Abstract
Degradation of triclosan (TCS) by multifrequency ultrasound (US) was studied at high and low frequencies. Frequency effect on initial degradation rates was analyzed, and an optimum frequency was found. Power density always has a positive effect on degradation rates over the whole equipment work range. A reaction mechanism similar to that proposed by Serpone resulted in a pseudo-linear model that fitted statistically better than the nonlinear model proposed by Okitsu. Pulsed US showed a positive effect on degradation rates; however, simultaneous analysis of the effect of power, frequency, pulse time, and silent time did not show a clear trend for degradation as a function of pulse US variables. According to these results and those for degradation in the presence of radical scavengers, it was concluded that US TCS degradation was taking place in the bubble/liquid interface. A toxicity test was conducted by Microtox®, showing a decrease in toxicity as TCS concentration decreased and increase in toxicity after total depletion of TCS. Eight possible degradation by-products were identified by GC-MS analysis, and a degradation pathway was proposed.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Adewuyi YG, Oyenekan BA (2007) Optimization of a sonochemical process using a novel reactor and Taguchi statistical experimental design methodology. Ind Eng Chem Res 46:411–420. https://doi.org/10.1021/ie060844c
Apfel RE (1981) 7. Acoustic cavitation. In: Ultrasonics. Series: Methods in experimental physics. Elsevier, New York, pp 355–411
Aranami K, Readman JW (2007) Photolytic degradation of triclosan in freshwater and seawater. Chemosphere 66:1052–1056. https://doi.org/10.1016/j.chemosphere.2006.07.010
Behera SK, Oh SY, Park HS (2010) Sorption of triclosan onto activated carbon, kaolinite and montmorillonite: effects of pH, ionic strength, and humic acid. J Hazard Mater 179:684–691. https://doi.org/10.1016/j.jhazmat.2010.03.056
Blair E (1971) Chlorodioxins—origin and fate. American Chemical Society, Washington D.C
Chiha M, Hamdaoui O, Baup S, Gondrexon N (2011) Sonolytic degradation of endocrine disrupting chemical 4-cumylphenol in water. Ultrason Sonochem 18:943–950. https://doi.org/10.1016/j.ultsonch.2010.12.014
De Bel E, Janssen C, De Smet S et al (2011) Sonolysis of ciprofloxacin in aqueous solution: influence of operational parameters. Ultrason Sonochem 18:184–189. https://doi.org/10.1016/j.ultsonch.2010.05.003
Farré M, Asperger D, Kantiani L et al (2008) Assessment of the acute toxicity of triclosan and methyl triclosan in wastewater based on the bioluminescence inhibition of Vibrio fischeri. Anal Bioanal Chem 390:1999–2007. https://doi.org/10.1007/s00216-007-1779-9
Hayduk W, Laudie H (1974) Prediction of diffusion coefficients for nonelectrolytes in dilute aqueous solutions. AICHE J 20:611–615. https://doi.org/10.1002/aic.690200329
Henglein A (1987) Sonochemistry: historical developments and modern aspects. Ultrasonics 25:6–16. https://doi.org/10.1016/0041-624X(87)90003-5
Hites RA (2011) Dioxins: an overview and history †. Environ Sci Technol 45:16–20. https://doi.org/10.1021/es1013664
Ince NH, Gültekin I, Tezcanli-Güyer G (2009) Sonochemical destruction of nonylphenol: effects of pH and hydroxyl radical scavengers. J Hazard Mater 172:739–743. https://doi.org/10.1016/j.jhazmat.2009.07.058
Khanna S, Chakma S, Moholkar VS (2013) Phase diagrams for dual frequency sonic processors using organic liquid medium. Chem Eng Sci 100:137–144. https://doi.org/10.1016/j.ces.2013.02.016
Kimura T, Sakamoto T, Leveque J et al (1996) Standardization of ultrasonic power for sonochemical reaction. Ultrason Sonochem 3:S157–S161. https://doi.org/10.1016/S1350-4177(96)00021-1
Kolpin DW, Kolpin DW, Furlong ET et al (2002) Pharmaceuticals, hormones, and other organic wastewater contaminants in U.S. streams, 1999-2000: A national Recoinnaissance. Environ Sci Technol 36:1202–1211. https://doi.org/10.1021/es011055j
Latch DE, Packer JL, Arnold WA, McNeill K (2003) Photochemical conversion of triclosan to 2,8-dichlorodibenzo-p-dioxin in aqueous solution. J Photochem Photobiol A Chem 158:63–66. https://doi.org/10.1016/S1010-6030(03)00103-5
Latch DE, Packer JL, Stender BLB et al (2005) Aqueous photochemistry of triclosan: formation of 2,4-dichlorophenol, 2,8-dichlorodibenzo-p-dioxin, and oligomerization products. Environ Toxicol Chem 24:517–525. https://doi.org/10.1897/04-243R.1
Lores M, Llompart M, Sanchez-Prado L et al (2005) Confirmation of the formation of dichlorodibenzo-p-dioxin in the photodegradation of triclosan by photo-SPME. Anal Bioanal Chem 381:1294–1298. https://doi.org/10.1007/s00216-004-3047-6
Mahamuni NN, Adewuyi YG (2010) Advanced oxidation processes (AOPs) involving ultrasound for waste water treatment: a review with emphasis on cost estimation. Ultrason Sonochem 17:990–1003. https://doi.org/10.1016/j.ultsonch.2009.09.005
Mezcua M, Gómez MJ, Ferrer I et al (2004) Evidence of 2,7/2,8-dibenzodichloro-p-dioxin as a photodegradation product of triclosan in water and wastewater samples. Anal Chim Acta 524:241–247. https://doi.org/10.1016/j.aca.2004.05.050
Munoz M, de Pedro ZM, Casas JA, Rodriguez JJ (2012) Triclosan breakdown by Fenton-like oxidation. Chem Eng J 198–199:275–281. https://doi.org/10.1016/j.cej.2012.05.097
Naddeo V, Landi M, Scannapieco D, Belgiorno V (2013) Sonochemical degradation of twenty-three emerging contaminants in urban wastewater. Desalin Water Treat 51:6601–6608. https://doi.org/10.1080/19443994.2013.769696
Okitsu K, Iwasaki K, Yobiko Y et al (2005) Sonochemical degradation of azo dyes in aqueous solution: a new heterogeneous kinetics model taking into account the local concentration of OH radicals and azo dyes. Ultrason Sonochem 12:255–262. https://doi.org/10.1016/j.ultsonch.2004.01.038
Okitsu K, Suzuki T, Takenaka N et al (2006) Acoustic multibubble cavitation in water: a new aspect of the effect of a rare gas atmosphere on bubble temperature and its relevance to sonochemistry. J Phys Chem B 110:20081–20084. https://doi.org/10.1021/jp064598u
Onorati F, Mecozzi M (2004) Effects of two diluents in the Microtox toxicity bioassay with marine sediments. Chemosphere 54:679–687. https://doi.org/10.1016/j.chemosphere.2003.09.010
Pétrier C (2015) The use of power ultrasound for water treatment. In: Power ultrasonics. Applications of high-intensity ultrasound. Woodhead Publishing, Elsevier, pp 939–972. https://doi.org/10.1016/B978-1-78242-028-6.00031-4
Petrovic M (2003) Analysis and removal of emerging contaminants in wastewater and drinking water. TrAC Trends Anal Chem 22:685–696. https://doi.org/10.1016/S0165-9936(03)01105-1
Rule KL, Ebbett VR, Vikesland PJ (2005) Formation of chloroform and chlorinated organics by free-chlorine-mediated oxidation of triclosan. Environ Sci Technol 39:3176–3185. https://doi.org/10.1021/es048943+
Sabaliunas D, Webb SF, Hauk A et al (2003) Environmental fate of triclosan in the River Aire Basin, UK. Water Res 37:3145–3154. https://doi.org/10.1016/S0043-1354(03)00164-7
Sanchez-Prado L, Barro R, Garcia-Jares C et al (2008) Sonochemical degradation of triclosan in water and wastewater. Ultrason Sonochem 15:689–694. https://doi.org/10.1016/j.ultsonch.2008.01.007
Serna-Galvis EA, Silva-Agredo J, Giraldo-Aguirre AL, Torres-Palma RA (2015) Sonochemical degradation of the pharmaceutical fluoxetine: effect of parameters, organic and inorganic additives and combination with a biological system. Sci Total Environ 524–525:354–360. https://doi.org/10.1016/j.scitotenv.2015.04.053
Serpone N, Terzian R, Hidaka H, Pelizzetti E (1994) Ultrasonic induced dehalogenation and oxidation of 2-, 3-, and 4-chlorophenol in air-equilibrated aqueous media. Similarities with irradiated semiconductor particulates. J Phys Chem 98:2634–2640. https://doi.org/10.1021/j100061a021
Sirés I, Oturan N, Oturan MA et al (2007) Electro-Fenton degradation of antimicrobials triclosan and triclocarban. Electrochim Acta 52:5493–5503. https://doi.org/10.1016/j.electacta.2007.03.011
Son HS, Ko G, Zoh KD (2009) Kinetics and mechanism of photolysis and TiO2 photocatalysis of triclosan. J Hazard Mater 166:954–960. https://doi.org/10.1016/j.jhazmat.2008.11.107
Song Z, Wang N, Zhu L et al (2012) Efficient oxidative degradation of triclosan by using an enhanced Fenton-like process. Chem Eng J 198–199:379–387. https://doi.org/10.1016/j.cej.2012.05.067
Stamatis N, Antonopoulou M, Hela D, Konstantinou I (2014) Photocatalytic degradation kinetics and mechanisms of antibacterial triclosan in aqueous TiO 2 suspensions under simulated solar irradiation. J Chem Technol Biotechnol 89:1145–1154. https://doi.org/10.1002/jctb.4387
Summoogum SL, Altarawneh M, Mackie JC et al (2012) Oxidation of dibenzo-p-dioxin: formation of initial products, 2-methylbenzofuran and 3-hydro-2-methylenebenzofuran. Combust Flame 159:3056–3065. https://doi.org/10.1016/j.combustflame.2012.05.004
Thangavadivel K, Megharaj M, Mudhoo A, Naidu R (2012) Degradation of organic pollutants using ultrasound. Handb Appl Ultrason Sonochem Sustain 447–474. doi:https://doi.org/10.1201/b11012-19
Tohidi F, Cai Z (2015) GC/MS analysis of triclosan and its degradation by-products in wastewater and sludge samples from different treatments. Environ Sci Pollut Res Int. https://doi.org/10.1007/s11356-015-4289-x
van Iersel MM, Benes NE, Keurentjes JTF (2008) Importance of acoustic shielding in sonochemistry. Ultrason Sonochem 15:294–300. https://doi.org/10.1016/j.ultsonch.2007.09.015
Wong-Wah-Chung P, Rafqah S, Voyard G, Sarakha M (2007) Photochemical behaviour of triclosan in aqueous solutions: kinetic and analytical studies. J Photochem Photobiol A Chem 191:201–208. https://doi.org/10.1016/j.jphotochem.2007.04.024
Wu Q, Shi H, Adams CD et al (2012) Oxidative removal of selected endocrine-disruptors and pharmaceuticals in drinking water treatment systems, and identification of degradation products of triclosan. Sci Total Environ 439:18–25. https://doi.org/10.1016/j.scitotenv.2012.08.090
Xiao R, Diaz-rivera D, He Z, Weavers LK (2013a) Using pulsed wave ultrasound to evaluate the suitability of hydroxyl radical scavengers in sonochemical systems. Ultrason Sonochem 20:990–996. https://doi.org/10.1016/j.ultsonch.2012.11.012
Xiao R, Diaz-Rivera D, Weavers LK (2013b) Factors influencing pharmaceutical and personal care product degradation in aqueous solution using pulsed wave ultrasound. Ind Eng Chem Res 52:2824–2831. https://doi.org/10.1021/ie303052a
Xiao R, Wei Z, Chen D, Weavers LK (2014) Kinetics and mechanism of sonochemical degradation of pharmaceuticals in municipal wastewater. Environ Sci Technol 48:9675–9683. https://doi.org/10.1021/es5016197
Yang L, Rathman JF, Weavers LK (2005) Degradation of alkylbenzene sulfonate surfactants by pulsed ultrasound. J Phys Chem B 109:16203–16209. https://doi.org/10.1021/jp0523221
Yu JC, Kwong TY, Luo Q, Cai Z (2006) Photocatalytic oxidation of triclosan. Chemosphere 65:390–399. https://doi.org/10.1016/j.chemosphere.2006.02.011
Zúñiga-Benítez H, Soltan J, Peñuela GA (2016) Application of ultrasound for degradation of benzophenone-3 in aqueous solutions. Int J Environ Sci Technol 13:77–86. https://doi.org/10.1007/s13762-015-0842-x
Acknowledgments
The authors wish to thank NSERC, the Canadian Bureau for International Education (CBIE), and the ELAP program; the Colombian Administrative Department of Science, Technology and Innovation (COLCIENCIAS); the University of Saskatchewan; and the University of Antioquia for the support of this work.
Author information
Authors and Affiliations
Corresponding author
Additional information
Responsible editor: Vítor Pais Vilar
Electronic supplementary material
ESM 1
(DOCX 2483 kb)
Rights and permissions
About this article
Cite this article
Vega, L.P., Soltan, J. & Peñuela, G.A. Sonochemical degradation of triclosan in water in a multifrequency reactor. Environ Sci Pollut Res 26, 4450–4461 (2019). https://doi.org/10.1007/s11356-018-1281-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11356-018-1281-2