Malaysian Journal of Analytical Sciences Vol 19 No 1 (2015): 144 – 154

 

 

 

Optimization of the in situ Epoxidation of linoleic acid of Jatropha curcas oil with performic acid

 

(Pengoptimuman Tindakbalas Pengepoksidaan in situ Asid Linoleik Minyak Jatropha curcas dengan Asid Performik)

 

Liew Kin Hong, Rahimi M. Yusop, Nadia Salih,  Jumat Salimon*

 

School of Chemical Sciences and Food Technology,

Faculty of Science and Technology,

Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia

 

*Corresponding author: jumat@ukm.edu.my

 

 

Abstract

The aim of this study is to optimise the epoxidation of linoleic acid of Jatropha curcas oil. This experiment was carried out with performic acid generated in situ by using hydrogen peroxide and formic acid. The method was evaluated on different parameters such as reaction temperature, mole ratios of formic acid to ethylenic unsaturation and hydrogen peroxide to ethylenic unsaturation. The optimum relative conversion into oxirane (80.4%) and conversion of iodine (94.7%) was achieved with ~70 % yield at the condition of 45°C reaction temperature, formic acid to ethylenic unsaturation mole ratio of 2.0, hydrogen peroxide to ethylenic unsaturation mole ratio of 12.0 for 2 hours of reaction time. The epoxidized linoleic acid was characterized by using Fourier transform infrared (FTIR) spectroscopy and NMR analysis. The result was also found that the formations of an epoxide and oxirane ring cleavage were both occurred at the same time if low amount of hydrogen peroxide was used.

 

Keywords:  epoxidation, linoleic acid, Jatropha curcus oil, performic acid

 

Abstrak

Kajian pengoptimuman tindak balas pengepoksidaan asid linoleik minyak Jatropha curcas telah dilakukan. Tindak balas ini dijalankan menggunakan asid performik yang dijana secara in situ dengan menggunakan hidrogen peroksida dan asid formik. Kaedah ini telah dinilai dengan beberapa  jenis parameter seperti suhu tindak balas, nisbah mol asid formik kepada etilenik taktepu dan nisbah mol hidrogen peroksida kepada etilenik taktepu. Penukaran relatif optimum kepada oksirana (80.4%) dan penukaran relatif nilai iodin (94.7%) telah dicapai dengan ~ 70 % hasil pada keadaan suhu tindak balas 45°C, nisbah mol asid formik kepada etilenik taktepu 2.0, nisbah mol hidrogen peroksida kepada etilenik taktepu 12.0 pada masa tindak balas selama 2 jam. Asid linoleik terepoksida dicirikan dengan menggunakan spektroskopi inframerah transformasi Fourier (FTIR) dan analisis spektroskopi resonans magnet nukleus (NMR). Hasil kajian juga mendapati bahawa pembentukan gelang oksirana dan pembukaan gelang oksirana telah berlaku serentak pada masa yang sama jika amaun hidrogen peroksida yang rendah telah digunakan.

 

Kata Kunci: pengepoksidaan, asid linoleik, minyak Jatropha curcus, asid performik

 

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