ISSN: 0256-1115 (print version) ISSN: 1975-7220 (electronic version)
Copyright © 2024 KICHE. All rights reserved

Articles & Issues

Language
English
Conflict of Interest
In relation to this article, we declare that there is no conflict of interest.
Publication history
Received February 24, 2009
Accepted April 12, 2009
articles This is an Open-Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/bync/3.0) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
Copyright © KIChE. All rights reserved.

All issues

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

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
chenmin3226@sina.com
Korean Journal of Chemical Engineering, November 2009, 26(6), 1563-1567(5), 10.1007/s11814-009-0257-9
downloadDownload PDF

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.

References

Bandini M, Melloni A, Umani-Rouchi A, Angew. Chem. Int. Ed., 43, 550 (2004)
Qiao CZ, Zhang YF, Zhang JC, Li CY, Appl. Catal. A: Gen., 276(1-2), 61 (2004)
Ghiaci M, Abbaspur A, Arshadi M, Aghabarari B, Appl. Catal. A: Gen., 316(1), 32 (2007)
Sivasnaker S, Thangaraj A, J. Catal., 138, 386 (1992)
Dealmeida JL, Dufaux M, Taarit YB, Naccache C, Appl. Catal. A: Gen., 114(1), 141 (1994)
Han MH, Cui Z, Xu C, Chen W, Jin Y, Appl. Catal. A: Gen., 238(1), 99 (2003)
Namuangruk S, Pantu P, Limtrakul J, J. Catal., 225(2), 523 (2004)
Lenarda M, Storaro L, Pellegrini G, Piovesan L, Ganzerla R, J. Mol. Catal. A, 145, 237 (1999)
Angelis A, Amarilli S, Berti D, Montanari L, Perego C, J. Mol. Catal. A, 146, 37 (1999)
Sebusky RT, Henke AM, Ind. Eng. Chem. Process Res., Dev., 2, 272 (1971)
Xu W, Tong H, Chen C, Xu X, Korean J. Chem. Eng., 25(1), 53 (2008)
Howarth J, James P, Dai JF, Tetrahedron Lett., 41, 10319 (2000)
Xie XG, Lu JP, Chen B, Tetrahedron Lett., 45, 809 (2004)
Yadav JS, Reddy BVS, Basak AK, Tetrahedron Lett., 44, 2217 (2003)
Baleizao C, Pires N, Gigante B, Tetrahedron Lett., 45, 4375 (2004)
Xiao Y, Malhotra SV, Tetrahedron Lett., 45, 8339 (2004)
Boon JA, Levisky JA, Pflug JL, J. Org. Chem., 51, 480 (1986)
Qiao CZ, Zhang YF, Zhang JC, Li CY, Appl. Catal. A: Gen., 276(1-2), 61 (2004)
Blanco CG, Banciella DC, Azpiroz MDG, J. Mol. Catal. A-Chem., 253(1-2), 203 (2006)
Zhao ZK, Qiao WH, Wang XN, Wang GR, Li ZS, Cheng LB, Appl. Catal. A: Gen., 290(1-2), 133 (2005)
Wasserscheid P, Keim W, Angew. Chem. Int. Ed., 39, 3772 (2000)
Jonathan GH, Ann EV, Reichert WM, Green Chem., 31, 56 (2001)
Adams CJ, Earle MJ, Seddon KR, Chem. Commum., 19, 2097 (1998)
Huddleston JG, Visser AE, Reichert WM, Willauer HD, Broker GA, Rogers RD, Green Chem., 3, 156 (2001)
Welton T, Chem. Rev., 99(8), 2071 (1999)
Nara SJ, Harjani JR, Salunkhe MM, J. Org. Chem., 66, 8616 (2001)
Vogel P, Carbocation chemistry, elsevier amsterdam, 444 (1985)
Reichardt C, Federal republic of germany VCH weinheim, 248 (1988)
Xin HL, Wu Q, Han MH, Wang DZ, Jin Y, Appl. Catal. A, 292, 354 (2005)
Howarth J, Hanlon K, Fayne D, McCormac P, Tetrahedron Lett., 38, 3097 (1997)
Ya KS, Namboodiri VV, Varma RS, Smirniotis PG, J. Catal., 222(2), 511 (2004)
Hussey CL, Mamantov G, Ed. Elsevier: Amsterdam, 5, 185 (1983)
Matsumoto T, Ichikawa K, J. Am. Chem. Soc., 106, 4316 (1984)
Gale RJ, Gilbert B, Osteryoung RA, Inorg. Chem., 17, 2728 (1978)
Rytter E, Øye HA, Cyvin SJ, Cyvin BN, Klaelboe PJ, Inorg. Nucl. Chem., 35, 1185 (1973)

The Korean Institute of Chemical Engineers. F5, 119, Anam-ro, Seongbuk-gu, 233 Spring Street Seoul 02856, South Korea.
TEL. No. +82-2-458-3078FAX No. +82-507-804-0669E-mail : kiche@kiche.or.kr

Copyright (C) KICHE.all rights reserved.

- Korean Journal of Chemical Engineering 상단으로