The transformation mechanism and eco-toxicity evaluation of butylated hydroxyanisole in environment

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The transformation mechanism and eco-toxicity evaluation of butylated hydroxyanisole in environment. / Wang, Yan; Li, Xiang; Sun, Xiaomin.

In: Ecotoxicology and Environmental Safety, Vol. 231, 113179, 02.2022.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Wang, Y, Li, X & Sun, X 2022, 'The transformation mechanism and eco-toxicity evaluation of butylated hydroxyanisole in environment', Ecotoxicology and Environmental Safety, vol. 231, 113179. https://doi.org/10.1016/j.ecoenv.2022.113179

APA

Wang, Y., Li, X., & Sun, X. (2022). The transformation mechanism and eco-toxicity evaluation of butylated hydroxyanisole in environment. Ecotoxicology and Environmental Safety, 231, [113179]. https://doi.org/10.1016/j.ecoenv.2022.113179

Vancouver

Wang Y, Li X, Sun X. The transformation mechanism and eco-toxicity evaluation of butylated hydroxyanisole in environment. Ecotoxicology and Environmental Safety. 2022 Feb;231. 113179. https://doi.org/10.1016/j.ecoenv.2022.113179

Author

Wang, Yan ; Li, Xiang ; Sun, Xiaomin. / The transformation mechanism and eco-toxicity evaluation of butylated hydroxyanisole in environment. In: Ecotoxicology and Environmental Safety. 2022 ; Vol. 231.

Bibtex

@article{8ea92fefaa7d4ab796b52bb6fef1f783,
title = "The transformation mechanism and eco-toxicity evaluation of butylated hydroxyanisole in environment",
abstract = "Butylated hydroxyanisole (BHA) is one of important phenolic antioxidants and its fate in the environment has attracted much attention in recent years. In this study, the initial reactions of BHA with OH radicals, including 8 abstraction reactions and 6 addition reactions, were calculated. The lowest energy barrier of 3.20 kcal mol−1 was found from the abstraction reaction on phenolic hydroxyl group. The reaction barriers of addition paths are in the range of 5.48–9.28 kcal mol−1, which are lower than those of the abstraction paths. The reaction rate constants were calculated by using transition state theory, and the rate constants are 8.12 × 107 M−1 s−1 and 4.76 × 107 M−1 s−1 for the H-abstraction and OH-addition reactions, respectively. Through the calculation of the subsequent reactions of the abs-H0-TS1 and add-C4-M1 it was found that BHA would be further transformed into 2-tert-Butyl-1,4-benzoquinone (TBQ), tert-butylhydroquinone (TBHQ) etc. in the aqueous phase, and the eco-toxicities of these transformed products of BHA in the aqueous phase were significantly increased comparing with that of the BHA and they are toxic to aquatic organism.",
keywords = "BHA, Eco-toxicity evaluation, OH radicals, Transformation mechanism",
author = "Yan Wang and Xiang Li and Xiaomin Sun",
note = "Publisher Copyright: {\textcopyright} 2022",
year = "2022",
month = feb,
doi = "10.1016/j.ecoenv.2022.113179",
language = "English",
volume = "231",
journal = "Ecotoxicology and Environmental Safety",
issn = "0147-6513",
publisher = "Academic Press",

}

RIS

TY - JOUR

T1 - The transformation mechanism and eco-toxicity evaluation of butylated hydroxyanisole in environment

AU - Wang, Yan

AU - Li, Xiang

AU - Sun, Xiaomin

N1 - Publisher Copyright: © 2022

PY - 2022/2

Y1 - 2022/2

N2 - Butylated hydroxyanisole (BHA) is one of important phenolic antioxidants and its fate in the environment has attracted much attention in recent years. In this study, the initial reactions of BHA with OH radicals, including 8 abstraction reactions and 6 addition reactions, were calculated. The lowest energy barrier of 3.20 kcal mol−1 was found from the abstraction reaction on phenolic hydroxyl group. The reaction barriers of addition paths are in the range of 5.48–9.28 kcal mol−1, which are lower than those of the abstraction paths. The reaction rate constants were calculated by using transition state theory, and the rate constants are 8.12 × 107 M−1 s−1 and 4.76 × 107 M−1 s−1 for the H-abstraction and OH-addition reactions, respectively. Through the calculation of the subsequent reactions of the abs-H0-TS1 and add-C4-M1 it was found that BHA would be further transformed into 2-tert-Butyl-1,4-benzoquinone (TBQ), tert-butylhydroquinone (TBHQ) etc. in the aqueous phase, and the eco-toxicities of these transformed products of BHA in the aqueous phase were significantly increased comparing with that of the BHA and they are toxic to aquatic organism.

AB - Butylated hydroxyanisole (BHA) is one of important phenolic antioxidants and its fate in the environment has attracted much attention in recent years. In this study, the initial reactions of BHA with OH radicals, including 8 abstraction reactions and 6 addition reactions, were calculated. The lowest energy barrier of 3.20 kcal mol−1 was found from the abstraction reaction on phenolic hydroxyl group. The reaction barriers of addition paths are in the range of 5.48–9.28 kcal mol−1, which are lower than those of the abstraction paths. The reaction rate constants were calculated by using transition state theory, and the rate constants are 8.12 × 107 M−1 s−1 and 4.76 × 107 M−1 s−1 for the H-abstraction and OH-addition reactions, respectively. Through the calculation of the subsequent reactions of the abs-H0-TS1 and add-C4-M1 it was found that BHA would be further transformed into 2-tert-Butyl-1,4-benzoquinone (TBQ), tert-butylhydroquinone (TBHQ) etc. in the aqueous phase, and the eco-toxicities of these transformed products of BHA in the aqueous phase were significantly increased comparing with that of the BHA and they are toxic to aquatic organism.

KW - BHA

KW - Eco-toxicity evaluation

KW - OH radicals

KW - Transformation mechanism

U2 - 10.1016/j.ecoenv.2022.113179

DO - 10.1016/j.ecoenv.2022.113179

M3 - Journal article

C2 - 35026586

AN - SCOPUS:85122617579

VL - 231

JO - Ecotoxicology and Environmental Safety

JF - Ecotoxicology and Environmental Safety

SN - 0147-6513

M1 - 113179

ER -

ID: 305116972