Abstract
Alkylation of anthracene with 2-chloropropane to 2-isopropylanthracene catalyzed by various Lewis acidic ionic liquids (ILs), such as [Emim]Cl-AlCl3, [Emim]Cl-FeCl3, [Emim]Cl-ZnCl2, [Bmim]Cl-AlCl3, and [Omim]Cl-AlCl3 ([Emim]+=1-ethyl-3-methylimidazolium cation, [Bmim]+=1-butyl-3-methylimidazolium cation, [Omim]+=1-octyl-3-methylimidazolium cation,), was investigated. [Emim]C1-A1C13 ionic liquid was found to be the most active catalyst in the alkylation. The yield of 2-isopropylanthracene was up to 74.5% and the selectivity of 2-isopropylanthracene was up to 82.9%. The [Emim]C1-A1C13 ionic liquid catalyst showed good catalytic activity after running for 6 times. Ease of product separation and the recycling performance of the ionic liquid catalyst is expected to contribute to the development of clean and environmentally friendly strategy for the synthesis of 2-isopropylanthracene.
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References
M. Bandini, A. Melloni and A. Umani-Rouchi, Angew. Chem. Int. Ed., 43, 550 (2004).
C. Z. Qiao, Y. F. Zhang and J. C. Zhang, Appl. Catal. A, 276, 61 (2004).
M. Ghiaci, A. Abbaspur and M. Arshadi, Appl. Catal. A, 316, 32 (2007).
S. Sivasnaker and A. Thangaraj, J. Catal., 138, 386 (1992).
J. L.G. Almeida, M. Dufanux and Y.B. Taarit, Appl. Catal. A, 114, 141 (1994).
M. Han, Z. Cui, C. Xu, W. Chen and Y. Jin, Appl. Catal. A, 238, 99 (2003).
S. Namuangruk, P. Pantu and J. Limtrakul, J. Catal., 225, 523 (2004).
M. Lenarda, L. Storaro, G. Pellegrini, L. Piovesan and R. Ganzerla, J. Mol. Catal. A, 145, 237 (1999).
A. Angelis, S. Amarilli, D. Berti, L. Montanari and C. Perego, J. Mol. Catal. A, 146, 37 (1999).
R. T. Sebusky and A. M. Henke, Ind. Eng. Chem. Process Res., Dev., 2, 272 (1971).
W. Xu, H. L. Tong, C.H. Chen and X.H. Xu, Korean J. Chem. Eng., 25, 53 (2008).
J. Howarth, P. James and J. F. Dai, Tetrahedron Lett., 41, 10319 (2000).
X.G. Xie, J. P. Lu and B. Chen, Tetrahedron Lett., 45, 809 (2004).
J. S. Yadav, B.V. S. Reddy and A.K. Basak, Tetrahedron Lett., 44, 2217 (2003).
C. Baleizao, N. Pires and B. Gigante, Tetrahedron Lett., 45, 4375 (2004).
Y. Xiao and S. V. Malhotra, Tetrahedron Lett., 45, 8339 (2004).
J. A. Boon, J. A. Levisky and J. L. Pflug, J. Org. Chem., 51, 480 (1986).
C. Z. Qiao, Y. F. Zhang and J. C. Zhang, Appl. Catal. A, 276, 61 (2004).
C.G. Blanco, D. C. Banciella and D.G. Azpiroz, J. Mol. Catal. A, 253, 203 (2006).
Z.K. Zhao, W. H. Qiao and X. N. Wang, Appl. Catal. A, 290, 133 (2005).
P. Wasserscheid and W. Keim, Angew. Chem. Int. Ed., 39, 3772 (2000).
G.H. Jonathan, E.V. Ann and W. M. Reichert, Green Chem., 31, 56 (2001).
C. J. Adams, M. J. Earle and K. R. Seddon, Chem. Commum., 19, 2097 (1998).
J.G. Huddleston, A. E. Visser, W. M. Reichert, H. D. Willauer, G. A. Broker and R. D. Rogers, Green Chem., 3, 156 (2001).
T. Welton, Chem. Rev., 99, 2071 (1999).
S. J. Nara, J. R. Harjani and M. M. Salunkhe, J. Org. Chem., 66, 8616 (2001).
P. Vogel, Carbocation chemistry, elsevier amsterdam, 444 (1985).
C. Reichardt, Federal republic of germany VCH weinheim, 248 (1988).
H. L. Xin, Q. Wu, M.H. Han, D. Z. Wang and Y. Jin, Appl. Catal. A, 292, 354 (2005).
J. Howarth, K. Hanlon, D. Fayne and P. McCormac, Tetrahedron Lett., 38, 3097 (1997).
K. Yoo, V.V. Namboodiri, R. S. Varma and P.G. Smirniotis, J. Catal., 222, 511 (2004).
C. L. Hussey and G. Mamantov, Ed. Elsevier: Amsterdam, 5, 185 (1983).
T. Matsumoto and K. Ichikawa, J. Am. Chem. Soc., 106, 4316 (1984).
R. J. Gale, B. Gilbert and R. A. Osteryoung, Inorg. Chem., 17, 2728 (1978).
E. Rytter, H.A. Øye, S. J. Cyvin, B.N. Cyvin and P. J. Klaelboe, Inorg. Nucl. Chem., 35, 1185 (1973).
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Chen, M., Luo, Y., Li, G. et al. Alkylation of anthracene to 2-isopropylanthracene catalyzed by Lewis acid ionic liquids. Korean J. Chem. Eng. 26, 1563–1567 (2009). https://doi.org/10.1007/s11814-009-0257-9
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DOI: https://doi.org/10.1007/s11814-009-0257-9