Optimization of the chemoenzymatic mono-epoxidation of linoleic acid using D-optimal design

Mono-epoxied linoleic acid 9(12)-10(13)-monoepoxy 12(9)-octadecanoic acid (meoa) was synthesized and optimized by immobilized candida antarctica lipase (novozym 435®) using d-optimal design. for optimizing the reaction,response surface methodology (rsm) was employed with four reaction variables such as the effect of amount of hydrogen peroxide (μl),amount of enzyme (w) and reaction time (h). at optimum conditions the experiment to obtain a higher yield% with a medium ooc% of meoa was predicted at an amount of h2o2 μl of 15,novozym 435® of 0.12g and 7h of reaction time. at this condition,the yield of meoa was 82.14%,4.91% of ooc and 66.65mg/g of iodine value (iv). the observed value was reasonably close to the predicted value. hydrogen peroxide was found to have the most significant effect on the degree of epoxidation ooc% and yield%. the epoxy ring opening (-c-o-c-) has been observed by fourier transform infrared spectroscopy (ftir) at 820cm-1 and the double band (-cc-) at 3009cm-1. 1h nmr analyses confirmed that the oxirane ring (-ch-o-ch-) of meoa at 2.92-3.12ppm and four signals of methane (-chch-) was at 5.38-5.49ppm while the 13c nmr showed the oxirane ring (-c-o-c-) at 54.59-57.29ppm and the olefinic carbons at 124.02-132.89ppm. © 2011.