Issue
Korean Journal of Chemical Engineering,
Vol.27, No.2, 446-451, 2010
Cycloaddition of carbon dioxide to butyl glycidyl ether using imidazolium salt ionic liquid as a catalyst
The catalytic performance of imidazolium salt ionic liquids in the cycloaddition of carbon dioxide to butyl glycidyl ether (BGE) was investigated. The catalytic activity was tested with different imidazolium salt ionic liquids at 60-140 ℃ under 0.62-2.17MPa of CO2 pressure. The imidazolium salt ionic liquid with the cation of bulkier alkyl chain length and with more nucleophilic anion showed higher conversion of BGE. High carbon dioxide pressure and high reaction temperature up to 140 ℃ was favorable for the high reactivity of the catalyst. The presence of zinc bromide co-catalyst enhanced the reactivity of the imidazolium salt ionic liquid. Kinetic studies with a semi-batch reactor revealed that the reaction could be considered as first order with respect to the concentration of BGE, and the activation energy was estimated as 22.6 and 22.8 kJ/mol for 1-ethyl-3-methylimidazolium chloride (EMImCl) and 1-butyl-3-methylimidazolium chloride (BMImCl), respectively.
[References]
  1. Song CS, Catal. Today, 115(1-4), 2, 2006
  2. Aresta M, Dibenedetto A, Dalton Trans., 2975, 2007
  3. Omae I, Catal. Today, 115(1-4), 33, 2006
  4. Darensbourg DJ, Holtcamp MW, Coord. Chem. Rev., 155, 153, 1996
  5. Shaikh AA, Sivaram S, Chem. Rev., 96(3), 951, 1996
  6. Kihara N, Hara N, Endo T, J. Org. Chem., 58, 6198, 1993
  7. Aresta M, Carbon dioxide recovery and utilization, Springer, New York, 2003
  8. Kruper W, Deller D, J. Org. Chem., 60, 725, 1995
  9. Kim HS, Kim JJ, Lee BG, Jung OS, Jang HG, Kang SO, Angew. Chem. Int. Ed., 39, 4096, 2000
  10. Sujith S, Min JK, Seong JE, Na SJ, Lee BY, Angew. Chem. Int. Ed., 47, 7306, 2008
  11. Welton T, Chem. Rev., 99(8), 2071, 1999
  12. Song CE, Shim WH, Roh EJ, Choi JH, Chem. Commun., 1695, 2000
  13. Holbrey JD, Seddon KR, Clean Prod. Precess., 1, 223, 1999
  14. Wasserscheid P, Keim W, Angew. Chem. Int. Ed., 39, 3772, 2000
  15. Hagiwara R, Ito Y, J. Fluorine Chem., 105, 221, 2000
  16. Freemantle M, Chem. Eng. News, 78, 120, 2000
  17. Mun NY, Kim KH, Park DW, Choe Y, Kim I, Korean J. Chem. Eng., 22(4), 556, 2005
  18. Lee EH, Cha SW, Dharma MM, Choe Y, Ahn JY, Park DW, Korean J. Chem. Eng., 24(3), 547, 2007
  19. Kim DS, Ahn WS, Korean J. Chem. Eng., 20(1), 39, 2003
  20. Seddon KR, Kinet. Catal., 37, 693, 1996
  21. Larsen AS, Holbrey JD, Tham FS, Reed CA, J. Am. Chem. Soc., 122(30), 7264, 2000
  22. Palgunadi J, Kwon OS, Lee H, Bae JY, Ahn BS, Min NY, Kim HS, Catal. Today, 98(4), 511, 2004
  23. Srivastava R, Srinivas D, Ratnasamy P, Appl. Catal. A: Gen., 289(2), 128, 2005
  24. Xie Y, Zhang Z, Jiang T, He J, Han B, Wu T, Ding K, Angew. Chem. Int. Ed., 46, 1, 2007
  25. Zhou YX, Hu SQ, Ma XM, Liang SG, Jiang T, Han BX, J. Mol. Catal. A-Chem., 284(1-2), 52, 2008
  26. Lee EH, Ahn JY, Dharman MM, Park DW, Park SW, Kim I, Catal. Today, 131(1-4), 130, 2008
  27. Park DW, Mun NY, Kim KH, Kim I, Park SW, Catal. Today, 115(1-4), 130, 2006
  28. Ju HY, Manju MD, Kim KH, Park SW, Park DW, J. Ind. Eng. Chem., 14(2), 157, 2008
  29. Ahn JY, Shim HL, Kim KH, Kim I, Park SW, Park DW, Korean J. Chem. Eng., 25(4), 693, 2008
  30. Sun JM, Fujita SI, Arai M, J. Organomet. Chem., 690, 3490, 2005
  31. Mao LF, Li FW, Peng HH, Xia CG, J. Mol. Catal. A-Chem., 253(1-2), 265, 2006
  32. Udayakumar S, Park SW, Park DW, Choi BS, Catal. Commun., 9, 1563, 2008
  33. Lee MK, Shim HL, Dharman MM, Kim KH, Park SW, Park DW, Korean J. Chem. Eng., 25(5), 1004, 2008
  34. Park DW, Yu BS, Jeong ES, Kim I, Kim MI, Oh KJ, Park SW, Catal. Today, 98(4), 499, 2004
  35. Shin DH, Kim JJ, Yu BS, Lee MH, Park DW, Korean J. Chem. Eng., 20(1), 71, 2003
  36. Seddon KR, Kinet. Catal., 37, 693, 1996
  37. Calo V, Nacci A, Monopoli A, Fanizzi A, Org. Lett., 4, 2561, 2002
  38. Starks CM, Littoa CL, Halpern M, Phase transfer catalysis, Chapman and Hall, New York, 1994
  39. Kawanami H, Sasaki A, Matsui K, Ikushima Y, Chem. Commun., 896, 2003
  40. Zhang S, Yuan X, Chen Y, Zhang X, J. Chem. Eng. Data, 50, 1582, 2005
  41. Darensbourg DJ, Mackiewicz RM, Billodeux DR, Organometallics, 24, 144, 2005
  42. Sun J, Fujita SI, Zhao F, Arai M, Green Chem., 6, 613, 2004
  43. Fuwei L, Linfei X, Chungu X, Bin H, Tetrahedron Lett., 45, 8307, 2004