The
Malaysian Journal of Analytical Sciences Vol 17 No 1 (2013): 185 – 192
SYNTHESIS OF ESTOLIDE
2-ETHYLHEXYL ESTER FROM
RICINUS
COMMUNIS
(Sintesis
Estolida 2-Etilheksil Ester dari Ricinus
Communis)
Nazrizawati Ahmad Tajuddin1,2*,
Nor Habibah Rosli1, Jumat Salimon2, Mohd Firdaus Mohd
Yusoff 2,
Noraishah Abdullah2
1Department of Chemistry, International Education
College,
UiTM Section 17,
40200 Shah Alam, Selangor, Malaysia
2Oleochemistry Programme, School of Chemical Science
and Food Technology,
Faculty of
Science and Technology,
Universiti
Kebangsaan Malaysia,43000 Bangi, Selangor, Malaysia
*Corresponding author: nazriza@salam.uitm.edu.my
Abstract
Estolide
2-ethylhexyl ester synthesized through condensation reaction between ricinoleic
acid from castor oil (Ricinus communis)
and lauric acid, and then capped with 2-ethylhexyl alcohol. The reaction was
continuously conducted under vacuum for 24 hours. Product of 2-ethylhexyl ester
was characterized by using Fourier Transform Infrared (FTIR) to determine
functional group and Nuclear Magnetic Resonans (NMR) for structure’s
determination. The presence of ester group at 1738.23 cm-1
wavenumber indicates that the formation of estolide ester has occurred. The
vibration peak of C-O at 1174.60 cm-1 and 1117.10 cm-1
support the formation of ester. The presence of CH2 bending
indicated the long-chain compound. The ester methine signal at 3.8669 ppm
indicated the estolide linkage in the 1H-NMR spectrum while the 13C-NMR
showed two carbonyl signals at 173.41 ppm for acid and 173.56 ppm for ester.
Keywords: Castor oil,
ricinoleic acid, estolide ester, biodegradable, biolubricant study
References
1. Lin,
J.T. & Chen, G.Q. 2010. Acylglycerols Containing Trihydroxy Fatty Acids in
Castor Oil and the Regiospecific Quantification of Triacylglycerols. Journal
of the American Oil Chemists' Society.
87:1371-1379
2. Jumat, S., Neeranjini, N., Nadia, S. & Bashar,
M.A. 2011. Synthesis
and Physical Properties of Estolide Ester Using Saturated Fatty Acid and Ricinoleic Acid. Journal of Automated Methods and Management in Chemistry.2011: 1-4
3. Cermak,
S.C. & Isbell, T.A. 2002. Physical prop of saturated estolides and their
2-ethylhexyl ester. Industrial Crops
Products. 16: 119-127.
4. Zaher,
F.A. & Nomany, H.M. 1988. Vegetable oils and lubricants. Grases Aceities (Seville). 39: 235-238
5. Becker,
R. & Knorr, A. 1996. An evaluation of antioxidants for vegetable oil at
elevated temperatures. Lubri. Sci. 8:
95-117.
6. Asadauskas, S. & Erthan, S.Z. 1999. Depression
of pour points of vegetable oils by blending with diluents used for
biodegradable lubricants. J.Am.Oil
Chem.Soc. 76: 313-316.
7. Isbell,
T.A., Kleiman, R. & Plattner, B.A. 1994. Acid.Catalyzed Condensation of Oleic Acid into Estolides and
Polyestolides. J.Am.Oil Chem.Soc:
71.
8. Isbell,
T.A. & Kleiman, R. 1994. Characterization of Estolides Produced from the
Acid-Catalyzed Condensation of Oleic Acid. New Crops Research. 71:379-383.
9. Cermak,
S.C. & Isbell, T.A. 2001. Synthesis of estolides from oleic and saturated
fatty acids. J.Am.Oil.Chem.Soc. 78:
557-565.
10. Cermak,
S.C. & Isbell, T.A. 2003. Synthesis physical properties of estolide-based
functional fluids. Industrial Crops
Products. 18:183-196.
11. Cermak, S.C.,
Brandon, K.B. & Isbell, T.A. 2006. Synthesis and physical properties of
estolides from lesquerella and castor fatty acid esters. Industrial Crops Products.23:54-64.
12. Pavia, D.L.,
Lampman, G.M. & Kriz, G.S. 2001. Introduction to spectroscopy, 3rd
ed. America:Thomson Learning.