Development of electrodeposited nanostructural poly (o-aminophenol) coating as a solid phase microextraction fiber for determination of bisphenol A

Volume 4, Issue 02, Pages 34-46, Jun 2021 *** Field: Analytical Nano Chemistry

  • Mohammad Saraji Department of Chemistry, Isfahan University of Technology, Isfahan, Iran
  • Bahman Farajmand, (Corresponding Author) Department of Chemistry, Faculty of Science, University of Zanjan, Zanjan, Iran.
  • Esmaeil Heydari Bafrouei Department of Chemistry, Vali-Asr University of Rafsanjan, Rafsanjan, Iran.
Keywords: Poly (o-aminophenol), Nanostructure, Bisphenol A, Solid phase microextraction, Gas chromatography-flame ionization detector

Abstract

In this research nanostructural poly (o-aminophenol) was synthesized by electropolymerization and used for solid phase microextraction procedure (SPME). Thin film of Poly (o-aminophenol) (4 µm thickness) was shaped by sweep potential for 45 min on the surface of stainless steel wire. Polymer was synthesized by potentiostat procedure too. Prepared polymer by sweep potential procedure showed nanostructures on the surface. Acetic anhydride was employed for derivatization of bisphenol A (BPh-A) and analysis of acetylated BPh-A was utilized by gas chromatography-flame ionization detector (GC-FID). Affecting parameters on derivatization and extraction such as amount of acetic anhydride, stirring rate, temperature, ionic strength and extraction time were optimized. The limit of detection (LOD) and relative standard divisions (RSDs%) were achieved 0.6 µgL-1 and less than 6.8%, respectively under optimized conditions. Finally proposed method was used for extraction of bisphenol A from leaching of baby and drinking water bottles. Relative recovery was achieved 98% for leaching from drinking bottle. In leaching from plastic baby bottle, bisphenol A (BPh-A) was detected in the range 5–15 µg L-1.

 

References

A. Spietelun, Ł. Marcinkowski, M. De, J. Namie, Recent developments and future trends in solid phase microextraction techniques towards green analytical chemistry, J. Chromatogr. A, 1321 (2013) 1–13.

M. Lashgari, Y. Yamini, An overview of the most common lab-made coating materials in solid phase microextraction, Talanta, 191 (2019) 283-306.

A. Mollahosseini, E. Noroozian, Polyphosphate-doped polypyrrole coated on steel fiber for the solid-phase microextraction of organochlorine pesticides in water, Anal. Chim. Acta, 638 (2009) 169–174.

W. Du, F. Zhao, B. Zeng, Novel multiwalled carbon nanotubes – polyaniline composite film coated platinum wire for headspace solid-phase microextraction and gas chromatographic determination of phenolic compounds, J. Chromatogr. A, 1216 (2009) 3751–3757.

H. Bagheri, A. Roostaie, Aniline – silica nanocomposite as a novel solid phase microextraction fiber coating, J. Chromatogr. A, 1238 (2012) 22–29.

R. Tucceri, Poly (o-aminophenol) film electrodes, Springer International Publishing Switzerland, 2013.

R. Tucceri, P. Arnal, A. Scian, Electrosynthesis and spectroscopic characterization of poly (o-aminophenol) film electrodes, ISRN Polym. Sci., 2012 (2012) 1–26.

C. Barbero, J.J. Silber, L. Sereno, Formation of a novel electroactive film by electropolymerization of ortho-aminophenol, Study of its chemical structure and formation mechanism, Electropolymerization of analogous compounds, J. Electroanal. Chem., 263 (1989) 333–352.

X. Chen, J. Chen, C. Deng, C. Xiao, Y. Yang, Z. Nie, et al., Amperometric glucose biosensor based on boron-doped carbon nanotubes modified electrode, Talanta, 76 (2008) 763–767.

D. Pan, J. Chen, S. Yao, W. Tao, L. Nie, An amperometric glucose biosensor based on glucose oxidase immobilized in electropolymerized poly (o-aminophenol) and carbon nanotubes composite film on a gold electrode, Anal. Sci., 21 (2005) 367–371.

M.A.V. Garcia, P.T. Blancoa, A. Ivaska, A poly (o-aminophenol ) modified electrode as an amperometric hydrogen peroxide biosensor, Electrochim. Acta, 43 (1998) 3533–3539.

N. Kumar, R. N. Goyal, Simultaneous determination of melatonin and 5-hydroxytrptophan at the disposable poly-(melamine)/poly-(o-aminophenol) composite modified screen printed sensor J. Electroanal. Chem., 874 (2020) 114458.

M.C. Miras, A. Badano, M.M. Bruno, C. Barbero, Nitric oxide electrochemical sensors based on hybrid films of conducting polymers and metal phtalocyanines, Port. Electrochim. Acta, 21 (2003) 235–243.

L. Liu, H. Cui, H. An, J. Zhai, Y. Pan, Electrochemical detection of aqueous nitrite based on poly(aniline-co-o-aminophenol)-modified glassy carbon electrode, Ionics, 23 (2017) 1517-1523.

A. B. Slimane, A. F. Al‑Hossainy, M. S. Zoromba, Synthesis and optoelectronic properties of conductive nanostructured poly(aniline-co-o-aminophenol) thin film, J. Mater. Sci.: Mater. Electron., 29 (2018) 8431-8445.

S. Mu, Catechol sensor using poly (aniline-co- o-aminophenol) as an electron transfer mediator, Biosens. Bioelectron., 21 (2006) 1237–1243.

L. Zhang, J. Lian, Electrochemical synthesis of copolymer of aniline and o-aminophenol and its use to the electrocatalytic oxidation of ascorbic acid, J. Electroanal. Chem., 611 (2007) 51–59.

W. Zhaoyang, Z. Xiaolei, Y. Yunhui, S. Guoli, Y. Ruqin, A sensitive nicotine sensor based on molecularly imprinted electropolymer of o-aminophenol, Front. Chem. China, 32 (2006) 183–187.

A. Ballesteros-gómez, S. Rubio, D. Pérez-bendito, Analytical methods for the determination of bisphenol A in food, J. Chromatogr. A, 1216 (2009) 449–469.

R.T. Zoeller, R. Bansal, C. Parris, Bisphenol-A , an environmental contaminant that acts as a thyroid hormone receptor antagonist in vitro , increases serum thyroxine , and alters RC3 / neurogranin expression in the developing rat brain, Endocrinology, 146 (2004) 607–612.

Y.B. Wetherill, C.E. Petre, K.R. Monk, A. Puga, K.E. Knudsen, The xenoestrogen bisphenol A induces inappropriate androgen receptor activation and mitogenesis in prostatic adenocarcinoma cells 1, Mol. Cancer Ther., 13 (2002) 515–524.

B.T. Akingbemi, C.M. Sottas, A.I. Koulova, G.R. Klinefelter, M.P. Hardy, Inhibition of testicular steroidogenesis by the xenoestrogen bisphenol A is associated with reduced pituitary luteinizing hormone secretion and decreased steroidogenic enzyme gene expression in rat leydig cells, Endocrinology, 145 (2004) 592–603.

P. Viñas, N. Campillo, Comparison of two derivatization-based methods for solid-phase microextraction – gas chromatography – mass spectrometric determination of bisphenol A , bisphenol S and biphenol migrated from food cans, Anal. Bioanal. Chem., 397 (2010) 115–125.

M.K.R. Mudiam, R. Jain, V.K. Dua, A.K. Singh, V.P. Sharma, Application of ethyl chloroformate derivatization for solid-phase microextraction– gas chromatography-mass spectrometric determination of bisphenol-A in water and milk samples, Anal. Bioanal. Chem., 401 (2011) 1695–1701.

W. Gao, J. Cheng, X. Yuan, Y. Tian, Covalent organic framework-graphene oxide composite: A superior adsorption material for solid phase microextraction of bisphenol A, Talanta, 222 (2021) 121501.

Y. H. Pang, Y. Y. Huang, X. F. Shen, Y. Y. Wang, Electro-enhanced solid-phase microextraction with covalent organic framework modified stainless steel fiber for efficient adsorption of bisphenol A, Anal. Chim. Acta, 1142 (2021) 99-107.

N. Mohammadnezhad, A. A. Matin, N. Samadi, A. Shomali, H. Valizadeh, Ionic liquid-bonded fused silica as a new solid-phase microextraction fiber for the liquid chromatographic determination of bisphenol A as an endocrine disruptor, J. AOAC Int., 100 (2017) 218–223.

Y. Liu, Y. Liu, Z. Liu, F. Du, G. Qin, G. Li, X. Hu, Z. Xu, Z. Cai, Supramolecularly imprinted polymeric solid phase microextraction coatings for synergetic recognition nitrophenols and bisphenol A, J. Hazard. Mater., 368 (2019) 358–364

S. Kunimura, T. Ohsaka, N. Oyama, Preparation of thin polymeric films on electrode surfaces by electropolymerization of o-aminophenol, Macromolecules, 21 (1988) 894–900.

J.M. Ortega, Conducting potential range for poly (o-aminophenol), Thin Solid Films, 371 (2000) 28–35.

D. Gonc, R.C. Faria, M. Yonashiro, L.O.S. Bulhoes, Electrochemical oxidation of o-aminophenol in aqueous acidic medium: formation of film and soluble products, J. Electroanal. Chem., 487 (2000) 90–99.

A.A. Shah, R. Holze, Poly (o-aminophenol) with two redox processes: A spectroelectrochemical study, J. Electroanal. Chem., 597 (2006) 95–102.

A.Q. Zhang, C.Q. Cui, Y.Z. Chen, J.Y. Lee, Synthesis and electrochromic properties of poly-o-aminophenol, J. Electroanal. Chem., 373 (1994) 115–121.

A.Q. Zhang, C.Q. Cui, J.Y. Lee, Metal-polymer interactions in the Ag+ -poly-o-aminophenol system, J. Electroanal. Chem., 413 (1996) 143–151.

A. Guenbour, A. Kacemi, A. Benbachir, L. Aries, Electropolymerization of 2-aminophenol Electrochemical and spectroscopic studies, Prog. Org. Coat., 38 (2000) 121–126.

S.M. Sayyah, M.M. El-Rabiey, S.S.A. El-rehim, R.E. Azooz, Electropolymerization kinetics of o-aminophenol and characterization of the obtained polymer films, J. Appl. Polym. Sci., 99 (2006) 3093–3109.

R. Ojani, J. Raoof, S. Fathi, 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 (2009) 2190–2196.

A. Mohammadi, Y. Yamini, N. Alizadeh, Dodecylsulfate-doped polypyrrole film prepared by electrochemical fiber coating technique for headspace solid-phase microextraction of polycyclic aromatic hydrocarbons, J. Chromatogr. A, 1063 (2005) 1–8.

N. De Coensel, F. David, P. Sandra, Study on the migration of bisphenol-A from baby bottles by stir bar sorptive extraction- thermal desorption-capillary GC-MS, J. Sep. Sci., 32 (2009) 3829–3836.

N. Rastkari, R. Ahmadkhaniha, M. Yunesian, L.J. Baleh, A. Mesdaghinia, Sensitive determination of bisphenol A and bisphenol F in canned food using a solid-phase microextraction fibre coated with single-walled carbon nanotubes before GC/MS, Food Addit. Contam., 27 (2010) 1460–1468.

Published
2021-06-28
How to Cite
Saraji, M., Farajmand, B., & Heydari Bafrouei, E. (2021). Development of electrodeposited nanostructural poly (o-aminophenol) coating as a solid phase microextraction fiber for determination of bisphenol A. Analytical Methods in Environmental Chemistry Journal, 4(02), 34-46. https://doi.org/10.24200/amecj.v4.i02.142
Section
Original Article