Issue
Korean Journal of Chemical Engineering,
Vol.24, No.3, 547-550, 2007
Cycloaddition of carbon dioxide to epichlorohydrin using ionic liquid as a catalyst
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.
[References]
  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