Continuous-flow alkene metathesis

The self-metathesis of 1-octene was used as a model reaction to demonstrate the performance of a continuous-flow alkene metathesis process using supercritical CO2 as the carrier.

Over the last decade or so, olefin metathesis has become widely recognised as a good, general method to generate new C–C bonds, with an excellent synthetic scope.  Here, an international collaboration of scientists from University Ca’Foscari (Italy), the University of Nottingham (UK) and the University of Sydney (Australia) led by Maurizio Selva have developed a continuous-flow process for heterogeneously-catalysed olefin metathesis.

Their process used a Re2O7 supported catalyst on γ-Al2O3, which although deactivated after the first 100-150 mins of the reaction, could be recycled for at least five subsequent reactions without any loss of performance.  Improving this aspect further will be the focus of future research in this area.  The authors propose that this methodology will be applicable to the metathesis of other terminal olefins in the C6-C12range of liquid compounds.

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Continuous-flow alkene metathesis: the model reaction of 1-octene catalyzed by Re2O7/γ-Al2O3with supercritical CO2 as a carrier, Maurizio Selva, Sandro Guidi, Alvise Perosa, Michela Signoretto, Pete Licence and Thomas Maschmeyer, Green Chem., 2012, DOI: 10.1039/C2GC35983A    (Advanced Article)

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