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Sodium dodecylsulphate-catalyzed hetero-aromatic nitrogen base-promoted chromium(VI) oxidation of 2-propenol to 2-propenal in aqueous media

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Abstract

A kinetic study of homogeneously micelle-catalyzed, hetero-aromatic N-base (2-picolinic acid, 2,2′-bipyridine and 1,10-phenanthroline)-promoted oxidation of 2-propenol by chromium(VI) in sulfuric acid medium was carried out at 303 K. The pseudo first-order rate constant (k obs) of the oxidation reaction is directly proportional to [H+] and [promoters], which indicates that the reaction is first order with respect to H+ and promoters. The reaction was conducted at four different temperatures from which the activation parameters were calculated. Proton nuclear magnetic resonance (1H-NMR) studies were performed to detect the location of reactant molecules in nanometer-sized micelles. From the observed kinetic results, a suitable mechanism consistent with the rate law has been proposed. The micelles produced a catalytic effect in the entire range of sodium dodecylsulphate (SDS) concentrations used, and the effect is explained by pseudo-phase ion exchange. The combination of 2,2′-bipyridine (bipy) and SDS exhibited a 15-fold rate enhancement of Cr(VI) oxidation of 2-propenol to 2-propenal.

Graphical Abstract

Ultraviolet-visible (UV-Vis) spectrum of reaction mixture for the Cr(VI) oxidation of 2-propenol with varying solution colour at different reaction times. Right: Location of reactant molecule in the micellar pseudophase region.

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Acknowledgments

Thanks to UGC ((F. No. 33-495/2007 (SR) dated 28.02.2008), New Delhi and CSIR 01 (2463)/11/EMR-II, Dated 16-05-2011), New Delhi for providing financial help in the form of a project and fellowship. The authors are grateful to Sudipta Bhowmick and Visva-Bharati for fruitful discussions in the course of this work.

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Correspondence to Bidyut Saha.

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Sar, P., Ghosh, A., Malik, S. et al. Sodium dodecylsulphate-catalyzed hetero-aromatic nitrogen base-promoted chromium(VI) oxidation of 2-propenol to 2-propenal in aqueous media. Res Chem Intermed 41, 10151–10168 (2015). https://doi.org/10.1007/s11164-015-2019-0

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