The Malaysian Journal of Analytical Sciences Vol 17
No 1 (2013): 119 – 128
THE EFFECT OF CHEMICAL
STRUCTURE ON POUR POINT, OXIDATIVE STABILITY AND TRIBOLOGICAL PROPERTIES OF
OLEIC ACID TRIESTER DERIVATIVES
(Kesan Struktur Kimia Pada Titik Pour, Kestabilan
Pengoksidaan Dan Sifat Tribological Derivatif Triester Asid Oleik)
Nadia Salih1, Jumat Salimon1*,
Emad Yousif2
1School of
Chemical Sciences and Food Technology, Faculty of Science and Technology,
Universiti Kebangsaan Malaysia, 43600
Bangi, Selangor, Malaysia
2Department of
Chemistry, College of Science,
Al-Nahrain University, Baghdad, Iraq
*Corresponding author: jumat@ukm.my
Abstract
Due to the
strict regulations imposed on non-biodegradable mineral oil-based lubricants,
the development and applications of biolubricants are increasing daily. Plant
oils are being investigated as a potential source of environmentally favorable
lubricants because of their biodegradability, renewability,
viscosity-temperature relationship, low volatility and excellent lubrication
performance. However, the use of plant oils has some restriction, the most
critical being oxidative stability and low-temperature problems. This paper
presents systematic modifications to improve the physicochemical and
tribological properties of plant oil derivatives. The results showed that among
the oleic acid-based triester compounds, 2-ethylhexyl
9-(myristoxy)-10-(heptanoyloxy)octadecanoate (9) had the lowest pour
point (-47.19 ˚C) while 2-ethylhexyl
9-(caprooxy)-10-(heptanoyloxy)octadecanoate (5) had the highest onset
temperature (103.10 ˚C). Overall, the data indicate that the biolubricant
basestocks based on this chemical modification offer great potential for the
development of industrial products application.
Keywords:
Plant
oils, pour point, physicochemical properties, biolubricant basestocks
References
1.
Rhee,
I.. 1996. Evolution of environmentally acceptable hydraulic fluids. NLGI
Spokesman 60 (5), 28.
2.
Randles,
S.J., Wright, M., 1992. Environmentally considerable ester lubrication for the
automotive and engineering industeries. J.
Synth. Lubr. 9: 145-161.
3.
Castro,
W., Perez, J.M., Erhan, S.Z., Caputo, F., 2006. A study of the oxidation and
wear properties of vegetable oils: Soybean oil without additives. J. Am. Oil Chem. Soc. 83: 47-52.
4.
Doll,
K.M., Sharma, B.K., Erhan, S.Z., 2007. Synthesis of branched methyl hydroxy
strearates including an ester from bio-based levulinic acid. Ind. Eng. Chem. Res. 46: 3513-3519.
5.
Rudnick,
L., 2002. Biobased industrial fluids and lubrication. AOCS Press, Champaign, IL.
6.
Fuks,
G.I., 1963. Research in surface forces, New York, Consultants Bureau, pp.
29-88.
7.
Asadauskas, S.,
Perez, J.M., Duda, J.L., 1996. Oxidative stability and antiwear properties of high
oleic vegetable oils. Lub. Eng. 52:
877-882.
8.
Schuster,
H., Rios, L.A., Weckes, P.P., Hoelderich, W.F., 2008. Heterogenouse catalyst for the production of new lubricants
with unique proprties. Appl. Catalysis A:
Gen. 348: 266-270.
9.
Salih,
N., Salimon, J., Yousif, E., 2011 a. The physicochemical and tribological
properties of oleic acid based triester biolubricants. Ind. Crops Prod. 33: 1089-1096.
10.
Salih,
N., Salimon, J., Yousif, E., 2011 b. Synthesis of oleic acid based esters as
potential basestock for biolubricant production. Turk. J. Eng. Env. Sci. 35: 115-123.
11.
American
Society for Testing Materials, 2011 a. Standard test method for pour point of
petroleum products (automatic pressure pulsing method). ASTM, West Conshohcken,
PA (USA).
12.
American
Society for Testing Materials, 2011 b. Standard test method for cloud point of
petroleum products (constant cooling rate method). ASTM, West Conshohcken, PA
(USA).
13.
American
Society for Testing Materials, 2011 c. Standard test method for flash point by
Tag Closed Cup Tester. ASTM, West Conshohcken, PA (USA).
14.
American
Society for Testing Materials, 2011 d. Standard Test Method for kinematic
viscosity of transparent and opaque liquids. ASTM, West Conshohcken, PA (USA).
15.
American
Society for Testing Materials, 2011 e. Standard practice for calculating
viscosity index from kinematic viscosity at 40 and 100 ˚C. ASTM, West
Conshohcken, PA (USA).
16.
American
Society for Testing Materials, 2011 f. Standard test method for density,
relative density (specific gravity), or API gravity of crude petroleum and
liquid petroleum products by hydrometer method. ASTM, West Conshohcken, PA
(USA).
17.
American
Society for Testing Materials, 2011 g. Standard test method for measure the
volatility of petroleum products. ASTM, West Conshohocken, PA (USA).
18.
American
Society for Testing Materials, 2011 h. Standard test method for wear preventive
characteristics of lubricating fluid (four-ball method). ASTM, West
Conshohocken, PA (USA).
19.
Salimon,
J., Salih, N., Yousif, E., 2011 a. Synthetic biolubricant basestocks from
epoxidized ricinoleic acid: improved low temperature properties. Kem. Ind. 60 127-134.
20.
Salimon,
J., Salih, N., Yousif, E., 2011 b. Chemically modified biolubricant basestocks
from epoxidized oleic acid: Improved low temperature properties and oxidative
stability. J. Saudi Chem. Soc. 15, 195-201.
21.
Sliverstien, R.,
Bassler, G., Morrill, T., 2005. Spectrometric identification of organic
compounds. 7th ed.,
John-Wiley, New York.
22.
Salimon,
J., Salih, N., 2010. Modification of epoxidized ricinoleic acid for
biolubricant base oil with improved flash and pour points. Asian J. Chem. 22: 5468-5476.
23.
Hwang, H.-S.,
Erhan, S.Z., 2001. Modification
of epoxidized soybean oil for lubricant formulations with improved oxidative
stability and low pour point. J. Am. Oil
Chem. Soc. 78: 1179-1184.
24.
Zhang,
Y.Y., Ren, T.H., Wang, H.D., Yi, M.R., 2004. A comparative study of phenol-type
antioxidant in methyl oleate with quantum calculations and experiments. Lub. Sci. 16: 385-392.
25.
Randals,
S.J., 1999. Esters. In: Rudnick, L.R., Shubkin, R.L. (Eds.), Synthetic
lubricants and high performance functional fluids. Marcel Dekker, New York, pp.
63-102.
26.
Sharma,
B.K., Adhvaryu, A., Liu, Z., Erhan, S.Z., 2009. Friction and wear behavior of
thioether hydroxyl vegetable oil. Tribology
Int. 42 353-358.