Sains Malaysiana 42(11)(2013): 1655–1661

Penghasilan Estolida Berasaskan Asid Risinoleik-Oleik Menggunakan

Mangkin Asid Polihetero

(Production of Ricinoleic-Oleic Based Estolide Using Polyhetero Acid Catalyst)

NOR ASIKIN MOHAMAD NORDIN¹, AINOL HAYAH AHMAD NADZRI², NADIA FARHANA², JUMAT SALIMON²* & MOHD AMBAR YARMO²

¹Program Pengajian Diploma, UTMSPACE, Universiti Teknologi Malaysia, Kuala Lumpur

Jalan Semarak, 54100 Kuala Lumpur, Malaysia

²Pusat Pengajian Sains Kimia dan Teknologi Makanan, Fakulti Sains dan Teknologi,

Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia

Diserahkan:  30 Mac 2011/Diterima:  Jun 2013

ABSTRAK

Kajian mengenai penghasilan estolida berasaskan kepada asid risinoleik dan asid oleik telah dilakukan. Asid polihetero, asid 12-fosfotungstik dan asid silikotungstik telah digunakan sebagai mangkin dan tindak balas dilakukan pada suhu 60 atau 90ºC, selama 10 atau 24 jam. Nisbah mol antara asid risinoleik dan asid oleik ialah 2:1 dan peratus berat mangkin terhadap reaktan adalah 5%. Spektrum FTIR produk estolida telah dibandingkan dengan produk tindak balas yang menggunakan mangkin homogen asid perklorik. Pembentukan estolida ditunjukkan dengan kehadiran tiga puncak baru pada 1733 cm-1 untuk kumpulan berfungsi C=O ester, 967 cm-1 untuk -CH=CH- trans dan 1177 cm-1 untuk C-O-C. Spektrum FTIR yang serupa juga telah diperoleh untuk produk menggunakan mangkin homogen asid perklorik. Analisis LC-MS menunjukkan terbentuk tiga puncak baru monoestolida pada masa penahanan (Rt) 8.6 (m/z 577), 10.2 (m/z 559) dan 12.1 minit (m/z 561). Hasil kajian menunjukkan tindak balas kondensasi antara oleik-risinoleik dengan menggunakan asid perklorik, pepejal asid silikotungstik dan asid fosfotungstik sebagai mangkin berjaya menghasilkan estolida masing-masing dengan peratus hasil 70.2, 70.0 dan 60.8%.

Kata kunci: Asid oleik; asid risinoleik; estolida; tindak balas kondensasi

ABSTRACT

A study on the production of oleic and ricinoleic acids based estolide was carried out. Polyhetero acid of 12-phosphotungsti and silicotungstic acids have been used in the reactions at 60ºC or 90ºC, for 10 or 24 h. The mole ratio of ricinoleic to oleic acids was 2:1 and weight percentage of catalyst to the reactant used was 5%. The FTIR spectrum of the estolide product was compared to reaction product using perchloric acid as homogeneous catalyst. The estolide formation was shown by the existence of three new peaks at 1733 cm-1 for C=O ester, 967 cm-1 for -CH=CH- trans and 1177 cm-1 for C-O-C, respectively. The same FTIR spectrum pattern was observed for the reaction product using perchloric acid as homogeneous catalyst. The LC-MS analysis showed that the formation of three new monoestolide peaks at retention time (Rt) at 8.6 (m/z 577), 10.2 (m/z 559) and 12.1 min (m/z 561). The results showed that the condensation reaction between oleic-ricinoleic acids by using perchloric acid, solid acid silicotungstics and phosphotungstics acid as catalysts was successfully formed the estolides with yields percentages of 70.2, 70.0 and 60.8%, respectively.

Keywords: Condensation reaction; estolide; oleic acid; ricinoleic acid

RUJUKAN

Cermak, S.C. & Isbell, T.A. 2001. Synthesis of estolides from oleic and saturated fatty acids. Journal of the American Oil Chemists’ Society 78(6): 557-565.

Cermak, S.C. & Isbell, T.A. 2002. Physical properties of saturated estolides and their 2-Ethylhexyl esters. Industrial Crops and Products 16(2): 119-127.

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 the American Oil Chemists’ Society 84(5): 449-456.

Delafield, F.P., Doudoroff, N.J., Palleroni, N.J., Lusty, C.J. & Fotopoulus, R. 1965. Decomposition of Polyhydroxybutyrate by pseudomonads.  Journal Bacteriol 90: 1455-1466.

Erhan, S.M., Kleiman, R. & Isbell, T.A. 1993. Estolides from meadowfoam oil fatty acids and other monounsaturated fatty acids. Journal of the American Oil Chemists’ Society 70(5): 461-465.

Erhan, S.M., Kleiman, R. & Isbell, T.A. 1995. Methods for increasing estolide yields in a batch reactor. Journal of the American Oil Chemists’ Society 72(6): 671-674.

Erhan, S.M., Kleiman, R. & Abbott, T.P. 1996. Quantitation of estolides by fourier transform infrared spectroscopy. Journal of the American Oil Chemists' Society 73(5): 563-567.

Harry-O’kuru, R.E., Isbell, T.A. & Weisleder, D. 2001. Synthesis of estolide esters from Cis-9-octadecenoic acid estolides. Journal of the American Oil Chemists’ Society 78(3): 219- 222.

Isbell, T.A. & Kleiman, R. 1994. Characterization of estolides produced from the acid-catalyzed condensation of oleic acid. Journal of the American Oil Chemists’ Society 71(4): 379-383.

Isbell, T.A. & Kleiman, R. 1996. Mineral acid-catalyzed condensation of meadowfoam fatty acids into estolides. Journal of the American Oil Chemists’ Society 73(9): 1097- 1107.

Modak, S.N.K., J.G. 1965. Kinetics of estolide formation and decomposition. Journal American Chemical Society 42: 428-432.

Raynor, M.W., Bartle, K.D., Clifford, A.A., Chalmers, J.M., Katase, T., Rouse, C.A., Markides, K.E. & Lee, M.L. 1990. Analysis of aliphatic and phenolic carboxylic acids by capillary supercritical fluid chromatography-fourier-transform infrared microspectrometry. Journal of Chromatography A 505(1): 179-190.

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