Palladium-Catalyzed α-Monosulfonation of Anthraquinone by Sulfut Trioxide in Liquid Sulfur Dioxide

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Other Title
  • 液体二酸化硫黄中での三酸化硫黄によるアントラキノンのα-スルホン化におけるパラジウムの触媒作用
  • 液体二酸化硫黄中での三酸化硫黄によるアントラキノンのα‐スルホン化におけるパラジウムの触媒作用

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Description

New catalysts which promote selectively the α-sulforiation of anthraquinone in liquid sulfur dioxide [S02(1)] as a solvent were studied. Catalytic activity of transition metals was in the order : Pd>Ru>>Rh, and other metals such as Ti, Mn, Fe, Co, Ni, Cu, Mo, Ag, and Pb were entirely inactive. The activity of palladium compounds was revealed to be in the order: Pd(OAc)2≥Pd-carbon>PdSO44, K2PdC14, Pd(PhCN)2CI2, Pd(PPh3)2CI2>>PdCI2. In the case of the Pd-carbon catalyst, all the Pd-metal was found dissolved in the solution after the reaction. Reaction leading to α-sulfonic acid was much faster and more selective in SO2(1) than in sulfuric acid ; e. g., a mixture of anthraquinone : SO3 : SO22(1) ; Pd(OAc)2=1 : 1.7 : 70 : 0.02 (molarratio) resulted in 100% conversion of anthraquinone after 3h heating at, and gave anthra-quinone ure gave a higher α-selectivity in contrast to the reaction in sulfuric acid. Reprecipitation of the solubilized Pd on carbon by hydrogen treating was also studied.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1980 (3), 322-326, 1980-03-10

    The Chemical Society of Japan

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