Activity Investigation of Imidazolium-Based Ionic Liquid as Catalyst for Friedel-Crafts Alkylation of Aromatic Compounds

Mingjian Cai; Xiuge Wang

doi:10.14233/ajchem.2015.17407

Issue

Vol. 27 No. 2 (2015): Vol 27 Issue 2

Issue Published : January 10, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Activity Investigation of Imidazolium-Based Ionic Liquid as Catalyst for Friedel-Crafts Alkylation of Aromatic Compounds

https://doi.org/10.14233/ajchem.2015.17407

Mingjian Cai

Department of Chemistry, Tangshan Normal University, Tangshan 063000, Hebei Province, P.R. China

Xiuge Wang

Department of Chemistry, Tangshan Normal University, Tangshan 063000, Hebei Province, P.R. China

Corresponding Author(s) : Mingjian Cai

cmj_1237@aliyun.com

Asian Journal of Chemistry, Vol. 27 No. 2 (2015): Vol 27 Issue 2
Article Published : January 10, 2015

Abstract

N-Methylimidazolium ionic liquids were synthesised from N-methylimidazole and 1-bromobutane by two-step method. The alkylation of benzene and other aromatic compounds through improved Friedel-Crafts reaction was investigated in these ionic liquids. The imidazolium-based ionic liquids showed both high activity and high selectivity for this reaction. In particular, remarkable enhancement of the catalytic effect of the imidazolium-based ionic liquids was observed for the ionic liquids containing the PF₆^- anion. The effects of various types of anions, ionic liquid dosage, reaction temperature and molar ratio of aromatic compound to 1-bromobutane/tertbutyl alcohol were explored using [Bmim]PF₆ or its mixture with AlCl₃ as catalyst. The synthesis yielded improved results over those obtained using either neat AlCl₃ or other imidazolium-based ionic liquids as catalyst. The ionic liquids can also be recycled and reused in contrast to traditional solvent-catalyst systems.

Keywords

Imidazolium-based ionic liquids Alkylation Friedel-Crafts Aluminium chloride

Cai, M., & Wang, X. (2015). Activity Investigation of Imidazolium-Based Ionic Liquid as Catalyst for Friedel-Crafts Alkylation of Aromatic Compounds. Asian Journal of Chemistry, 27(2), 649–653. https://doi.org/10.14233/ajchem.2015.17407

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References

(a) R.M. Roberts and A.A. Khalaf, Friedel-Crafts Alkylation Chemistry, Marcel Dekker, New York (1984); (b) G.A. Olah, Friedel-Crafts and Related Reactions, vol. I-IV, Wiley-Interscience, New York (1963).

M. Huellmann, H. Mayr and R. Becker Ger. Offen. DE 4 008 694, (1991); Chem. Abstr., 116, 6262x (1991).

S.W. Tang, A.M. Scurto and B. Subramaniam, J. Catal., 268, 243 (2009); doi:10.1016/j.jcat.2009.09.022.

J.L.G. Almeida, M. Dufaux, Y.B. Taarit and C. Naccache, J. Am. Oil Chem. Soc., 71, 675 (1994); doi:10.1007/BF02541423.

B. Vora, P. Pujado, I. Imai and T. Fritsch, Chem. Ind., 19, 187 (1990).

K.G. Chandra and M.M. Sharma, Catal. Lett., 19, 309 (1993); doi:10.1007/BF00767072.

A. Sakthivel, S.K. Badamali and P. Selvam, Micropor. Mesopor. Mater., 39, 457 (2000); doi:10.1016/S1387-1811(00)00222-5.

A.V. Krishnan, K. Ojha and N.C. Pradhan, Org. Process Res. Dev., 6, 132 (2002); doi:10.1021/op010077n.

K. Zhang, H. Zhang, G. Xu, S. Xiang, D. Xu, S. Liu and H. Li, Appl. Catal. A, 207, 183 (2001); doi:10.1016/S0926-860X(00)00663-3.

S. Subramanian, A. Mitra, C.V.V. Satyanarayana and D.K. Chakrabarty, Appl. Catal. A, 159, 229 (1997); doi:10.1016/S0926-860X(97)00030-6.

J. Weitkamp and Y. Traa, Catal. Today, 49, 193 (1999); doi:10.1016/S0920-5861(98)00424-6.

J.P. Hallett and T. Welton, Chem. Rev., 111, 3508 (2011); doi:10.1021/cr1003248.

Y. Liu, R. Hu, C. Xu and H. Su, Appl. Catal. A, 346, 189 (2008); doi:10.1016/j.apcata.2008.05.024.

T.L.T. Bui, W. Korth, S. Aschauer and A. Jess, Green Chem., 11, 1961 (2009); doi:10.1039/b913872b.

Y. Yu, L. Hua, W. Zhu, Y. Shi, T. Cao, Y. Qiao and Z. Hou, Synth. Commun., 43, 1287 (2013); doi:10.1080/00397911.2011.632702.

A. Parmar, V.K. Aswal and P. Bahadur, Spectrochim. Acta A, 97, 137 (2012); doi:10.1016/j.saa.2012.05.075.

P. Wasserscheid, M. Sesing and W. Korth, Green Chem., 4, 134 (2002); doi:10.1039/b109845b.

O. Holloczki, D. Gerhard, K. Massone, L. Szarvas, B. Nemeth, T. Veszpremi and L. Nyulaszi, New J. Chem., 34, 3004 (2010); doi:10.1039/c0nj00380h.

C.Z. Qiao, Y.F. Zhang, J.C. Zhang and C.Y. Li, Appl. Catal. A, 276, 61 (2004); doi:10.1016/j.apcata.2004.07.021.

H.L. Xin, Q. Wu, M.H. Han, D.Z. Wang and Y. Jin, Appl. Catal. A, 292, 354 (2005); doi:10.1016/j.apcata.2005.06.012.

Z.K. Zhao, Z.S. Li, G.R. Wang, W.H. Qiao and L.B. Cheng, Appl. Catal. A, 262, 69 (2004); doi:10.1016/j.apcata.2003.11.008.

Issue

Vol. 27 No. 2 (2015): Vol 27 Issue 2

Activity Investigation of Imidazolium-Based Ionic Liquid as Catalyst for Friedel-Crafts Alkylation of Aromatic Compounds

Corresponding Author(s) : Mingjian Cai

Abstract

Keywords

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