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Solvent-free oxidation of cumene by molecular oxygen catalyzed by cobalt salen-type complexes

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Abstract

Co(salen)-type [where salen = di-(salicylal)-ethylenediimine] complexes were shown to be efficient catalysts in the oxidation of 2-phenylpropane (cumene) by dioxygen primarily to 2-phenyl-2-propanol (cumyl alcohol), 2-phenylpropene (α-methylstyrene), and 1-phenylethanone (acetophenone) applying 1H NMR spectroscopy and gas chromatography–mass spectrometry (GC–MS). The effect of substitution on the ligand was also monitored in both oxygen-absorption and the catalytic reaction. Based on these results, the trend observed for the production of α-methylstyrene and cumyl alcohol were parallel to dioxygen uptake by the catalyst in neat cumene, while acetophenone productions obeyed a non-linear trend. The best selectivity for the reaction in terms of acetophenone production was observed for the complex with the least oxygen-absorption feature. The intermediate of the reaction, LCo(III)-OOcumyl (where L = salen) complex, was synthesized and characterized by IR, 1H NMR spectroscopy as well as elemental analysis, and its reactivity in the present catalytic reaction was also studied. A series of experiments were performed to propose a mechanism for the reaction on the basis of the product distributions in the reaction mixture.

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Acknowledgment

Financial support from Research Office of Sharif University of Technology is acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Sharif University of Technology, PO Box 11155-3516, Tehran, Iran

    B. Ghanbari, S. R. Ferdosi & H. Tafazolian

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  1. B. Ghanbari
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  3. H. Tafazolian
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Correspondence to B. Ghanbari.

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Ghanbari, B., Ferdosi, S.R. & Tafazolian, H. Solvent-free oxidation of cumene by molecular oxygen catalyzed by cobalt salen-type complexes. Res Chem Intermed 38, 871–883 (2012). https://doi.org/10.1007/s11164-011-0425-5

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