Potassium monopersulfate oxidation of 2,4,6-tribromophenol catalyzed by a SiO2-supported iron(III)-5,10,15,20-tetrakis(4-carboxyphenyl) porphyrin

Journal of Environmental Science and Health - Part A Toxic/Hazardous Substances and Environmental Engineering

Volumn 48, Issue 13, 2013, Pages 1593-1601

  Zhu, Qianqian ^a   Mizutani, Yusuke ^a   Maeno, Shohei ^a   Nishimoto, Ryo ^a   Miyamoto, Takafumi ^a   Fukushima, Masami ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

2, 4, 6 Tribromophenol; catalytic oxidation; Humic substances; Iron(III) porphyrin catalyst; surface charges

Indexed keywords

2 ,4 ,6-TRIBROMOPHENOL; BROMINATED FLAME RETARDANTS; FUNCTIONALIZED SILICA; HALOGENATED PHENOLS; HUMIC SUBSTANCES; IRON(III) PORPHYRINS; OXIDATIVE DEGRADATION; POTASSIUM MONOPERSULFATE;

CATALYSTS; CATALYTIC OXIDATION; LEACHATE TREATMENT; OXIDATION; REUSABILITY; SILICA GEL; SURFACE CHARGE;

PORPHYRINS;

2,4,6 TRIBROMOPHENOL; BROMINE; FLAME RETARDANT; IRON 5,10,15,20 TETRAKIS(4 CARBOXYPHENYL)PORPHYRIN; PHENOL DERIVATIVE; PORPHYRIN DERIVATIVE; POTASSIUM; SILICON DIOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CONTROLLED STUDY; HUMIC SUBSTANCE; LANDFILL LEACHATE; LEACHING; OXIDATION; PH; SURFACE CHARGE;

CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, ION EXCHANGE; FERRIC COMPOUNDS; OXIDATION-REDUCTION; PHENOLS; PORPHYRINS; SILICON DIOXIDE; WASTE DISPOSAL, FLUID; WATER POLLUTANTS, CHEMICAL;

EID: 84883587921     PISSN: 10934529     EISSN: 15324117     Source Type: Journal    
DOI: 10.1080/10934529.2013.815078     Document Type: Article

References (35)

1. Nichkova, N., Germani, M., Marco, M. P. 2008. Immunochemical analysis of 2,4,6-Tribromophenol for assessment of wood contamination. J. Agric. Food Chem., 56: 29-34.
2. Thomsen, C., Lundanes, E., Becher, G. 2002. Brominated flame retardants in archived serum samples from Norway: A study on temporal trends and the role of age. Environ. Sci. Technol., 36: 1414-1418.
3. Meerts, I. A.T.M., van Zanden, J. J., Luijks, E. A.C., van Leeuwen-Bol, I., Marsh, G., Jakobsson, E., Bergman, A., Brouwer, A. 2000. Potent competitive interactions of some brominated flame retardants and related compounds with human transthyretin in vitro. Toxicol. Sci., 56: 95-104.
4. Thomsen, C., Lundanes, E., Becher, G. 2001. Brominated flame retardants in plasma samples from three different occupational groups in Norway. J. Environ. Monit., 3: 366-370.
5. Bhatnagar, A. 2007. Removal of bromophenols from water using industrial wastes as low cost adsorbents. J. Hazard. Mater., 139: 93-102.
6. Uchida, M., Furusawa, M., Okuwaki, A. 2003. Decomposition of 2-bromophenol in NaOH solution at high temperature. J. Hazard. Mater., 101: 231-238.
7. Yamada, T., Takahama, Y., Yamada, Y. 2008. Biodegradation of 2,4,6-Tribromophenol by ochrobactrum sp. Strain TB01. Biosci. Biotechnol. Biochem., 72: 1264-1271.
8. Eriksson, J., Rahm, S., Green, N., Bergman, Å., Jakobsson, E. 2004. Photochemical transformations of tetrabromobisphenol A and related phenols in water. Chemosphere, 54: 117-126.
9. Lin, K., Liu, W., Gan, J. 2009. Reaction of tetrabromobisphenol A (TBBPA) with manganese dioxide: kinetics, products, and pathways. Environ. Sci. Technol., 43: 4480-4486.
10. Bastos, P. M., Eriksson, J., Green, N., Bergaman, Å. 2008. A standardized method for assessment of oxidative transformations of brominated phenols in water. Chemosphere, 70: 1196-1202.
11. Sheldon, R. A. 1994. " Oxidation catalysis by metalloporphyrins ". In Metalloporphyrins in Catalytic Oxidations, Edited by: Sheldon, R. A. 1-27. New York: Marcel Dekker, Inc.
12. Fukushima, M. 2008. Oxidative degradation of pentachlorophenol by an iron(III)-porphyrin catalyst bound to humic acid via formaldehyde polycondensation. J. Mol. Catal. A: Chem., 286: 47-54.
13. Fukushima, M., Tatsumi, K. 2007. Degradation of pentachlorophenol in contaminated soil suspensions by potassium monopersulfate catalyzed oxidation by a supramolecular complex between tetra(p-sulfophenyl)porphineiron(III) and hydroxypropyl-β-cyclodextrin. J. Hazard. Mater., 144: 222-228.
14. Fukushima, M., Shigematsu, S., Nagao, S. 2010. Influence of humic acid type on the oxidation products of pentachlorophenol using hybrid catalysts prepared by introducing iron(III)-5,10,15,20-tetrakis(p-hydroxyphenyl) porphyrin into hydroquinone-derived humic acids. Chemosphere, 78: 1155-1159.
15. Rismayani, S., Fukushima, M., Sawada, A., Ichikawa, H., Tatsumi, K. 2004. Effects of peat humic acids on the catalytic oxidation of pentachlorophenol using metalloporphyrins and metallophthalocyanines. J. Mol. Catal. A: Chem., 217: 13-19.
16. Shukla, R. S., Robert, A., Meunier, B. 1996. Kinetic investigations of oxidative degradation of aromatic pollutant 2,4,6-trichlorophenol by an iron-porphyrin complex, a model of ligninase. J. Mol. Catal. A: Chem., 113: 45-49.
17. Fukushima, M., Tanabe, Y., Morimoto, K., Tatsumi, K. 2007. Role of humic acid fraction with higher aromaticity in enhancing the activity of a biomimetic catalyst, tetra(p-sulfonatophenyl) porphineiron(III). Biomacromolecules, 8: 386-391.
18. 5 and humic acids. Chemosphere, 80: 860-865.
19. Fukushima, M., Mizutani, Y., Maeno, S., Zhu, Q., Kuramitz, H., Nagao, S. 2012. Influence of halogen substituents on the catalytic oxidation of 2,4,6-halogenated phenols by Fe(III)-tetrakis (p-hydroxyphenyl)porphyrins and potassium monopersulfate. Molecules, 17: 48-60.
20. Fukushima, M., Shigematsu, S., Nagao, S. 2009. Oxidative degradation of 2,4,6-trichlorophenol and pentachlorophenol in contaminated soil suspension using a supramolecular catalyst prepared via formaldehyde polycondensation between tetrakis(hydroxyphenyl) porphineiron(III) and humic acid. J. Environ. Sci. Health Pt. A, 44: 1088-1097.
21. Fukushima, M., Tatsumi, K. 2005. Effect of hydroxypropyl-β-cyclo- dextrin on the degradation of pentachlorophenol by potassium monopersulfate catalyzed with iron(III)-porphyrin complex. Environ. Sci. Technol., 39: 9337-9342.
22. Fukushima, M., Tatsumi, K. 2006. Complex formation of water-soluble iron(III)-porphyrin with humic acids and their effects on the catalytic oxidation of pentachlorophenol. J. Mol. Catal. A: Chem., 245: 178-184.
23. Kitamura, Y., Mifue, M., Takatsuki, T., Iwasaki, T., Kawamoto, M., Iwado, A., Chikuma, M., Saito, Y. 2008. Ion-exchange resins modified with metal-porphyrin as a catalysis for oxidation of epinephrine (adrenaline). Catal. Commun., 9: 224-228.
24. Mifue, M., Hino, D., Sugita, H., Iwado, A., Kitamura, Y., Motohashi, N., Tsukamoto, I., Saito, Y. 2005. Peroxidase-like catalytic activity of anion-exchange resins modified with metal-porphyrins in oxidative reaction of heterocyclic amines with hydrogen peroxide. Chem. Pharm. Bull., 53: 1006-1010.
25. Shigetatsu, S., Fukushima, M., Nagao, S. 2010. Oxidative degradation of 2,6-dibromophenol using anion-exchange resin supported supramolecular catalysts of iron(III)-5,10,15,20-tetrakis (p-hydroxyphenyl) porphyrin bound to humic acid prepared via formaldehyde and urea-formaldehyde polycondensation. J. Environ. Sci. Health Pt. A, 45: 1536-1542.
26. Osako, M., Kim, Y.-J., Sakai, S. 2004. Leaching of brominated flame retardants in leachate from landfills in Japan. Chemosphere, 57: 1571-1579.
27. Fukushima, M., Tanaka, S., Nakayasu, K., Sasaki, K., Tatsumi, K. 1999. Evaluation of copper(II) binding abilities of humic substances by a continuous site-distribution model considering proton competition. Anal. Sci., 15: 185-188.
28. Benedito, F. L., Nakagaki, S., Saczk, A. A., Peralta-Zamora, P. G., Costa, C. M.M. 2003. Study of metalloporphyrin covalently bound to silica as catalyst in the ortho-dianisidine ocidation. Appl. Catal. A: Gen., 250: 1-11.
29. Fukuchi, S., Miura, A., Okabe, R., Fukushima, M., Sasaki, M., Sato, T. 2010. Spectroscopic investigations of humic-like acids formed via polycondensation reactions between glycine, catechol and glucose in the presence of natural zeolites. J. Mol. Struct., 982: 181-186.
30. Kuramochi, H., Maeda, K., Kawamoto, K. 2004. Water solubility and partitioning behavior of bromophenols. Environ. Toxicol. Chem., 23: 1386-1393.
31. Fukushima, M., Tanaka, S., Hasebe, K., Taga, M., Nakamura, H. 1995. Interpretation of the acid-base equilibrium of humic acid by a continuous p K distribution and electrostatic model. Anal. Chim. Acta, 302: 365-373.
32. Fernandez, J., Maruthamuthu, P., Kiwi, J. 2004. Photobleaching and mineralization of orange II by oxone and metal-ions involving Fenton-like chemistry under visible light. J. Photochem. Photobiol. A-Chem., 161: 185-192.
33. Lide, D. R. 2007. Handbook of Chemistry and Physics, 88th Ed., New York: CRC Press.
34. Tanaka, F., Fukushima, M., Kikuchi, A., Yabuta, H., Ichikawa, H., Tatsumi, K. 2005. Influence of chemical characteristics of humic substances on the partition coefficient of a chlorinated dioxin. Chemosphere, 58: 1319-1326.
35. Rutherford, D. W., Chiou, C. T., Kiel, D. E. 1992. Influence of soil organic matter composition on the partition of organic compounds. Environ. Sci. Technol., 26: 336-340.