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Reactions of hypoiodous acid with model compounds and the formation of iodoform in absence/presence of permanganate.
Water Res. 2017 08 01; 119:126-135.WR

Abstract

The kinetics for the reactions of hypoiodous acid (HOI) with various phenols (phenol, 4-nitrophenol, 4-hydroxybenzoic acid), 3-oxopentanedioic acid (3-OPA) and flavone were investigated in the pH range of 6.0-11.0. The apparent second order rate constants for the reactions of HOI with phenolic compounds, 3-OPA, flavone and citric acid at pH 8.0 are 10-107 M-1s-1, (4.0 ± 0.3) × 103 M-1s-1, (2.5 ± 0.2) × 103 M-1s-1 and <1 M-1s-1, respectively. The effect of buffer type and concentration was investigated with acetate, phosphate and borate. All tested buffers promote the HOI reactions with phenols. The percentage of iodine incorporation for various (hydroxyl)phenolic compounds and two NOM extracts ranges from 5% to 98%, indicating that electrophilic aromatic substitution and/or electron transfer can occur. The extent of these reactions depends on the number and relative position of the hydroxyl moieties on the phenolic compounds. Iodoform formation rates increase with increasing pH and iodoform yields increase from 9% to 67% for pH 6.0-10.0 for the HOI/3-OPA reactions. In the permanganate/HOI/3-OPA and permanganate/iodide/3-OPA system at pH < 8.0, iodoform formation is elevated compared to the HOI/3-OPA system in absence of permanganate. For pH > 8.0, in presence of permanganate, iodoform formation is significantly inhibited and iodate formation enhanced, which is due to a faster permanganate-mediated HOI disproportionation to iodate compared to the iodination process. The production of reactive iodine in real waters containing iodide in contact with permanganate may lead to the formation of iodinated organic compounds.

Authors+Show Affiliations

State Key Laboratory of Urban Water Resource and Environment, Harbin Institute of Technology, Harbin 150090, China; Eawag, Swiss Federal Institute of Aquatic Science and Technology, Ueberlandstrasse 133, CH-8600 Dübendorf, Switzerland.State Key Laboratory of Urban Water Resource and Environment, Harbin Institute of Technology, Harbin 150090, China. Electronic address: majunhit@126.com.Eawag, Swiss Federal Institute of Aquatic Science and Technology, Ueberlandstrasse 133, CH-8600 Dübendorf, Switzerland; School of Architecture, Civil and Environmental Engineering (ENAC), Ecole Polytechnique Fédérale de Lausanne (EPFL), CH-1015 Lausanne, Switzerland. Electronic address: vongunten@eawag.ch.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28454008

Citation

Zhao, Xiaodan, et al. "Reactions of Hypoiodous Acid With Model Compounds and the Formation of Iodoform in Absence/presence of Permanganate." Water Research, vol. 119, 2017, pp. 126-135.
Zhao X, Ma J, von Gunten U. Reactions of hypoiodous acid with model compounds and the formation of iodoform in absence/presence of permanganate. Water Res. 2017;119:126-135.
Zhao, X., Ma, J., & von Gunten, U. (2017). Reactions of hypoiodous acid with model compounds and the formation of iodoform in absence/presence of permanganate. Water Research, 119, 126-135. https://doi.org/10.1016/j.watres.2017.04.033
Zhao X, Ma J, von Gunten U. Reactions of Hypoiodous Acid With Model Compounds and the Formation of Iodoform in Absence/presence of Permanganate. Water Res. 2017 08 1;119:126-135. PubMed PMID: 28454008.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Reactions of hypoiodous acid with model compounds and the formation of iodoform in absence/presence of permanganate. AU - Zhao,Xiaodan, AU - Ma,Jun, AU - von Gunten,Urs, Y1 - 2017/04/13/ PY - 2017/03/06/received PY - 2017/04/07/revised PY - 2017/04/10/accepted PY - 2017/4/30/pubmed PY - 2017/10/21/medline PY - 2017/4/29/entrez KW - Hypoiodous acid KW - Iodate KW - Iodide KW - Iodoform KW - Model compounds KW - Permanganate SP - 126 EP - 135 JF - Water research JO - Water Res. VL - 119 N2 - The kinetics for the reactions of hypoiodous acid (HOI) with various phenols (phenol, 4-nitrophenol, 4-hydroxybenzoic acid), 3-oxopentanedioic acid (3-OPA) and flavone were investigated in the pH range of 6.0-11.0. The apparent second order rate constants for the reactions of HOI with phenolic compounds, 3-OPA, flavone and citric acid at pH 8.0 are 10-107 M-1s-1, (4.0 ± 0.3) × 103 M-1s-1, (2.5 ± 0.2) × 103 M-1s-1 and <1 M-1s-1, respectively. The effect of buffer type and concentration was investigated with acetate, phosphate and borate. All tested buffers promote the HOI reactions with phenols. The percentage of iodine incorporation for various (hydroxyl)phenolic compounds and two NOM extracts ranges from 5% to 98%, indicating that electrophilic aromatic substitution and/or electron transfer can occur. The extent of these reactions depends on the number and relative position of the hydroxyl moieties on the phenolic compounds. Iodoform formation rates increase with increasing pH and iodoform yields increase from 9% to 67% for pH 6.0-10.0 for the HOI/3-OPA reactions. In the permanganate/HOI/3-OPA and permanganate/iodide/3-OPA system at pH < 8.0, iodoform formation is elevated compared to the HOI/3-OPA system in absence of permanganate. For pH > 8.0, in presence of permanganate, iodoform formation is significantly inhibited and iodate formation enhanced, which is due to a faster permanganate-mediated HOI disproportionation to iodate compared to the iodination process. The production of reactive iodine in real waters containing iodide in contact with permanganate may lead to the formation of iodinated organic compounds. SN - 1879-2448 UR - https://www.unboundmedicine.com/medline/citation/28454008/Reactions_of_hypoiodous_acid_with_model_compounds_and_the_formation_of_iodoform_in_absence/presence_of_permanganate_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0043-1354(17)30296-8 DB - PRIME DP - Unbound Medicine ER -