Alkylation of anthracene to 2-isopropylanthracene catalyzed by Lewis acid ionic liquids

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

Korean Journal of Chemical Engineering, Vol.26, No.6, 1563-1567, November, 2009

DOI10.1007/s11814-009-0257-9 Export Citation

Alkylation of anthracene to 2-isopropylanthracene catalyzed by Lewis acid ionic liquids

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

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

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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.

Keywords:Lewis Acidic Ionic Liquid;Alkylation;2-Isopropylanthracene;Anthracene;2-Chloropropane

[References]

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[2] Qiao CZ, Zhang YF, Zhang JC, Li CY, Appl. Catal. A: Gen., 276(1-2), 61 (2004)

[3] Ghiaci M, Abbaspur A, Arshadi M, Aghabarari B, Appl. Catal. A: Gen., 316(1), 32 (2007)

[4] Sivasnaker S, Thangaraj A, J. Catal., 138, 386 (1992)

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

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

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

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

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

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

[11] Xu W, Tong H, Chen C, Xu X, Korean J. Chem. Eng., 25(1), 53 (2008)

[12] Howarth J, James P, Dai JF, Tetrahedron Lett., 41, 10319 (2000)

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

[14] Yadav JS, Reddy BVS, Basak AK, Tetrahedron Lett., 44, 2217 (2003)

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

[16] Xiao Y, Malhotra SV, Tetrahedron Lett., 45, 8339 (2004)

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

[18] Qiao CZ, Zhang YF, Zhang JC, Li CY, Appl. Catal. A: Gen., 276(1-2), 61 (2004)

[19] Blanco CG, Banciella DC, Azpiroz MDG, J. Mol. Catal. A-Chem., 253(1-2), 203 (2006)

[20] Zhao ZK, Qiao WH, Wang XN, Wang GR, Li ZS, Cheng LB, Appl. Catal. A: Gen., 290(1-2), 133 (2005)

[21] Wasserscheid P, Keim W, Angew. Chem. Int. Ed., 39, 3772 (2000)

[22] Jonathan GH, Ann EV, Reichert WM, Green Chem., 31, 56 (2001)

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

[24] Huddleston JG, Visser AE, Reichert WM, Willauer HD, Broker GA, Rogers RD, Green Chem., 3, 156 (2001)

[25] Welton T, Chem. Rev., 99(8), 2071 (1999)

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

[27] Vogel P, Carbocation chemistry, elsevier amsterdam, 444 (1985)

[28] Reichardt C, Federal republic of germany VCH weinheim, 248 (1988)

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

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

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

[32] Hussey CL, Mamantov G, Ed. Elsevier: Amsterdam, 5, 185 (1983)

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

[34] Gale RJ, Gilbert B, Osteryoung RA, Inorg. Chem., 17, 2728 (1978)

[35] Rytter E, Øye HA, Cyvin SJ, Cyvin BN, Klaelboe PJ, Inorg. Nucl. Chem., 35, 1185 (1973)