应用化学2016，Vol.33Issue(11)：1265-1273,9.DOI:10.11944/j.issn.1000-0518.2016.11.160017
烷基-α-D-吡喃葡萄糖苷的合成与性能
Synthesis and Properties of Alkyl α-D-Glucopyranosides
摘要
Abstract
Alkyl α-D-glucopyranosides were synthesized with D-glucose as the raw material by three reactions involving acetylation , SnCl 4 catalyzing glycosylation with the aliphatic alcohols and deacetylation . The structures of alkyl α-D-glucopyranosides , their surface properties and thermotropic liquid crystalline properties were determined through NMR , surface tensiometer , polarization microscope and so on .The results show that alkyl α-D-glucopyranosides possess foaming and emulsifying power as their hydrophobic alkyl chain length n=6~9 , wherein n-nonyl α-D-glucopyranoside has rather superior foaming and emulsifying power .The values of the surface tension (γCMC ) and the critical micelle concentration ( CMC) of the alkyl glycosides ( n=6~9) are very low, their saturated adsorption capacity (Γmax ) decreases with increasing alkyl chain length , and their saturation adsorption area ( Amin ) increases with the increase of alkyl chain lengths .The standard free energy of micellization(ΔGmic ) and standard free energy of adsorption (ΔGads ) for alkyl glycosides ( n=6~9) are all less than zero, and the values of ΔGmic andΔGads are more negative with the increase of the alkyl chain length . The n-octyl α-D-glucopyranoside has the best surface activity .Furthermore, the alkyl glucosides(n=4~9) does not have any skin irritation .Finally, all of alkyl α-D-glucopyranosides exhibit thermotropic liquid crystalline behavior , the temperature range of the thermotropic liquid crystalline phase becomes broader , and the stability of the thermotropic liquid crystalline phase becomes stronger with the increase of alkyl chain length.关键词
D-葡萄糖/烷基-α-D-吡喃葡萄糖苷/SnCl4/表面性能/热致液晶Key words
D-glucose/alkyl α-D-glucopyranoside/SnCl4/surface performance/thermotropic liquid crystallline分类
化学化工引用本文复制引用
李贞操,陈国勇,陈朗秋,申望珍,季善伟..烷基-α-D-吡喃葡萄糖苷的合成与性能[J].应用化学,2016,33(11):1265-1273,9.基金项目
湖南省自然科学基金资助项目（10JJ6023，05JJ40054，14JJ2067）Supported by the Natural Science Foundation of Hunan Province of China （）
