Advertisement

Polymer Bulletin

, Volume 76, Issue 1, pp 215–226 | Cite as

Electrooxidation of phenol in alcohols and establishment of the permeability of the electrodeposited films

  • László KissEmail author
  • Dóra Bősz
  • Ferenc Kovács
  • Heng Li
  • Sándor Kunsági-Máté
Original Paper
  • 96 Downloads

Abstract

In this work, electrooxidation of phenol was studied in different alcohols (methanol, ethanol, 1-propanol, 1-butanol, 1-pentanol, 2-methyl-1-propanol and benzyl alcohol) at platinum electrode. The electrode fouled in all alcohols during the subsequent cyclic voltammetric scans and poly(phenylene oxide) formed on the electrode surface which was then characterized by Raman spectroscopic studies. The spectra of films deposited from the different alcohols were very similar indicating the uniform composition of the electrodeposited polymer films. Electrolysis of alcoholic phenol solutions at the corresponding constant potential and the subsequent fluorescence studies showed that no soluble polymer formed during the anodic oxidation and each polymer adsorbed on the electrode surface. Permeability studies of the electrodeposited polyphenols using 1,4-dihydroxybenzene as a redox probe showed high diffusion hindrance in case of all alcohols except for benzyl alcohol where phenol electrodeposited mainly in separated islands. Heat treatment at 150 °C enhanced the decrease in permeability.

Keywords

Phenol Alcohol Cyclic voltammetry Fouling Permeability 

Notes

Acknowledgements

Financial support of the GINOP 2.3.2-15-2016-00022 and EFOP-3.6.1.-16-2016-00004 Grants is highly appreciated. The work was also supported by Fundamental Research Funds for the Central Universities (20720170084) of China. The present scientific contribution is dedicated to the 650th anniversary of the foundation of the University of Pécs, Hungary.

References

  1. 1.
    Mengoli G, Musiani MM (1994) Phenol electropolymerization: a straight route from monomers to polymer coatings. Prog Org Coat 24:237–251.  https://doi.org/10.1016/0033-0655(94)85017-8 CrossRefGoogle Scholar
  2. 2.
    Lapuente R, Cases F, Garcés P, Morallón E, Vázquez JL (1998) A voltammetric and FTIR–ATR study of the electropolymerization of phenol on platinum electrodes in carbonate medium. Influence of sulfide. J Electroanal Chem 451:163–171.  https://doi.org/10.1016/S0022-0728(98)00098-9 CrossRefGoogle Scholar
  3. 3.
    Prabakaran M, Kim S, Hemapriya V, Chung I (2016) Evaluation of polyphenol composition and anti-corrosion properties of Cryptostegia grandiflora plant extract on mild steel in acidic medium. J Ind Eng Chem 37:47–56.  https://doi.org/10.1016/j.jiec.2016.03.006 CrossRefGoogle Scholar
  4. 4.
    Ureta-Zanartu MS, Bustos P, Berríos C, Diez MC, Mora ML, Gutiérrez C (2002) Electrooxidation of 2,4-dichlorophenol and other polychlorinated phenols at a glassy carbon electrode. Electrochim Acta 47:2399–2406.  https://doi.org/10.1016/S0013-4686(02)00043-9 CrossRefGoogle Scholar
  5. 5.
    Sistiaga M, Pierna AR, Marzo FF, Altube A, Lorenzo A (1998) Electrooxidation of phenol on amorphous Ni–40Nb–1yx/Pt–xSn alloys. Appl Surf Sci 133:124–128.  https://doi.org/10.1016/S0169-4332(98)00180-9 CrossRefGoogle Scholar
  6. 6.
    Ahmed S, Ahmad M, Butt SB (2012) Electrooxidation of chloro, nitro, and amino substituted phenols in aqueous medium and their heterogeneous kinetics. Res Chem Intermed 38:705–722.  https://doi.org/10.1007/s11164-011-0410-z CrossRefGoogle Scholar
  7. 7.
    Fino D, Jara CC, Saracco G, Specchia V, Spinelli P (2005) Deactivation and regeneration of Pt anodes for the electro-oxidation of phenol. J Appl Electrochem 35:405–411.  https://doi.org/10.1007/s10800-005-0799-4 CrossRefGoogle Scholar
  8. 8.
    Skowronski JM, Krawczyk P (2004) Electrooxidation of phenol at exfoliated graphite electrode in alkaline solution. J Solid State Electrochem 8:442–447.  https://doi.org/10.1007/s10008-003-0483-8 CrossRefGoogle Scholar
  9. 9.
    Dulal SMSI, Won M, Shim Y (2010) Carbon fiber supported platinum nanoparticles for electrooxidation of methanol and phenol. J Alloy Compd 494:463–467.  https://doi.org/10.1016/j.jallcom.2010.01.083 CrossRefGoogle Scholar
  10. 10.
    Tahar NB, Savall A (2009) Electropolymerization of phenol on a vitreous carbon electrode in alkaline aqueous solution at different temperatures. Electrochim Acta 55:465–469.  https://doi.org/10.1016/j.electacta.2009.08.040 CrossRefGoogle Scholar
  11. 11.
    Richards JA, Whitson PE, Evans DH (1975) Electrochemical oxidation of 2,4,6-tri-tert-butylphenol. J Electroanal Chem 63:311–327.  https://doi.org/10.1016/S0022-0728(75)80303-2 CrossRefGoogle Scholar
  12. 12.
    Andreescu S, Andreescu D, Sadik OA (2003) A new electrocatalytic mechanism for the oxidation of phenols at platinum electrodes. Electrochem Commun 5:681–688.  https://doi.org/10.1016/S1388-2481(03)00166-8 CrossRefGoogle Scholar
  13. 13.
    Marková E, Kucerová P, Skopalová J, Barták P (2015) Electrochemical oxidation of 2,4,6-tribromophenol in aqueous-alcoholic media. Electroanalysis 27:156–165.  https://doi.org/10.1002/elan.201400412 CrossRefGoogle Scholar
  14. 14.
    Lopes PRM, Montagnolli RN, Bidoia ED (2011) Analytical methods in photoelectrochemical treatment of phenol. J Braz Chem Soc 22:1758–1764.  https://doi.org/10.1590/S0103-50532011000900019 CrossRefGoogle Scholar
  15. 15.
    Rhodes CP, Long JW, Doescher MS, Fontanella JJ, Rolison DR (2004) Nanoscale polymer electrolytes: ultrathin electrodeposited poly(phenylene oxide) with solid-state ionic conductivity. J Phys Chem 108:13079–13087.  https://doi.org/10.1021/jp047671u CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  • László Kiss
    • 1
    • 2
    • 3
    Email author
  • Dóra Bősz
    • 1
  • Ferenc Kovács
    • 1
  • Heng Li
    • 4
    • 5
  • Sándor Kunsági-Máté
    • 1
    • 2
    • 3
  1. 1.Department of General and Physical ChemistryUniversity of PécsPecsHungary
  2. 2.Department of Pharmaceutical ChemistryUniversity of PécsPecsHungary
  3. 3.János Szentágothai Research CenterPecsHungary
  4. 4.Department of Physics, Fujian Provincial Key Laboratory of Semiconductors and Applications, Collaborative Innovation Center for Optoelectronic Semiconductors and Efficient DevicesXiamen UniversityXiamenPeople’s Republic of China
  5. 5.Jiujiang Research Institute of Xiamen UniversityJiujiangPeople’s Republic of China

Personalised recommendations