Degradación electroquímica indirecta de acetaminofén: desempeño del proceso, trasformaciones y efectos de matriz
DOI:
https://doi.org/10.17533/udea.redin.20211166Palabras clave:
Electroquímica, Cloración, Medicamentos, tratamiento de aguas residualesResumen
El acetaminofén (ACE), un farmacéutico muy consumido en todo el mundo; fue degradado en matrices acuosas por oxidación con especies reactivas de cloro (ERC) electro-generadas usando electrodos de Ti/IrO2. A pesar de que este contaminante ha sido tratado extensamente mediante técnicas electroquímicas, se tiene poca información sobre su degradación en orina por ERC electrogeneradas fresca, y sobre la comprensión de sus transformaciones usando análisis de carga atómica. En este trabajo se discutieron estos dos temas. Inicialmente, se evaluó el efecto de la corriente (10-40 mA) y electrolito soporte (considerando iones típicos del agua superficial y la orina (Cl- y SO42-)), sobre el sistema electroquímico. Luego se describieron la cinética de oxidación y transformaciones primarias de ACE. Se encontró que, en agua destilada, el proceso a 40 mA y en presencia de NaCl condujo al 100% de degradación de ACE en 10 min de tratamiento (0.056 Ah L-1). Los análisis teóricos de la carga atómica sobre ACE indicaron que el grupo amida es el más susceptible a los ataques de las ERC como el HOCl. Por otro lado, la degradación del acetaminofén en orina fresca sintética fue mucho más lenta (21% de remoción de 60 min de tratamiento) que en agua destilada. Esto debido a que las otras sustancias en la matriz de la orina inducen una competencia por las ERC.
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D. M. Whitacre, Reviews of Environmental Contamination and Toxicology, 202nd ed. New York, NY: Springer New York, 2010.
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,” Journal of Hazardous Material, vol. 187, no. 1-3, Mar. 15, 2011. [Online]. Available: https://doi.org/10.1016/j.jhazmat.2011.01.057
J. Rivera-Utrilla, M. Sánchez-Polo, M. A. 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, Oct. 2013. [Online]. Available: https://doi.org/10.1016/j.chemosphere.2013.07.059
P. Verlicchi, M. A. Aukidy, and E. Zambello, “Occurrence of pharmaceutical compounds in urban wastewater: Removal, mass load and environmental risk after a secondary treatment—a review,” Science of The Total Environment, vol. 429, Jul. 01, 2012. [Online]. Available: https://doi.org/10.1016/j.scitotenv.2012.04.028
W. Sim, J. W. Lee, E. S. Lee, S. K. Shin, S. R. Hwang, and et. al, “Occurrence and distribution of pharmaceuticals in wastewater from households, livestock farms, hospitals and pharmaceutical manufactures,” Chemosphere, vol. 82, no. 2, Jan. 2011. [Online]. Available: https://doi.org/10.1016/j.chemosphere.2010.10.026
J. G. M. Bessems and N. P. E. Vermeulen, “Paracetamol (acetaminophen)-induced toxicity: molecular and biochemical mechanisms, analogues and protective approaches,” Critical Reviews in Toxicology, vol. 31, no. 1, Jan. 2001. [Online]. Available: https://doi.org/10.1080/20014091111677
H. Jaeschke and M. L. Bajt, “Intracellular signaling mechanisms of acetaminophen-induced liver cell death,” Toxicological Sciences, vol. 89, no. 1, Jan. 2006. [Online]. Available: https://doi.org/10.1093/toxsci/kfi336
B. Manu, S. Mahamood, H. Vittal, and S. Shrihari, “A novel catalytic route to degrade paracetamol by fenton process,” International Journal of Research in Chemistry and Environment, vol. 1, no. 1, Jul. 01, 2011. [Online]. Available: t.ly/PuZK
R. Andreozzi, V. Caprio, R. Marotta, and D. Vogna, “Paracetamol oxidation from aqueous solutions by means of ozonation and h2o2/uv system,” Water Research, vol. 37, no. 5, Mar. 2003. [Online]. Available: https://doi.org/10.1016/S0043-1354(02)00460-8
M. Stucchi, M. G. Rigamonti, D. Carnevali, and D. C. Boffito, “A kinetic study on the degradation of acetaminophen and amoxicillin in water by ultrasound,” ChemistrySelect, vol. 5, no. 47, Dec. 17, 2020. [Online]. Available: https://doi.org/10.1002/slct.202004147
X. Zhang, F. Wu, X. Wu, P. Chen, and N. Deng, “Photodegradation of acetaminophen in tio2 suspended solution,” Journal of Hazardous Materials, vol. 157, no. 2-3, Sep. 2008. [Online]. Available: https://doi.org/10.1016/j.jhazmat.2007.12.098
J. J. Pignatello, E. Oliveros, and A. Mackay, “Advanced oxidation processes for organic contaminant destruction based on the fenton reaction and related chemistry,” Critical Reviews in Environmental Science and Technology, vol. 36, no. 1, 2006. [Online]. Available: https://doi.org/10.1080/10643380500326564
L. Yang, L. E. Yu, and M. B. Ray, “Degradation of paracetamol in aqueous solutions by tio2 photocatalysis,” Water Research, vol. 42, no. 13, Jul. 2008. [Online]. Available: https://doi.org/10.1016/j.watres.2008.04.023
I. Sirés and E. Brillas, “Remediation of water pollution caused by pharmaceutical residues based on electrochemical separation and degradation technologies: A review,” Environment International, vol. 40, Apr. 2012. [Online]. Available: https://doi.org/10.1016/j.envint.2011.07.012
M. Panizza and G. Cerisol, “Direct and mediated anodic oxidation of organic pollutants,” Chem. Rev., vol. 109, no. 12, Aug. 06, 2009. [Online]. Available: https://doi.org/10.1021/cr9001319
F. Zaviska, P. Drogui, J. Blais, G. Mercier, and S. D. L. R. d’Auzay, “Electrochemical oxidation of chlortetracycline using ti/iro2 and ti/pbo2 anode electrodes: Application of experimental design methodology,” Journal of Environmental Engineering, vol. 139, no. 6, Jun. 2013. [Online]. Available: https://doi.org/10.1061/(ASCE)EE.1943-7870.0000686
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/iro2 anodes: Evaluation of degradation routes, organic by-products and effects of water matrix components,” Chemical Engineering Journal, vol. 279, Nov. 01, 2015. [Online]. Available: https://doi.org/10.1016/j.cej.2015.04.140
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,” Journal of Hazardous Materials, vol. 278, Aug. 15, 2014. [Online]. Available: https://doi.org/10.1016/j.jhazmat.2014.05.076
I. Sirés, E. Brillas, M. A. Oturan, M. A. Rodrigo, and M. Panizza, “Electrochemical advanced oxidation processes: today and tomorrow. a review,” Environmental Science and Pollution Research, vol. 21, Apr. 02, 2014. [Online]. Available: https://doi.org/10.1016/j.jhazmat.2014.05.076
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,” Applied Catalysis B: Environmental, vol. 202, Mar. 2017. [Online]. Available: https://doi.org/10.1016/j.apcatb.2016.08.037
R. E. Palma-Goyes, E. A. Serna-Galvis, J. E. Ramirez, and R. A. Torres-Palma, “Electrochemical degradation of naproxen (npx) and diclofenac (dfc) through active chlorine species (cl2-active): Considerations on structural aspects and degradation in urine,” ECS Transactions, vol. 100, no. 1, 2021. [Online]. Available: https://doi.org/10.1149/10001.0055ecst
D. C. de Moura, C. K. C. de Araújo, C. L. P. S. Zanta, R. Salazar, and C. A. Martínez-Huitle, “Active chlorine species electrogenerated on ti/ru0.3ti0.7o2 surface: Electrochemical behavior, concentration determination and their application,” Journal of Electroanalytical Chemistry, vol. 731, 2014. [Online]. Available: https://doi.org/10.1016/j.jelechem.2014.08.008
M. Deborde and U. von Gunten, “Reactions of chlorine with inorganic and organic compounds during water treatment—kinetics and mechanisms: A critical review,” Water Research, vol. 42, no. 1-2, Jan. 2008. [Online]. Available: https://doi.org/10.1016/j.watres.2007.07.025
M. Luna-Trujillo, R. E. 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,” Journal of Electroanalytical Chemistry, vol. 878, Dec. 01, 2020. [Online]. Available: https://doi.org/10.1016/j.jelechem.2020.114661
R. E. Palma-Goyes, J. Vazquez-Arenas, C. Ostos, A. Manzo-Robledo, I. Romero-Ibarra, and et. al, “In search of the active chlorine species on ti/zro2-ruo2-sb2o3 anodes using dems and xps,” Electrochimica Acta, vol. 275, Jun. 2018. [Online]. Available: https://doi.org/10.1016/j.electacta.2018.04.114
R. E. Palma-Goyes, J. Macías, I. González, and R. A. Torres-Palma, “Tratamiento de aguas residuales provenientes de la industria textil mediante oxidación electroquímica,” Rev. Colomb. Mater., no. 4, Apr. 2013. [Online]. Available: https://revistas.udea.edu.co/index.php/materiales/article/view/15085/13162
A. L. G. Aguirre, E. D. E. Erazo, O. A. F. Acosta, E. A. S. Galvis, and R. A. Torres-Palma, “Tratamiento electroquímico de aguas que contienen antibióticos β-lactámicos,” Ciencia en Desarrollo, vol. 7, no. 1, Jan-Jun. 2016. [Online]. Available: https://doi.org/10.19053/01217488.4227
M. L. Zavala and E. E. 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, 2016. [Online]. Available: https://doi.org/10.3390/w8090383
M. A. López, D. A. Vega, J. M. Álvarez, O. F. Castillo, and R. A. Cantú, “Electrochemical oxidation of acetaminophen and its transformation products in surface water: effect of ph and current density,” Heliyon, vol. 6, no. 2, Feb. 08, 2020. [Online]. Available: https://doi.org/10.1016/j.heliyon.2020.e03394
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,” Journal of Applied Electrochemistry, vol. 42, 2012. [Online]. Available: https://doi.org/10.1007/s10800-012-0444-y
M. C. Bhowmik, M. Misbahuddin, and H. A. Bhuiyan, “Estimation of paracetamol in urine to assess the diurnal variation,” Bangabandhu Sheikh Mujib Medical University Journal, vol. 11, no. 2, May. 30, 2018. [Online]. Available: https://doi.org/10.3329/bsmmuj.v11i2.36780
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,” Journal of Environmental Chemical Engineering, vol. 8, no. 5, Oct. 2020. [Online]. Available: https://doi.org/10.1016/j.jece.2020.104357
Atomic Charge Calculator, Web Chemistry, Czech Republic. [Online]. Available: https://webchem.ncbr.muni.cz/Platform/ChargeCalculator
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,” Chemical Engineering Journal, vol. 315, no. 1, May. 01, 2017. [Online]. Available: https://doi.org/10.1016/j.cej.2017.01.062
L. A. Perea, R. E. Palma-Goyes, J. Vásquez-arenas, I. Romero-Ibarra, C. Ostos, and et al., “Efficient cephalexin degradation using active chlorine produced on ruthenium and iridium oxide anodes: Role of bath composition, analysis of degradation pathways and degradation extent,” Science of The Total Environment, vol. 648, Jan. 15, 2019. [Online]. Available: https://doi.org/10.1016/j.scitotenv.2018.08.148
C. Comninellis and G. Chen, Electrochemistry for the Environment, 1st ed. New York, NY: Springer, 2010.
A. Kraft, M. Stadelmann, M. Blaschke, D. Kreysig, B. Sandt, and et al., “Electrochemical water disinfection part i: Hypochlorite production from very dilute chloride solutions,” Journal of Applied Electrochemistry, vol. 29, 1999. [Online]. Available: https://doi.org/10.1023/A:1003650220511
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,” Journal of Applied Electrochemistry, vol. 22, 1992. [Online]. Available: https://doi.org/10.1007/BF01092683
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, 2004. [Online]. Available: https://doi.org/10.1021/es035368l
M. Bedner and W. A. MacCrehan, “Transformation of acetaminophen by chlorination produces the toxicants 1,4-benzoquinone and N-acetyl-p-benzoquinone iminen,” Environ. Sci. Technol., vol. 40, no. 2, 2006. [Online]. Available: https://doi.org/10.1021/es0509073
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,” Journal of Water Supply: Research and Technology-Aqua, vol. 57, no. 6, 2008. [Online]. Available: https://doi.org/10.2166/aqua.2008.095
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, Aug. 13, 2009. [Online]. Available: https://doi.org/10.1021/es9002422
F. Cao, M. Zhang, S. Yuan, J. Fenga, Q. Wang, and et al., “Transformation of acetaminophen during water chlorination treatment: kinetics and transformation products identification,” Environ Sci Pollut Res, vol. 23, 2016. [Online]. Available: https://doi.org/10.1007/s11356-016-6341-x
Calculation of Molecular Properties and Bioactivity Score, Molinspiration Cheminformatics. [Online]. Available: https://www.molinspiration.com/cgi-bin/properties
G. Barassi and T. Borrmann, “N-chlorination and orton rearrangement of aromatic polyamides, revisited,” J. Memb. Sci. Technol., vol. 2, no. 2, 2012. [Online]. Available: https://doi.org/10.4172/2155-9589.1000115
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,” PNAS, vol. 81, no. 5, Mar. 01, 1984. [Online]. Available: https://doi.org/10.1073/pnas.81.5.1327
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, 2018. [Online]. Available: https://doi.org/10.3390/ijerph15122637
J. T. Trevors and J. Basaraba, “Toxicity of benzoquinone and hydroquinone in short-term bacterial bioassays,” Bull. Environ. Contam. Toxicol., vol. 25, 1980. [Online]. Available: https://doi.org/10.1007/BF01985590
E. R. Blatchley and M. Cheng, “Reaction mechanism for chlorination of urea,” Environ. Sci. Technol., vol. 44, no. 22, 2010. [Online]. Available: https://doi.org/10.1021/es102423u
M. S. Rayson, M. Altarawneh, J. C. Mackie, E. M. Kennedy, and B. Z. Dlugogorski, “Theoretical study of the ammonia−hypochlorous acid reaction mechanism,” J. Phys. Chem. A, vol. 114, no. 7, 2010. [Online]. Available: https://doi.org/10.1021/jp9088657
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