lin J, J. Macromol. Sci.-Chem., A24, 253 (1987)
Soga K, Hyakkoku K, Izumi K, Ikeda S, J. Polym. Sci. A: Polym. Chem., 16, 2383 (1978)
Listos T, Kuran W, Siwiec R, J. Macromol. Sci.-Pure Appl. Chem., A32, 393 (1995)
Santangelo JG, Weber JJ, Sinclair RG, U.S. Patent, 4,665,136 (1987)
Yoshida YY, Ishihara K, Iwamoto A, Tokiwa Y, Synthesis of Carbon Dioxide-epoxide Copolymers and Their Biodegradability, presented at 1995 International Chemical Congress of Pacific Basin Societies, Dec. 17-22, Honolulu, Hawaii, U.S.A. (1995)
Kaneko Y, Saito M, Yoshida Y, Ishihara K, Synthesis and the Properties of Carbon Dioxide-Epoxide Copolymer, Presented at 1995 International Chemical Congress of Pacific Basin Societies, Dec. 17-22, Honolulu, Hawaii, U.S.A. (1995)
Inoue S, Prog. Polym. Sci. Jpn., 8, 1 (1982)
Soga K, Uenishi K, Ikeda S, J. Polym. Sci. A: Polym. Chem., 17, 415 (1979)
Motika SA, Pickering TL, Rokicki A, Stein K, U.S. Patent, 5,026,676 (1991)
Soga K, Hyakkoku K, Ikeda S, Makromol. Chem., 179, 2837 (1978)
Rokicki A, U.S. Patent, 4,943,677 (1990)
Kawachi H, Minami S, Armor JN, Rokicki A, Stein BK, U.S. Patent, 4,981,948 (1991)
Darensbourg DJ, Stafford NW, Katsurao T, J. Mol. Catal., 104, L1 (1995)
Kruper WJ, Swart DJ, U.S. Patent, 4,500,704 (1985)
Darensbourg DJ, Holtcamp MW, Macromolecules, 28(22), 7577 (1995)
Koinuma H, Hirai H, Makromol. Chem., 178, 1283 (1977)
Aida T, Ishikawa M, Inoue S, Macromolecules, 19, 8 (1986)
Inoue S, J. Macromol. Sci.-Chem., A25, 571 (1988)
Aida T, Maekawa Y, Asano S, Inoue S, Macromolecules, 21, 1195 (1988)
Soga K, Uenishi K, Hosoda S, Ikeda S, Makromol. Chem., 178, 893 (1977)
Kambe M, Takada T, Miyazaki N, Yokokawa M, U.S. Patent, 4,166,898 (1979)
Chen X, Shen Z, Zhang Y, Macromolecules, 24, 5305 (1991)
Tan CS, Hsu TJ, Macromolecules, 30(11), 3147 (1997)
Ree M, Nunes TL, Lin JS, Polymer, 35(6), 1148 (1994)
Scherrer S, Nachr. Gottinger Gesell, 2, 98 (1918)
Rokicki A, Kuran W, J. Macromol. Sci.-Rev. Macromol. Chem. Phys., C21, 135 (1981)
Dreveni I, Berkesi O, Janovics I, Andor JA, Vibrational Spectr., 2, 205 (1991)

[Referenced By]

[1] Santer BD, Taylor KE, Wigley TM, Johns TC, Jones PD, Karoly DJ, Mitchell JF, Oort AH, Penner JE, Ramaswamy V, Schwarzkopf MD, Stouffer RJ, Tett S, Nature, 382(6586), 39 (1996)

[2] Kacholia K, Reck RA, Climate Change, 35, 53 (1997)

[3] Hanschild M, Wenzel H, Environmental Assessment of Products, Chapman & Hall, London, vol. 2 (1997)

[4] Hill JW, Kolb DK, Chemistry for Changing Times, 7th Ed., Prentice Hall, Englewood, NJ (1995)

[5] Houghton JT, Callander BA, Varney SK, Climate Change 1992: The Supplementary Report to the IPCC Scientific Assessment, Cambridge Univ., Cambridge (1992)

[6] Lee YB, Choi JH, J. Korean Ind. Eng. Chem., 7(5), 813 (1996)

[7] Paul J, Pradier CM, Carbon Dioxide Chemistry: Environmental Issues, Royal Soc. Chem., Cambridge (1994)

[8] Hanisch C, Environ. Sci. Technol., 32, 20A (1998)

[9] Inoue S, Koinuma H, Tsuruda T, Makromol. Chem., 130, 210 (1969)

[10] Inoue S, Koinuma H, Tsuruda T, Polym. Lett., 7, 287 (1969)

[11] Inoue S, Kobayashi M, Koinuma H, Tsuruta T, Makromol. Chem., 155, 61 (1972)

[12] Soga K, Imai E, Hattori I, Polym. J., 13, 407 (1981)

[13] Kuran W, Pasynkiewicz S, Skupinska J, Rokicki A, Makromol. Chem., 177, 11 (1976)

[14] Kuran W, Pasynkiewicz S, Skupinska J, Makromol. Chem., 178, 2149 (1977)

[15] Rokicki A, Kuran W, Makromol. Chem., 180, 2153 (1979)

[16] Gorecki P, Kuran W, J. Polym. Sci. C: Polym. Lett., 23, 299 (1985)

[17] Kuran W, Listos T, Macromol. Chem. Phys., 195, 977 (1994)

[18] Kobayashi M, Inoue S, Tsuruda T, Macromolecules, 4, 658 (1971)

[19] Kuran W, Rokicki A, Wilinska E, Makromol. Chem., 180, 361 (1979)

[20] Hino Y, Yoshida Y, Inoue S, Polym. J., 16, 159 (1984)

[21] Kobayashi M, Tang YL, Tsuruda T, Inoue S, Makromol. Chem., 169, 69 (1973)

[22] Kuran W, Pasynkiewicz S, Skupinska J, Makromol. Chem., 177, 1283 (1976)

[23] Shoji A, Watanabe T, Yoshida Y, Ishihara K, Koinuma H, Copolymerization of Carbon Dioxide and Epoxide with the Catalyst System of Diethyl Zinc and Fullerol, Faculty of Engineering, Toyo Univ., Kawagoe, Saitama 350 Japan

[24] Kobayashi M, Inoue S, TsurutaT, J. Polym. Sci. A: Polym. Chem., 11, 2383 (1973)

[25] Nishimura M, Kasai M, Tsuchida E, Makromol. Chem., 179, 1913 (1978)

[26] Tsuchida E, Kasai M, Makromol. Chem., 181, 1612 (1980)

[27] Chen LB, Chen HS, Lin J, J. Macromol. Sci.-Chem., A24, 253 (1987)

[28] Soga K, Hyakkoku K, Izumi K, Ikeda S, J. Polym. Sci. A: Polym. Chem., 16, 2383 (1978)

[29] Listos T, Kuran W, Siwiec R, J. Macromol. Sci.-Pure Appl. Chem., A32, 393 (1995)

[30] Santangelo JG, Weber JJ, Sinclair RG, U.S. Patent, 4,665,136 (1987)

[31] Yoshida YY, Ishihara K, Iwamoto A, Tokiwa Y, Synthesis of Carbon Dioxide-epoxide Copolymers and Their Biodegradability, presented at 1995 International Chemical Congress of Pacific Basin Societies, Dec. 17-22, Honolulu, Hawaii, U.S.A. (1995)

[32] Kaneko Y, Saito M, Yoshida Y, Ishihara K, Synthesis and the Properties of Carbon Dioxide-Epoxide Copolymer, Presented at 1995 International Chemical Congress of Pacific Basin Societies, Dec. 17-22, Honolulu, Hawaii, U.S.A. (1995)

[33] Inoue S, Prog. Polym. Sci. Jpn., 8, 1 (1982)

[34] Soga K, Uenishi K, Ikeda S, J. Polym. Sci. A: Polym. Chem., 17, 415 (1979)

[35] Motika SA, Pickering TL, Rokicki A, Stein K, U.S. Patent, 5,026,676 (1991)

[36] Soga K, Hyakkoku K, Ikeda S, Makromol. Chem., 179, 2837 (1978)

[37] Rokicki A, U.S. Patent, 4,943,677 (1990)

[38] Kawachi H, Minami S, Armor JN, Rokicki A, Stein BK, U.S. Patent, 4,981,948 (1991)

[39] Darensbourg DJ, Stafford NW, Katsurao T, J. Mol. Catal., 104, L1 (1995)

[40] Kruper WJ, Swart DJ, U.S. Patent, 4,500,704 (1985)

[41] Darensbourg DJ, Holtcamp MW, Macromolecules, 28(22), 7577 (1995)

[42] Koinuma H, Hirai H, Makromol. Chem., 178, 1283 (1977)

[43] Aida T, Ishikawa M, Inoue S, Macromolecules, 19, 8 (1986)

[44] Inoue S, J. Macromol. Sci.-Chem., A25, 571 (1988)

[45] Aida T, Maekawa Y, Asano S, Inoue S, Macromolecules, 21, 1195 (1988)

[46] Soga K, Uenishi K, Hosoda S, Ikeda S, Makromol. Chem., 178, 893 (1977)

[47] Kambe M, Takada T, Miyazaki N, Yokokawa M, U.S. Patent, 4,166,898 (1979)

[48] Chen X, Shen Z, Zhang Y, Macromolecules, 24, 5305 (1991)

[49] Tan CS, Hsu TJ, Macromolecules, 30(11), 3147 (1997)

[50] Ree M, Nunes TL, Lin JS, Polymer, 35(6), 1148 (1994)

[51] Scherrer S, Nachr. Gottinger Gesell, 2, 98 (1918)

[52] Rokicki A, Kuran W, J. Macromol. Sci.-Rev. Macromol. Chem. Phys., C21, 135 (1981)

[53] Dreveni I, Berkesi O, Janovics I, Andor JA, Vibrational Spectr., 2, 205 (1991)