Preparation and Physical Properties of Chitosan Benzoic Acid Derivatives Using a Phosphoryl Mixed Anhydride System

Molecules

Duckhee Lee¹  Zhe Shan Quan¹  Chichong Lu¹  Jin Ah Jeong¹  Changhyun Song¹  Mi-Sun Song¹ 

[1] ¹The Division of Bio-Nanochemistry, The College of Natural Sciences, The Wonkwang University, Iksan City, Chonbuk, 570-749, Korea ²College of Pharmacy, Yanbian University, Yanji 133000, China

关键词: acylation;    chitosan benzoate;    benzoic acid;    trifluoroacetic anhydride;    phosphoric acid;   

DOI  :  10.3390/molecules17022231

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.