Autoxidation of 2, 6-Dimethylnaphthalene Catalyzed by Co-Mn-Br Catalyst in Acetic Acid

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  • KAMIYA Yoshio
    Department of Reaction Chemistry, Faculty of Engineering, University of Tokyo
  • TAGUCHI Toshiki
    Department of Reaction Chemistry, Faculty of Engineering, University of Tokyo
  • FUTAMURA Shigeru
    Department of Reaction Chemistry, Faculty of Engineering, University of Tokyo

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Other Title
  • Co-Mn-Br系触媒による2,6-ジメチルナフタレンの液相酸素酸化
  • Co Mn Brケイ ショクバイ ニ ヨル 2 6 ジメチルナフタレン ノ エ

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Description

The effects of some reaction conditions on the autoxidation of 2, 6-dimethylnaphthalene catalyzed by cobalt-manganese-bromide ions in acetic acid were studied at temperatures of 65 to 200°C. The oxidation of each methyl substituent proceeded one after another to carboxylic acid via aldehyde by successive reaction (Figs.3, 4). The conversion of substrate was remarkably decreased with increasing substrate concentration (Figs.1, 2), suggesting that the presence of naphthalene ring retarded the oxidation reaction. It was also observed that the rate of oxidation was gradually decreased as the bromide, ion was converted to the inactive form of organic bromide (Fig.7). Although methyl substituents on naphthalene ring can be oxidized faster tian those on benzene ring (Figs.5, 6), the overall oxidation of 2, 6-dimethylnaphthalene proceeded rather slowly at 90°C, because of some retardation effects above mentioned and low solubility, of folmylnaphthoic acid in acetic acid. However, the oxidation of substrate to 2, 6-naphthalenedicarboxylic acid proceeded smoothly at 150°C under oxygen pressure of 10 bar, restating in a good yield as high as 85% (Table 5).

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1987 (10), 1772-1778, 1987-10-10

    The Chemical Society of Japan

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