On the Mechanism of Thermal Decomposition of 1,1-Diamino-2,2-dinitroethene (FOX-7) and its Cyclic Derivatives

• Autorzy: Krisyuk Boris E. , Zakharov Viktor V. , Chukanov Nikita V.

Identyfikatory

DOI

10.22211/cejem/118513

• Języki publikacji: EN

Abstrakty

EN

The thermal decomposition of 1,1-diamino-2,2-dinitroethene (I) and its cyclic derivatives 2-(dinitromethylene)-1,3-diazacyclopentane (II), 2-(dinitromethylene)-1,3-diazacyclohexane (III) and 2-(dinitromethylene)-1,3-diazacycloheptane (IV) was investigated by quantum chemistry methods (PBE/cc-pVDZ), as well as DSC and TG. According to both the theoretical and experimental data, the thermal stability of compounds I-IV increases in the sequence IV < I ≈ III < II.

Słowa kluczowe

EN

quantum chemical calculation; FOX-7; thermal decomposition; DSC; TG

• Czasopismo: Central European Journal of Energetic Materials
• Rocznik: 2020
• Tom: Vol. 17, no. 1
• Strony: 20--30
• Opis fizyczny: Bibliogr. 25 poz., rys.

Twórcy

autor

Krisyuk Boris E.

• Institute of Problems of Chemical Physics, Russian Academy of Sciences, 142432 Chernogolovka, Moscow Region, Russia

autor

Zakharov Viktor V.

• Institute of Problems of Chemical Physics, Russian Academy of Sciences, 142432 Chernogolovka, Moscow Region, Russia

autor

Chukanov Nikita V.

• Institute of Problems of Chemical Physics, Russian Academy of Sciences, 142432 Chernogolovka, Moscow Region, Russia

Bibliografia

• [1] Latypov, N.V.; Bergman, J.; Langlet, A.; Wellmar, U.; Bemm, U. Synthesis and Reactions of 1,1-Diamino-2,2-dinitroethylene. Tetrahedron 1998, 54: 11525-11536.
• [2] Bellamy, A.J. FOX-7, High Energy Density Materials. In: Structure and Bonding. (Klapötke, T.M. (Vol. Ed.), Mingos, D.M.P. (Series Ed.)) vol. 125, pp. 1-33, Springer, Berlin, 2007.
• [3] Sikder, A.K.; Sikder, N. A Review of Advanced High Performance, Insensitive and Thermally Stable Energetic Materials Emerging for Military and Space Applications. J. Hazard. Mater. 2004, 112(1-2): 1-15.
• [4] Trzciński, W.A.; Cudziło, S.; Chyłek, Z.; Szymańczyk, L. Detonation Properties of 1,1-Diamino-2,2-dinitroethene (DADNE). J. Hazard. Mater. 2008, 157: 605-612.
• [5] Nair, U.R.; Asthana, S.N.; Subhananda Rao, A.; Gandhe, B.R. Advances in High Energy Materials. Def. Sci. J. 2010, 60(2): 137-151.
• [6] Evers, J.; Klapötke, T.M.; Mayer, P.; Oehlinger, G.; Welch, J. Alpha- and Beta-FOX-7, Polymorphs of a High Energy Density Material, Studied by X-ray Single Crystal and Powder Investigations in the Temperature Range from 200 to 423 K. Inorg. Chem. 2006, 45: 4996-5007.
• [7] Crawford, M.-J.; Evers, J.; Göbel, M.; Klapötke, T.M.; Mayer, P.; Oehlinger, G.; Welch, J.M. Gamma-FOX-7: Structure of a High Energy Density Material Immediately Prior to Decomposition. Propellants Explos. Pyrotech. 2007, 32: 478-495.
• [8] Zakharov, V.V.; Chukanov, N.V.; Chervonnyi, A.D.; Vozchikova, S.A.; Korsounskii, B.L. Kinetics of Reversible Polymorphic Transitions in Energetic Materials. Phase Transitions α → β and β → α in 1,1-Diamino-2,2-dinitroethylene. Russ. J. Phys Chem. B, 2014, 8: 822-828.
• [9] Zakharov, V.V.; Chukanov, N.V.; Dremova, N.N.; Kazakov, A.I.; Volkova, N.N.; Chervonnyi, A.D.; Korsounskii, B.L.; Shilov, G.V. High-Temperature Structural Transformations of 1,1-Diamino-2,2-dinitroethene (FOX-7). Propellants Explos. Pyrotech. 2016, 41: 1006-1012.
• [10] Baum, K.; Bigelow, S.S.; Nguyen, N.V.; Archibald, T.; Gilardi, R.; Flippen-Anderson, J.L.; George, C. Synthesis and Reactions of 1,l-Diiododinitroethylene. J. Org. Chem. 1992, 57: 235-241.
• [11] Gindulyte, A.; Massa, L.; Huang, L.; Karle, J. Proposed Mechanism of 1,1-Diaminodinitroethylene Decomposition: a Density Functional Theory Study. J. Phys. Chem. A 1999, 103: 11045-11051.
• [12] Burnham, F.K.; Weese, R.K.; Wang, R.; Kwok, Q.S.M.; Jones, D.E.G. Thermal Properties of FOX-7. Int. Annual Conf. ICT, Proc., 35th, Karlsruhe, Germany, 2005, 70-81.
• [13] Sinditskii, V.P.; Levshenkov, A.I.; Egorshev, V.Y.; Serushkin, V.V. Study on Combustion and Thermal Decomposition of 1,1-Diamino-2,2-dinitroethylene (FOX-7). Int. Pyrotech. Semin. EuroPyro 2003, Proc., 8th, 2003, 1: 299-311.
• [14] Volkova, N.N.; Kazakov, A.I.; Danilchik, A.V.; Shastin, A.V.; Shilov, G.V. The Kinetic Regularities of the Heat Release in the Thermal Decomposition of 1,1-Diamino-2,2-dinitroethene (FOX-7) and Its Cyclic Homologues. New Trends Res. Energ. Mater., Proc. Semin., 21th, Pardubice, Czech Republic, 2018, 1143-1152.
• [15] Kiselev, V.G.; Gristan, N.P. Unexpected Primary Reactions for Thermolysis of 1,1-Diamino-2,2-dinitroethylene (FOX-7) Revealed by ab initio Calculations. J. Phys. Chem. A 2014, 118: 8002-8008.
• [16] Krisyuk, B.E.; Veretin V.S. About Some Primary Reactions of Thermolysis of 1,1-Diamino-2,2-dinitroethylene (FOX-7) Revealed by DFT Calculations. Part 1,. Direct Hydrogen Transfer to Nitro Group. Butlerov Commun. 2017, 49: 31-35.
• [17] Zhang, Y.; Sun, Q.; Xu, K.; Song, J.; Zhao, F. Review on the Reactivity of 1,1-Diamino-2,2-dinitroethylene (FOX-7). Propellants Explos. Pyrotech. 2016, 41: 35-52.
• [18] Khrapkovskii, G.M.; Shamov, A.G.; Nikolaeva, E.V.; Chachkov, D.V. Mechanisms of the Gas-Phase Decomposition of C-Nitro Compounds Inferred from Quantum Chemical Calculations. Russ. Chem. Rev. 2009, 78(10): 903-943.
• [19] Liu, Y.; Li, F.; Sun, H. Thermal Decomposition of FOX-7 Studied by ab initio Molecular Dynamics Simulations. Theor. Chem. Acc. 2014, 133: 1567.
• [20] Jiang, H.; Jiao, Q.; Zhang, C. Early Events When Heating 1,1-Diamino-2,2-dinitroethylene: Self-Consistent Charge Density-Functional Tight-Binding Molecular Dynamics Simulations. J. Phys. Chem. C 2018, 122: 15125-15132.
• [21] Astrat’ev, A.A.; Dashko, D.V.; Mershin, A.Yu.; Stepanov, A.I.; Urazgil’deev, N.A. Some Specific Features of Acid Nitration of 2-Substituted 4,6-Dihydroxypyrimidines. Nucleophilic Cleavage of the Nitration Products. Russ. J. Organic Chem. 2001, 37: 729-733.
• [22] Shastin, A.V.; Korsunskii, B.L.; Lodygina V.P. Reactions of 1,1-Diamino-2,2-dinitroethylene with Diamines. Russ. J. App. Chem. 2009, 82: 1805-1806.
• [23] Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G.A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H.P.; Izmaylov, A.F.; Bloino, J.; Zheng, G.; Sonnenberg, J.L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J.A., Jr.; Peralta, J.E.; Ogliaro, F.; Bearpark, M.; Heyd, J.J.; Brothers, E.; Kudin, K.N.; Staroverov, V.N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J.C.; Iyengar, S.S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J.M.; Klene, M.; Knox, J.E.; Cross, J.B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R.E.; Yazyev, O.; Austin, A.J.; Cammi, R.; Pomelli, C.; Ochterski, J.W.; Martin, R.L.; Morokuma, K.; Zakrzewski, V.G.; Voth, G.A.; Salvador, P.; Dannenberg, J.J.; Dapprich, S.; Daniels,A.D.; Farkas, O.; Foresman, J.B.; Ortiz, J.V.; Cioslowski, J.; Fox, D.J. Gaussian 09, Revision B.01. Gaussian, Inc., Wallingford CT, 2010.
• [24] Adamo, C.; Barone, V. Toward Reliable Density Functional Methods without Adjustable Parameters: The PBE0 Model. J. Chem. Phys. 1999, 110: 6158-6169.
• [25] Ignatov, S.K. Moltran – Program for Visualization of Molecular Data and Calculations of Thermodynamic Parameters. Lobachevsky State University of Nizhny Novgorod, Russia, http://qchem.unn.ru/moltran, http://github.com/skignatov/moltran [accessed February 3, 2020].

Uwagi

Opracowanie rekordu ze środków MNiSW, umowa Nr 461252 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2020).