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Electro-transformation of mefenamic acid drug: a case study of kinetics, transformation products, and toxicity

  • Zainab Haider Mussa
  • Fouad Fadhil Al-QaimEmail author
  • Ali Yuzir
  • Jalifah Latip
Research Article

Abstract

Poor removal of many pharmaceuticals and personal care products in sewage treatment plants leads to their discharge into the receiving waters, where they may cause negative effects for aquatic environment and organisms. In this study, electrochemical removal process has been used as alternative method for removal of mefenamic acid (MEF). For our knowledge, removal of MEF using electrochemical process has not been reported yet. Effects of initial concentration of mefenamic acid, sodium chloride (NaCl), and applied voltage were evaluated for improvement of the efficiency of electrochemical treatment process and to understand how much electric energy was consumed in this process. Removal percentage (R%) was ranged between 44 and 97%, depending on the operating parameters except for 0.1 g NaCl which was 9.1%. Consumption energy was 0.224 Wh/mg after 50 min at 2 mg/L of mefenamic acid, 0.5 g NaCl, and 5 V. High consumption energy (0.433 Wh/mg) was observed using high applied voltage of 7 V. Investigation and elucidation of the transformation products were provided by Bruker software dataAnalysis using liquid chromatography-time of flight mass spectrometry. Seven chlorinated and two non-chlorinated transformation products were investigated after 20 min of electrochemical treatment. However, all transformation products (TPs) were eliminated after 140 min. For the assessment of the toxicity, it was impacted by the formation of transformation products especially between 20 and 60 min then the inhibition percentage of E. coli bacteria was decreased after 80 min to be the lowest value.

Keywords

Electrochemical treatment Mefenamic acid LC-TOF/MS Solid phase extraction Chlorinated transformation products Toxicity assessment 

Notes

Funding

The Universiti Teknologi Malaysia (UTM) and the Ministry of Higher Education Malaysia (MOHE) funded this research under Grant Nos. 4 J284 and 4F807. Furthermore, this work was also financial supported under grant Professional Development Research University (PDRU) Grant No: 04E52.

Supplementary material

11356_2019_4301_MOESM1_ESM.docx (542 kb)
ESM 1 (DOCX 541 kb)

References

  1. Al-Odaini NA, Zakaria MP, Yaziz MI, Surif S (2010) Multi-residue analytical method for human pharmaceuticals and synthetic hormones in river water and sewage effluents by solid-phase extraction and liquid chromatography–tandem mass spectrometry. J Chromatogr A 1217:6791–6806.  https://doi.org/10.1016/j.chroma.2010.08.033 CrossRefGoogle Scholar
  2. Al-Qaim FF, Abdullah P, Othman MR, Latip J, Afiq WM (2013) Development of analytical method for detection of some pharmaceuticals in surface water. Trop J Pharm Res 12:609–616.  https://doi.org/10.4314/tjpr.v12i4.25 Google Scholar
  3. Al-Qaim FF, Abdullah MP, Othman MR, Latip J, Afiq W (2014) A validation method development for simultaneous LC-ESI-TOF/MS analysis of some pharmaceuticals in Tangkas river-Malaysia. J Brazil Chem Soc 25:271–281.  https://doi.org/10.5935/0103-5053.20130294 Google Scholar
  4. Al-Qaim FF, Mussa ZH, Othman MR, Abdullah MP (2015) Removal of caffeine from aqueous solution by indirect electrochemical oxidation using a graphite-PVC composite electrode: a role of hypochlorite ion as an oxidising agent. J Hazard Mater 300:387–397.  https://doi.org/10.1016/j.jhazmat.2015.07.007 CrossRefGoogle Scholar
  5. Al-Qaim FF, Mussa ZH, Yuzir A, Latip J, Othman MR (2018a) The fate of prazosin and levonorgestrel after electrochemical degradation process: monitoring by-products using LC-TOF/MS. J Environ Sci 74:134–146.  https://doi.org/10.1016/j.jes.2018.02.019 CrossRefGoogle Scholar
  6. Al-Qaim FF, Mussa ZH, Yuzir A (2018b) Development and validation of a comprehensive solid-phase extraction method followed by LC-TOF/MS for the analysis of eighteen pharmaceuticals in influent and effluent of sewage treatment plants. Anal Bioanal Chem 410:4829–4846.  https://doi.org/10.1007/s00216-018-1120-9 CrossRefGoogle Scholar
  7. Baena-Nogueras RM, González-Mazo E, Lara-Martín PA (2017) Degradation kinetics of pharmaceuticals and personal care products in surface waters: photolysis vs biodegradation. Sci Total Environ 590:643–654.  https://doi.org/10.1016/j.scitotenv.2017.03.015 CrossRefGoogle Scholar
  8. Benitez FJ, Acero JL, Real FJ, Roldan G, Rodriguez E (2013) Photolysis of model emerging contaminants in ultra-pure water: kinetics, by-products formation and degradation pathways. Water Res 47:870–880.  https://doi.org/10.1016/j.watres.2012.11.016 CrossRefGoogle Scholar
  9. Brillas E, Garcia-Segura S, Skoumal M, Arias C (2010) Electrochemical incineration of diclofenac in neutral aqueous medium by anodic oxidation using Pt and boron-doped diamond anodes. Chemosphere 79:605–612.  https://doi.org/10.1016/j.chemosphere.2010.03.004 CrossRefGoogle Scholar
  10. Cavalcanti EB, Garcia-Segura S, Centellas F, Brillas E (2013) Electrochemical incineration of omeprazole in neutral aqueous medium using a platinum or boron-doped diamond anode: degradation kinetics and oxidation products. Water Res 47:1803–1815.  https://doi.org/10.1016/j.watres.2013.01.002 CrossRefGoogle Scholar
  11. Chen P, Lv W, Chen Z, Ma J, Li R, Yao K, Liu G, Li F (2015) Photo-transformation of mefenamic acid induced by nitrite ions in water: mechanism, toxicity, and degradation pathways. Environ Sci Pollut R 22:12585–12596.  https://doi.org/10.1007/s11356-015-4537-0 CrossRefGoogle Scholar
  12. Colombo R, Ferreira TC, Ferreira RA, Lanza MR (2016) Removal of mefenamic acid from aqueous solutions by oxidative process: optimization through experimental design and HPLC/UV analysis. J Environ Manag 167:206–213.  https://doi.org/10.1016/j.jenvman.2015.11.029 CrossRefGoogle Scholar
  13. Deborde M, Von Gunten UR (2008) Reactions of chlorine with inorganic and organic compounds during water treatment-kinetics and mechanisms: a critical review. Water Res 42:13–51.  https://doi.org/10.1016/j.watres.2007.07.025 CrossRefGoogle Scholar
  14. Drugbank (2018): https://www.drugbank.ca/drugs/DB00784. Accessed at 01 August 2018
  15. Feng L, Van Hullebusch ED, Rodrigo MA, Esposito G, Oturan MA (2013) Removal of residual anti-inflammatory and analgesic pharmaceuticals from aqueous systems by electrochemical advanced oxidation processes. A review. Chem Eng J 228:944–964.  https://doi.org/10.1016/j.cej.2013.05.061 CrossRefGoogle Scholar
  16. Heli H, Jabbari A, Majdi S, Mahjoub M, Moosavi-Movahedi AA, Sheibani S (2009) Electrooxidation and determination of some non-steroidal anti-inflammatory drugs on nanoparticles of Ni–curcumin-complex-modified electrode. J Solid State Elect 13:1951–1958.  https://doi.org/10.1007/s10008-008-0758-1 CrossRefGoogle Scholar
  17. Indermuhle C, de Vidales MJ, Sáez C, Robles J, Cañizares P, García-Reyes JF, Molina-Díaz A, Comninellis C, Rodrigo MA (2013) Degradation of caffeine by conductive diamond electrochemical oxidation. Chemosphere 93:1720–1725.  https://doi.org/10.1016/j.chemosphere.2013.05.047 CrossRefGoogle Scholar
  18. Kim I, Tanaka H (2009) Photodegradation characteristics of PPCPs in water with UV treatment. Environ Int 35:793–802.  https://doi.org/10.1016/j.envint.2009.01.003 CrossRefGoogle Scholar
  19. Kimura A, Osawa M, Taguchi M (2012) Decomposition of persistent pharmaceuticals in wastewater by ionizing radiation. Radiat Phys Chem 81:1508–1512.  https://doi.org/10.1016/j.radphyschem.2011.11.032 CrossRefGoogle Scholar
  20. Ma L, Li J, Xu L (2017) Aqueous chlorination of fenamic acids: kinetic study, transformation products identification and toxicity prediction. Chemosphere 175:114–122.  https://doi.org/10.1016/j.chemosphere.2017.02.045 CrossRefGoogle Scholar
  21. Martinez-Huitle CA, Ferro S (2006) Electrochemical oxidation of organic pollutants for the wastewater treatment: direct and indirect processes. Chem Soc Rev 35:1324–1340.  https://doi.org/10.1039/B517632H CrossRefGoogle Scholar
  22. Mirzazadeh H, Lashanizadegan M (2018) ZnO/CdO/reduced graphene oxide and its high catalytic performance towards degradation of the organic pollutants. J Serb Chem Soc 83:221–236.  https://doi.org/10.2298/JSC170630097M CrossRefGoogle Scholar
  23. MOH: Malaysian Statistics on Medicine, Ministry of Health Malaysia, Kuala Lumpur. 2014. http://apps.who.int/medicinedocs/documents/s17580en/s17580en.pdf. Accessed 07 July 2018
  24. Moreira FC, Boaventura RA, Brillas E, Vilar VJ (2017) Electrochemical advanced oxidation processes: a review on their application to synthetic and real wastewaters. Appl Catal B-Environ 202:217–261.  https://doi.org/10.1016/j.apcatb.2016.08.037 CrossRefGoogle Scholar
  25. Mussa ZH, Othman MR, Abdullah MP (2015) Electrochemical oxidation of landfill leachate: investigation of operational parameters and kinetics using graphite-PVC composite electrode as anode. J Brazil Chem Soc 26:939–948.  https://doi.org/10.5935/0103-5053.20150055 Google Scholar
  26. Mussa ZH, Al-Qaim FF, Othman MR, Abdullah MP (2016) Removal of simvastatin from aqueous solution by electrochemical process using graphite-PVC as anode: a case study of evaluation the toxicity, kinetics and chlorinated by-products. J Environ Chem Eng 4:3338–3347.  https://doi.org/10.1016/j.jece.2016.07.006 CrossRefGoogle Scholar
  27. Mussa ZH, Al-Qaim FF, Othman MR, Abdullah MP, Latip J, Zakria Z (2017) Pseudo first order kinetics and proposed transformation products pathway for the degradation of diclofenac using graphite–PVC composite as anode. J Taiwan Inst Chem Eng 72:37–44.  https://doi.org/10.1016/j.jtice.2016.12.031 CrossRefGoogle Scholar
  28. Nikolaou A, Meric S, Fatta D (2007) Occurrence patterns of pharmaceuticals in water and wastewater environments. Anal Bioanal Chem 387:1225–1234.  https://doi.org/10.1007/s00216-006-1035-8 CrossRefGoogle Scholar
  29. Parsa JB, Rezaei M, Soleymani AR (2009) Electrochemical oxidation of an azo dye in aqueous media investigation of operational parameters and kinetics. J Hazard Mater 168:997–1003.  https://doi.org/10.1016/j.jhazmat.2009.02.134 CrossRefGoogle Scholar
  30. Sirés I, Brillas E (2012) Remediation of water pollution caused by pharmaceutical residues based on electrochemical separation and degradation technologies: a review. Environ Int 40:212–229.  https://doi.org/10.1016/j.envint.2011.07.012 CrossRefGoogle Scholar
  31. Sirés I, Oturan N, Oturan MA (2010) Electrochemical degradation of β-blockers. Studies on single and multicomponent synthetic aqueous solutions. Water Res 44:3109–3120.  https://doi.org/10.1016/j.watres.2010.03.005 CrossRefGoogle Scholar
  32. Soufan M, Deborde M, Legube B (2012) Aqueous chlorination of diclofenac: kinetic study and transformation products identification. Water Res 46:3377–3386.  https://doi.org/10.1016/j.watres.2012.03.056 CrossRefGoogle Scholar
  33. Zaccone P, Fehervari Z, Phillips JM, Dunne DW, Cooke A (2006) Parasitic worms and inflammatory diseases. Parasite Immunol 28:515–523.  https://doi.org/10.1111/j.1365-3024.2006.00879.x CrossRefGoogle Scholar
  34. Zhang Y, Geißen S-U, Gal C (2008) Carbamazepine and diclofenac: removal in wastewater treatment plants and occurrence in water bodies. Chemosphere 73:1151–1161.  https://doi.org/10.1016/j.chemosphere.2008.07.086 CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  • Zainab Haider Mussa
    • 1
  • Fouad Fadhil Al-Qaim
    • 1
    • 2
    Email author
  • Ali Yuzir
    • 1
  • Jalifah Latip
    • 3
  1. 1.Malaysia-Japan International Institute of Technology (MJIIT)Universiti Teknologi MalaysiaKuala LumpurMalaysia
  2. 2.Department of Chemistry, Faculty of Science for WomenUniversity of BabylonHillaIraq
  3. 3.School of Chemical Sciences and Food Technology, Faculty of Science and TechnologyUniversiti Kebangsaan Malaysia (UKM)BangiMalaysia

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