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

Abstract

Kinetics 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.

Insights into the micellar catalysed efficient oxidation of 2- and 3-pentanol by cerium(iv) in a greener medium of SDS and STS

“…8,9 There have been various studies on the oxidation of alcohols using various transition metal oxidants such as Cu(III), 10 Ag(III), 11 Cr(VI), 12,13 V(V), 14 and Mn(VII). 15 In this research, we considered two isomeric alcohols (2-pentanol and 3-pentanol), which differ in symmetry, i.e., 2-pentanol is chiral and 3-pentanol is achiral, to explore the micellar catalysed organic transition. Inner transition metal Ce(IV) was considered as an oxidizing agent of choice in this work since it is less toxic than hexavalent chromium.…”

An efficient mixed micellar strategy for the catalytic oxidation of benzyl alcohol by diperiodatoargentate(iii) in aqueous media

“…[13][14][15][16] Recently our group has also reported the oxidation reactions of several organic substrates in mixed micellar media. [17][18][19][20] In this context, transition metal ions such as Ag(III), 21 Cu(III), 22,23 and Ni(IV) 24 are generally less used in oxidation studies compared to other higher valent transition metal ions like Cr(VI), 25,26 Mn(VII), 27,28 V(V), 29 Ce(IV), 30 Fe(III), 31 or Co(III). 32 The former transition metal ions are stabilised by periodate, telurate-like complexing agents which remain in multiple equilibrium.…”

Kinetics and Mechanism Studies of Oxidation of Dibromothymolsulfonphthalein Toxic Dye by Potassium Permanganate in Neutral Media with the Synthesis of 2-Bromo-6-isopropyl-3-methyl-cyclohexa-2,5-dienone

“…The kinetics and oxidation processes of pectates, 18 methyl cellulose, 19 alginates, 20 carboxymethyl cellulose, 21 chondroitin-4-sulfate 22 carbohydrates, and BTB 23 by potassium permanganate have been studied in basic solutions. However, the oxidation of methyl cellulose, 15 pectates, 24 carboxymethyl cellulose, 25 BTB, 26 N -(2-acetamido)imino diacetic acid, 27 poly(ethylene glycol), 28 2-butanol, 29 , 30 and mannitol 31 were investigated in acidic solutions. In these reactions, the pseudo-first-order plots were discovered to be reverse S-shape, and the reactions were found to proceed through free-radical intervention.…”