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Investigation on Reaction Products From Oxidative Coupling Reactions of 1-Naphthol By Manganese Oxide  

Lim, Dong-Min (Department of Environment Engineering, Seoul National University of Technology)
Lee, Doo-Hee (Eco-Material Education Center, Department of Environmental Engineering, Seoul National University of Technology)
Kang, Ki-Hoon (Technology Research Institute, Daelim Industrial Co., Ltd.)
Shin, Hyun-Snag (Department of Environment Engineering, Seoul National University of Technology)
Publication Information
Journal of Korean Society of Environmental Engineers / v.29, no.9, 2007 , pp. 989-996 More about this Journal
Abstract
In this study, abiotic transformation of 1-naphthol(1-NP) via oxidative-coupling reaction and its reaction products were investigated in the presence of Mn oxides. The reaction products were characterized for their relative polarity using solvent extraction experiment and reverse-phase HPLC, and for structure using CCMS and LC/MS, and for absorption characteristics using UV-Vis spectrometry. The reaction products present in aqueous phase were more polar than parent naphthol and comprised of 1,4-naphthoquinon(1,4-NPQ) and oligomers such as dimers and trimers. Hydrophilic component present in water phase after solvent$(CH_2Cl_2)$ extractions was identified as naphthol polymerized products having molecular weight(m/z) ranging from 400 to 2,000, and showed similar UV-Vis. absorption characteristics to that of foil fulvic acid. Transformation of 1,4-NPQ, which is non-reactive to Mn oxide, to the polymerized products via cross-coupling reaction in the presence of 1-NP was also verified. In this experimental conditions(20.5 mg/L, 1-NP, 2.5 g/L $MnO_2$, pH 5), the transformation of 1-NP into the oligomers and polymerized products were about 83% of initial 1-NP concentrations, and more than 30% of the reaction products was estimated to be water insoluble fractions, not extracted by $H_2O$ methanol. Results from this study suggest that Mn oxide-mediated treatment of naphthol contaminated soils can achieve risk reduction through the formation of oligomers md polymer precipitation.
Keywords
1-Naphthol; Mn Oxide; Reaction Products; Oligomers; Oxidative-coupling Reaction;
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Times Cited By KSCI : 2  (Citation Analysis)
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