Hydrolysis of ethyl-2-bromoisobutyrate ester in an alkaline solution

The hydrolysis of ethyl-2-bromoisobutyrate in an alkaline solution/organic solvent two-phase medium as well as the effect of quaternary ammonium salt (e.g., tetrabutylammonium bromide) on the hydrolysis of ethyl-2-bromoisobutyrate were investigated in this work. The proposed mechanism for the hydrolysis of ethyl-2-bromoisobutyrate was verified based on experimental analysis. Both the bromo-alkyl (Br-C bond) and ester (-COOR) functional groups of ethyl-2-bromo-isobutyrate hydrolyze into alcohol and acid. Several reaction steps for the hydrolysis of these bromo-alkyl and ester functional groups were developed and discussed. A kinetic model of each reaction step was developed in which the rate expression was derived. The intrinsic rate constants of the reactions were determined from the experimental hydrolyzing data of ethyl-2-bromoisobutyrate using curving fitting. The effects of the reaction conditions on the conversion of reactants were investigated in detail. The results indicated that the conversion of reactants is highly dependent on the concentration of alkaline compound in the aqueous solution. An optimum value of alkaline concentration to produce a maximum conversion of reactant was obtained. Moreover, the conditions for reducing the hydrolysis of halo ester by adding sodium carbonate are recommended.