An Efficient and Mild Procedure for the Preparation of Aldonic Acids via Oxidation of D-Sucrose by Employing N-Bromophthalimide Oxidant and Micellar System

Abstract

Abstract The oxidation reactions of D-sucrose have been carried out with N-bromophthalimide in the presence of micellar aggregates at 45°C. The kinetics revealed first order dependence on N-bromophthalimide (NBP) and fractional order dependence on D-sucrose. Variation of mercuric acetate concentration has an insignificant effect on reaction rate. The stoichiometric ratio of NBP:D-sucrose was 1:2 and the oxidation product was aldonic acid confirmed by FeCl3–HCl test. The influence of salts on the reaction rate has also been studied. Phthalimide (NHP) and sulfuric acid (H2SO4) inhibit the rate. Thermodynamic and activation parameters have been evaluated and a mechanism consistent with the kinetic data has been proposed. Cetyltrimethylammonium bromide (CTAB) and TritonX-100 (TX-100) catalyze the reaction, while sodium dodecyl sulfate (SDS) inhibits the rate of reaction. The applicability of Berezin's model was tested to explain the observed micellar effects. The rate constants (kM) and binding constants (KS + KO) have been evaluated.