Chlorination of parabens: reaction kinetics and transformation product identification
2016
Mao, Qianhui | Ji, Feng | Wang, Wei | Wang, Qiquan | Hu, Zhenhu | Yuan, Shoujun
The reactivity and fate of parabens during chlorination were investigated in this work. Chlorination kinetics of methylparaben (MeP), ethylparaben (EtP), propylparaben (PrP), and butylparaben (BuP) were studied in the pH range of 4.0 to 11.0 at 25 ± 1 °C. Apparent rate constants (k ₐₚₚ) of 9.65 × 10⁻³ M⁻⁰.⁶¹⁴·s⁻¹, 1.77 × 10⁻² M⁻¹.⁰¹⁹·s⁻¹, 2.98 × 10⁻² M⁻⁰.⁸⁵¹·s⁻¹, and 1.76 × 10⁻² M⁻⁰.⁸⁶⁰·s⁻¹ for MeP, EtP, PrP, and BuP, respectively, were obtained at pH 7.0. The rate constants depended on the solution pH, temperature, and NH₄ ⁺ concentration. The maximum k ₐₚₚ was obtained at pH 8.0, and the minimum value was obtained at pH 11.0. The reaction rate constants increased with increasing temperature. When NH₄ ⁺ was added to the solution, the reaction of parabens was inhibited due to the rapid formation of chloramines. Two main transformation products, 3-chloro-parabens and 3,5-dichloro-parabens, were identified by GC-MS and LCMS-IT-TOF, and a reaction pathway was proposed. Dichlorinated parabens accumulated in solution, which is a threat to human health and the aqueous environment.
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