Synthesis of 5-benzoylacenaphthene in the presence of Lewis acidic ionic liquids

Min Chen; Di Li; Ying Luo; Minqiang He; Jimin Xie; Huamin Li; Xinhua Yuan

Journal of Industrial and Engineering Chemistry, Vol.17, No.1, 14-17, January, 2011

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Synthesis of 5-benzoylacenaphthene in the presence of Lewis acidic ionic liquids

Min Chen^†, Di Li, Ying Luo, Minqiang He, Jimin Xie, Huamin Li, and Xinhua Yuan¹

School of Chemistry and Chemical Engineering, Jiangsu University, 301 Xuefu Road, Zhenjiang 212013, Jiangsu, PR China
¹School of Material Science and Engineering, Jiangsu University, 301 Xuefu Road, Zhenjiang 212013, Jiangsu, PR China

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Acylation of acenaphthene with benzoyl chloride to 5-benzoylacenaphthene catalyzed by various Lewis acidic ionic liquids (ILs) was investigated. Ionic liquids of different alkyl chain length and metal chloride were synthesized and tested for the reaction to discuss the effects of Lewis acidity of the ionic liquid on the synthesis of 5-benzoylacenaphthene. Pure 5-benzoylacenaphthene was obtained and its structure was identified by GC/MS, FT-IR and 1H NMR spectra. [Emim]Cl/AlCl3 ionic liquid was found to be the most active catalyst in the acylation. The yield of 5- benzoylacenaphthene was up to 87% and the regioselectivity towards 5-benzoylacenaphthene was up to 90%. The experimental resulted show that [Emim]Cl/AlCl3 can be used as both catalyst and solvent, and it is reusable and environmentally friendly for the preparation of 5-benzoylacenaphthene.

Keywords:Lewis acidic ionic liquid;5-Benzoylacenaphthene;Acenaphthene;Acylation;Benzoyl chloride

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[2] Lund T, Lundgren B, Lund H, Acta Chem. Scand., 49, 755 (1995)

[3] Kim DJ, Kim JW, Choung SJ, Kang M, J. Ind. Eng. Chem., 14(3), 308 (2008)

[4] Dealmeida JL, Dufaux M, Taarit YB, Naccache C, Appl. Catal. A: Gen., 114(1), 141 (1994)

[5] Han MH, Cui Z, Xu C, Chen W, Jin Y, Appl. Catal. A: Gen., 238(1), 99 (2003)

[6] Namuangruk S, Pantu P, Limtrakul J, J. Catal., 225(2), 523 (2004)

[7] Lenarda M, Storaro L, Pellegrini G, Piovesan L, Ganzerla R, J. Mol. Catal. A., 145, 237 (1999)

[8] Angelis A, Amarilli S, Berti D, Montanari L, Perego C, J. Mol. Catal. A., 146, 37 (1999)

[9] Sebusky RT, Henke AM, Ind. Eng. Chem. Process Res. Dev., 2, 272 (1971)

[10] Xie XG, Lu JP, Chen B, Tetrahedron Lett., 45, 809 (2004)

[11] Baleizao C, Pires N, Gigante B, Tetrahedron Lett., 45, 4375 (2004)

[12] Boon JA, Levisky JA, Pflug JL, J. Org. Chem., 51, 480 (1986)

[13] Hardacre C, Katdare SP, Milroy D, Nancarrow P, Rooney DW, Thompson JM, J. Catal., 227(1), 44 (2004)

[14] Adams CJ, Earle MJ, Seddon KR, Chem. Commun., 19, 2097 (1998)

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[17] Nara SJ, Harjani JR, Salunkhe MM, J. Org. Chem., 66, 8616 (2001)

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[19] Reichardt C, Federal Republic of Germany, VCH, Weinheim, p. 248. (1988)

[20] Xin HL, Wu Q, Han MH, Wang DZ, Jin Y, Appl. Catal. A: Gen., 292, 354 (2005)

[21] Howarth J, Hanlon K, Fayne D, McCormac P, Tetrahedron Lett., 38, 3097 (1997)

[22] Ya KS, Namboodiri VV, Varma RS, Smirniotis PG, J. Catal., 222(2), 511 (2004)

[23] Matsumoto T, Ichikawa K, J. Am. Chem. Soc., 106, 4316 (1984)