The liquid-phase oxidation of hydrocarbons with molecular oxygen. II. A highly selective formation of .ALPHA.-tetralone by the metal-catalyzed oxidation of tetralin in the presence of N,N-dialkylamides.
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概要
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The metal-ion catalyzed oxidation of tetralin was carried out in different solvents in which metal salts tend to be soluble. It was found that, for the production of α-tetralone, a chromium salt is the best catalyst among the first-transition-metal salts employed, while <I>N</I>,<I>N</I>-dialkylamides are the best solvents or the best additives. For example, in the tris(acetylacetonato)chromium(III)-catalyzed oxidation of tetralin in the presence of <I>N</I>,<I>N</I>-dimethylacetamide, α-tetralone was obtained in a 93.0% yield at a 27.2% tetralin conversion. The decomposition of α-tetralyl hydroperoxide (THP) with different first-transition-metal catalysts was also carried out in <I>N</I>,<I>N</I>-dimethylformamide in order to elucidate the formation mechanism for α-tetralone in the oxidation of tetralin in the presence of <I>N</I>,<I>N</I>-dialkylamides. It was concluded that the product distribution in the oxidation mainly depends on the decomposition mechanism of THP, and that <I>N</I>,<I>N</I>-dialkylamides seem to promote the reaction of the α-tetralylperoxyl radical with low valent metal ions, ROO·+M<SUP><I>n</I>+</SUP>→α-tetralone+OH<SUP>−</SUP>+M<SUP>(<I>n</I>+1)+</SUP>.
- 公益社団法人 日本化学会の論文
著者
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MIZUKAMI Fujio
National Chemical Laboratory for Industry
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Horiguchi Yutaka
National Chemical Laboratory for Industry
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- The liquid-phase oxidation of hydrocarbons with molecular oxygen. II. A highly selective formation of .ALPHA.-tetralone by the metal-catalyzed oxidation of tetralin in the presence of N,N-dialkylamides.