Indirect electrochemical degradation of acetaminophen: process performance, pollutant transformation, and matrix effects evaluation
DOI:
https://doi.org/10.17533/udea.redin.20211166Keywords:
Electrochemistry, Chlorination, Pharmaceuticals, Water treatmentAbstract
Acetaminophen (ACE), a highly consumed pharmaceutical, was degraded in aqueous matrices by reactive chlorine species (RCS) electrogenerated using Ti/IrO2 electrodes. Although this pollutant has been extensively treated by electrochemical techniques, little information is known about its degradation in fresh urine by electrogenerated RCS, and the understanding of its transformations using analyses of atomic charge. In this work, these two topics were discussed. Initially, the effect of current (10-40 mA) and supporting electrolyte (considering typical ions present in surface water and urine (Cl- and SO42-)) on the electrochemical system was evaluated. Then, the kinetics and primary transformations products involved in the elimination of ACE were described. It was found that, in distilled water, the process at 40 mA in NaCl presence led to 100 % of ACE degradation (10 min, 0.056 Ah L-1). Theoretical analyses of atomic charge for ACE indicated that the amide group is the most susceptible to attacks by RCS such as HOCl. On the other hand, degradation of acetaminophen in synthetic fresh urine was slower (21% of degradation after 60 min of treatment) than in distilled water. This was attributed to the other substances in the urine matrix, which induce competition for the degrading RCS.
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References
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[30] A. E. Yañez-Rios, J. E. Carrera-Crespo, R. M. Luna-Sanchez, R. E. Palma-Goyes, and J. Vazquez-Arenas, “The influence of pH and current density on an UV254 photo-assisted electrochemical process generating active chlorine and radicals for efficient and rapid ciprofloxacin mineralization compared to individual techniques,” J. Environ. Chem. Eng., vol. 8, no. 5, pp. 104357, 2020.
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[45] J. T. Trevors and J. Basaraba, “Toxicity of benzoquinone and hydroquinone in short-term bacterial bioassays,” Bull. Environ. Contam. Toxicol., vol. 25, no. 1, pp. 672–675, 1980.
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[47] L. A. Perea, R. E. Palma-Goyes, J. Vazquez-Arenas, I. Romero-Ibarra, C. Ostos, and R. A. Torres-Palma, “Efficient cephalexin degradation using active chlorine produced on ruthenium and iridium oxide anodes: Role of bath composition, analysis of degradation pathways and degradation extent,” Sci. Total Environ., vol. 648, pp.377-387, 2019.
[2] A. Ziylan and N. H. Ince, “The occurrence and fate of anti-inflammatory and analgesic pharmaceuticals in sewage and fresh water: Treatability by conventional and non-conventional processes,” J. Hazard. Mater., vol. 187, no. 1–3, pp. 24–36, 2011.
[3] J. Rivera-Utrilla, M. Sánchez-Polo, M. Á. Ferro-García, G. Prados-Joya, and R. Ocampo-Pérez, “Pharmaceuticals as emerging contaminants and their removal from water. A review.,” Chemosphere, vol. 93, no. 7, pp. 1268–87, 2013.
[4] P. Verlicchi, M. Al Aukidy, and E. Zambello, “Occurrence of pharmaceutical compounds in urban wastewater: Removal, mass load and environmental risk after a secondary treatment-A review,” Sci. Total Environ., vol. 429, pp. 123–155, 2012.
[5] W. Sim, J.-W. Lee, E.-S. Lee, S.-K. Shin, S.-R. Hwang, and J.-E. Oh, “Occurrence and distribution of pharmaceuticals in wastewater from households, livestock farms, hospitals and pharmaceutical manufactures,” Chemosphere, vol. 82, no. 2, pp. 179–186, 2011.
[6] J. G. M. Bessems and N. P. E. Vermeulen, “Paracetamol (Acetaminophen)-Induced Toxicity: Molecular and Biochemical Mechanisms, Analogues and Protective Approaches,” Crit. Rev. Toxicol., vol. 31, no. 1, pp. 55–138, 2001.
[7] H. Jaeschke and M. L. Bajt, “Intracellular signaling mechanisms of acetaminophen-induced liver cell death.,” Toxicol. Sci., vol. 89, no. 1, pp. 31–41, 2006.
[8] B. Manu, S. Mahamood, H. Vittal, and S. Shrihari, “A novel catalytic route to degrade paracetamol by Fenton process,” Int. J. Res. Chem. Environ., vol. 1, no. 1, pp. 157–164, 2011.
[9] R. Andreozzi, V. Caprio, R. Marotta, and D. Vogna, “Paracetamol oxidation from aqueous solutions by means of ozonation and H2O2/UV system,” Water Res., vol. 37, no. 5, pp. 993–1004, 2003.
[10] E. Villaroel, J. Silva-Agredo, C. Petrier, G. Taborda, and R. Torres-Palma, “Ultrasonic degradation of acetaminophen in water: effect of sonochemical parameters and water matrix.,” Ultrason. Sonochem., vol. 21, no. 5, pp. 1763–9, 2014.
[11] X. Zhang, F. Wu, X. Wu, P. Chen, and N. Deng, “Photodegradation of acetaminophen in TiO2 suspended solution,” J. Hazard. Mater., vol. 157, no. 2, pp. 300–307, 2008.
[12] J. J. Pignatello, E. Oliveros, and A. Mackay, “Advanced Oxidation Processes for Organic Contaminant Destruction Based on the Fenton Reaction and Related Chemistry,” Crit. Rev. Environ. Sci. Technol., vol. 36, pp. 1–84, 2006.
[13] L. Yang, L. E. Yu, and M. B. Ray, “Degradation of paracetamol in aqueous solutions by TiO2 photocatalysis,” Water Res., vol. 42, pp. 3480–3488, 2008.
[14] I. Sirés and E. Brillas, “Remediation of water pollution caused by pharmaceutical residues based on electrochemical separation and degradation technologies : A review,” Environ. Int., vol. 40, pp. 212–229, 2012.
[15] M. Panizza and G. Cerisola, “Direct and mediated anodic oxidation of organic pollutants.,” Chem. Rev., vol. 109, no. 12, pp. 6541–69, 2009.
[16] F. Zaviska, P. Drogui, J. Blais, G. Mercier, and S. De La Rochebrochard d’Auzay, “Electrochemical Oxidation of Chlortetracycline Using Ti/IrO2 and Ti/PbO2 Anode Electrodes: Application of Experimental Design Methodology,” J. Environ. Eng. Sci., vol. 139, no. 6, pp. 810–821, 2013.
[17] A. L. Giraldo, E. D. Erazo-Erazo, O. A. Flórez-Acosta, E. A. Serna-Galvis, and R. A. Torres-Palma, “Degradation of the antibiotic oxacillin in water by anodic oxidation with Ti/IrO 2 anodes: Evaluation of degradation routes, organic by-products and effects of water matrix components,” Chem. Eng. J., vol. 279, pp. 103–114, 2015.
[18] F. L. Guzmán-Duque, R. E. Palma-Goyes, I. González, G. Peñuela, and R. a. Torres-Palma, “Relationship between anode material, supporting electrolyte and current density during electrochemical degradation of organic compounds in water,” J. Hazard. Mater., vol. 278, pp. 221–226, 2014.
[19] I. Sirés, E. Brillas, M. A. Oturan, M. A. Rodrigo, and M. Panizza, “Electrochemical advanced oxidation processes: today and tomorrow. A review,” Environ. Sci. Pollut. Res., vol. 21, no. 14, pp. 8336–8367, 2014.
[20] F. C. Moreira, R. A. R. Boaventura, E. Brillas, and V. J. P. Vilar, “Electrochemical advanced oxidation processes: A review on their application to synthetic and real wastewaters,” Appl. Catal. B Environ., vol. 202, pp. 217–261, 2017.
[21] R. E. Palma, E. Serna-Galvis, J. E. Ramirez, and R. A. Torres, “Electrochemical Degradation of Naproxen (NPX) and Diclofenac (DFC) through Active Chlorine Species (Cl 2 -active): Considerations on Structural Aspects and Degradation in Urine,” ECS Trans., vol. 100, no. 1, pp. 55–71, 2021.
[22] D. Chianca de Moura, C. K. Costa de Araújo, C. L. P. S. Zanta, R. Salazar, and C. A. Martínez-Huitle, “Active chlorine species electrogenerated on Ti/Ru0.3Ti0.7O2surface: Electrochemical behavior, concentration determination and their application,” J. Electroanal. Chem., vol. 731, pp. 145–152, 2014.
[23] M. Deborde and U. von Gunten, “Reactions of chlorine with inorganic and organic compounds during water treatment-Kinetics and mechanisms: A critical review,” Water Res., vol. 42, pp. 13–51, 2008.
[24] M. Luna-Trujillo, R. Palma-Goyes, J. Vazquez-Arenas, and A. Manzo-Robledo, “Formation of active chlorine species involving the higher oxide MOx+1 on active Ti/RuO2-IrO2 anodes: A DEMS analysis,” J. Electroanal. Chem., vol. 878, p. 114661, 2020.
[25] R. E. Palma-Goyes et al., “In search of the active chlorine species on Ti/ZrO2-RuO2-Sb2O3 anodes using DEMS and XPS,” Electrochim. Acta, vol. 275, pp. 265–274, 2018.
[26] M. López Zavala and E. Espinoza Estrada, “Degradation of Acetaminophen and Its Transformation Products in Aqueous Solutions by Using an Electrochemical Oxidation Cell with Stainless Steel Electrodes,” Water, vol. 8, no. 9, pp. 383, 2016.
[27] M. Á. López Zavala, D. A. Vega, J. M. Álvarez Vega, O. F. Castillo Jerez, and R. A. Cantú Hernández, “Electrochemical oxidation of acetaminophen and its transformation products in surface water: effect of pH and current density,” Heliyon, vol. 6, no. 2, pp. e03394, 2020.
[28] V. Amstutz, A. Katsaounis, A. Kapalka, C. Comninellis, and K. M. Udert, “Effects of carbonate on the electrolytic removal of ammonia and urea from urine with thermally prepared IrO2 electrodes,” J. Appl. Electrochem., vol. 42, no. 9, pp. 787–795, 2012.
[29] M. C. Bhowmik, M. Misbahuddin, and H. A. Bhuiyan, “Estimation of paracetamol in urine to assess the diurnal variation,” Bangabandhu Sheikh Mujib Med. Univ. J., vol. 11, no. 2, pp. 193, 2018.
[30] A. E. Yañez-Rios, J. E. Carrera-Crespo, R. M. Luna-Sanchez, R. E. Palma-Goyes, and J. Vazquez-Arenas, “The influence of pH and current density on an UV254 photo-assisted electrochemical process generating active chlorine and radicals for efficient and rapid ciprofloxacin mineralization compared to individual techniques,” J. Environ. Chem. Eng., vol. 8, no. 5, pp. 104357, 2020.
[31] D. Sehnal, “AtomicChargeCalculator,” WebChemistry, 2020. https://webchem.ncbr.muni.cz/Platform/ChargeCalculator (accessed Apr. 27, 2020).
[32] E. A. Serna-Galvis, S. D. Jojoa-Sierra, K. E. Berrio-Perlaza, F. Ferraro, and R. A. Torres-Palma, “Structure-reactivity relationship in the degradation of three representative fluoroquinolone antibiotics in water by electrogenerated active chlorine,” Chem. Eng. J., vol. 315, no. April, pp. 552–561, 2017.
[33] C. Comninellis and G. Chen, Electrochemistry for the Environment. New York, NY: Springer New York, 2010.
[34] A. Kraft et al., “Electrochemical water disinfection. Part I: Hypochlorite production from very dilute chloride solutions,” J. Appl. Electrochem., vol. 29, no. 7, pp. 861–868, 1999.
[35] L. R. Czarnetzki and L. J. J. Janssen, “Formation of hypochlorite, chlorate and oxygen during NaCl electrolysis from alkaline solutions at an RuO2/TiO2 anode,” J. Appl. Electrochem., vol. 22, no. 4, pp. 315–324, 1992.
[36] K. E. Pinkston and D. L. Sedlak, “Transformation of aromatic ether- and amine-containing pharmaceuticals during chlorine disinfection,” Environ. Sci. Technol., vol. 38, no. 14, pp. 4019–4025, 2004.
[37] M. Bedner and W. A. MacCrehan, “Transformation of acetaminophen by chlorination produces the toxicants 1,4-benzoquinone and N-acetyl-p-benzoquinone imine,” Environ. Sci. Technol., vol. 40, no. 2, pp. 516–522, 2006.
[38] I. Xagoraraki, R. Hullman, W. Song, H. Li, and T. Voice, “Effect of pH on degradation of acetaminophen and production of 1,4-benzoquinone in water chlorination,” J. Water Supply Res. Technol. - AQUA, vol. 57, no. 6, pp. 381–390, 2008.
[39] J. Lu, Q. Huang, and L. Mao, “Removal of acetaminophen using enzyme-mediated oxidative coupling processes: I. Reaction rates and pathways,” Environ. Sci. Technol., vol. 43, no. 18, pp. 7062–7067, 2009.
[40] F. Cao et al., “Transformation of acetaminophen during water chlorination treatment: kinetics and transformation products identification,” Environ. Sci. Pollut. Res., vol. 23, no. 12, pp. 12303–12311, 2016.
[41] Molinspiration Cheminformatics, “Calculation of LogP,” Molinspiration 2021, 2021. https://www.molinspiration.com/cgi-bin/properties (accessed Jan. 10, 2020).
[42] G. Barassi and T. Borrmann, “N-chlorination and Orton Rearrangement of Aromatic Polyamides, Revisited,” J. Membr. Sci. Technol., vol. 02, no. 02, pp. 2–4, 2012.
[43] D. C. Dahlin, G. T. Miwa, A. Y. H. Lu, and S. D. Nelson, “N-acetyl-p-benzoquinone imine: A cytochrome P-450-mediated oxidation product of acetaminophen,” Isotopenpraxis, vol. 20, no. 1, pp. 1327–1331, 1984.
[44] Y. H. Dao, H. N. Tran, T. T. Tran-Lam, T. Q. Pham, and G. T. Le, “Degradation of paracetamol by an UV/chlorine advanced oxidation process: Influencing factors, factorial design, and intermediates identification,” Int. J. Environ. Res. Public Health, vol. 15, no. 12, pp. 1-18, 2018.
[45] J. T. Trevors and J. Basaraba, “Toxicity of benzoquinone and hydroquinone in short-term bacterial bioassays,” Bull. Environ. Contam. Toxicol., vol. 25, no. 1, pp. 672–675, 1980.
[46] S. D. Jojoa-Sierra, J. Silva-Agredo, E. Herrera-Calderon, and R. A. Torres-Palma, “Elimination of the antibiotic norfloxacin in municipal wastewater, urine and seawater by electrochemical oxidation on IrO2 anodes,” Sci. Total Environ., vol. 575, pp. 1228–1238, 2017.
[47] L. A. Perea, R. E. Palma-Goyes, J. Vazquez-Arenas, I. Romero-Ibarra, C. Ostos, and R. A. Torres-Palma, “Efficient cephalexin degradation using active chlorine produced on ruthenium and iridium oxide anodes: Role of bath composition, analysis of degradation pathways and degradation extent,” Sci. Total Environ., vol. 648, pp.377-387, 2019.
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2021-11-09
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Serna-Galvis, E. A. ., Palma-Goyes, . R. E., Torres-Palma, R. A., & Ramírez, J. E. (2021). Indirect electrochemical degradation of acetaminophen: process performance, pollutant transformation, and matrix effects evaluation. Revista Facultad De Ingeniería Universidad De Antioquia. https://doi.org/10.17533/udea.redin.20211166
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