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4-Amino-3-hydrazino-1,2,4-triazole: a Precursor for the Preparation of Divalent Energetic Materials

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Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
4-Amino-3-hydrazino-1,2,4-triazole (AHT) was developed as a divalent cation. The multivalent structure can be used to increase the number of nitrogen-rich heterocycles, thereby increasing the heat of formation and improving the detonation performance. Herein we report on a family of divalent energetic salts, which exhibit excellent properties, viz. acceptable density, good detonation performance, and desirable thermal and impact stabilities. The structural features of the salts were further determined by single-crystal X-ray diffraction. In addition, the detonation properties calculated for these energetic salts identified them as competitively energetic compounds.
Rocznik
Strony
18--29
Opis fizyczny
Bibliogr. 41 poz., rys., tab.
Twórcy
autor
  • Nanjing University of Science and Technology Xiaolingwei 200, 210094 Nanjing, Jiangsu, China
autor
  • Nanjing University of Science and Technology Xiaolingwei 200, 210094 Nanjing, Jiangsu, China
autor
  • Nanjing University of Science and Technology Xiaolingwei 200, 210094 Nanjing, Jiangsu, China
  • Nanjing University of Science and Technology Xiaolingwei 200, 210094 Nanjing, Jiangsu, China
autor
  • Nanjing University of Science and Technology Xiaolingwei 200, 210094 Nanjing, Jiangsu, China
Bibliografia
  • [1] Yin, P.; He, C.; Shreeve, J. M. Fused Heterocycle-based Energetic Salts: Alliance of Pyrazole and 1,2,3-Triazole. J. Mater. Chem. A 2015, 4: 1514-1519.
  • [2] Tang, Y.; Gao, H.; Mitchell, L. A.; Parrish, D. A.; Shreeve, J. M. Syntheses and Promising Properties of Dense Energetic 5,5’-Dinitramino-3,3’-azo-1,2,4-oxadiazole and its Salts. Angew. Chem., Int. Ed. 2016, 55: 3200-3203.
  • [3] Zhang, J.; Dharavath, S.; Mitchell, L. A.; Parrish, D. A.; Shreeve, J. M. Energetic Salts Based on 3,5-Bis(dinitromethyl)-1,2,4-triazole Monoanion and Dianion: Controllable Preparation, Characterization, and High Performance. J. Am. Chem. Soc. 2016, 138: 7500-7503.
  • [4] Badgujar, D. M.; Talawar, M. B.; Asthana, S. N.; Mahulikar, P. P. Advances in Science and Technology of Modern Energetic Materials: an Overview. J. Hazard. Mater. 2008, 151: 289-305.
  • [5] Gao, H.; Shreeve, J. M. Azole-based Energetic Salts. Chem. Rev. 2011, 111: 7377-7436.
  • [6] Fischer, D.; Klapötke, T. M.; Stierstorfer, J.; Szimhardt, N. 1,1’-Nitramino-5,5’-bitetrazoles. Chem. - Eur. J. 2016, 22: 4966-4970.
  • [7] Abe, T.; Tao, G. H.; Joo, Y. H.; Huang, Y. G.; Twamley, B.; Shreeve, J. M. Activation of the C-F Bond: Transformation of CF3N=N- into 5-Azidotetrazoles. Angew. Chem. 2008, 120: 7195-7198.
  • [8] Zhang, Y.; Guo, Y.; Joo, Y. H.; Parrish, D. A.; Shreeve, J. M. 3,4,5-Trinitropyrazolebased Energetic Salts. Chem. - Eur. J. 2010, 16: 10778-10784.
  • [9] Xue, H.; Gao, H.; Twamley, B.; Shreeve, J. M. Energetic Salts of 3-Nitro-1,2,4-triazole-5-one, 5-Nitroaminotetrazole, and other Nitro-Substituted Azoles. Chem. Mater. 2007, 19: 1731-1739.
  • [10] Wang, K.; Parrish, D. A.; Shreeve, J. M. 3-AzidoN-nitro-1H -1,2,4-triazol-5-amine-based Energetic Salts. Chem. - Eur. J. 2011, 17: 14485-14492.
  • [11] Lin, Q. H.; Li, Y. C.; Li, Y. Y.; Wang, Z.; Liu, W.; Qi, C.; Pang, S. P. Energetic Salts Based on 1-Amino-1,2,3-triazole and 3-Methyl-1-amino-1,2,3-triazole. J. Mater. Chem. 2011, 22: 666-674.
  • [12] Lin, Q. H.; Li, Y. C.; Qi, C.; Liu, W.; Wang, Y.; Pang, S. P. Nitrogen-rich Salts Based on 5-Hydrazino-1H-tetrazole: a New Family of High-density Energetic Materials. J. Mater. Chem. A 2013, 1: 6776-6785.
  • [13] Fischer, N.; Izsák, D.; Klapötke, T. M.; Stierstorfer, J. The Chemistry of 5-(Tetrazol-1-yl)-2H-tetrazole: an Extensive Study of Structural and Energetic Properties. Chem. - Eur. J. 2013, 19: 8948-8957.
  • [14] Huang, Y.; Zhang, Y. Nitrogen-rich Salts Based on Energetic Nitroaminodiazido[1,3,5] triazine and Guanazine. Chem. - Eur. J. 2011, 17: 1538-1546.
  • [15] Liu, W.; Lin, Q. H.; Yang, Y. Z.; Zhang, X. J.; Li, Y. C.; Lin, Z. H.; Pang, S. P. Energetic Salts Based on an Oxygen-containing Cation: 2,4-Diamino-1,3,5-triazine-6-one. Chem. – Asian J. 2014, 9: 479-486.
  • [16] Chavez, D. E.; Hiskey, M. A.; Gilardi, R. D. Novel High-nitrogen Materials Based on Nitroguanyl-substituted Tetrazines. Org. Let. 2004, 6: 2889-2891.
  • [17] Fu, Z.; He, C.; Chen, F. X. Synthesis and Characteristics of a Novel, High-nitrogen, Heat-resistant, Insensitive Material (NOG2Tz). J. Mater. Chem. 2011, 22: 60-63.
  • [18] Agrawal, J. P. Recent Trends in High-energy Materials. Prog. Energ. & Comb. Sci. 1998, 24: 1-30.
  • [19] Qi, C.; Li, S. H.; Li, Y. C.; Wang, Y.; Zhao, X. X.; Pang, S. P. Synthesis and Promising Properties of a New Family of High-nitrogen Compounds: Polyazidoand Polyamino-substituted N,N′-Azo-1,2,4-triazoles. Chem. - Eur. J. 2012, 18: 16562-16570.
  • [20] Klapötke, T. M.; Sabaté, C. M. Bistetrazoles: Nitrogen-rich, High-performing, Insensitive Energetic Compounds. Chem. Mater. 2008, 20: 3629-3637.
  • [21] Joo, Y. H.; Shreeve, J. M. High-density Energetic Mono- or Bis(oxy)-5-nitroiminotetrazoles. Angew. Chem. Int. Ed. 2010, 49: 7320-7323.
  • [22] Klapötke, T. M.; Mayer, P.; Schulz, A.; Weigand, J. J. 1,5-Diamino-4-methyltetrazolium Dinitramide. J. Am. Chem. Soc. 2005, 127: 2032-2033.
  • [23] Fisher, G.; Holl, G.; Klapötke, T. M.; Weigand, J. J. A Study on the Thermal Decomposition Behaviour of Derivatives of 1,5-Diamino-1H-tetrazole (DAT): a New Family of Energetic Heterocyclic-based Salts. Thermochim. Acta 2005, 437: 168-178.
  • [24] Klapötke, T. M.; Martin, F.; Mayr, N.; Stierstorfer, J. Synthesis and Characterization of 3,5-Diamino-1,2,4-triazolium Dinitramide. Z. Anorg. Allg. Chem. 2010, 636: 2555-2564.
  • [25] Drake, G. W.; Hawkins, T. W.; Boatz, J.; Hall, L.; Vij, A. Experimental and Theoretical Study of 1,5‐Diamino‐4‐H‐1,2,3,4‐Tetrazolium Perchlorate. Propellants Explos. Pyrotech. 2005, 30: 156-163.
  • [26] Joo, Y. H.; Twamley, B.; Garg, S. Energetic Nitrogen-rich Derivatives of 1,5-Diaminotetrazole. Angew. Chem. 2008, 120: 6332-6335.
  • [27] Drake, G. W.; Hawkins, T. W.; Hall, L. A.; Boatz, J. A.; Br, A. J. Structural and Theoretical Investigations of 3,4,5‐Triamino‐1,2,4‐triazolium Salts. Propellants Explos. Pyrotech. 2005, 30: 329-337.
  • [28] Konovalova, I. S.; Shishkina, S. V.; Paponov, B. V.; Shishkin, O. V. Analysis of the Crystal Structure of Two Polymorphic Modifications of 3,4-Diamino-1,2,4-triazole Based on the Energy of the Intermolecular Interactions. CrystEngComm 2010, 12: 909-916.
  • [29] Joo, Y. H.; Twamley, B.; Shreeve, J. M. Carbonyl and Oxalyl Bridged Bis(1,5-diaminotetrazole)-based Energetic Salts. Chem. - Eur. J. 2009, 15: 9097-9104.
  • [30] Wu, J.; Zhang, J.; Yin, X.; Cheng, Z. Y.; Xu, C. 3,4-Diamino-1,2,4-triazolebased Energetic Salts: Synthesis, Characterization, and Energetic Properties. New J. Chem. 2015, 39: 5265-5271.
  • [31] Zhao, X. X.; Li, S. H.; Wang, Y.; Li, Y. C.; Zhao, F. Q.; Pang, S. P. Design and Synthesis of Energetic Materials towards High Density and Positive Oxygen Balance by N-Dinitromethyl Functionalization of Nitroazoles. J. Mater. Chem. A 2016, 4: 5495-5504.
  • [32] Wu, J. T.; Zhang, J. G.; Yin, X.; Wu, L. Energetic Salts Based on 3-Hydrazino-4-amino-1,2,4-triazole (HATr): Synthesis and Properties. New J. Chem. 2016, 40: 5414-5419.
  • [33] Takimoto, H. H.; Denault, G. C.; Hotta, S. Syntheses and Reactions of 5-Alkyl-4-amino-3-hydrazino-s-triazoles. J. Org. Chem. 1965, 30: 711-713.
  • [34] Cardillo, P.; Dellavedova, M.; Gigante, L.; Lunghi, A.; Pasturenzi, C.; Salatelli, E.; Zanirato, P. Synthesis, Spectroscopic and Thermal Characterization of Azido-1,2,4-triazoles: a Class of Heteroarenes with a High Nitrogen Content. Eur. J. Org. Chem. 2012, 2012: 1195-1201.
  • [35] Picard, J. P.; Satriana, D. R.; Masuelli, F. Process for Preparation of Triaminoguanidine and its Salts. Patent US 3813439, 1974.
  • [36] Kaiser, D. W.; Peters, G. A. Method of Preparing Triaminoguanidine Hydrochloride. Patent US 2721218, 1955.
  • [37] Wagaman, K. L.; Clark, C. F.; Henderson, L. D. Method of Producing Triaminoguanidine Nitrate. Patent US 3950421, 1991.
  • [38] Schmidt, M. W.; Gordon, M. S.; Boatz, J. A. Triazolium-based Energetic Ionic Liquids. J. Phys. Chem. A 2005, 109: 7285-95.
  • [39] Xue, H.; Arritt, S. W.; Twamley, B.; Shreeve, J. M. Energetic Salts from N-Aminoazoles. Inorg. Chem. 2004, 43: 7972-7977.
  • [40] Klapötke, T. M.; Sabaté, C. M.; Stierstorfer, J. Hydrogen-bonding Stabilization in Energetic Perchlorate Salts: 5-Amino-1H-tetrazolium Perchlorate and its Adduct with 5-Amino-1H–tetrazole. Z. Anorg. Allg. Chem. 2008, 634: 1867-1874.
  • [41] Teipel, U. Energtic Materials. Wiley-VCH: Weinheim, Germany 2005; ISBN 978-3-527-30240-6.
Uwagi
Opracowanie rekordu w ramach umowy 509/P-DUN/2018 ze środków MNiSW przeznaczonych na działalność upowszechniającą naukę (2019).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-cd9d0324-2fe7-44f5-b070-76335f2e3aa8
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