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Acylation of salicylamide to 5-acetylsalicylamide using ionic liquids as dual catalyst and solvent
Weiguang Chen,Yunsheng Zhang,Zhangzhun Lu,Aili Wang,Yutang Shen,Tingshun Jiang,Longbao Yu,Hengbo Yin 한국공업화학회 2010 Journal of Industrial and Engineering Chemistry Vol.16 No.5
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 AlCl3catalyst, 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. 2010 The Korean Society of Industrial and Engineering Chemistry. Published by Elsevier B.V. All rights reserved.