Olefins and allylic alcohols have been epoxidized with commercially available hydrogen peroxide (30% H2O2) using a phase transfer catalyst,composed of cetyltrimethylammonium cations and a lacunary-type phosphotungstate anion [PW11O39]7-or the complete Keggin-type heteropolyanion [PW12O40]3-,under two-phase conditions using ethyl acetate as the solvent. It was found that the lacunary-type catalyst showed higher activity and better recyclability than the complete Keggin-type catalyst under the same reaction conditions. 31P NMR spectroscopy and solubility measurements for the two catalysts revealed that the [PW11O39]7-anion had a much faster degradation rate than the [PW12O40]3-anion in an excess of H2O2,which resulted in the formation of more catalytically active species. As a result,the lacunary-type phosphotungstate anion-based catalyst gave a better catalytic performance than the complete Keggin-type anion in ethyl acetate.
