Malaysian Journal of Analytical Sciences Vol 19 No 1 (2015): 118 – 128
SYNTHESIS
AND PHYSICOCHEMICAL STUDIES OF SUBERATES AS BIOLUBRICANT BASETOCK
(Sintesis dan Kajian Fiziko-Kimia bagi Suberat
sebagai Minyak Asas Biopelincir)
Maratun Najiha Abu Tahari, Salma
Samidin, Mohd Ambar Yarmo, Nadia Salih, Jumat Salimon*
School of
Chemical Sciences &Food Technology,
Faculty of
Science and Technology,
Universiti
Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia
*Corresponding author: jumat@ukm.edu.my
Abstract
Synthesis of biolubricant through chemically modified suberic
acid (SA) with 3 different types of alcohols which are 1-octanol (Oc),
1-decanol (De) and 1-dodecanol (Do) was conducted with presence of 4%
p-toluenesulfonic acid (PTSA) as a catalyst. Preparation, characterization and
physico-chemical properties of three types diester (suberate) is discussed in
this paper. The diester products were confirmed by NMR and FTIR spectroscopic
analysis. Addition of alcohols at the side chains of diacid increases the
molecular weight and chain length resulted in the increment of viscosity index
(VI), oxidative stability (OT) and flash point (FP) of the diesters. The result
showed that 1,8-dioctanyl suberate (DOS) exhibited the most favorable low
temperature performance (PP -8.5°C) while 1,8-didodecanyl suberate (DDoS)
exhibited higher OT (190°C) and higher FP (224°C) than the other diester oils.
On the other hand, the highest VI around 197°C was obtained for 1,8-didecanyl
suberate (DDS). These diester oils have a good potential in formulation of
industrial biolubricants.
Keywords: biolubricant,
diester suberic acid, chemically modified
Abstrak
Sintesis biopelincir melalui modifikasi kimia
terhadap asid suberik (SA) dengan 3 jenis alkohol iaitu 1-oktanol (Oc),
1-dekanol (De) dan 1-dodekanol (Do) dilakukan dengan kehadiran 4% asid
p-toluenasulfonik (PTSA) sebagai katalis. Penyediaan, pencirian dan sifat
fisiko-kimia bagi tiga jenis diester (suberat) dibincangkan dalam manuskrip
ini. Produk diester yang terhasil ditentusahkan melalui analisis spektroskopi
NMR dan FTIR. Penambahan alkohol pada rantai sisi diasid meningkatkan berat
molekul dan panjang rantai mengakibatkan peningkatan indeks kelikatan,
kestabilan oksidatif dan takat kilat diester. Hasil kajian menunjukkan bahawa 1,8-dioktanil suberat
(DOS) mempamerkan prestasi bekerja pada suhu rendah yang baik (PP -8.5°C) dan
1,8-didodekanil suberat (DDoS) memperlihatkan OT yang lebih tinggi (190°C) dan
FP yang lebih tinggi (224°C) berbanding minyak diester yang lain. Selain itu,
1,8-didekanil suberat (DDS) memiliki VI yang tertinggi iaitu 197°C. Semua minyak diester ini memiliki potensi yang baik dalam formulasi
biopelincir industri.
Kata kunci:
biopelincir, diester suberik asid, modifikasi kimia
References
1.
Sharma,
B.K., Adhvaryu, A., Liu, Z. and Erhan, S.Z. (2006). Chemical modification of
vegetable oils for lubricant applications. Journal
of American Oil Chemical Society 83(2): 129-136.
2.
Rhee,
I.S. (1996). Evaluation of
environmentally acceptable hydraulic fluids. NLGI Spokesman 60: 5.
3.
Rudnick,
L.R. (2003). Lubricant Additives,
Chemistry and Applications. New York: CRC Press Taylor & Francis Group.
4.
Hwang,
H.S. and Erhan, S.Z. (2006). Synthetic lubricant basestock from epoxidized
soybean oil and Guerbet alcohols. Industrial
Crops and Products 23: 1257-1260.
5.
Adhvaryu,
A. and Erhan. S.Z. (2002). Epoxidiezed soybean oil as a potential source of
high temperature lubricants. An
International Journal of Industrial of Crops and Products 15: 247-254
6. Basiron, Y., Loh, S.K. and Choo, Y.M. (2000). Additive for
petroleum fuels and lubricant, biofuels and biolubricant. Oil Palm Bulletin 40:
1-5
7. Salunkhe, D.K., Chavan, J.K., Adsulke, R.N. and Kadam, S.S. (1992). Worl Oil Seeds: Chemistry Technology and Utilization. Van Nostrand Reinhold, New York, 1-8.
8. Bokish, M. (1998). Fats and Oils Handbook. AOCS Prss,
Champaign, IL. pp 838.
9.
Battersby,
N.S. (2000). The biodegradability and microbial toxicity testing of
lubricants-Some recommendations. Chemosphere 41(7): 1011-1027.
10. Havet, L., Blouet, J., Valloire, F., Brasseur, E., Slomka, D. (2001). Tribology characteristics of some environmentally friendly lubricant. Wear 248: 140-146.
11.
Walsh,
W. (2002). Determination of Triglyceride
Composition of Vegetable Oils Using HPLC aand Light Scattering Detection.
Annual Meeting and Food Expo, Session 30G, Anaheim, CA.
12.
Krzan,
B. and Vizintin, J. (2003). Tribological properties of environmentally adopted
universal tractor transmission oil based on vegetable oil. Tribology Industry 36: 827-833.
13.
Jumat,
S., Nadia, S. and Emad, Y. (2012). Improvement of pour point and oxidative
stability of synthetic ester basestocks for biolubricant applications. Arabian Journal of Chemistry 5:
193-200.
14.
Gryglewicz,
S., Oko, F.A., Stankiewicz, M. and Surawska, I. (2006). Esters of dicarboxylic
acids as additives for lubricating oils. Tribology
International 39: 560–564.
15.
Gunstone,
F.D. (2004). The Chemistry of Oils and
Fats: Sources, Compositions, Properties and Uses. U.K: Blackwell Publishing
Ltd.
16.
Pavia,
D.L., Lampman, G.M., Kriz, G.S. and Vyvyan, J.R. (2010). Introduction of Spectroscopy. (fourth Ed.). Canada: Nelson
Education, Ltd.
17.
Robiah,
Y., Razi, A.F., Ooi, T.L., Iyukie, S.E. and Idris, A. (2003). Development of
optimum synthesis method for transesterification of palm oil methyl ester and
trimethylpropane to environmentally acceptable palm oil-based lubricant. Journal of Palm Research 15(2): 35-41
18.
ASTM
Standard D5949, Standard test method for pour point of petroleum (automatic
pressure pulsing method), ASTM, West Conshohocken, PA, USA.
19.
Jumat,
S., Nadia, S. and Emad, Y. (2012). Synthetic biolubricant basestocks based on
environmentally friendly raw materials. Journal
of King Saud University – Science 24(3): 221-226.
20.
ASTM
Standard D 56-79, Standard test method for flash point of liquids with a
viscosity less than, 45 Saybolt Universal Seconds (SUS) at 37.8 °C (that don’t
contain suspended solids and don’t tend to form a surface film under test),
ASTM, West Conshohocken, PA, USA.
21.
ASTM
Standard D 2270-93, Standard test method for calculating viscosity index from
kinematic viscosity at 40 and 100 °C, ASTM, West Conshohocken, PA, USA.
22.
Jumat,
S. and Nadia, S. and Emad, Y. (2012). Biolubricant basestocks from chemically
modified ricinoleic acid. Journal of King
Saud University – Science 24(1): 11-17.
23.
Williamson,
K.L. (1994). Synthesis of Isobutyl
Propionate via Esterification:
Macroscale and Microscale Organic
Experiments. (second Ed.). Houghton Mifflin, Boston.
24.
George,
S.A., Swift, E.J., Thompson, J.Y. and Heymann, H.O. (2003). Irradiance effects
on the mechanical properties of universal hybrid and flowable resin composites.
Dental Materials 19(15): 406-413.
25.
Jumat,
S., Nadia, S. and Emad, Y. (2010c). Biolubricants: Raw materials, chemical
modifications and environmental benefits. European
Journal Lipid Science Technology 112: 519-530.
26.
Erhan,
S. Z., Sharma, B. K., Adhvaryu, A. and Liu, Z. (2006). Chemical modification of
vegetable oils for lubricant applications. Journal
of American Oil Chemist Society 83: 129-136.