Kinetics study on the degradation of a model naphthenic acid by ethylenediamine-N,N’-disuccinic acid-modified Fenton process

Journal of Hazardous Materials

Volumn 318, Issue , 2016, Pages 371-378

  Zhang, Ying ^a   Klamerth, Nikolaus ^a   Messele, Selamawit Ashagre ^a   Chelme Ayala, Pamela ^a   Gamal El Din, Mohamed ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Cyclohexanoic acid; Ethylenediamine N,N disuccinic acid; Fenton process; OH; Redox potential

Indexed keywords

OIL SANDS; ORGANIC ACIDS; RATE CONSTANTS; REDOX REACTIONS;

CYCLOHEXANOIC ACIDS; ETHYLENE DIAMINE; FENTON PROCESS; HALF-WAVE POTENTIAL; HYDROXYL RADICALS; OIL SANDS PROCESS-AFFECTED WATERS; REDOX POTENTIALS; SECOND-ORDER RATE CONSTANTS;

IRON COMPOUNDS;

CUPRIC ION; CYCLOHEXANE DERIVATIVE; CYCLOHEXANOIC ACID; ETHYLENEDIAMINE DERIVATIVE; ETHYLENEDIAMINE N,N' DISUCCINIC ACID; HYDROGEN PEROXIDE; HYDROXYL RADICAL; IRON; NAPHTHALENE DERIVATIVE; NAPHTHENIC ACID; REAGENT; SUPEROXIDE; UNCLASSIFIED DRUG;

CARBOXYLIC ACID; DEGRADATION; HYDROGEN PEROXIDE; HYDROXYL RADICAL; OIL SAND; PH; REACTION KINETICS; REACTION RATE; REDOX POTENTIAL; TOXICITY;

ARTICLE; BIOREMEDIATION; CHEMICAL MODIFICATION; CONTROLLED STUDY; FENTON REACTION; OIL SAND PROCESS AFFECTED WATER; OXIDATION KINETICS; PH; REACTION ANALYSIS; TAR SAND; WASTE COMPONENT REMOVAL; WASTE WATER TREATMENT PLANT; WATER TREATMENT;

EID: 84978402711     PISSN: 03043894     EISSN: 18733336     Source Type: Journal    
DOI: 10.1016/j.jhazmat.2016.06.063     Document Type: Article

References (70)

1. [1] He, Y.H., Wiseman, S.B., Hecker, M., Zhang, X.W., Wang, N., Perez, L.A., Jones, P.D., Gamal El-Din, M., Martin, J.W., Giesy, J.P., Effect of ozonation on the estrogenicity and androgenicity of oil sands process-affected water. Environ. Sci. Technol. 45 (2011), 6268–6274.
2. [2] Kannel, P.R., Gan, T.Y., Naphthenic acids degradation and toxicity mitigation in tailings wastewater systems and aquatic environments: a review. J. Environ. Sci. Health Part A Toxic/Hazard. Subst. Environ. Eng. 47 (2012), 1–21.
3. 2 process under various conditions. Sci. Total. Environ. 426 (2012), 387–392.
4. [4] Allen, E.W., Process water treatment in Canada's oil sands industry: I. Target pollutants and treatment objectives. J. Environ. Eng. Sci. 7 (2008), 123–138.
5. [5] Fu, H., Gamal El-Din, M., Smith, D.W., MacKinnon, M., Zubot, W., Ozone treatment of naphthenic acids in Athabasca oil sands process-affected water. First International Oil Sands Tailings Conference, Edmonton, AB, Canada, 2008.
6. [6] Scott, A.C., Zubot, W., MacKinnon, M.D., Smith, D.W., Fedorak, P.M., Ozonation of oil sands process water removes naphthenic acids and toxicity. Chemosphere 71 (2008), 156–160.
7. [7] Wang, Y.N., Application of Coagulation-Flocculation Process for Treating Oil Sands Process-Affected Water. 2011, Department of Civil and Environmental Engineering, University of Alberta, Edmonton, AB, Canada.
8. [8] Basu, S., Wei, I.W., Advanced chemical oxidation of 2,4,6 trichlorophenol in aqueous phase by Fenton's reagent-part i: effects of the amounts of oxidant and catalyst on the treatment reaction. Chem. Eng. Commun. 164 (1998), 111–137.
9. [9] Basu, S., Wei, I.W., Advanced chemical oxidation of 2,4,6 trichlorophenol in aqueous phase by Fenton's reagent-Part II: effects of various reaction parameters on the treatment reaction. Chem. Eng. Commun. 164 (1998), 139–151.
10. [10] Teel, A.L., Warberg, C.R., Atkinson, D.A., Watts, R.J., Comparison of mineral and soluble iron Fenton's catalysts for the treatment of trichloroethylene. Water Res. 35 (2001), 977–984.
11. [11] Li, Y.C., Bachas, L.G., Bhattacharyya, D., Kinetics studies of trichlorophenol destruction by chelate-based Fenton reaction. Environ. Eng. Sci. 22 (2005), 756–771.
12. [12] Kwan, W.P., Voelker, B.M., Rates of hydroxyl radical generation and organic compound oxidation in mineral-catalyzed Fenton-like systems. Environ. Sci. Technol. 37 (2003), 1150–1158.
13. [13] Lipczynska-Kochany, E., Kochany, J., Effect of humic substances on the Fenton treatment of wastewater at acidic and neutral pH. Chemosphere 73 (2008), 745–750.
14. [14] Pignatello, J.J., Oliveros, E., MacKay, A., Advanced oxidation processes for organic contaminant destruction based on the Fenton reaction and related chemistry. Crit. Rev. Env. Sci. Tec. 36 (2006), 1–84.
15. [15] Sun, Y.F., 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. 40 (1992), 322–327.
16. [16] Georgi, A., Schierz, A., Trommler, U., Horwitz, C.P., Collins, T.J., Kopinke, F.D., Humic acid modified Fenton reagent for enhancement of the working pH range. Appl. Catal. B 72 (2007), 26–36.
17. [17] Huang, W.Y., Brigante, M., Wu, F., Mousty, C., Hanna, K., Mailhot, G., Assessment of the Fe (III)–EDDS complex in Fenton-like processes: from the radical formation to the degradation of bisphenol A. Environ. Sci. Technol. 47 (2013), 1952–1959.
18. [18] Nagaraju, V., Goje, T., Crouch, A.M., Determination of copper and iron using [S, S']-Ethylenediaminedisuccinic acid as a chelating agent in wood pulp by capillary electrophoresis. Anal. Sci. 23 (2007), 493–496.
19. [19] Metsärinne, S., Tuhkanen, T., Aksela, R., Photodegradation of ethylenediaminetetraacetic acid (EDTA) and ethylenediamine disuccinic acid (EDDS) within natural UV radiation range. Chemosphere 45 (2001), 949–955.
20. [20] Pavelčik, F., Majer, J., New complexanes. XXXIV. Preparation and properties of the meso and rac forms of ethy! enediamine-iV, iV'-disuccinic acid. Chem. Zvesti 32 (1978), 37–41.
21. [21] Schowanek, D., Feijtel, T.C., Perkins, C.M., Hartman, F.A., Federle, T.W., Larson, R.J., Biodegradation of [S S],[R, R] and mixed stereoisomers of ethylene diamine disuccinic acid (EDDS), a transition metal chelator. Chemosphere 34 (1997), 2375–2391.
22. [22] Jones, P.W., Williams, D.R., Chemical speciation used to assess [S, S′]-ethylenediaminedisuccinic acid (EDDS) as a readily-biodegradable replacement for EDTA in radiochemical decontamination formulations. Appl. Radiat. Isotopes 54 (2001), 587–593.
23. [23] Jaworska, J.S., Schowanek, D., Feijtel, T.C., Environmental risk assessment for trisodium [S S]-ethylene diamine disuccinate, a biodegradable chelator used in detergent applications. Chemosphere 38 (1999), 3597–3625.
24. [24] OECD, OECD Guidelines for Testing of Chemicals, Degradation and Accumulation, Paris (1996).
25. [25] Whitburn, J.S., Wilkinson, S.D., Williams, D.R., Chemical speciation of ethylenediamine-N,N′-disuccinic acid (EDDS) and its metal complexes in solution. Chem. Speciat. Bioavailab. 11 (1999), 85–93.
26. [26] Willkinson, S.D., Chemical Speciation of a Biodegradable Replacement Ligand for EDTA. 1998, University of Wales, Cardiff.
27. [27] De Laat, J., Dao, Y.H., Hamdi El Najjar, N., Daou, C., Effect of some parameters on the rate of the catalysed decomposition of hydrogen peroxide by iron (III)-nitrilotriacetate in water. Water Res. 45 (2011), 5654–5664.
28. 2 advanced oxidation process. Water Res. 47 (2013), 2881–2889.
29. 2 advanced oxidation technology: the rate constants for the tert-butyl formate ester and 2,4-dinitrophenol. J. Adv. Oxid. Technol. 4 (1999), 231–236.
30. [30] 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. J. Phys. Chem. Ref. Data 17 (1988), 513–886.
31. [31] Pereira, V.J., Weinberg, H.S., Linden, K.G., Singer, P.C., UV degradation kinetics and modeling of pharmaceutical compounds in laboratory grade and surface water via direct and indirect photolysis at 254 nm. Environ. Sci. Technol. 41 (2007), 1682–1688.
32. 2 technique. Environ. Sci. Technol. 36 (2002), 3936–3944.
33. [33] Klamerth, N., Malato, S., Maldonado, M.I., Agüera, A., Fernández-Alba, A., Modified photo-Fenton for degradation of emerging contaminants in municipal wastewater effluents. Catal. Today 161 (2011), 241–246.
34. [34] Munoz, M., Alonso, J., Bartroli, J., Valiente, M., Automated spectrophotometric determination of titanium (IV) in water and brines by flow injection based on its reaction with hydrogen peroxide. Analyst 115 (1990), 315–318.
35. [35] Klamerth, N., Malato, S., Aguera, A., Fernandez-Alba, A., Mailhot, G., Treatment of municipal wastewater treatment plant effluents with modified photo-Fenton as a tertiary treatment for the degradation of micro pollutants and disinfection. Environ. Sci. Technol. 46 (2012), 2885–2892.
36. [36] Zhang, Y., Klamerth, N., Gamal El-Din, M., Degradation of a model naphthenic acid by nitrilotriacetic acid-modified fenton process. Chem. Eng. J. 292 (2016), 340–347.
37. 2. J. Phys. Chem. A 114 (2010), 12067–12074.
38. [38] Kleinberg, J., William, J., Argersinger, J.R., Ernest, G., Inorganic Chemistry. 1960, D.C. Heath and Company, Lexington, Massachusetts, United States.
39. [39] De Laat, J., Gallard, H., Catalytic decomposition of hydrogen peroxide by Fe (III) in homogeneous aqueous solution: mechanism and kinetic modeling. Environ. Sci. Technol. 33 (1999), 2726–2732.
40. 2 oxidation reactions in dilute aqueous solution using atrazine as a model organic compound. Water Res. 34 (2000), 3107–3116.
41. [41] Dao, Y.H., De Laat, J., Hydroxyl radical involvement in the decomposition of hydrogen peroxide by ferrous and ferric-nitrilotriacetate complexes at neutral pH. Water Res. 45 (2011), 3309–3317.
42. [42] Pérez-Estrada, L.A., Han, X., Drzewicz, P., Gamal El-Din, M., Fedorak, P.M., Martin, J.W., Structure–reactivity of naphthenic acids in the ozonation process. Environ. Sci. Technol. 45 (2011), 7431–7437.
43. [43] Anbar, M., Meyerstein, D., Neta, P., Reactivity of aliphatic compounds towards hydroxyl radicals. J. Chem. Soc. B, 1966, 742–747.
44. [44] Li, J., 17beta-Estradiol Degradation Photoinduced by Iron Complex, Clay and Iron Oxide Minerals: Effect of the Iron Complexing Agent Ethylenediamine-N,N'-disuccinic Acid. 2010, Université Blaise Pascal-Clermont-Ferrand II; Université de Wuhan.
45. [45] Orama, M., Hyvönen, H., Saarinen, H., Aksela, R., Complexation of [S, S] and mixed stereoisomers of N, N′-ethylenediaminedisuccinic acid (EDDS) with Fe (III), Cu (II), Zn (II) and Mn (II) ions in aqueous solution. J. Chem. Soc. Dalton Trans., 2002, 4644–4648.
46. [46] Schneppensieper, T., Seibig, S., Zahl, A., Tregloan, P., van Eldik, R., Influence of chelate effects on the water-exchange mechanism of polyaminecarboxylate complexes of iron (III). Inorg. Chem. 40 (2001), 3670–3676.
47. [47] Rush, J., Koppenol, W., Reactions of iron (II) nitrilotriacetate and iron (II) ethylenediamine-N,N'-diacetate complexes with hydrogen peroxide. J. Am. Chem. Soc. 110 (1988), 4957–4963.
48. [48] Walling, C., Kurz, M., Schugar, H.J., Iron (III)-ethylenediaminetetraacetic acid-peroxide system. Inorg. Chem. 9 (1970), 931–937.
49. [49] Francis, K.C., Cummins, D., Oakes, J., Kinetic and structural investigations of [Fe III (edta)–edta = ethylenediaminetetra-acetate (4–)] catalysed decomposition of hydrogen peroxide. J. Chem. Soc. Dalton Trans., 1985, 493–501.
50. [50] Tachiev, G., Roth, J., Bowers, A., Kinetics of hydrogen peroxide decomposition with complexed and free iron catalysts. Int. J. Chem. Kinet 32 (2000), 24–35.
51. [51] von Sonntag, C., Dowideit, P., Fang, X., Mertens, R., Pan, X., Schuchmann, M.N., Schuchmann, H.-P., The fate of peroxyl radicals in aqueous solution. Water Sci. Technol. 35 (1997), 9–15.
52. [52] Colodette, J., Rothenberg, S., Dence, C., Factors affecting hydrogen peroxide stability in the brightening of mechanical and chemimechanical pulps. I: hydrogen peroxide stability in the absence of stabilizing systems. J. Pulp Pap. Sci. 14 (1988), J126–J132.
53. [53] Sillanpää, M.E., Kurniawan, T.A., Lo, W.-h, Degradation of chelating agents in aqueous solution using advanced oxidation process (AOP). Chemosphere 83 (2011), 1443–1460.
54. [54] Andrianirinaharivelo, S.L., Pilichowski, J.F., Bolte, M., Nitrilotriacetic acid transformation photo-induced by complexation with iron (III) in aqueous solution. Transition Met. Chem. 18 (1993), 37–41.
55. [55] Bucheli-Witschel, M., Egli, T., Environmental fate and microbial degradation of aminopolycarboxylic acids. FEMS Microbiol. Rev. 25 (2001), 69–106.
56. [56] Fabbricino, M., Ferraro, A., Del Giudice, G., d'Antonio, L., Current views on EDDS use for ex situ washing of potentially toxic metal contaminated soils. Rev. Environ. Sci Biotechnol. 12 (2013), 391–398.
57. 2. Me′ canismes re′ actionnels et mode′ lisation. New J. Chem. 22 (1998), 263–268.
58. [58] Rivas, F.J., Beltran, F.J., Frades, J., Buxeda, P., Oxidation of p-hydroxybenzoic acid by Fenton's reagent. Water Res. 35 (2001), 387–396.
59. [59] 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. 37 (2003), 2734–2742.
60. [60] Keenan, C.R., Sedlak, D.L., Ligand-enhanced reactive oxidant generation by nanoparticulate zero-valent iron and oxygen. Environ. Sci. Technol. 42 (2008), 6936–6941.
61. [61] 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. 42 (2008), 7424–7430.
62. [62] Pierre, J., Fontecave, M., Iron and activated oxygen species in biology: the basic chemistry. Biometals 12 (1999), 195–199.
63. − radicals in aqueous solution. J. Phys. Chem. Ref. Data 4 (1985), 1041–1100.
64. [64] Shimizu, K., Hutcheson, R., Engelmann, M.D., Cheng, I.F., Cyclic voltammetric and aqueous equilibria model study of the pH dependant iron (II/III) ethylenediamminetetraacetate complex reduction potential. J. Electroanal. Chem. 603 (2007), 44–50.
65. [65] Schalley, C.A., Analytical Methods in Supramolecular Chemistry. 2007, Wiley-VCH, Winheim,Gemany.
66. [66] Pourrezaei, P., Physico-Chemical Processes for Oil Sands Process-Affected Water Treatment. 2013, Department of Civil and Environmental Engineering, University of Alberta, Edmonton, AB.
67. [67] Madill, R.E., Orzechowski, M.T., Chen, G.S., Brownlee, B.G., Bunce, N.J., Preliminary risk assessment of the wet landscape option for reclamation of oil sands mine tailings: bioassays with mature fine tailings pore water. Environ. Toxicol. 16 (2001), 197–208.
68. [68] Mohamed, M.H., Wilson, L.D., Headley, J.V., Peru, K.M., Sequestration of naphthenic acids from aqueous solution using beta-cyclodextrin-based polyurethanes. Phys. Chem. Chem. Phys. 13 (2011), 1112–1122.
69. [69] Rogers, V.V., Liber, K., MacKinnon, M.D., Isolation and characterization of naphthenic acids from Athabasca oil sands tailings pond water. Chemosphere 48 (2002), 519–527.
70. [70] W.W. Hitchcock, J.M. Puckett, Odor Eliminating Solution, United States (2013).