对甲苯磺酸催化下亚油酸单环氧化物的合成与开环优化

Synthesis and optimization ring opening of monoepoxide linoleic acid using p-toluenesulfonic acid.

作者信息

Salimon Jumat, Abdullah Bashar Mudhaffar, Yusop Rahimi M, Salih Nadia, Yousif Emad

机构信息

School of Chemical Sciences & Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 Bangi Selangor, Malaysia.

出版信息

Springerplus. 2013 Sep 2;2:429. doi: 10.1186/2193-1801-2-429. eCollection 2013.

DOI:10.1186/2193-1801-2-429

PMID:24083099

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3786081/

Abstract

Biolubricant base oils, 9,12-hydroxy-10,13-oleioxy-12-octadecanoic acid (HYOOA) was synthesized based on the esterification reaction of Monoepoxide linoleic acid 9(12)-10(13)-monoepoxy 12(9)-octadecanoic acid (MEOA) with oleic acid (OA) and catalyzed by p-Toluenesulfonic acid. The optimum conditions for the experiment using D-optimal design to obtain high yield% of 84.61, conversion% of 83.54 and lowest OOC% of 0.05 were predicted at OA/MEOA ratio of 0.2:1 (mol/mol), PTSA/MEOA ratio of 0.4:1 (mol/mol), reaction temperature at 110°C, and reaction time at 4.5 h. The FTIR peaks of HYOOA indicate the disappearance of the absorption band at 820 cm(-1), which belongs to the oxirane ring. (13)C and (1)H NMR spectra analyses confirmed the result of HYOOA with appearance carbon-ester (C = O) chemical shift at 174.1 ppm and at 4.06 ppm for (13)C and (1)H NMR respectively.

摘要

生物润滑剂基础油，9,12-二羟基-10,13-油酰氧基-12-十八烷酸（HYOOA）是基于单环氧化亚油酸9(12)-10(13)-单环氧化12(9)-十八烷酸（MEOA）与油酸（OA）的酯化反应合成的，并以对甲苯磺酸为催化剂。采用D-最优设计进行实验，预测在OA/MEOA摩尔比为0.2:1、PTSA/MEOA摩尔比为0.4:1、反应温度为110°C、反应时间为4.5小时的条件下，可获得84.61%的高产率、83.54%的转化率和0.05%的最低OOC%。HYOOA的傅里叶变换红外光谱（FTIR）峰表明，属于环氧乙烷环的820 cm⁻¹处的吸收带消失。碳-13（¹³C）和氢-1（¹H）核磁共振光谱分析证实了HYOOA的结果，¹³C和¹H核磁共振的羰基（C=O）化学位移分别出现在174.1 ppm和4.06 ppm处。