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Oxidation of indometacin by ferrate (VI): kinetics, degradation pathways, and toxicity assessment

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Abstract

The oxidation of indometacin (IDM) by ferrate(VI) (Fe(VI)) was investigated to determine the reaction kinetics, transformation products, and changes in toxicity. The reaction between IDM and Fe(VI) followed first-order kinetics with respect to each reactant. The apparent second-order rate constants (k app) decreased from 9.35 to 6.52 M−1 s−1, as the pH of the solution increased from 7.0 to 10.0. The pH dependence of k app might be well explained by considering the species-specific rate constants of the reactions of IDM with Fe(VI). Detailed product studies using liquid chromatography-tandem mass spectrometry (LC-MS/MS) indicated that the oxidation products were primarily derived from the hydrolysis of amide linkages, the addition of hydroxyl groups, and electrophilic oxidation. The toxicity of the oxidation products was evaluated using the Microtox test, which indicated that transformation products exhibited less toxicity to the Vibrio fischeri bacteria. Quantitative structure-activity relationship (QSAR) analysis calculated by the ecological structure activity relationship (ECOSAR) revealed that all of the identified products exhibited lower acute and chronic toxicity than the parent pharmaceutical for fish, daphnid, and green algae. Furthermore, Fe(VI) was effective in the degradation IDM in water containing carbonate ions or fulvic acid (FA), and in lake water samples; however, higher Fe(VI) dosages would be required to completely remove IDM in lake water in contrast to deionized water.

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Acknowledgments

This work is supported by the National Natural Science Foundation of China (Nos. 21377031 and 21677040) and the Innovative Team Program of High Education of Guangdong Province (2015KCXTD007). The authors would like to thank the anonymous reviewers and editors for their help in the improvement of this paper.

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Authors and Affiliations

  1. School of Environmental Science and Engineering, Guangdong University of Technology, Guangzhou Higher Education Mega Center, Panyu District, No. 100 Waihuan Xi Road, Guangzhou, 510006, People’s Republic of China

    Junlei Huang, Yahui Wang, Guoguang Liu, Ping Chen, Fengliang Wang, Jingshuai Ma & Wenying Lv

  2. School of Environmental and Chemical, Foshan University, Foshan, 528000, People’s Republic of China

    Fuhua Li

  3. School of Environment, Henan Normal University, Xinxiang, 453007, People’s Republic of China

    Haijin Liu

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  1. Junlei Huang
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Correspondence to Guoguang Liu.

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Responsible editor: Ester Heath

Highlights

• The reaction kinetics of indometacin oxidation by ferrate(VI) was investigated.

• Five different degradation products were identified by means of LC-MS/MS.

• Intermediates were observed to be less toxic than the parent compound.

• Higher ferrate(VI) dosages would be required to completely remove IDM in actual water.

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Huang, J., Wang, Y., Liu, G. et al. Oxidation of indometacin by ferrate (VI): kinetics, degradation pathways, and toxicity assessment. Environ Sci Pollut Res 24, 10786–10795 (2017). https://doi.org/10.1007/s11356-017-8750-x

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  • DOI: https://doi.org/10.1007/s11356-017-8750-x

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