Oxidative transformation kinetics and pathways of albendazole from reactions with manganese dioxide

Sin Yi Liou, Wan-Ru Chen

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Albendazole (ABZ) is a benzimidazole-based veterinary anthelmintic used extensively in the treatment of intestinal parasites. Due to its high hydrophobicity, ABZ tends to accumulate in soils and sediments in the environment. This study aims to investigate ABZ's possible degradation by manganese oxides. Minor effects from ionic strength and metal cations on ABZ degradation were observed. By contrast, decrease of pH greatly enhanced the reaction rate. Surface complexation between ABZ and MnO2 was indicated to be the dominant control in the reaction kinetics. Suppression by the presence of co-solvents was negatively proportional to the solvent polarities (suppression from high to low: diethyl ether ~ n-butanol > ethanol > methanol > acetonitrile). Humic acid was found to cause significant inhibition due to the reductive dissolution of MnO2. Four hydrolysis and six oxidative products were identified. ABZ and its hydrolysis products containing the propylthio side chain underwent the same oxidative transformation to form their corresponding sulfoxide compounds. Dehydrogenative coupling reaction between sulfoxide products and hydrolysis products could occur to generate dimers. All hydrolysis and oxidative products were eluted faster than ABZ in liquid chromatogram, suggesting that the spreading out of ABZ will be significantly enhanced if reacting with MnO2.

Original languageEnglish
Pages (from-to)299-306
Number of pages8
JournalJournal of Hazardous Materials
Volume347
DOIs
Publication statusPublished - 2018 Apr 5

Fingerprint

Albendazole
Manganese
Hydrolysis
manganese
sulfoxide
hydrolysis
kinetics
Kinetics
Degradation
Manganese oxide
Hydrophobicity
Ionic strength
Complexation
Acetonitrile
Butenes
degradation
Reaction kinetics
Dimers
Reaction rates
manganese oxide

All Science Journal Classification (ASJC) codes

  • Environmental Engineering
  • Environmental Chemistry
  • Waste Management and Disposal
  • Pollution
  • Health, Toxicology and Mutagenesis

Cite this

@article{b10e2271541246049499b644b9b9896f,
title = "Oxidative transformation kinetics and pathways of albendazole from reactions with manganese dioxide",
abstract = "Albendazole (ABZ) is a benzimidazole-based veterinary anthelmintic used extensively in the treatment of intestinal parasites. Due to its high hydrophobicity, ABZ tends to accumulate in soils and sediments in the environment. This study aims to investigate ABZ's possible degradation by manganese oxides. Minor effects from ionic strength and metal cations on ABZ degradation were observed. By contrast, decrease of pH greatly enhanced the reaction rate. Surface complexation between ABZ and MnO2 was indicated to be the dominant control in the reaction kinetics. Suppression by the presence of co-solvents was negatively proportional to the solvent polarities (suppression from high to low: diethyl ether ~ n-butanol > ethanol > methanol > acetonitrile). Humic acid was found to cause significant inhibition due to the reductive dissolution of MnO2. Four hydrolysis and six oxidative products were identified. ABZ and its hydrolysis products containing the propylthio side chain underwent the same oxidative transformation to form their corresponding sulfoxide compounds. Dehydrogenative coupling reaction between sulfoxide products and hydrolysis products could occur to generate dimers. All hydrolysis and oxidative products were eluted faster than ABZ in liquid chromatogram, suggesting that the spreading out of ABZ will be significantly enhanced if reacting with MnO2.",
author = "Liou, {Sin Yi} and Wan-Ru Chen",
year = "2018",
month = "4",
day = "5",
doi = "10.1016/j.jhazmat.2017.12.067",
language = "English",
volume = "347",
pages = "299--306",
journal = "Journal of Hazardous Materials",
issn = "0304-3894",
publisher = "Elsevier",

}

Oxidative transformation kinetics and pathways of albendazole from reactions with manganese dioxide. / Liou, Sin Yi; Chen, Wan-Ru.

In: Journal of Hazardous Materials, Vol. 347, 05.04.2018, p. 299-306.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Oxidative transformation kinetics and pathways of albendazole from reactions with manganese dioxide

AU - Liou, Sin Yi

AU - Chen, Wan-Ru

PY - 2018/4/5

Y1 - 2018/4/5

N2 - Albendazole (ABZ) is a benzimidazole-based veterinary anthelmintic used extensively in the treatment of intestinal parasites. Due to its high hydrophobicity, ABZ tends to accumulate in soils and sediments in the environment. This study aims to investigate ABZ's possible degradation by manganese oxides. Minor effects from ionic strength and metal cations on ABZ degradation were observed. By contrast, decrease of pH greatly enhanced the reaction rate. Surface complexation between ABZ and MnO2 was indicated to be the dominant control in the reaction kinetics. Suppression by the presence of co-solvents was negatively proportional to the solvent polarities (suppression from high to low: diethyl ether ~ n-butanol > ethanol > methanol > acetonitrile). Humic acid was found to cause significant inhibition due to the reductive dissolution of MnO2. Four hydrolysis and six oxidative products were identified. ABZ and its hydrolysis products containing the propylthio side chain underwent the same oxidative transformation to form their corresponding sulfoxide compounds. Dehydrogenative coupling reaction between sulfoxide products and hydrolysis products could occur to generate dimers. All hydrolysis and oxidative products were eluted faster than ABZ in liquid chromatogram, suggesting that the spreading out of ABZ will be significantly enhanced if reacting with MnO2.

AB - Albendazole (ABZ) is a benzimidazole-based veterinary anthelmintic used extensively in the treatment of intestinal parasites. Due to its high hydrophobicity, ABZ tends to accumulate in soils and sediments in the environment. This study aims to investigate ABZ's possible degradation by manganese oxides. Minor effects from ionic strength and metal cations on ABZ degradation were observed. By contrast, decrease of pH greatly enhanced the reaction rate. Surface complexation between ABZ and MnO2 was indicated to be the dominant control in the reaction kinetics. Suppression by the presence of co-solvents was negatively proportional to the solvent polarities (suppression from high to low: diethyl ether ~ n-butanol > ethanol > methanol > acetonitrile). Humic acid was found to cause significant inhibition due to the reductive dissolution of MnO2. Four hydrolysis and six oxidative products were identified. ABZ and its hydrolysis products containing the propylthio side chain underwent the same oxidative transformation to form their corresponding sulfoxide compounds. Dehydrogenative coupling reaction between sulfoxide products and hydrolysis products could occur to generate dimers. All hydrolysis and oxidative products were eluted faster than ABZ in liquid chromatogram, suggesting that the spreading out of ABZ will be significantly enhanced if reacting with MnO2.

UR - http://www.scopus.com/inward/record.url?scp=85042945705&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85042945705&partnerID=8YFLogxK

U2 - 10.1016/j.jhazmat.2017.12.067

DO - 10.1016/j.jhazmat.2017.12.067

M3 - Article

C2 - 29329012

AN - SCOPUS:85042945705

VL - 347

SP - 299

EP - 306

JO - Journal of Hazardous Materials

JF - Journal of Hazardous Materials

SN - 0304-3894

ER -