Synthesis of Bis(Cyclic Carbonate)s from Carbon Dioxide and Diglycidyl Ethers

Mi-Ra Kim; Sa-Ra Jeong; Dae-Won Park; Jin-Kook Lee

Journal of Industrial and Engineering Chemistry, Vol.4, No.2, 122-126, June, 1998

Mi-Ra Kim, Sa-Ra Jeong, Dae-Won Park¹, and Jin-Kook Lee

Department of Polymer Science and Engineering, Pusan National University, Pusan 609-735, Korea
¹Department of Chemical Engineering, Pusan National University, Pusan 609-735, Korea

Diglycidyl ether derivatives were synthesized from diols and epichlorohydrin using basic catalysts. Synthesis of bits(cyclic carbonate)s from the addition reaction of carbon dioxide with diglycidyl ether derivatives were performed in the presence of phase transfer catalyst (PTC). PTCs are more effective catalysts than alkali metal catalysts. The intrinsic activity of PTC in the reaction of carbon dioxide and diglycidyl ethers was found to follow the order of nucleophilicity of the anion (Cl^-Br^-I^-) in aprotic solvent such as N-methyl-2-pyrrolidone (NMP) in accord with the higher alkyl chain length (Oct₄⁺ Hex₄⁺ Bu₄⁺ Pr₄⁺). It was also found that the reactivity of carbon dioxide decreases as the aliphatic chain length of diglycidyl ether increases because of chain folding and the steric hinderance of methyl groups.

[References]

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[Referenced By]

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

[2] Peppel WJ, Ind. Eng. Chem., 50, 767 (1958)

[3] Rokicki G, Kuran W, Kielkiewicz J, J. Polym. Sci. A: Polym. Chem., 20, 967 (1982)

[4] Rokicki G, Pawlicki J, Kuran W, Polym. J., 17, 509 (1985)

[5] Brindopke G, German Patent, DE3529263 (1987)

[6] Dense B, Sneeden RPA, Chem. Tech., 108 (1984)

[7] Baba A, Nozaki T, Matsuda H, Bull. Chem. Soc. Jpn., 60, 1552 (1987)

[8] Johnson PH, Report 1985, LBL-19886, Order No. DE85016526; Chem. Abstr., 105, 87285e (1986)

[9] Tsuda T, Chujo Y, Saejusa T, J. Am. Chem. Soc., 100, 630 (1978)

[10] Rasquale RJ, J. Chem. Soc.-Chem. Commun., 157 (1973)

[11] Kihara N, Hara N, Endo T, J. Org. Chem., 58, 6198 (1993)

[12] Freedman HH, Pure Appl. Chem., 58, 857 (1986)

[13] Nishikubo T, Kameyama A, Yamashita J, Tmoi M, Fukuda W, J. Polym. Sci. A: Polym. Chem., 31, 939 (1993)

[14] Starks CM, Liotta CL, Halpern M, Phase Transfer Catalysis, Chapman & Hall, N.Y. (1994)

[15] Liaw DJ, Shen WC, Die. Ang. Makro. Chem., 200, 137 (1992)

[16] Acitelli MA, Prime RB, Sacher E, Polymer, 12, 335 (1971)

[17] Nishikubo T, Kameyama A, Sasano M, J. Polym. Sci. A: Polym. Chem., 32(2), 301 (1994)

[18] Kihara N, Endo T, Makromol. Chem., 193, 1481 (1992)

[19] Kihara N, Endo T, Macromolecules, 25, 4824 (1992)

[20] Kihara N, Hara N, Endo T, J. Org. Chem., 58, 6198 (1993)

[21] Podzimek S, Sykora V, Horalek J, Svestka S, J. Appl. Polym. Sci., 58(9), 1491 (1995)

[22] Streitwieser A, Solvolytic Displacement Reactions, McGraw Hill, New York (1962)

[23] Streitwieser A, Chem. Rev., 56, 571 (1956)