Chemical fixation of carbon dioxide to dimethyl carbonate from propylene carbonate and methanol using ionic liquid catalysts

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

Korean Journal of Chemical Engineering, Vol.24, No.5, 917-919, September, 2007

DOI10.1007/s11814-007-0065-z Export Citation

Chemical fixation of carbon dioxide to dimethyl carbonate from propylene carbonate and methanol using ionic liquid catalysts

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

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The synthesis of dimethyl carbonate (DMC) through the transesterification of propylene carbonate (PC) with methanol was investigated by using imidazolium salt ionic liquid catalysts. 1-alkyl-3-methyl imidazolium salts of different alkyl group (C2, C4, C6, C8) and anions (Cl., Br., BF4.,PF6.) were used for catalysts. The reaction was carried out in an autoclave at 140-180 ℃ under carbon dioxide pressure of 1.48-5.61MPa. The imidazolium salts of shorter alkyl group, and more nucleophilic counter anion exhibited higher catalytic activity. The conversion of PC increased as CO2 pressure and reaction temperature increased. Kinetic studies were also performed to better understand the reaction mechanism.

Keywords:Dimethyl Carbonate;Transesterification;Propylene Carbonate;Methanol;Ionic Liquid

[References]

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Trost BM, Science, 254, 1471 (1991)
Fujita S, Bhanage BM, Ikushima Y, Shirai M, Torii K, Arai M, Catal. Lett., 79, 95 (2002)
Aresta M, Dibenedetto A, J. Mol. Catal. A-Chem., 182, 399 (2002)
Aresta M, Dibenedetto A, Tommasi I, Appl. Organomet. Chem., 14, 799 (2000)
Billard I, Moutiers G, Labet A, El Azzi A, Gaillard C, Mariet C, Lutzenkirchen K, Inorg. Chem., 42(5), 1726 (2003)
Olivier-Bourbigou H, Magna L, J. Mol. Catal. A-Chem., 182, 419 (2002)
Kim DS, Ahn WS, Korean J. Chem. Eng., 20(1), 39 (2003)
Song CE, Shim WH, Roh EJ, Choi JH, Chem. Commun., 1695 (2000)
Mun NY, Kim KH, Park DW, Choe Y, Kim I, Korean J. Chem. Eng., 22(4), 556 (2005)
Welton T, Chem. Rev., 99(8), 2071 (1999)
Bhanage BM, Fujita S, Ikushima Y, Arai M, Appl. Catal. A: Gen., 219(1-2), 259 (2001)
Buysch HJ, Krimm H, Rudolph H, US Patent 4, 181, 676 (1980)
Kondoh T, Okada Y, Tanaka F, Asaoka S, Yamamoto S, US Patent 5, 436, 362 (1995)
Tatsumi T, Watanake Y, Koyano KA, Chem. Commun., 2281 (1996)
Abimanyu H, Yoo KS, Moon DJ, Ahn BS, Song J, J. Ind. Eng. Chem., 11(4), 502 (2005)
Watanabe Y, Tatsumi T, Microporous Mesoporous Mater., 22, 399 (1998)
Jeong ES, Kim KH, Park DW, Park SW, Lee JW, React. Kinet. Catal. Lett., 86(2), 241 (2005)
Bonhote P, Dias AP, Papageorgiou N, Kalyanasundaram K, Gratzel M, Inorg. Chem., 35(5), 1168 (1996)
Huddleston JG, Visser AE, Reichert WM, Willauer HD, Broker GA, Rogers RD, Green Chem., 3, 156 (2001)
Tian JS, Wang JQ, Chen JY, Fan JG, Cai F, He LN, Appl. Catal. A: Gen., 301(2), 215 (2006)
Starks CM, Littoa CL, Halpern M, Phase transfer catalysis, Chapman and Hall, New York (1994)

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[3] Trost BM, Science, 254, 1471 (1991)

[4] Fujita S, Bhanage BM, Ikushima Y, Shirai M, Torii K, Arai M, Catal. Lett., 79, 95 (2002)

[5] Aresta M, Dibenedetto A, J. Mol. Catal. A-Chem., 182, 399 (2002)

[6] Aresta M, Dibenedetto A, Tommasi I, Appl. Organomet. Chem., 14, 799 (2000)

[7] Billard I, Moutiers G, Labet A, El Azzi A, Gaillard C, Mariet C, Lutzenkirchen K, Inorg. Chem., 42(5), 1726 (2003)

[8] Olivier-Bourbigou H, Magna L, J. Mol. Catal. A-Chem., 182, 419 (2002)

[9] Kim DS, Ahn WS, Korean J. Chem. Eng., 20(1), 39 (2003)

[10] Song CE, Shim WH, Roh EJ, Choi JH, Chem. Commun., 1695 (2000)

[11] Mun NY, Kim KH, Park DW, Choe Y, Kim I, Korean J. Chem. Eng., 22(4), 556 (2005)

[12] Welton T, Chem. Rev., 99(8), 2071 (1999)

[13] Bhanage BM, Fujita S, Ikushima Y, Arai M, Appl. Catal. A: Gen., 219(1-2), 259 (2001)

[14] Buysch HJ, Krimm H, Rudolph H, US Patent 4, 181, 676 (1980)

[15] Kondoh T, Okada Y, Tanaka F, Asaoka S, Yamamoto S, US Patent 5, 436, 362 (1995)

[16] Tatsumi T, Watanake Y, Koyano KA, Chem. Commun., 2281 (1996)

[17] Abimanyu H, Yoo KS, Moon DJ, Ahn BS, Song J, J. Ind. Eng. Chem., 11(4), 502 (2005)

[18] Watanabe Y, Tatsumi T, Microporous Mesoporous Mater., 22, 399 (1998)

[19] Jeong ES, Kim KH, Park DW, Park SW, Lee JW, React. Kinet. Catal. Lett., 86(2), 241 (2005)

[20] Bonhote P, Dias AP, Papageorgiou N, Kalyanasundaram K, Gratzel M, Inorg. Chem., 35(5), 1168 (1996)

[21] Huddleston JG, Visser AE, Reichert WM, Willauer HD, Broker GA, Rogers RD, Green Chem., 3, 156 (2001)

[22] Tian JS, Wang JQ, Chen JY, Fan JG, Cai F, He LN, Appl. Catal. A: Gen., 301(2), 215 (2006)

[23] Starks CM, Littoa CL, Halpern M, Phase transfer catalysis, Chapman and Hall, New York (1994)