Abstract
The photocatalytic degradation of di-(2-ethylhexyl) phthalate (DEHP) in solution using titanium dioxide (TiO2) was analyzed in this study. It was found that DEHP was completely removed in the solution after 150 min irradiation. The effect of different factors, such as photocatalyst amount, DEHP concentration, light intensity, pH, and temperature on photocatalytic degradation was investigated. The degradation mechanism of DEHP with proton and hydroxyl radicals oxidation were also studied. It is suggested that either ethylhexyl or ester chain scissions of the aliphatic part of DEHP was the dominant degradation mechanism of the process. The photocatalytic degradation process was well described by first-order reaction. The final mineralization product was carbon dioxide and the intermediate products were identified by GC-MS. Thus, the photocatalytic degradation treatment of DEHP in wastewater is a relative simple and fast method.
Similar content being viewed by others
References
Adhoum, N., & Monser, L. (2004). Removal of phthalate on modified activated carbon: application to the treatment of industrial wastewater. Separation and Purification Technology, 38, 233–239. doi:10.1016/j.seppur.2003.11.011.
Bajt, O., Maihot, G., & Bolte, M. (2001). Degradation of dibutyl phthalate by homogeneous photocatalysis with Fe III in aqueous solution. Applied Catalysis B Environmental, 33, 239–248. doi:10.1016/S0926-3373(01)00179-5.
Balabanovich, A. I., & Schnabel, W. (1998). On the photolysis of phthalic acid dimethyl and diethyl ester: a product analysis study. Journal of Photochemistry and Photobiology A: Chemistry, 113, 145–153.
Bodzek, M., Dudziak, M., & Luks-Betlej, K. (2004). Application of membrane techniques to water purification. Removal of phthalates. Desalination, 162, 121–128. doi:10.1016/S0011-9164(04)00035-9.
Chan, C. M., Wong, K. H., Chung, W. K., Chow, T. S., & Wong, P. K. (2007). Photocatalytic degradation of di(2-ethylhexyl) phthalate adsorbed by chitin A. Water Science and Technology, 56, 125–134. doi:10.2166/wst.2007.685.
Chang, B. V., Liao, C. S., & Yuan, S. Y. (2005). Aerobic degradation of diethyl phthalate, di-n-butyl phthalate and di-(2-ethylhexyl) phthalate from river sediment in Taiwan. Chemosphere,58, 1601–1607. doi:10.1016/j.chemosphere.2004.11.031.
Chen, C. Y. (2004). Biosynthesis of di-(2-ethylhexyl) phthalate (DEHP) and di-n-butyl phthalate (DBP) from red alga-Bangia atropurpurea. Water Research, 38, 1014–1018. doi:10.1016/j.watres.2003.11.029.
Chen, C. Y., Chen, C. C., & Chung, Y. C. (2007). Removal of phthalate esters by α-cyclodextrin-linked chitosan bead. Bioresource Technology, 98, 2578–2583. doi:10.1016/j.biortech.2006.09.009.
Chiou, C. S., Shie, J. L., Chang, C. Y., Liu, C. C., & Chang, C. T. (2006). Degradation of di-n-butyl phthalate using photoreactor packed with TiO2 immobilized on glass beads. Journal of Hazardous Materials, B137, 1123–1129. doi:10.1016/j.jhazmat.2006.03.058.
Chu, W., & Jafvert, C. T. (1994). Photodechlorination of polychlorobenzene congeners in surfactant micelle solutions. Environmental Science & Technology, 28, 2415–2422. doi:10.1021/es00062a029.
Ejlertsson, J., Alnervik, M., Jonsson, S., & Svensson, B. H. (1997). Influence of water solubility, side-chain degradability, and side-chain structure on the degradation of phthalic acid esters under methanogenic conditions. Environmental Science & Technology, 31, 2761–2764. doi:10.1021/es961055x.
Hustert, K., & Moza, P. N. (1988). Photocatalytic degradation of phthalates using titanium dioxide in aqueous solution. Chemosphere, 17, 1751–1754. doi:10.1016/0045-6535(88)90103-8.
Jaegar, C. D., & Bard, A. J. (1979). Spin trapping and electron spin resonance detection of radical intermediates in the photodecomposition of water at TiO2 particulate system. Journal of Physical Chemistry, 83, 3146–3152. doi:10.1021/j100487a017.
Jianlong, W., Lujun, C., Hanchang, S., & Yi, Q. (2000). Microbial degradation of phthalic acid esters under anaerobic digestion of sludge. Chemosphere, 41, 1245–1248. doi:10.1016/S0045-6535(99)00552-4.
Kaneco, S., Katsumata, H., Suzuki, T., & Ohta, K. (2006). Titanium dioxide mediated photocatalytic degradation of dibutyl phthalate in aqueous solution-kinetics, mineralization and reaction mechanism. Chemical Engineering Journal, 125, 59–66. doi:10.1016/j.cej.2006.08.004.
Kim, T. S., Kim, J. K., Choi, K., Stenstrom, M. K., & Zoh, K. D. (2006). Degradation mechanism and the toxicity assessment in TiO2 photocatalysis and photolysis of parathion. Chemosphere, 62, 926–933. doi:10.1016/j.chemosphere.2005.05.038.
Ku, Y., Hyng, J. J., & Wang, W. Y. (2006). Decomposition of 2-nitrophenol in aqueous solution by ozone and UV/Ozone processes. Water Environment Research, 78, 901–908. doi:10.2175/106143005X78672.
Lau, T. K., Chu, W., & Graham, N. (2005). The degradation of endocrine disruptor di-n-butyl phthalate by UV irradiation: a photolysis and product study. Chemosphere, 60, 1045–1053. doi:10.1016/j.chemosphere.2005.01.022.
Lin, H. F., & Valsaraj, K. T. (2003). A titania thin film annular photocatalytic reactor for the degradation of polycyclic aromatic hydrocarbons in dilute water streams. Journal of Hazardous Materials, B99, 203–219. doi:10.1016/S0304-3894(03)00060-8.
Ogunfowokan, A. O., Torto, N., Adenuga, A. A., & Okoh, E. K. (2006). Survey of levels of phthalate ester plasticizers in a sewage lagoon effluent and a receiving stream. Environmental Monitoring and Assessment, 118, 457–480. doi:10.1007/s10661-006-1500-z.
Perez-Prieto, J., Bosca, F., Galian, R. E., Lahoz, A., Domingo, L. R., & Miranda, M. A. (2003). Photoreaction between 2-benzoylthiophene and phenol or indole. The Journal of Organic Chemistry, 68, 5104–5113. doi:10.1021/jo034225e.
Psillakis, E., Mantzavinos, D., & Kalogerakis, N. (2004). Monitoring the sonochemical degradation of phthalate esters in water using solid-phase microextraction. Chemosphere, 54, 849–857. doi:10.1016/j.chemosphere.2003.09.039.
Roslev, P., Vorkamp, K., Aarup, J., Frederiksen, K., & Nielsen, P. H. (2007). Degradation of phthalate esters in an activated sludge wastewater treatment plant. Water Research, 41, 969–976. doi:10.1016/j.watres.2006.11.049.
Staples, C. A., Adams, W. J., Parkerton, T. F., Gorsuch, J. W., Biddinger, G. R., & Reinert, K. H. (1997b). Aquatic toxicology of eighteen phthalate esters. Environmental Toxicology and Chemistry, 16, 875–891. doi:10.1897/1551-5028(1997)016<0875:ATOEPE>2.3.CO;2.
Staples, C. A., Peterson, D. R., & Parkerton, T. F. (1997a). The environmental fate of phthalate esters: a literature review. Chemosphere, 35, 667–749. doi:10.1016/S0045-6535(97)00195-1.
US EPA (United States Environmental Protection Agency).(1994). Water Quality Standards Handbook-Chapter 3 ‘EPA August 1994’, Publication EPA-823-B-B-94-005a, U.S. Environmental Protection Agency, Office of Water, Washington, DC.
Vitali, M., Leoni, V., Chiavarini, S., & Cremisini, C. (1993). Determination of 2-ethyl-1-hexanol as contaminant in drinking water. Journal of AOAC International, 76, 1133–1137.
Wong, C. C., & Chu, W. (2003). The direct photolysis and photocatalytic degradation of alachlor at different TiO2 and UV sources. Chemosphere, 50, 981–987. doi:10.1016/S0045-6535(02)00640-9.
Xu, B., Gao, N. Y., Sun, X. F., Xia, S. J., Rui, M., Simonnot, M. O., et al. (2007). Photochemical degradation of diethyl phthalate with UV/H2O2. Journal of Hazardous Materials, B139, 132–139. doi:10.1016/j.jhazmat.2006.06.026.
Yuan, S. Y., Liu, C., Liao, C. S., & Chang, B. V. (2002). Occurrence and microbial degradation of phthalate esters in Taiwan river sediments. Chemosphere, 49, 1295–1299. doi:10.1016/S0045-6535(02)00495-2.
Zheng, H. H., Zhao, L. W., Liu, Y. M., Zhou, X. Y., & Han, Z. Y. (2005). Detection of Phthalates in Drinking Water by GC-MS. Journal of Environmental Health, 22, 377–378.
Acknowledgment
The work was supported by a Grant from the National Science Council.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Chung, YC., Chen, CY. Degradation of Di-(2-ethylhexyl) Phthalate (DEHP) by TiO2 Photocatalysis. Water Air Soil Pollut 200, 191–198 (2009). https://doi.org/10.1007/s11270-008-9903-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11270-008-9903-9