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

Solvent-free oxidation of cumene by molecular oxygen catalyzed by cobalt salen-type complexes 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

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

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Publisher
Springer Netherlands
Copyright
Copyright © 2011 by Springer Science+Business Media B.V.
Subject
Chemistry; Catalysis; Inorganic Chemistry; Physical Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-011-0425-5
Publisher site
See Article on Publisher Site

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.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Nov 10, 2011

References

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