Abstract
Using density functional theory methods, we studied the adsorption of (4-chloro-2-methylphenoxy)acetic acid (MCPA) and 2-(4-chlorophenoxy)-2-methylpropanoic acid, therapeutically used under the name of clofibric acid (CA), two commonly detected water pollutants, both in neutral and ionized form on a model surface of muscovite. We report the geometries of the adsorbed species and discuss their interaction with the surface. It was found that the ionized adsorbates interact more strongly with the surface than do their neutral forms particularly for MCPA when compared with CA, which points to the same direction of previous experimental findings. Changes on the electron density due to adsorption has been studied by means of Bader charges analysis and it was found that electronic density is transferred from the anions to the surface and less significantly from the surface to the neutral molecules on adsorption.
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Aga, D.S.: Fate of Pharmaceuticals in the Environment and in Water Treatment Systems. CRC Press, Boca Raton (2008)
Akcay, G., Yurdakoc, K.: Removal of various phenoxyalkanoic acid herbicides from water by organo-clays. Acta Hydrochim. Hydrobiol. 28, 300–304 (2000)
Barceló, D., Petrovic, M.: Emerging Contaminants from Industrial and Municipal Waste: Ocurrence, Analysis and Effects. Springer-Verlag, Berlin (2008)
Bell, K.Y., Wells, M.J.M., Traexler, K.A., Pellegrin, M.L., Morse, A., Bandy, J.: Emerging pollutants. Water Environ. Res. 83, 1906–1984 (2011)
Blöchl, P.E.: Projector augmented-wave method. Phys. Rev. B 50, 17953–17979 (1994)
Buchanan, I., Liang, H.C., Liu, Z.K., Razaviarani, V.: Pesticides and herbicides. Water Environ. Res. 83, 1549–1597 (2011)
Dordio, A.V., Candeias, A.J.E., Pinto, A.P., da Costa, C.T., Carvalho, A.J.P.: Preliminary media screening for application in the removal of clofibric acid, carbamazepine and ibuprofen by SSF-constructed wetlands. Ecol. Eng. 35, 290–302 (2009)
Dordio, A.V., Teimao, J., Ramalho, I., Palace Carvalho, A.J., Estêvão Candeias, A.J.: Selection of a support matrix for the removal of some phenoxyacetic compounds in constructed wetlands systems. Sci. Total Environ. 380, 237–246 (2007)
Esplugas, S., Bila, D.M., Krause, L.G., Dezotti, M.: Ozonation and advanced oxidation technologies to remove endocrine disrupting chemicals (EDCs) and pharmaceuticals and personal care products (PPCPs) in water effluents. J. Hazard. Mater. 149, 631–642 (2007)
Farré, M.L., Pérez, S., Kantiani, L., Barceló, D.: Fate and toxicity of emerging pollutants, their metabolites and transformation products in the aquatic environment. TrAC Trends Anal. Chem. 27, 991–1007 (2008)
Fent, K., Weston, A.A., Caminada, D.: Ecotoxicology of human pharmaceuticals. Aquat. Toxicol. 76, 122–159 (2006)
Ferrari, B., Paxéus, N., Lo Giudice, R., Pollio, A., Garric, J.: Ecotoxicological impact of pharmaceuticals found in treated wastewaters: study of carbamazepine, clofibric acid, and diclofenac. Ecotoxicol. Environ. Saf. 55, 359–370 (2003)
Gavrilescu, M.: Fate of pesticides in the environment and its bioremediation. Eng. Life Sci. 5, 497–526 (2005)
Hu, J., Yang, T., Yin, S., Cao, D.: Dissipation and residue of MCPA (4-chloro-2-ethylphenoxyacetate) in wheat and soil. Environ. Monit. Assess. 184, 5017–5024 (2012)
Iglesias, A., López, R., Gondar, D., Antelo, J., Fiol, S., Arce, F.: Adsorption of MCPA on goethite and humic acid-coated goethite. Chemosphere 78, 1403–1408 (2010)
Kasprzyk-Hordern, B., Dinsdale, R.M., Guwy, A.J.: The removal of pharmaceuticals, personal care products, endocrine disruptors and illicit drugs during wastewater treatment and its impact on the quality of receiving waters. Water Res. 43, 363–380 (2009)
Kennard, C.H.L., Smith, G., White, A.H.: Structural aspects of phenoxyalkanoic acids - the structures of phenoxyacetic acid, (±)-2-phenoxypropionic acid, (±)-2-(4-chlorophenoxy)propionic acid, 2-methyl-2-phenoxypropionic acid and 2-(4-chlorophenoxy)-2-methylpropionic acid. Acta Crystallogr. Sect. B Struct. Sci. 38, 868–875 (1982)
Kit Chan, W., Jouët, J., Heng, S., Lun Yeung, K., Schrotter, J.C.: Membrane contactor/separator for an advanced ozone membrane reactor for treatment of recalcitrant organic pollutants in water. J. Solid State Chem. 189, 96–100 (2012)
Kresse, G., Hafner, J.: Abinitio molecular–dynamics for liquid–metals. Phys. Rev. B 47, 558–561 (1993)
Kresse, G., Joubert, D.: From ultrasoft pseudopotentials to the projector augmented-wave method. Phys. Rev. B 59, 1758–1775 (1999)
Kümmerer, K.: Emerging contaminants. In: Wilderer, P. (ed.) Treatise on Water Science, pp. 69–87. Elsevier, Oxford (2011)
Kümmerer, K.: The presence of pharmaceuticals in the environment due to human use—present knowledge and future challenges. J. Environ. Manag. 90, 2354–2366 (2009)
Kuster, M., López de Alda, M.J., Hernando, M.D., Petrovic, M., Martín-Alonso, J., Barceló, D.: Analysis and occurrence of pharmaceuticals, estrogens, progestogens and polar pesticides in sewage treatment plant effluents, river water and drinking water in the Llobregat river basin (Barcelona, Spain). J. Hydrol. 358, 112–123 (2008)
Lapworth, D.J., Baran, N., Stuart, M.E., Ward, R.S.: Emerging organic contaminants in groundwater: a review of sources, fate and occurrence. Environ. Pollut. 163, 287–303 (2012)
Leng, Y.S., Cummings, P.T.: Hydration structure of water confined between mica surfaces. J. Chem. Phys. 124, 74711 (2006)
Matamoros, V., Arias, C.A., Nguyen, L.X., Salvadó, V., Brix, H.: Occurrence and behavior of emerging contaminants in surface water and a restored wetland. Chemosphere 88, 1083–1089 (2012)
Miège, C., Choubert, J.M., Ribeiro, L., Eusèbe, M., Coquery, M.: Fate of pharmaceuticals and personal care products in wastewater treatment plants—conception of a database and first results. Environ. Pollut. 157, 1721–1726 (2009)
Monicka, J.C., James, C.: Vibrational spectra and natural bond orbital analysis of the herbicidal molecule 2(4-chlorophenoxy)-2-methyl propionic acid. Spectrochim. Acta A Mol. Biomol. Spectrosc. 78, 718–725 (2011)
Odelius, M., Bernasconi, M., Parrinello, M.: Two dimensional ice adsorbed on mica surface. Phys. Rev. Lett. 78, 2855–2858 (1997)
Park, Y., Ayoko, G.A., Frost, R.L.: Application of organoclays for the adsorption of recalcitrant organic molecules from aqueous media. J. Colloid Interface Sci. 354, 292–305 (2011)
Perdew, J.P., Burke, K., Ernzerhof, M.: Generalized gradient approximation made simple. Phys. Rev. Lett. 77, 3865–3868 (1996)
Radjenovic, J., Petrovic, M., Barceló, D.: Advanced mass spectrometric methods applied to the study of fate and removal of pharmaceuticals in wastewater treatment. TrAC Trends Anal. Chem. 26, 1132–1144 (2007)
Rosal, R., Rodriguez, A., Perdigon-Melon, J.A., Petre, A., Garcia-Calvo, E., Gomez, M.J., Aguera, A., Fernandez-Alba, A.R.: Occurrence of emerging pollutants in urban wastewater and their removal through biological treatment followed by ozonation. Water Res. 44, 578–588 (2010)
Sieron, L., Kobylecka, J., Turek, A.: Crystal packing and supramolecular motifs in four phenoxyalkanoic acid herbicides: low-temperature redeterminations. Org. Chem. Int. 2011, (2011). doi:10.1155/2011/608165
Silva, E., Batista, S., Viana, P., Antunes, P., Serodio, L., Cardoso, A.T., Cerejeira, M.J.: Pesticides and nitrates in groundwater from oriziculture areas of the ‘Baixo Sado’ region (Portugal). Int. J. Environ. Anal. Chem. 86, 955–972 (2006)
Srivastava, B., Jhelum, V., Basu, D.D., Patanjali, P.K.: Adsorbents for pesticide uptake from contaminated water: a review. J. Sci. Ind. Res. 68, 839–850 (2009)
Tang, W., Sanville, E., Henkelman, G.: A grid-based Bader analysis algorithm without lattice bias. J. Phys.-Condes. Matter 21, 084204 (2009)
Tixier, C., Singer, H.P., Oellers, S., Muller, S.R.: Occurrence and fate of carbamazepine, clofibric acid, diclofenac, ibuprofen, ketoprofen, and naproxen in surface waters. Environ. Sci. Technol. 37, 1061–1068 (2003)
Tunega, D., Haberkauer, G., Gerzabek, M.H., Lischka, H.: Sorption of phenoxyacetic acid herbicides on the kaolinite mineral surface—an ab initio molecular dynamics simulation. Soil Sci. 169, 44–54 (2004)
van der Vaart, A., Merz, K.M.: Charge transfer in small hydrogen bonded clusters. J. Chem. Phys. 116, 7380–7388 (2002)
Verlicchi, P., Al Aukidy, M., Galletti, A., Petrovic, M., Barceló, D.: Hospital effluent: investigation of the concentrations and distribution of pharmaceuticals and environmental risk assessment. Sci. Total Environ. 430, 109–118 (2012)
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Prates Ramalho, J.P., Dordio, A.V. & Palace Carvalho, A.J. Adsorption of two phenoxyacid compounds on a clay surface: a theoretical study. Adsorption 19, 937–944 (2013). https://doi.org/10.1007/s10450-013-9492-9
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DOI: https://doi.org/10.1007/s10450-013-9492-9