Skip to main content
SpringerLink
Log in

Introducing selective electro-oxidation of aryl and alkyl sulfides protocol in a novel environmentally friendly media

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

Since derived products from the oxidation of sulfides are vital for pharmaceutical companies, in this paper, electro-oxidation of aryl and alkyl sulfides was investigated on the glassy carbon electrode (GC) by electrochemical techniques such as cyclic voltammetry (CV), chronoamperometry (CA), and electrochemical impedance spectroscopy (EIS). To choose the best electrolyte, electro-oxidation of organic sulfides was investigated in different solutions such as ethanol, propanol, acetone, acetonitrile, and acetic acid. Among them, acetic acid not only did not have the pesky peak but also produced the largest oxidation current with increasing sulfide. In the following, studies were carried out to optimize the percentage of acetic acid and sodium hydroxide solution as a supporting electrolyte and oxygen source, which eventually a mixture of 85:15 acetic acid and solution of 1 M NaOH had the best oxidation efficiency. It should be noted, this effective media is introduced and reported for the first time. Then, the electro-oxidation of several sulfides were investigated in the optimized electrolyte. Kinetic studies were performed on the introduced system and several kinetic data were determined for methyl phenyl sulfide electrochemical oxidation. Finally, a mechanism for the electro-oxidation of sulfide was proposed.

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
Fig.7
Fig. 8
Fig. 9
Fig.10
Fig. 11
Fig. 12
Fig.13
Fig. 14
Fig.15
Fig.16

Similar content being viewed by others

References

  1. I. Fernandez, N. Khiar, Recent developments in the synthesis and utilization of chiral sulfoxides. Chem. Rev. 103, 3651–3706 (2003)

    Article  CAS  Google Scholar 

  2. W.R.F. Goundry, B. Adams, H. Benson, J. Demeritt, S. McKown, K. Mulholland, A. Robertson, P. Siedlecki, P. Tomlin, K. Vare, Development and scale-up of a biocatalytic process to form a chiral sulfoxide. Org. Process Res. Dev. 21, 107–113 (2017)

    Article  CAS  Google Scholar 

  3. E. Hristova, M. Mitov, R. Rashkov, M. Arnaudova, A. Popov, Sulphide oxidation on electrodeposited Ni-Mo-W catalysts. Bulg. Chem. Commun. 40, 291–294 (2008)

    CAS  Google Scholar 

  4. B. Miller, A. Chen, Effect of concentration and temperature on electrochemical oscillations during sulfide oxidation on Ti/Ta2O5–IrO2 electrodes. Electrochim. Acta. 50, 2203–2212 (2005)

    Article  CAS  Google Scholar 

  5. E. Rafiee, S. Shahebrahimi, Organic-inorganic hybrid polyionic liquid based polyoxometalate as nano porous material for selective oxidation of sulfides. J. Mol. Struct. 1139, 255–263 (2017). https://doi.org/10.1016/j.molstruc.2017.03.041

    Article  CAS  Google Scholar 

  6. G. Abdi, A. Alizadeh, M.M. Khodaei, Highly carboxyl-decorated graphene oxide sheets as metal-free catalytic system for chemoselective oxidation of sulfides to sulfones. Mater. Chem. Phys. 201, 323–330 (2017). https://doi.org/10.1016/j.matchemphys.2017.08.062

    Article  CAS  Google Scholar 

  7. S. Rayati, E. Khodaei, M. Jafarian, A. Wojtczak, Mn-Schiff base complex supported on magnetic nanoparticles: synthesis, crystal structure, electrochemical properties and catalytic activities for oxidation of olefins and sulfides. Polyhedron 133, 327–335 (2017). https://doi.org/10.1016/j.poly.2017.05.049

    Article  CAS  Google Scholar 

  8. S. Rayati, F. Nejabat, S. Zakavi, Chemoselective oxidation of sulfides to sulfoxides with urea hydrogen peroxide (UHP) catalyzed by non-, partially and fully ??-brominated meso-tetraphenylporphyrinatomanganese(III) acetate. Inorg. Chem. Commun. 40, 82–86 (2014). https://doi.org/10.1016/j.inoche.2013.11.036

    Article  CAS  Google Scholar 

  9. L.L. Paim, N.R. Stradiotto, Electrooxidation of sulfide by cobalt pentacyanonitrosylferrate film on glassy carbon electrode by cyclic voltammetry. Electrochim. Acta. 55, 4144–4147 (2010). https://doi.org/10.1016/j.electacta.2010.02.082

    Article  CAS  Google Scholar 

  10. S. Rayati, E. Khodaei, S. Shokoohi, M. Jafarian, B. Elmi, A. Wojtczak, Cu-Schiff base complex grafted onto graphene oxide nanocomposite: synthesis, crystal structure, electrochemical properties and catalytic activity in oxidation of olefins. Inorganica Chim. Acta. 466, 520–528 (2017)

    Article  CAS  Google Scholar 

  11. B. Miller, A. Chen, Effect of concentration and temperature on electrochemical oscillations during sulfide oxidation on Ti/Ta 2 O 5–IrO 2 electrodes. Electrochim. Acta. 50, 2203–2212 (2005)

    Article  CAS  Google Scholar 

  12. M. Muñoz, M.A. Gallo, A. Gutiérrez-Alejandre, D. Gazzoli, C.I. Cabello, Molybdenum-containing systems based on natural kaolinite as catalysts for selective oxidation of aromatic sulfides. Appl. Catal. B Environ. 219, 683–692 (2017)

    Article  Google Scholar 

  13. A.J. Bard, L.R. Faulkner, J. Leddy, C.G. Zoski, Electrochemical methods: fundamentals and applications (Wiley, New York, 1980)

    Google Scholar 

  14. G.S. Ferdowsi, S.A. Seyedsadjadi, A. Ghaffarinejad, Ni nanoparticle modified graphite electrode for methanol electrocatalytic oxidation in alkaline media. J. Nanostruct. Chem. 5, 17–23 (2015). https://doi.org/10.1007/s40097-014-0124-z

    Article  CAS  Google Scholar 

  15. G.S. Ferdowsi, S.A. Seyedsadjadi, A. Ghaffarinejad, Electroless deposition of the Ni nanoparticles on the graphite electrode for glucose oxidation. Anal. Bioanal. Electrochem. 6, 379–391 (2014)

    CAS  Google Scholar 

  16. G.S. Ferdowsi, M. Rahgozar, S.A.S. Sadjadi, A. Ghaffarinejad, Electrocatalytic methanol oxidation with Ni-B and Ni-P electroless modified graphite electrodes. Anal. Bioanal. Electrochem. 11, 774–786 (2019)

    CAS  Google Scholar 

  17. L. Dai, Carbon-based catalysts for metal-free electrocatalysis (Curr. Opin, Electrochem, 2017)

    Book  Google Scholar 

  18. O. Hammerich, B. Speiser, Organic electrochemistry: revised and expanded (CRC Press, London, 2015)

    Book  Google Scholar 

  19. B. Zhang, M.-D. Zhou, M. Cokoja, J. Mink, S.-L. Zang, F.E. Kühn, Oxidation of sulfides to sulfoxides mediated by ionic liquids. Rsc Adv. 2, 8416–8420 (2012)

    Article  CAS  Google Scholar 

  20. E. Laviron, General expression of the linear potential sweep voltammogram in the case of diffusionless electrochemical systems. J. Electroanal. Chem. Interfacial Electrochem. 101, 19–28 (1979)

    Article  CAS  Google Scholar 

  21. M. Jafarian, M.R. Avei, I. Danaee, F. Gobal, M.G. Mahjani, Electrochemical oxidation of saccharose on copper (hydr) oxide-modified electrode in alkaline media. Chin. J. Catal. 31, 1351–1357 (2010)

    Article  CAS  Google Scholar 

  22. A. Ehsani, M. Bigdeloo, F. Asefi, M. Kiamehr, R. Alizadeh, Ternary nanocomposite of conductive polymer/chitosan biopolymer/metal organic framework: synthesis, characterization and electrochemical performance as effective electrode materials in pseudocapacitors. Inorg. Chem. Commun. 115, 107885 (2020)

    Article  CAS  Google Scholar 

  23. A. Ehsani, M.G. Mahjani, F. Babaei, H. Mostaanzadeh, Physioelectrochemical and DFT investigation of metal oxide/p-type conductive polymer nanoparticles as an efficient catalyst for the electrocatalytic oxidation of methanol. RSC Adv. 5, 30394–30404 (2015)

    Article  Google Scholar 

  24. A. Ehsani, M.G. Mahjani, M. Jafarian, A. Naeemy, Influence of ionic surfactant on physio-electrochemical properties and fractal dimension of poly ortho aminophenol film. Prog. Org. Coat. 69, 510–516 (2010)

    Article  CAS  Google Scholar 

  25. A. Ehsani, M.G. Mahjani, M. Jafarian, A. Naeemy, Electrosynthesis of polypyrrole composite film and electrocatalytic oxidation of ethanol. Electrochim. Acta. 71, 128–133 (2012)

    Article  CAS  Google Scholar 

  26. H.M. Shiri, A. Ehsani, Electrosynthesis of neodymium oxide nanorods and its nanocomposite with conjugated conductive polymer as a hybrid electrode material for highly capacitive pseudocapacitors. J. Colloid Interface Sci. 495, 102–110 (2017)

    Article  Google Scholar 

  27. M.G. Mahjani, A. Ehsani, M. Jafarian, Electrochemical study on the semiconductor properties and fractal dimension of poly ortho aminophenol modified graphite electrode in contact with different aqueous electrolytes. Synth. Met. 160, 1252–1258 (2010)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We gratefully acknowledge the financial support provided by K. N. Toosi University of Technology Research Council to conduct this research.

Author information

Authors and Affiliations

  1. Department of Chemistry, K. N. Toosi University of Technology, Tehran, Iran

    Ghodsiyeh Sadat Ferdowsi, Majid Jafarian & Vahid Khakyzadeh

Authors
  1. Ghodsiyeh Sadat Ferdowsi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Majid Jafarian
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Vahid Khakyzadeh
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Majid Jafarian.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ferdowsi, G.S., Jafarian, M. & Khakyzadeh, V. Introducing selective electro-oxidation of aryl and alkyl sulfides protocol in a novel environmentally friendly media. J IRAN CHEM SOC 17, 3009–3018 (2020). https://doi.org/10.1007/s13738-020-01978-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-020-01978-z

Keywords

Search

Navigation