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Choice of suitable micellar catalyst for 2,2′-bipyridine-promoted chromic acid oxidation of glycerol to glyceraldehyde in aqueous media at room temperature

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Abstract

The micellar catalyzed 2,2′-bipyridine (bipy)-promoted oxidation of glycerol to glyceraldehyde by chromic acid is investigated under the criteria [glycerol]T ≫ [Cr(VI)]T at 30 °C. The critical micellar concentrations values of the three representative surfactants, N-cetylpyridinium chloride (CPC), sodium dodecyl sulphate (SDS), and TX-100, are determined by conductometric and spectrophotometric methods. The oxidized product glyceraldehyde is identified by 2,4-DNP test and FTIR spectral measurement. The pseudo-first-order rate constants (k obs, s−1) are calculated from the slope of plots of ln(A 450) versus time (t) which are linear. From these plots, the kinetic parameter k eff values are calculated and the k eff value of SDS-catalyzed bipy-promoted reaction path was found to be highest among all the combinations. In the bipy-promoted oxidation path, Cr(VI)–bipy complex is the main active oxidant which undergoes attack by the substrate to form the product. The active oxidant Cr(VI)–bipy complex reacts with glycerol to form a ternary complex which undergoes redox decomposition in a rate-limiting step. Here, the anionic surfactant SDS and the neutral surfactant TX-100 both catalyze the reaction in the presence of bipy, whereas the cationic surfactant CPC and neutral surfactant TX-100 inhibit the reaction in the absence of bipy. SDS is found to be the most suitable micellar catalyst for the bipy-promoted chromic acid oxidation of glycerol.

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Acknowledgments

Thanks to UGC, New Delhi and CSIR, New Delhi for providing financial help in the form of project and fellowship.

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Authors and Affiliations

  1. Homogeneous Catalysis Laboratory, Department of Chemistry, The University of Burdwan, Golapbag, Burdwan, 713104, WB, India

    Aniruddha Ghosh, Rumpa Saha, Kakali Mukherjee, Sumanta K. Ghosh, Pintu Sar, Susanta Malik & Bidyut Saha

  2. Bishnupur K.G. Engineering Institute, Bankura, WB, India

    Rumpa Saha

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  1. Aniruddha Ghosh
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Ghosh, A., Saha, R., Mukherjee, K. et al. Choice of suitable micellar catalyst for 2,2′-bipyridine-promoted chromic acid oxidation of glycerol to glyceraldehyde in aqueous media at room temperature. Res Chem Intermed 41, 3057–3078 (2015). https://doi.org/10.1007/s11164-013-1415-6

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