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

Volumn 17, Issue 1, 2012, Pages 48-60

  Fukushima, Masami ^a   Mizutani, Yusuke ^a   Maeno, Shouhei ^a   Zhu, Qianqian ^a   Kuramitz, Hideki ^b   Nagao, Seiya ^c  

^a HOKKAIDO UNIVERSITY   (Japan)

^b UNIVERSITY OF TOYAMA   (Japan)

^c KANAZAWA UNIVERSITY   (Japan)

Author keywords

2,4,6 halogenated phenols; Catalytic oxidation; Electronegativity; Halogen substituent; Humic acid; Hydroquinone; Iron(III) porphyrin

Indexed keywords

FERRIC ION; HALOGEN; HEME; PEROXYDISULFATE POTASSIUM; PHENOL DERIVATIVE; POTASSIUM DERIVATIVE; SULFATE;

ARTICLE; CATALYSIS; CHEMISTRY; HALOGENATION; OXIDATION REDUCTION REACTION; PH; SOLUTION AND SOLUBILITY;

CATALYSIS; FERRIC COMPOUNDS; HALOGENATION; HALOGENS; HEME; HYDROGEN-ION CONCENTRATION; OXIDATION-REDUCTION; PHENOLS; POTASSIUM COMPOUNDS; SOLUTIONS; SULFATES;

EID: 84856183671     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17010048     Document Type: Article

References (25)

1. 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)
2. Hakk, H.; Letcher, R.J. Metabolism in the toxicokinetics and fate of brominated flame retardants-A review. Environ. Int. 2003, 29, 801-828. (Pubitemid 37337124)
3. Keith, L.H.; Telliard, W.A. Priority pollutants I-A perspective view. Environ. Sci. Technol. 1979, 13, 416-423. (Pubitemid 9137068)
4. Sheldon, R.A. Metalloporphyrins in Catalytic Oxidations; Dekker: New York, NY, USA, 1994; pp. 325-327.
5. Shukla, R.S.; Robert, A.; Meunier, B. 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. 1996, 113, 45-49. (Pubitemid 27012648)
6. Labat, G.; Seris, J.-L.; Meunier, B. Oxidative degradation of aromatic pollutants by chemical models of ligninase based on porphyrin complexes. Angew. Chem. Ind. Ed. Engl. 1990, 29, 1471-1473.
7. Fukushima, M.; Ichikawa, H.; Kawasaki, M.; Sawada, A.; Morimoto, K.; Tatsumi, K. Effects of humic substances on the pattern of oxidation products of pentachlorophenol induced by a biomimetic catalytic system using tetra(p-sulfophenyl)porphineiron(III) and KHSO5. Environ. Sci. Technol. 2003, 37, 386-394. (Pubitemid 36109787)
8. Fukushima, M.; Sawada, A.; Kawasaki, M.; Ichikawa, H.; Morimoto, K.; Tatsumi, K.; Aoyama, M. Influence of humic substances on the removal of pentachlorophenol by a biomimetic catalytic system with a water-soluble iron(III)-porphyrin complex. Environ. Sci. Technol. 2003, 37, 386-394. (Pubitemid 36109787)
9. Rismayani, S.; Fukushima, M.; Sawada, A.; Ichikawa, H.; Tatsumi, K. Effects of peat humic acids on the catalytic oxidation of pentachlorophenol using metalloporphyrins and metallophthalocyanines. J. Mol. Catal. A Chem. 2004, 217, 13-19.
10. 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)
11. Fukushima, M.; Sawada, A.; Kawasaki, M.; Tatsumi, K. Removal of pentachlorophenol from contaminated soil by iron(III)-porphyrin complexes and potassium monopersulfate. Toxicol. Environ. Chem. 2003, 85, 39-49. (Pubitemid 38105633)
12. Fukushima, M.; Tatsumi, K. Oxidative degradation of pentachlorophenol in contaminated soil suspensions by potassium monopersulfate catalyzed with a supramolecular catalyst between iron(III)-porphyrin and hydroxypropyl-β- cyclodextrin. J. Hazard. Mater. 2007, 144, 222-228. (Pubitemid 46719614)
13. Fukushima, M.; Shigematsu, S.; Nagao, S. 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. Heal. A 2009, 44, 1088-1097.
14. Fukushima, M.; Shigematsu, S.; Nagao, S. Degradation of pentachlorophenol in a contaminated soil suspension using hybrid catalysts prepared via urea-formaldehyde polycondensation between tetrakis(hydroxyphenyl) porphineiron(III) and humic acid. Environ. Chem. Lett. 2011, 9, 223-228.
15. Nappa, M.J.; Tolman, C.A. Steric and electronic control of iron porphyrin catalyzed hydrocarbon oxidations. Inorg. Chem. 1985, 24, 4711-4719.
16. 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)
17. 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)
18. Fukushima, M. Oxidative degradation of pentachlorophenol by an iron(III)-porphyrin catalyst bound to humic acid via formaldehyde polycondensation. J. Mol. Catal. A Chem. 2008, 286, 47-54.
19. Fukushima, M.; Shigematsu, S. Introduction of 5,10,15,20- tetrakis(4-hydroxyphenyl)-porphineiron (III) into humic acid via formaldehyde polycondensation. J. Mol. Catal. A Chem. 2008, 293, 103-109.
20. Fukushima, M.; Shigematsu, S.; Nagao, S. 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 2010, 78, 1155-1159.
21. 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.
22. Fukushima, M.; Ishida, Y.; Shigematsu, S.; Kuramitz, H.; Nagao, S. Pattern of oxidation products derived from tetrabromobisphenol A in a catalytic system comprised of iron(III)-tetrakis (p-sulfophenyl)porphyrin, KHSO5 and humic acids. Chemosphere 2010, 80, 860-865.
23. Hatcher, P.G.; Bortiatynski, J.M.; Minard, R.D.; Dec, J.; Bollag, J.-M. Use of high-resolution 13C NMR to examine the enzymatic covalent binding 13C-labeled 2,4-dichlorophenol to humic substances. Environ. Sci. Technol. 1993, 27, 2098-2103. (Pubitemid 24398551)
24. Dec, J.; Bollag, J.-M. Dehalogenation of chlorinated phenols during oxidative coupling. Environ. Sci. Technol. 1994, 28, 484-490. (Pubitemid 24091713)
25. Barker, D.; Brimble, M.A.; Do, P.; Turner, P. Addition of silyloxydienes to 2,6-dibromo-1,4- benzoquinone: An approach to highly oxygenated bromonaphthoquinones for the synthesis of thysanone. Tetrahedron 2003, 59, 2441-2449. (Pubitemid 36316086)