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Issue 6, 2011
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Styrene oxidation by hydrogen peroxide in ionic liquids: the role of the solvent on the competition between two Pd-catalyzed processes, oxidation and dimerization

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Abstract

A series of hydrophilic N,N-dimethylpyrrolidinium- and N,N-dimethylpiperidinium-based ionic liquids (ILs) have been prepared and applied as reaction media in the Wacker oxidation of styrene by hydrogen peroxide using PdCl2 as the catalyst. The efficiency of these ILs was compared with hydrophilic and hydrophobic imidazolium systems (including those with nitrile functionalities). The nature of the ionic liquid strongly influences the product distribution. In particular, in hydrophobic ILs, relevant amounts of 1,3-diphenyl-1-butene arising from styrene dimerization were detected, in addition to the expected phenylmethylketone. The formation of 1,3-diphenyl-1-butene may be attributed to the formation of Pd(0) species from “ClPdOH” (probably formed during the Wacker process) in a side-reaction. Consequently, the ability of the IL to favor or disfavor the reoxidation of “ClPdOH” to “ClPdOOH” by hydrogen peroxide, giving an homogeneous phase or a biphasic system, appears to be the main factor affecting selectivity.

Graphical abstract: Styrene oxidation by hydrogen peroxide in ionic liquids: the role of the solvent on the competition between two Pd-catalyzed processes, oxidation and dimerization

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Publication details

The article was received on 23 Dec 2010, accepted on 07 Mar 2011 and first published on 11 Apr 2011


Article type: Paper
DOI: 10.1039/C0GC00945H
Citation: Green Chem., 2011,13, 1437-1441

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    Styrene oxidation by hydrogen peroxide in ionic liquids: the role of the solvent on the competition between two Pd-catalyzed processes, oxidation and dimerization

    C. Chiappe, A. Sanzone and P. J. Dyson, Green Chem., 2011, 13, 1437
    DOI: 10.1039/C0GC00945H

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