Highly Active and Selective Semihydrogenation of Alkynes with the Palladium Nanoparticles-Tetrabutylammonium Borohydride Catalyst System

Authors

  • Junichi Hori,

    1. Central Research Laboratory, Technology and Development Division, Kanto Chemical Co., Inc., Soka, Saitama 340-0003, Japan
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  • Kunihiko Murata,

    1. Central Research Laboratory, Technology and Development Division, Kanto Chemical Co., Inc., Soka, Saitama 340-0003, Japan
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  • Toshiki Sugai,

    1. Department of Chemistry, Graduate School of Science and Research Center for Materials Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan
    2. Present address: Department of Chemistry, Faculty of Science, Toho University, 2-2-1 Miyama, Funabashi 274-8510, Japan
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  • Hisanori Shinohara,

    1. Department of Chemistry, Graduate School of Science and Research Center for Materials Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan
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  • Ryoji Noyori,

    1. Department of Chemistry, Graduate School of Science and Research Center for Materials Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan
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  • Noriyoshi Arai,

    1. Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan, Fax: (+81)-11-706-6598
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  • Nobuhito Kurono,

    1. Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan, Fax: (+81)-11-706-6598
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  • Takeshi Ohkuma

    1. Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan, Fax: (+81)-11-706-6598
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Abstract

Palladium nanoparticles are prepared from palladium(II) acetate and 2 equivalents of potassium tert-butoxide in the presence of 4-octyne. The palladium nanoparticles-tetrabutylammonium borohydride system shows excellent catalytic activity and selectivity in the semihydrogenation of alkynes to the [(Z)-]alkenes. The hydrogenation of 4-octyne is conducted with the catalyst system at a substrate-to-palladium molar ratio of 10,000–200,000 under 8 atm of hydrogen to give (Z)-4-octene in>99% yield. Isomerization and over-reduction of the Z-alkene are very slow even after consumption of the alkyne.

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