|
|
Fenton oxidation of 2,4- and 2,6-dinitrotoluene
and acetone inhibition |
HE Yiliang1, ZHAO Bin1, HUGHES Joseph B.2, HAN Sung Soo2 |
1.School of Environmental Science and Engineering, Shanghai Jiao Tong University; 2.School of Civil and Environmental Engineering, Georgia Institute of Technology |
|
|
Abstract The performances and kinetic parameters of Fenton oxidation of 2,4- and 2,6-dinitrotoluene (DNT) in water-acetone mixtures and explosive contaminated soil washing-out solutions were investigated at a laboratory scale. The experimental results show that acetone can be a significant hydroxyl radical scavenger and result in serious inhibition of Fenton oxidation of 2,4- and 2,6-DNT. Although no serious inhibition was found in contaminated soil washing-out solutions, longer reaction time was needed to remove 2,4- and 2,6-DNT completely, mainly due to the competition of hydroxyl radicals. Fenton oxidation of 2,4- and 2,6-DNT fit well with the first-order kinetics and the presence of acetone also reduced DNT’s degradation kinetics. Based on the comparison and matching of retention time and ultraviolet (UV) spectra between high performance liquid chromatography (HPLC) and standards, the following reaction pathway for 2,4-DNT primary degradation was proposed: 2,4-DNT → 2,4-dinitro-benzaldehyde → 2,4-dinitrobenzoic acid → 1,3-dinitrobenzene → 3-nitrophenol.
|
Issue Date: 05 September 2008
|
|
1 |
Spain J C, Hughes J B, Knackmuss H J . Biodegradation of Nitroaromatic Compounds and Explosives. Boca Raton, Florida, USA: Lewis Publishers, 2000, 1–6
|
2 |
Rickert D E . Toxicity of Nitroaromatic Compounds. Washington, DC, USA: HemispherePublishing Corp, 1985, 53
|
3 |
Rodgers J, Bunce N . Treatment methods for theremoval of nitroromatic explosive. WaterResearch, 2001, 35: 2101–2111. doi:10.1016/S0043‐1354(00)00505‐4
|
4 |
Venkatadri R, Peters R W . Chemical oxidation technologies:Ultraviolet light/hydrogen peroxide, Fenton's reagent, and titaniumdioxide-assisted photocatalysis. Hazard. Waste Hazard. Mater., 1993, 10(2): 107–149
|
5 |
Mohanty N R, Wei I W . Oxidation of 2,4-dinitrotolueneusing Fenton's reagent: Reaction mechanisms and their practical applications.Hazard. Waste Hazard. Mater., 1993, 10: 171–183
|
6 |
Li Z, Shea P, Comfort S . Nitrotoluene destruction by UV-catalyzed Fenton oxidation. Chemosphere, 1998, 36(8): 1849–1865. doi:10.1016/S0045‐6535(97)10073‐X
|
7 |
Celin S M, Pandit M, Kapoor J C, Sharma R K . Studies onphoto-degradation of 2,4-dinitro toluene in aqueous phase. Chemosphere, 2003, 53(1): 63–69. doi:10.1016/S0045‐6535(03)00358‐8
|
8 |
Ho P C . Photooxidation of 2,4-dinitrotoluene in aqueous solution in the presenceof hydrogen peroxide. Environ. Sci. Technol., 1986, 20: 260–267. doi:10.1021/es00145a007
|
9 |
Larson R A, Jafvert C T, Bosca F, Marley K A, Miller P L . Effects of surfactants on reduction andphotolysis (> 290 nm) of nitroaromatic compounds. Environ. Sci. & Technol., 2000, 34: 505–508. doi:10.1021/es990891e
|
10 |
Chen W S, Juan C N, Wei K M . Mineralization of dinitrotoluenes and trinitrotolueneof spent acid in toluene nitration process by Fenton oxidation. Chemosphere, 2005, 60(8): 1072–1079. doi:10.1016/j.chemosphere.2005.01.021
|
11 |
Yardin G, Chiron S . Photo-Fenton treatment ofTNT contaminated soil extract solutions obtained by soil flushingwith cyclodextrin. Chemosphere, 2006, 62: 1395–1402. doi:10.1016/j.chemosphere.2005.05.019
|
12 |
Liou M, Lu M, Chen J . Oxidation of TNT by Photo-Fenton process. Chemosphere, 2004, 57: 1107–1114. doi:10.1016/j.chemosphere.2004.07.053
|
13 |
Kulik N, Goi A, Trapido M, Tuhkanen T . Degradationof polycyclic aromatic hydrocarbons by combined chemical pre-oxidationand bioremediation in creosote contaminated soil. Journal of Environmental Management, 2006, 78: 382–391. doi:10.1016/j.jenvman.2005.05.005
|
14 |
Goi A, Trapido M . Degradation of polycyclicaromatic hydrocarbons in soil: The Fenton reagent versus ozonation. Eviron. Technol., 2004, 25: 155–164
|
15 |
Kang N, Hua I . Enhanced chemical oxidationof aromatic hydrocarbons in soil systems. Chemosphere, 2005, 61: 909–922. doi:10.1016/j.chemosphere.2005.03.039
|
16 |
Beltran F J, Encinar J M, Alonso M A . Nitroaromatic hydrocarbon ozonation in water: 1. Singleozonation. Ind. Engng. Chem. Res., 1998, 37: 25–31. doi:10.1021/ie9704253
|
17 |
Lindsey M E, Tarr M A . Inhibition of hydroxyl radicalreaction with aromatics by dissolved natural organic matter. Environ. Sci. & Technol., 2000, 34(3): 444–449. doi:10.1021/es990457c
|
18 |
Stefan M I, Hoy A R, Bolton J R . Kinetics and mechanism of the degradation and mineralizationof acetone in dilute aqueous solution sensitized by UV photolysisof hydrogen peroxide. Environ. Sci. &Technol., 1996, 30: 2382–2390. doi:10.1021/es950866i
|
19 |
Stefan M I, Hoy A R, Bolton J R . Reinvestigation of the acetone degradation mechanismin dilute aqueous solution by the UV/H2O2 process. Environ. Sci. &Technol, 1999, 33: 870–873. doi:10.1021/es9808548
|
20 |
American Pubic HealthAssociateion (APHA), American Water Works Association, and Water PollutionControl Federation. . Standard Methods for Examination of Waterand Wastewater. 20th ed.Washington DC, USA: American PublicHealth Association, 1998
|
21 |
Sulzberger B, Suter D, Siffert C, Stumn W . Dissolutionof Fe(Ш) (hydr)oxides in natural waters; Laboratory assessmenton the kinetics controlled by surface coordination. Marine Chemistry, 1989, 28: 127–144. doi:10.1016/0304‐4203(89)90191‐6
|
22 |
Buxton G V, Greenstock C L, Helman W P, Ross A B . Criticalreview of rate constants for reactions of hydrated electrons, hydrogenatoms, and hydroxyl radicals (⋅OH/⋅O-) in aqueous solution. Journal of PhysicalChemistry Reference Data, 1988, 17: 513–886
|
|
Viewed |
|
|
|
Full text
|
|
|
|
|
Abstract
|
|
|
|
|
Cited |
|
|
|
|
|
Shared |
|
|
|
|
|
Discussed |
|
|
|
|