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C12 - C18脂肪酸异冰片酯的合成

Synthesis of C12-C18 Fatty Acid Isobornyl Esters.

作者信息

Qin Rongxiu, Chen Haiyan, Wen Rusi, Liang Zhongyun, Meng Zhonglei

机构信息

Guangxi Key Laboratory of Superior Timber Trees Resource Cultivation, Guangxi Forestry Research Institute, Nanning 530002, China.

出版信息

Molecules. 2023 Nov 9;28(22):7510. doi: 10.3390/molecules28227510.

DOI:10.3390/molecules28227510
PMID:38005232
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10673531/
Abstract

Camphene, C12-C18 fatty acids, and titanium sulfate were used as raw materials to study the synthesis of long-chain fatty acid isobornyl esters. Products were analyzed quantitatively by gas chromatography (GC), characterized by nuclear magnetic resonance spectroscopy (hydrogen and carbon), and evaluated using toxicity tests. The optimum reaction conditions were as follows: n(lauric acid):n(camphene) = 2.5:1, m(titanium sulfate):m(camphene) = 0.25:1, reaction temperature of 80 °C, and reaction time of 25 h. Under these conditions, the content of isobornyl laurate in the product was 74.49%, and the content of purified product was 95.02%. The reaction kinetics for isobornyl laurate showed an apparent first-order reaction in the first 9 h with an activation energy of 31.01 kJ/mol. The reaction conditions of myristic acid, palmitic acid, and stearic acid were similar to those of lauric acid, but the reaction time had to be increased as the molecular weight of the fatty acid increased. Toxicity tests for four types of long-chain fatty acid isobornyl esters showed that the samples had low toxicity.

摘要

以莰烯、C12 - C18脂肪酸和硫酸钛为原料,研究长链脂肪酸异冰片酯的合成。产物通过气相色谱(GC)进行定量分析,通过核磁共振光谱(氢谱和碳谱)进行表征,并通过毒性试验进行评估。最佳反应条件如下:n(月桂酸)∶n(莰烯)=2.5∶1,m(硫酸钛)∶m(莰烯)=0.25∶1,反应温度80℃,反应时间25 h。在此条件下,产物中月桂酸异冰片酯的含量为74.49%,纯化产物的含量为95.02%。月桂酸异冰片酯的反应动力学在最初9 h表现为明显的一级反应,活化能为31.01 kJ/mol。肉豆蔻酸、棕榈酸和硬脂酸的反应条件与月桂酸相似,但随着脂肪酸分子量的增加,反应时间必须延长。四种长链脂肪酸异冰片酯的毒性试验表明,样品毒性较低。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6bf3/10673531/59e318aa7307/molecules-28-07510-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6bf3/10673531/d66cbdea1919/molecules-28-07510-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6bf3/10673531/2d248dbaebdb/molecules-28-07510-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6bf3/10673531/743678995f21/molecules-28-07510-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6bf3/10673531/59e318aa7307/molecules-28-07510-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6bf3/10673531/d66cbdea1919/molecules-28-07510-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6bf3/10673531/2d248dbaebdb/molecules-28-07510-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6bf3/10673531/743678995f21/molecules-28-07510-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6bf3/10673531/59e318aa7307/molecules-28-07510-g004.jpg

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