Kinetics of the hydrolysis and perhydrolysis of tetraacetylethylenediamine, a peroxide bleach activator

Hydrogen peroxide and water react with tetraacetylethylenediamine (TAED) to form consecutively triacetylethylenediamine and diacetylethylenediamine with the release of two molecules of peracetic acid or acetic acid. The effect of pH, specific buffers and temperature on the rates of hydrolysis and perhydrolysis are compared. Peracetic acid reacts with TAED very slowly. The ratio of the second-order rate constants for the reaction of TAED with hydroperoxide and peracetate anions is exceptionally large after taking into account the difference in pKa values of their conjugate acids. The relative reactivity of various nucleophiles with TAED is discussed in terms of its performance as a bleach activator.