通过酯化反应，用酰氯法高效合成 4,4-二甲基甾醇油酸酯。

Highly efficient synthesis of 4,4-dimethylsterol oleates using acyl chloride method through esterification.

机构信息

Collaborative Innovation Center of Food Safety and Quality Control in Jiangsu Province, National Engineering Research Center for Functional Food, School of Food Science and Technology, Jiangnan University, Wuxi 214122, China; School of Biological and Food Engineering, Anhui Polytechnic University, Wuhu 241000, China.

出版信息

Food Chem. 2021 Dec 1;364:130140. doi: 10.1016/j.foodchem.2021.130140. Epub 2021 May 18.

DOI:10.1016/j.foodchem.2021.130140

PMID:34175623

Abstract

In this study, the 4,4-dimethylsterol oleates were efficiently synthesized through esterification of 4,4-dimethylsterols and oleoyl chloride. The impact of reaction parameters on the 4,4-dimethylsterol conversion were investigated. The 4,4-dimethylsterol conversion increased with pyridine dosage, molar ratio of oleoyl chloride to 4,4-dimethylsterols, and temperature. The highest conversion of 99.27% was obtained with molar ratio of 1.1:1 at 313 K for 60 min. A second-order kinetic model describing acyl chloride esterification featuring high correlation coefficients was established. Arrhenius-Van't Hoff plot suggested activation energy and pre-exponential factor were 15.54 kJ mol and 1.78 × 10 L mol min, respectively. The molecular structure of 4,4-dimethylsterol oleates were finally identified by attenuated total reflection fourier transform infrared spectroscopy (ATR-FTIR), ultra-performance liquid chromatography system coupled with quadrupole time of flight mass spectrometry (UPLC-Q-TOF-MS), and nuclear magnetic resonance (NMR).

摘要

在这项研究中，通过 4,4-二甲基甾醇和油酰氯的酯化反应，高效合成了 4,4-二甲基甾醇油酸酯。考察了反应参数对 4,4-二甲基甾醇转化率的影响。4,4-二甲基甾醇转化率随着吡啶用量、油酰氯与 4,4-二甲基甾醇的摩尔比和温度的增加而增加。在 313 K 下，反应 60 min，摩尔比为 1.1:1 时，转化率最高可达 99.27%。建立了描述酰氯酯化反应的二阶动力学模型，相关系数较高。阿仑尼乌斯-范特霍夫图表明，活化能和指前因子分别为 15.54 kJ/mol 和 1.78×10 L/mol·min。最后通过衰减全反射傅里叶变换红外光谱（ATR-FTIR）、超高效液相色谱系统与四极杆飞行时间质谱联用（UPLC-Q-TOF-MS）和核磁共振（NMR）确定了 4,4-二甲基甾醇油酸酯的分子结构。