Skip to main content
Log in

Electrochemical investigation of 2,2-dinitroethene-1,1-diamine (FOX-7) in aqueous media

  • Original Paper
  • Published:
Journal of Solid State Electrochemistry Aims and scope Submit manuscript

Abstract

Redox properties of 2,2-dinitroethene-1,1-diamine (FOX-7) were electrochemically investigated by DC polarography, cyclic voltammetry and preparative electrolyses, and electroreduction products were analysed. The polarographic reduction of FOX-7 in aqueous buffered solutions exhibited a total sum of limiting currents corresponding to the expected 18 electrons. This result fits well with the chemical reduction of this energetic material resulting in ethan-1,2-diamine. Exhaustive electrolysis, however, did not yield this product and the passed charge for total degradation of this compound corresponds only to 4–7 F. As the main products, gaseous N2, N2O, NO and NH3 were proved by combination EC–GC–MS and, besides that, nitrite anions and ammonia ions were identified by other methods. All these observations suggest that instead of electrochemical reduction, an electrochemically initiated degradation process accompanying the exhaustive electrolysis occurs. This seems to be analogous to the chain of reactions during explosion, which are slowed down by a very low concentration and cooled by the solvent.

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

Access this article

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

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. Latypov NV, Bergman J (1998) Tetrahedron 54:11525–11536

    Article  CAS  Google Scholar 

  2. Latypov N, Langlet A, Wellmar U (1999) Pct Int. Appl., WO 9903818 A1

  3. Bellamy AJ, Latypov N, Goede P (2003) J Chem Research 9:529–530

    Article  Google Scholar 

  4. Cibulka R (2004) Report: Agreement No. 4621/2004/VÚPCH among Explosia, a. s. and VŠCHT Praha

  5. Latypov N, Johansson M, Holmgren E (2007) Org Process Res Dev 11:56–59

    Article  CAS  Google Scholar 

  6. Dorochov VA, Gordeev MF, Bogdanov VS, Lajchter AL, Kislij VP, Semenov VV (1990) Izv An sssr Ser Chim 11:2660

    Google Scholar 

  7. Trzcinski WA, Cudzilo S, Chylek Z, Szymanczyk L (2008) J Hazard Mater 157:605–612

    Article  CAS  Google Scholar 

  8. Bellamy A (2007) J Struct Bond 125:1–33

    Article  CAS  Google Scholar 

  9. Šimková L, Liška F, Ludvík J (2011) Current Org Chem 15:2983–2995

    Google Scholar 

  10. Zuman P (1969) The elucidation of organic electrode processes. Academic, New York, p 23

    Google Scholar 

  11. Lund H (1991) Cathodic reduction of nitro and related compounds. In: Lund H, Baizer MM (eds) Organic electrochemistry, 3rd edn. Marcel Dekker, New York, pp 404–405

    Google Scholar 

  12. Ludvík J, Riedl F, Liška F, Zuman P (1998) J Electroanal Chem 457:177–190

    Article  Google Scholar 

  13. Ludvík J, Riedl F, Liška F, Zuman P (1998) Electroanalysis 10:869–876

    Article  Google Scholar 

  14. Jander G, Blasius E (1979) Lehrbuch der analytischen und präparativen anorganischen Chemie. Hirzel, Leipzig

  15. Zong H-H, Huang Y-G, Shu Y-J, Wang X-F (2006) Hanneng Cailiao 14(6):425–428

    CAS  Google Scholar 

  16. Zong H, Shu Y, Huang Y, Wang X (2006) Proceedings of the 9th Seminar, New Trends in Research of Energetic Materials, Pardubice, Czech Republic, Apr. 19–21:816–823

Download references

Acknowledgement

This work was done with the support of the project KONTAKT (Ministry of Education, Youth and Sports of the Czech Republic) No. ME 09 002. The authors are grateful to Ing. Zdeněk Jalový from the University Pardubice for granting the sample and to Prof. F. Liška for valuable consultations.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jiří Ludvík.

Additional information

This article is dedicated to the 70th birthday of Fritz Pragst.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Šimková, L., Klíma, J., Sazama, P. et al. Electrochemical investigation of 2,2-dinitroethene-1,1-diamine (FOX-7) in aqueous media. J Solid State Electrochem 15, 2133–2139 (2011). https://doi.org/10.1007/s10008-011-1533-2

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10008-011-1533-2

Keywords

Navigation