Abstract
10,11-Dioctyleicosane, a star-shaped hydrocarbon, has been successfully synthesized from 9-octadecene (a product from metathesis of methyl oleate or ethyl oleate) through dimerization followed by hydrogenation. The product was determined by13C nuclear magnetic resonance spectroscopic and gas chromatography/mass spectrometric techniques. This hydrocarbon likely exhibits lubricating properties that can be used as high-performance functional fluids in automotive lubrication. We also report the presence of a novel product, a trimer that was formed during the synthesis.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Choo, Y.M., K.E. Ooi, and I.H. Ooi, Synthesis of Civetone from Palm Oil Products,J. Am. Oil Chem. Soc. 71:911–913 (1994).
Sullivan, F.W., Jr., V. Vorhees, A.W. Neeley, and R.V. Shankland, Synthetic Lubricating Oils. Relation Between Chemical Constitution Properties,Ind. Eng. Chem. 23:604–611 (1931).
Montgomery, C.W., W.I, Gilbert, and R.E. Kline, Polymeric Lubricating Oils, U.S. Patent 2,559,984 (1951).
Brennan, J.A., Polymerization of Olein with BF3, U.S. Patent 3,382,291 (1968).
Shubkin, R.L., Process for Producing a C6−C16 Normal Alpha Olefin Oligomer Having a Pour Point About-50°F, U.S. Patent 3,763, 244 (1973).
Shubkin, R.L., Synthetic Lubricants by Oligomerization and Hydrogenation, U.S. Patent 3,780,128 (1973).
Shubkin, R.L., M.S. Baylerian, and A.R. Maler, Olefin Oligomers: Structure and Mechanism of Formation, presented at the Symposium on Chemistry of Synthetic Lubricants and Additives, September 9–14, 1979, American Chemical Society, Washington, D.C., 1979, pp. 809–817.
Choo, Y.M., A.S.H. Ong, K.Y. Cheah, and A. Bakar, Production of Alkyl Esters from Oils and Fats, Australia Patent No. 43519/89 (1992).
Van Dam, P.B., M.C. Mittelmeijer, and C. Boelhouwer, Metathesis of Unsaturated Fatty Acid Esters by Homogeneous Tungsten Hexachloride-Tetramethyltin Catalyst,J. Chem. Soc. Chem. Commun., 1221–1222 (1972).
Van Dam, P.B., M.C. Mittelmeijer, and C. Boelhouwer, Homogeneous Catalytic Metathesis of Unsaturated Fatty Esters: New Synthetic Method for Preparation of Unsaturated Mono-and Di-Carboxylic Acids,J. Am. Oil Chem. Soc. 51:389–392 (1974).
Van Dam, P.B., M.C. Mittelmeijer, and C. Boelhouwer, Catalytic Metathesis of Esters and Unsaturated Fatty Acids,Fette Seifen Anstrichm. 76:264–266 (1974).
Author information
Authors and Affiliations
About this article
Cite this article
Choo, YM., Ooi, KE., Ooi, IH. et al. Synthesis of a palm-based star-shaped hydrocarbonvia oleate metathesis. J Am Oil Chem Soc 73, 333–336 (1996). https://doi.org/10.1007/BF02523427
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02523427