Malaysian Journal of Analytical Sciences Vol 19 No 1 (2015): 97 – 105
Oleic Acid based Polyesters of Trimethylolpropane
and Pentaerythritol for Biolubricant Application
(Poliester Berasaskan Trimetilolpropana dan
Pentaeritritol dengan Asid Oleik untuk Kegunaan Biopelincir)
Hamizah Ammarah Mahmud, Nadia
Salih, Jumat Salimon*
School of
Science and Food Technology,
Faculty of
Science and Technology,
Universiti
Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia
*Corresponding author: jumat@ukm.edu.my
Abstract
The production
of polyesters based on oleic acid and trimethylolpropane (TMP) or
pentaerythritol (PE) as potential biolubricant were carried out. The
esterification processes between oleic acid with TMP or PE were carried out using
sulfuric acid as a catalyst. The
esterification process produced high yield between 92%-94% w/w respectively.
The formation of polyesters was confirmed using gas chromatography (GC-FID),
Fourier Transform Infrared Spectroscopy (FTIR) and Nuclear Magnetic Resonance
(NMR). The polyesters were analyzed for basic lubrication physicochemical
properties. The results showed that
polyesters of both TMP and PE having high viscosity index between 200-309, good
pour points ranging from -42°C to -59°C and high flash points of 280°C - 300 °C
respectively. The polyesters also showed good thermal oxidative stability with
TGA onset temperatures above 180 °C. In general both products are plausible to
be used as biolubricant for industrial application.
Keywords: esterification, oleic acid,
pentaerythritol, polyhydric alcohol, trimethylolpropane
Abstrak
Penghasilan
poliester berasaskan asid oleik dan trimetilolpropana (TMP) atau pentaeritritol (PE) sebagai
biopelincir yang berpotensi telah dijalankan. Proses pengesteran asid oleik
diantara TMP atau PE menggunakan mangkin asid sulfurik. Sebanyak 92-94 % w/w hasil daripada
pengesteran berjaya dihasilakan. Pengesahan dan pengecaman poliester adalah
menggunakan Gas Kromatografi(GC-FID), Spektroskopi Inframerah Fourier Transform
(FTIR) dan Resonan Magnetik Nuklear (1H NMR dan 13C NMR
). Ujian asas fisiko-kimia sifat pelinciran telah dijalankan keatas poliester.
Hasil analisis menunjukkan kedua-dua poliester TMP dan PE mempunyai indeks
kelikatan yang tinggi 200-309, takat tuang yang baik dari julat suhu dari
-42°C kepada -59°C; takat kilat yang
tinggi 280°C - >300 °C. Kesemua poliol ester menunjukkan kestabilan
oksidatif termal yang bagus dimana suhu
onset TGA melebihi 180 °C. Secara umumnya kedua hasil adalah munasabah untuk
digunakan sebagai biopelincir dalam aplikasi perindustrian.
Kata kunci: pengesteran, asid oleik,
pentaeritritol, polihidrik alkohol, trimetilolpropana
References
1. Arnsek, A.,
Vizintin, L., (2000). Lubricating
properties of rapeseed based oils. Journal Synthetic Lubricant 16,
281–295.
2.
Jumat,
S., Nadia, S., Emad, Y., (2012). Industrial development and applications of
plant oils and their biobased Oleochemicals. Arabians Journal of Chemistry. 5: 135-145
3.
Erhan,
S. Z., Sharman, K. B and Perez, J. M. (2006). Oxidation and low temperature
stability of vegetable oil-based lubricant. Industrial Crops and Product
24: 292-299.
4.
Lathi,
P. S and Mattiasson, B. (2007). Green approach for the preparation of
biodegradable lubricant base stock from epoxidized vegetable oil. Applied
Catalysis 69:207-212.
5.
Campanella,
A., Rustoy, E., Baldessari, A and Baltanás, M. A. (2010). Lubricants from
chemically modified vegetable oils. Bioresource
Technology 01: 245-254.
6.
Korlipara,
V.P., Bhamidipati, V.S.K.R., Rondla,K.R.,Potula, S.B., Arun, K.S.and Rachapudi,
B.N.P. (2011). 10-Undecenoic acid-based polyol esters as potential lubricant
base stocks. Industrial Crops and
Products 35: 237-240
7.
Wilson,
B., (1998). Lubricants and functional fluids from renewable sources. Ind.
Lubr. Tribol. 50, 6-15
8.
Gryglewicz,
S., Piechocki, W and Gryglewicz, G. (2003). Preparation of polyol esters based
on vegetable and animal fats. Bioresource Technology 87: 35-39.
9.
Anita
Abu Bakar, Yunus, R., Luqman Chuah and Fakhru’l-Razi, A. (2007).Study on effect
of hydroxyl groups on lubrication properties of palm based trimethylolpropane
esters: development of synthesis method. Journal of Applied Science 7(5): 2011-2014
10.
Bongardt,
F.B, Bossmann, A., Westfetchetel, W.G. and Giede,W., (1996). Manufacture of
synthetic esters from alcohol and high oleic low strearic fatty acid. Ger.
Offen., DE 4,444, 137.
11.
Erhan,
S.Z., and Perez, J.M. (2002). Biobased industrial Fluids and Lubricants. AOCS
Pres, Champaign, IL.
12.
Lathi,
P.S.and Mattiason, B., (2006) Green approach for the preparation of
biodegradable lubricant base stock from epoxidized vegetable Oil. Applied Catalyst Lipid. 77: 155-171.
13.
Hwang,
H.S. and Erhan, S.Z., (2001).
Modification of epoxidized soybean oil for lubricant formulations with improved
oxidative stability and low pour point. Journal
America Chemist Oils Society 78: 1179-1184
14.
Hwang,
H.S., Adhvaryu, A. and Erhan, S.Z., (2003). Preparations and Properties of
lubricants base stock from epoxidized soybean oil and 2-ethylhexanol. Journal America Chemist Oils Society. 80:
811-815
15.
Adhvaryu,
A., Liu, Z.S. and Erhan, S.Z., (2005). Synthesis of novel alkoxylated
triacylglycerols and their lubricant
base oil properties. Ind. Prod.
21:113-119
16.
Sharma,B.K.,
Liu, Z., Adhvaryu, A. and Erhan, S.Z.,
(2008). One pot synthesis of chemically modified vegetable oils. Journal Agriculture Food Chemistry. 56:
3049-3056
17.
Asadauskas,S.,Perez,J.M.
and Duda, J.L. (1996). Oxidative Stability and antiwear properties of high
Oleic Acid vegetable oils. Lubr. Eng.
52: 877-882.
18.
Erhan,
S. Z and Asadauskas, S. (2000). Lubricant basestocks from vegetable oils. Industrial
Crops and Products 11: 277-282.
19.
Yunus,
R., Fakhru’l-Razi, A., Ooi, T. L., Iyuke, S. E and Idris, A. (2003).Development
of optimum synthesis methods for transesterification of palm oil methyl esters
and trimethylolpropane to environmentally acceptable palm oil-based lubricant. Journal
of Oil Palm Research 15 (2): 35-41.
20.
Yunus,
R., Fakhru’l-Razi, A., Ooi, T. L., Iyuke, S. E and Idris, A. (2003).Preparation
and characterization of trimethylolpropane esters from palm kernel oil methyl
esters. Journal of Oil Palm Research 15(2): 42-49.
21.
Yunus,
R., Fakhru’l-Razi, A., Ooi, T. L., Iyuke, S. E and Idris, A. (2004).
Lubrication properties of trimethylolpropane esters based on palm oil and palm kernel oils. European Journal Lipid Science Technology.
106: 52-60
22.
Pavia,
D.L., Lampman, G.M. and Kriz, G.S. 2009. Introduction to Spectroscopy. 4th ed.,
United States: Thomson Learning, Inc.
23.
Robiah,
Y., Ooi, T.L., Fakhru’l-Razi, A. and Shahnor, B. (2002.) A Simple Capillary
Column GC Method for Analysis. Journal
of the American Oil Chemist’s Society 79: 1075-1080.
24.
Cermak,
S.C. and Isbell, T.A. (2003). Synthesis and
physical properties of estolide-based functional fluids. Industrial
Crops and Products 18:183-196.