Acylation of salicylamide to 5-acetylsalicylamide using ionic liquids as dual catalyst and solvent

Weiguang Chen; Hengbo Yin; Yunsheng Zhang; Zhangzhun Lu; Aili Wang; Yutang Shen; Tingshun Jiang; Longbao Yu

Journal of Industrial and Engineering Chemistry, Vol.16, No.5, 800-804, September, 2010

DOI10.1016/j.jiec.2010.05.009 Export Citation

Acylation of salicylamide to 5-acetylsalicylamide using ionic liquids as dual catalyst and solvent

Weiguang Chen, Hengbo Yin^†, Yunsheng Zhang, Zhangzhun Lu, Aili Wang, Yutang Shen, Tingshun Jiang, and Longbao Yu

Faculty of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, China

E-mail:

The Lewis acidic ionic liquids, 1-butyl-3-methylimidazolium chloroaluminate ([BMIM]Cl-nAlCl3) and Nbutylpyridinium chloroaluminate ([BPy]Cl-nAlCl3), were used as both catalyst and solvent in Friedel. Crafts acylation of salicylamide with acetyl chloride to 5-acetylsalicylamide. The Lewis acidic ionic liquids, substituting for the conventional carcinogenic nitrobenzene solvent and anhydrous AlCl3 catalyst, showed excellent catalytic activity in the acylation of salicylamide to 5-acetylsalicylamide. When [BMIM]Cl-2AlCl3 was used as the catalyst, the yield of 5-acetylsalicylamide reached 81.3%. When [BPy]-2AlCl3 was used as the catalyst, the maximum yield of 5-acetylsalicylamide was 89.2%. The content of AlCl3 and the structure of the cations in the ionic liquids had synergistic effect on the acylation reaction.

Keywords:5-Acetylsalicylamide;Friedel-Crafts acylation;Lewis acidic ionic liquids;Salicylamide

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[Referenced By]

[1] Jang DO, Moon KS, Cho DH, Kim J, Tetrahedron Lett., 47, 6063 (2006)

[2] Yue CB, Yi TF, Zhu CB, Liu G, J. Ind. Eng. Chem., 15(5), 653 (2009)

[3] Castro C, Corma A, Primo J, J. Mol. Catal. A-Chem., 177(2), 273 (2002)

[4] Li H, Wang H, Sun H, Liu Y, Liu K, Peng S, Toxicol. Lett., 139, 25 (2003)

[5] Yadav GD, Nalawade SP, Chem. Eng. Sci., 58(12), 2573 (2003)

[6] Andy P, Garcia-Martinez J, Lee G, Gonzalez H, Jones CW, Davis ME, J. Catal., 192(1), 215 (2000)

[7] Nawaz Z, Qing S, Jixian G, Tang X, Wei F, J. Ind. Eng. Chem., 16(1), 57 (2010)

[8] Heidekum A, Harmer MA, Hoelderich WF, J. Catal., 188(1), 230 (1999)

[9] Kozhevnikov IV, Appl. Catal. A: Gen., 256(1-2), 3 (2003)

[10] Li Z, Jia Z, Luan Y, Mu T, Curr. Opin. Solid State Mater. Sci., 12, 1 (2008)

[11] Duan ZY, Gu YL, Zhang J, Zhu LY, Deng YQ, J. Mol. Catal. A-Chem., 250(1-2), 163 (2006)

[12] Olivier-Bourbigou H, Magna L, J. Mol. Catal. A-Chem., 182(1), 419 (2002)

[13] Chen M, Huang LJ, Luo Y, He MQ, Xie JM, Yuan XH, React. Kinet. Catal. Lett., 98(2), 355 (2009)

[14] Yeung KS, Qiu Z, Farkas ME, Xue Q, Regueiro-Ren A, Yang Z, Bender JA, Good AC, Kadow JF, Tetrahedron Lett., 49, 6250 (2008)

[15] Yuan XH, Chen M, Dai QX, Cheng XN, Chem. Eng. J., 146(2), 266 (2009)

[16] Xiao Y, Malhotra SV, J. Organomet. Chem., 690, 3609 (2005)

[17] Fang D, Cheng J, Gong K, Shi QR, Zhou XL, Liu ZL, J. Fluorine Chem., 129, 108 (2008)

[18] Yeung KS, Farkas ME, Qiu Z, Yang Z, Tetrahedron Lett., 43, 5793 (2002)

[19] Valkenberg MH, deCastro C, Holderich WF, Appl. Catal. A: Gen., 215(1-2), 185 (2001)

[20] Yang Y, Kou Y, Chem. Commun., 226 (2004)

[21] Wilkes JS, Levisky JA, Wilson RA, Hussey CL, Inorg. Chem., 21, 1263 (1982)

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