Skip to main content
SpringerLink
Log in

Electrochemical determination of cyanuric acid using the signal suppression of melamine on an overoxidized Poly-(para-aminophenol) coated glassy carbon electrode

  • Research Article
  • Published:
Journal of Applied Electrochemistry Aims and scope Submit manuscript

Abstract

Cyanuric acid (CA) is known as an important environmental and human toxin with low electroactivity. Therefore, it is an attractive issue to develop an electrochemical sensor for CA determination. Here, we reported a novel electrochemical sensor for the indirect electrochemical determination of CA using the complex formation between CA and melamine (MEL), for the first time. Firstly, the electrochemical conversation of MEL to electroactive polymelamine was conducted using a glassy carbon electrode modified with overoxidized Poly-(para-aminophenol) film. MEL was chosen as a probe for indirect determination, and its current intensity was recorded. CA was then added to the medium, and the decline in the current intensity was considered as the sensor response. The calibration curve within the range of 100–2500 µmol L−1 was constructed from sensor response against CA concentration using square wave voltammetry. The limit of detection was found to be 80.28 µmol L−1. Moreover, the proposed mechanism for the indirect determination of CA was investigated based on the quantum theory of atoms in molecules analysis. Finally, the developed method was able to exhibit an excellent recovery range (91.2–101.0%) for the real sample analysis.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Dorne JL, Doerge DR, Vandenbroeck M, Fink-Gremmels J, Mennes W, Knutsen HK, Vernazza F, Castle L, Edler L, Benford D (2013) Recent advances in the risk assessment of melamine and cyanuric acid in animal feed. Toxicol Appl Pharmacol 270:218–229

    CAS  PubMed  Google Scholar 

  2. Gong H, Tang S, Zhang T (2016) Catalytic hydrolysis of waste residue from the melamine process and the kinetics of melamine hydrolysis in NaOH solution. React Kinet Mech Catal 118:377–391

    CAS  Google Scholar 

  3. Hu X, Shi J, Shi Y, Zou X, Arslan M, Zhang W, Huang X, Li Z, Xu Y (2019) Use of a smartphone for visual detection of melamine in milk based on Au@ Carbon quantum dots nanocomposites. Food Chem 272:58–65

    CAS  PubMed  Google Scholar 

  4. Zhu H, Kannan K (2019) Melamine and cyanuric acid in foodstuffs from the United States and their implications for human exposure. Environ Int 130:104950

    CAS  PubMed  Google Scholar 

  5. Hong M, Sai F, Yong-Ning W, Zhang L, Ping-Ping Z, Hui-Jing C, Yun-Feng Z, Jing-Guang L (2009) Simultaneous determination of melamine, ammelide, ammeline, and cyanuric acid in milk and milk products by gas chromatography-tandem mass spectrometry. Biomed Environ Sci 22:87–94

    Google Scholar 

  6. Zhu H, Halden RU, Kannan K (2019) A nationwide survey of the occurrence of melamine and its derivatives in archived sewage sludge from the United States. Environ Pollut 245:994–999

    CAS  PubMed  Google Scholar 

  7. Zhu H, Wang Y, Sun H, Kannan K (2019) Fertilizers as a source of melamine and cyanuric acid in soils: a nationwide survey in China. Environ Sci Technol Lett 6:55–61

    CAS  Google Scholar 

  8. Liu X, Silverman AD, Alam KK, Iverson E, Lucks JB, Jewett MC, Raman S (2019) Design of a transcriptional biosensor for the portable, on-demand detection of cyanuric acid. ACS Synth Biol 9:84–94

    PubMed  PubMed Central  Google Scholar 

  9. Karns JS (1999) Gene sequence and properties of an s-triazine ring-cleavage enzyme from Pseudomonas sp. strain NRRLB-12227. Appl Environ Microbiol 65:3512–3517

    CAS  PubMed  PubMed Central  Google Scholar 

  10. Brown CA, Jeong KS, Poppenga RH, Puschner B, Miller DM, Ellis AE, Kang KI, Sum S, Cistola AM, Brown SA (2007) Outbreaks of renal failure associated with melamine and cyanuric acid in dogs and cats in 2004 and 2007. J Vet Diagn 19:525–531

    Google Scholar 

  11. Liu CC, Hsieh TJ, Wu CF, Tsai YC, Huang SP, Lee YC, Huang TY, Shen JT, Chou YH, Huang CN (2017) Urinary melamine excretion and increased markers of renal tubular injury in patients with calcium urolithiasis: a cross-sectional study. Environ Pollut 231:1284–1290

    CAS  PubMed  Google Scholar 

  12. WH Organization (2009) Toxicological and health aspects of melamine and cyanuric acid: report of a WHO expert meeting in collaboration with FAO. Health Canada, Ottawa, pp 1–4

    Google Scholar 

  13. de Oliveira TV, de Carvalho PP, Petronilho S, Santelli RE, Braz BF, Freire AS, Saunders C, da Rocha HF, Sanz-Medel A, Fernández-Sánchez ML (2020) Total metal content and chemical speciation analysis of iron, copper, zinc and iodine in human breast milk using high-performance liquid chromatography separation and inductively coupled plasma mass spectrometry detection. Food Chem 326:126978

    Google Scholar 

  14. Zhu H, Kannan K (2019) Occurrence of melamine and its derivatives in breast milk from the United States and its implications for exposure in infants. Environ Sci Technol 53:7859–7865

    CAS  PubMed  Google Scholar 

  15. Chao YY, Lee CT, Wei YT, Kou HS, Huang YL (2011) Using an on-line microdialysis/HPLC system for the simultaneous determination of melamine and cyanuric acid in non-dairy creamer. Anal Chim Acta 702:56–61

    CAS  PubMed  Google Scholar 

  16. Braekevelt E, Lau BY, Feng S, Ménard C, Tittlemier S (2011) Determination of melamine, ammeline, ammelide and cyanuric acid in infant formula purchased in Canada by liquid chromatography-tandem mass spectrometry. Food Addit Contam 28:698–704

    CAS  Google Scholar 

  17. Tzing SH, Ding WH (2010) Determination of melamine and cyanuric acid in powdered milk using injection-port derivatization and gas chromatography–tandem mass spectrometry with furan chemical ionization. J Chromatogr A 1217:6267–6273

    CAS  PubMed  Google Scholar 

  18. Mehrabi A, Rahimnejad M, Mohammadi M, Pourali M (2021) Electrochemical detection of Flutamide as an anticancer drug with gold nanoparticles modified glassy carbon electrode in the presence of prostate cancer cells. J Appl Electrochem 51(4):597–606

    CAS  Google Scholar 

  19. Yilmaz ÜT, Yazar Z (2010) Determination of cyanuric acid in swimming pool water and milk by differential pulse polarography. Clean: Soil, Air, Water 38:816–821

    CAS  Google Scholar 

  20. Pei L, Xie Y, Pei Y, Cai Z, Fan C (2013) Determination of cyanuric acid by electrochemical cyclic voltammetry method using CuGeO3 nanowires as modified electrode materials. IJNME. https://doi.org/10.1115/1.4026024

    Article  Google Scholar 

  21. Pei L, Liu H, Lin N, Xie Y, Cai Z (2015) Electrochemical analysis of cyanuric acid using polyaniline/CuGeO3 nanowires as electrode modified materials. Curr Pharm Anal 11:16–24

    CAS  Google Scholar 

  22. Han H, Pan D, Pan F, Hu X, Zhu R (2021) A functional micro-needle sensor for voltammetric determination of iron in coastal waters. Sens Actu B Chem 327:128883

    CAS  Google Scholar 

  23. Piech R (2011) Study on simultaneous measurements of trace gallium (III) and germanium (IV) by adsorptive stripping voltammetry using mercury film electrode. J Appl Electrochem 41(2):207–214

    CAS  Google Scholar 

  24. Bard AJ, Faulkner LR, White HS (2022) Electrochemical methods: fundamentals and applications. Wiley

    Google Scholar 

  25. Sağlam Ş, Üzer A, Erçağ E, Apak R (2021) Electrochemical determination of boron using the signal suppression of mannitol on a gold nanoparticle coated p-Aminothiophenol polymer electrode. Microchem J 166:106252

    Google Scholar 

  26. Zerkowski JA, MacDonald JC, Seto CT, Wierda DA, Whitesides GM (1994) Design of organic structures in the solid state: molecular tapes based on the network of hydrogen bonds present in the cyanuric acid. cntdot. melamine complex. J Am Chem Soc 116:2382–2391

    CAS  Google Scholar 

  27. Ji H-F, Xu X (2010) Hexagonal organic nanopillar array from the melamine—cyanuric acid complex. Langmuir 26:4620–4622

    CAS  PubMed  PubMed Central  Google Scholar 

  28. Wang C, Qin X, Huang B, He F, Zeng C (2010) Hemolysis of human erythrocytes induced by melamine–cyanurate complex. Biochem Biophys Res Commun 402:773–777

    CAS  PubMed  Google Scholar 

  29. Mehra N, Jeske M, Yang X, Gu J, Kashfipour MA, Li Y, Baughman JA, Zhu J (2019) Hydrogen-bond driven self-assembly of two-dimensional supramolecular melamine-cyanuric acid crystals and its self-alignment in polymer composites for enhanced thermal conduction. ACS Appl Polym Mater 1:1291–1300

    CAS  Google Scholar 

  30. Esmaeily Z, Madrakian T, Afkhami A, Ghoorchian A, Ghasemzadeh-Mohammadi V (2021) Electropolymerization as an electrochemical preconcentration approach for the determination of melamine in milk samples. Electrochim Acta 390:138897

    CAS  Google Scholar 

  31. Cantú R, Evans O, Kawahara FK, Shoemaker JA, Dufour AP (2000) An HPLC method with UV detection, pH control, and reductive ascorbic acid for cyanuric acid analysis in water. Anal Chem 72(23):5820–5828

    PubMed  Google Scholar 

  32. Frisch M, Trucks G, Schlegel H, Scuseria G, Robb M, Cheeseman J, Scalmani G, Barone V, Petersson G, Nakatsuji H (2016) Gaussian 16 revision a. 03. 2016. Gaussian inc, Wallingford

    Google Scholar 

  33. Bader R, Biegler-König F, Schönbohm J (2002) AIM2000 program package, Ver. 2.0. McMaster University, Hamilton

    Google Scholar 

  34. Bader R (2000) AIM2000 program, v. 2.0. McMaster University, Hamilton

    Google Scholar 

  35. Koçak ÇC, Dursun Z (2013) Simultaneous determination of ascorbic acid, epinephrine and uric acid at over-oxidized poly (p-aminophenol) film modified electrode. J Electroanal Chem 694:94–103

    Google Scholar 

  36. Ojani R, Raoof J-B, Fathi S (2009) Poly (o-aminophenol) film prepared in the presence of sodium dodecyl sulfate: application for nickel ion dispersion and the electrocatalytic oxidation of methanol and ethylene glycol. Electrochim Acta 54:2190–2196

    CAS  Google Scholar 

  37. Chen C, Sun C, Gao Y (2008) Electrosynthesis of poly (aniline-co-p-aminophenol) having electrochemical properties in a wide pH range. Electrochim Acta 53:3021–3028

    CAS  Google Scholar 

  38. Chen S, Huang W, Zheng J, Li Z (2011) Study on the electrodissolution and roughening of a palladium electrode in chloride containing solutions. J Electroanal Chem 660(1):80–84

    CAS  Google Scholar 

  39. Panizza M, Cerisola G (2003) Electrochemical oxidation of 2-naphthol with in situ electrogenerated active chlorine. Electrochim Acta 48(11):1515–1519

    CAS  Google Scholar 

  40. Szpyrkowicz L, Radaelli M, Daniele S (2005) Electrocatalysis of chlorine evolution on different materials and its influence on the performance of an electrochemical reactor for indirect oxidation of pollutants. Catal Today 100(3–4):425–429

    CAS  Google Scholar 

  41. Chen S, Liu S, Wen A, Zhang J, Nie H, Chen J, Zeng R, Long Y, Jin Y, Mai R (2018) New insight into electropolymerization of melamine. I: chloride promoted growth of polymelamine in different pH medium. Electrochim Acta 271:312–318

    CAS  Google Scholar 

  42. Kesavan S, Revin SB, John SA (2014) Potentiodynamic formation of gold nanoparticles film on glassy carbon electrode using aminophenyl diazonium cations grafted gold nanoparticles: determination of histamine H2 receptor antagonist. Electrochim Acta 119:214–224

    CAS  Google Scholar 

  43. Praus P, Smýkalová A, Foniok K, Novák V, Hrbáč J (2021) Doping of graphitic carbon nitride with oxygen by means of cyanuric acid: properties and photocatalytic applications. J Environ Chem Eng 9:105498

    CAS  Google Scholar 

  44. Conn MM, Rebek J (1997) Self-assembling capsules. Chem Rev 97:1647–1668

    CAS  PubMed  Google Scholar 

  45. Ma M, Bong D (2011) Determinants of cyanuric acid and melamine assembly in water. Langmuir 27:8841–8853

    CAS  PubMed  Google Scholar 

  46. Ohtaki H (2003) Effects of temperature and pressure on hydrogen bonds in water and in formamide. J Mol Liq 103:3–13

    Google Scholar 

  47. Mizan TI, Savage PE, Ziff RM (1996) Temperature dependence of hydrogen bonding in supercritical water. J Phys Chem A 100:403–408

    CAS  Google Scholar 

  48. Li R, Cui X, Bi J, Ji X, Li X, Wang N, Huang Y, Huang X, Hao H (2021) Urea-induced supramolecular self-assembly strategy to synthesize wrinkled porous carbon nitride nanosheets for highly-efficient visible-light photocatalytic degradation. RSC Adv 11:23459–23470

    CAS  PubMed  PubMed Central  Google Scholar 

  49. Ghoorchian A, Afkhami A, Madrakian T, Rameshan R, Rameshan C, Hajian A (2020) Absorbance-based spectroelectrochemical sensor for determination of ampyra based on electrochemical preconcentration. Sens Actu B Chem 324:128723

    CAS  Google Scholar 

  50. Ngamchuea K, Moonla C, Watwiangkham A, Wannapaiboon S, Suthirakun S (2022) Electrochemical and structural investigation of copper phthalocyanine: application in the analysis of kidney disease biomarker. Electrochim Acta 428:140951

    CAS  Google Scholar 

  51. Ding L, Yan J, Zhao Z, Li D (2019) Synthesis of NiGa2O4 nanosheets for non-enzymatic glucose electrochemical sensor. Sens Actu B Chem 296:126705. https://doi.org/10.1016/j.snb.2019.126705

    Article  CAS  Google Scholar 

  52. Lin S, Liu S, Dai G, Zhang X, Xia F, Dai Y (2021) A click-induced fluorescence-quenching sensor based on gold nanoparticles for detection of copper(II) ion and ascorbic acid. Dyes Pigments 195:109726. https://doi.org/10.1016/j.dyepig.2021.109726

    Article  CAS  Google Scholar 

  53. Lin Y, Kannan P, Zeng Y, Qiu B, Guo L, Lin Z (2019) Enzyme-free multicolor biosensor based on Cu2+-modified carbon nitride nanosheets and gold nanobipyramids for sensitive detection of neuron specific enolase. Sens Actu B Chem 283:138–145. https://doi.org/10.1016/j.snb.2018.12.007

    Article  CAS  Google Scholar 

  54. Zalazar MF, Paredes EN, Romero Ojeda GD, Cabral ND, Peruchena NM (2018) Study of confinement and catalysis effects of the reaction of methylation of benzene by methanol in H-Beta and H-ZSM-5 zeolites by topological analysis of electron density. J Phys Chem C 122:3350–3362

    CAS  Google Scholar 

  55. Nasiri M, Shakourian-Fard M, Fattahi A (2012) Influence of the hydrogen bonding on the basicity of selected macrocyclic amines. J Phys Org Chem 25:803–810

    CAS  Google Scholar 

Download references

Acknowledgements

This work has been supported by grants from the Bu-Ali Sina University Research Council. This research is also jointly supported by the Hamadan University of Medical Sciences, and the Centre of Excellence in Development of Environmentally Friendly Methods for Chemical Synthesis (CEDEFMCS) which are gratefully acknowledged.

Author information

Authors and Affiliations

  1. Faculty of Chemistry, Bu-Ali Sina University, Hamedan, Iran

    Samaneh Hashemi, Abbas Afkhami, Mahdie Kamalabadi, Tayyebeh Madrakian & Arash Ghoorchian

  2. D-8 International University, Hamedan, Iran

    Abbas Afkhami

  3. Department of Nutrition and Food Safety, School of Medicine, Hamadan University of Medical Sciences, Hamedan, Iran

    Vahid Ghasemzadeh-Mohammadi

Authors
  1. Samaneh Hashemi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Abbas Afkhami
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mahdie Kamalabadi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Tayyebeh Madrakian
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Arash Ghoorchian
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Vahid Ghasemzadeh-Mohammadi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Abbas Afkhami.

Ethics declarations

Conflict of interest

The authors have no financial or proprietary interests in any material discussed in this article.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hashemi, S., Afkhami, A., Kamalabadi, M. et al. Electrochemical determination of cyanuric acid using the signal suppression of melamine on an overoxidized Poly-(para-aminophenol) coated glassy carbon electrode. J Appl Electrochem 53, 2483–2493 (2023). https://doi.org/10.1007/s10800-023-01931-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10800-023-01931-x

Keywords

Search

Navigation