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4,6-Diazido-N-(2,4,6-trinitrophenyl)-1,3,5-triazin-2-amine (TNADAzT) and Its Silver Salt − Synthesis and Characterization

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Języki publikacji
EN
Abstrakty
EN
4,6-Diazido-N-(2,4,6-trinitrophenyl)-1,3,5-triazin-2-amine (TNADAzT) and its silver salt (AgTNADAzT) were prepared and characterized. Elemental analysis, FTIR, NMR, DSC, AAS and X-ray diffraction were used for analytical characterization. The sensitivities of TNADAzT and AgTNADAzT were determined and compared with common explosives and MTX-1. The crystal density of TNADAzT is 1.794 g·cm−3 and its heat of formation 899 kJ·mol−1. The sensitivity of TNADAzT to impact and friction slightly exceeds PETN; the sensitivity to electrostatic discharge is lower than RDX. The sensitivity of AgTNADAzT is on the level of a primary explosives (between mercury fulminate and PETN). The initiation efficiency of AgTNADAzT is higher than 200 mg (acceptor PETN compressed by 64-70 MPa) and therefore excludes it from practical use as a primary explosive in detonators.
Słowa kluczowe
Rocznik
Strony
304--320
Opis fizyczny
Bibliogr. 32 poz., rys., tab.
Twórcy
autor
  • Institute of Energetic Materials, Faculty of Chemical Technology, University of Pardubice, Studentska 95, 532 10 Pardubice, Czech Republic
autor
  • Institute of Energetic Materials, Faculty of Chemical Technology, University of Pardubice, Studentska 95, 532 10 Pardubice, Czech Republic
autor
  • Institute of Energetic Materials, Faculty of Chemical Technology, University of Pardubice, Studentska 95, 532 10 Pardubice, Czech Republic
  • Institute of Energetic Materials, Faculty of Chemical Technology, University of Pardubice, Studentska 95, 532 10 Pardubice, Czech Republic
autor
  • Institute of Energetic Materials, Faculty of Chemical Technology, University of Pardubice, Studentska 95, 532 10 Pardubice, Czech Republic
autor
  • Institute of Energetic Materials, Faculty of Chemical Technology, University of Pardubice, Studentska 95, 532 10 Pardubice, Czech Republic
autor
  • Institute of Energetic Materials, Faculty of Chemical Technology, University of Pardubice, Studentska 95, 532 10 Pardubice, Czech Republic
autor
  • Institute of Energetic Materials, Faculty of Chemical Technology, University of Pardubice, Studentska 95, 532 10 Pardubice, Czech Republic
Bibliografia
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  • [2] Bagal, L. I. Chemistry and Technology of Primary Explosives. Mashinostrojenije, Moskva 1975.
  • [3] Matyáš, R.; Pachman, J. Primary Explosives. Springer, Heidelberg 2013, pp. 32, 111-115; ISBN 978-3-642-28435-9.
  • [4] Fedoroff, B. T.; Sheffield, O. E. Encyclopedia of Explosives and Related Items. Vol. 3, Picatinny Arsenal, New Jersey 1966, pp. C590-C591.
  • [5] Huynh, M. V.; Coburn, M. D.; Meyer, T. J.; Wetzer, M. Green Primaries: Environmentally Friendly Energetic Complexes. PNAS 2006, 103: 5409-5412.
  • [6] Huynh, M. V.; Coburn, M. D.; Meyer, T. J.; Wetzer, M. Green Primary Explosives: 5-Nitrotetrazolato-N2-ferrate Hierarchies. PNAS 2006, 103: 10322-10327.
  • [7] Mehta, N.; Cheng, G.; Cordaro, E.; Naik, N.; Lateer, B.; Hu, C.; Stec, D; Yang, K. Performance Testing of Lead-free Stab Detonator. NDIA 50th Annual Fuze Conference, Norfolk, USA 2006.
  • [8] Fronabarger, J.; Sitzmann, M. E.; Williams, M. D. Method for Azidotriazole, Nitrosoguanazine, and Related Compounds. Patent US 7375221 B1, 2008.
  • [9] Musil, T.; Matyáš, R.; Růžička, A. 4,6-Diazido-N-nitro-1,3,5-triazin-2-amine (DANT) − Synthesis and Characterization. Propellants Explos. Pyrotech. 2012, 37: 275-281.
  • [10] Huynh, M. H. V.; Hiskey, M. A.; Hartline, E. L.; Montoya, D. P.; Gilardi, R. Polyazido High-nitrogen Compounds: Hydrazo- and Azo-1,3,5-triazine. Angew. Chem., Int. Ed. 2004, 43: 4924-4928.
  • [11] Huynh, M. H. V.; Hiskey, M. A.; Pollarod, C. J.; Montoya, D. P.; Hartline, E. L.; Gilardi, R. 4,4’,6,6’-Tetrasubstituted Hydrazo- and Azo-1,3,5-triazines. J. Energ. Mater. 2004, 22: 217-229.
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  • [13] Yan, Q. L.; Musil, T; Zeman, S.; Matyáš, R.; Shi, X. B.; Vlček, M.; Pelikán, V. Preparation, Morphologies and Thermal Behavior of High Nitrogen Compound 2-Amino-4,6-diazido-s-triazine and Its Derivatives. Thermochim. Acta 2015, 604: 106-114.
  • [14] Pirkl, J.; Fisar, C. 2-Anilino-4,6-dichlorotriazine and Derivatives. Patent CS 171995, 1978.
  • [15] Azev, Yu. A.; Guselnikova, O. L.; Klyuev, N. A.; Shorshnev, C. V.; Rusinov, V. L.; Khupakhin, O. N. Products of Reactions of Azido Derivatives of s-Triazine with some O- and N-Nucleophiles. Zh. Org. Khim. 1995, 31: 1566-1572.
  • [16] Fronabarger, J. W.; Williams, M. D.; Stern, A. G.; Parrish, D. A. MTX-1 – A Potential Replacement for Tetrazene in Primers. Cent. Eur. J. Energ. Mater. 2016, 13: 33-52.
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  • [18] Matyáš, R.; Šelešovský, J.; Musil, T. Sensitivity to Friction for Primary Explosives. J. Hazard. Mater. 2012, 213-214: 236-241.
  • [19] Kucerova, J.; Svobodova, Z.; Knotek, P.; Palarcik, J.; Vlcek, M.; Kincl, M.; Horak, D.; Autebert, J.; Viovy, J.-L.; Bilkova, Z. PEGylation of Magnetic Poly(glycidyl methacrylate) Microparticles for Microfluidic Bioassays. Mater. Sci. Eng. C 2014, 40: 308-315.
  • [20] Klapetek, P.; Nečas, D.; Anderson, C. Gwyddion − Free SPM Data Analysis Software; v. 2.25, 2011.
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  • [22] Coppens, P. Evaluation of Absorption and Extinction in Single-crystal Structure Analysis. In: Crystallographic Computing (Ahmed, F. R.; Hall, S. R.; Huber, C. P., Eds.), Munksgaard, Copenhagen 1970, pp. 255-263.
  • [23] Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. Completion and Refinement of Crystal Structures with SIR92. J. Appl. Crystal. 1993, 26: 343-350.
  • [24] Sheldrick, G. M. SHELXL-97. University of Göttingen, Göttingen 1997.
  • [25] Strnad, J.; Majzlík, J. Determination of Electrostatic Spark Sensitivity of Energetic Materials. New Trends Res. Energ. Mater., Proc. Semin., 4th, Pardubice, Czech Republic 2001, 303-307.
  • [26] Knaggs, I. E. The Crystal Structure of Cyanuric Triazide. Proc. R. Soc. London, Ser. A 1935, 15: 576-302.
  • [27] Kessenich, E.; Klapötke, T. M.; Knizek, J.; Noth, H.; Schulz, A. Characterization, Crystals Structure of 2,4-Bis(triphenylphosphanimino)tetrazolo[5,1-a]-[1,3,5] triazine, and Improved Crystal Structure of 2,4,6-Triazido-1,3,5-triazine. Eur. J. Inorg. Chem. 1998, 12: 2013-2016.
  • [28] Huynh, M. H. V.; Hiskey, M. A.; Hartline, E. L.; Montoya, D. P.; Gilardi, R. Polyazido High-nitrogen Compounds: Hydrazo-and Azo-1,3,5-triazine. Angew. Chem., Int. Ed. 2004, 43: 4924-4928.
  • [29] Chapyshev, S. V.; Lavitsky, V. F.; Akimov, A. V.; Misochko, E. Ya.; Shastin, A. V.; Korchagin, D. V.; Shilov, G. V.; Aldoshin, S. M. Photochemical Generation of Triplet-triplet Nitrene Pairs in Aromatic Diazide Crystals. Izv. Akad. Nauk SSSR, Ser. Khim. (Russ. Chem. Bull.) 2008, 57: 524-531.
  • [30] Huang, Y.; Zhang, Y.; Shreeve, J. M. Nitrogen-rich Salts Based on Energetic Nitroaminodiazido[1,3,5]triazine and Guanazine. Chem. Eur. J. 2011, 17: 1538-1546.
  • [31] Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. Tables of Bond Lengths Determined by X-ray and Neutron Diffraction. Part 1. Bond Lengths in Organic Compounds. J. Chem. Soc., Perkin Trans. 2 1987, S1-S19.
  • [32] Meyer, R.; Köhler, J.; Homburg, A. Explosives. 6th ed., Wiley-VCH, Weinheim 2007, p. 141; ISBN 978-3-527-31656-4.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-ac71a7ca-380d-453e-81c0-009688106b2f
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