Sains Malaysiana 41(10)(2012): 1239–1244

Synthesis and Characterization of Esters Derived from Ricinoleic Acid and  Evaluation of their Low Temperature Property

(Sintesis dan Pencirian Terbitan Ester darpadai Asid Risinoleik dan Penilaian Sifat Suhu Rendah)

Jumat Salimon* & Nadia Salih

School of Chemical Sciences and Food Technology, Faculty of Science and Technology

Universiti Kebangsaan Malaysia, 43600 Bangi Selangor D.E., Malaysia

Emad Yousif

Department of Chemistry, College of Science, Al-Nahrain University

Baghdad, Iraq

Diserahkan: 13 Februari 2012 / Diterima: 19 Jun 2012

ABSTRACT

A series of ester compounds derived from ricinoleic acid to be used as biolubricants base stock have been synthesized. The resulting products were confirmed by FTIR and NMR analyses. The synthesis was carried out in three stages: epoxidation of ricinoleic acid; synthesis of 10,12-dihydroxy-9-acyloxystearic acid from epoxidized ricinoleic acid with various fatty acids and esterification of the acyloxystearic acid products with octanol to yield octyl-10,12-dihydroxy-9-acyloxystearate. The viscosities, flash points and pour points behavior of the products were measured. The resulting esters had an increase in molar weight and viscosity and decrease in pour points as compared to ricinoleic acid.

Keywords: Biolubricants; chemical modification; epoxidation; ricinoleic acid

ABSTRAK

Suatu siri sebatian ester terbitan asid risinoleik untuk kegunaan minyak asas biolubrikan telah disediakan. Produk terhasil dikenal pasti melalui analisis FTIR dan NMR. Sintesis telah dilakukan melalui tiga langkah: pengepoksidaan asid risinoleik; sintesis 10,12-dihidroksi-9-asiloksistearik daripada asid risinoleik terepoksida dengan pelbagai asid lemak dan pengesteran asiloksistearik dengan oktanol untuk menghasilkan oktil-10,12-dihidroksi-9-asiloksistearat. Nilai kelikatan, takat kilat dan takat tuang produk yang terhasil telah ditentukan. Hasil kajian mendapati bahawa produk ester yang terhasil menunjukkan peningkatan dalam berat molekul dan nilai kelikatan serta penurunan dalam nilai takat tuang berbanding dengan asid risinoleik.

Kata kunci: Asid risinoleik; biolubrikan; modifikasi kimia; pengepoksidaan

RUJUKAN

Adhvaryu, A., Liu, Z.S. & Erhan, S.Z. 2005. Synthesis of novel alkoxylated triacylglycerols and their lubricant base oil properties. Industrial Crops and Products 21: 113-119.

Campanella, A., Fontanini, C. & Baltanás, M.A. 2008. High yield epoxidation of fatty acid methyl esters with performic acid generated in-situ. Chemical Engineering Journal 144: 466-475.

Campanella, A., Rustoy, E., Baldessari, A. & Baltanás, M.A. 2010. Lubricants from chemically modified vegetable oils. Bioresource Technology101: 245-254.

Cermak, S.C., Skender A.L., Deppe A.B. & Isbell, T.A. 2007. Synthesis and physical properties of tallow-oleic estolide 2-ethylhexyl esters. Journal of American Chemical Society 48: 449-456.

Hwang, H.S. & Erhan, S.Z. 2001. Modification of epoxidized soybean oil for lubricant formulations with improved oxidative stability and low pour point. Journal of American Chemical Society 78: 1179-1184.

Joseph, P.V. 2007. Study of some non-edible vegetable oils of Indian origin for lubricant application. Journal of Synthetic Lubrication 24: 181-197.

Matthew T.S., Nader S., Bigyan A. & Lambert A.D. 2007. Influence of fatty acid composition on the tribological performance of two vegetable-based lubricants. Journal of Synthetic Lubrication 24: 101-110.

Metzger, J.O. 2009. Fats and oils as renewable feedstock for chemistry. European Journal of Lipid & Science Technology 111: 865-876.

Moser, B.R. & Erhan, S.Z. 2007. Preparation and evaluation of a series of α-hydroxy ethers from 9,10-epoxystearates. European Journal of Lipid & Science Technology 109: 206-213.

Moser, B.R. 2009. Comparative oxidation stability of fatty acid alkyl esters by accelerated methods. Journal of American Chemical Society 86: 699-706.

Salih, N., Salimon, J. & Yousif, E. 2011a. The physicochemical and tribological properties of oleic acid based trimester biolubricants. Industrial Crops and Products 34: 1089-1096.

Salih, N., Salimon, J. & Yousif, E. 2011b. Synthesis of oleic acid based esters as potential basestock for biolubricant production. Turkish Journal of Engineering & Environmental Science 35: 115-123.

Salimon, J., Mohd Noor, D.A., Ahmad Tajuddin, N., Mohd Yusoff, F. & Ahmad, N. 2010. Fatty acid composition and physicochemical properties of Malaysian castor bean Ricinus communis L. seed oil. Sains Malaysiana 39(5): 761-764.

Salimon, J., Salih, N. & Yousif, E. 2011a. Chemically modified biolubricant basestocks from epoxidized oleic acid: Improved low temperature properties and oxidative stability. Journal of Saudi Chemical Society 15: 195-201.

Salimon, J., Salih, N. & Yousif, E. 2011b. Synthetic biolubricant basestocks from epoxidized ricinoleic acid: improved low temperature properties. Kemija u industriji 60: 127-134.

Salimon, J., Salih, N. & Yousif, E. 2011c. Synthesis, characterization and physicochemical properties of oleic acid ether derivatives as biolubricant basestocks. Journal of Oleo Science 60: 613-618.

Salimon, J., Salih, N. & Yousif, E. 2010a. Improvement of pour point and oxidative stability of synthetic ester basestocks for biolubricant applications. Arabian Journal of Chemistry doi: 10.1016/j.arabjc.2010.09.001.

Salimon, J. & Salih, N. 2010b. Modification of epoxidized ricinoleic acid for biolubricant base oil with improved flash and pour points. Asian Journal of Chemistry 22: 5468-5476.

Salimon, J., Salih, N. & Yousif, E. 2010c. Biolubricants: raw materials, chemical modifications and environmental benefits. European Journal of Lipid & Science Technology 112: 519-530.

Sharma, B.K., Adhvaryu, A., Liu, Z. & Erhan, S.Z. 2006. Chemical modification of vegetable oils for lubricant applications. Journal of American Chemical Society 83: 129-136.

Sliverstien, R., Bassler, G. & Morrill, T. 2005. Spectrometric identification of organic compounds. 7^th ed. New York: John-Wiley.

*Pengarang untuk surat-menyurat; email: jumat@ukm.my