Collect. Czech. Chem. Commun. 1980, 45, 720-726

Alkaline hydrolysis of pivalic esters of ethylene glycol in water-acetone solutions

Stanislav Ševčík, Miroslav Kubín and Jiří Štamberg

Institute of Macromolecular Chemistry, Czechoslovak Academy of Sciences, 162 06 Prague 6


The paper reports alkaline hydrolysis of ethylene dipivalate and 2-hydroxyethyl pivalates as compounds modelling the structural unit and crosslinking site of hydrophilic gels, i.e. copolymers of 2-hydroxyethyl methacrylate and ethylene dimethacrylate. The kinetics of hydrolysis was investigated in water-acetone solutions containing respectively 50, 75, 80, 85 and 90% by vol. (related to 20°C) of acetone at 20, 30, 40, and 50°C. It was demonstrated that, owing to steric hindrance, the preferential hydrolysis of monoester was more pronounced in the case of pivalic esters of ethylene glycol compared with acetic esters of ethylene glycol. The results are discussed in connection with the selectivity of the alkaline hydrolysis of ester bonds in "pendant" parts of structural units in hydrophylic methacrylate gels.