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Mechanism of chloroform formation by chlorine and its inhibition by chlorine dioxide.
Fundam Appl Toxicol. 1985 Apr; 5(2):305-13.FA

Abstract

Chlorination of drinking waters leads to the formation of trihalomethanes arising from the reaction of chlorine and organic substances. Therefore, chlorine dioxide (ClO2) which does not produce trihalomethanes is being considered as an alternative disinfectant. It has been reported that rat blood chloroform levels were significantly decreased after treatment with ClO2. Studies were conducted to investigate the mechanisms of chloroform formation by chlorine (HOCl) and its inhibition by ClO2 (5 mg/liter) in the presence of HOCl (5, 10, 20 mg/liter) using sodium citrate (1 mM) as an organic substance. When citrate was reacted with HOCl, beta-ketoglutaric acid, monochloroacetone, dichloroacetone, and trichloroacetone were produced as reaction intermediates and chloroform as a final product. There was a linear relationship between the concentrations of HOCl and the formation of chloroform. When ClO2 was substituted for HOCl, neither chloroform was formed nor citrate concentration was changed. Further, chloroform formation was inhibited by ClO2 in the presence of HOCl and citrate and the degree of inhibition depends on the ratio of ClO2/HOCl. Gas chromatograph/mass spectrometer analysis indicates that this inhibition is related to the reaction of ClO2 with beta-ketoglutaric acid to form malonic acid. Chlorine dioxide also oxidizes other intermediates such as monochloroacetone and dichloroacetone to acetic acid. These studies indicate that ClO2 inhibits chloroform formation from citrate and HOCl by the oxidation of the intermediates which were involved in the reaction of chloroform formation.

Authors

Suh DH
No affiliation info available
Abdel-Rahman MS
No affiliation info available

MeSH

AcetoneChemical PhenomenaChemistryChlorineChlorine CompoundsChloroformChromatography, GasCitratesCitric AcidKetoglutaric AcidsMalonatesMolecular ConformationOxidesWater Supply

Pub Type(s)

Journal Article

Language

eng

PubMed ID

3988001

Citation

Suh, D H., and M S. Abdel-Rahman. "Mechanism of Chloroform Formation By Chlorine and Its Inhibition By Chlorine Dioxide." Fundamental and Applied Toxicology : Official Journal of the Society of Toxicology, vol. 5, no. 2, 1985, pp. 305-13.
Suh DH, Abdel-Rahman MS. Mechanism of chloroform formation by chlorine and its inhibition by chlorine dioxide. Fundam Appl Toxicol. 1985;5(2):305-13.
Suh, D. H., & Abdel-Rahman, M. S. (1985). Mechanism of chloroform formation by chlorine and its inhibition by chlorine dioxide. Fundamental and Applied Toxicology : Official Journal of the Society of Toxicology, 5(2), 305-13.
Suh DH, Abdel-Rahman MS. Mechanism of Chloroform Formation By Chlorine and Its Inhibition By Chlorine Dioxide. Fundam Appl Toxicol. 1985;5(2):305-13. PubMed PMID: 3988001.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Mechanism of chloroform formation by chlorine and its inhibition by chlorine dioxide. AU - Suh,D H, AU - Abdel-Rahman,M S, PY - 1985/4/1/pubmed PY - 1985/4/1/medline PY - 1985/4/1/entrez SP - 305 EP - 13 JF - Fundamental and applied toxicology : official journal of the Society of Toxicology JO - Fundam Appl Toxicol VL - 5 IS - 2 N2 - Chlorination of drinking waters leads to the formation of trihalomethanes arising from the reaction of chlorine and organic substances. Therefore, chlorine dioxide (ClO2) which does not produce trihalomethanes is being considered as an alternative disinfectant. It has been reported that rat blood chloroform levels were significantly decreased after treatment with ClO2. Studies were conducted to investigate the mechanisms of chloroform formation by chlorine (HOCl) and its inhibition by ClO2 (5 mg/liter) in the presence of HOCl (5, 10, 20 mg/liter) using sodium citrate (1 mM) as an organic substance. When citrate was reacted with HOCl, beta-ketoglutaric acid, monochloroacetone, dichloroacetone, and trichloroacetone were produced as reaction intermediates and chloroform as a final product. There was a linear relationship between the concentrations of HOCl and the formation of chloroform. When ClO2 was substituted for HOCl, neither chloroform was formed nor citrate concentration was changed. Further, chloroform formation was inhibited by ClO2 in the presence of HOCl and citrate and the degree of inhibition depends on the ratio of ClO2/HOCl. Gas chromatograph/mass spectrometer analysis indicates that this inhibition is related to the reaction of ClO2 with beta-ketoglutaric acid to form malonic acid. Chlorine dioxide also oxidizes other intermediates such as monochloroacetone and dichloroacetone to acetic acid. These studies indicate that ClO2 inhibits chloroform formation from citrate and HOCl by the oxidation of the intermediates which were involved in the reaction of chloroform formation. SN - 0272-0590 UR - https://www.unboundmedicine.com/medline/citation/3988001/Mechanism_of_chloroform_formation_by_chlorine_and_its_inhibition_by_chlorine_dioxide_ DB - PRIME DP - Unbound Medicine ER -