Abstract
A silica-supported ionic liquid (Im-IL) was proven to be an effective heterogeneous catalyst for solventless synthesis of cyclic carbonate from allyl glycidyl ether (AGE) and carbon dioxide. Im-IL catalysts were prepared by sol-gel method. The synthesis of cyclic carbonate from AGE and CO2 was carried out in a batch autoclave reactor. Im-IL with shorter alkyl chain length showed the highest conversion of AGE, probably due to the steric hindrance for the formation of intermediate from the catalyst prepared by using longer alkyl chains and AGE. High temperature and high pressure were favorable for the conversion of AGE. Im-IL can be reused for the reaction up to two consecutive runs without any considerable loss of its catalytic activity.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
A.-A. G. Shaikh and S. Sivaram, Chem. Rev., 96, 951 (1996).
R. Sheldon, Chem. Commun., 2399 (2001).
D.-B. Zhao, M. Wu, Y. Kou and E.-Z. Min, Catal. Today, 74, 157 (2002).
P. Wasserscheid and W. Keim, Angew. Chem. Int. Ed., 39, 3772 (2000).
D. Jairton, F. D. S. Roberto and A. Z. S. Paulo, Chem. Rev., 102, 3667 (2002).
K. N. Marsh, A. Deev, A. C. T. Wu, E. Tran and A. Klamt, Korean J. Chem. Eng., 19, 357 (2002).
C. E. Song, W. H. Shim, E. J. Roh and J. H. Choi, Chem. Commun., 1695 (2000).
H. S. Kim, J. J. Kim, H. N. Known, M. J. Chung, B. G. Lee and H. G. Jang, J. Catal., 205, 226 (2002).
H. Yasuda, L. N. Hen and T. Sakakura, J. Catal., 209, 547 (2002).
W. J. Kruper and D. V. Dellar, J. Org. Chem., 60, 725 (1995).
X. Lu, X. Feng and R. He, Appl. Catal. A: Gen., 25, 234 (2002).
M. Yoshida and M. Ihara, Chem. Eur. J., 10, 2886 (2004).
Y. M. Shen, W. L. Duan and M. Shi, Eur. J. Org. Chem., 3080 (2004).
N. Kihara, N. Hara and T. Endo, J. Org. Chem., 58, 6198 (1993).
T. Yano, H. Matsui, T. Koike, H. Ishiguro, H. Rujihara, M. Yoshihara and T. Maeshima, Chem. Commun., 1129 (1997).
K. Yamaguchi, K. Ebitani, T. Yoshida, H. Yoshida and K. Kaneda, J. Am. Chem. Soc., 121, 4526 (1999).
D.-S. Kim and W.-S. Ahn, Korean J. Chem. Eng., 20, 39 (2003).
E. H. Lee, S. W. Cha, M. D. Manju, Y. Choe, J. Y. Ahn and D. W. Park, Korean J. Chem. Eng., 24, 547 (2007).
N. Y. Mun, K. H. Kim, D. W. Park, Y. Choe and I. Kim, Korean J. Chem. Eng., 22, 556 (2005).
H. Z. Yang, Y. Deng and F. Shi, Chem. Commun., 274 (2002).
V. Calo, A. Nacci, A. Monopoli and A. Fanizzi, Org. Lett., 4, 2561 (2002).
F. W. Li, L. F. Xiao, C. G. Xia and B. Hu, Tetrahedron Lett., 45, 8307 (2004).
J. Sun, S. Fujita and M. Arai, J. Organometall. Chem., 690, 3490 (2005).
J. Palgunadi, O. Kwon, H. Lee, J. Y. Bae, B. S. Ahna, N. Y. Min and H. S. Kim, Catal. Today, 98, 511 (2004).
T. Aida and S. Inoue, J. Am. Chem., Soc., 105, 1304 (1983).
R. L. Addock and S. T. Nguyen, J. Am. Chem. Soc., 123, 11498 (2001).
Y. M. Shen, W. L. Duan and M. Shi, J. Org. Chem., 68, 1559 (2003).
H. S. Kim, J. J. Kim, B. G. Lee, O. S. Jung, H. G. Jang and S. O. Kang, Angew. Chem. Int. Ed. Engl., 39, 4096 (2000).
F. W. Li, C. G. Xia, L. W. Xu, W. Sun and G. X. Chen, Chem. Commun., 2042 (2003).
B. S. Yu, E. S. Jeong, K. H. Kim, D. W. Park, S. W. Park and J. W. Lee, React. Kinet. Catal. Lett., 84, 175 (2005).
L. F. Xiao, F. W. Li, J. J. Peng and C. G. Xia, J. Mol. Catal. A. Chem., 253, 265 (2006).
H. Olivier-Bourbigou and L. Magna, J. Mol. Catal. A. Chem., 182, 419 (2002).
D. Zhao, M. Wu, Y. Kou and E. Min, Catal. Today, 74, 157 (2002).
C. L. Liotta, C. M. Starks and M. E. Halpen, Phase Transfer Catalysis, Chapman and Hall, New York (1994).
J. Q. Wang, X. D. Yue, F. Cai and L. N. He, Catal. Commum., 8, 167 (2007).
R. Nomura, M. Kimura, S. Teshima, A. Ninagawa and H. Matsuda, Bull. Chem. Soc. Jpn., 55, 3200 (1982).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Lee, MK., Shim, HL., Dharman, M.M. et al. Synthesis of cyclic carbonate from allyl glycidyl ether and CO2 over silica-supported ionic liquid catalysts prepared by sol-gel method. Korean J. Chem. Eng. 25, 1004–1007 (2008). https://doi.org/10.1007/s11814-008-0162-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11814-008-0162-7