Epoxidation of cycloolefins with hydrogen peroxide in the presence of heteropoly acids combined with phase transfer catalyst |
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Authors: | Timofeeva M. N. Pai Z. P. Tolstikov A. G. Kustova G. N. Selivanova N. V. Berdnikova P. V. Brylyakov K. P. Shangina A. B. Utkin V. A. |
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Affiliation: | (1) G. K. Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences, 5 prosp. Akad. Lavrent"eva, 630090 Novosibirsk, Russian Federation |
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Abstract: | Oxidation of cycloolefins (cyclohexene, cyclooctene, and cyclododecene) with a 30% solution of hydrogen peroxide at 65 °C in the presence of heteropoly acids (HPA) H3PW12–xMoxO40 (x = 0—12), which are precursors of active peroxo complexes, and phase transfer catalysts Q+Cl–, where Q+ is the quaternary ammonium cation containing C4—C18 alkyl groups or [C5H5NC16H33]+, was studied. The catalytic activity decreases in the HPA series: H3PW12O40 > H3PW9Mo3O40 > H3PW6Mo6O40 > H3PW3Mo9O40 > H3PMo12O40. The state of the H3PW12O40—I2I2 system was studied using UV, IR, and 31P NMR spectroscopies with variation of the [H2O2] : [HPA] ratio from 2 to 200 during cyclohexene epoxidation. Despite different catalytic precursors, the reaction proceeds through the same peroxo complex. |
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Keywords: | oxidation of cyclic olefins phase transfer catalysis heteropoly acids |
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