Transformation behavior of the ultraviolet absorbent 2-(2H-benzotriazol-2-yl)-4,6-di-tert-pentylphenol (UV328) in polyethylene plastic under chlorination

Abstract

In plastic, a 2-(2H-benzotriazol-2-yl)-4,6-di-tert-pentylphenol (UV328) ultraviolet light absorber is a common additive. When using sodium hypochlorite (NaClO) to disinfect plastic, UV328 may react with NaClO. For this work, we investigated the transformation behavior of UV328 in polyethylene (PE) plastic by NaClO. The reaction rate increased with the initial free active chlorine (OCl−) concentration and the decrease of the initial UV328 concentration. At room temperature (25 °C) to lower temperatures (0 °C), OCl− could transform UV328, and the reaction activation energy was fitted as 31.10 kJ/mol. Replacement of the plastic carrier (change to polypropylene) had no effect on the reaction process. A total of 12 intermediates were identified, and calculations based on density functional theory (DFT) were used to assist in rationalizing the product structure. Chlorination, hydroxylation, coupling, and bond cleavage were speculated as the main transformation pathways. Dichloroacetic acid (DCAA) and trichloroacetic acid (TCAA) were the only two measured disinfection by-products in the system, and their concentration were 18.33 and 18.19 μg/g, respectively. The toxicity prediction by Toxicity Estimation Software Tool (T.E.S.T) illustrated that the toxicity of the transformation products was higher overall than that of UV328 during the reaction. This work can help to deepen the understanding of the transformation behavior of UV328 in PE plastic in NaClO solution.