A chromatography-mass spectrometry study of aquatic chlorination of UV-filter avobenzone
- Authors: Kalister K.1, Dolenc D.2, Sarakha M.3, Polyakova O.V.4, Lebedev A.T.4, Trebše P.5
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Affiliations:
- Laboratory for Environmental Research
- Faculty of Chemistry and Chemical technology
- Clermont Universite, Universite Blaise Pascal, Institut de Chimie de Clermont-Ferrand, Equipe Photochimie
- Department of Chemistry
- Faculty of Health Sciences
- Issue: Vol 71, No 14 (2016)
- Pages: 1289-1293
- Section: Articles
- URL: https://journals.rcsi.science/1061-9348/article/view/182230
- DOI: https://doi.org/10.1134/S1061934816140057
- ID: 182230
Cite item
Abstract
We studied the reactions of 4-tert-butyl-4′-methoxydibenzoylmethane (avobenzone), the most common UV filter in formulations of sunscreens, under the conditions of disinfection. Three chlorinated compounds were identified as the main products. Their structures were confirmed by high-performance liquid chromatography-tandem mass spectrometry (HPLC–MS2) with accurate mass measurements and by gas chromatography–mass spectrometry (GC/MS). It was reliably proved, that the substitution involved the double bond of the enolic form of the diketone, rather than the activated aromatic ring, leading to the formation of 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 as the main products. The third identified product was 2-chloro-1-(4-methoxyphenyl)ethanone.
Keywords
About the authors
K. Kalister
Laboratory for Environmental Research
Email: polonca.trebse@zf.uni-lj.si
Slovenia, Nova Gorica, 5000
D. Dolenc
Faculty of Chemistry and Chemical technology
Email: polonca.trebse@zf.uni-lj.si
Slovenia, Ljubljana, 1000
M. Sarakha
Clermont Universite, Universite Blaise Pascal, Institut de Chimie de Clermont-Ferrand, Equipe Photochimie
Email: polonca.trebse@zf.uni-lj.si
France, Clermont-Ferrand, 63000
O. V. Polyakova
Department of Chemistry
Email: polonca.trebse@zf.uni-lj.si
Russian Federation, Moscow, 119991
A. T. Lebedev
Department of Chemistry
Author for correspondence.
Email: a.lebedev@org.chem.msu.ru
Russian Federation, Moscow, 119991
P. Trebše
Faculty of Health Sciences
Author for correspondence.
Email: polonca.trebse@zf.uni-lj.si
Slovenia, Ljubljana, 1000