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Photo-Fenton oxidation of 3-amino-5-methylisoxazole: a by-product from biological breakdown of some pharmaceutical compounds

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Abstract

The present study aims to assess the removal of 3-amino-5-methylisoxazole (AMI), a recalcitrant by-product resulting from the biological breakdown of some pharmaceuticals, applying a solar photo-Fenton process assisted by ferrioxalate complexes (SPFF) (Fe3+/H2O2/oxalic acid/UVA-Vis) and classical solar photo-Fenton process (SPF) (Fe2+/H2O2/UVA-Vis). The oxidation ability of SPFF was evaluated at different iron/oxalate molar ratios (1:3, 1:6, and 1:9, with [total iron] = 3.58 × 10−2 mM and [oxalic acid] = 1.07 × 10−1, 2.14 × 10−1 and 3.22 × 10−1 mM, respectively) and pH values (3.5–6.5), using low iron contents (2.0 mg Fe3+ L−1). Additionally, the use of other organic ligands such as citrate and ethylenediamine-N,N′-disuccinic acid (EDDS) was tested. The oxidation power of the classical SPF was assessed at different pH values (2.8–4.0) using 2.0 mg Fe2+ per liter. Furthermore, the effect of AMI concentration (2–20 mg L−1), presence of inorganic ions (Cl−, SO4 2−, NO3 −, HCO3 −, NH4 +), and radical scavengers (sodium azide and D-mannitol) on the SPF method at pH 3.5 was also assessed. Experiments were done using a lab-scale photoreactor with a compound parabolic collector (CPC) under simulated solar radiation. A pilot-scale assay was conducted using the best operation conditions. While at near neutral pH, an iron/oxalate molar ratio of 1:9 led to the removal of 72 % of AMI after 90 min of SPFF, at pH 3.5, an iron/oxalate molar ratio of 1:3 was enough to achieve complete AMI degradation (below the detection limit) after 30 min of reaction. The SPF process at pH 3.5 underwent a slower AMI degradation, reaching total AMI degradation after 40 min of reaction. The scale up of SPF process showed a good reproducibility. Oxalic and oxamic acids were identified as the main low-molecular-weight carboxylic acids detected during the pilot-scale SPF reaction.

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References

  • Andreozzi R, Caprio V, Insola A, Marotta R (1999) Advanced oxidation processes (AOP) for water purification and recovery. Catal Today 53:51–59

    Article  CAS  Google Scholar 

  • Balmer ME, Sulzberger B (1999) Atrazine degradation in irradiated iron/oxalate systems: effects of pH and oxalate. Environ Sci Technol 33:2418–2424

    Article  CAS  Google Scholar 

  • Bernabeu A, Vercher RF, Santos-Juanes L, Simón PJ, Lardín C, Martínez MA, Vicente JA, González R, Llosá C, Arques A, Amat AM (2011) Solar photocatalysis as a tertiary treatment to remove emerging pollutants from wastewater treatment plant effluents. Catal Today 161:235–240

    Article  CAS  Google Scholar 

  • Boreen AL, Arnold WA, McNeill K (2004) Photochemical fate of sulfa drugs in the aquatic environment: sulfa drugs containing five-membered heterocyclic groups. Environ Sci Technol 38:3933–3940

    Article  CAS  Google Scholar 

  • Buxton GV, Greenstock CL, Helman WP, Ross AB (1988) Critical review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals.OH/.O- in aqueous solution. J Phys Chem Ref Data 17:513–886

    Article  CAS  Google Scholar 

  • Cheng H-P, Huang Y-H, Lee C (2011) Decolorization of reactive dye using a photo-ferrioxalate system with brick grain-supported iron oxide. J Hazard Mater 188:357–362

    Article  CAS  Google Scholar 

  • De la Cruz N, Esquius L, Grandjean D, Magnet A, Tungler A, de Alencastro LF, Pulgarín C (2013) Degradation of emergent contaminants by UV, UV/H2O2 and neutral photo-Fenton at pilot scale in a domestic wastewater treatment plant. Water Res 47:5836–5845

    Article  Google Scholar 

  • Dias IN, Souza BS, Pereira JHOS, Moreira FC, Dezotti M, Boaventura RAR, Vilar VJP (2014) Enhancement of the photo-Fenton reaction at near neutral pH through the use of ferrioxalate complexes: a case study on trimethoprim and sulfamethoxazole antibiotics removal from aqueous solutions. Chem Eng J 247:302–313

    Article  CAS  Google Scholar 

  • Dirany A, Sirés I, Oturan N, Oturan MA (2010) Electrochemical abatement of the antibiotic sulfamethoxazole from water. Chemosphere 81:594–602

    Article  CAS  Google Scholar 

  • Epold I, Dulova N, Veressinina Y, Trapido M (2012) Application of ozonation, UV photolysis, Fenton treatment and other related processes for degradation of ibuprofen and sulfamethoxazole in different aqueous matrices. J Adv Oxid Technol 15:354–364

    CAS  Google Scholar 

  • Faust BC, Hoigné J (1990) Photolysis of Fe (III)-hydroxy complexes as sources of OH radicals in clouds, fog and rain. Atmos Environ Part A 24:79–89

    Article  Google Scholar 

  • Faust BC, Zepp RG (1993) Photochemistry of aqueous iron(III)-polycarboxylate complexes: roles in the chemistry of atmospheric and surface waters. Environ Sci Technol 27:2517–2522

    Article  CAS  Google Scholar 

  • Gao P, Munir M, Xagoraraki I (2012) Correlation of tetracycline and sulfonamide antibiotics with corresponding resistance genes and resistant bacteria in a conventional municipal wastewater treatment plant. Sci Total Environ 421–422:173–183

    Article  Google Scholar 

  • Gonçalves AG, Órfão JJM, Pereira MFR (2012) Catalytic ozonation of sulphamethoxazole in the presence of carbon materials: catalytic performance and reaction pathways. J Hazard Mater 239–240:167–174

    Article  Google Scholar 

  • Gonzalez M, Hashem T, Jakob L, Braum A (1995) Oxidative degradation of nitrogen-containing organic compounds: vaccum-ultraviolet (VUV) photolysis of aqueous solutions of 3-amino 5-methylisoxazole. Fresenius J Anal Chem 351:92–97

    Article  CAS  Google Scholar 

  • Gonzalez MG, Oliveros E, Wörner M, Braun AM (2004) Vacuum-ultraviolet photolysis of aqueous reaction systems. J Photochem Photobiol C: Photochem Rev 5:225–246

    Article  CAS  Google Scholar 

  • Grebel JE, Pignatello JJ, Mitch WA (2010) Effect of halide ions and carbonates on organic contaminant degradation by hydroxyl radical-based advanced oxidation processes in saline waters. Environ Sci Technol 44:6822–6828

    Article  CAS  Google Scholar 

  • Hamm RE, Shull CM, Grant DM (1954) Citrate complexes with iron(II) and iron(III). J Am Chem Soc 76:2111–2114

    Article  CAS  Google Scholar 

  • Hirakawa K, Mori M, Yoshida M, Oikawa S, Kawanishi S (2004) Photo-irradiated titanium dioxide catalyzes site specific DNA damage via generation of hydrogen peroxide. Free Radic Res 38:439–447

    Article  CAS  Google Scholar 

  • Huang W, Brigante M, Wu F, Hanna K, Mailhot G (2012) Development of a new homogenous photo-Fenton process using Fe(III)-EDDS complexes. J Photochem Photobiol A Chem 239:17–23

    Article  CAS  Google Scholar 

  • Huang W, Brigante M, Wu F, Mousty C, Hanna K, Mailhot G (2013) Assessment of the Fe(III)–EDDS complex in Fenton-like processes: from the radical formation to the degradation of bisphenol A. Environ Sci Technol 47:1952–1959

    Article  CAS  Google Scholar 

  • Jaiswal M, Khadikar PV, Supuran CT (2004) Topological modeling of lipophilicity, diuretic activity, and carbonic inhibition activity of benzene sulfonamides: a molecular connectivity approach. Bioorg Med Chem Lett 14:5661–5666

    Article  CAS  Google Scholar 

  • Joss A, Keller E, Alder AC, Göbel A, McArdell CS, Ternes T, Siegrist H (2005) Removal of pharmaceuticals and fragrances in biological wastewater treatment. Water Res 39:3139–3152

    Article  CAS  Google Scholar 

  • Klamerth N, Malato S, Maldonado MI, Agüera A, Fernández-Alba A (2011) Modified photo-Fenton for degradation of emerging contaminants in municipal wastewater effluents. Catal Today 161:241–246

    Article  CAS  Google Scholar 

  • Klamerth N, Malato S, Agüera A, Fernández-Alba A (2013) Photo-Fenton and modified photo-Fenton at neutral pH for the treatment of emerging contaminants in wastewater treatment plant effluents: a comparison. Water Res 47:833–840

    Article  CAS  Google Scholar 

  • Knight RJ, Sylva RN (1975) Spectrophotometric investigation of iron(III) hydrolysis in light and heavy water at 25°C. J Inorg Nucl Chem 37:779–783

    Article  CAS  Google Scholar 

  • Korzeniewska E, Korzeniewska A, Harnisz M (2013) Antibiotic resistant Escherichia coli in hospital and municipal sewage and their emission to the environment. Ecotoxicol Environ Saf 91:96–102

    Article  CAS  Google Scholar 

  • Kumar M, Ramasamy K, Mani V, Mishra RK, Majeed ABA, Clercq ED, Narasimhan B (2012) Synthesis, antimicrobial, anticancer, antiviral evaluation and QSAR studies of 4-(1-aryl-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzene sulfonamides. Arab J Chem

  • Kümmerer K (2009) Antibiotics in the aquatic environment–a review–part I. Chemosphere 75:417–434

    Article  Google Scholar 

  • Le-Minh N, Khan SJ, Drewes JE, Stuetz RM (2010) Fate of antibiotics during municipal water recycling treatment processes. Water Res 44:4295–4323

    Article  CAS  Google Scholar 

  • Lee SO (2005) Dissolution of iron oxides by oxalic acid. University of New South Wales

  • Li J, Mailhot G, Wu F, Deng N (2010) Photochemical efficiency of Fe(III)-EDDS complex: OH radical production and 17β-estradiol degradation. J Photochem Photobiol A Chem 212:1–7

    Article  CAS  Google Scholar 

  • Lin K, Gan J (2011) Sorption and degradation of wastewater-associated non-steroidal anti-inflammatory drugs and antibiotics in soils. Chemosphere 83:240–246

    Article  CAS  Google Scholar 

  • Manenti DR, Soares PA, Módenes AN, Espinoza-Quiñones FR, Boaventura RAR, Bergamasco R, Vilar VJP (2015) Insights into solar photo-Fenton process using iron(III)–organic ligand complexes applied to real textile wastewater treatment. Chem Eng J 266:203–212

    Article  CAS  Google Scholar 

  • Manu B, Mahamood (2012) Degradation kinetics of diclofenac in water by Fenton’s oxidation. J Sust Energ Environ 3:173–176

    Google Scholar 

  • Marciocha D, Kalka J, Turek-Szytow J, Wiszniowski J, Surmacz-Gorska J (2009) Oxidation of sulfamethoxazole by UVA radiation and modified Fenton reagent: toxicity and biodegradability of by-products. Water Sci Technol 60:2555–2562

    Article  CAS  Google Scholar 

  • Massacesi M, Ponticelli G, Maxia V, Serci S (1981) 2,5-Diphenyloxazole, 3,5-diphenylisoxazole and 3-amino, 5-methylisoxazole complexes with iron(III) salts. Spectrochim Acta A: Mol Spectrosc 37:1035–1040

    Article  Google Scholar 

  • Michael I, Rizzo L, McArdell CS, Manaia CM, Merlin C, Schwartz T, Dagot C, Fatta-Kassinos D (2013) Urban wastewater treatment plants as hotspots for the release of antibiotics in the environment: a review. Water Res 47:957–995

    Article  CAS  Google Scholar 

  • Miralles-Cuevas S, Arqués A, Maldonado MI, Sánchez-Pérez JA, Malato Rodríguez S (2013) Combined nanofiltration and photo-Fenton treatment of water containing micropollutants. Chem Eng J 224:89–95

    Article  CAS  Google Scholar 

  • Monteagudo JM, Durán A, Aguirre M, Martín IS (2010) Photodegradation of reactive blue 4 solutions under ferrioxalate-assisted UV/solar photo-Fenton system with continuous addition of H2O2 and air injection. Chem Eng J 162:702–709

    Article  CAS  Google Scholar 

  • Nasuhoglu D, Yargeau V, Berk D (2011) Photo-removal of sulfamethoxazole (SMX) by photolytic and photocatalytic processes in a batch reactor under UV-C radiation (λmax = 254nm). J Hazard Mater 186:67–75

    Article  CAS  Google Scholar 

  • Orama M, Hyvonen H, Saarinen H, Aksela R (2002) Complexation of [S,S] and mixed stereoisomers of N,N’-ethylenediaminedisuccinic acid (EDDS) with Fe(III), Cu(II), Zn(II) and Mn(II) ions in aqueous solution. J Chem Soc Dalton Trans 4644-4648

  • Panias D, Taxiarchou M, Douni I, Paspaliaris I, Kontopoulos A (1996) Thermodynamic analysis of the reactions of iron oxides: dissolution in oxalic acid. Can Metall Q 35:363–373

    Article  CAS  Google Scholar 

  • Pereira JOS, Reis A, Nunes O, Borges M, Vilar VP, Boaventura RR (2014) Assessment of solar driven TiO2-assisted photocatalysis efficiency on amoxicillin degradation. Environ Sci Pollut Res 21:1292–1303

    Article  CAS  Google Scholar 

  • Pérez-González A, Urtiaga AM, Ibáñez R, Ortiz I (2012) State of the art and review on the treatment technologies of water reverse osmosis concentrates. Water Res 46:267–283

    Article  Google Scholar 

  • Pignatello J, Oliveros E, MacKay A (2006) Advanced oxidation processes for organic contaminant destruction based on the Fenton reaction and related chemistry. Crit Rev Environ Sci Technol 36:1–84

    Article  CAS  Google Scholar 

  • Plósz BG, Leknes H, Liltved H, Thomas KV (2010) Diurnal variations in the occurrence and the fate of hormones and antibiotics in activated sludge wastewater treatment in Oslo, Norway. Sci Total Environ 408:1915–1924

    Article  Google Scholar 

  • Prieto-Rodríguez L, Oller I, Klamerth N, Agüera A, Rodríguez EM, Malato S (2013) Application of solar AOPs and ozonation for elimination of micropollutants in municipal wastewater treatment plant effluents. Water Res 47:1521–1528

    Article  Google Scholar 

  • Qi C, Liu X, Lin C, Zhang X, Ma J, Tan H, Ye W (2014) Degradation of sulfamethoxazole by microwave-activated persulfate: kinetics, mechanism and acute toxicity. Chem Eng J 249:6–14

    Article  CAS  Google Scholar 

  • Raja P, Bozzi A, Mansilla H, Kiwi J (2005) Evidence for superoxide-radical anion, singlet oxygen and OH-radical intervention during the degradation of the lignin model compound (3-methoxy-4-hydroxyphenylmethylcarbinol). J Photochem Photobiol A Chem 169:271–278

    Article  CAS  Google Scholar 

  • Reis PJM, Reis AC, Ricken B, Kolvenbach BA, Manaia CM, Corvini PFX, Nunes OC (2014) Biodegradation of sulfamethoxazole and other sulfonamides by achromobacter denitrificans PR1. J Hazard Mater 280:741–749

    Article  CAS  Google Scholar 

  • Richard J, Boergers A, Vom Eyser C, Bester K, Tuerk J (2014) Toxicity of the micropollutants bisphenol A, ciprofloxacin, metoprolol and sulfamethoxazole in water samples before and after the oxidative treatment. Int J Hyg Environ Health 217:506–514

    Article  CAS  Google Scholar 

  • Safarzadeh-Amiri A, Bolton JR, Cater SR (1997) Ferrioxalate-mediated photodegradation of organic pollutants in contaminated water. Water Res 31:787–798

    Article  CAS  Google Scholar 

  • Seraghni N, Belattar S, Mameri Y, Debbache N, Sehili T (2012) Fe(III)-citrate-complex-induced photooxidation of 3-methylphenol in aqueous solution. Int J Photoenergy 2012:1–10

    Article  Google Scholar 

  • Soares P, Silva TCV, Manenti D, Souza SAGU, Boaventura RR, Vilar VP (2014) Insights into real cotton-textile dyeing wastewater treatment using solar advanced oxidation processes. Environ Sci Pollut Res 21:932–945

    Article  CAS  Google Scholar 

  • Soares PA, Batalha M, Souza SMAGU, Boaventura RAR, Vilar VJP (2015) Enhancement of a solar photo-Fenton reaction with ferric-organic ligands for the treatment of acrylic-textile dyeing wastewater. J Environ Manag 152:120–131

    Article  CAS  Google Scholar 

  • Souza BM, Dezotti MWC, Boaventura RAR, Vilar VJP (2014) Intensification of a solar photo-Fenton reaction at near neutral pH with ferrioxalate complexes: a case study on diclofenac removal from aqueous solutions. Chem Eng J 256:448–457

    Article  CAS  Google Scholar 

  • Sushil KK, Terrence JC (2007): Human pharmaceuticals in the aquatic environment: a challenge to green chemistry. ChemInform 38

  • Trovó AG, Nogueira RFP, Agüera A, Fernandez-Alba AR, Sirtori C, Malato S (2009) Degradation of sulfamethoxazole in water by solar photo-Fenton. Chemical and toxicological evaluation. Water Res 43:3922–3931

    Article  Google Scholar 

  • Wang A, Li Y-Y, Estrada AL (2011) Mineralization of antibiotic sulfamethoxazole by photoelectro-Fenton treatment using activated carbon fiber cathode and under UVA irradiation. Appl Catal B Environ 102:378–386

    Article  CAS  Google Scholar 

  • Zameeruddin S, Sastry BA, Ponticelli G, Massacesi M (1993) EPR studies on copper(II) in four divalent diamagnetic metallic complexes of 3-amino,5-methylisoxazole. Polyhedron 12:1427–1429

    Article  CAS  Google Scholar 

  • Zepp RG, Hoigne J, Bader H (1987) Nitrate-induced photooxidation of trace organic chemicals in water. Environ Sci Technol 21:443–450

    Article  CAS  Google Scholar 

  • Zhang X, Rosenstein BS, Wang Y, Lebwohl M, Wei H (1997) Identification of possible reactive oxygen species involved in ultraviolet radiation-induced oxidative DNA damage. Free Radic Biol Med 23:980–985

    Article  CAS  Google Scholar 

  • Zuo Y, Hoigne J (1992) Formation of hydrogen peroxide and depletion of oxalic acid in atmospheric water by photolysis of iron(III)-oxalato complexes. Environ Sci Technol 26:1014–1022

    Article  CAS  Google Scholar 

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Acknowledgments

This work was co-financed by (i) FCT/MEC (Fundação para a Ciência e a Tecnologia/Ministério da Educação e Ciência) and FEDER (Fundo Europeu de Desenvolvimento Regional) under Program PT2020 (project UID/EQU/50020/2013) and (ii) FEDER, QREN (Quadro de Referência Estratégico Nacional), and ON2 program (Programa Operacional Regional do Norte) (project NORTE-07-0162-FEDER-000050). B.M. Souza acknowledges her Doctoral scholarship supported by Program Brazil/Portugal CAPES/FCT 308/11 (Research grant-BEX Process: 8960-12-7). B.A. Marinho acknowledges her Doctoral fellowship supported by CAPES (BEX-0983-13-6). F.C. Moreira acknowledges her Doctoral fellowship SFRH/BD/80361/2011 supported by FCT. V.J.P. Vilar acknowledges the FCT Investigator 2013 Programme (IF/01501/2013).

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  1. LSRE-Laboratory of Separation and Reaction Engineering-Associate Laboratory LSRE/LCM, Departamento de Engenharia Química, Faculdade de Engenharia, Universidade do Porto, Rua Dr. Roberto Frias, 4200-465, Porto, Portugal

    Bianca M. Souza, Belisa A. Marinho, Francisca C. Moreira, Rui A.R. Boaventura & Vítor J. P. Vilar

  2. Chemical Engineering Program-COPPE, Federal University of Rio de Janeiro, P.O. Box 68502, 21941-972, Rio de Janeiro, RJ, Brazil

    Bianca M. Souza & Márcia W. C. Dezotti

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  1. Bianca M. Souza
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  2. Belisa A. Marinho
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  3. Francisca C. Moreira
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Souza, B.M., Marinho, B.A., Moreira, F.C. et al. Photo-Fenton oxidation of 3-amino-5-methylisoxazole: a by-product from biological breakdown of some pharmaceutical compounds. Environ Sci Pollut Res 24, 6195–6204 (2017). https://doi.org/10.1007/s11356-015-5690-1

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