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Transformation of Methylparaben by aqueous permanganate in the presence of iodide: Kinetics, modeling, and formation of iodinated aromatic products.
Water Res. 2018 05 15; 135:75-84.WR

Abstract

This work investigated impacts of iodide (I-) on the transformation of the widely used phenolic preservative methylparaben (MeP) as well as 11 other phenolic compounds by potassium permanganate (KMnO4). It was found that KMnO4 showed a low reactivity towards MeP in the absence of I- with apparent second-order rate constants (kapp) ranging from 0.065 ± 0.0071 to 1.0 ± 0.1 M-1s-1 over the pH range of 5-9. The presence of I- remarkably enhanced the transformation rates of MeP by KMnO4 via the contribution of hypoiodous acid (HOI) in situ formed, which displayed several orders of magnitude higher reactivity towards MeP than KMnO4. This enhancing effect of I- was greatly influenced by solution conditions (e.g., I- or KMnO4 concentration or pH), which could be well simulated by a kinetic model involving competition reactions (i.e., KMnO4 with I-, KMnO4 with MeP, HOI with KMnO4, and HOI with MeP). Similar enhancing effect of I- on the transformation kinetics of 5 other selected phenols (i.e., p-hydroxybenzoic acid, phenol, and bromophenols) at pH 7 was also observed, but not in the cases of bisphenol A, triclosan, 4-n-nonylphenol, and cresols. This discrepancy could be well explained by the relative reactivity of KMnO4 towards phenols vs I-. Liquid chromatography-tandem mass spectrometry analysis showed that iodinated aromatic products and/or iodinated quinone-like product were generated in the cases where I- enhancing effect was observed. Evolution of iodinated aromatic products generated from MeP (10 μM) treated by KMnO4 (50-150 μM) in the presence of I- (5-15 μM) suggested that higher I- or moderate KMnO4 concentration or neutral pH promoted their formation. A similar enhancing effect of I- (1 μM) on the transformation of MeP (1 μM) by KMnO4 (12.6 μM) and formation of iodinated aromatic products were also observed in natural water. This work demonstrates an important role of I- in the transformation kinetics and product formation of phenolic compounds by KMnO4, which has great implications for future applications of KMnO4 in treatment of I--containing water.

Authors+Show Affiliations

State Key Laboratory of Urban Water Resource and Environment, School of Environment, Harbin Institute of Technology, Harbin 150090, China.State Key Laboratory of Urban Water Resource and Environment, School of Environment, Harbin Institute of Technology, Harbin 150090, China. Electronic address: jiangjinhit@126.com.School of Municipal and Environmental Engineering, Jilin Jianzhu University, Changchun 130118, China. Electronic address: psyhit@126.com.State Key Laboratory of Urban Water Resource and Environment, School of Environment, Harbin Institute of Technology, Harbin 150090, China.State Key Laboratory of Urban Water Resource and Environment, School of Environment, Harbin Institute of Technology, Harbin 150090, China.State Key Laboratory of Urban Water Resource and Environment, School of Environment, Harbin Institute of Technology, Harbin 150090, China.State Key Laboratory of Urban Water Resource and Environment, School of Environment, Harbin Institute of Technology, Harbin 150090, China.State Key Laboratory of Urban Water Resource and Environment, School of Environment, Harbin Institute of Technology, Harbin 150090, China.State Key Laboratory of Urban Water Resource and Environment, School of Environment, Harbin Institute of Technology, Harbin 150090, China.School of Civil and Environmental Engineering, Shenzhen Polytechnic, Shenzhen 518055, China.State Key Laboratory of Urban Water Resource and Environment, School of Environment, Harbin Institute of Technology, Harbin 150090, China.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

29454924

Citation

Li, Juan, et al. "Transformation of Methylparaben By Aqueous Permanganate in the Presence of Iodide: Kinetics, Modeling, and Formation of Iodinated Aromatic Products." Water Research, vol. 135, 2018, pp. 75-84.
Li J, Jiang J, Pang SY, et al. Transformation of Methylparaben by aqueous permanganate in the presence of iodide: Kinetics, modeling, and formation of iodinated aromatic products. Water Res. 2018;135:75-84.
Li, J., Jiang, J., Pang, S. Y., Zhou, Y., Gao, Y., Yang, Y., Sun, S., Liu, G., Ma, J., Jiang, C., & Wang, L. (2018). Transformation of Methylparaben by aqueous permanganate in the presence of iodide: Kinetics, modeling, and formation of iodinated aromatic products. Water Research, 135, 75-84. https://doi.org/10.1016/j.watres.2018.02.014
Li J, et al. Transformation of Methylparaben By Aqueous Permanganate in the Presence of Iodide: Kinetics, Modeling, and Formation of Iodinated Aromatic Products. Water Res. 2018 05 15;135:75-84. PubMed PMID: 29454924.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Transformation of Methylparaben by aqueous permanganate in the presence of iodide: Kinetics, modeling, and formation of iodinated aromatic products. AU - Li,Juan, AU - Jiang,Jin, AU - Pang,Su-Yan, AU - Zhou,Yang, AU - Gao,Yuan, AU - Yang,Yi, AU - Sun,Shaofang, AU - Liu,Guanqi, AU - Ma,Jun, AU - Jiang,Chengchun, AU - Wang,Lihong, Y1 - 2018/02/10/ PY - 2017/10/31/received PY - 2018/01/29/revised PY - 2018/02/06/accepted PY - 2018/2/20/pubmed PY - 2018/9/25/medline PY - 2018/2/19/entrez KW - Iodide (I(−)) KW - Iodinated aromatic products KW - MethylParaben (MeP) KW - Permanganate KW - Phenolic compounds SP - 75 EP - 84 JF - Water research JO - Water Res. VL - 135 N2 - This work investigated impacts of iodide (I-) on the transformation of the widely used phenolic preservative methylparaben (MeP) as well as 11 other phenolic compounds by potassium permanganate (KMnO4). It was found that KMnO4 showed a low reactivity towards MeP in the absence of I- with apparent second-order rate constants (kapp) ranging from 0.065 ± 0.0071 to 1.0 ± 0.1 M-1s-1 over the pH range of 5-9. The presence of I- remarkably enhanced the transformation rates of MeP by KMnO4 via the contribution of hypoiodous acid (HOI) in situ formed, which displayed several orders of magnitude higher reactivity towards MeP than KMnO4. This enhancing effect of I- was greatly influenced by solution conditions (e.g., I- or KMnO4 concentration or pH), which could be well simulated by a kinetic model involving competition reactions (i.e., KMnO4 with I-, KMnO4 with MeP, HOI with KMnO4, and HOI with MeP). Similar enhancing effect of I- on the transformation kinetics of 5 other selected phenols (i.e., p-hydroxybenzoic acid, phenol, and bromophenols) at pH 7 was also observed, but not in the cases of bisphenol A, triclosan, 4-n-nonylphenol, and cresols. This discrepancy could be well explained by the relative reactivity of KMnO4 towards phenols vs I-. Liquid chromatography-tandem mass spectrometry analysis showed that iodinated aromatic products and/or iodinated quinone-like product were generated in the cases where I- enhancing effect was observed. Evolution of iodinated aromatic products generated from MeP (10 μM) treated by KMnO4 (50-150 μM) in the presence of I- (5-15 μM) suggested that higher I- or moderate KMnO4 concentration or neutral pH promoted their formation. A similar enhancing effect of I- (1 μM) on the transformation of MeP (1 μM) by KMnO4 (12.6 μM) and formation of iodinated aromatic products were also observed in natural water. This work demonstrates an important role of I- in the transformation kinetics and product formation of phenolic compounds by KMnO4, which has great implications for future applications of KMnO4 in treatment of I--containing water. SN - 1879-2448 UR - https://www.unboundmedicine.com/medline/citation/29454924/Transformation_of_Methylparaben_by_aqueous_permanganate_in_the_presence_of_iodide:_Kinetics_modeling_and_formation_of_iodinated_aromatic_products_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0043-1354(18)30113-1 DB - PRIME DP - Unbound Medicine ER -