title: Degradation of phenazone in aqueous solution with ozone: influencing factors and degradation pathways.
abstract: Oxidation kinetics and degradation pathways of phenazone (an analgesic and antipyretic drug) upon reaction with O3 were investigated. Kinetic studies on degradation of phenazone were carried out under different operating conditions such as temperature, pH, anions and H2O2 addition. Results showed that the degradation followed the pseudo-first-order kinetic model. The reaction rate constant (kobs) of phenazone reached the maximum at 20 °C (9.653×10(-3) s(-1)). The presence of NO3(-) could enhance the degradation rate, while the addition of HCO3(-), SO4(2)(-), Cl(-) and the rise of pH showed negative effects on the ozonation of phenazone. H2O2 addition increased the phenazone degradation efficiency by 45.9% with the optimal concentration of 0.135 mM. Reaction by-products were evaluated by UPLC-Q-TOF-MS, which allowed the identification of a total of 10 by-products. The transformation pathways of phenazone ozonation consisted mainly of electrophilic addition and substitution, pyrazole ring opening, hydroxylation, dephenylization and coupling. The toxicity of these intermediate products showed that they are expected not to be more toxic than phenazone, with the exception of P7 (aniline) and P10 (1,5-dimethyl-4-((1-methyl-2-phenylhydrazinyl)methoxy)-2-phenyl-1H-pyrazol-3(2H)-one).
authors.affiliation: School of Environment and Civil Engineering, Jiangnan University, Wuxi 214122, PR China.
authors.forename: Heng-Feng
authors.initials: HF
authors.lastname: Miao
authors.affiliation: School of Environment and Civil Engineering, Jiangnan University, Wuxi 214122, PR China.
authors.forename: Meng
authors.initials: M
authors.lastname: Cao
authors.affiliation: School of Environment and Civil Engineering, Jiangnan University, Wuxi 214122, PR China.
authors.forename: Dan-Yao
authors.initials: DY
authors.lastname: Xu
authors.affiliation: School of Environment and Civil Engineering, Jiangnan University, Wuxi 214122, PR China.
authors.forename: Hong-Yan
authors.initials: HY
authors.lastname: Ren
authors.affiliation: School of Environment and Civil Engineering, Jiangnan University, Wuxi 214122, PR China.
authors.forename: Ming-Xing
authors.initials: MX
authors.lastname: Zhao
authors.affiliation: School of Environment and Civil Engineering, Jiangnan University, Wuxi 214122, PR China.
authors.forename: Zhen-Xing
authors.initials: ZX
authors.lastname: Huang
authors.affiliation: School of Environment and Civil Engineering, Jiangnan University, Wuxi 214122, PR China. Electronic address: wqruanjn@gmail.com.
authors.forename: Wen-Quan
authors.initials: WQ
authors.lastname: Ruan
mesh_terms: D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry*; D000983:Antipyrine / Q000737:chemistry*; D060766:Drinking Water; D006861:Hydrogen Peroxide / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D009566:Nitrates / Q000737:chemistry; D016877:Oxidants / Q000737:chemistry*; D010084:Oxidation-Reduction; D010126:Ozone / Q000737:chemistry*; D012996:Solutions; D013696:Temperature; D014874:Water Pollutants, Chemical / Q000737:chemistry*; D018508:Water Purification
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D060766:Drinking Water; D009566:Nitrates; D016877:Oxidants; D012996:Solutions; D014874:Water Pollutants, Chemical; D010126:Ozone; D006861:Hydrogen Peroxide; D000983:Antipyrine
keywords: Degradation pathway; Kinetics; Ozonation; Phenazone; Toxicity