Highly Selective Metathesis of 1-Octene in Ionic Liquids

Abstract

The self-metathesis of 1-octene to form 7-tetradecene catalyzed by ruthenium carbene complexes at low concentrations (0.02 mol %) was investigated in ionic liquids as reaction media and as additives. The study showed that the ionic liquid has a significant effect on the selectivity of the metathesis of 1-octene, with conversion to product of greater than 95% being obtained and selectivities of over 98% being realized. The outcomes of the reactions compared well with those performed under solventless conditions, showing improved conversions and selectivities.

Alkene Metathesis Catalysis: A Key for Transformations of Unsaturated Plant Oils and Renewable Derivatives

“…Ionic Liquids (IL) as solvents have shown their ability to favour several catalytic processes [28][29][30][31][32] and alkene metathesis can be performed in Room Temperature Ionic Liquids (RTIL) since 1995 [33][34][35][36][37][38][39][40][41]. We have shown the efficient ethenolysis of methyl oleate 1 under mild conditions with several ruthenium alkylidene catalysts in organic solvents and, for the first time, in imidazolium-type ionic liquids at room temperature without C=C bond isomerization [42].…”

Platinum complexes of malonate-derived monodentate phosphines and their application in the highly chemo- and regioselective hydroformylation of styrene

“…While the conversion is negligible under 80 bar pressure (CO/H 2 = 1:1), complete conversion may be obtained under 110 bar pressure (compare entries 7, 8 and 9). Ionic liquids have been found useful in a number of catalyst systems for several reactions including metathesis [25] and hydroformylation [26] reactions. Ligand 4 was expected to be a suitable ligand in ionic liquid catalysis due to the presence of the two polar hydroxyl groups enabling good solubility.…”

Mixed Isobutylphobane/N‐Heterocyclic Carbene Ruthenium‐ Indenylidene Complexes: Synthesis and Catalytic Evaluation in Olefin Metathesis Reactions

“…[27] Further enhancement of the catalytic efficiency of 5 could be achieved by the addition of diverse co-catalysts, such as phenols, [28] tin and iron halogenides, [29] or ionic liquids. [30] A stoichiometric reaction of 5 with 2-isopropoxystyrene afforded the chelated alkoxybenzylidene compound 7, which was found to be highly active at promoting the RCM of N,N-diallyltosylamide. [31] In the indenylidene series, the first generation di(cyclohexylphobane) complex 8 A C H T U N G T R E N N U N G (PPh 3 ) 2 ] and an isomeric mixture of cyclohexylphobanes.…”