Oxidative debromination and degradation of tetrabromo-bisphenol A by a functionalized silica-supported iron(III)-tetrakis(p-sulfonatophenyl)porphyrin catalyst

Molecules

Volumn 18, Issue 5, 2013, Pages 5360-5372

  Zhu, Qianqian ^a   Mizutani, Yusuke ^a   Maeno, Shohei ^a   Fukushima, Masami ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Iron(III) porphyrin; humic acid; silica support; catalytic oxidation; tetrabromobisphenol A

Indexed keywords

FE(II) TETRAKIS (4 SULFONATOPHENYL)PORPHYRIN; FE(II)-TETRAKIS-(4-SULFONATOPHENYL)PORPHYRIN; METALLOPORPHYRIN; POLYBROMINATED BIPHENYL; SILICON DIOXIDE; TETRABROMOBISPHENOL A;

ARTICLE; CATALYSIS; CHEMISTRY; HUMIC SUBSTANCE; METHODOLOGY; PH; WASTE WATER; WATER MANAGEMENT;

CATALYSIS; HUMIC SUBSTANCES; HYDROGEN-ION CONCENTRATION; METALLOPORPHYRINS; POLYBROMINATED BIPHENYLS; SILICON DIOXIDE; WASTE WATER; WATER PURIFICATION;

EID: 84878284122     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules18055360     Document Type: Article

References (26)

1. World Health Organization (WHO). Tetrabromobisphenol A and Derivatives: A General Introduction, Environmental Health Criteria 172; World Health Organization: Geneva, Switzerland, 1997.
2. Choi, K.-I.; Lee, S.-H.; Osako, M. Leaching of brominated flame retardants from TV housing plastics in the presence of dissolved humic matter. Chemosphere 2009, 74, 460-466.
3. Osako, M.; Kim, Y.-J.; Sakai, S. Leaching of brominated flame retardants in leachate from landfills in Japan. Chemosphere 2004, 57, 1571-1579. (Pubitemid 39422336)
4. Strack, S.; Detzel, T.; Wahl, M.; Kuch, B.; Krug, H.F. Cytotoxicity of TBBPA and effects on proliferation, cell cycle and MAPK pathways in mammalian cells. Chemosphere 2007, 67, S405-S411. (Pubitemid 46389525)
5. Lin, K.; Liu, W.; Gan, J. Reaction of tetrabromobisphenol A (TBBPA) with manganese dioxide: Kinetics, products, and pathways. Environ. Sci. Technol. 2009, 43, 4480-4486.
6. Han, S.-K.; Bilski, P.; Karriker, B.; Sik, R.H.; Chignell, C.F. Oxidation of flame retardant tetrabromobisphenol A by singlet oxygen. Environ. Sci. Technol. 2008, 42, 166-172.
7. Bastos, P.M.; Eriksson, J.; Green, N.; Bergman, Å. A standardized method for assessment of oxidative transformations of brominated phenols in water. Chemosphere 2008, 70, 1196-1202.
8. 2 degussa P25. Molecules 2012, 17, 1149-1158.
9. Sun, Z.-C.; She, Y.-B.; Zhou, Y.; Song, X.-F.; Li, K. Synthesis characterization and spectral properties of substituted tetraphenyl-porphyrin iron chloride complexes. Molecules 2011, 16, 2960-2970.
10. 5 and humic acids. Chemosphere 2010, 80, 860-865.
11. Fukushima, M.; Mizutani, Y.; Maeno, S.; Zhu, Q.; Kuramitz, H.; Nagao, S. 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 2012, 17, 48-60.
12. Nappa, M.J.; Tolman, C.A. Steric and electronic control of iron porphyrin catalyzed hydrocarbon oxidations. Inorg. Chem. 1985, 24, 4711-4719.
13. Fukushima, M.; Tatsumi, K. Effect of hydroxypropyl-β-cyclodextrin on the degradation of pentachlorophenol by potassium monopersulfate catalyzed with iron(III)-porphyrin complex. Environ. Sci. Technol. 2005, 39, 9337-9342. (Pubitemid 41741224)
14. Fukushima, M.; Tatsumi, K. 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. 2006, 245, 178-184. (Pubitemid 43165903)
15. Machado, G.S.; Castro, K.A.D.F.; Wypych, F.; Nakagaki, S. Immobilization of metalloporphyrins into nanotubes of natural halloysite toward selective catalysts for oxidation reactions. J. Mol. Catal. A-Chem. 2008, 283, 99-107.
16. Liu, J.; Guan, J.; Lu, M.; Kan, Q.; Li, Z. Hemoglobin immobilized with modified "fish-in-net" approach for the catalytic removal of aniline. J. Hazard. Mater. 2012, 217-218, 156-163.
17. Nazari, K.; Shokrollahzadeh, S.; Mahmoudi, A.; Mesbahi, F.; Matin, N. S.; Moosavi-Movahedi, A.A. Iron(III)-protoporphyrin/MCM41 catalyst as a peroxidase enzyme model: Preparation and typical test reactions. J. Mol. Catal. A-Chem. 2005, 239, 1-9. (Pubitemid 41101135)
18. Nur, H.; Hamid, H.; Endud, S.; Hamdan, H.; Ramli, Z. Iron-porphyrin encapsulated in poly(methacrylic acid) and mesoporpous Al-MCM-41 as catalysts in the oxidation of benzene to phenol. Mater. Chem. Phys. 2006, 96, 337-342. (Pubitemid 43171785)
19. Zucca, P.; Mocci, G.; Rescigno, A.; Sanjust, E. 5,10,15,20-Tetrakis(4- sulfonato-phenyl)porphine-Mn(III) immobilized on imidazole-activated silica as a novel lignin-peroxidase-like biomimetic catalyst. J. Mol. Cata. A-Chem. 2007, 278, 220-227. (Pubitemid 350052721)
20. Zucca, P.; Sollai, F.; Garau, A.; Rescigno, A.; Sanjust, E. Fe(III)-5,10,15,20-tetrakis-(pentafluorophenyl)porphine supported on pyridyl-functionalized, crosslinked poly(vinyl alcohol) as a biomimetic versatile-peroxidase-like catalyst. J. Mol. Catal. A-Chem. 2009, 306, 89-96.
21. Christoforidis, K.C.; Serestatidou, E.; Louloudi, M.; Konstantinou, I.K.; Milaeva, E.R.; Deligiannakis, Y. Mechanism of catalytic degradation of 2,4,6-trichlorophenol by a Fe-porphyrin catalyst. Appl. Catal. B-Environ. 2011, 101, 417-424.
22. 2-Fe- porphyrin catalyst. Appl. Catal. B-Environ. 2010, 95, 297-302.
23. Shigematsu, S.; Fukushima, M.; Nagao, S. Oxidative degradation of 2,6-dibromophenol using an 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. Heal. A 2010, 45, 1536-1542.
24. Fukushima, M.; Tanaka, S.; Hasebe, K.; Taga, M.; Nakamura, H. Interpretation of acid-base equilibrium of humic acid by continuous pK distribution model and electrostatic model. Anal. Chim. Acta 1995, 302, 365-373.
25. Fukushima, M.; Tanabe, Y.; Morimoto, K.; Tatsumi, K. Role of humic acid fraction with higher aromaticity in enhancing the activity of a biomimetic catalyst, tetra(p-sulfonatophenyl)-porphineiron(III). Biomacromolecules 2007, 8, 386-391. (Pubitemid 46323251)
26. Kawasaki, M.; Kuriss, A.; Fukushima, M.; Sawada, A.; Tatsumi, K. Effects of pH and organic co-solvents on the oxidation of naphthalene with peroxosulfate catalyzed by iron(III) tetrakis (p-sulfonatophenyl)porphyrin, J. Porphyr. Phthalocya. 2003, 7, 645-650.