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Transformation of 4-tert-octylphenol by UV Irradiation and by an H2O2/UV Process in Aqueous Solution

Transformation of 4-tert-octylphenol by UV Irradiation and by an H2O2/UV Process in Aqueous Solution

Patrick Mazellier, Julie Leverd

Photochem Photobiol Sci. 2003 Sep;2(9):946-53.

PMID: 14560813

Abstract:

The transformation of the organic pollutant 4-(1,1,3,3-tetramethylbutyl)phenol (4-tert-octylphenol; OP) upon irradiation at 253.7 nm and by hydroxyl radicals generated by the photolysis (lambda(exc) = 253.7 nm) of hydrogen peroxide in aqueous solution has been studied. The quantum yield of direct OP photolysis in pure aqueous solution was evaluated to be 0.058 +/- 0.004 in aerated conditions ([O2] = 272 microM). The rate of photoreaction depends on oxygen concentration; it increases with increasing [O2]. 4-tert-Octylcatechol has been identified as one of the degradation products, together with a dimeric structure. The probable mechanism of OP photolysis involves photoejection of an electron from the singlet state, leading to the formation of the 4-tert-octylphenoxyl radical. In the presence of hydrogen peroxide, the degradation of octylphenol by hydroxyl radicals has been observed. The second-order rate constant was found to be (6.4 +/- 0.5) x 10(9) M(-1) s(-1) by direct measurement at various high concentrations of hydrogen peroxide and competitive kinetic measurements using atrazine as the competitor. The degradation products are 4-tert-octylcatechol, again, and 2-hydroxy-5-tert-octylbenzoquinone. The later product may arise from the oxidation of 4-tert-octylcatechol by hydrogen peroxide or from a subsequent reaction of hydroxyl radicals with 4-tert-octylcatechol. Kinetic modelling when using either purified water or natural water successfully simulated the elimination of 4-tert-octylphenol by UV and H2O2/UV processes.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP140669-A	4-tert-Octylphenol solution, 10 μg/mL in acetone		140-66-9	Price

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