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Issue 1, 2014
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Eco-friendly solvents and amphiphilic catalytic polyoxometalate nanoparticles: a winning combination for olefin epoxidation

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Abstract

Eighteen eco-friendly solvents were examined to carry out the epoxidation of olefins with the amphiphilic catalytic dodecyltrimethylammonium polyoxometalate nanoparticles [C12]3[PW12O40] in comparison with [H]3[PW12O40] and [Na]3[PW12O40]. Surprisingly, the screening of solvents with cyclooctene has revealed that the [C12]3[PW12O40] catalyst is much more active with initial turn-over frequencies, TOF0, increasing up to a factor of 10. Moreover, the reaction occurs at competitive rates in four relevant solvents, i.e. cyclopentyl methyl ether, 2-methyl tetrahydrofuran, methyl acetate and glycerol triacetate, for which TOF0 values are higher than 260 h−1. The recyclability of the systems is demonstrated and the scope of substrates has been successfully extended to cyclohexene, 1-octene, limonene, 3-carene, α-pinene, β-pinene and neryl acetate with good epoxide selectivity. The catalytic performances in the “green” solvent are assigned to the formation of stable [C12]3[PW12O40] nanoparticle dispersions which have been characterized by transmission electron microscopy and dynamic and multiple light scattering experiments. Finally, the Kamlet–Taft parameters were measured in order to correlate the physicochemical properties of the solvents and the catalytic activity.

Graphical abstract: Eco-friendly solvents and amphiphilic catalytic polyoxometalate nanoparticles: a winning combination for olefin epoxidation

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Publication details

The article was received on 30 Sep 2013, accepted on 25 Oct 2013 and first published on 25 Oct 2013


Article type: Paper
DOI: 10.1039/C3GC42032A
Citation: Green Chem., 2014,16, 269-278
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    Eco-friendly solvents and amphiphilic catalytic polyoxometalate nanoparticles: a winning combination for olefin epoxidation

    A. Mouret, L. Leclercq, A. Mühlbauer and V. Nardello-Rataj, Green Chem., 2014, 16, 269
    DOI: 10.1039/C3GC42032A

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