Answer to Question #146562 in Organic Chemistry for Nina Jansen

Question

For my project I need to know how the hydrolysis of the test item BADGE goes. The first hydrolysis product is BADGE-H2O and the second hydrolysis product is BADGE-2H2O. I only could find hydrolysis of BADGE with OH- or with H+, but my medium is water, so neither acidic or basic, I think. So my question is; how does the hydrolysis go in water and which mechanism is it?

Answer 1

BADGE when mixed with water, hydrolyzes to form BADGE·H2O.

BADGE hydrolysis is modeled as a function of pH (2–12) and temperature (15–40 °C).

BADGE half-lives at pH 7 and 15, 25, 35, and 40 °C were 11, 4.6, 2.0, and 1.4 days.

At 25 °C and pH 2–12, bisphenol F diglycidyl ether hydrolyzes in a similar way to BADGE.

BADGE-2H2O is the final end product of BADGE·H2O hydrolysis and is relatively stable. This reaction happens under alkaline conditions. It is also noticed that the cconcentration of the product increases steadily with reaction time.