Picolinic Acid Promoted Permanganate Oxidation of D-Mannitol in Micellar Medium

Abstract

AbstractKinetics of permanganate oxidation of D-mannitol have been investigated spectrophotometrically under pseudo-first-order conditions in aqueous acidic media at 30 °C. The spectral analysis of hydrazone derivative of the product indicates the product to be an aldehyde. The observed rate constant value was found to be relatively slow in the uncatalyzed path, which increases by the presence of four isomeric promoters: 2-picolinic acid (2-PA), 4-picolinic acid (4-PA), 2,3-dipicolinic acid (2,3-diPA) and 2,6-dipicolinic acid (2,6-diPA). The catalytic effect of sodium dodecylbenzene sulfonate (SDBS) surfactant on the permanganate oxidation of D-mannitol has been also studied in the presence of the promoters. The critical micelle concentration (CMC) of SDBS alone and in presence of D-mannitol was determined by conductometry and spectrophotometry. The aggregation and morphological changes during reaction were studied by scanning electron microscopy (SEM) and transmission electron microscopy (TEM). The variation of the reaction rates for the different promoters in the presence and absence of SDBS micellar catalyst is discussed qualitatively in the terms of partitioning nature of substrate, charge of surfactant and reactants. 2,3-diPA in association with SDBS as micellar catalyst accelerated the reaction velocity compared to the uncatalyzed path.