Zhongguo youzhi (Oct 2022)
超声辅助合成油脂基双亲性超分子Ultrasound-assisted synthesis of lipid-based amphiphilic supramolecules
Abstract
为充分利用油脂精炼过程中的皂脚，实现绿色油脂资源的高值化利用，以油酸钠为原料，超声辅助快速合成具有端环氧基的油酸缩水甘油酯，然后以端环氧基油酸缩水甘油酯为原料，与4-叔丁基杯\[4\]芳烃在酸性条件下发生开环反应，利用超声辅助快速合成兼具长链烷基疏水基和羟基亲水基的油脂基双亲性超分子。通过单因素实验研究了4-叔丁基杯\[4\]芳烃与端环氧基油酸缩水甘油酯物质的量比、超声时间、超声温度和超声功率对产物得率的影响，并采用FTIR和NMR进行产物结构表征。结果表明：油脂基双亲性超分子最佳合成条件为4-叔丁基杯\[4\]芳烃与端环氧基油酸缩水甘油酯物质的量比1∶ 6、超声时间150 min、超声温度50 ℃、超声功率100 W，在此条件下产物得率高达94%，该法比传统回流搅拌合成方法需要的反应时间更短，副产物更少；产物结构中含有醚氧键、羟基、长链烷基、不饱和双键和苯基，赋予超分子亲水和亲脂的双亲性能 In order to fully use the soapstock produced in the oil refining process and achieve the high-value utilization of renewable oil resources, sodium oleate was used as raw material to rapidly synthesize glycidyl oleate with epoxy terminated group assisted by ultrasound. Then the lipid-based amphiphilic supramolecules with both long chain alkyl hydrophobic group and hydroxyl hydrophilic group were rapidly synthesized by the acid catalysis ring opening reaction between glycidyl oleate with epoxy terminated group and 4-tert-butyl calix\[4\]arene using ultrasound-assisted method. The effects of molar ratio of 4-tert-butyl calix\[4\]arene to glycidyl oleate with epoxy terminated group, ultrasonic time, ultrasonic temperature and ultrasonic power on the product yield were studied by single factor experiment, and the product structure was characterized by FTIR and NMR. The results showed that the optimal synthesis conditions were obtained as follows: molar ratio of 4-tert-butyl calix\[4\]arene to glycidyl oleate with epoxy terminated group 1∶ 6, ultrasonic time 150 min, ultrasonic temperature 50 ℃, and ultrasonic power 100 W. Under the optimal conditions, the product yield was 94%. Compared with traditional reflux stirring synthesis method, ultrasound-assisted method required shorter reaction time and produced less by-products. FTIR and NMR analysis showed that the structure of the products contained aerobic ether bonds, hydroxyl groups, long alkyl chains, unsaturated double bonds and phenyl groups， which might endow supramolecules with amphipathic performance.
Keywords
