Photooxidation of Some Organic Sulfides under UV Light Irradiation Using Titanium Dioxide Photocatalyst

Vosooghian, Hakimeh; Habibi, Mohammad Hossein

doi:https://doi.org/10.1155/2007/89759

International Journal of Photoenergy

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Research Article | Open Access

Volume 2007 | Article ID 089759 | https://doi.org/10.1155/2007/89759

Photooxidation of Some Organic Sulfides under UV Light Irradiation Using Titanium Dioxide Photocatalyst

Hakimeh Vosooghian¹and Mohammad Hossein Habibi¹

Academic Editor: Terry Egerton

Received07 Apr 2006

Revised04 Oct 2006

Accepted09 Oct 2006

Published20 Dec 2006

Abstract

The photocatalytic oxidation of three organic sulfide compounds (thioethers); methyl phenyl sulfide (MPS), benzyl phenyl sulfide (BPS), and diphenyl sulfide (dPS) using titanium dioxide (TiO2) photocatalyst suspension under UV light irradiation in aqueous-acetonitrilic (5/95), was studied. Three types of experiments were carried out: (a) the solution was eliminated from atmospheric oxygen by a flow of argon before irradiation, (b) the solution was irradiated with continuous bubbling of oxygen, and (c) the irradiation was carried out at neutral atmospheric oxygen conditions. Results showed that the process will proceed in the presence of pure oxygen much better than atmospheric oxygen or in the absence of oxygen. In fact, no detectable products were observed in the presence of atmospheric oxygen or argon flux. Besides the main products such as methyl phenyl sulfoxide, benzyl phenyl sulfoxide, diphenyl sulfoxide, diphenyl disulfide, benzaldehyde, phenyl propyl sulfide, and n-buthyl phenyl sulfide, trace concentrations of dibenzyl, biphenyl, thiophenol, benzyl alcohol, benzene, benzyl phenyl sulfone, diphenyl sulfone, and methyl phenyl sulfone were detected. Thus in summary, this study provides an example of specific, controlled oxidative chemistry in organic substrates adsorbed on photoactivated TiO2 surface.

References

V. Iliev, A. Ileva, and L. Bilyarska, “Oxidation and photooxidation of sulfur-containing compounds in the presence of immobilized phthalocyanine complexes,” Journal of Molecular Catalysis A: Chemical, vol. 126, no. 2-3, pp. 99–108, 1997.
View at: Publisher Site | Google Scholar
J. R. Salazar, Handbook of Petroleum Processes, Part 9, edited by R. A. Mayers, McGraw-Hill, New York, NY, USA, 1986.
C. Wilson and D. M. Hirst, Progress in Reaction Kinetics, vol. 21, pp. 69–75, 1996.
M. A. Fox and M. T. Dulay, “Heterogeneous photocatalysis,” Chemical Reviews, vol. 93, no. 1, pp. 341–357, 1993.
View at: Publisher Site | Google Scholar
M. R. Hoffmann, S. T. Martin, W. Choi, and D. W. Bahnemann, “Environmental applications of semiconductor photocatalysis,” Chemical Reviews, vol. 95, no. 1, pp. 69–96, 1995.
View at: Publisher Site | Google Scholar
A. L. Linsebigler, G. Lu, and J. T. Yates Jr., “Photocatalysis on ${TiO}_{2}$ surfaces: principles, mechanisms, and selected results,” Chemical Reviews, vol. 95, no. 3, pp. 735–758, 1995.
View at: Publisher Site | Google Scholar
A. Mills and S. Le Hunte, “An overview of semiconductor photocatalysis,” Journal of Photochemistry and Photobiology A: Chemistry, vol. 108, no. 1, pp. 1–35, 1997.
View at: Publisher Site | Google Scholar
A. Fujishima, T. N. Rao, and D. A. Tryk, “Titanium dioxide photocatalysis,” Journal of Photochemistry and Photobiology C: Photochemistry Reviews, vol. 1, no. 1, pp. 1–21, 2000.
View at: Publisher Site | Google Scholar
A. Mills, R. H. Davies, and D. Worsley, “Water purification by semiconductor photocatalysis,” Chemical Society Reviews, vol. 22, no. 6, pp. 417–425, 1993.
View at: Publisher Site | Google Scholar
P. V. Kamat, “Photochemistry on nonreactive and reactive (semiconductor) surfaces,” Chemical Reviews, vol. 93, no. 1, pp. 267–300, 1993.
View at: Publisher Site | Google Scholar
P. V. Kamat, “Photophysical, photochemical and photocatalytic aspects of metal nanoparticles,” Journal of Physical Chemistry B, vol. 106, no. 32, pp. 7729–7744, 2002.
View at: Publisher Site | Google Scholar
J. F. Kenneke, J. L. Ferry, and W. H. Glaze, “The titanium dioxide mediated photocatalytic degradation of chloroalkene,” in Photocatalytic Purification and Treatment of Water and Air, D. F. Ollis and H. Al-Ekabi, Eds., pp. 179–191, Elsevier, London, Uk, 1993.
View at: Google Scholar
A. Fujishima, K. Hashimoto, and T. Watanabe, ${TiO}_{2}$ Photocatalysis: Fundamentals and Applications, BKC, Tokyo, Japan, 1999.
J. Zhao and X. Yang, “Photocatalytic oxidation for indoor air purification: a literature review,” Building and Environment, vol. 38, no. 5, pp. 645–654, 2003.
View at: Publisher Site | Google Scholar
S. Hager, R. Bauer, and G. Kudielka, “Photocatalytic oxidation of gaseous chlorinated organics over titanium dioxide,” Chemosphere, vol. 41, no. 8, pp. 1219–1225, 2000.
View at: Publisher Site | Google Scholar
R. Nakamura, A. Imanishi, K. Murakoshi, and Y. Nakato, “In situ FTIR studies of pimary intermediates of photocatalytic reactions on nanocrystalline ${TiO}_{2}$ films in contact with aqueous solutions,” Journal of the American Chemical Society, vol. 125, no. 24, pp. 7443–7450, 2003.
View at: Publisher Site | Google Scholar
S. Sato, K. Ueda, Y. Kawasaki, and R. Nakamura, “In situ IR observation of surface species during the photocatalytic decomposition of acetic acid over ${TiO}_{2}$ films,” Journal of Physical Chemistry B, vol. 106, no. 35, pp. 9054–9058, 2002.
View at: Publisher Site | Google Scholar
R. B. Draper and M. A. Fox, “Titanium dioxide photosensitized reactions studied by diffuse reflectance flash photolysis in aqueous suspensions of ${TiO}_{2}$ powder,” Langmuir, vol. 6, no. 8, pp. 1396–1402, 1990.
View at: Publisher Site | Google Scholar
A. Y. Nosaka, T. Fujiwara, H. Yagi, H. Akutsu, and Y. Nosaka, “Photocatalytic reaction sites at the ${TiO}_{2}$ surface as studied by solid-state 1H NMR spectroscopy,” Langmuir, vol. 19, no. 6, pp. 1935–1937, 2003.
View at: Publisher Site | Google Scholar
M. A. Fox and M. T. Dulay, “Acceleration of secondary dark reactions of intermediates derived from adsorbed dyes on irradiated ${TiO}_{2}$ powders,” Journal of Photochemistry and Photobiology A: Chemistry, vol. 98, no. 1-2, pp. 91–101, 1996.
View at: Publisher Site | Google Scholar
D. P. Colombo Jr. and R. M. Bowman, “Does interfacial charge transfer compete with charge carrier recombination? A femtosecond diffuse reflectance investigation of ${TiO}_{2}$ nanoparticles,” Journal of Physical Chemistry, vol. 100, no. 47, pp. 18445–18449, 1996.
View at: Publisher Site | Google Scholar
A. Furube, T. Asahi, H. Masuhara, H. Yamashita, and M. Anpo, “Direct observation of interfacial hole transfer from a photoexcited ${TiO}_{2}$ particle to an adsorbed molecule SCN- by femtosecond diffuse reflectance spectroscopy,” Research on Chemical Intermediates, vol. 27, no. 1-2, pp. 177–187, 2001.
View at: Publisher Site | Google Scholar
T. Tachikawa, S. Tojo, M. Fujitsuka, and T. Majima, “One-electron oxidation of aromatic sulfides adsorbed on the surface of ${TiO}_{2}$ particles studied by time-resolved diffuse reflectance spectroscopy,” Chemical Physics Letters, vol. 382, no. 5-6, pp. 618–625, 2003.
View at: Publisher Site | Google Scholar
C. D. Jaeger and A. J. Bard, “Spin trapping and electron spin resonance detection of radical intermediates in the photodecomposition of water at titanium dioxide particulate systems ,” Journal of Physical Chemistry, vol. 83, no. 24, pp. 3146–3146, 1979.
View at: Publisher Site | Google Scholar
R. F. Howe and M. Graetzel, “EPR study of hydrated anatase under UV irradiation,” Journal of Physical Chemistry, vol. 91, no. 14, pp. 3906–3909, 1987.
View at: Publisher Site | Google Scholar
O. I. Micic, Y. Zhang, K. R. Cromack, A. D. Trifunac, and M. C. Thurnauer, “Trapped holes on titania colloids studied by electron paramagnetic resonance,” Journal of Physical Chemistry, vol. 97, no. 28, pp. 7277–7283, 1993.
View at: Publisher Site | Google Scholar
J. Fan and J. T. Yates Jr., “Mechanism of photooxidation of trichloroethylene on ${TiO}_{2}$ : detection of intermediates by infrared spectroscopy,” Journal of the American Chemical Society, vol. 118, no. 19, pp. 4686–4692, 1996.
View at: Publisher Site | Google Scholar
D. Lawless, N. Serpone, and D. Meisel, “Role of hydroxyl radicals and trapped holes in photocatalysis. A pulse radiolysis study,” Journal of Physical Chemistry, vol. 95, no. 13, pp. 5166–5170, 1991.
View at: Publisher Site | Google Scholar
M. W. Peterson, J. A. Turner, and A. J. Nozik, “Mechanistic studies of the photocatalytic behavior of titania: particles in a photoelectrochemical slurry cell and the relevance to photodetoxification reactions,” Journal of Physical Chemistry, vol. 95, no. 1, pp. 221–225, 1991.
View at: Publisher Site | Google Scholar
C. Kormann, D. W. Bahnemann, and M. R. Hoffmann, “Photolysis of chloroform and other organic molecules in aqueous ${TiO}_{2}$ suspensions,” Environmental Science and Technology, vol. 25, no. 3, pp. 494–500, 1991.
View at: Publisher Site | Google Scholar
J. Cunningham and S. Srijarahai, “Isotope-effect evidence for hydroxyl radical involvement in alcohol photo-oxidation sensitized by ${TiO}_{2}$ in aqueous suspension,” Journal of Photochemistry and Photobiology A: Chemistry, vol. 43, no. 3, pp. 329–335, 1988.
View at: Publisher Site | Google Scholar
M. A. Grela, M. E. J. Coronel, and A. J. Colussi, “Quantitative spin-trapping studies of weakly illuminated titanium dioxide sols. Implications for the mechanism of photocatalysis,” Journal of Physical Chemistry, vol. 100, no. 42, pp. 16940–16946, 1996.
View at: Publisher Site | Google Scholar
P. F. Schwarz, N. J. Turro, S. H. Bossmann, A. M. Braun, A.-M. A. Abdel Wahab, and H. Dürr, “A new method to determine the generation of hydroxyl radicals in illuminated ${TiO}_{2}$ suspensions,” Journal of Physical Chemistry B, vol. 101, no. 36, pp. 7127–7134, 1997.
View at: Publisher Site | Google Scholar
M. H. Habibi and H. Vosooghian, “Photocatalytic degradation of some organic sulfides as environmental pollutants using titanium dioxide suspension,” Journal of Photochemistry and Photobiology A: Chemistry, vol. 174, no. 1, pp. 45–52, 2005.
View at: Publisher Site | Google Scholar
T. Tachikawa, S. Tojo, M. Fujitsuka, and T. Majima, “Influences of adsorption on ${TiO}_{2}$ photocatalytic one-electron oxidation of aromatic sulfides studied by time-resolved diffuse reflectance spectroscopy,” Journal of Physical Chemistry B, vol. 108, no. 19, pp. 5859–5866, 2004.
View at: Publisher Site | Google Scholar
T. Tachikawa, S. Tojo, M. Fujitsuka, and T. Majima, “Photocatalytic one-electron oxidation of biphenyl derivatives strongly coupled with the ${TiO}_{2}$ surface,” Langmuir, vol. 20, no. 7, pp. 2753–2759, 2004.
View at: Publisher Site | Google Scholar
T. Tachikawa, S. Tojo, M. Fujitsuka, and T. Majima, “Formation of the dimer radical cation of aromatic sulfide on the ${TiO}_{2}$ surface during photocatalytic reactions,” Langmuir, vol. 20, no. 11, pp. 4327–4329, 2004.
View at: Publisher Site | Google Scholar
R. B. Draper and M. A. Fox, “Titanium dioxide photooxidation of thiocyanate: ${(SCN)}_{2}^{\cdot -}$ studied by diffuse reflectance flash photolysis,” Journal of Physical Chemistry, vol. 94, no. 11, pp. 4628–4634, 1990.
View at: Publisher Site | Google Scholar
R. B. Draper and M. A. Fox, “Titanium dioxide photosensitized reactions studied by diffuse reflectance flash photolysis in aqueous suspensions of ${TiO}_{2}$ powder,” Langmuir, vol. 6, no. 8, pp. 1396–1402, 1990.
View at: Publisher Site | Google Scholar
A. V. Vorontsov, E. V. Savinov, L. Davydov, and P. G. Smirniotis, “Photocatalytic destruction of gaseous diethyl sulfide over ${TiO}_{2}$ ,” Applied Catalysis B: Environmental, vol. 32, no. 1-2, pp. 11–24, 2001.
View at: Publisher Site | Google Scholar
A. V. Vorontsov, E. N. Savinov, C. Lion, and P. G. Smirniotis, “ ${TiO}_{2}$ reactivation in photocatalytic destruction of gaseous diethyl sulfide in a coil reactor,” Applied Catalysis B: Environmental, vol. 44, no. 1, pp. 25–40, 2003.
View at: Publisher Site | Google Scholar
M. H. Habibi, S. Tangestaninejad, and B. Yadollahi, “Photocatalytic mineralisation of mercaptans as environmental pollutants in aquatic system using ${TiO}_{2}$ suspension,” Applied Catalysis B: Environmental, vol. 33, no. 1, pp. 57–63, 2001.
View at: Publisher Site | Google Scholar
M. H. Habibi, S. Tangestaninejad, and B. Yadollahi, “Detoxification of water containing para-methyl thiophenol with photocatalytic oxygenation on titanium dioxide,” Journal of Industrial Pollution Control, vol. 24, pp. 80–89, 2000.
View at: Google Scholar
M. H. Habibi, M. Khaledisardashti, and M. Montazerozohori, “Photocatalytic mineralisation of aniline derivatives in aquatic systems using semiconductor oxides,” Annali di Chimica, vol. 94, no. 5-6, pp. 421–428, 2004.
View at: Publisher Site | Google Scholar
G. Pothenberger, J. Moser, M. Graetzel, N. Serpone, and D. K. Sharama, “Charge carrier trapping and recombination dynamics in small semiconductor particles,” Journal of the American Chemical Society, vol. 107, no. 26, pp. 8054–8059, 1985.
View at: Publisher Site | Google Scholar
N. Serpone, D. Lawless, R. Khairutdinov, and E. Pelizzetti, “Subnanosecond relaxation dynamics in ${TiO}_{2}$ colloidal sols (particle sizes $Rp = 1.0 - 13.4$ nm). Relevance to heterogeneous photocatalysis,” Journal of Physical Chemistry, vol. 99, no. 45, pp. 16655–16661, 1995.
View at: Publisher Site | Google Scholar
D. W. Bahnemann, M. Hilgendorff, and R. Memming, “Charge carrier dynamics at ${TiO}_{2}$ particles: reactivity of free and trapped holes,” Journal of Physical Chemistry B, vol. 101, no. 21, pp. 4265–4275, 1997.
View at: Google Scholar
D. P. Colombo Jr., K. A. Roussel, J. Saeh, D. S. Skinner, J. J. Cavaleri, and R. M. Bowman, “Femtosecond study of the intensity dependence of electron-hole dynamics in ${TiO}_{2}$ nanoclusters,” Chemical Physics Letters, vol. 232, no. 3, pp. 207–214, 1995.
View at: Publisher Site | Google Scholar
D. E. Skinner, D. P. Colombo Jr., J. J. Cavaleri, and R. M. Bowman, “Femtosecond investigation of electron trapping in semiconductor nanoclusters,” Journal of Physical Chemistry, vol. 99, no. 20, pp. 7853–7856, 1995.
View at: Publisher Site | Google Scholar
J. E. Packer, “The radiation chemistry of thiol,” in The Chemistry of the Thiol Group, Part 2, S. Patai, Ed., p. 501, John Wiley & Sons, London, UK, 1974.
View at: Google Scholar
M. R. Nimlos, E. J. Wolfrum, M. L. Brewer, J. A. Fennell, and G. Bintner, “Gas-phase heterogeneous photocatalytic oxidation of ethanol: pathways and kinetic modeling,” Environmental Science and Technology, vol. 30, no. 10, pp. 3102–3110, 1996.
View at: Publisher Site | Google Scholar
R. S. Davidson and J. E. Pratt, “The titanium dioxide sensitised photo-oxidation of sulphides,” Tetrahedron Letters, vol. 24, no. 52, pp. 5903–5906, 1983.
View at: Publisher Site | Google Scholar
E. L. Clenna, W. Zhou, and J. Chan, “Mechanistic organic chemistry in a microreactor. Zeolite-controlled photooxidations of organic sulfides,” The Journal of Organic Chemistry, vol. 67, no. 26, pp. 9368–9378, 2002.
View at: Publisher Site | Google Scholar

Copyright

Copyright © 2007 Hakimeh Vosooghian and Mohammad Hossein Habibi. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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