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Experimental and theoretical studies on the photodegradation of 2-ethylhexyl 4-methoxycinnamate in the presence of reactive oxygen and chlorine species
Central European Journal of Chemistry (2014)
  • Alicja Gackowska, University of Technology and Life Sciences in Bydgoszcz
  • Maciej Przybyłek, Nicolaus Copernicus University of Torun
  • Waldemar Studziński, University of Technology and Life Sciences in Bydgoszcz
  • Jerzy Gaca, University of Technology and Life Sciences in Bydgoszcz
Abstract
2-Ethylhexyl 4-methoxycinnamate (EHMC) is one of the most commonly used sunscreen ingredient. In this study we investigated photodegradation of EHMC in the presence of such common oxidizing and chlorinating systems as H2O2, H2O2/HCl, H2O2/UV, and H2O2/HCl/UV. Reaction products were detected by gas chromatography with a mass spectrometric detector (GC-MS). As a result of experimental studies chloro-substituted 4-methoxycinnamic acid (4-MCA), 4-methoxybenzaldehyde (4-MBA) and 4-methoxyphenol (4-MP) were identified. Experimental studies were enriched with DFT and MP2 calculations. We found that reactions of 4-MCA, 4-MBA and 4-MP with Cl2 and HOCl were in all cases thermodynamically favorable. However, reactivity indices provide a better explanation of the formation of particular chloroorganic compounds. Generally, those isomeric forms of mono- and dichlorinated compounds which exhibits the highest hardness were identified. Nucleophilicity of the chloroorganic compounds precursors were examined by means of the Fukui function.
Keywords
  • 2-ethylhexyl 4-methoxycinnamate,
  • Octyl methoxycinnamate,
  • Chlorination,
  • Sunscreen,
  • Oxidation,
  • Photodegradation,
  • Stability
Publication Date
2014
DOI
10.2478/s11532-014-0522-6
Citation Information
Alicja Gackowska, Maciej Przybyłek, Waldemar Studziński and Jerzy Gaca. "Experimental and theoretical studies on the photodegradation of 2-ethylhexyl 4-methoxycinnamate in the presence of reactive oxygen and chlorine species" Central European Journal of Chemistry Vol. 12 Iss. 5 (2014) p. 612 - 623
Available at: http://works.bepress.com/maciej-przybyek/13/