Optimization of the synthesis parameters and analysis of characteristics of 1,1-diamino-2,2-dinitroethylene

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Authors

  • Nguyen Khac Phuong Hoa Military Technical Academy
  • Hoang Trung Huu (Corresponding Author) Military Technical Academy
  • Nguyen Mau Vuong Institute of Propellants and Explosives
  • Nguyen Xuan Thanh Institute of Propellants and Explosives

DOI:

https://doi.org/10.54939/1859-1043.j.mst.94.2024.70-77

Keywords:

FOX-7; 1,1-diamino-2,2-dinitroethylene; Synthesis; Optimization.

Abstract

2,2-Dinitroethene-1,1-diamine (FOX-7) is a low-sensitive explosive suitable for various energy-material applications. It can be synthesized based on the nitration and hydrolysis of heterocyclic precursors derived from 2-methylimidazole-4,5-dione (MID) or 2-methylpyrimidine-4,6-diol (MPD). However, more information about its optimal synthesis parameters during production from MPD as a starting material is needed. In this study, Taguchi's experimental design method was used to improve the yield of FOX-7. Verification of the results shows that the optimal synthesis parameters are as follows: the molar ratio of HNO3/MPD is 8, the reaction time is 180 minutes, and the reaction temperature is 15°C; the maximum yield of FOX-7 can reach 79.14%. Furthermore, the synthesized FOX-7 was identified and characterized by nuclear magnetic resonance (NMR) spectroscopy analysis, Fourier transforms infrared spectroscopy (FTIR), Raman spectroscopy analysis, and powder X-ray diffraction (PXRD).

References

[1]. Anniyappan, M., et al., "Review on advanced energetic materials for insensitive munition formulations". Combustion, Explosion, Shock Waves. Vol. 56, pp. 495-519, (2020). DOI: https://doi.org/10.1134/S0010508220050019

[2]. Latypov, N.V., et al., "Synthesis and reactions of 1, 1-diamino-2, 2-dinitroethylene". Tetrahedron. Vol. 54, No. 38, pp. 11525-11536, (1998). DOI: https://doi.org/10.1016/S0040-4020(98)00673-5

[3]. Bemm, U. and H. Östmark, "1, 1-Diamino-2, 2-dinitroethylene: a novel energetic material with infinite layers in two dimensions". Acta Crystallographica Section C: Crystal Structure Communications. Vol. 54, No. 12, pp. 1997-1999, (1998). DOI: https://doi.org/10.1107/S0108270198007987

[4]. Latypov, N., A. Langlet, and U. Wellmar, "Chemical compound suitable for use as an explosive, intermediate and method for preparing the compound", Google Patents, (2001).

[5]. Yuan, W.-S., et al., "Raman spectra and vibrational properties of FOX-7 under pressure and temperature: First-principles calculations". Spectrochimica Acta Part A: Molecular Biomolecular Spectroscopy. Vol. 293, pp. 122489, (2023). DOI: https://doi.org/10.1016/j.saa.2023.122489

[6]. Hervé, G. and G. Jacob, "Novel illustrations of the specific reactivity of 1, 1-diamino-2, 2-dinitroethene (DADNE) leading to new unexpected compounds". Tetrahedron. Vol. 63, No. 4, pp. 953-959, (2007). DOI: https://doi.org/10.1016/j.tet.2006.11.031

[7]. Šimková, L., et al., "Electrochemical investigation of 2, 2-dinitroethene-1, 1-diamine (FOX-7) in aqueous media". Journal of Solid State Electrochemistry. Vol. 15, pp. 2133-2139, (2011). DOI: https://doi.org/10.1007/s10008-011-1533-2

[8]. Astrat'ev, A.A., et al., "Some Specific Features of Acid Nitration of 2-Substituted 4,6-Dihydroxypyrimidines. Nucleophilic Cleavage of the Nitration Products". Russian Journal of Organic Chemistry. Vol. 37, No. 5, pp. 729-733, (2001). DOI: https://doi.org/10.1002/chin.200151070

[9]. Latypov, N.V., et al., "On the synthesis of 1, 1-diamino-2, 2-dinitroethene (FOX-7) by nitration of 4, 6-dihydroxy-2-methylpyrimidine". Organic process research development. Vol. 11, No. 1, pp. 56-59, (2007). DOI: https://doi.org/10.1021/op068010t

[10]. Chung, K., E. Goh, and J. Cho. Synthetic modification and scale-up process for 1, 1-diamino--2, 2-dinitroethene (FOX-7). in 36th International Annual Conference of ICT, Karlsruhe, Germany. (2005).

[11]. Chylek, Z., et al., "New trends in research of energetic materials-Proceedings of the VIII Seminar". Pardubice, Czech Republic. Vol. 207, No. (2005).

[12]. Taguchi, S., "Taguchi Methods and QFD: Hows and Whys for Management". American Supplier Institute, Michigan. Vol. No., pp. 1, (1987).

[13]. Viswanath, D.S., T.K. Ghosh, and V.M. Boddu, "Emerging energetic materials: Synthesis, physicochemical, and detonation properties". Springer (2018). DOI: https://doi.org/10.1007/978-94-024-1201-7

[14]. Dreger, Z.A., Y. Tao, and Y.M. Gupta, "High-pressure vibrational and polymorphic response of 1, 1-diamino-2, 2-dinitroethene single crystals: Raman spectroscopy". The Journal of Physical Chemistry A. Vol. 118, No. 27, pp. 5002-5012, (2014). DOI: https://doi.org/10.1021/jp5052062

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Published

22-04-2024

How to Cite

Nguyễn, H., H. Hoang Trung, V. Nguyen Mau, and T. Nguyen Xuan. “Optimization of the Synthesis Parameters and Analysis of Characteristics of 1,1-Diamino-2,2-Dinitroethylene”. Journal of Military Science and Technology, vol. 94, no. 94, Apr. 2024, pp. 70-77, doi:10.54939/1859-1043.j.mst.94.2024.70-77.

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Chemistry, Biology & Environment