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

摘要

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. ¹³C and ¹H 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 ¹³C and ¹H NMR respectively.