Cycloaddition of carbon dioxide to epichlorohydrin using ionic liquid as a catalyst

Eun-Ha Lee; So-Wan Cha; Manju Mamparambath Dharma; Youngson Choe; Ji-Yun Ahn; Dae-Won Park

Korean Journal of Chemical Engineering, Vol.24, No.3, 547-550, May, 2007

DOI10.1007/s11814-007-0097-4 Export Citation

Cycloaddition of carbon dioxide to epichlorohydrin using ionic liquid as a catalyst

Eun-Ha Lee, So-Wan Cha¹, Manju Mamparambath Dharma, Youngson Choe , Ji-Yun Ahn, and Dae-Won Park^†

Division of Chemical Engineering, Pusan National University, Busan 609-735, Korea
¹Korea Minjok Leadership Academy, Heyongseong-gun, Kangwon-do 225-823, Korea

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The cycloaddition of carbon dioxide to epichlorohydrin was performed without any solvent in the presence of ionic liquid as catalyst. 1-Alkyl-3-methyl imidazolium salts of different alkyl group (C2, C4, C6, C8) and anions (Cl-,BF4-, Br-, PF6-) were used for this reaction carried out in a batch autoclave reactor. The conversion of epichlorohydrin was affected by the structure of the imidazolium salt ionic liquid; the one with the cation of longer alkyl chain length and with more nucleophilic anion showed better reactivity. The conversion of epichlorohydrin increased as the temperature increased from 60 ℃ to 140 ℃. It also increased with increasing carbon dioxide pressure probably due to the increase of the absorption of carbon dioxide into the mixture of epichlorohydrin and the ionic liquid. Zinc bromide was also tested for its use as a cocatalyst in this reaction.

Keywords:Cycloaddition;Epichlorohydrin;Ionic Liquid;Carbon Dioxide

[References]

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Xu XD, Moulijin JA, Energy Fuels, and references therein, 10, 305 (1996)
Gibson DH, Coord. Chem. Rev., 185-186, 335 (1999)
Shi M, Shen YM, Curr. Org. Chem., 7, 737 (2003)
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Weissermel K, Arpe H, (Eds.), Industrial organic chemistry, third ed., Wiley-VCH, Weinheim, New York, 162 (1997)
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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)
Shin DH, Kim JJ, Yu BS, Lee MH, Park DW, Korean J. Chem. Eng., 20(1), 71 (2003)
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Kawanami H, Sasaki A, Matsui K, Ikushima Y, Chem. Commun., 896 (2003)
Zhang S, Yuan X, Chen Y, Zhang X, J. Chem. Eng. Data, 50, 1582 (2005)
Yamaguchi K, Ebitani K, Yoshida T, Yoshida H, Kaneda K, J. Am. Chem. Soc., 121(18), 4526 (1999)
Paddock RL, Hiyama Y, McKay JM, Nguyen ST, Tetrahedron Lett., 45, 2023 (2004)
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[Referenced By]

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[1] Darensbourg DJ, Holtcamp MW, Coord. Chem. Rev., 155, 153 (1996)

[2] Xu XD, Moulijin JA, Energy Fuels, and references therein, 10, 305 (1996)

[3] Gibson DH, Coord. Chem. Rev., 185-186, 335 (1999)

[4] Shi M, Shen YM, Curr. Org. Chem., 7, 737 (2003)

[5] Shaikh AAG, Sivaram S, Chem. Rev., 96, 951 (1996)

[6] Weissermel K, Arpe H, (Eds.), Industrial organic chemistry, third ed., Wiley-VCH, Weinheim, New York, 162 (1997)

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

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

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

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

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

[12] Shin DH, Kim JJ, Yu BS, Lee MH, Park DW, Korean J. Chem. Eng., 20(1), 71 (2003)

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

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

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

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

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

[18] Seddon KR, Kinet. Catal., 37, 693 (1996)

[19] Larsen AS, Holbrey JD, Tham FS, Reed CA, J. Am. Chem. Soc., 122(30), 7264 (2000)

[20] Zhao DB, Wu M, Kou Y, Min E, Catal. Today, 74(1-2), 157 (2002)

[21] Sheldon R, Chem. Commun., 2399 (2001)

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

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

[24] Kawanami H, Sasaki A, Matsui K, Ikushima Y, Chem. Commun., 896 (2003)

[25] Zhang S, Yuan X, Chen Y, Zhang X, J. Chem. Eng. Data, 50, 1582 (2005)

[26] Yamaguchi K, Ebitani K, Yoshida T, Yoshida H, Kaneda K, J. Am. Chem. Soc., 121(18), 4526 (1999)

[27] Paddock RL, Hiyama Y, McKay JM, Nguyen ST, Tetrahedron Lett., 45, 2023 (2004)

[28] Sun J, Fujita S, Zhao F, Arai M, Green Chem., 6, 613 (2004)

[29] Fuwei L, Linfei X, Chungu X, Bin H, Tetrahedron Lett., 45, 8307 (2004)