Transformation of Bisphenol AF during Aqueous Chlorination: Kinetics, Mechanisms, and Influence of pH

Xu, Xiong; Liu, Quanzhen; Bai, Lu; Wang, Long; Wang, Donghong; Gao, Steven

doi:10.1021/acsestwater.0c00186

Cited by 11 publications

(3 citation statements)

References 54 publications

(147 reference statements)

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“…S19 and S46df) or a mutual-activation degradation (Fig. S47) [41]. Moreover, electrochemical amperometric i-T curves of CTd-S2 showed a negative and concentration-dependent current jump after addition of free chlorine and reasserted the reduction of free chlorine by the foreign electron of CTd-S2 (see discussions of Fig.…”

Section: Resultsmentioning

confidence: 87%

Intrinsic strain of defect sites steering chlorination reaction for water purification

Sijin,

yinqiao,

Mohan

et al. 2024

Preprint

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Carbon nanotube (CT)–based chemical technologies particular in heterogenous advanced oxidation processes (AOPs) used for water purification, have been exploited over the several decades. Many strategies of CT modification have been exploited to improve the catalytic performance in the remediation processes. However, the strain fields of intrinsic defect sites on CT steering AOPs (such as chlorination) have never been reported. Here we for the first time explored the strained defect sites steering chlorination process onto high–efficient and green abatement of 2,4–dichlorophenol. Characterizations and theory analysis unveil that the strained defect sites with the elongated sp2 hybridized C–C bond displaying the larger spin–lattice relaxation boost electronic reactivity with chlorine molecules via the initial Yeager–type adsorption. As a result, the amounts and catalogs of reactive species in our chlorination are tunable on demand, such as the ratio of high–selectivity ClO• ranging from 38.8% in pure defects–based system to 87.5% in strain dominated process, which result in generating the harmless intermediates and even deep mineralization of organic. Thus, this work highlights the vital role of the strain fields on steering chlorination reaction for greener water purification even beyond.

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Section: Resultsmentioning

confidence: 87%

Intrinsic strain of defect sites steering chlorination reaction for water purification

Sijin,

yinqiao,

Mohan

et al. 2024

Preprint

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“…The coupling reactions between phenolic compounds catalyzed by enzymes or metals have been reported. , Phenoxyl radical generation via a single electron transfer was found to be a critical intermediate for the coupling reactions. ,, Similarly, in this study, chlorine oxidation induced electron transfer from acetaminophen, resulting in the formation of acetaminophen radicals. The formed acetaminophen radicals could further react via three pathways: (1) an additional electron transfer to form NAPQI; (2) self-bonding to form self-coupling products; and (3) addition to the benzene ring of acetaminophen to form dimer radicals.…”

Section: Resultsmentioning

confidence: 99%

Formation of Larger Molecular Weight Disinfection Byproducts from Acetaminophen in Chlorine Disinfection

Zhang

Han

2022

Environ. Sci. Technol.

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Acetaminophen is widely used to treat mild to moderate pain and to reduce fever. Under the worldwide COVID-19 pandemic, this over-the-counter pain reliever and fever reducer has been drastically consumed, which makes it even more abundant than ever in municipal wastewater and drinking water sources. Chlorine is the most widely used oxidant in drinking water disinfection, and chlorination generally causes the degradation of organic compounds, including acetaminophen. In this study, a new reaction pathway in the chlorination of acetaminophen, i.e., oxidative coupling reactions via acetaminophen radicals, was investigated both experimentally and computationally. Using an ultraperformance liquid chromatograph coupled to an electrospray ionization-triple quadrupole mass spectrometer, we detected over 20 polymeric products in chlorinated acetaminophen samples, some of which have structures similar to the legacy pollutants “polychlorinated biphenyls”. Both C–C and C–O bonding products were found, and the corresponding bonding processes and kinetics were revealed by quantum chemical calculations. Based on the product confirmation and intrinsic reaction coordinate computations, a pathway for the formation of the polymeric products in the chlorination of acetaminophen was proposed. This study suggests that chlorination may cause not only degradation but also upgradation of a phenolic compound or contaminant.

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“…A number of studies have also confirmed that dermal absorption can contribute to exposure to BPA [20,21] through contact with thermal paper in which BPA is added as a printing developer [22], and especially after the use of skin and hand sanitizers containing dermal penetration enhancing chemicals [23]. Interestingly, water disinfection methods can aid in the removal of BPA from drinking water [24][25][26][27].…”

Section: Introductionmentioning

confidence: 97%

Migration of BPA from Food Packaging and Household Products on the Croatian Market

Krivohlavek

Mikulec

Budeč

et al. 2023

IJERPH

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BPA is a plasticizer for the production of polycarbonate plastics and epoxy resins and is widely used in the production of household goods, including food packaging. Free BPA is known to migrate from packaging to food, and its uptake has been associated with adverse health effect, particularly the disruption of endocrine activity. The presence and migration of BPA from plastic consumer products are subject to strict regulation in the EU. The aim of this study is to analyse the migration of BPA from different packaging items and household products sold on the Croatian market. To simulate real life exposure, we treated samples with a food simulant. The analytical performance was confirmed with the EU requirements. BPA levels were assessed in 61 samples by HPLC-FLD and the LOQ of the method was 0.005 mg kg−1 for the food simulant. These results showed that the levels of BPA that migrated to the food simulant were below LOQ and in accordance with the specific migration limit into food, which was defined as 0.05 mg kg−1 for all samples. None of the analysed products presented a health hazard. However, these regulations do not refer to products intended for children’s use, in which BPA is banned. Furthermore, regulations require testing before putting products on the market, and previous research shows that possible BPA migration occurs due to various uses, along with a cumulative effect of exposure from even very small concentrations. Therefore, for accurate BPA consumer exposure evaluation and possible health risks, a comprehensive approach is needed.

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Transformation of Bisphenol AF during Aqueous Chlorination: Kinetics, Mechanisms, and Influence of pH

Cited by 11 publications

References 54 publications

Intrinsic strain of defect sites steering chlorination reaction for water purification

Intrinsic strain of defect sites steering chlorination reaction for water purification

Formation of Larger Molecular Weight Disinfection Byproducts from Acetaminophen in Chlorine Disinfection

Migration of BPA from Food Packaging and Household Products on the Croatian Market

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