A review on the degradation of acetaminophen by advanced oxidation process: pathway, by-products, biotoxicity, and density functional theory calculation

Abstract

Water scarcity and the accumulation of recalcitrance compounds into the environment are the main reasons behind the attraction of researchers to use advanced oxidation processes (AOPs). Many AOP systems have been used to treat acetaminophen (ACT) from an aqueous medium, which leads to generating different kinetics, mechanisms, and by-products. In this work, state-of-the-art studies on ACT by-products and their biotoxicity, as well as proposed degradation pathways, have been collected, organized, and summarized. In addition, the Fukui function was used for predicting the most reactive sites in the ACT molecule. The most frequently detected by-products in this review were hydroquinone, 1,4-benzoquinone, 4-aminophenol, acetamide, oxalic acid, formic acid, acetic acid, 1,2,4-trihydroxy benzene, and maleic acid. Both the experimental and prediction tests revealed that N-(3,4-dihydroxy phenyl) acetamide was mutagenic. Meanwhile, N-(2,4-dihydroxy phenyl) acetamide and malonic acid were only found to be mutagenic in the prediction test. The findings of the LC₅₀ (96 h) test revealed that benzaldehyde is the most toxic ACT by-products and hydroquinone, N-(3,4-dihydroxyphenyl)formamide, 4-methylbenzene-1,2-diol, benzoquinone, 4-aminophenol, benzoic acid, 1,2,4-trihydroxybenzene, 4-nitrophenol, and 4-aminobenzene-1,2-diol considered harmful. The release of them into the environment without treatment may threaten the ecosystem. The degradation pathway based on the computational method was matched with the majority of ACT proposed pathways and with the most frequent ACT by-products. This study may contribute to enhance the degradation of ACT by AOP systems.