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An Improved Catalytic Performance of Fe(III)-promoted NHPI in the Oxidation of Hydrocarbons to Hydroperoxides

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Abstract

N-hydroxyphthalimide (NHPI) is a promising catalyst in aerobic oxidation of hydrocarbons to corresponding hydroperoxides. We have found that a trace amount of Fe(benz)3 or Fe(acac)3 (in concentration of less than 10−1 mmol/l and with the ratio of Fe(III): NHPI = 1:500) considerably accelerates the oxidation of cyclohexene and ethylbenzene, while retaining the selectivity to hydroperoxides at a level of 90%. As a consequence, the reaction temperature could be lowered down to 50–60 °C. The promoting effect of the additives was attributed to the ability of Fe(III) complexes to generate phthalimido-N-oxyl radicals (PINO) without participation in any transformations of hydrocarbon intermediates and hydroperoxides, thus ensuring selective formation and stability of the hydroperoxides.

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Acknowledgements

We are thankful to Dr. T.V. Larina for UV–Vis spectroscopy. This work was supported by budget project No 0303-2016-0006 for Boreskov Institute of Catalysis.

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  1. Boreskov Institute of Catalysis SB RAS, Novosibirsk, Russia

    N. I. Kuznetsova, L. I. Kuznetsova, O. A. Yakovina, I. E. Karmadonova & B. S. Bal’zhinimaev

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  1. N. I. Kuznetsova
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  2. L. I. Kuznetsova
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  3. O. A. Yakovina
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  4. I. E. Karmadonova
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  5. B. S. Bal’zhinimaev
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Correspondence to N. I. Kuznetsova.

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Kuznetsova, N.I., Kuznetsova, L.I., Yakovina, O.A. et al. An Improved Catalytic Performance of Fe(III)-promoted NHPI in the Oxidation of Hydrocarbons to Hydroperoxides. Catal Lett 150, 1020–1027 (2020). https://doi.org/10.1007/s10562-019-02999-x

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