Kinetics and mechanisms of the formation of chlorinated and oxygenated polycyclic aromatic hydrocarbons during chlorination

Xu, Xiong; Xiao, Ruiyang; Dionysiou, Dionysios D.; Spinney, Richard; Fu, Thomas C.; Li, Qiang; Wang, Zijian; Wang, Donghong; Wei, Zongsu

doi:10.1016/j.cej.2018.06.075

Cited by 59 publications

(20 citation statements)

References 52 publications

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“…Nevertheless, the potential harm of 6-ClBaP in foods cannot be neglected as it has exhibited aryl hydrocarbon receptor-mediated activity and DNA-damaging effects. Moreover, the contamination and toxicity might be underestimated according to a growing number of studies in the environmental sciences. − …”

Section: Resultsmentioning

confidence: 99%

Simultaneous Determination of Typical Chlorinated, Oxygenated, and European Union Priority Polycyclic Aromatic Hydrocarbons in Milk Samples and Milk Powders

Yan

Gong

et al. 2021

J. Agric. Food Chem.

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An increasing number of studies have suggested that PAH contamination in dairy products demands high concern. This study established an efficient determination method for the European Union 15 + 1 PAHs and four PAH derivatives in dairy samples using a QuEChERS method coupled with GC-QqQ-MS. The optimized method obtained a recovery of 63.38−109.17% with a precision of 3.82−15.62%, and the limit of detection and limit of quantification were 0.08−0.78 and 0.27−2.59 μg/kg, respectively. The validated method was then successfully applied to identify the 20 PAHs in 82 dairy samples, including 43 commercial milk samples and 39 milk powders. The total PAH concentrations ranged from 2.37 to 11.83 μg/kg, and benzo[a]pyrene was only quantified in one milk and one milk powder sample at 0.35 and 0.42 μg/kg, respectively. The concentrations of PAH4 in milk samples and milk powders were not quantified (nq)−3.99 and nq−4.51 μg/kg, respectively. The results confirmed the appreciable occurrence of PAHs in dairy products, especially in infant formula. The data in this study provide a scientific basis for assessment on origin tracing, dietary exposure, and health risk of PAHs and their derivatives.

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Section: Resultsmentioning

confidence: 99%

Simultaneous Determination of Typical Chlorinated, Oxygenated, and European Union Priority Polycyclic Aromatic Hydrocarbons in Milk Samples and Milk Powders

Yan

Gong

et al. 2021

J. Agric. Food Chem.

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“…For pyrene, f −1 ( r ) value of 1(3,6,8)-position is higher than 4(5,9,10)-position. 48 The detected 1-chloropyrene and 1,6,8-trichloro-pyrene were the Cl substitution results of pyrene. The degradation product of fluoranthene was detected as 5,6-dichloro-acenaphthylenone, which might be obtained by ring rupture of fluoranthene, further oxidation and Cl substitution in the HOCl oxidation process.…”

Section: Resultsmentioning

confidence: 88%

“…Subsequently, anthrone underwent another single electron transfer and was nucleophilic attacked by a second water molecule to get 9,10-anthracenedione. 48 In addition, the formation of a portion of 9,10-anthracenedione was ascribed to the oxidation effect of OH˙. 49 Proposed degradation pathways of anthracene by HOCl and OH˙ were shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Among them, Cl-PAHs have been arising wide public concern due to their dioxin-like toxicity, which can pose potential hazardous effect on human health. 48 Therefore, to realize the complete degradation (to improve the mineralization ratio) of PAHs in contaminated industrial soil is the main task in the soil remediation. Catalytic-enhanced and UV-assisted photodegradation technologies might be the effective ways that need further exploring.…”

Section: Resultsmentioning

confidence: 99%

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Remediation of PAHs contaminated industrial soils by hypochlorous acid: performance and mechanisms

Jiang

et al. 2022

RSC Adv.

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“…In this study, we explored the use of in silico modeling for identifying the most probable environmental reaction products generated during the reaction of free chlorine with a family of structurally related steroidal trienones (i.e., 17α-trenbolone, 17β-trenbolone, methyltrenbolone, gestrinone, and altrenogest), dienones (i.e., dienogest, dienedione, and methyldienolone), and enones (i.e., testosterone) (see structures in Figure S1 of the Supporting Information, SI). We focused on chlorination reactions due to the widespread use of free chlorine in chemical disinfection of water and wastewater, − the well-recognized ability of chlorination of the steroid ring structure to amplify anabolic activity, and the limited amount of existing work using computational tools to predict chlorination products from emerging pollutant classes, including aromatic hydrocarbons, various amines, and naproxen. − Although other steroid classes (e.g., estrogens and glucocorticoids) have been extensively investigated, far less is known about the reaction of free chlorine with steroidal enones. Further, based on recent work with α,β-unsaturated carbonyls, we anticipated that most of these steroidal enones would be reactive toward free chlorine under conditions representative of water treatment and distribution.…”

Section: Introductionmentioning

confidence: 99%

Computational Approaches for the Prediction of Environmental Transformation Products: Chlorination of Steroidal Enones

Knutson

Pflug

Yeung

et al. 2021

Environ. Sci. Technol.

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There is growing interest in the fate and effects of transformation products generated from emerging pollutant classes, and new tools that help predict the products most likely to form will aid in risk assessment. Here, using a family of structurally related steroids (enones, dienones, and trienones), we evaluate the use of density functional theory to help predict products from reaction with chlorine, a common chemical disinfectant. For steroidal dienones (e.g., dienogest) and trienones (e.g., 17β-trenbolone), computational data support that reactions proceed through spontaneous C4 chlorination to yield 4-chloro derivatives for trienones and, after further reaction, 9,10-epoxide structures for dienones. For testosterone, a simple steroidal enone, in silico predictions suggest that C4 chlorination is still most likely, but slow at environmentally relevant conditions. Predictions were then assessed through laboratory chlorination reactions (0.5−5 mg Cl 2 /L) with product characterization via HRMS and NMR, which confirmed near exclusive 4-chloro and 9,10-epoxide products for most trienones and all dienones, respectively. Also consistent with computational expectations, testosterone was effectively unreactive at these same chlorine levels, although products consistent with in silico predictions were observed at higher concentrations (in excess of 500 mg Cl 2 /L). Although slight deviations from in silico predictions were observed for steroids with electron-rich substituents (e.g., C17 allyl-substituted altrenogest), this work highlights the potential for computational approaches to improve our understanding of transformation products generated from emerging pollutant classes.

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Kinetics and mechanisms of the formation of chlorinated and oxygenated polycyclic aromatic hydrocarbons during chlorination

Cited by 59 publications

References 52 publications

Simultaneous Determination of Typical Chlorinated, Oxygenated, and European Union Priority Polycyclic Aromatic Hydrocarbons in Milk Samples and Milk Powders

Simultaneous Determination of Typical Chlorinated, Oxygenated, and European Union Priority Polycyclic Aromatic Hydrocarbons in Milk Samples and Milk Powders

Remediation of PAHs contaminated industrial soils by hypochlorous acid: performance and mechanisms

Computational Approaches for the Prediction of Environmental Transformation Products: Chlorination of Steroidal Enones

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