Transformation of avobenzone in conditions of aquatic chlorination and UV-irradiation

Emerging contaminants represent a wide group of the most different compounds. They appear in the environment at trace levels due to human activity. Most of these compounds are not yet regulated. Sunscreen UV-filters play an important role among these emerging contaminants. In the present research the reactions of 4-tert-butyl-4’-methoxydibenzoylmethane (avobenzone), the most common UV filter in the formulation of sunscreens, were studied under the combined influence of active chlorine and UV-irradiation. Twenty five compounds were identified by GC/MS as transformation products of avobenzone in reactions of aquatic UV-irradiation and chlorination with sodium hypochlorite. A complete scheme of transformation of avobenzone covering all the semivolatile products is proposed. The identification of the two primary chlorination products (2-chloro-1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)-1,3-propanedione and 2,2-dichloro-1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)-1,3-propanedione) was confirmed by their synthesis and GC/MS and NMR analysis. Although the toxicities of the majority of these products remain unknown substituted chlorinated phenols and acetophenones are known to be rather toxic. Combined action of active chlorine and UV-irradiation results in the formation of some products (chloroanhydrides, chlorophenols) not forming in conditions of separate application of these disinfection methods. Therefore caring for people «well-being» it is of great importance to apply the most appropriate disinfection method. Since the primary transformation products partially resist powerful UV-C irradiation they may be treated as stable and persistent pollutants. [Display omitted] •Avobenzone is a widespread emerging contaminant belonging to the class of sunscreens.•Aquatic chlorination and UV-irradiation brings to 25 semivolatile products of avobenzene.•The detected chlorinated acetophenones and phenols are well known ecotoxicants.•Toxicological properties of the majority of the by-products remain unknown.•The primary transformation products of avobenzone are quite resistant to UV light.