Effects of pH, temperature, ionic strength and organic matter on triclocarban solubility
Abstract
The solubility of triclocarban in ultrapure water and in several natural aqueous solutions is influenced by several environmental factors. In this study the variation of temperature, pH, ionic strength and concentration of the organic matter over the solubility of triclocarban was analysed. The results show that the solubility of triclocarban increases by increasing the contact time, longer than the time of equilibrium and the temperature. It is less influenced by the variations of pH and strongly influenced by the variation of ionic strength and by the natural organic matter into the studied aqueous matrices.
Keyword : solubility, triclocarban, aqueous solutions, water pollution
How to Cite
Ivan, G. R., Ion, I., Capra, L., & Ion, A. C. (2021). Effects of pH, temperature, ionic strength and organic matter on triclocarban solubility. Journal of Environmental Engineering and Landscape Management, 29(3), 244-250. https://doi.org/10.3846/jeelm.2021.14638
This work is licensed under a Creative Commons Attribution 4.0 International License.
References
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Delgado, D. R., Holguin, A. R., & Martínez, F. (2012). Solution thermodynamics of Triclosan and Triclocarban in some volatile organic solvents. Vitae, 19, 79–92. https://www.researchgate.net/publication/235577701
Delgado, D. R., Mogollon-Waltero, E. M., Ortiz, C. P., Peña, M. Á., Almanza, O. A., Martínez, F., & Jouyban, A. (2018). Enthalpy-entropy compensation analysis of the triclocarban dissolution process in some {1,4-dioxane (1) + water (2)} mixtures. Journal of Molecular Liquids, 271, 522–529. https://doi.org/10.1016/j.molliq.2018.09.026
Diana, M. A., Alejandro, S., & Fleming, M. (2009). Solution thermodynamics of triclocarban in organic solvents of different hydrogen bonding capability. Journal of Solution Chemistry, 38, 1493–1503. https://doi.org/10.1007/s10953-009-9464-6
Ding, S. L., Wang, X. K., Jiang, W. Q., Zhao, R. S., Shen, T. T., Wang, C., & Wang, X. (2015). Influence of pH, inorganic anions and dissolved organic matter on the photolysis of antimicrobial triclocarban in aqueous systems under simulated sunlight irradiation. Environmental Science and Pollution Research, 22, 5204–5211. https://doi.org/10.1007/s11356-014-3686-x
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Halden, R. U., & Paull, D. H. (2004). Analysis of triclocarban in aquatic samples by liquid chromatography electrospray ionization mass spectrometry. Environmental Science & Technology, 38(18), 4849–4855. https://doi.org/10.1021/es049524f
Halden, R. U., & Paull, D. H. (2005). Co-occurrence of triclocarban and triclosan in U.S. water resources. Environmental Science & Technology, 39(6), 1420–1426. https://doi.org/10.1021/es049071e
Hynther, A., Bromba, C. M., Wulff, J. E., & Helbing, C. C. (2011). Effects of triclocarban, triclosan and methyl triclosan on thyroid hormone action and stress in frog and mammalian culture systems. Environmental Science & Technology, 45(12), 5395–5402. https://doi.org/10.1021/es1041942
INERIS. (2016). Données technico-économiques sur les substances chimiques en France: Triclocarban (DRC-16-158744-08924A). Portail Substances Chimiques. http://www.ineris.fr/substances/fr/
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Ion, I., Senin, R. M., Ivan, G. R., Doncea, S. M., Capra, L., Henning, M. P, & Ion, A. C. (2019b). Adsorption of triclocarban on pristine and irradiated MWCNTs in aqueous solutions. Revista de Chimie (Bucharest), 70(8), 2835–2842. https://doi.org/10.37358/RC.19.8.7438
Junhyuk, L., Sunghyun, J., Hwayong, K., Hye, K. C., & Moon, S. S. (2013). Solubility of triclocarban in pure alkanols at different temperatures. Korean Journal of Chemical Engineering, 30(1), 181–186. https://doi.org/10.1007/s11814-012-0099-8
Kennedy, R. C., Fling, R. R., Terry, P. D., Menn, F. M., Chen, J., & Borman, C. J. (2015). Extraction of 3,4,4′-Trichlorocarbanilide from rat fecal samples for determination by high pressure liquid chromatography-tandem mass spectrometry. International Journal of Environmental Research and Public Health, 12(7), 8125–8132. https://doi.org/10.3390/ijerph120708125
Lehutso, R. F., Daso, A. P., & Okonkwo, J. O. (2017). Occurrence and environmental levels of triclosan and triclocarban in selected wastewater treatment plants in Gauteng Province, South Africa. Emerging Contaminants, 3(3), 107–114. https://doi.org/10.1016/j.emcon.2017.07.001
Loftin, K. A., Adams, C. D., Meyer, M. T., & Surampalli, R. (2008). Effects of ionic strength, temperature, and pH on degradation of selected antibiotics. Journal of Environmental Quality, 37(2), 378–386. https://doi.org/10.2134/jeq2007.0230
Lv, M., Sun, Q., Xu, H., Lin, L., Chen, M., & Yu, C. P. (2014). Occurrence and fate of triclosan and triclocarban in a subtropical river and its estuary. Marine Pollution Bulletin, 88(1–2), 383–388. https://doi.org/10.1016/j.marpolbul.2014.07.065
Miller, T. R., Heidler, J., Chillrud, S. N., DeLaquil, A., Ritchie, J. C., Mihalic, J. N., Bopp, R., & Halden, R. U. (2008). Fate of triclosan and evidence for reductive dechlorination of triclocarban in estuarine sediments. Environmental Science & Technology, 42(12), 4570–4576. https://doi.org/10.1021/es702882g
Mora, C. P., & Martínez, F. (2007). Thermodynamic study of partitioning and solvation of (+)-naproxen in some organic solvent/buffer and liposome systems. Journal of Chemical & Engineering Data, 52(5), 1933–1940. https://doi.org/10.1021/je700241c
Roman, D., Barnett, E., & Balske, R. (1957). Cutaneous antiseptic activity of 3, 4, 4′-trichlorocarbanilide. Proceedings of the Scientific Section of the Toilet Goods Association, 28, 12–13.
Sangster, J. (1997). Octanol-water partition coefficients: Fundamentals and physical chemistry (1 ed.). John Wiley & Sons. https://www.wiley.com/en-us/Octanol+Water+Partition+Coefficients%3A+Fundamentals+and+Physical+Chemistry-p-9780471973973
Sapkota, A., Heidler, J., & Halden, R. (2007). Detection of triclocarban and two co-contaminating chlorocarbanilides in US aquatic environments using isotope dilution liquid chromatography tandem mass spectrometry. Environmental Research, 103(1), 21–29. https://doi.org/10.1016/j.envres.2006.03.006
Schebb, N. H., Inceoglu, B., Ahn, K. C., Morisseau, C., Gee, S. J., & Hammock, B. D. (2011). Investigation of human exposure to triclocarban after showering and preliminary evaluation of its biological effects. Environmental Science & Technology, 45(7), 3109–3115. https://doi.org/10.1021/es103650m
Snyder, E. H., & O’Connor, G. A. (2013). Risk assessment of land-applied biosolids-borne triclocarban (TCC). Science of The Total Environment, 442, 437–444. https://doi.org/10.1016/j.scitotenv.2012.10.007
Snyder, E. H., O’Connor, G. A., & McAvoy, D. C. (2010). Measured physico-chemical characteristics and biosolids-borne concentrations of the antimicrobial Triclocarban (TCC). Science of the Total Environment, 408(13), 2667–2673. https://doi.org/10.1016/j.scitotenv.2010.03.001
TCC Consortium. (2002). High production volume (HPV) chemical challenge program data availability and screening level assessment for triclocarban, CAS#: 101-20-2. 201-14186A. Prepared for the HPV Challenge Program by: The TCC Consortium December 27, 2002. https://www.aciscience.org/docs/Triclocarban_HPV_Test_Plan.pdf
Venkatesan, A. K., Pycke, B. F., Barber, L. B., Lee, K. E., & Halden, R. U. (2012). Occurrence of triclosan, triclocarban, and its lesser chlorinated congeners in Minnesota freshwater sediments collected near wastewater treatment plants. Journal of Hazardous Materials, 229–230, 29–35. https://doi.org/10.1016/j.jhazmat.2012.05.049
Vimalkumar, K., Arun, E., Krishna-Kumar, S., Poopal, R. K., Nikhil, N. P., Subramanian, A., & Babu-Rajendran, R. (2018). Occurrence of triclocarban and benzotriazole ultraviolet stabilizers in water, sediment, and fish from Indian rivers. Science of the Total Environment, 625, 1351–1360. https://doi.org/10.1016/j.scitotenv.2018.01.042
Vimalkumar, K., Seethappan, S., & Pugazhendhi, A. (2019). Fate of Triclocarban (TCC) in aquatic and terrestrial systems and human exposure. Chemosphere, 230, 201–209. https://doi.org/10.1016/j.chemosphere.2019.04.145
Wanga, D., Taoa, L., Yanga, J., Xuc, Z., Yanga, Q., Zhanga, Y., Liua, X., Liua, Q., & Huang, J. (2020). Understanding the interaction between triclocarban and denitrifiers. Journal of Hazardous Materials, 401, 123343. https://doi.org/10.1016/j.jhazmat.2020.123343
Ying, G., Yu, X., & Kookana, R. (2007). Biological degradation of triclocarban and triclosan in a soil under aerobic and anaerobic conditions and comparison with environmental fate modeling. Environmental Pollution, 150(3), 300–305. https://doi.org/10.1016/j.envpol.2007.02.013
Zhao, J. L., Ying, G. G., Liu, Y. S., Chen, F., Yang, J. F., & Wang, L. (2013). Occurrence and risks of triclosan and triclocarban in the Pearl River system, South China: From source to the receiving environment. Journal of Hazardous Materials, 179(1– 3), 215–222. https://doi.org/10.1016/j.jhazmat.2010.02.082
Borrirukwisitsak, S., Keenan, H. E., & Gauchotte-Lindsay, C. (2012). Effects of salinity, pH and temperature on the octanol-water partition coefficient of bisphenol A. International Journal of Environmental Science and Development, 3(5), 460–464. https://doi.org/10.7763/IJESD.2012.V3.267
Cantwell, M. G., Wilson, B. A., Zhu, J., Wallace, G. T., King, J. W., Olsen, C. R., Burgess, R. M., & Smith, J. P. (2010). Temporal trends of triclosan contamination in dated sediment cores from four urbanized estuaries: evidence of preservation and accumulation. Chemosphere, 78(4), 347–352. https://doi.org/10.1016/j.chemosphere.2009.11.021
Commission Directive. (1992). Directive 92/69/EEC of 31 July 1992, A.6 Water solubility. https://eur-lex.europa.eu/legal-content/EN/TXT/?uri=CELEX:31992L0069
Council Directive. (1976). Council Directive of 27 July 1976 on the approximation of the laws of the Member States relating to cosmetic products (76/768 / EEC, anexa VI, part 1, no. 23). https://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=CONSLEG:1976L0768:20100301:en:PDF
Delgado, D. R., Holguin, A. R., & Martínez, F. (2012). Solution thermodynamics of Triclosan and Triclocarban in some volatile organic solvents. Vitae, 19, 79–92. https://www.researchgate.net/publication/235577701
Delgado, D. R., Mogollon-Waltero, E. M., Ortiz, C. P., Peña, M. Á., Almanza, O. A., Martínez, F., & Jouyban, A. (2018). Enthalpy-entropy compensation analysis of the triclocarban dissolution process in some {1,4-dioxane (1) + water (2)} mixtures. Journal of Molecular Liquids, 271, 522–529. https://doi.org/10.1016/j.molliq.2018.09.026
Diana, M. A., Alejandro, S., & Fleming, M. (2009). Solution thermodynamics of triclocarban in organic solvents of different hydrogen bonding capability. Journal of Solution Chemistry, 38, 1493–1503. https://doi.org/10.1007/s10953-009-9464-6
Ding, S. L., Wang, X. K., Jiang, W. Q., Zhao, R. S., Shen, T. T., Wang, C., & Wang, X. (2015). Influence of pH, inorganic anions and dissolved organic matter on the photolysis of antimicrobial triclocarban in aqueous systems under simulated sunlight irradiation. Environmental Science and Pollution Research, 22, 5204–5211. https://doi.org/10.1007/s11356-014-3686-x
European Commission. (2005). Scientific Committee on Consumer Products SCCP/0851/04, 2005. Opinion on Triclocarban for other uses than as a preservative COLIPA no. P29. https://ec.europa.eu/health/ph_risk/committees/04_sccp/docs/sccp_o_016.pdf
Halden, R. U., & Paull, D. H. (2004). Analysis of triclocarban in aquatic samples by liquid chromatography electrospray ionization mass spectrometry. Environmental Science & Technology, 38(18), 4849–4855. https://doi.org/10.1021/es049524f
Halden, R. U., & Paull, D. H. (2005). Co-occurrence of triclocarban and triclosan in U.S. water resources. Environmental Science & Technology, 39(6), 1420–1426. https://doi.org/10.1021/es049071e
Hynther, A., Bromba, C. M., Wulff, J. E., & Helbing, C. C. (2011). Effects of triclocarban, triclosan and methyl triclosan on thyroid hormone action and stress in frog and mammalian culture systems. Environmental Science & Technology, 45(12), 5395–5402. https://doi.org/10.1021/es1041942
INERIS. (2016). Données technico-économiques sur les substances chimiques en France: Triclocarban (DRC-16-158744-08924A). Portail Substances Chimiques. http://www.ineris.fr/substances/fr/
Ion, I., Ivan, G. R., Senin, R. M., Doncea, S. M., Capra, L., Modrogan, C., Oprea, O., Stinga, G., Orbulet, O., & Ion, A. C. (2019a). Adsorption of triclocarban (TCC) onto fullerene C60 in simulated environmental aqueous conditions. Separation Science and Technology, 54(17), 2759–2772. https://doi.org/10.1080/01496395.2019.1577450
Ion, I., Senin, R. M., Ivan, G. R., Doncea, S. M., Capra, L., Henning, M. P, & Ion, A. C. (2019b). Adsorption of triclocarban on pristine and irradiated MWCNTs in aqueous solutions. Revista de Chimie (Bucharest), 70(8), 2835–2842. https://doi.org/10.37358/RC.19.8.7438
Junhyuk, L., Sunghyun, J., Hwayong, K., Hye, K. C., & Moon, S. S. (2013). Solubility of triclocarban in pure alkanols at different temperatures. Korean Journal of Chemical Engineering, 30(1), 181–186. https://doi.org/10.1007/s11814-012-0099-8
Kennedy, R. C., Fling, R. R., Terry, P. D., Menn, F. M., Chen, J., & Borman, C. J. (2015). Extraction of 3,4,4′-Trichlorocarbanilide from rat fecal samples for determination by high pressure liquid chromatography-tandem mass spectrometry. International Journal of Environmental Research and Public Health, 12(7), 8125–8132. https://doi.org/10.3390/ijerph120708125
Lehutso, R. F., Daso, A. P., & Okonkwo, J. O. (2017). Occurrence and environmental levels of triclosan and triclocarban in selected wastewater treatment plants in Gauteng Province, South Africa. Emerging Contaminants, 3(3), 107–114. https://doi.org/10.1016/j.emcon.2017.07.001
Loftin, K. A., Adams, C. D., Meyer, M. T., & Surampalli, R. (2008). Effects of ionic strength, temperature, and pH on degradation of selected antibiotics. Journal of Environmental Quality, 37(2), 378–386. https://doi.org/10.2134/jeq2007.0230
Lv, M., Sun, Q., Xu, H., Lin, L., Chen, M., & Yu, C. P. (2014). Occurrence and fate of triclosan and triclocarban in a subtropical river and its estuary. Marine Pollution Bulletin, 88(1–2), 383–388. https://doi.org/10.1016/j.marpolbul.2014.07.065
Miller, T. R., Heidler, J., Chillrud, S. N., DeLaquil, A., Ritchie, J. C., Mihalic, J. N., Bopp, R., & Halden, R. U. (2008). Fate of triclosan and evidence for reductive dechlorination of triclocarban in estuarine sediments. Environmental Science & Technology, 42(12), 4570–4576. https://doi.org/10.1021/es702882g
Mora, C. P., & Martínez, F. (2007). Thermodynamic study of partitioning and solvation of (+)-naproxen in some organic solvent/buffer and liposome systems. Journal of Chemical & Engineering Data, 52(5), 1933–1940. https://doi.org/10.1021/je700241c
Roman, D., Barnett, E., & Balske, R. (1957). Cutaneous antiseptic activity of 3, 4, 4′-trichlorocarbanilide. Proceedings of the Scientific Section of the Toilet Goods Association, 28, 12–13.
Sangster, J. (1997). Octanol-water partition coefficients: Fundamentals and physical chemistry (1 ed.). John Wiley & Sons. https://www.wiley.com/en-us/Octanol+Water+Partition+Coefficients%3A+Fundamentals+and+Physical+Chemistry-p-9780471973973
Sapkota, A., Heidler, J., & Halden, R. (2007). Detection of triclocarban and two co-contaminating chlorocarbanilides in US aquatic environments using isotope dilution liquid chromatography tandem mass spectrometry. Environmental Research, 103(1), 21–29. https://doi.org/10.1016/j.envres.2006.03.006
Schebb, N. H., Inceoglu, B., Ahn, K. C., Morisseau, C., Gee, S. J., & Hammock, B. D. (2011). Investigation of human exposure to triclocarban after showering and preliminary evaluation of its biological effects. Environmental Science & Technology, 45(7), 3109–3115. https://doi.org/10.1021/es103650m
Snyder, E. H., & O’Connor, G. A. (2013). Risk assessment of land-applied biosolids-borne triclocarban (TCC). Science of The Total Environment, 442, 437–444. https://doi.org/10.1016/j.scitotenv.2012.10.007
Snyder, E. H., O’Connor, G. A., & McAvoy, D. C. (2010). Measured physico-chemical characteristics and biosolids-borne concentrations of the antimicrobial Triclocarban (TCC). Science of the Total Environment, 408(13), 2667–2673. https://doi.org/10.1016/j.scitotenv.2010.03.001
TCC Consortium. (2002). High production volume (HPV) chemical challenge program data availability and screening level assessment for triclocarban, CAS#: 101-20-2. 201-14186A. Prepared for the HPV Challenge Program by: The TCC Consortium December 27, 2002. https://www.aciscience.org/docs/Triclocarban_HPV_Test_Plan.pdf
Venkatesan, A. K., Pycke, B. F., Barber, L. B., Lee, K. E., & Halden, R. U. (2012). Occurrence of triclosan, triclocarban, and its lesser chlorinated congeners in Minnesota freshwater sediments collected near wastewater treatment plants. Journal of Hazardous Materials, 229–230, 29–35. https://doi.org/10.1016/j.jhazmat.2012.05.049
Vimalkumar, K., Arun, E., Krishna-Kumar, S., Poopal, R. K., Nikhil, N. P., Subramanian, A., & Babu-Rajendran, R. (2018). Occurrence of triclocarban and benzotriazole ultraviolet stabilizers in water, sediment, and fish from Indian rivers. Science of the Total Environment, 625, 1351–1360. https://doi.org/10.1016/j.scitotenv.2018.01.042
Vimalkumar, K., Seethappan, S., & Pugazhendhi, A. (2019). Fate of Triclocarban (TCC) in aquatic and terrestrial systems and human exposure. Chemosphere, 230, 201–209. https://doi.org/10.1016/j.chemosphere.2019.04.145
Wanga, D., Taoa, L., Yanga, J., Xuc, Z., Yanga, Q., Zhanga, Y., Liua, X., Liua, Q., & Huang, J. (2020). Understanding the interaction between triclocarban and denitrifiers. Journal of Hazardous Materials, 401, 123343. https://doi.org/10.1016/j.jhazmat.2020.123343
Ying, G., Yu, X., & Kookana, R. (2007). Biological degradation of triclocarban and triclosan in a soil under aerobic and anaerobic conditions and comparison with environmental fate modeling. Environmental Pollution, 150(3), 300–305. https://doi.org/10.1016/j.envpol.2007.02.013
Zhao, J. L., Ying, G. G., Liu, Y. S., Chen, F., Yang, J. F., & Wang, L. (2013). Occurrence and risks of triclosan and triclocarban in the Pearl River system, South China: From source to the receiving environment. Journal of Hazardous Materials, 179(1– 3), 215–222. https://doi.org/10.1016/j.jhazmat.2010.02.082