Abstract
The photosensitized oxidation of 2-chlorophenol (2-CP) in aqueous solution using immobilized meso-tetraphenylporphyrin (TPP) in polyurethane nanofabrics was studied. The influence of various parameters on the reaction efficiency was investigated, i.e., 2-CP concentration, oxygen content and pH of the reaction solution and the stability of immobilized photosensitizer at the multiple use. The resistance of the structure of the photosensitizer carrier toward the solutions of various pH was also studied. The participation of molecular singlet oxygen (1O2) in the photooxidation was tested using NaN3 and imidazole quenchers of 1O2. The kinetics of the process was described using Langmuir-Hinshelwood model.
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R. F. Al-Thani, A. M. Abd-El-Haleem and A. Al-Shammri Isolation, biochemical and molecular characterization of 2-chlorophenol-degrading Bacillus isolates Afr. J. Biotechnol. 2007 6 2675–2681
W. S. El-Sayed, M. Ismaeil and F. El-Beih Cloning and nucleotide sequenceanalysis of catalytic domain encoding sequence of multicomponent phenolhydroxylase from Pseudomonas aeruginosa AT2 and Alcaligenes sp. OS2 Res. J. Cell Mol. Biol. 2009 3 20–27
K. Scow, M. Goyer, J. Perwak, C. Woodruff, K. Saterson, E. Payne and M. Wood, Exposure and Risk Assessment for Chlorinated Phenols (2-Chlorophenol, 2,4-Dichlorophenol, 2,4,6-Trichlorophenol), Arthur D. Little, Cambridge, MA, 1982
M., Czaplicka, Sources and transformations of chlorophenols in the natural environment Sci. Total Environ. 2004 322 21–39
K. Young, Y. C. Lee and W. Y., Wang, Photocatalytic decomposition of 2-chlorophenol in aqueous solution by UV-TiO2 process with applied external bias voltage J. Hazard. Mater. 2006 138 350–356
Compilation of Sampling Analysis Methods, ed. L. H. Keith, US Environmental Protection Agency, Boca Raton, FL, USA, 1991, pp. 389-486
A. Derylo-Marczewska, K. Miroslaw, A. W. Marczewski and D., Sternik, Studies of adsorption equilibria and kinetics of o-, m-, p-nitro- and chlorophenols on microporous carbons from aqueous solutions Adsorption 2010 16 359–375
B. C. Pan, Y. Xiong, Q. Su, A. M. Li, J. L. Chen and Q. X., Zhang, Role of amination of a polymeric adsorbent on phenol adsorption from aqueous solution Chemosphere 2003 51 953–962
J. G. Lin and J. S., Ma, Magnitude of effect of reaction parameters on 2-chlorophenol decomposition by ultrasonic process J. Hazard. Mater. 1999 66 291–305
V. B. Batoeva, G. G. Matafonovaa and N. I., Filippovab, Direct photolysis of chlorophenols in aqueous solutions by UV radiation from excilamps Russ. J. Appl. Chem. 2011 84 407–411
Y. Du, Q. S. Fu, Y. Li and Y., Su, Photodecomposition of 4-chlorophenol by reactive oxygen species in UV/air System J. Hazard. Mater. 2011 186 491–496
S. G. Poulopoulos, M. Nikolaki, D. Karampetsos and C. J., Philippopoulos, Photochemical treatment of 2-chlorophenol aqueous solutions using ultraviolet radiation, hydrogen peroxide and photo-Fenton re action J. Hazard. Mater. 2008 153 582–587
S. Ahmed, M. G. Rasul, W. N. Martens, R. J. Brown and M. A., Hashib, Heterogeneous photocatalytic degradation of phenols in wastewater: a review on current status and developments Desalination 2010 261 3–18
G. C. Chen, C. C. Chiou and K. Y., Wu, Electrochemical oxidation of 4-chlorophenol with granular graphite electrodes Desalination 2010 264 92–96
J. S., Miller, Rose bengal-sensitized photooxidation of 2-chlorophenol in water using solar simulated light Water Res. 2005 39 412–422
M. Bajaj, C. Gallert and J., Winter, Anaerobic biodegradation of high strength 2-chlorophenol-containing synthetic wastewater in a fixed bed reactor Chemosphere 2008 73 705–710
S. Martínez-Hernández, A. C. Texier, F. M. Cuervo-López and G. Gómez Chlorophenol consumption and its effect on the nitrifying sludge J. Hazard. Mater. 2011 185 1592–1595
Q. Song, T. Niu and H., Wang, Theoretical study of the reaction of 2,4-dichlorophenol with 1O2J. Mol. Struct. (THEOCHEM) 2008 861 27–32
K. Ozoemena, N. Kuznetsova1 and T., Nyokong, Photosensitized transformation of 4-chlorophenol in the presence of aggregated and non-aggregated metallophthalocyanines J. Photochem. Photobiol., A 2001 139 217–224
J. Mosinger, K. Lang, L. Plíštil, S. Jesenská, J. Hostomský, Z. Zelinger and P. Kubát Fluorescent polyurethane nanofabrics: a source of singlet oxygen and oxygen sensing Langmuir 2010 26 10050–2490
F. Wilkinson, W. P. Helman and A. B., Ross, Quantum yields for the photosensitized formation of the lowest electronically excited singlet state of molecular oxygen in solution J. Phys. Chem. Ref. Data 1993 22 113–262
J. Mosinger, O. Jirsak, P. Kubat, K. Lang and B. Mosinger Jr. Bactericidal nanofabric based on photoproduction of singlet oxygen J. Mater. Chem. 2007 17 164–166
H., Kautsky, Quenching of luminescence by oxygen Trans. Faraday Soc. 1939 35 216–219
R. B., Merrifield, Solid phase peptide synthesis I: The synthesis of a tetrapeptide J. Am. Chem. Soc. 1963 85 2149–2154
E. Pepe, O. Abbas, C. Rebufa, M. Simon, S. Lacombe and M., Julliard, Supported photosensitizers for the visible light activation of phenols towards oxygen J. Photochem. Photobiol., A 2005 170 143–149
R. Bonnett, M. A. Krysteva, I. G. Lalov and S. V., Artarsky, Water disinfection using photosensitizers immobilized on chitosan Water Res. 2006 40 1269–1275
M. Nowakowska, S. Zapotoczny, M. Sterzel and E., Kot, Novel water-soluble photosensitizers from dextrans Biomacromolecules 2004 5 1009–1014
H. Park, Y. Park, E. Bae and W., Choi, Photoactive-component loaded nafion film as a platform of hydrogen generation: alternative utilization of a classical sensitizing system J. Photochem. Photobiol., A 2009 203 112–118
F. M. P. R. van Laar, F. Holsteyns, I. F. J. Vankelecom, S. Smeets, W. Dehaen and P. A., Jacobs, Singlet oxygen generation using PDMS occluded dyes J. Photochem. Photobiol., A 2001 144 141–151
J. Mosinger, K. Losinska, T. Abrhamova, S. Veiserova, Z. Micka, I. Nemcova and B., Mosinger, Determination of singlet oxygen production and antibacterial effect of nonpolar porphyrins in heterogeneous systems Anal. Lett. 2000 33 1091–1104
H. D. Burrows, L. S. Ernestova, T. J. Kemp, Y. I. Skurlatov, A. P. Purmal and A. N., Yermakov, Kinetics and mechanism of photodegradation of chlorophenols Prog. React. Kinet. 1998 23 145–207
P. G. Tratnyek and J., Hoigne, Oxidation of substituted phenols in the environment: a QSAR analysis of rate constants for reaction with singlet oxygen Environ. Sci. Technol. 1991 25 1596–1604
J. Mosinger, K. Lang, P. Kubát, J. Sýkora, M. Hof, L. Plíštil and B. Mosinger, Jr. Photofunctional polyurethane nanofabrics doped by zinc tetraphenylporphyrin and zinc phthalocyanine photosensitizers J. Fluoresc. 2009 19 705–713
V. S. Ijeri, K. Daasbjerg, P. R. Ogilby and L., Poulsen, Spatial and temporal electrochemical control of singlet oxygen production and decay in photosensitized experiments Langmuir 2008 24 1070–1079
M. Tsushima, K. Tokuda and T., Ohsaka, Use of hydrodynamic chronocoulometry for simultaneous determination of diffusion coefficients and concentrations of dioxygen in various media Anal. Chem. 1994 66 4551–4556
Z. Xiong, Y. Xu, L. Zhu and J., Zhao, Photosensitized oxidation of substituted phenols on aluminum phthalocyanine-intercalated organoclay Environ. Sci. Technol. 2005 39 651–657
Y. Lin, C. Ferronato, N. Dengc and J. M., Chovelon, Study of benzylparaben photocatalytic degradation by TiO2Appl. Catal., B 2011 104 353–360
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Gmurek, M., Mosinger, J. & Miller, J.S. 2-Chlorophenol photooxidation using immobilized meso-tetraphenylporphyrin in polyurethane nanofabrics. Photochem Photobiol Sci 11, 1422–1427 (2012). https://doi.org/10.1039/c2pp25010a
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DOI: https://doi.org/10.1039/c2pp25010a