Synthesis of palm-based ethylhexyl ester as a synthetic base oil for drilling fluids using chemical transesterification
DOI:
https://doi.org/10.3989/gya.074513Keywords:
Ethylhexyl ester, Gas chromatography, Optimization, Reaction parametersAbstract
In the present study the synthesis of a palm based ethylhexyl ester was examined through a transesterification reaction of palm oil methyl ester (POME) with 2-ethylhexanol (EH). A sodium methoxide in methanol solution was used as a catalyst. The reaction was carried out at a fixed pressure of 1.5 mbar by varying the temperature (80–140 °C), POME/2EH molar ratio (1:1.5–1:2.2), reaction time (0.5–4 h) and catalyst concentration (1–2% w/w). The reaction with 2-ethylhexanol involved a single step reversible reaction, thus, the reaction was completed in a very short time. The optimum conditions were obtained in less than 30 minutes with 1.5 mbar pressure, 70 °C, and 1:2 molar ratio of POME to 2EH. The analysis of the final product (ethylhexyl ester) was performed using gas chromatography which exhibited 98% of ethyl hexyl ester yield. The gas chromatography analysis of ethyl hexyl ester revealed two major esters peaks i.e. ethyl hexyl palmitate and ethylhexyl oleate.
Downloads
References
Asadauskas S, Erhan SZ. 1999. Depression of pour points of vegetable oils by blending with diluents used for biodegradable lubricants. J. Am. Oil Chem. Soc. 76, 313–316. http://dx.doi.org/10.1007/s11746-999-0237-6
Berthezene N, de Hemptinne JC, Audibert A, Argillier J.-F. 1999. Methane solubility in synthetic oil-based drilling muds. J. Petro. Sci. Eng. 23, 71–81. http://dx.doi.org/10.1016/S0920-4105(99)00008-X
Chen JK, Wang JF, Chen SF, Duan LZ. 1999. J. Anhiu. Agric. Teachers Coll. 13: (1999).
Filippis DE, Giavarini C, Scarsella M, Sorrentino M. 1995. Transesterification processes for vegetable oils: A simple control method of methyl ester content. J. Am. Oil Chem. Soc. 72, 1399–1404. http://dx.doi.org/10.1007/BF02546218
García-Zapateiro LA, Delgado, MA, Franco JM, Valencia C, Ruiz-Méndez MV, Garcés R, Gallegos C. 2010. Oleins as a source of estolides for biolubricant applications, Grasas Aceites, 61, 171–174. http://dx.doi.org/10.3989/gya.075209
He XL, Chen Bi-Q, Tan T-W. 2002. Enzymatic synthesis of 2-ethylhexyl esters of fatty acids by immobilized lipase from Candida sp. 99–125. J. Mol. Catal. B. 18, 333–339. http://dx.doi.org/10.1016/S1381-1177(02)00114-5
Herrmann C, Hesselbach J, Bock R, Zein A, Ohlshlager G, Dettmer T. 2007. Ecologically benign lubricants – evaluation from a life cycle perspective. Clean-Soil, Air, Water 35, 427–432. http://dx.doi.org/10.1002/clen.200720025
Lamsa M, Huhtala A, Linko YY, Linko P. 1994. 2-ethyl-1-hexanol fatty acid esters from rapeseed oil by transesterification. Biotech. Tech. 8, 451–456. http://dx.doi.org/10.1007/BF00154320
Linko YY, Lamsa M, Huhtala A, Linko P. 1994. Lipase-catalyzedtransesterification of rapeseed oil and 2-ethyl-l-hexanol. J. Am. Oil Chem. Soc. 71, 1411–1414. http://dx.doi.org/10.1007/BF02541364
Liu Y, Lotero E, Goodwin JJG. 2006. Effect of water on sulfuric acid catalyzed esterification. J. Mol. Catal. A, 245, 132–140. http://dx.doi.org/10.1016/j.molcata.2005.09.049
May CY, Foon CS, Ngan MA, Basiron Y. 2005. Lubricant base oil of palm fatty acid origin. European Patent Application. EP 1529828A1.
Nieendick CK, Schmid K, Mueller HM, Herold CP. 1995. Process for cold cleaning oil-contaminated metal surfaces with 2-ethylhexyl esters of fatty acids. United States Petent, 5421907.
Nomura M, Nishiyama K, Masanori, Ishii, H. 2005. Drier for printing ink and printing ink containing drier. United States Patent 6899756 B2.
Salih N, Salimon J, Yousif E. 2011. Synthesis of oleic acid based esters as potential basestock for biolubricant production. Tur. J. Eng. Environ. Sci. 35, 115–123.
Salimon J, Salih N, Yousif E, 2010. Biolubricants: raw materials, chemical modifications and environmental benefits. Eur. J. Lipid Sci. Technol. 112, 519–530.
Sánchez R, Franco JM, Delgado MA, Valencia C, Gallegos C. 2011. Rheology of oleogels based on sorbitan and glycerylmonostearates and vegetable oils for lubricating applications, Grasas Aceties 62, 328–336. http://dx.doi.org/10.3989/gya.113410
SernCH, May CY, Zakaria Z, Daik R. 2008. Synthesis of palmitic acid-based esters and their effect on the pour point of palm oil methyl esters. J. Oil Palm Res. 20, 542–547.
Su EZ, You PY, Wei DZ. 2009. In situ lipase-catalyzed reactive extraction of oilseeds with short-chained dialkyl carbonates for biodiesel production. Bioresource Technol. 100, 5813–5817. http://dx.doi.org/10.1016/j.biortech.2009.06.077
Tan T, Chen Bi-Q, Ye H. 2006. Enzymatic synthesis of 2-ethylhexyl palmitate by lipase immobilized on fabric membranes in the batch reactor. Biochem. Eng. J. 29, 41–45. http://dx.doi.org/10.1016/j.bej.2005.02.033
Tan T, Chen BQ, Ye H. 2005. Synthesis of 2-ethylhexyl palmitate by lipase immobolized on fabric membranes in batch reactor. Biochem Eng. J. 29, 41–45. http://dx.doi.org/10.1016/j.bej.2005.02.033
Uosukainen E, Linko YY, Lamsa M, Tervakangas T, Linko P. 1998. Transesterification of tromethylolpropane and rapeseed oil methyl ester to environmentally acceptable lubricants. J. Am. Oil Chem. Soc. 75, 1557–1563. http://dx.doi.org/10.1007/s11746-998-0094-8
Wang Y, Cao X. 2011. Enzymatic synthesis of fatty acid ethyl esters by utilizing camellia oil soapstocks and diethyl carbonate. Bioresource Technol. 102, 10173–10179. http://dx.doi.org/10.1016/j.biortech.2011.09.004
Waskitoaji W, Triwulandari E, Haryono A. 2012. Synthesis of plasticizers derived from palm oil and their application in polyvinyl chloride. Procedia. Chem. 4, 313–321. http://dx.doi.org/10.1016/j.proche.2012.06.044
Yunus R, Fakhru'l-Razi A, Ooi TL, Awang BDR, Iyuke SE. 2004. Kinetics of transesterification of palm-based methyl esters with trimethylolpropane. J. Am. Oil Chem. Soc. 81, 497–503. http://dx.doi.org/10.1007/s11746-004-0930-7
Yunus R, Fakhru'l-Razi A, Ooi TL, Omar R, Idris A. 2005. Synthesis of palm oil based trimethylolpropane esters with improved pour points. Ind. Eng. Chem. Res. 44, 8178–8183. http://dx.doi.org/10.1021/ie050530+
Yunus R. 2003. Synthesis of palm-based trimethylolpropane esters and their potential as lubricant base stock. Unpublished doctoral dissertation, Universiti Putra Malaysia, Malaysia.
Published
How to Cite
Issue
Section
License
Copyright (c) 2014 Consejo Superior de Investigaciones Científicas (CSIC)
This work is licensed under a Creative Commons Attribution 4.0 International License.
© CSIC. Manuscripts published in both the print and online versions of this journal are the property of the Consejo Superior de Investigaciones Científicas, and quoting this source is a requirement for any partial or full reproduction.
All contents of this electronic edition, except where otherwise noted, are distributed under a Creative Commons Attribution 4.0 International (CC BY 4.0) licence. You may read the basic information and the legal text of the licence. The indication of the CC BY 4.0 licence must be expressly stated in this way when necessary.
Self-archiving in repositories, personal webpages or similar, of any version other than the final version of the work produced by the publisher, is not allowed.
