Ozonation of aromatic monomer compounds in water: factors determining reaction outcomes

doi:10.1007/s11783-023-1654-8

Front. Environ. Sci. Eng.

2023, Vol. 17

Issue (5) : 54 https://doi.org/10.1007/s11783-023-1654-8

RESEARCH ARTICLE

Ozonation of aromatic monomer compounds in water: factors determining reaction outcomes

Zhe Wang¹, Wenjuan Zhang², Zhiwei Wang³, Jing Chang²(

)

¹. School of Environmental Science and Safety Engineering, Tianjin University of Technology, Tianjin 300384, China
². School of Environmental and Municipal Engineering, Tianjin Key Laboratory of Aquatic Science and Technology, Tianjin Chengjian University, Tianjin 300384, China
³. Tianjin Municipal Engineering Design & Research Institute Co., Ltd., Tianjin 300384, China

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Abstract

● p- CNB and IBP were selected, to explore factors determining ozonation outcomes.

● •OH contributed only 50 % to IBP removal, compared to the 90 % for p -CNB removal.

● IBP achieved fewer TOC removal and more by-product types and quantities.

● A longer ring-opening distance existed during the degradation of IBP.

● Multiple positions on both branches of IBP were attacked, consuming more oxidants.

For aromatic monomer compounds (AMCs), ozonation outcomes were usually predicted by the substituents of the benzene ring based on the electron inductive effect. However, the predicted results were occasionally unreliable for complex substituents, and other factors caused concern. In this study, p-chloronitrobenzene (p-CNB) and ibuprofen (IBP) were selected for ozonation. According to the electron inductive theory, p-CNB should be less oxidizable, but the opposite was true. The higher rates of p-CNB were due to various sources of assistance. First, the hydroxyl radical (•OH) contributed 90 % to p-CNB removal at pH 7.0, while its contribution to IBP removal was 50 %. Other contributions came from molecular O₃ oxidation. Second, p-CNB achieved 40 % of the total organic carbon (TOC) removal and fewer by-product types and quantities, when compared to the results for IBP. Third, the oxidation of p-CNB started with hydroxyl substitution reactions on the benzene ring; then, the ring opened. However, IBP was initially oxidized mainly on the butane branched chain, with a chain-shortening process occurring before the ring opened. Finally, the degradation pathway of p-CNB was single and consumed fewer oxidants. However, both branches of IBP were attacked simultaneously, and three degradation pathways that relied on more oxidants were proposed. All of these factors were determinants of the rapid removal of p-CNB.

Keywords Ozonation Aromatic compound Oxidizing specie By-product Initial reaction position Degradation pathway

Corresponding Author(s): Jing Chang

Issue Date: 28 November 2022

Cite this article:

Zhe Wang,Wenjuan Zhang,Zhiwei Wang, et al. Ozonation of aromatic monomer compounds in water: factors determining reaction outcomes[J]. Front. Environ. Sci. Eng., 2023, 17(5): 54.

URL:

https://academic.hep.com.cn/fese/EN/10.1007/s11783-023-1654-8
https://academic.hep.com.cn/fese/EN/Y2023/V17/I5/54

Fig.1 (a) Ozonation of the IBP and p-CNB at various target concentrations, and (b) the results of ASA, p-CBA, and SA ozonation. Conditions: [O₃]₀ = 0.5 mg/L, pH = 7.0, T = 20 °C, [ASA]₀ = [p-CBA]₀ = [SA]₀ =10.8 µmol/L.

Fig.2 (a) Ozonation of IBP and p-CNB under various initial dissolved O₃ concentrations, (b) Changes of the residual O₃ concentration in pure water. Conditions: [AMCs]₀ = 10.8 µmg/L, pH = 7.0, T = 20 °C.

Fig.3 (a) Effects of initial pH values on the removal of IBP, (b) p-CNB, (c) k_obs changes. Conditions: [AMCs]₀ = 10.8 µmol/L, [O₃]₀ = 0.5 mg/L, T = 20 °C.

Fig.4 (a) Effects of TBA addition on the target removal at pH 7.0, (b) contributions of each oxidizing species to the target removal at various pH values. Conditions: [AMCs]₀ = 10.8 µmol/L, [O₃]₀ = 0.5 mg/L, [TBA]₀ = 2500 µmol/L, T = 20 °C.

Tab.1 Effects of TBA addition on the k_obs (min^–1) of ozonation at different initial pH values. Conditions: [AMCs]₀ = 10.8 µmol/L, [O₃]₀ = 0.5 mg/L, [TBA]₀ = 2500 µmol/L, T = 20 °C

Fig.5 TOC changes during the ozonation of IBP and p-CNB. Conditions: [AMCs]₀ = 54.0 µmol/L, [O₃]₀ = 0.5 mg/L, pH =5.0, T = 20 °C.

Tab.2 Ozonation by-products of IBP and p-CNB containing ?OH/?COOH groups. Conditions: [AMCs]₀ = 54.0 µmol/L, [O₃]₀ = 0.5 mg/L, pH =5.0, T = 20 °C

Fig.6 (a) Transformation treads of by-products from the ozonation of p-CNB, (b and c) IBP. Conditions: [AMCs]₀ = 54.0 µmol/L, [O₃]₀ = 0.5 mg/L, pH =5.0, T = 20 °C.

Fig.7 Optimized molecular structures and results of quantum computing for the p-CNB and IBP.

Fig.8 Reaction pathways of p-CNB and IBP during ozonation.

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