Removal of 1,4-Naphthoquinone by Birnessite-Catalyzed Oxidation: Effect of Phenolic Mediators and the Reaction Pathway

Han-Saem Lee, Jin Hur, Doo-Hee Lee, Mark A. Schlautman and Hyun-Sang Shin
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Han-Saem Lee: Department of Environment Energy Engineering, Seoul National University of Science & Technology, Seoul 01811, Korea
Jin Hur: Department of Environment & Energy, Sejong University, Seoul 05006, Korea
Doo-Hee Lee: Mass Spectrometer Laboratory, National Instrumentation Center for Environmental Management, Seoul 08826, Korea
Mark A. Schlautman: Department of Environmental Engineering and Earth Science, Clemson University, Clemson, SA 29634, USA
Hyun-Sang Shin: Department of Environment Energy Engineering, Seoul National University of Science & Technology, Seoul 01811, Korea

IJERPH, 2020, vol. 17, issue 13, 1-15

Abstract: This study investigated the birnessite ( δ -MnO 2 ) catalyzed oxidative removal of 1,4-naphthoquinone (1,4-NPQ) in the presence of phenolic mediators; specifically, the kinetics of 1,4-NPQ removal under various conditions was examined, and the reaction pathway of 1,4-NPQ was verified by liquid chromatography–tandem mass spectrometry (LC–MS/MS). The removal rate of 1,4-NPQ by birnessite-catalyzed oxidation (pH = 5) was faster in the presence of phenolic mediators with electron-donating substituents (pseudo-first-order initial stage rate constant ( k 1 ) = 0.380–0.733 h −1 ) than with electron-withdrawing substituents ( k 1 = 0.071–0.244 h −1 ), and the effect on the substituents showed a positive correlation with the Hammett constant (Σσ) ( r 2 = 0.85, p < 0.001). The rate constants obtained using variable birnessite loadings (0.1–1.0 g L −1 ), catechol concentrations (0.1–1.0 mM), and reaction sequences indicate that phenolic mediators are the major limiting factor for the cross-coupling reaction of 1,4-NPQ in the initial reaction stages, whereas the birnessite-catalyzed surface reaction acts as the major limiting factor in the later reaction stages. This was explained by the operation of two different reaction mechanisms and reaction products identified by LC-MS/MS.

Keywords: 1,4-naphthoquinone; birnessite; phenolic mediator; cross-coupling; kinetics; pathway (search for similar items in EconPapers)
JEL-codes: I I1 I3 Q Q5 (search for similar items in EconPapers)
Date: 2020
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