Kinetics and mechanism of •oH mediated degradation of dimethyl phthalate in aqueous solution: Experimental and theoretical studies

Environmental Science and Technology

Volumn 48, Issue 1, 2014, Pages 641-648

  An, Taicheng ^a   Gao, Yanpeng ^a,b   Li, Guiying ^a   Kamat, Prashant V ^c,d   Peller, Julie ^e   Joyce, Michelle V ^d  

^a GUANGZHOU INSTITUTE OF GEOCHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^c UNIVERSITY OF NOTRE DAME   (United States)

^d UNIVERSITY OF NOTRE DAME   (United States)

^e INDIANA UNIVERSITY NORTHWEST   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADVANCED OXIDATION PROCESSES; BIMOLECULAR RATE CONSTANTS; COMPUTATIONAL ANALYSIS; COMPUTATIONAL RESULTS; ENVIRONMENTAL ENDOCRINE DISRUPTORS; HYDROGEN ATOM TRANSFERS (HAT); KINETICS AND MECHANISM; SINGLE ELECTRON TRANSFER;

ATOMS; ESTERS; POTASSIUM COMPOUNDS; RADIATION CHEMISTRY; RATE CONSTANTS; TRANSIENTS; WATER POLLUTION;

FREE RADICAL REACTIONS;

AZIDE; ENDOCRINE DISRUPTOR; HYDROGEN; HYDROXYL RADICAL; PHTHALIC ACID; PHTHALIC ACID DIMETHYL ESTER; MONOMETHYL PHTHALATE; PHTHALIC ACID DERIVATIVE; SOLUTION AND SOLUBILITY; WATER;

ABSORPTION; AQUEOUS SOLUTION; DEGRADATION; ENDOCRINE DISRUPTOR; EXPERIMENTAL STUDY; HYDROXYL RADICAL; ORGANIC POLLUTANT; PHTHALATE; REACTION KINETICS; THEORETICAL STUDY; WATER POLLUTION;

ABSORPTION; AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; DEGRADATION; DIELECTRIC CONSTANT; ELECTRON TRANSPORT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IRRADIATION; OXIDATION REDUCTION POTENTIAL; PULSE RADIOLYSIS; RADIOLYSIS; REACTION ANALYSIS; REACTION TIME; TOTAL ORGANIC CARBON; WATER MANAGEMENT; CHEMISTRY; KINETICS; OXIDATION REDUCTION REACTION; PH; QUANTUM THEORY; SOLUTION AND SOLUBILITY; THEORETICAL MODEL;

ELECTRON TRANSPORT; HYDROGEN; HYDROGEN-ION CONCENTRATION; HYDROXYL RADICAL; KINETICS; MODELS, THEORETICAL; OXIDATION-REDUCTION; PHTHALIC ACIDS; QUANTUM THEORY; SOLUTIONS; WATER;

EID: 84891797008     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es404453v     Document Type: Article

References (53)

1. An, T. C.; Yang, H.; Li, G. Y.; Song, W. H.; Cooper, W. J.; Nie, X. P. Kinetics and mechanism of advanced oxidation processes (AOPs) in degradation of ciprofloxacin in water Appl. Catal. B-Environ. 2010, 94 (3-4) 288-294 10.1016/j.apcatb.2009.12.002
2. Bajt, O.; Mailhot, G.; Bolte, M. Degradation of dibutyl phthalate by homogeneous photocatalysis with Fe(III) in aqueous solution Appl. Catal. B-Environ. 2001, 33 (3) 239-248 10.1016/S0926-3373(01)00179-5
3. 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) 1-84 10.1080/10643380500326564
4. Konsowa, A. H.; Ossman, M. E.; Chen, Y. S.; Crittenden, J. C. Decolorization of industrial wastewater by ozonation followed by adsorption on activated carbon J. Hazard. Mater. 2010, 176 (1-3) 181-185 10.1016/j.jhazmat. 2009.11.010
5. Zhang, W. B.; An, T. C.; Xiao, X. M.; Fu, J. M.; Sheng, G. Y.; Cui, M. C. Photochemical degradation performance of quinoline aqueous solution in the presence of hydrogen peroxide J. Environ. Sci. Health, Part A: Toxic/Hazard. Subst. Environ. Eng. 2003, 38 (11) 2599-2611 10.1081/Ese-120024442
6. Wu, M. H.; Liu, N.; Xu, G.; Ma, J.; Tang, L. A.; Wang, L. A.; Fu, H. Y. Kinetics and mechanisms studies on dimethyl phthalate degradation in aqueous solutions by pulse radiolysis and electron beam radiolysis Radiat. Phys. Chem. 2011, 80 (3) 420-425 10.1016/j.radphyschem.2010.10.008
7. 2: A case of sulfa drugs Catal. Today 2010, 153 (3-4) 200-207 10.1016/j.cattod.2010.02.068
8. Zhang, S. J.; Jiang, H.; Li, M. J.; Yu, H. Q.; Yin, H.; Li, Q. R. Kinetics and mechanisms of radiolytic degradation of nitrobenzene in aqueous solutions Environ. Sci. Technol. 2007, 41 (6) 1977-1982 10.1021/Es062031l
9. An, T. C. Persistent organic pollutants in water and wastewater and their treatment by advanced oxidation processes Res. J. Chem. Environ. 2007, 11 (4) 3-4
10. Sun, W. J.; Yang, L. M.; Yu, L. Y.; Saeys, M. Ab initio reaction path analysis for the initial hydrogen abstraction from organic acids by hydroxyl radicals J. Phys. Chem. A 2009, 113 (27) 7852-7860 10.1021/Jp8090792
11. Zhang, Q. Z.; Qu, X. H.; Wang, H.; Xu, F.; Shi, X. Y.; Wang, W. X. Mechanism and thermal rate constants for the complete series reactions of chlorophenols with H Environ. Sci. Technol. 2009, 43 (11) 4105-4112 10.1021/Es9001778
12. 2 and risk assessment of its degradation products Environ. Sci. Technol. 2013, 47 (6) 2704-2712 10.1021/Es304898r
13. Chang, P. B. L.; Young, T. M. Kinetics of methyl tert -butyl ether degradation and by-product formation during UV/hydrogen peroxide water treatment Water Res. 2000, 34 (8) 2233-2240 10.1016/S0043-1354(99)00392-9
14. Wardman, P. Reduction potentials of one-electron couples involving free-radicals in aqueous-solution J. Phys. Chem. Ref. Data 1989, 18 (4) 1637-1755
15. Naik, G. H.; Priyadarsini, K. I.; Maity, A. K.; Mohan, H. One electron oxidation induced dimerization of 5-hydroxytryptophol: Role of 5-hydroxy substitution J. Phys. Chem. A 2005, 109 (10) 2062-2068 10.1021/Jp048157r
16. Galano, A.; Alvarez-Idaboy, J. R. Guanosine plus OH radical reaction in aqueous solution: A reinterpretation of the UV-vis data based on thermodynamic and kinetic calculation Org. Lett. 2009, 11 (22) 5114-5117 10.1021/Ol901862h
17. Mohan, H.; Mittal, J. P. Pulse radiolysis investigations on acidic aqueous solutions of benzene: Formation of radical cations J. Phys. Chem. A 1999, 103 (3) 379-383 10.1021/Jp983255w
18. Geeta, S.; Rao, B. S. M.; Mohan, H.; Mittal, J. P. Radiation-induced oxidation of substituted benzaidehydes: A pulse radiolysis study J. Phys. Org. Chem. 2004, 17 (3) 194-198 10.1002/poc.713
19. Nicolaescu, A. R.; Wiest, O.; Kamat, P. V. Radical-induced oxidative transformation of quinoline J. Phys. Chem. A 2003, 107 (3) 427-433 10.1021/jp027112s
20. Mezyk, S. P.; Neubauer, T. J.; Cooper, W. J.; Peller, J. R. Free-radical-induced oxidative and reductive degradation of sulfa drugs in water: Absolute kinetics and efficiencies of hydroxyl radical and hydrated electron reactions J. Phys. Chem. A 2007, 111 (37) 9019-9024 10.1021/jp073990k
21. Sehested, K.; Christensen, H. C.; Hart, E. J.; Corfitzen, H. Rates of reaction of O-, OH, and H with methylated benzenes in aqueous solution-optical-spectra of radicals J. Phys. Chem. 1975, 79 (4) 310-315 10.1021/j100571a005
22. Song, W. H.; Xu, T. L.; Cooper, W. J.; Dionysiou, D. D.; De La Cruz, A. A.; O'Shea, K. E. Radiolysis studies on the destruction of microcystin-LR in aqueous solution by hydroxyl radicals Environ. Sci. Technol. 2009, 43 (5) 1487-1492 10.1021/es802282n
23. Alam, M. S.; Rao, B. S. M.; Mohan, H.; Mittal, J. P. Study of radiation chemical reactions of oxidising and reducing radicals with furazan derivatives J. Photochem. Photobiol., A 2001, 143 (2-3) 181-189 10.1016/S1010-6030(01)00529- 9
24. Rao, P. S.; Hayon, E. Oxidation of aromatic-amines and diamines by OH radicals-Formation and ionization-constants of amine cation radicals in water J. Phys. Chem. 1975, 79 (11) 1063-1066 10.1021/j100578a005
25. Tripathi, G. N. R. Electron-transfer component in hydroxyl radical reactions observed by time resolved resonance Raman spectroscopy J. Am. Chem. Soc. 1998, 120 (17) 4161-4166 10.1021/Ja9800838
26. Tripathi, G. N. R.; Sun, Q. Time-resolved Raman study of the oxidation mechanism of aromatic diamines by (OH)-O-center dot radical in water J. Phys. Chem. A 1999, 103 (45) 9055-9060 10.1021/Jp9927552
27. Minakata, D.; Crittenden, J. Linear free energy relationships between aqueous phase hydroxyl radical reaction rate constants and free energy of activation Environ. Sci. Technol. 2011, 45 (8) 3479-3486 10.1021/Es1020313
28. Minakata, D.; Song, W. H.; Crittenden, J. Reactivity of aqueous phase hydroxyl radical with halogenated carboxylate anions: Experimental and theoretical studies Environ. Sci. Technol. 2011, 45 (14) 6057-6065 10.1021/Es200978f
29. Nicolaescu, A. R.; Wiest, O.; Kamat, P. V. Mechanistic pathways of the hydroxyl radical reactions of quinoline. 2. Computational analysis of hydroxyl radical attack at C atoms J. Phys. Chem. A 2005, 109 (12) 2829-2835 10.1021/jp045016g
30. Giam, C. S.; Chan, H. S.; Neff, G. S.; Atlas, E. L. Phthalate ester plasticizers-New class of marine pollutant Science 1978, 199 (4327) 419-421 10.1126/science.199.4327.419-a
31. Koniecki, D.; Wang, R.; Moody, R. P.; Zhu, J. P. Phthalates in cosmetic and personal care products: Concentrations and possible dermal exposure Environ. Res. 2011, 111 (3) 329-336 10.1016/j.envres.2011.01.013
32. Buxton, G. V.; Stuart, C. R. Reevaluation of the thiocyanate dosimeter for pulse-radiolysis J. Chem. Soc., Faraday Trans. 1995, 91 (2) 279-281 10.1039/Ft9959100279
33. -) in aqueous-solution J. Phys. Chem. Ref. Data 1988, 17 (2) 513-886
34. Song, W.; Cooper, W. J.; Mezyk, S. P.; Greaves, J.; Peake, B. M. Free radical destruction of beta-blockers in aqueous solution Environ. Sci. Technol. 2008, 42 (4) 1256-1261 10.1021/Es702245n
35. Frisch, M. J.; Truck, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, J. R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Boboul, A. G.; Stefnov, B. B.; Liu, G.; Liaschenko, A.; Piskorz, P.; Komaromi, L.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 03; Guassian, Inc.: Pittsburgh, PA, 2003.
36. Barone, V.; Cossi, M. Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model J. Phys. Chem. A 1998, 102 (11) 1995-2001 10.1021/jp9716997
37. Tomasi, J.; Mennucci, B.; Cammi, R. Quantum mechanical continuum solvation models Chem. Rev. 2005, 105 (8) 2999-3093 10.1021/Cr9904009
38. 2 heterogeneous catalysis J. Phys. Chem. A 2010, 114 (7) 2569-2575 10.1021/Jp911349y
39. Steenken, S.; Ramaraj, R. Comparison of reactions of radical cations of 1-phenylalkanols produced by photoionization and by one-electron oxidation in aqueous solution J. Chem. Soc., Perkin Trans. 2001, 9, 1613-1619 10.1039/B102515p
40. Mezyk, S. P.; Jones, J.; Cooper, W. J.; Tobien, T.; Nickelsen, M. G.; Adams, J. W.; O'Shea, K. E.; Bartels, D. M.; Wishart, J. F.; Tornatore, P. M.; Newman, K. S.; Gregoire, K.; Weidman, D. J. Radiation chemistry of methyl tert -butyl ether in aqueous solution Environ. Sci. Technol. 2004, 38 (14) 3994-4001 10.1021/es034558t
41. 2 J. Hazard. Mater. 2011, 195, 371-377 10.1016/j.jhazmat.2011.08.054
42. 2 process J. Hazard. Mater. 2009, 162 (2-3) 954-959 10.1016/j.jhazmat.2008.05.122
43. Alfassi, Z. B.; Prutz, W. A.; Schuler, R. H. Intermediates in the oxidation of azide ion in acidic solutions J. Phys. Chem. 1986, 90 (6) 1198-1203 10.1021/J100278a047
44. Hayon, E.; Simic, M. Absorption spectra and kinetics of the intermediate produced from the decay of azide radicals J. Am. Chem. Soc. 1970, 92 (25) 7486-7487 10.1021/ja00728a049
45. Alfassi, Z. B.; Schuler, R. H. Reaction of azide radicals with aromatic compounds. Azide as a selective oxidant J. Phys. Chem. 1985, 89 (15) 3359-3363 10.1021/j100261a040
46. Ram, M. S.; Stanbury, D. M. Reduction potential of the trinitrogen radical as determined by chemical-kinetics-Novel application of spin trapping Inorg. Chem. 1985, 24 (25) 4233-4234 10.1021/Ic00219a004
47. Huie, R. E.; Clifton, C. L.; Neta, P. Electron-transfer reaction-rates and equilibria of the carbonate and sulfate radical-anions Radiat. Phys. Chem. 1991, 38 (5) 477-481
48. Neta, P.; Madhavan, V.; Zemel, H.; Fessenden, R. W. Rate constants and mechanism of reaction of sulfate radical anion with aromatic compounds J. Am. Chem. Soc. 1977, 99 (1) 163-164 10.1021/ja00443a030
49. Zemel, H.; Fessenden, R. W. The mechanism of reaction of sulfate radical anion with some derivatives of benzoic acid J. Phys. Chem. 1978, 82 (25) 2670-2676 10.1021/j100514a008
50. Al-Sheikhly, M.; Poster, D. L.; An, J. C.; Neta, P.; Silverman, J.; Huie, R. E. Ionizing radiation-induced destruction of benzene and dienes in aqueous media Environ. Sci. Technol. 2006, 40 (9) 3082-3088 10.1021/es052533j
51. An, T. C.; Li, G. Y.; Zhu, X. H.; Fu, J. M.; Sheng, G. Y.; Zhu, Z. Photoelectrocatalytic degradation of oxalic acid in aqueous phase with a novel three-dimensional electrode-hollow quartz tube photoelectrocatalytic reactor Appl. Catal., A 2005, 279 (1-2) 247-256 10.1016/j.apcata.2004.10.033
52. Duesteberg, 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 (11) 4103-4110 10.1021/es0628699
53. Kusu, R.; Toda, C.; Okamoto, Y.; Tozuka, Y.; Ueda, K.; Kojima, N. Structural properties of estrogen receptor ligand obtained by study of hydroxylated phthalate ester derivatives Environ. Toxicol. Pharmacol. 2007, 24 (3) 311-315 10.1016/j.etap.2007.08.002