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Preparation and Physical Properties of Chitosan Benzoic Acid Derivatives Using a Phosphoryl Mixed Anhydride System
The Division of Bio-Nanochemistry, The College of Natural Sciences, The Wonkwang University, Iksan City, Chonbuk, 570-749, Korea
College of Pharmacy, Yanbian University, Yanji 133000, China
* Author to whom correspondence should be addressed.
Received: 1 January 2012; in revised form: 15 February 2012 / Accepted: 16 February 2012 / Published: 22 February 2012
Abstract: Direct benzoylation of the two hydroxyl groups on chitosan was achieved using a phosphoryl mixed anhydride system, derived from trifluoroacetic anhydride (TFAA), benzoic acids (BAs), and phosphoric acid (PA). The reaction is operated as a one pot process under mild conditions that does not require neither an inert atmosphere nor dry solvents. The structures of the synthesized compounds were confirmed by NMR and IR spectroscopy. Solubility tests on the products revealed that they were soluble in organic solvents such as N,N-dimethylformamide (DMF), dimethylsulfoxide (DMSO), and acetone. In the meantime, a morphological study by scanning electron microscopy (SEM) evidently indicated that the chitosan benzoates underwent significant structural changes after the benzoylation.
Keywords: acylation; chitosan benzoate; benzoic acid; trifluoroacetic anhydride; phosphoric acid
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Lee, D.; Quan, Z.S.; Lu, C.; Jeong, J.A.; Song, C.; Song, M.-S.; Chai, K.Y. Preparation and Physical Properties of Chitosan Benzoic Acid Derivatives Using a Phosphoryl Mixed Anhydride System. Molecules 2012, 17, 2231-2239.
Lee D, Quan ZS, Lu C, Jeong JA, Song C, Song M-S, Chai KY. Preparation and Physical Properties of Chitosan Benzoic Acid Derivatives Using a Phosphoryl Mixed Anhydride System. Molecules. 2012; 17(2):2231-2239.
Lee, Duckhee; Quan, Zhe Shan; Lu, Chichong; Jeong, Jin Ah; Song, Changhyun; Song, Mi-Sun; Chai, Kyu Yun. 2012. "Preparation and Physical Properties of Chitosan Benzoic Acid Derivatives Using a Phosphoryl Mixed Anhydride System." Molecules 17, no. 2: 2231-2239.