王秀华1,杨瑞楠1,刘君1,2,梁少华1,刘伟1.化学法合成不饱和脂肪酸植物
甾烷醇酯工艺研究[J].中国油脂,2025,50(9):.[WANG Xiuhua1, YANG Ruinan1, LIU Jun1,2, LIANG Shaohua1, LIU Wei1.Synthesis of unsaturated fatty acid phytostanol esters by chemical method[J].China Oils and Fats,2025,50(9):.] |
化学法合成不饱和脂肪酸植物
甾烷醇酯工艺研究 |
Synthesis of unsaturated fatty acid phytostanol esters by chemical method |
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DOI:10.19902/j.cnki.zgyz.1003-7969.240280 |
中文关键词: 植物甾烷醇 不饱和脂肪酸 化学法 植物甾烷醇酯 |
英文关键词:phytostanol unsaturated fatty acid chemical method phytostanol esters |
基金项目:国家自然科学基金面上项目(31972110) |
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Author Name | Affiliation | WANG Xiuhua1, YANG Ruinan1, LIU Jun1,2, LIANG Shaohua1, LIU Wei1 | 1.College of Food Science and Engineering, Henan University of Technology, Zhengzhou 450001, China
2.National Engineering Research Center for Wheat and Corn Further Processing, Henan University of
Technology, Zhengzhou 450001, China |
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中文摘要: |
旨在为植物甾烷醇酯的开发和应用提供技术支撑,以植物甾烷醇和酰基供体为原料,合成不饱和脂肪酸植物甾烷醇酯,并通过溶剂萃取、柱层析等对产物进行分离纯化。通过单因素实验考察了酰基供体类型(不饱和脂肪酸、油酸甲酯、三油酸甘油酯)、催化剂种类、反应温度、催化剂用量、底物物质的量比、反应时间等因素对植物甾烷醇转化率的影响。测定了不饱和脂肪酸植物甾烷醇酯产品的纯度、反式脂肪酸含量,通过核磁共振波谱和傅里叶变换红外光谱对产品的结构进行了鉴定。结果表明:以不饱和脂肪酸为酰基供体时,植物甾烷醇的转化率高;以4-十二烷基苯磺酸(DBSA)为催化剂,在DBSA用量10%(以植物甾烷醇物质的量计)、酸醇物质的量比3∶ 1、反应时间12 h、氮气作保护气的条件下,分别在反应温度60 ℃和90 ℃下合成植物甾烷醇油酸酯和植物甾烷醇亚油酸酯,植物甾烷醇转化率分别为95.45%和93.60%;植物甾烷醇油酸酯和植物甾烷醇亚油酸酯产品纯度分别达97.43%和94.98%,且不含反式脂肪酸;核磁共振波谱和傅里叶变换红外光谱确证了目标产物的合成。综上,在无溶剂和较低温度(≤90 ℃)下实现了不饱和脂肪酸植物甾烷醇酯的高效合成。 |
英文摘要: |
To provide technical support for the development and application of phytostanol esters, the unsaturated fatty acid phytostanol esters were synthesized from phytostanol and acyl donors, and then the product was obtained by isolation and purification with solvent extraction and column chromatography. The effects of acyl donor type (unsaturated fatty acid, methyl oleate, triolein glycerol ester), catalyst type, reaction temperature, catalyst dosage, substrate molar ratio, and reaction time on conversion rate of phytostanol were investigated by single factor experiment. The purity and trans fatty acids content of the product were analyzed, and the structures of the product were identified by NMR and FTIR. The results showed that using unsaturated fatty acids as acyl donors resulted in a high conversion rate of phytostanol. With 4-dodecyl benzene sulfonic acid (DBSA) as the catalyst, under the conditions of 10% DBSA (calculated based on the molar of phytostanol), molar ratio of fatty acid to phytostanol 3∶ 1, reaction time 12 h, nitrogen as protection gas, the phytostanol oleate and linoleate were synthesized at the reaction temperature of 60 ℃ and 90 ℃, with the phytostanol conversion rates of 95.45% and 93.60%, respectively. The purity of phytostanol oleate and phytostanol linoleate reached 97.43% and 94.98%, respectively, and no trans fatty acids were detected. NMR and FTIR confirmed the synthesis of the target products. In general, the efficient synthesis of unsaturated fatty acid phytostanol esters can be achieved under solvent-free and low temperature (≤90 ℃) conditions. |
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