Catalytic performance of quaternary ammonium salts in the reaction of butyl glycidyl ether and carbon dioxide

Hye-Young Ju; Mamparambath-Dharman Manju; Kyung-Hoon Kim; Sang-Wook Park; Dae-Won Park

Journal of Industrial and Engineering Chemistry, Vol.14, No.2, 157-160, March, 2008

DOI10.1016/j.jiec.2007.12.001 Export Citation

Catalytic performance of quaternary ammonium salts in the reaction of butyl glycidyl ether and carbon dioxide

Hye-Young Ju, Mamparambath-Dharman Manju, Kyung-Hoon Kim, Sang-Wook Park , and Dae-Won Park^†

Division of Chemical Engineering, Pusan National University, Busan 609-735, Korea

E-mail:

The synthesis of cyclic carbonate from butyl glycidyl ether (BGE) and carbon dioxide was performed in the presence of quaternary ammonium salt catalysts. Quaternary ammonium salts of different alkyl group (C-3, C-4, C-6 and C-8) and anions (Cl-, Br- and I-) were used for this reaction carried out in a batch autoclave reactor at 60-120 degrees C. The catalytic activity increased with increasing alkyl chain length in the order of C-3 < C-4 < C-6. But, the quaternary ammonium salt with longer alkyl chain length (C-8) decreased the conversion of BGE because it is too bulky to form an intermediate with BGE. For the counter anion of the tetrabutyl ammonium salt catalysts, the BGE conversion decreased in the order Cl- > Br- > I-. The effects of carbon dioxide pressure and reaction temperature on this reaction were also studied to better understand the reaction mechanism. (C) 2007 The Korean Society of Industrial and Engineering Chemistry. Published by Elsevier B.V. All rights reserved.

Keywords:cyclic carbonate;butyl glycidyl ether;carbon dioxide;quaternary ammonium salt

[References]

Peppel WJ, Ind. Eng. Chem., 50, 767 (1958)
Inoue S, Yamazaki N, Organic and Bioorganic Chemistry of Carbon Dioxide, Kodansha Ltd., Tokyo (1981)
Inoue S, Tsuruta T, Koinuma H, J. Polym. Sci. Polym. Lett., 7, 287 (1969)
Rokicki A, Kuran WJ, Macromol. Sci. Rev. Macromol. Chem., C21, 135 (1981)
Super MS, Beckman EJ, Trends Polym. Sci., 5(7), 236 (1997)
Darensbourg DJ, Mackiewiicz RM, Phelps AL, Billodeaux DR, Accounts Chem. Res., 37, 836 (2004)
Coates GW, Moore DR, Angew. Chem.-Int. Edit., 43, 6618 (2004)
Sugimoto H, Inoue S, J. Polym. Sci. A: Polym. Chem., 42(22), 5561 (2004)
Park SW, Choi BS, Park DW, Kim SS, J. Ind. Eng. Chem., 11(4), 527 (2005)
Kim MR, Jeon SR, Park DW, Lee JK, J. Ind. Eng. Chem., 4(2), 122 (1998)
Park DW, Yu BS, Jeong ES, Kim I, Kim MI, Oh KJ, Park SW, Catal. Today, 98(4), 499 (2004)
Yu BS, Jeong ES, Kim KH, Park DW, Park SW, Lee JW, React. Kinet. Catal. Lett., 84(1), 175 (2005)
Calo V, Nacci A, Monopoli A, Fanizzi A, Org. Lett., 4, 2561 (2002)
Sun JM, Fujita SI, Zhao FY, Arai M, Appl. Catal. A: Gen., 287(2), 221 (2005)
Lee DW, Hur JH, Kim BK, Park SW, Park DW, J. Ind. Eng. Chem., 9(5), 513 (2003)
Starks CM, Littoa CL, Halpern M, Phase Transfer Catalysis, Chapman and Hall, New York, 1994, p. 11
Park SY, Park HY, Park DW, Ha CS, J. Macromol. Sci.-Pure Appl. Chem., A39, 573 (2002)
Peng J, Deng Y, New J. Chem., 25, 639 (2001)

[Referenced By]

[Related Articles]

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

[2] Inoue S, Yamazaki N, Organic and Bioorganic Chemistry of Carbon Dioxide, Kodansha Ltd., Tokyo (1981)

[3] Inoue S, Tsuruta T, Koinuma H, J. Polym. Sci. Polym. Lett., 7, 287 (1969)

[4] Rokicki A, Kuran WJ, Macromol. Sci. Rev. Macromol. Chem., C21, 135 (1981)

[5] Super MS, Beckman EJ, Trends Polym. Sci., 5(7), 236 (1997)

[6] Darensbourg DJ, Mackiewiicz RM, Phelps AL, Billodeaux DR, Accounts Chem. Res., 37, 836 (2004)

[7] Coates GW, Moore DR, Angew. Chem.-Int. Edit., 43, 6618 (2004)

[8] Sugimoto H, Inoue S, J. Polym. Sci. A: Polym. Chem., 42(22), 5561 (2004)

[9] Park SW, Choi BS, Park DW, Kim SS, J. Ind. Eng. Chem., 11(4), 527 (2005)

[10] Kim MR, Jeon SR, Park DW, Lee JK, J. Ind. Eng. Chem., 4(2), 122 (1998)

[11] Park DW, Yu BS, Jeong ES, Kim I, Kim MI, Oh KJ, Park SW, Catal. Today, 98(4), 499 (2004)

[12] Yu BS, Jeong ES, Kim KH, Park DW, Park SW, Lee JW, React. Kinet. Catal. Lett., 84(1), 175 (2005)

[13] Calo V, Nacci A, Monopoli A, Fanizzi A, Org. Lett., 4, 2561 (2002)

[14] Sun JM, Fujita SI, Zhao FY, Arai M, Appl. Catal. A: Gen., 287(2), 221 (2005)

[15] Lee DW, Hur JH, Kim BK, Park SW, Park DW, J. Ind. Eng. Chem., 9(5), 513 (2003)

[16] Starks CM, Littoa CL, Halpern M, Phase Transfer Catalysis, Chapman and Hall, New York, 1994, p. 11

[17] Park SY, Park HY, Park DW, Ha CS, J. Macromol. Sci.-Pure Appl. Chem., A39, 573 (2002)

[18] Peng J, Deng Y, New J. Chem., 25, 639 (2001)