Abstract
One of the most important areas of green chemistry is the application of environmentally friendly solvents in catalysis and synthesis. Conventional organic solvents pose a threat to the environment due to the volatility, highly flammability, toxicity and carcinogenic properties they exhibit. The recently emerged room temperature ionic liquids (RTILs) are promising green solvent alternatives to the volatile organic solvents due to their ease of reuse, non-volatility, thermal stability and ability to dissolve a variety of organic and organometallic compounds. This review explores the use of RTILs as green solvent media in olefin metathesis for applications in the oleochemical industry.
Highlights
Olefin metathesis was discovered by Banks and Bailey in 1964, while looking for an effective heterogeneous catalyst to replace hydrogen fluoride for converting olefins into high-octane gasoline via olefin-isoparaffin alkylation [1]
Liquid phase (SILP) catalyst prepared with the Ionic liquids (ILs) 1-isopentyl-3-methylimidazole hexafluorophosphate showed a turnover number almost twice that of biphasic systems)
Ring closing metathesis metathesis has been been successfully employed employed in the the synthesis of of macrocyclic macrocyclic compounds from from olefinic fatty compounds in conventional organic solvents
Summary
Olefin metathesis was discovered by Banks and Bailey in 1964, while looking for an effective heterogeneous catalyst to replace hydrogen fluoride for converting olefins into high-octane gasoline via olefin-isoparaffin alkylation [1]. Olefin metathesis is an alkylidene exchange reaction (Scheme 1) between two reacting alkenes, mediated by transition metal alkylidene complexes [7]. The reaction involves the exchange of ions to produce the most stable ion pairs (Scheme 1a) [8] It follows the Chauvin mechanism in which carbon-carbon double bonds are ruptured and new bonds are formed (1b) [9]. The process involves the reaction between an olefin and a transition metal alkylidene complex in a [2+2] fashion to generate an unstable metallacyclobutane intermediate. This cyclobutane intermediate rearranges to form a new metal carbene and an olefin (Scheme 1b) [9].
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