Transformation of 6PPDQ during disinfection: Kinetics, products, and eco-toxicity assessment

N-phenyl-N'-(1,3-dimethyl butyl)-p-phenylenediamine-quinone (6PPDQ) currently arouses broad concerns because of its acute lethality to coho salmon and rainbow trout at environmentally relevant concentrations and the wide occurrence in runoff-impacted water. Investigation on the fate and transformation of 6PPDQ in various treatment processes is necessary for its risk assessment and control. Here, we explored the transformation of 6PPDQ during disinfection with its precursor 6PPD as a reference, focusing on kinetics, products, and toxicity variation. 6PPDQ readily reacted with hypochlorite and chlorine dioxide with second-order rate constants of 2580 +/- 143 M-1 s-1 and 614 +/- 52 M-1 s-1 (pH 7.0 and 25 degrees C), which are slightly lower than the reactions of 6PPD. We tentatively identified thirteen transformation products for 6PPDQ and eight for 6PPD in reaction with the two disinfectants. It seems that the quinone ring of 6PPDQ and the p-phenylenediamine moiety of 6PPD are reactive sites. The transformation of these compounds probably proceeds through Cl-substitution, ring cleavage, hydroxylation, and amine oxidation and hydrolysis. Tests with zebrafish embryos revealed that the transformation products of 6PPDQ could have higher eco-toxicity than the parent compound, while the toxicity of the 6PPD products remained nearly unchanged. The increased toxicity of 6PPDQ during disinfection highlights the necessity to substantially reduce its content before the disinfection of runoff-impacted water.