Stability and removal of selected avobenzone's chlorination products

Abstract

Stability studies of two avobenzone transformation products: chloro-avobenzone [2-chloro-1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)-1,3-propanedione] and dichloro-avobenzone [2,2-dichloro-1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)-1,3-propanedione] have been performed at different pHs values as well as under UV A light and compared with the stability of avobenzone, one of the mostly used UV A filter present in sunscreens. We have additionally investigated the possibility of application of TiO2 photocatalysis as a method for the removal of them. Results have shown the differences in pH stability of all three studied compounds with much slower degradation rate under neutral conditions in comparison to the acidic ones for all three studied compounds. In the case of photolytic experiment, performed under UV A light, dichloro-avobenzone exhibited the lowest UVA stability (half-life 22.4 ± 0.7 min), while avobenzone and chloro-avobenzone are much more stable and have shown quite similar degradation pattern (half-lives 126 ± 16 min and 128 ± 25 min). Under the photocatalytic conditions the less stable was dichloro-avobenzone (half-life 14.1 ± 0.6 min), while chloro-avobenzone and avobenzone were much more stable (half-lives 41 ± 3 min and 79 ± 13 min). Dichloroavobenzone is significantly more reactive than avobenzone and its monochloro-derivative. On the basis of the formation of various stable degradation products, including substituted acetophenones, benzoic acids and phenols, identified by GC-MS, the degradation pathway has been proposed.