Skip to main content
Log in

Thermochemical and Energy Characteristics of N-(2,2-bis(methoxy-NNO-azoxy)ethyl)nitramines

  • Published:
Combustion, Explosion, and Shock Waves Aims and scope

Abstract

The standard enthalpies of formation of 1,1-bis(methoxy-NNO-azoxy)-3-nitro-3-azabutane and 1,1,8,8-tetrakis (methoxy-NNO-azoxy)-3,6-dinitro-3,6-diazaoctane were experimentally determined to be 87.7 \(\pm\) 3.9 and 283.8 \(\pm\) 6.2 kJ/mol, respectively. Calculations have shown that solid composite propellants containing these two compounds as gasifying components in metal-free compositions based on an active binder and ammonium perchlorate are inferior in the maximum achievable effective impulse at the third stage of the rocket system \(I_{ef}\)(3) to compositions based on HMX, but in designing special compositions with a limited content of organic explosive (not higher than 30–35%), these two compounds provide 5–10 s higher values of \(I_{ef}\)(3) than when using HMX.

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

Similar content being viewed by others

REFERENCES

  1. I. N. Zyuzin, A. I. Kazakov, D. B. Lempert, I. A. Vatsadze, L. S. Kurochkina, and A. V. Nabatova, “Thermochemical and Energy Characteristics of Alkoxy-NNO-Azoxy Derivatives of Pyrazole and Nitropyrazoles," Fiz. Goreniya Vzryva 55 (3), 92–99 (2019) [Combust., Expl., Shock Waves. 55 (3), 327–334 (2019)].

  2. I. N. Zyuzin, N. L. Dalinger, and K. Yu. Suponitskii, “N-[2,2-bis(methoxy-NNO-azoxy)ethyl]pyrazoles," Khim. Geterotsykl. Soed. 53 (6/7), 702–709 (2017).

  3. I. N. Zyuzin, “Azido Derivatives of Geminal Bis(alkoxy-NNO-azoxy) Compounds," Zh. Org. Khim. 51 (2), 187–191 (2015) [Russ. J. Org. Chem. 51 (2), 174–179 (2015)].

  4. I. N. Zyuzin, K. Yu. Suponitsky, and A. B. Sheremetev, “2,2-bis(methoxy-NNO-azoxy)ethyl Derivatives of 4,8-dihydro-bis-furazano[3,4-\(b\):3′4′-\(e\)]pyrazine: The Synthesis and \(X\)-ray Investigation," J. Heterocycl. Chem. 49 (3), 561–565 (2012).

  5. I. N. Zyuzin and D. B. Lempert, “Synthesis of 1,1-bis(methoxy-NNO-azoxy)-3,3,3-trinitopropane from 1,1-bis(methoxy-NNO-azoxy)ethene with Nitroform," Izv. Akad. Nauk, Ser. Khim., No. 10, 2108–2109 (2009) [Russ. Chem. Bull.58, 2173–2174 (2009)].

  6. E. P. Kirpichev, I. N. Zyuzin, V. V. Avdonin, Yu. I. Rubtsov, and D. B. Lempert, “Standard Enthalpies of Formation of Alkoxy-NNO-Azoxy Compounds," Zh. Fiz. Khim. 80 (9), 1543–1546 (2006) [Russ. J. Phys. Chem. 80 (9), 1359–1362 (2006)].

  7. G. A. Marchenko, A. S. Mukhametzyanov, I. V. Tselinskii, and A. S. Ermoshkin, “N′-alkoxydiazene N-oxide Derivatives. II. Interaction of bis(N-hydroxy-N′-methoxydiazenyl)methyl methane with Nucleophilic-Reagents," Zh. Org. Khim.21 (7), 1429–1431 (1985) [J. Org. Chem. USSR,21, 1300 (1985)].

  8. I. N. Zyuzin, N. I. Golovina, B. S. Fedorov, G. V. Shilov, and G. N. Nechiporenko, “Synthesis and structure of 2,3,6,8,10,13,14-heptaaza-6,8,10-trinitro-4,12-dioxapentadeca-2,13-diene-2,14-bisoxide," Izv. Akad. Nauk. Ser. Khim., No. 3, 726–728 (2003) [Russ. Chem. Bull.52 (3), 761–763 (2003).

  9. I. N. Zyuzin, Z. G. Aliev, T. K. Goncharov, E. L. Ignatieva, and S. M. Aldoshin, “Structure of a Bimolecular Crystal 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane and Methoxy-NNO-Azoxymethane," Zh. Struct. Khim. 58 (1), 119–124 (2017) [J. Struct. Chem. 58, 113–118 (2017)].

  10. Ya. O. Inozemtsev, A. B. Vorob’ev, A. V. Inozemtsev, and Yu. N.  Matyushin, “Calorimetry of Energetic Compounds," Gorenie Vzryv, No. 7, 260–270 (2014).

  11. A. I. Kazakov, D. V. Dashko, A. V. Nabatova, A. I. Stepanov, and D. B. Lempert, “Thermochemical and Energy Characteristics of DNTF and DNFF," Fiz. Goreniya Vzryva 54 (2), 27–38 (2018). [Combust., Expl., Shock Waves 54 (2), 147–157 (2018); DOI: 10.1134/S001050821802003X].

  12. Experimental Thermochemistry, Vol. 1:Measurement of Heats of Reaction, Ed. by F. D. Rossini (Intersciences, New York, 1956).

  13. Thermal Constants of Substances: A Handbook, Ed. by Acad. V. P. Glushko (Izd. Akad. Nauk SSSR, Moscow, 1965) [in Russian].

  14. T. F. Vasil’eva, E. N. Zhil’tsova, and A. A. Vvedenskii, “Enthalpies of Combustion of N, N-dimethylformamide and N, N-dimethylacetamide," Zh. Fiz Khim. 46 (2), 541–542 (1972).

  15. L. M. Kostikova, E. A. Miroshnichenko, and Y. N. Matyushin, “The Energies of Dissociation Bonds and Efficient Energies of Interaction in Nitroamines," in Energetic Materials: Analysis, Diagnostics and Testing: 31st Int. Annu. Conf. of ICT(Karlsruhe, 2000), pp. 50.1–11.

  16. D. B. Lempert, I. N. Zyuzin, A. V. Nabatova, A. I. Kazakov, and L. S. Yanovskii, “Thermochemical and Energy Characteristics of 1,4-diethynylbenzene," Fiz., Goreniya Vzryva 55 (6), 14–18 (2019) [Combust. Expl., Shock Waves 55 (6), 644–647 (2019)].

  17. D. B. Lempert, A. I. Kazakov, A. B. Sheremetev, A. G. Gladyshkin, A. V. Nabatova, L. S. Yanovsky, “Experimental Determination of the Standard Enthalpy of Formation of 4H, 8H-bis(furazano)[3,4-b:3′, 4′-e]pyrazine and Evaluation of Its Performance As a Dispersant of Solid Fuels," Izv. Akad. Nauk SSSR, Ser. Khim., No. 10, 1856–1859 (2019) [Russ. Chem. Bull. 68, 1856–1859 (2019)].

  18. Y. N. Surikova et al., “Thermochemical and Quantum Chemical Characteristics of Piperazine, Furazanopiperazine and Difurazanopiperazine Derivatives Nitroamines," inEnergetic Materials: Analysis, Diagnostics, and Testing, 33rd Int. Annu. Conf. of ICT (Karlsruhe, 2002), p. 59.

  19. L. F. Chertanova, A. I. Yanovskii, Yu. T. Struchkov, G. A. Marchenko, V. F. Sopin, “X-ray Diffraction Structural Analysis of Bis(N-oxide-N′-methoxydiazenyl)-methylmethane and Bis(N-oxide-N′-methoxydiazenyl)(N″-methyl-N″-nitraminomethyl) Methane," Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 1200–1202 (1989) [Russ. Chem. Bull. 38 (5), 1092–1094 (1989)].

  20. G. Pavlovets and V. Tsutsuran, Physicochemical Properties of Powders and Propellants (Izd. Min. Obor. Ross. Fed., Moscow, 2009) [in Russian].

  21. B. D. Trusov, “TERRA Software System for Modeling APse and Chemical Equilibria," in Abstr. of XIV Int. Conf. on Chem. Thermodyn. (Inst. of Chemistry, St. Petersburg State Univ., St. Petersburg, 2002), 483–484.

  22. D. Lempert, G. Nechiporenko, and G. Manelis, “Energetic Characteristics of Solid Composite Propellants and Ways of Energy Increasing," Centr. Eur. J. Energ. Mater. 3 (4), 73–80 (2006).

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zyuzin, I.N., Lempert, D.B., Nabatova, A.V. et al. Thermochemical and Energy Characteristics of N-(2,2-bis(methoxy-NNO-azoxy)ethyl)nitramines. Combust Explos Shock Waves 56, 464–470 (2020). https://doi.org/10.1134/S0010508220040103

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0010508220040103

Keywords

Navigation