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Selective Hydrodeoxygenation of Cyclic Vicinal Diols to Cyclic Alcohols over Tungsten Oxide–Palladium Catalysts

Authors

  • Dr. Yasushi Amada,

    1. Department of Applied Chemistry, School of Engineering, Tohoku University, Aoba 6-6-07, Aramaki, Aoba-ku, Sendai, 980-8579 (Japan)
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  • Nobuhiko Ota,

    1. Department of Applied Chemistry, School of Engineering, Tohoku University, Aoba 6-6-07, Aramaki, Aoba-ku, Sendai, 980-8579 (Japan)
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  • Dr. Masazumi Tamura,

    1. Department of Applied Chemistry, School of Engineering, Tohoku University, Aoba 6-6-07, Aramaki, Aoba-ku, Sendai, 980-8579 (Japan)
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  • Dr. Yoshinao Nakagawa,

    Corresponding author
    1. Department of Applied Chemistry, School of Engineering, Tohoku University, Aoba 6-6-07, Aramaki, Aoba-ku, Sendai, 980-8579 (Japan)
    • Department of Applied Chemistry, School of Engineering, Tohoku University, Aoba 6-6-07, Aramaki, Aoba-ku, Sendai, 980-8579 (Japan)===

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  • Prof. Keiichi Tomishige

    Corresponding author
    1. Department of Applied Chemistry, School of Engineering, Tohoku University, Aoba 6-6-07, Aramaki, Aoba-ku, Sendai, 980-8579 (Japan)
    • Department of Applied Chemistry, School of Engineering, Tohoku University, Aoba 6-6-07, Aramaki, Aoba-ku, Sendai, 980-8579 (Japan)===

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Abstract

Hydrodeoxygenation of cyclic vicinal diols such as 1,4-anhydroerythritol was conducted over catalysts containing both a noble metal and a group 5–7 transition-metal oxide. The combination of Pd and WOx allowed the removal of one of the two OH groups selectively. 3-Hydroxytetrahydrofuran was obtained from 1,4-anhydroerythritol in 72 and 74 % yield over WOx–Pd/C and WOx–Pd/ZrO2, respectively. The WOx–Pd/ZrO2 catalyst was reusable without significant loss of activity if the catalyst was calcined as a method of regeneration. Characterization of WOx–Pd/C with temperature-programmed reduction, X-ray diffraction, and transmission electron microscopy/energy-dispersive X-ray spectroscopy suggested that Pd metal particles approximately 9 nm in size were formed on amorphous tungsten oxide particles. A reaction mechanism was proposed on the basis of kinetics, reaction results with tungsten oxides under an atmosphere of Ar, and density functional theory calculations. A tetravalent tungsten center (WIV) was formed by reduction of WO3 with the Pd catalyst and H2, and this center served as the reductant for partial hydrodeoxygenation.

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