Browse > Article
http://dx.doi.org/10.4491/KSEE.2012.34.7.445

Effect of Phenolic Mediators and Humic Acid on the Removal of 1-Indanone Using Manganese Oxide  

Choi, Chan-Kyu (Department of Energy and Environment, The Graduate School of Energy and Environment, Seoul National University of Science and Technology)
Eom, Won-Suk (Department of Environmental Engineering, Seoul National University of Science and Technology)
Shin, Hyun-Sang (Department of Environmental Engineering, Seoul National University of Science and Technology)
Publication Information
Abstract
An investigation for removal of 1-indanone (1-ID), which were commonly produced from the biological and/or chemical treatment and natural weathering of the PAHs-contaminated soils, via oxidative transformation mediated by birnessite in the presence of various phenolic mediators is described. This study also examines the potential effect of the natural occurring substance humic acid (HA) on the oxidative transformation. The experiment was carried out in aqueous phase as a batch test (10 mg/L 1-ID, 0.3 mM phenolic mediators, $1.0g/L\;{\delta}-MnO_2$, at pH 5). All of the 11 tested phenoilic mediators belong to the group of natural occurring phenols and are widely used as model constituents of humic substances. From the results of HPLC analysis, it is demonstrated that 1-ID was not reactive to birnessite itself, but it can be effectively removed in birnessite-mediated cross coupling reactions in the presence of the phenolic mediators. The percent removals of 1-ID after 2 day incubation were ranged from 9.2 to 71.2% depending on the phenolic mediators applied. The initial rate constant ($K_{int}$, $hr^{-1}$) values for the 1-ID removals obtained from the pseudo-first-order kinetic plots also widely ranged from 0.18 to 15.0. Results of the correlative analysis between the removal efficiencies and structural characteristics of phenolic mediators indicate that the transformation of the 1-ID was considerably enhanced by the addition of electron-donating substituents (e.g., -OH, $-OCH_3$) at the benzne ring, and much less enhanced by the addition of electron-withdrawing substituents (e.g., -COOH, -CHO). The presence of HA showed that removal efficiencies of 1-ID in the birnessite-phenolic mediator systems decreased with increasing HA concentrations. However at low concentration of HA (< 2 mg/L), it caused some enhancement in the removals of 1-ID as compared to the control.
Keywords
1-Indanone; Birnessite; Cross Coupling; Phenolic Mediators; Humic Acid;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
연도 인용수 순위
1 Edwards, N. T., "Polycyclic aromatic hydrocarbons (PAHs) in the terrestrial environment: a review," J. Environ. Qual., 12(4), 427-441(1983).
2 Muligan, C. N., Young, R. N. and Gibbs, B. F., "Surfactantenhanced remediation of contaminated soil: a review," Eng. Geol., 60(1-4), 371-380(2001).   DOI   ScienceOn
3 Freeman, H. M. and Harris, E. F., "Hazardous Waste Remediation. Innovative treatment technologies, Technomic Publishing Company, Lancaster, Pennsylvania, USA., (1995).
4 Eriksson, M., Dalhammar, G. and Borg-Karlsson, A. K., "Biological degradation of selected hydrocarbons in an old PAH/creosote contaminated soil from a gasworks site," Appl. Microbiol. Biotechnol., 53, 619-626(2000).   DOI
5 Lundstedt. S., "Analysis of PAHs and their transformation products in contaminated soil and remedial processes," Ph. D. thesis, Umea Univ., Sewden, (2003).
6 Ferrarese, E., Andreottola, G. and Oprea, I. A., "Remediation of PAH-contaminated sediments by chemical oxidation," J. Hazard. Mater., (2007).
7 Sehlin, E., "A study of the availability of PAHs and oxygenated PAHs in a contaminated soil," Degree Project in Chem., Umea Univ., Sweden, (2004).
8 Mallakin A., McConkey B. J, Miao G. B., McKibben B., Snieckus V., Dixon D. G. and Greenberg B. M., "Impacts of structural photomodification on the toxicity of environmental contaminants: Anthracene photooxidation products," Ecotoxicol. Environ. Saf., 43, 204-212(1999).   DOI   ScienceOn
9 Benjamin A. Musa Bandowe, Jaroslava Sobocka, Wolfgang Wilcke, "Oxygen-containing polycyclic aromatic hydrocarbons (OPAHs) in urban soils of Bratislava, Slovakia: Patterns, relation to PAHs and vertical distribution," Environ. Pollut., 159, 539-549(2011).   DOI   ScienceOn
10 Schlanges, I., Meyer, D., Palm, W. U. and Ruck, W., "Identification, quantification and distribution of PAC-metabolites, heterocyclic PAC and substituted PAC in groundwater samples of tar-contaminated sites from Germany," Polycyclic Aromatic Compounds, 28, 320-328(2008).   DOI   ScienceOn
11 Shindo, H. and Huang, P. M., "Role of Mn(IV) oxide in abiotic formation of humic substances in the environment," Nature (London), 298, 363-365(1982).   DOI
12 Bollag J. M., Myers C., Pal S. and Huang P. M., "The role of abiotic and biotic catalysts in the transformation of phenol compounds," In Envirnmental Impact of Soil Components Interactions: Natural and Anthropogenic Organics (P. M. Haung, J. Berthelin, J. M. Boallg, W. B. McGill, A. L. Pake eds.), CRC Press, Boca Raton, FL, pp. 299-310(1995).
13 Sparks, D L., "Environmental Soil Chemistry," pp. 99-139, Academic Press Inc., Califonia, USA(1995).
14 Klibanov, A. M., Tu, T. M. and Scott. K. P., "Peroxidase catalyzed removal of phenols from coal-conversion waste waters," Sci., 221, 259-26(1983).
15 Blalk, H. M., Simpson, A. J. and Pedersen, J. A., "Crosscoupling of sulfamide antimicrobial agents with model humic constituents" Environ. Sci. Technol., 39, 4463-4473(2005).   DOI   ScienceOn
16 Kang, K. H., Dec, J., Park, H., and Bollag, J.-M., "Effect of phenolic mediators and humic acid on cyprodinil transformation in presence of birnessite," Water Res., 38(11), 2737- 2745(2004).   DOI   ScienceOn
17 Leenheer, J. A.,. McKnight, D. M., Thurman, E. M. and MacCarthy, P., Humic Substances in the Suwannee River, Georgia: Interaction, Properties and Proposed Structure, US Geology Survey, Open-File Report 85-557, Denver, Colorado (1989).
18 Chang Chein, S. W., Chen, H. L., Wang, M. C. and Seshaiah, K., "Oxidative degradation and associated mineralization of catechol, hydroquinone and resocinol catalyzed by birnessite," Chemosphere, 74, 1125-1133(2009).   DOI   ScienceOn
19 Majcher, E., Chorover, J., Bollag, J. M. and Huang, P. M., "Evolution of $CO_2$ during birnessite-induced oxidation of 14C-labled catechol," Soil Sci. Soc. Am. J., 64, 157-163(2000).   DOI   ScienceOn
20 McKenzie, R. M., "The synthesis of birnessite, cryptomelane, and some other oxides and hydroxides of manganese," Miner. Mag., 38, 493-502(1971).   DOI
21 Kennedy, B., Glidle, A. and Cunnane, V. J., "A study of the oxidation and polymerization of meta substituted phenol and aniline derivatives," J. Electroanaly. Chem., 608, 22-30 (2007).   DOI   ScienceOn
22 Canas, A. and Camarero, S., "Laccases and their natural mediators: Biotechnological toos for sustainable eco-friendly processes," Biotechnol. Advances, 28, 694-705(2010)   DOI   ScienceOn
23 Kang, K. H., Lee, D. H. and Shin, H. S., "Reaction kinetics and transformation products of 1-naphthol by manganese oxide-mediated oxidative-coupling reaction," J. Hazad. Mater., 165, 540-547(2009).   DOI   ScienceOn
24 Lu, J., Huang, Q. and Mao, L., "Removal of acetaminophene using enzyme-mediated oxidative coupling processes:1. Reaction rate and pathways," Environ. Sci. Technol., 43, 7062-7067(2009).   DOI   ScienceOn
25 Simmons, K. E., Minard, R. D., Bollag, J.-M., "Oxidative coupling and polymerization of guaiacol, a lignin derivative," Soil Sci. Soc. Am. J., 52, 1356-1360(1988).   DOI   ScienceOn
26 Choi, C. K., Harn, Y., Kim, S. U. and Shin, H. S., "Removals of PAH-quinones using birnessite-mediated oxidativetransformation processes," J. KEEE, 33(6), 396-404(2011).
27 Ulrich, H. J. and Stone, A. T., "The oxidation of chlorophenols adsorbed to manganese oxide surface," Environ. Sci. Technol., 23, 421-428(1989).   DOI   ScienceOn
28 Camarero, S., Ibarra, D., Martinez, M. J. and Martinez, A. T., "Liginin-derived compounds as efficient laccase mediators for decolorization of different types of recalcitrant dyes," Appl. Environ. Microbiaol., 71, 1775-1784(2005).   DOI   ScienceOn
29 Chen, W., Ding, Y., Iohnston, C. T., Teppen, B. J., Body, S. A. and Li, H., "Reaction of Lincosamide antibiotics with manganese oxide in aqueous solution," Environ. Sci. Technol., 44, 4486-4492(2010).   DOI   ScienceOn