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

Jumat Salimon, Bashar Mudhaffar Abdullah, Muhammad Rahimi Usop, Nadia Salih, Emad Yousif

Research output: Contribution to journalArticle

6 Citations (Scopus)

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. 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.

Original languageEnglish
Pages (from-to)1-14
Number of pages14
JournalSpringerPlus
Volume2
Issue number1
DOIs
Publication statusPublished - 2013

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Oleic Acid
Ethylene Oxide
Esterification
Fourier Transform Infrared Spectroscopy
4-toluenesulfonic acid
stearic acid
monoepoxide linoleic acid
Spectrum Analysis
Oils
Carbon
Temperature
Proton Magnetic Resonance Spectroscopy
Carbon-13 Magnetic Resonance Spectroscopy
calcium ascorbate
1,3,6,8-pyrene tetrasulfonate

ASJC Scopus subject areas

  • General

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Synthesis and optimization ring opening of Monoepoxide linoleic acid using p-toluenesulfonic acid. / Salimon, Jumat; Abdullah, Bashar Mudhaffar; Usop, Muhammad Rahimi; Salih, Nadia; Yousif, Emad.

In: SpringerPlus, Vol. 2, No. 1, 2013, p. 1-14.

Research output: Contribution to journalArticle

Salimon, Jumat ; Abdullah, Bashar Mudhaffar ; Usop, Muhammad Rahimi ; Salih, Nadia ; Yousif, Emad. / Synthesis and optimization ring opening of Monoepoxide linoleic acid using p-toluenesulfonic acid. In: SpringerPlus. 2013 ; Vol. 2, No. 1. pp. 1-14.
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