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

Highlights

● 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.

Abstract

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.

Graphical abstract

Keywords

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

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Acknowledgement

This work was supported by the Education Commission Scientific Research Project of Tianjin (Natural Science) (No. 2018KJ139).

Electronic Supplementary Material

Supplementary material is available in the online version of this article at https://doi.org/10.1007/s11783-023-1654-8 and is accessible for authorized users.

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