Abstract
The photocatalytic degradation of isoproturon, a persistent toxic herbicide, was investigated in the presence of natural iron oxide and oxalic acid and under UV irradiation. The influence of the relevant parameters such as the pH and the iron oxide and oxalic acid concentrations has been studied. The presence of natural iron oxide and oxalic acid in the system effectively allow the degradation of isoproturon, whereas the presence of t-butyl alcohol adversely affects the phototransformation of the target pollutant, thus indicating that an OH radical initiated the degradation mechanism. The degradation mechanism of isoproturon was investigated by means of GC-MS analysis. Oxidation of both the terminal N-(CH3)2 and isopropyl groups is the initial process leading to N-monodemethylated (NHCH3), N-formyl (N(CH3)CHO), and CHCH3OH as the main intermediates. The substitution of the isopropyl group by an OH group is also observed as a side process
Similar content being viewed by others
References
S. von Wiren-Lehr, M. del Pilar Castillo, L. Torstensson and I. Scheunert, Degradation of isoproturon in biobeds, Biol. Fertil. Soils, 2001, 33, 535–540.
S. Parra, V. Sarria, S. Malato, P. Peringer and C. Pulgarin, Photochemical versus coupled photochemical-biological flow system for the treatment of two biorecalcitrant herbicides: metobromuron and isoproturon, Appl. Catal, B, 2000, 27, 153–168.
H. Allemane, M. Prados-Ramirez, J. P. Croue and B. Legube, Recherche et identification des premiers sous-produits d’oxydation de I’isoproturon par le systeme ozone/ peroxyde d’hydrogene, Rev. Sci Eau/J. Water Sci., 1995, 8, 315–331.
B. M. Magdalena, S. Ilie and L. Elsa, Photodegradation of Isoproturon in Water by Several Adavanced Oxidation Processes, Chem. Bull., 2005, 50, 1–2.
S. Sanches, M. T. B. Crespo and V. J. Pereira, Drinking water treatment of priority pesticides using low pressure UV. photolysis and advanced oxidation processes, Water Res., 2010, 44, 1809–1818.
Y. C. Lu, S. Zhang and H. Yang, Acceleration of the herbicide isoproturon degradation in wheat by glycosyltransferases and salicylic acid, J. Hazard. Mater., 2015, 283, 806–814.
M. P. Sharma, V. D. Kumari and M. Subrahmanyam, Photocatalytic degradation of isoproturon herbicide over TiO2/Al-MCM-41 composite systems using solar light, Chemosphere, 2008, 72, 644–651.
M. V. Phanikrishna Sharma, K. Lalitha, V. Durgakumari and M. Subrahmanyam, Solar photocatalytic mineralization of isoproturon over TiO2/HY. composite systems, Sol. Energy Mater. Sol. Cells, 2008, 92, 332–342.
S. Malato, P. Fernández-Ibanez, M. I. Maldonado, J. Blanco and W. Gernjak, Decontamination and disinfection of water by solar photocatalysis: recent overview and trends, Catal. Today, 2009, 147, 1–59.
S. Thomas, A. Alatrache, M.-N. Pons and O. Zahraa, Degradation of the herbicide isoproturon by a photocatalytic process, C. R. Chim., 2014, 17, 824–831.
M. Lopez-Munoz, A. Revilla and J. Aguado, Heterogeneous photocatalytic degradation of isoproturon in aqueous solution: Experimental design and intermediate products analysis, Catal. Today, 2013, 209, 99–107.
R. Xie, L. Zhang, H. Xu, Y. Zhong, X. Sui and Z. Mao, Fabrication of Z-scheme photocatalyst Ag-AgBr@ Bi20 TiO32 and its visible-light photocatalytic activity for the degradation of isoproturon herbicide, J. Mol. Catal. A: Chem., 2015, 406, 194–203.
P. Garcia-Munoz, J. Carbajo, M. Faraldos and A. Bahamonde, Photocatalytic degradation of phenol and isoproturon: effect of adding an activated carbon to titania catalyst, J. Photochem. Photobiol, A, 2014, 287, 8–18.
A. Verma, N. Prakash and A. Toor, An efficient Ti02 coated immobilized system for the degradation studies of herbicide isoproturon: Durability studies, Chemosphere, 2014, 109, 7–13.
A. K. R. Police, S. Basavaraju, D. K. Valluri and S. Machiraju, Bismuth modified porous silica preparation, characterization and photocatalytic activity evaluation for degradation of isoproturon, J. Mater. Sci Technol, 2013, 29, 639–646.
H. Gupta and B. Gupta, Photocatalytic degradation of poly-cyclic aromatic hydrocarbon benzo [a] pyrene by iron oxides and identification of degradation products, Chemosphere, 2015, 138, 924–931.
V. M. da Silva Rocha, M. de Godoi Pereira, L. R. Teles and M. O. da Guarda Souza, Effect of copper on the photocatalytic activity of semiconductor-based titanium dioxide (anatase) and hematite (α-Fe2O3), Mater. Sci Eng., B, 2014, 185, 13–20.
M. Mahadik, S. Shinde, V. Mohite, S. Kumbhar, K. Rajpure, A. Moholkar, et al, Photoelectrocatalytic oxidation of Rhodamine B. with sprayed α-Fe2O3 photocatalyst, Mater. Express, 2013, 3, 247–255.
C. Liu, F. Li, X. Li, G. Zhang and Y. Kuang, The effect of iron oxides and oxalate on the photodegradation of 2-mercapto-benzothiazole, J. Mol. Catal. A: Chem., 2006, 252, 40–48.
S. Belaidi, T. Sehili, L. Mammeri and K. Djebbar, Photodegradation kinetics of 2, 6-dimetyIphenol by natural iron oxide and oxalate in aqueous solution, J. Photochem. Photobiol., A, 2012, 237, 31–37.
L. Mammeri, T. Sehili, S. Belaidi and K. Djebbar, Heterogeneous photodegradation of 1-naphthol with natural iron oxide in water: influence of oxalic acid, Desalin. Water Treat, 2015, 54, 2324–2333.
J. Dhal, B. Mishra and G. Hota, Ferrous oxalate, maghemite and hematite nanorods as efficient adsorbents for decontamination of Congo red dye from aqueous system, Int. J. Environ. Sci. Technol, 2015, 12, 1845–1856.
C. Weller, S. Horn and H. Herrmann, Photolysis of Fe(III) carboxylato complexes: Fe(II) quantum yields and reaction mechanisms, J. Photochem. PhotobioL, A, 2013, 268, 24–36.
V. Balzani and V. Carassiti, Photochemistry of Coordination Compounds, Academic Press, London, 1970, ch. 10, pp. 145–192.
M. E. Balmer and B. Sulzberger, Atrazine degradation in irradiated iron/oxalate systems: effects of pH. and oxalate, Environ. Set TechnoL, 1999, 33, 2418–2424.
T. Weber, T. Allard, E. Tipping and M. F. Benedetti, Modeling iron binding to organic matter, Environ. Sci. TechnoL, 2006, 40, 7488–7493.
H. Gao and R. G. Zepp, Factors influencing photoreactions of dissolved organic matter in a coastal river of the southeastern United States, Environ. Sci. TechnoL, 1998, 32, 2940–2946.
B. C. Faust and R. G. Zepp, Photochemistry of aqueous iron(III)-poIycarboxyIate complexes: roles in the chemistry of atmospheric and surface waters, Environ. Sci. Technol, 1993, 27, 2517–2522.
C. Siffert and B. Sulzberger, Light-induced dissolution of hematite in the presence of oxalate. A. case study, Langmuir, 1991, 7, 1627–1634.
V. Amin and N. Olson, Spectrophotometric Determination of Hydrogen Peroxide in Milkl, J. Dairy Sci., 1967, 50, 461–464.
B. Sulzberger and H. Laubscher, Reactivity of various types of iron(III)(hydr) oxides towards light-induced dissolution, Mar. Chem., 1995, 50, 103–115.
Q. Lan, H. Liu, F.-b. Li, F. Zeng and C.-s. Liu, Effect of pH. on pentachlorophenol degradation in irradiated iron/ oxalate systems, Chem. Eng.J., 2011, 168, 1209–1216.
F. Li, X. Li, X. Li, T. Liu and J. Dong, Heterogeneous photodegradation of bisphenol A. with iron oxides and oxalate in aqueous solution, J. Colloid Interface Sci., 2007, 311, 481–490.
J. Fenoll, P. Sabater, G. Navarro, G. Perez-Lucas and S. Navarro, Photocatalytic transformation of sixteen substituted phenylurea herbicides in aqueous semiconductor suspensions: intermediates and degradation pathways, J. Hazard. Mater., 2013, 244, 370–379.
H. Boucheloukh, T. Sehili, N. Kouachi and K. Djebbar, Kinetic and analytical study of the photo-induced degradation of monuron by nitrates and nitrites under irradiation or in the dark, Photochem. Photobiol Sci., 2012, 11, 1339–1345.
M. Bobu, S. Wilson, T. Greibrokk, E. Lundanes and I. Siminiceanu, Comparison of advanced oxidation processes and identification of monuron photodegradation products in aqueous solution, Chemosphere, 2006, 63, 1718–1727.
M. Shankar, S. Nelieu, L. Kerhoas and J. Einhorn, Photo-induced degradation of diuron in aqueous solution by nitrites and nitrates: kinetics and pathways, Chemosphere, 2007, 66, 767–774.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Boucheloukh, H., Remache, W., Parrino, F. et al. The effect of natural iron oxide and oxalic acid on the photocatalytic degradation of isoproturon: a kinetics and analytical study. Photochem Photobiol Sci 16, 759–765 (2017). https://doi.org/10.1039/c6pp00441e
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1039/c6pp00441e