J. Heyrovský Institute of Physical Chemistry of the CAS, v.v.i., Dolejškova 2155/3, 182 23, Prague 8, Czech Republic.
National Institute of Biology, Marine Biology Station, Fornace 41, 6330 Piran, Slovenia.
J Hazard Mater. 2018 Jul 5;353:70-79. doi: 10.1016/j.jhazmat.2018.03.048. Epub 2018 Mar 27.
Ketoprofen, 2-(3-benzoylphenyl)-propionic acid, a widely used non-steroidal anti-inflammatory drug, is considered as an important water pollutant. Kinetics and mechanism of its photolytic transformation in aqueous solutions was studied experimentally and partial reaction steps were modelled by means of quantum chemistry methods. While the rate of ketoprofen photolysis was not significantly affected by its acid-base equilibrium, a marked influence of pH on the subsequent degradation reactions was observed. At pH 1.3, two oxygenated primary products were identified, that underwent fast photolysis. Deprotonated form of ketoprofen was transformed preferentially to ethylbenzophenone and further degradation proceeded substantially slower. Oxygen participated on photolytic processes both as a reactant and the triplet state quencher. The active involvement of water molecules in the reaction mechanism was investigated by comparative experiments in acetonitrile. The phototransformation mechanism proposed based on the experimental data corresponded well with the theoretical results.
酮洛芬，2-(3-苯甲酰基)丙酸，一种广泛使用的非甾体抗炎药，被认为是一种重要的水污染物质。本文通过实验研究了其在水溶液中的光解转化动力学和机制，并通过量子化学方法对部分反应步骤进行了建模。虽然酮洛芬光解的速率不受其酸碱平衡的显著影响，但 pH 值对随后的降解反应有明显的影响。在 pH 值为 1.3 时，鉴定出两种含氧的初级产物，它们经历了快速光解。酮洛芬的去质子形式优先转化为乙基二苯甲酮，进一步的降解过程明显较慢。氧作为反应物和三重态猝灭剂参与光解过程。通过在乙腈中的对比实验研究了水分子在反应机制中的积极参与。基于实验数据提出的光转化机制与理论结果非常吻合。
