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Epoxidation of olefins with hydrogen peroxide catalyzed by a reusable lacunary-type phosphotungstate catalyst

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Abstract

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.

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Authors and Affiliations

  1. Key Laboratory for Advanced Materials; Research Institute of Industrial Catalysis, East China University of Science and Technology, Shanghai, 200237, China

    Li Hua, YunXiang Qiao, Huan Li, Bo Feng, ZhenYan Pan, YinYin Yu, WenWen Zhu & ZhenShan Hou

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  1. Li Hua
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  2. YunXiang Qiao
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  3. Huan Li
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  4. Bo Feng
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  5. ZhenYan Pan
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  6. YinYin Yu
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  7. WenWen Zhu
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  8. ZhenShan Hou
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Correspondence to ZhenShan Hou.

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Hua, L., Qiao, Y., Li, H. et al. Epoxidation of olefins with hydrogen peroxide catalyzed by a reusable lacunary-type phosphotungstate catalyst. Sci. China Chem. 54, 769–773 (2011). https://doi.org/10.1007/s11426-011-4251-9

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