Homogeneous photo-oxidation of phenols: Influence of metals

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 110, Issue 2, 1997, Pages 167-175

  Sýkora, Ján ^a   Pado, Marián ^b   Tatarko, Miroslav ^a   Izakovič, Mário ^a  

^a SLOVAK UNIVERSITY OF TECHNOLOGY   (Slovakia)

^b TECHNICAL UNIVERSITY OF KO ICE   (Slovakia)

Author keywords

Fenton and photo Fenton reactions; Mn+ M(n 1)+ photoredox cycle; Metal complexes; Phenol photodegradation and photomineralization; Photo oxidation; Photocatalysis

Indexed keywords

EID: 0031591997     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1010-6030(97)00182-2     Document Type: Article

References (114)

1. [1] G. Scott, Atmospheric Oxidations and Antioxidants, Elsevier, New York, 1965.
2. [2] D.K.C. Hodgeman, Polym. Degrad. Stab. 1 (1979) 155.
3. [3] M.G. Nickelson, W.J. Cooper, C.N. Kuricz, T.D. Waite, Environ. Sci. Technol. 26 (1992) 115.
4. [4] Y. Hoshika, G. Muto, J. Chromatogr. 179 (1979) 105.
5. [5] K. Kuwata, M. Uebori, Y. Yamazaki, Anal. Chem. 53 (1981) 1531.
6. [6] R. Roumeliotis, W. Liebald, K.K. Unger, J. Environ. Anal. Chem. 9 (1981) 27.
7. [7] A.L. Buikema Jr., M.J. McGinniss, J. Cairns Jr., Mar. Environ. Res. 2 (1979) 87.
8. [8] M.A. Fox, M.T. Dulay, Chem. Rev. 93 (1993) 341.
9. [9] P.V. Kamat, Chem. Rev. 267 (1993) 93.
10. [10] D.F. Ollis, E. Pellizetti, N. Serpone, Environ. Sci. Technol. 25 (1991) 1523.
11. [11] N. Serpone, E. Pellizetti (Eds.), Photocatalysis: Fundamentals and Applications, Wiley, New York, 1989.
12. [12] M. Schiavello, Photocatalysis and Environment, Kluwer, Dordrecht, Netherlands, 1988.
13. [13] M. Bideau, B. Claudel, L. Faure, H. Kazouan, J. Photochem. Photobiol. A: Chem. 84 (1994) 57.
14. [14] T.Y. Wei, Y.Y. Wang, C.C. Wan, J. Photochem. Photobiol. A: Chem. 55 (1990) 115.
15. [15] K. Okamoto, Y. Yamamoto, H. Tanaka, M. Tanaka, A. Itaya, Bull. Chem. Soc. Jpn. 58 (1985) 2015.
16. [16] E.C. Butler, A.P. Davis, J. Photochem. Photobiol. A: Chem. 70 (1993) 273.
17. [17] K.E. O'Shea, C. Cardona, J. Org. Chem. 59 (1994) 5005.
18. [18] J.L. Boudenne, O. Cerclier, J. Galéa, E. Vander Vlist, Appl. Catal. A: General 143 (1996) 185.
19. [19] N. Getoff, Appl. Radiat. Isot. 37 (1986) 1103.
20. [20] N. Getoff, Proc. Indian Acad. Sci. (Chem. Sci.) 105 (1993) 373.
21. [21] F. Macášek, V. Mikulaj, P. Rajec, R. Čech, L'. Mátel, R. Kopunec, J. Kuruc, A. Švec, J. Radioanal. Nucl. Chem., Articles 191 (1995) 127.
22. [22] E.E. Hackman III, Toxic Organic Chemicals: Destruction and Waste Treatment, Noyes Data Corporation, Park Tidge, New York, 1976.
23. [23] N. Serpone, R. Terzian, P. Colarusso, C. Minero, E. Pelizzetti, H. Hidaka, Res. Chem. Intermed. 18 (1992) 183.
24. [24] C. Kutal, N. Serpone (Eds.), Photosensitive Metal Organic Systems: Mechanistic Principles and Applications, American Chemical Society, Washington DC, 1993.
25. [25] G. Steward, M.A. Fox, Res. Chem. Intermed. 21 (1995) 933.
26. [26] N. Serpone, R. Terzian, C. Minero, E. Pelizzetti, in: C. Kutal, N. Serpone (Eds.), Photosensitive Metal Organic Systems: Mechanistic Principles and Applications, American Chemical Society, Washington DC, 1993, p. 281.
27. [27] K. Okamoto, Y. Yamamoto, H. Tanaka, A. Itaya, Bull. Chem. Soc. Jpn. 58 (1985) 2023.
28. [28] C. Minero, C. Aliberti, E. Pelizzetti, R. Tezian, N. Serpone, Langmuir 7 (1991) 3081.
29. [29] A. Sclafani, L. Palmisano, M. Schiavello, Res. Chem. Intermed. 18 (1992) 211.
30. [30] M. Fujihira, Y. Satoh, T. Osa, Bull. Chem. Soc. Jpn. 55 (1982) 666.
31. [31] R.W. Matthews, J. Chem. Soc., Faraday Trans. I 80 (1984) 457.
32. [32] N.N. Lichtin, J. Dong, K.M. Vijayakumar, Water Poll. Res. J. Canada 27 (1992) 203.
33. [33] J. Cunningham, P. Sedlak, J. Photochem. Photobiol. A: Chem. 77 (1994) 255.
34. [34] A. Sclafani, L. Palmisano, E. Davi, New. J. Chem. 14 (1990) 265.
35. [35] V. Brezová, A. Blažková, E. Borošová, M. Čeppan, R. Fiala, J. Mol. Catal. 98 (1995) 109.
36. [36] T.Y. Wei, C.C. Wan, J. Photochem. Photobiol. A: Chem. 69 (1992) 241.
37. [37] A. Sclafani, L. Palmisano, E. Davi, J. Photochem. Photobiol. A: Chem. 56 (1991) 113.
38. [38] E. Pelizzetti, M. Borgarello, E. Borgarello, N. Serpone, Chemosphere 17 (1988) 499.
39. [39] S. Luňák, P. Sedlák, J. Photochem. Photobiol. A: Chem. 68 (1992) 1.
40. [40] Z. Luo, Q.H. Gao, J. Photochem. Photobiol. A: Chem. 63 (1992) 367.
41. [41] H. Kawaguchi, Environ. Technol. Lett. 5 (1984) 471.
42. [42] H. Kawaguchi, Hideki Kawaguchi Suishitsu Odaku Kenkyu 8 (1985) 443; Chem. Abstr. 104 (1986) 55664r.
43. [42] H. Kawaguchi, Hideki Kawaguchi Suishitsu Odaku Kenkyu 8 (1985) 443; Chem. Abstr. 104 (1986) 55664r.
44. [43] J. Kiwi, C. Pulgrin, P. Peringer, Appl. Catal. B: Environmental 3 (1994) 335.
45. [44] E. Lipczynska-Kochany, Environ. Technol. 12 (1991) 87.
46. [45] G. Ruppert, R. Bauer, G. Heisler, J. Photochem. Photobiol. A: Chem. 73 (1993) 75.
47. [46] P. Engelbrecht, Ph. Thomas, H. Hennig, J. Sýkora, Z. Chem, 26 (1986) 313.
48. [47] J. Sýkora, P. Engelbrecht, H. Hennig, Ph. Thomas, H. Gliesing, German Patent DD 256,323 A1, 1988.
49. [48] J. Sýkora, P. Engelbrecht, H. Hennig, Ph. Thomas, H. Gliesing, Czech Patent 255,399, 1987.
50. [49] J. Sýkora, E. Brandšteterová, A. Jabconová, Bull. Soc. Chim. Belg. 101 (1992) 821.
51. [50] Ch. Pizzocaro, M. Bolte, M.Z. Hoffman, J. Photochem. Photobiol. A: Chem. 68 (1992) 115.
52. [51] Z.P. Kachanova, Y.N. Kozlov, Russ. J. Phys. Chem. 61 (1987) 246.
53. [52] Ch. Pizzocaro, M. Bolte, H. Sun, M.Z. Hoffman, New. J. Chem. 18 (1994) 737.
54. [53] K. Lang, D.M. Wagnerová, J. Brodilová, J. Photochem. Photobiol. A: Chem. 72 (1993) 9.
55. [54] J. Kováčová, J. Sýkora, E. Brandšteterová, I. Kentošová, in: G. Ondrejovič, A. Sirota (Eds.), Contributions to Development of Coordination Chemistry, Slovak Technical University Press, Bratislava, 1993, p. 391.
56. [55] J. Sýkora, J. Kováčová, E. Brandšteterová, A. Jabconová, in: G. Ondrejovič, A. Sirota (Eds.), Contributions to Development of Coordination Chemistry, Slovak Technical University Press, Bratislava. 1993, p. 385.
57. [56] J. Sýkora, Proceedings of the 11th International Symposium on the Photochemistry and Photophysics of Coordination Compounds, Krakow, Poland, July, 1995, Polish Chemical Society, Krakow, 1995, p. 31.
58. [57] J. Sýkora, C. Kutal, Proceedings of the 15th IUPAC Symposium on Photochemistry, Prague, Czech Republic, July, 1994, Prague Institute of Chemical Technology, Prague, 1994, p. 164.
59. [58] J. Sýkora, C. Kutal, R.G. Zepp, in: G. Ondrejovič, A. Sirota (Eds.), Current Trends in Coordination Chemistry, Slovak Technical University Press, Bratislava, 1995, p. 263.
60. [59] J. Prousek, Chem. Listy 89 (1995) 11.
61. [60] Yu.N. Kozlov, V.M. Berdnikov, Russ. J. Phys. Chem. 47 (1973) 338.
62. [61] H. Sugimoto, D.T. Sawyer, J. Am. Chem. Soc. 107 (1986) 5712.
63. [62] L. Castle, J.R.L. Smith, G.V. Buxton, J. Mol. Catal. 7 (1980) 235.
64. [63] S. Tamagaki, K. Suzuki, H. Okamoto, W. Tagaki, Tetrahedron Lett. 24 (1983) 4847.
65. [64] E. Lipczynska-Kochany, Chemosphere 24 (1992) 1369.
66. [65] H.I. Joschek, S.I Miller, J. Am. Chem. Soc. 88 (1966) 3269.
67. [66] K. Omura, T. Matsuura, Tetrahedron 27 (1971) 3101.
68. [67] P. Boule, C. Guyon, J. Lemaire, Chemosphere 11 (1982) 1179.
69. [68] P. Boule, C. Guyon, J. Lemaire, Chemosphere 13 (1984) 603.
70. [69] P. Boule, C. Guyon, A. Tissot, J. Lemaire, J. Chim. Phys. 82 (1985) 513.
71. [70] K. Oudjehani, P. Boule, J. Photochem. Photobiol. A: Chem. 68 (1992) 363.
72. [71] N.A. García, J. Photochem. Photobiol. B: Biol. 22 (1994) 185.
73. [72] M. Hirano, T. Ishii, T. Morimoto, Bull. Chem. Soc. Jpn. 64 (1991) 1434.
74. [73] W.K. Seok, T.J. Meyer, J. Am. Chem. Soc. 110 (1988) 7358.
75. [74] T.S. Reddy, V. Jagannadham, Proc. Natl. Acad. Sci. India A 56 (1986) 129.
76. [75] A. Al-Ajlouni, A. Bakac, J.H. Espenson, Inorg. Chem. 32 (1993) 5792.
77. [76] Z. Szeverenyi, E.R. Milaeva, L.I. Simandi, Dioxygen Activation and Homogeneous Catalytic Oxidation, Elsevier, Amsterdam, 1991, p. 171.
78. [77] P. Barbara, C. Bianchini, K. Linn, C. Mealli, A. Meli, F. Vizza, F. Loschi, P. Zanello, Inorg. Chim. Acta 198 (1992) 31.
79. [78] J. Sýkora, E. Brandšteterová, A. Jabconová, Adv. Chem. Ser. 238 (1993) 377.
80. [79] J.E. Lyons, Ch.Y. Hsu, in: K.D. Karlin, J. Zubieta (Eds.), Biological and Inorganic Copper Chemistry, Adenine Press, New York, 1985, p. 57.
81. [80] E.L. Reilly, US Patent 3,987,068, 1976.
82. [81] J. Sýkora, J. Šima, Coord. Chem. Rev. 107 (1990) 1.
83. [82] J. Sýkora, J. Šima, Photochemistry of Coordination Compounds, Elsevier-Veda, Amsterdam, Netherlands, 1990.
84. [83] G. Ferraudi, S. Muralidharan, Coord. Chem. Rev. 336 (1981) 45.
85. [84] C. Kutal, Coord. Chem. Rev. 79 (1987) 321.
86. [85] J. Sýkora, Chem. Listy 376 (1982) 1047.
87. [86] J. Sýkora, in: H. Yersin, A. Vogler (Eds.), Photochemistry and Photophysics of Coordination Compounds, Springer Verlag, Heidelberg, Germany, 1987, p. 193.
88. [87] J. Sýkora, J. Inf. Rec. Mater. 317 (1989) 415.
89. [88] J. Sýkora, E. Horváth, J. Gažo, in: Proceedings of the 4th Symposium on Metal Complexes in Catalytic Oxidation Reactions, Wroclaw, Karpacz-Bierutovce, June, 1979, Polish Chemical Society, Poland, 1979, p. 86.
90. [89] J. Sýkora, E. Horváth, J. Gažo, Z. Anorg. Allg. Chem. 442 (1978) 245.
91. [90] E. Cervone, F. Diomedi-Camassei, I. Giannini, J. Sýkora, J. Photochem. 11 (1979) 321.
92. [91] J. Sýkora, J. Šima, D. Vatigura, E. Horváth, J. Gažo, Proceedings of the 3rd Symposium on Photochemical and Thermal Reactions of Coordination Compounds, Mogilany-Krakow, May, 1980, Polish Chemical Society, Poland, 1980, p. 12.
93. [92] J. Sýkora, M. Pado, Czech Patent 232,126, 1986.
94. [93] M. Kureková, Diploma Thesis, Slovak Technical University, Bratislava, Czechoslovakia, 1985.
95. [94] M. Pado, Diploma Thesis, Slovak Technical University, Bratislava, Czechoslovakia, 1983.
96. [95] J. Sýkora, M. Pado, Czech Patent 232,629, 1986.
97. [96] J. Sýkora, M. Jakubčová, Z. Cvengrošová, Collect. Czech. Chem. Commun. 47 (1982) 2061.
98. [97] W. Brenner, German Patent 222,124, 1972.
99. [98] J. Sýkora, A. Lopatová, M. Molčan, Proceedings of the 6th Symposium on Photochemical and Thermal Reactions of Coordination Compounds, Smolenice-Bratislava, April, 1988, Slovak Chemical Society, Czechoslovakia, 1988, p. 157.
100. [99] J. Sýkora, A. Lopatová, M. Molčan, Proceedings of the 12th Conference on Coordination Chemistry, Smolenice-Bratislava, June, 1989, Slovak Chemical Society, Czechoslovakia, 1989, p. 377.
101. [100] J. Sýkora, E. Brandšteterová, A. Jabconová, Proceedings of the 9th International Symposium on Photochemistry and Photophysics of Coordination Compounds, University of Fribourg, Fribourg, July, 1991, Switzerland, 1991, p. 47.
102. [101] J. Sýkora, E. Brandšteterová, I. Kentošová, Slovak Patent 277,939, 1995.
103. [102] J. Sýkora, E. Brandšteterová, I. Kentošová, Slovak Patent 277,940, 1995.
104. [103] C.L. Bailey, R.S. Drago, Coord. Chem. Rev. 79 (1987) 321.
105. [104] P. Bergamini, A. Maldotti, S. Sostero, O. Traverse, J. Sýkora, Inorg. Chim. Acta 385 (1984) L15.
106. [105] J. Sýkora, I. Giannini, F. Diomedi-Camassei, J. Chem. Soc., Chem. Commun. (1978) 207.
107. [106] K. Hasegawa, P. Neta, J. Phys. Chem. 82 (1978) 854.
108. [107] G. Grabner, G. Li, R.M. Quint, R. Quint, N. Getoff, J. Chem. Soc., Faraday Trans. 87 (1991) 1097.
109. [108] F. Wilkinson, J.G. Brummer, J. Phys. Chem. Ref. Data 10 (1981) 809.
110. [109] J. Sýkora, M. Tatarko, G. Grabner, C.R. Kutal, R.G. Zepp, Book of Abstracts of 212th ACS Natl. Meeting, Orlando, August, 1996, American Chemical Society, 1996, INOR 148.
111. [110] J. Sýkora, M. Tatarko, M. Izakovič, M. Pado, in: G. Ondrejovič, A. Sirota (Eds.), Progress in Coordination and Organometallic Chemistry, Slovak Technical University Press, Bratislava, 1997, p. 189.
112. [111] H.J.H. Fenton, J. Chem. Soc. 65 (1894) 899.
113. [112] R.G. Zepp, B.C. Faust, J. Hoigné, Environ. Sci. Technol. 26 (1992) 313.
114. [113] Y.I. Skurlatov, R.G. Zepp, G.L. Baughman, J. Agric. Food Chem. 31 (1983) 1065.