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Activity of Imidazolium-Based Ionic Liquids as Catalysts for Friedel-Crafts Acylation of Aromatic Compounds
Corresponding Author(s) : Mingjian Cai
Asian Journal of Chemistry,
Vol. 26 No. 18 (2014): Vol 26 Issue 18
Abstract
Friedel-Crafts acylation of three aromatic compounds with acetyl chloride catalyzed by two kinds of ionic liquids was investigated. The imidazolium-based ionic liquids showed both high activity and high selectivity for this reaction. In particular, the catalytic effect of imidazolium-based ionic liquids was dramatically enhanced for ionic liquids containing the BF4- and Br- anions. The effects of various types of anion, ionic liquid dosage, reaction temperature and time were explored using [Bmim]BF4 or [Bmim]Br as catalyst. Results show that ionic liquids can be used as both catalyst and solvent.
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- G. Olah, in Friedel-Crafts and Related Reactions, Wiley Interscience: New York and London, Vols. I-IV (1963-1964).
- H. Szmant, Organic Building Blocks of the Chemical Industry, Wiley, New York (1989).
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- C. Paun, C. Stere, S.M. Coman, V.I. Parvulescu, P. Goodrich and C. Hardacre, Catal. Today, 131, 98 (2008); doi:10.1016/j.cattod.2007.10.028.
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- G. Wine, C. Pham-Huu and M. Ledoux, Catal. Commun., 7, 768 (2006); doi:10.1016/j.catcom.2006.03.002.
- P.T. Patil, K.M. Malshe, P. Kumar, M.K. Dongare and E. Kemnitz, Catal. Commun., 3, 411 (2002); doi:10.1016/S1566-7367(02)00160-7.
- P. Laidlaw, D. Bethell, S.M. Brown and G.J. Hutchings, J. Mol. Catal. A, 174, 187 (2001); doi:10.1016/S1381-1169(01)00164-9.
- D.Q. Zhou, Y.H. Zhang, M.Y. Huang and Y.Y. Jiang, Polym. Adv. Technol., 14, 360 (2003); doi:10.1002/pat.321.
- V.I. Parvulescu and C. Hardacre, Chem. Rev., 107, 2615 (2007); doi:10.1021/cr050948h.
- (a) P. Wasserscheid and T. Welton, Ionic Liquids in Synthesis, Wiley-VCH, Weinheim, edn 2 (2008); (b) C. Chiappe and D. Pieraccini, J. Phys. Org. Chem., 18, 275 (2005); doi:10.1002/poc.863.
- R. Sheldon, Chem. Commun., 2399 (2001); doi:10.1039/b107270f.
- J.G. Huddleston and R.D. Rogers, Chem. Commun., 1765 (1998); doi:10.1039/a803999b.
- Z. Liu, Z.C. Chen and Q.G. Zheng, Org. Lett., 5, 3321 (2003); doi:10.1021/ol0351549.
- 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.
References
G. Olah, in Friedel-Crafts and Related Reactions, Wiley Interscience: New York and London, Vols. I-IV (1963-1964).
H. Szmant, Organic Building Blocks of the Chemical Industry, Wiley, New York (1989).
J. March, Advanced Organic Chemistry, Wiley, New York, edn 4 (1992).
C. Hardacre, S.P. Katdare, D. Milroy, P. Nancarrow, D.W. Rooney and J.M. Thompson, J. Catal., 227, 44 (2004); doi:10.1016/j.jcat.2004.05.034.
S.K. Jana, Catal. Surv. Asia, 9, 25 (2005); doi:10.1007/s10563-005-3335-y.
C. Paun, C. Stere, S.M. Coman, V.I. Parvulescu, P. Goodrich and C. Hardacre, Catal. Today, 131, 98 (2008); doi:10.1016/j.cattod.2007.10.028.
V.N. Sheemol, B. Tyagi and R.V. Jasra, J. Mol. Catal. A., 215, 201 (2004); doi:10.1016/j.molcata.2004.02.002.
G. Wine, C. Pham-Huu and M. Ledoux, Catal. Commun., 7, 768 (2006); doi:10.1016/j.catcom.2006.03.002.
P.T. Patil, K.M. Malshe, P. Kumar, M.K. Dongare and E. Kemnitz, Catal. Commun., 3, 411 (2002); doi:10.1016/S1566-7367(02)00160-7.
P. Laidlaw, D. Bethell, S.M. Brown and G.J. Hutchings, J. Mol. Catal. A, 174, 187 (2001); doi:10.1016/S1381-1169(01)00164-9.
D.Q. Zhou, Y.H. Zhang, M.Y. Huang and Y.Y. Jiang, Polym. Adv. Technol., 14, 360 (2003); doi:10.1002/pat.321.
V.I. Parvulescu and C. Hardacre, Chem. Rev., 107, 2615 (2007); doi:10.1021/cr050948h.
(a) P. Wasserscheid and T. Welton, Ionic Liquids in Synthesis, Wiley-VCH, Weinheim, edn 2 (2008); (b) C. Chiappe and D. Pieraccini, J. Phys. Org. Chem., 18, 275 (2005); doi:10.1002/poc.863.
R. Sheldon, Chem. Commun., 2399 (2001); doi:10.1039/b107270f.
J.G. Huddleston and R.D. Rogers, Chem. Commun., 1765 (1998); doi:10.1039/a803999b.
Z. Liu, Z.C. Chen and Q.G. Zheng, Org. Lett., 5, 3321 (2003); doi:10.1021/ol0351549.
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.