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

Bashar Mudhaffar Abdullah, Nadia Salih, Jumat Salimon

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)276-287
Number of pages12
JournalJournal of Saudi Chemical Society
Volume18
Issue number3
DOIs
Publication statusPublished - 2014

Fingerprint

Epoxidation
Linoleic Acid
Ethylene Oxide
Hydrogen Peroxide
Nuclear magnetic resonance
Candida
Methane
Lipase
Iodine
Carbon
stearic acid
Optimal design
Enzymes
Experiments
Novozyme 435

Keywords

  • D-optimal design
  • Linoleic acid
  • Mono-epoxidation
  • Novozym 435®

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Optimization of the chemoenzymatic mono-epoxidation of linoleic acid using D-optimal design. / Abdullah, Bashar Mudhaffar; Salih, Nadia; Salimon, Jumat.

In: Journal of Saudi Chemical Society, Vol. 18, No. 3, 2014, p. 276-287.

Research output: Contribution to journalArticle

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abstract = "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{\circledR}) 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{\circledR} 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.",
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N2 - 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.

AB - 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.

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