The role of iron coordination in the production of reactive oxidants from ferrous iron oxidation by oxygen and hydrogen peroxide

ACS Symposium Series

Volumn 1071, Issue , 2011, Pages 177-197

  Remucal, Christina Keenan ^a   Sedlak, David L ^b  

^a ETH ZURICH   (Switzerland)

^b Berkeley   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LIGANDS; OXIDANTS; PH;

ACIDIC CONDITIONS; FENTON REACTIONS; FERROUS IRON OXIDATION; HYDROXYL RADICALS; ORGANIC LIGANDS; OXIDATIVE DAMAGE; REACTION MECHANISM; TREATMENT SYSTEMS;

IRON;

EID: 84873463230     PISSN: 00976156     EISSN: 19475918     Source Type: Book Series    
DOI: 10.1021/bk-2011-1071.ch009     Document Type: Conference Paper

References (99)

1. Southworth, B. A.; Voelker, B. M. Hydroxyl radical production via the photo-Fenton reaction in the presence of fulvic acid. Environ. Sci. Technol. 2003, 37, 1130-1136.
2. Stumm, W.; Sulzberger, B. The cycling of iron in natural environments: Considerations based on laboratory studies of heterogeneous redox processes. Geochim. Cosmochim. Acta 1992, 56, 3233-3257.
3. Barbeau, K.; Rue, E.; Bruland, K.; Butler, A. Photochemical cycling of iron in the surface ocean mediated by microbial iron(III)-binding ligands. Nature 2001, 413, 409-413.
4. McKnight, D. M.; Kimball, B. A.; Bencala, K. E. Iron photoreduction and oxidation in an acidic moutain stream. Science 1988, 240, 637-640.
5. Zuo, Y.; Hoigné, J. Formation of hydrogen peroxide and depletion of oxalic acid in atmospheric water by photolysis of iron(III)-oxalato complexes. Environ. Sci. Technol. 1992, 26, 1014-1022.
6. Sedlak, D. L.; Hoigné, J. The role of copper and oxalate in the redox cycling of iron in atmospheric waters. Atmos. Environ. 1993, 27A, 2173-2185.
7. Sedlak, D. L.; Hoigné, J.; David, M. M.; Colvile, R. N.; Seyffer, E.; Acker, K.; Wiepercht, W.; Lind, J. A.; Fuzzi, S. The cloudwater chemistry of iron and copper at Great Dun Fell, UK. Atmos. Environ. 1997, 31, 2515-2526.
8. Deutsch, F.; Hoffmann, P.; Ortner, H. Field experimental investigations on the Fe(II)-and Fe(III)-content in cloudwater samples. J. Atmos. Chem. 2001, 40, 87-105.
9. Roy, E. G.; Wells, M. L.; King, D. W. Persistence of iron(II) in surface waters of the western subarctic Pacific. Limnol. Oceanogr. 2008, 53, 89-98.
10. Emmenegger, L.; King, D. W.; Sigg, L.; Sulzberger, B. Oxidation kinetics of Fe(II) in a eutrophic Swiss lake. Environ. Sci. Technol. 1998, 32, 2990-2996.
11. Aldrich, A. P.; van den Berg, C. M. G.; Thies, H.; Nickus, U. The redox speciation of iron in two lakes. Mar. Freshwater Res. 2001, 52, 885-890.
12. Behra, P.; Sigg, L. Evidence for redox cycling of iron in atmospheric water droplets. Nature 1990, 344, 419-421.
13. Voelker, B. M.; Sulzberger, B. Effects of fulvic acid on Fe(II) oxidation by hydrogen peroxide. Environ. Sci. Technol. 1996, 30, 1106-1114.
14. Pullin, M.; Cabaniss, S. The effects of pH, ionic strength, and iron-fulvic acid interactions on the kinetics of nonphotochemical iron transformations. II. The kinetics of thermal reduction. Geochim. Cosmochim. Acta 2003, 67, 4079-4089.
15. Cohn, C. A.; Mueller, S.; Wimmer, E.; Leifer, N.; Greenbaum, S.; Strongin, D. R.; Schoonen, M. A. A. Pyrite-induced hydroxyl radical formation and its effect on nucleic acids. Geochem. T. 2006, 7, 3.
16. Pignatello, J. J.; Oliveros, E.; MacKay, A. Advanced oxidation processes for organic contaminant destruction based on the Fenton reaction and related chemistry. Crit. Rev. Environ. Sci. Technol. 2006, 36, 1-84.
17. Pignatello, J. J.; Liu, D.; Huston, P. Evidence for an additional oxidant in the photoassisted Fenton reaction. Environ. Sci. Technol. 1999, 33, 1832-1839.
18. Kwan, W. P.; Voelker, B. M. Decomposition of hydrogen peroxide and organic compounds in the presence of dissolved iron and ferrihydrite. Environ. Sci. Technol. 2002, 36, 1467-1476.
19. Majestic, B. J.; Schauer, J. J.; Shafer, M. M. Application of synchrotron radiation for measurement of iron red-ox speciation in atmospherically processed aerosols. Atmos. Chem. Phys. 2007, 7, 2475-2487.
20. Cwiertny, D. M.; Young, M. A.; Grassian, V. H. Chemistry and photochemistry of mineral dust aerosol. Annu. Rev. Phys. Chem. 2008, 59, 27-51.
21. Valko, M.; Morris, H.; Cronin, M. T. D. Metals, toxicity and oxidative stress. Curr. Med. Chem. 2005, 12, 1161-1208.
22. Haber, F.; Weiss, J. Über die katalyse des hydroperoxydes. Naturwissenschaften 1932, 20, 948-950.
23. Weiss, J. Elektronenübergangsprozesse im Mechanismus von Oxydationsund Reduktionsreaktionen in Lösungen. Naturwissenschaften 1935, 23, 64-69.
24. Stumm, W.; Lee, G. F. Oxygenation of ferrous iron. Ind. Eng. Chem. 1961, 53, 143-146.
25. King, D. W.; Lounsbury, H. A.; Millero, F. J. Rates and mechanism of Fe(II) oxidation at nanomolar total iron concentrations. Environ. Sci. Technol. 1995, 29, 818-824.
26. Bielski, B. H. J.; Cabelli, D. E.; Arudi, R. L.; Ross, A. B. Reactivity of HO/O radicals in aqueous solution. J. Phys. Chem. Ref. Data 1985, 14, 1041-1100.
27. Rush, J. D.; Bielski, B. H. J. Pulse radiolytic studies of the reactions of HO2/ O2-with Fe(II)/Fe(III) ions. The reactivity of HO2/O2-with ferric ions and its implication on the occurrence of the Haber-Weiss reaction. J. Phys. Chem. 1985, 89, 5062-5066.
28. Millero, F. J.; Sotolongo, S.; Izaguirre, M. The oxidation kinetics of Fe(II) in seawater. Geochim. Cosmochim. Acta 1987, 51, 793-801.
29. Millero, F. J.; Izaguirre, M. Effect of ionic strength and ionic interactions on the oxidation of Fe(II). J. Solution Chem. 1989, 18, 585-599.
30. Walling, C. Fenton's reagent revisited. Acc. Chem. Res. 1975, 8, 125-131.
31. Goldstein, S.; Meyerstein, D.; Czapski, G. The Fenton reagents. Free Radical Biol. Med. 1993, 15, 435-445.
32. Hug, S. J.; Leupin, O. Iron-catalyzed oxidation of arsenic(III) by oxygen and by hydrogen peroxide: pH-dependent formation of oxidants in the Fenton reaction. Environ. Sci. Technol. 2003, 37, 2734-2742.
33. Gallard, H.; de Laat, J.; Legube, B. Effect of pH on the oxidation rate of organic compounds by Fe-II/H2O2. Mechanisms and simulation. New J. Chem. 1998, 22, 263-268.
34. Keenan, C. R.; Sedlak, D. L. Factors affecting the yield of oxidants from the reaction of nanoparticulate zero-valent iron and oxygen. Environ. Sci. Technol. 2008, 42, 1262-1267.
35. Keenan, C. R.; Goth-Goldstein, R.; Lucas, D.; Sedlak, D. Oxidative stress induced by zero-valent iron nanoparticles and Fe(II) in human bronchial epithelial cells. Environ. Sci. Technol. 2009, 43, 4555-4560.
36. Vermilyea, A. W.; Voelker, B. M. Photo-Fenton reaction at near neutral pH. Environ. Sci. Technol. 2009, 43, 6927-6933.
37. Singer, P. C.; Stumm, W. Acidic mine drainage: The rate-determining step. Science 1970, 167, 1121-1123.
38. Sung, W.; Morgan, J. J. Kinetics and products of ferrous iron oxygenation in aqueous systems. Environ. Sci. Technol. 1980, 14, 561-568.
39. Luther, G. W. The Frontier-Molecular-Orbital Theory Approach in Geochemical Processes. In Aquatic Chemical Kinetics; Stumm, W., Ed.; Wiley-Interscience: New York, 1990; pp 173-198.
40. Wehrli, B., Redox Reactions of Metal Ions at Mineral Surfaces. In Aquatic Chemical Kinetics; Stumm, W., Ed.; Wiley-Interscience: New York, 1990; pp 311-336.
41. Rosso, K. M.; Morgan, J. J. Outer-sphere electron transfer kinetics of metal ion oxidation by molecular oxygen. Geochim. Cosmochim. Acta 2002, 66, 4223-4233.
42. Rosso, K. M.; Dupuis, M. Electron transfer in environmental systems: A frontier for theoretical chemistry. Theor. Chem. Acc. 2006, 116, 124-136.
43. González-Davila, M.; Santana-Casiano, J. M.; Millero, F. J. Oxidation of iron(II) nanomolar with H2O2 in seawater. Geochim. Cosmochim. Acta 2005, 69, 83-93.
44. King, D. W. Role of carbonate speciation on the oxidation rate of Fe(II) in aquatic systems. Environ. Sci. Technol. 1998, 32, 2997-3003.
45. Fenton, H. J. H. Oxidation of tartaric acid in the presence of iron. J. Chem. Soc. 1894, 65, 899-910.
46. Barb, W. G.; Baxendale, J. H.; George, P.; Hargrave, K. R. Reactions of ferrous and ferric ions with hydrogen peroxide. Part I.-The ferrous ion reaction. Trans. Faraday Soc. 1951, 47, 462-500.
47. Millero, F.; Sotolongo, S.; Stade, D.; Vega, C. Effect of ionic interactions on the oxidation of Fe(II) with H2O2 in aqueous solutions. J. Solution Chem. 1991, 20, 1079-1092.
48. Millero, F.; Sotolongo, S. The oxidation of Fe(II) with H2O2 in seawater. Geochim. Cosmochim. Acta 1989, 53, 1867-1873.
49. Walling, C. Intermediates in the reactions of Fenton type reagents. Acc. Chem. Res. 1998, 31, 155-157.
50. Duesterberg, C. K.; Waite, T. D. Kinetic modeling of the oxidation of p-hydroxybenzoic acid by Fenton's reagent: Implications of the role of quinones in the redox cycling of iron. Environ. Sci. Technol. 2007, 41, 4103-4110.
51. de Laat, J.; Gallard, H. Catalytic decomposition of hydrogen peroxide by Fe(III) in homogeneous aqueous solution: Mechanism and kinetic modeling. Environ. Sci. Technol. 1999, 33, 2726-2732.
52. Duesterberg, C. K.; Mylon, S. E.; Waite, T. D. pH effects on iron-catalyzed oxidation using Fenton's reagent. Environ. Sci. Technol 2008, 42, 8522-8527.
53. Kunai, A.; Hata, S.; Ito, S.; Sasaki, K. The role of oxygen in the hydroxylation reaction of benzene with Fenton's reagent. 18O tracer study. J. Am. Chem. Soc. 1986, 108, 601-6016.
54. Castrantas, H. M.; Gibilisco, R. D. UV destruction of phenolic compounds under alkaline conditions. ACS Symp. Ser. 1990, 422, 77-99.
55. Kochany, J.; Bolton, J. R. Mechanism of photodegradation of aqueous organic pollutants. 2. Measurement of the primary rate constants for reaction of OH radicals with benzene and some halobenzenes using an EPR spin-trapping method following the photolysis of H2O2. Environ. Sci. Technol. 1992, 26, 262-265.
56. Shen, Y.; Lin, C. The effect of pH on the decomposition of hydrophenols in aqueous solutions by ultraviolet direct photolysis and the ultraviolethydrogen peroxide process. Water Environ. Res. 2003, 75, 54-60.
57. Chen, R.; Pignatello, J. Role of quinone intermediates as electron shuttles in Fenton and photoassisted Fenton oxidations of aromatic compounds. Environ. Sci. Technol. 1997, 31, 2399-2406.
58. Ilan, Y.; Rabani, J. On some fundamental reactions in radiation chemistry: Nanosecond pulse radiolysis. Int. J. Radiat. Phys. Chem. 1976, 8, 609-611.
59. Goldstein, S.; Meyerstein, D. Comments on the mechanism of the "Fenton like" reaction. Accounts Chem. Res. 1999, 32, 547-550.
60. Bossmann, S. H.; Oliveros, E.; Gob, S.; Siegwart, S.; Dahlen, E. P.; Payawan, L.; Straub, M.; Worner, M.; Braun, A. M. New evidence against hydroxyl radicals as reactive intermediates in the thermal and photochemically enhanced fenton reactions. J. Phys. Chem. A 1998, 102, 5542-5550.
61. Buda, F.; Ensing, B.; Gribnau, M. C. M.; Baerends, E. J. DFT study of the active intermediate in the Fenton reaction. Chem.-Eur. J. 2001, 7, 2775-2783.
62. Jacobsen, F.; Holcman, J.; Sehested, K. Reactions of the ferryl ion with some compounds found in cloud water. Int. J. Chem. Kinet. 1998, 30, 215-221.
63. Buxton, G. V.; Greenstock, C. L.; Helman, W. P.; Ross, A. B. Critical review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals in aqueous solution. J. Phys. Chem. Ref. Data 1988, 17, 513-886.
64. Koppenol, W. H.; Liebman, J. F. The oxidizing nature of the hydroxyl radical. A comparison with the ferryl ion (FeO2+). J. Phys. Chem. 1984, 88, 99-101.
65. Mártire, D. O.; Caregnato, P.; Furlong, J.; Allegretti, P.; Gonzalez, M. C. Kinetic study of the reactions of oxoiron(IV) with aromatic substrates in aqueous solutions. Int. J. Chem. Kinet. 2002, 34, 488-493.
66. Katsoyiannis, I. A.; Ruettimann, T.; Hug, S. J. pH dependence of Fenton reagent generation and As(III) oxidation and removal by corrosion of zero valent iron in aerated water. Environ. Sci. Technol. 2008, 42, 7424-7430.
67. Sun, Y.; Pignatello, J. J. Chemical treatment of pesticide wastes. Evaluation of iron(III) chelates for catalytic hydrogen peroxide oxidation of 2,4-D at circumneutral pH. J. Agric. Food Chem. 1992, 40, 322-327.
68. Tachiev, G.; Roth, J. A.; Bowers, A. R. Kinetics of hydrogen peroxide decomposition with complexed and "free" iron catalysts. Int. J. Chem. Kinet. 2000, 32, 24-35.
69. Graf, E.; Mahoney, J. R.; Bryant, R. G.; Eaton, J. W. Iron-catalyzed hydroxyl radical formation. Stringent requirement for free iron coordination site. J. Biol. Chem. 1984, 259, 3620-3624.
70. Zang, V.; van Eldik, R. Kinetics and mechanisms of the autoxidation of iron(II) induced through chelation by ethylenediaminetetraacetate and related ligands. Inorg. Chem. 1990, 29, 1705-1711.
71. Kurimura, Y.; Ochiai, R.; Matsuura, N. Oxygen oxidation of ferrous ions induced by chelation. Bull. Chem. Soc. Jpn. 1968, 41, 2234-2239.
72. Welch, K. D.; Davis, T. Z.; Aust, S. D. Iron autoxidation and free radical generation: Effects of buffers, ligands, and chelators. Arch. Biochem. Biophys. 2002, 397, 360-369.
73. Keenan, C. R.; Sedlak, D. L. Ligand-enhanced reactive oxidant generation by nanoparticulate zero-valent iron and oxygen. Environ. Sci. Technol. 2008, 42, 6936-6941.
74. Lee, C.; Keenan, C. R.; Sedlak, D. L. Polyoxometalate-enhanced oxidation of organic compounds by nanoparticulate zero-valent iron and ferrous ion in the presence of oxygen. Environ. Sci. Technol. 2008, 42, 4921-4926.
75. Zepp, R. G.; Faust, B. C.; Hoigné, J. Hydroxyl radical formation in aqueoue reactions (pH 3-8) of iron(II) with hydrogen peroxide: The photo-Fenton reaction. Environ. Sci. Technol. 1992, 26, 313-319.
76. Rush, J. D.; Koppenol, W. H. Oxidizing intermediates in the reaction of ferrous EDTA with hydrogen peroxide. Reactions with oraganic molecules and ferrocytochrome-c. J. Biol. Chem. 1986, 261, 6730-6733.
77. Shiga, T.; Kishimoto, T.; Tomita, E. Aromatic hydroxylation catalyzed by Fenton's reagent. Electron paramagnetic resonance study. II. Benzoic acids. J. Phys. Chem. 1973, 77, 330-336.
78. Yamazaki, I.; Piette, L. H. EPR spin-trapping study on the oxidizing species formed in the reaction of the ferrous ion with hydrogen peroxide. J. Am. Chem. Soc. 1991, 113, 7588-7593.
79. Miles, C. J.; Brezonik, P. L. Oxygen consumption in humic-colored waters by a photochemical ferrous-ferric catalytic cycle. Environ. Sci. Technol. 1981, 15, 1089-1095.
80. Rose, A. L.; Waite, T. D. Effect of dissolved natural organic matter on the kinetics of ferrous iron oxygenation in seawater. Environ. Sci. Technol. 2003, 37, 4877-4886.
81. Miller, C. J.; Rose, A. L.; Waite, T. D. Impact of natural organic matter on H2O2-mediated oxidation of Fe(II) in a simulated freshwater system. Geochim. Cosmochim. Acta 2009, 73, 2758-2768.
82. Paciolla, M. D.; Davies, G.; Jansen, S. A. Generation of hydroxyl radicals from metal-loaded humic acids. Environ. Sci. Technol. 1999, 33, 1814-1818.
83. Tamura, H.; Goto, K.; Nagayama, M. Effect of ferric hydroxide on oxygenation of ferrous-ions in neutral solutions. Corros. Sci. 1976, 16, 197-207.
84. Kwan, W. P.; Voelker, B. M. Rates of hydoxyl radical generation and organic compound oxidation in mineral-catalyzed Fenton-like systems. Environ. Sci. Technol. 2003, 37, 1150-1158.
85. Lin, S.; Gurol, M. Catalytic decomposition of hydrogen peroxide on iron oxide: Kinetics, mechanism, and implications. Environ. Sci. Technol. 1998, 32, 1417-1423.
86. Valentine, R.; Wang, H. Iron oxide surface catalyzed oxidation of quinoline by hydrogen peroxide. J. Environ. Eng.-ASCE 1998, 124, 31-38.
87. Petigara, B.; Blough, N.; Mignerey, A. Mechanisms of hydrogen peroxide decomposition in soils. Environ. Sci. Technol. 2002, 36, 639-645.
88. Pham, A.; Lee, C.; Doyle, F.; Sedlak, D. A silica-supported iron oxide catalyst capable of activating hydrogen peroxide at neutral pH values. Environ. Sci. Technol. 2009, 43, 8930-8935.
89. Voegelin, A.; Hug, S. Catalyzed oxidation of arsenic(III) by hydrogen peroxide on the surface of ferrihydrite: An in situ ATR-FTIR study. Environ. Sci. Technol. 2003, 37, 972-978.
90. Brezonik, P.; Fulkerson-Brekken, J. Nitrate-induced photolysis in natural waters: Controls on concentrations of hydroxyl radical photo-intermediates by natural scavenging agents. Environ. Sci. Technol. 1998, 32, 3004-3010.
91. Haag, W.; Hoigne, J. Photosensitized oxidation in natural waters via OH radicals. Chemosphere 1985, 14, 1659-1671.
92. Miller, W. L.; Zepp, R. G. Photochemical production of dissolved inorganic carbon from terrestrial organic matter: Significance to the oceanic organic carbon cycle. Geophys. Res. Lett. 1995, 22, 417-420.
93. Vaughan, P.; Blough, N. Photochemical formation of hydroxyl radical by constituents of natural waters. Environ. Sci. Technol. 1998, 32, 2947-2953.
94. Pullin, M.; Bertilsson, S.; Goldstone, J.; Voelker, B. Effects of sunlight and hydroxyl radical on dissolved organic matter: Bacterial growth efficiency and production of carboxylic acids and other substrates. Limnol. Oceanogr. 2004, 49, 2011-2022.
95. Yeh, C. K.-J.; Chen, W.-S.; Chen, W.-Y. Production of hydroxyl radicals from the decomposition of hydrogen peroxide catalyzed by various iron oxides at pH 7. Pract. Period. Hazard., Toxic, Radioact. Waste Manage. 2004, 8, 161-165.
96. Nel, A.; Xia, T.; Madler, L.; Li, N. Toxic potential of materials at the nanolevel. Science 2006, 311, 622-627.
97. Groves, J. T. High-valent iron in chemical and biological oxidations. J. Inorg. Biochem. 2006, 100, 434-447.
98. Imlay, J. A.; Chin, S. M.; Linn, S. Toxic DNA damage by hydrogen peroxide through the Fenton reaction in vivo and in vitro. Science 1988, 240, 640-642.
99. Nieto-Juarez, J. I.; Pierzchla, K.; Sienkiewicz, A.; Kohn, T. Inactivation of MS2 coliphage in Fenton and Fenton-like systems: role of transition metals, hydrogen peroxide and sunlight. Environ. Sci. Technol. 2010, 44, 3351-3356.