Abstract
Previous researches investigated the adsorption properties and mechanism of clay minerals on antibiotic pharmaceuticals and personal care products (PPCPs) via batch adsorption experiments and X-ray diffraction (XRD) and Fourier transform infrared spectroscopy (FTIR) characterization, but many PPCPs exhibit different ionization states under different pH conditions; the research on the microscopic mechanism of different ionized PPCPs species adsorbed by clay minerals is very scarce. In this work, as a typical PPCPs contaminant, the common tetracycline (TC) was chosen as the study target; the adsorption micro mechanism of montmorillonite (MMT) on different TC species in aqueous solution was explored in details. Especially outstanding, for the first time, with the help of Multiwfn wavefunction program, quantitative analysis of molecular surface analysis and basin analysis were applied to quantitatively investigate the electrostatic interaction between MMT and different TC species, the possible positions of lone pair electrons. Independent gradient model (IGM) analysis and Hirshfeld surface analysis including local surface analysis were integrated to visualize the binding sites, interaction types, and relative strength between MMT and TC+/− or TC+/2− species, which can insight into the interaction essence from the microscopic perspective at the atomic level.
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Ahmed, M. J. (2017). Adsorption of quinolone, tetracycline, and penicillin antibiotics from aqueous solution using activated carbons: Review. Environ Toxicol Pharmacol, 50, 1–10.
Álvarez-Esmorís, C., Conde-Cid, M., Ferreira-Coelho, G., Fernández-Sanjurjo, M. J., Núñez-Delgado, A., Álvarez-Rodríguez, E., & Arias-Estévez, M. (2020). Adsorption/desorption of sulfamethoxypyridazine and enrofloxacin in agricultural soils. Sci Total Environ, 706, 136015.
Avisar, D., Primor, O., Gozlan, I., & Mamane, H. (2010). Sorption of sulfonamides and tetracyclines to montmorillonite clay. Water Air Soil Pollut, 209, 439–450.
Chang, P.-H., Li, Z., Yu, T.-L., Munkhbayer, S., Kuo, T.-H., Hung, Y.-C., Jean, J.-S., & Lin, K.-H. (2009). Sorptive removal of tetracycline from water by palygorskite. J Hazard Mater, 165, 148–155.
Chen, K.-L., Liu, L.-C., & Chen, W.-R. (2017). Adsorption of sulfamethoxazole and sulfapyridine antibiotics in high organic content soils. Environ Pollut, 231, 1163–1171.
De Oliveira, T., Guégan, R., Thiebault, T., Milbeau, C. L., Muller, F., Teixeira, V., Giovanela, M., & Boussafir, M. (2017). Adsorption of diclofenac onto organoclays: Effects of surfactant and environmental (pH and temperature) conditions. J Hazard Mater, 323, 558–566.
Djomgoue, P., Siewe, M., Djoufac, E., Kenfack, P., & Njopwouo, D. (2012). Surface modification of Cameroonian magnetite rich clay with Eriochrome Black T. Application for adsorption of nickel in aqueous solution. Appl Surf Sci, 258, 7470–7479.
Dordio, A. V., Miranda, S., Prates Ramalho, J. P., & Carvalho, A. J. P. (2017). Mechanisms of removal of three widespread pharmaceuticals by two clay materials. J Hazard Mater, 323, 575–583.
Evgenidou, E. N., Konstantinou, I. K., & Lambropoulou, D. A. (2015). Occurrence and removal of transformation products of PPCPs and illicit drugs in wastewaters: a review. Sci Total Environ, 505, 905–926.
Figueroa, R. A., Leonard, A., & MacKay, A. A. (2004). Modeling tetracycline antibiotic sorption to clays. Environ Sci Technol, 38, 476–483.
Freundlich, H. M. F. (1906). Über die Adsorption in Losungen. Z Phys Chem, 57, 385–470.
Frisch, M., Trucks, G., Schlegel, H., Scuseria, G., Robb, M., Cheeseman, Jr., Scalmani, G., Barone, V., Mennucci, B. & Petersson, G.: 2009, 'Gaussian 09 (Revision D.01)'.
Gros, M., Mas-Pla, J., Boy-Roura, M., Geli, I., Domingo, F., & Petrović, M. (2019). Veterinary pharmaceuticals and antibiotics in manure and slurry and their fate in amended agricultural soils: Findings from an experimental field site (Baix Empordà, NE Catalonia). Sci Total Environ, 654, 1337–1349.
Gu, C., & Karthikeyan, K. G. (2005). Interaction of tetracycline with aluminum and iron hydrous oxides. Environ Sci Technol, 39, 2660–2667.
Humphrey, W., Dalke, A., & Schulten, K. (1996). VMD: Visual molecular dynamics. J Mol Graph, 14, 33–38.
Langmuir, I. (1918). The adsorption of gases on plane surfaces of glass, mica and platinum. J Am Chem Soc, 40, 1361–1403.
Leal, R. M. P., Figueira, R. F., Tornisielo, V. L., & Regitano, J. B. (2012). Occurrence and sorption of fluoroquinolones in poultry litters and soils from São Paulo State, Brazil. Sci Total Environ, 432, 344–349.
Lefebvre, C., Rubez, G., Khartabil, H., Boisson, J.-C., Contreras-García, J., & Hénon, E. (2017). Accurately extracting the signature of intermolecular interactions present in the NCI plot of the reduced density gradient versus electron density. PCCP, 19, 17928–17936.
Leung, H. W., Minh, T. B., Murphy, M. B., Lam, J. C. W., So, M. K., Martin, M., Lam, P. K. S., & Richardson, B. J. (2012). Distribution, fate and risk assessment of antibiotics in sewage treatment plants in Hong Kong, South China. Environ Int, 42, 1–9.
Li, Z., Chang, P.-H., Jean, J.-S., Jiang, W.-T., & Wang, C.-J. (2010a). Interaction between tetracycline and smectite in aqueous solution. J Colloid Interface Sci, 341, 311–319.
Li, Z., Schulz, L., Ackley, C., & Fenske, N. (2010b). Adsorption of tetracycline on kaolinite with pH-dependent surface charges. J Colloid Interface Sci, 351, 254–260.
Lin, T., Yu, S., & Chen, W. (2016). Occurrence, removal and risk assessment of pharmaceutical and personal care products (PPCPs) in an advanced drinking water treatment plant (ADWTP) around Taihu Lake in China. Chemosphere, 152, 1–9.
Liu, Y., Lu, X., Wu, F., & Deng, N. (2011). Adsorption and photooxidation of pharmaceuticals and personal care products on clay minerals. React Kinet Mech Catal, 104, 61–73.
Liu, M., Zhang, Y., Yang, M., Tian, Z., Ren, L., & Zhang, S. (2012a). Abundance and distribution of tetracycline resistance genes and mobile elements in an oxytetracycline production wastewater treatment system. Environ Sci Technol, 46, 7551–7557.
Liu, N., Wang, M.-X., Liu, M.-M., Liu, F., Weng, L., Koopal, L. K., & Tan, W.-F. (2012b). Sorption of tetracycline on organo-montmorillonites. J Hazard Mater, 225-226, 28–35.
Long, H., Wu, P., Yang, L., Huang, Z., Zhu, N., & Hu, Z. (2014). Efficient removal of cesium from aqueous solution with vermiculite of enhanced adsorption property through surface modification by ethylamine. J Colloid Interface Sci, 428, 295–301.
Lu, T., & Chen, F. (2012a). Multiwfn: a multifunctional wavefunction analyzer. J Comput Chem, 33, 580–592.
Lu, T., & Chen, F. (2012b). Quantitative analysis of molecular surface based on improved Marching Tetrahedra algorithm. J Mol Graphics Modell, 38, 314–323.
Luo, Y., Guo, W., Ngo, H. H., Nghiem, L. D., Hai, F. I., Zhang, J., Liang, S., & Wang, X. C. (2014). A review on the occurrence of micropollutants in the aquatic environment and their fate and removal during wastewater treatment. Sci Total Environ, 473-474, 619–641.
McKinnon, J. J., Mitchell, A. S., & Spackman, M. A. (1998). Hirshfeld Surfaces: a new tool for visualising and exploring molecular crystals. Chem Eur J, 4, 2136–2141.
Parolo, M. E., Savini, M. C., Vallés, J. M., Baschini, M. T., & Avena, M. J. (2008). Tetracycline adsorption on montmorillonite: pH and ionic strength effects. Appl Clay Sci, 40, 179–186.
Parolo, M. E., Avena, M. J., Savini, M. C., Baschini, M. T., & Nicotra, V. (2013). Adsorption and circular dichroism of tetracycline on sodium and calcium-montmorillonites. Colloids Surf A Physicochem Eng Asp, 417, 57–64.
Pils, J. R. V., & Laird, D. A. (2007). Sorption of tetracycline and chlortetracycline on K- and Ca-saturated soil clays, humic substances, and clay−humic complexes. Environ Sci Technol, 41, 1928–1933.
Qiao, M., Ying, G.-G., Singer, A. C., & Zhu, Y.-G. (2018). Review of antibiotic resistance in China and its environment. Environ Int, 110, 160–172.
Sassman, S. A., & Lee, L. S. (2005). Sorption of three tetracyclines by several soils: assessing the role of pH and cation exchange. Environ Sci Technol, 39, 7452–7459.
Shen, T., Wang, L., Zhao, Q., Guo, S., & Gao, M. (2020). Single and simultaneous adsorption of basic dyes by novel organo-vermiculite: a combined experimental and theoretical study. Colloids Surf A Physicochem Eng Asp, 601, 125059.
Sjoberg, P., Murray, J. S., Brinck, T., & Politzer, P. (1990). Average local ionization energies on the molecular surfaces of aromatic systems as guides to chemical reactivity. Revue Canadienne De Chimie, 68, 1440–1443.
Spackman, M. A., & Byrom, P. G. (1997). A novel definition of a molecule in a crystal. Chem Phys Lett, 267, 215–220.
Sun, Q., Lv, M., Hu, A., Yang, X., & Yu, C.-P. (2014). Seasonal variation in the occurrence and removal of pharmaceuticals and personal care products in a wastewater treatment plant in Xiamen, China. J Hazard Mater, 277, 69–75.
Sun, Q., Li, Y., Li, M., Ashfaq, M., Lv, M., Wang, H., Hu, A., & Yu, C.-P. (2016). PPCPs in Jiulong River estuary (China): Spatiotemporal distributions, fate, and their use as chemical markers of wastewater. Chemosphere, 150, 596–604.
Sun, K., Shi, Y., Wang, X., Rasmussen, J., Li, Z., & Zhu, J. (2017). Organokaolin for the uptake of pharmaceuticals diclofenac and chloramphenicol from water. Chem Eng J, 330, 1128–1136.
Tian, G., Wang, W., Zong, L., Kang, Y., & Wang, A. (2016). A functionalized hybrid silicate adsorbent derived from naturally abundant low-grade palygorskite clay for highly efficient removal of hazardous antibiotics. Chem Eng J, 293, 376–385.
Tran, H. N., You, S. J., Hosseini-Bandegharaei, A., & Chao, H. P. (2017). Mistakes and inconsistencies regarding adsorption of contaminants from aqueous solutions: a critical review. Water Res, 120, 88–116.
Turku, I., Sainio, T., & Paatero, E. (2007). Thermodynamics of tetracycline adsorption on silica. Environ Chem Lett, 5, 225–228.
Vazquez, A., Lopez, M., Kortaberria, G., Martin, L., & Mondragon, I. (2008). Modification of montmorillonite with cationic surfactants. Thermal and chemical analysis including CEC determination. Appl Clay Sci, 41, 24–36.
Wang, C.-J., Li, Z., Jiang, W.-T., Jean, J.-S., & Liu, C.-C. (2010). Cation exchange interaction between antibiotic ciprofloxacin and montmorillonite. J Hazard Mater, 183, 309–314.
Wu, Q., Li, Z., & Hong, H. (2013). Adsorption of the quinolone antibiotic nalidixic acid onto montmorillonite and kaolinite. Appl Clay Sci, 74, 66–73.
Wu, H., Xie, H., He, G., Guan, Y., & Zhang, Y. (2016). Effects of the pH and anions on the adsorption of tetracycline on iron-montmorillonite. Appl Clay Sci, 119, 161–169.
Zheng, S., Sun, Z., Park, Y., Ayoko, G. A., & Frost, R. L. (2013). Removal of bisphenol A from wastewater by Ca-montmorillonite modified with selected surfactants. Chem Eng J, 234, 416–422.
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This work was supported by the National Natural Science Foundation of China [grant numbers 51472121, 51572127, 51572130, and 51672134].
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Zhang, H., Shi, M., Xia, M. et al. The Adsorption Mechanism of Montmorillonite for Different Tetracycline Species at Different pH Conditions: the Novel Visual Analysis of Intermolecular Interactions. Water Air Soil Pollut 232, 65 (2021). https://doi.org/10.1007/s11270-021-05012-7
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DOI: https://doi.org/10.1007/s11270-021-05012-7