TY - JOUR
T1 - Oxidative transformation kinetics and pathways of albendazole from reactions with manganese dioxide
AU - Liou, Sin Yi
AU - Chen, Wan Ru
N1 - Funding Information:
This work is supported by Taiwan Ministry of Science and Technology . ( # MOST 104-2815-C-006-087-E and MOST 105-2221-E-006-007-MY3 ).
Funding Information:
This work is supported by Taiwan Ministry of Science and Technology. (# MOST 104-2815-C-006-087-E and MOST 105-2221-E-006-007-MY3).
Publisher Copyright:
© 2017 Elsevier B.V.
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.
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U2 - 10.1016/j.jhazmat.2017.12.067
DO - 10.1016/j.jhazmat.2017.12.067
M3 - Article
C2 - 29329012
AN - SCOPUS:85042945705
SN - 0304-3894
VL - 347
SP - 299
EP - 306
JO - Journal of Hazardous Materials
JF - Journal of Hazardous Materials
ER -