This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis and Evaluation of Jatropha Oil Branched Esters as Potential Fire Resistant Hydraulic Fluids
Corresponding Author(s) : Madhu Deverapaga
Asian Journal of Chemistry,
Vol. 35 No. 8 (2023): Vol 35 Issue 8, 2023
Abstract
Jatropha oil (Jatropha curcas L.), a non-edible oil with oleic acid (45.7%) and linoleic acid (33%) as major components, was used to prepare basestocks for biolubricants. The hydrolyzed fatty acids underwent reaction with two iso-alcohols, 2-ethyl-1-hexanol (EH) and 3,5,5-trimethyl-1-hexanol (TMH) and 5 different polyols, namely neopentyl glycol (NPG), 2-methyl-2-propyl-1,3-propandiol (MPPD), trimethylolpropane (TMP), trimethylolethane (TME) and pentaerythritol (PE) at around 140 ºC in presence of catalyst p-toluenesulfonic acid (p-TSA) and xylene as solvent. The yields for the branched mono- and polyol esters ranged from 90% to 97.5%. The physico-chemical, lubricant and tribological properties of these esters as well as their 1H NMR, 13C NMR, IR and ESI-MS techniques were investigated. Among the products, polyol esters were found to possess good viscosity indices, good foam stability, higher thermal stability and higher flash and auto ignition points compared to branched mono esters. TMP and TME esters have matched the specifications of ISO VG 46 and PE esters match ISO VG 68 fire resistant hydraulic fluids, which are in high demand.
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P. Nagendramma and S. Kaul, Renew. Sustain. Energy Rev., 16, 764 (2012); https://doi.org/10.1016/j.rser.2011.09.002
I.M. Cavalcante, N.R.D.C. Rocha, D.H.A. de-Brito, A.P.D. Schuller, J.F. Câmara Neto, S.M. de Morais, F.M.T. de Luna, M.T.G.F. Schanz, M.E. Maier and N.M.P.S. Ricardo, J. Am. Oil Chem. Soc., 96, 75 (2019); https://doi.org/10.1002/aocs.12160
K. Kamalakar, G.N.V.T.S. Manoj, R.B.N. Prasad and M.S.L. Karuna, 15, 456 (2000); https://doi.org/10.1016/j.indcrop.2015.07.050
I. Stanciu, Orient. J. Chem., 37, 752 (2021); https://doi.org/10.13005/ojc/370333
P. Nowak, K. Kucharska and M. Kamiñski, Int. J. Environ. Res. Public Health, 16, 3002 (2019); https://doi.org/10.3390/ijerph16163002
K. Ghasemzadeh, S.M. Sadati Tilebon, M. Nasirinezhad and A. Basile, 613, 613 (2018); https://doi.org/10.1016/B978-0-444-63903-5.00023-6
B.R. Hohn, K. Michaelis and R. Dobereiner, J. Lubr. Eng., 55, 37 (1999).
S. Lawate and K. Lal, High Oleic Polyol Esters, Compositions and Lubricants, Functional Fluids and Greases Containing the Same, US Patent 5773391 (1998).
U. Schuchardt, R. Sercheli and R.M. Vargas, J. Braz. Chem. Soc., 9, 199 (1998); https://doi.org/10.1590/S0103-50531998000300002
Y.-Y. Linko, T. Tervakangas, M. Lämsä and P. Linko, Biotechnol. Tech., 11, 889 (1997); https://doi.org/10.1023/A:1018410316231
E. Uosukainen, Y.Y. Linko, M. Lämsa, T. Tervakangas and P. Linko, J. Am. Oil Chem. Soc., 75, 1557 (1998); https://doi.org/10.1007/s11746-998-0094-8
S. Gryglewicz, W. Piechocki and G. Gryglewicz, Bioresour. Technol., 87, 35 (2003); https://doi.org/10.1016/S0960-8524(02)00203-1
F. Toldrá-Reig, L. Mora and F. Toldrá, Appl. Sci., 10, 3644 (2020); https://doi.org/10.3390/app10103644
U. Krishnakumar and V. Sivasubramanian, J. Oil Palm Res., 15, 42 (2003); https://doi.org/10.4236/jsbs.2016.63006
R. Yunus, A. Fakhru’l-Razi, T.L. Ooi, S.E. Iyuke and J.M. Perez, Eur. J. Lipid Sci. Technol., 106, 52 (2004); https://doi.org/10.1002/ejlt.200300862
N.H. Arbain and J. Salimon, E-J. Chem., 8, S33 (2011); https://doi.org/10.1155/2011/789374
T.S. Chang, H. Masood, R. Yunus, U. Rashid, U.T.S.Y. Choong and D.R.A. Biak, Ind. Eng. Chem. Res., 51, 5438 (2012); https://doi.org/10.1021/ie2028365
K.V. Padmaja, B.V.S.K. Rao, R.K. Reddy, P.S. Bhaskar, A.K. Singh and R.B.N. Prasad, Ind. Crops Prod., 35, 237 (2012); https://doi.org/10.1016/j.indcrop.2011.07.005
K.V. Padmaja, M.S.L. Karuna, K. Saravanan and R.B.N. Prasad, Indian Patent, 2635DEL2011 (2011).
K. Kamalakar, A.K. Rajak, R.B.N. Prasad and M.S.L. Karuna, Ind. Crops Prod., 51, 249 (2013); https://doi.org/10.1016/j.indcrop.2013.08.058
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L.I. Farfan-Cabrera, M. Franco-Morgado, A. González-Sanchez, J. Perez-Gonzalez and B.M. Marin-Santibanez, Molecules, 27, 1205 (2022); https://doi.org/10.3390/molecules27041205
K. Mizera and J. Ryszkowska, J. Elastomers Plast., 51, 157 (2019); https://doi.org/10.1177/0095244318772323
M. Khan, K. Madden and M.T. Burrus, Sports Health, 10, 169 (2018); https://doi.org/10.1177/1941738117738988
I.M. Cavalcante, N.R.C. Rocha, M.E. Maier, A.P.D. de Lima, D.M. Andrade Neto, D.H.A. de Brito, C.L. Petzhold, M.T.G.F. Schanz and N.M.P.S. Ricardo, Ind. Crops Prod., 62, 453 (2014); https://doi.org/10.1016/j.indcrop.2014.08.022
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