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1 Homo-metathesis reaction of methyl oleate In 1972, Boelhouwer and co-workers reported the selective transformation of methyl oleate to equimolar amounts of 9-octadecene and dimethyl 9-octadecene-1,18-dioate using WCl6/(CH3)4Sn as the catalyst (Figure 24) [42]. The successful metathesis of methyl oleate has led to the synthesis of many other unsaturated fatty acid esters with high selectivity. The development of homogeneous and heterogeneous catalyst systems and the metathesis of -unsaturated fatty acid esters such as methyl 10-undecenoate, that proceeds to completion via the continuous removal of the volatile co-product, ethylene, is an example of an industrial process based on these reactions (Figure 25).

Journal of the American Oil Chemists' Society 1984, 61 (2), 276-281. [42] van Dam, P. ; Mittelmeijer, M. , Metathesis of unsaturated fatty acid esters by a homogeneous tungsten hexachloride-tetramethyltin catalyst. Journal of the Chemical Society, Chemical Communications 1972, (22), 1221-1222. [43] Mol, J. , Catalytic Metathesis of Unsaturated Fatty Acid Esters and Oils. Topics in Catalysis 2004, 27 (1), 97-104. [44] Yadav, G. ; Doshi, N. , Development of a green process for poly-[small alpha]-olefin based lubricants.

Microwave-assisted conversion of lignocellulosic biomass into furans in ionic liquid. , 2010, 101 (3), 1111-1114. , Ionic liquids and catalysis: Recent progress from knowledge to applications. Appl. Catal. A: General 2010, 373 (1-2), 1-56. ; Holbrey, J. ; Griffin, S. ; Reichert, W. ; Swatloski, R. ; Katritzky, A. ; Rogers, R. , Ionic liquids via reaction of the zwitterionic 1,3-dimethylimidazolium-2-carboxylate with protic acids. Overcoming synthetic limitations and establishing new halide free protocols for the formation of ILs.

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