Preparation of Epoxidized Fatty Acid Ethyl Ester from Tung Oil as a Bio-lubricant Base-Stock
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Preparation of epoxidized tung oil ethyl ester (ETOEE) was explored in this work via a two-step approach to produce bio-lubricant with enhanced thermal-oxidative stability. Transesterification of tung oil with ethanol was first carried out with KOH as the catalyst at 60 °C and a molar ratio of tung oil to ethanol of 1:20 for 2 h. The obtained tung oil ethyl ester (TOEE) was subjected to epoxidation in the presence of hydrogen peroxide and formic acid (FA). The highest conversion (93.6%, based on reduction of iodine value) was achieved by reacting 10 g of TOEE with 14.5 g of hydrogen peroxide and 5.86 g of FA at 50 °C for 3 h. Under these conditions, the resulting ETOEE has an oxirane number or epoxy value of 5.1%, and the presence of epoxy groups was confirmed by Fourier transform infrared spectroscopic analysis. The resulting ETOEE was further analyzed of its thermal stability under both oxidative and non-oxidative atmospheres. The viscosity index was determined and improvements in both thermal stability and lubricity were observed with the aid of a modular compact rheometer and a thermos-gravimetric analyzer, respectively. The ETOEE produced may be suitable for use as lubricating oil in gear boxes and engines.
KeywordsBio-lubricant Catalyst-free Epoxidation Tung oil Thermal stability Viscosity
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All author decares that they have no competing interest.
- 5.Mei, D., Luo, Y., Shen, X., Lu, D., Yuan, Y.: Lubrication properties of fatty acid methyl esters as low-sulfur diesel enhancers. Trans Chin Soc Agric Eng 32, 193–197 (2016). https://doi.org/10.11975/j.issn.1002-6819.2016.09.027 Google Scholar
- 6.Nicolau, C., Klein, A., Silva, C., Fiorucci, A., Stropa, J., Santos, E., Borges, K., da Silva, R., de Oliveira, L., Simionatto, E., Scharf, D., Simionatto, E., Nicolau, C.L., Klein, A.N.V., Silva, C.A.A., Fiorucci, A.R., Stropa, J.M., Santos, E.O., Borges, K.C.S., da Silva, R.C.L., de Oliveira, L.C.S., Simionatto, E.L., Scharf, D.R., Simionatto, E.: Thermal properties of the blends of methyl and ethyl esters prepared from babassu and soybean oils. J. Braz. Chem. Soc. 29, 1672–1679 (2018). https://doi.org/10.21577/0103-5053.20180040 Google Scholar
- 7.Miyake, T., Makino, T., Taniguchi, S.I., Watanuki, H., Niki, T., Shimizu, S., Kojima, Y., Sano, M.: Alcohol synthesis by hydrogenation of fatty acid methyl esters on supported Ru-Sn and Rh-Sn catalysts. Appl. Catal. A Gen. 364, 108–112 (2009). https://doi.org/10.1016/j.apcata.2009.05.036 CrossRefGoogle Scholar
- 9.Sustaita-Rodríguez, A., Ramos-Sánchez, V.H., Camacho-Dávila, A.A., Zaragoza-Galán, G., Espinoza-Hicks, J.C., Chávez-Flores, D.: Lipase catalyzed epoxidation of fatty acid methyl esters derived from unsaturated vegetable oils in absence of carboxylic acid. Chem. Cent. J. 12, 1–7 (2018). https://doi.org/10.1186/s13065-018-0409-2 CrossRefGoogle Scholar
- 12.Lee, P.L., Wan Yunus, W.M.Z., Yeong, S.K., Abdullah, D.K., Lim, W.H.: Optimization of the epoxidation of methyl ester of palm fatty acid distillate. J. Oil Palm Res. 21, 675–682 (2009)Google Scholar
- 20.Sutanto, S., Go, A.W., Chen, K.-H., Nguyen, P.L.T., Ismadji, S., Ju, Y.-H.: Release of sugar by acid hydrolysis from rice bran for single cell oil production and subsequent in situ transesterification for biodiesel preparation. Fuel Process. Technol. (2017). https://doi.org/10.1016/j.fuproc.2017.07.014 Google Scholar
- 23.ASTM International: ASTM D2270–04 “Standard Practice for Calculating Viscosity Index from Kinematic Viscosity at 40 and 100 & #xB0; C 1 Liquid Petroleum Products and Opaque Liquids (and the Calculation of Dynamic Viscosity)”. ASTM International, West Conshohocken (2007)Google Scholar