Preparation and Physical Properties of Chitosan Benzoic Acid Derivatives Using a Phosphoryl Mixed Anhydride System 英文参考文献.docVIP

Molecules 2012, 17, 2231-2239; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Communication Preparation and Physical Properties of Chitosan Benzoic Acid Derivatives Using a Phosphoryl Mixed Anhydride System Duckhee Lee 1, Zhe Shan Quan 2, Chichong Lu 1, Jin Ah Jeong 1, Changhyun Song 1, Mi-Sun Song 1 and Kyu Yun Chai 1,* 1 The Division of Bio-Nanochemistry, The College of Natural Sciences, The Wonkwang University, Iksan City, Chonbuk, 570-749, Korea; E-Mails: dl202@wonkwang.ac.kr (D.L.); chichonglu@ (C.L.); mi_in_black@ (J.A.J.); schh1004@ (C.S.); misun4y@ (M.-S.S.) 2 College of Pharmacy, Yanbian University, Yanji 133000, China; E-Mail: quanzheshan@ * Author to whom correspondence should be addressed; E-Mail: geuyoon@wonkwang.ac.kr; Tel.: +82-63-850-6230; Fax: +82-63-841-4893. 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  Molecules 2012, 17 2232 1. Introduction Chitin, the second abundant natural polymer