Identyfikatory
Warianty tytułu
Języki publikacji
Abstrakty
Synthesis of materials with acceptable performance and low sensitivity to physical stimuli is one of the overall goals of energetic materials. The creation of networks of hydrogen bonds affords good stability to the trigger bonds. In this respect azole-based ionic high-energy materials (especially aminotetrazoles) and other nitrogen-rich compounds have strong hydrogen bonds. Significant stability, insensitivity to a physical stimulus and also good performance are thus created. In this study salts derived from N-(1-carboxymethyl-1H-tetrazole-5-yl)-hydrazinium chloride were synthesized. Anion exchange of the chlorine with nitrate, 5-aminotetrazolate, (5-amino-tetrazole-1-yl)-acetate and (5-nitriminotetrazole-1-yl)-acetate was performed, with precipitation of AgCl. All of the products were characterized using 1H NMR, 13C NMR, FTIR spectroscopy, differential scanning calorimetry (DSC), impact sensitivity and UV-Vis spectroscopy. Among the advantages of this study are the use of methods and available equipment and low-risk solvents during the reaction and the formation of minimum by-products.
Rocznik
Tom
Strony
420--434
Opis fizyczny
Bibliogr. 32 poz., rys., tab.
Twórcy
autor
- Department of Chemistry and Chemical Engineering, Malek Ashtar University of Technology 16765-3454 Lavizan, Tehran, Iran
autor
- Department of Chemistry and Chemical Engineering, Malek Ashtar University of Technology 16765-3454 Lavizan, Tehran, Iran
Bibliografia
- [1] Li, Y. C.; Qi, C.; Li, S. H.; Zhang, H. J.; Sun, C. H.; Yu, Y. Z.; Pang, S. P. 1,1′-Azobis-1,2,3-triazole: A High-nitrogen Compound with Stable N8 Structure and Photochromism. J. Am. Chem. Soc. 2010, 132(35): 12172-12173.
- [2] Thottempudi, V.; Forohor, F.; Parrish, D. A.; Shreeve, J. M. Tris-(triazolo)benzene and Its Derivative: High-density Energetic Materials. Angew. Chem. Int. Ed. 2012, 51(39): 1-6.
- [3] Fu, Z.; Wang, Y.; Yang, L.; Su, R.; Chen, J.; Nie, F.; Huang, J.; Chen, F. Synthesis and Characteristics of Novel, High-nitrogen 1,2,4-Oxadiazoles. RSC Adv. 2014, 4: 11859-11861.
- [4] Thottempudi, V.; Shreeve, J. M. Synthesis and Promising Properties of a New Family of High-density Energetic Salts of 5-Nitro-3-trinitromethyl-1H-1,2,4-triazole and 5,5’-Bis(trinitromethyl)-3,3’-azo-1H-1,2,4-triazole. J. Am. Chem. Soc. 2011, 133(49): 19982-19992.
- [5] Liu, W.; Li, S.; Li, Y.; Yang, Y.; Yua, Y.; Pang, S. Nitrogen-rich Salts Based on Polyamino Substituted N,N-azo-1,2,4-triazole: a New Family of High Performance Energetic Materials. J. Mater. Chem. 2014, 2(38): 15978-15986.
- [6] Thottempudi, V.; Gao, H.; Shreeve, J. M. Trinitromethyl-substituted 5-Nitro- or 3-Azo-1,2,4-triazole: Synthesis, Characterization, and Energetic Properties. J. Am. Chem. Soc. 2011, 133(16): 6464-6471.
- [7] Wu, J. T.; Zhang, J. G.; Yin, X.; Cheng, B. Z. Y.; Xu, C. X. 3,4-Diamino-1,2,4-triazole Based Energetic Salts: Synthesis, Characterization, and Energetic Properties. New J. Chem. 2015, 39(7): 5265-5271.
- [8] 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(23): 6776-6785.
- [9] Tang, Y.; Yang, H.; Wu, B.; Ju, X.; Lu, C.; Cheng, G. Synthesis and Characterization of a Stable, Catenated N11 Energetic Salt. Angew. Chem. Int. Ed. 2013, 52(18): 4975-4977.
- [10] Moulin, A.; Bibian, M.; Blayo, A. L.; Habnouni, S. E.; Martinez, J.; Fehrentz, J. A. Synthesis of 3,4,5-Trisubstituted-1,2,4-triazoles. Chem. Rev. 2010, 110(4): 1809-1827.
- [11] Frija, L. M. T.; Ismael, A.; Cristiano, M. L. S. Photochemical Transformations of Tetrazole Derivatives: Applications in Organic Synthesis. Molecules 2010, 15(5): 3757-3774.
- [12] Damse, R. S.; Sikder, A. K. Suitability of Nitrogen-rich Compounds for Gun Propellant Formulations. J. Hazard. Mater. 2009, 166(2-3): 967-971.
- [13] Kizhnyaev, V. N.; Vereshchagin, L. I.; Verkhozina, O. N.; Pokatilov, F. A.; Tsypina, N. N.; Petrova, T. L.; Sukhanov, G. T.; Gareev, G. A.; Smirnov, A. I. Triazole and Tetrazole Containing Energetic Compounds. 34th Int. Annu. Conf. ICT, Karlsruhe 2003, 1-11.
- [14] Galvez-Ruiz, J. C.; Holl, G.; Karaghiosoff, K.; Klapötke, T. M.; Loehnwitz, K.; Mayer, P.; Noth, H.; Polborn, K.; Rohbogner, C. J.; Suter, M.; Weigand, J. J. Derivatives of 1,5-Diamino-1H-tetrazole: a New Family of Energetic Heterocyclicbased Salts. Inorg. Chem. 2005, 44(12): 4237-4253.
- [15] Akiyoshi, M.; Ooba, J.; Ikeda, K.; Nakamura, H. 5-Aminotetrazoles and Silverbased Primary Explosives. Sci. Tech. Adv. Mater. 2003, 64(3): 103-104.
- [16] Delalu, H.; Karaghiosoff, K.; Klapötke, T. M.; Sabate, C. M. 5-Aminotetrazoles and Silver-based Primary Explosives. Cent. Eur. J. Energ. Mater. 2010, 7(3): 197-216.
- [17] Gao, H.; Huang, Y.; Ye, C.; Twamley, B.; Shreeve, J. M. The Synthesis of Di(aminoguanidine) 5-Nitroiminotetrazolate: Some Diprotic or Monoprotic Acids as Precursors of Energetic Salts. Eur. J. Inorg. Chem. 2008, 14(36): 5596-5603.
- [18] Thottempudi, V.; Shreeve, J. M. Synthesis of Trinitromethyl- and Dinitromethyl-Substituted Azoles Using Nitrate Salts in Sulfuric Acid. Synthesis 2012, 44(8):1253-1257.
- [19] Thottempudi, V.; Gao, H.; Shreeve, J. M. Trinitromethyl-substituted 5-Nitro- or 3-Azo-1,2,4-triazoles: Synthesis, Characterization, and Energetic Properties. J. Am. Chem. Soc. 2011, 133(16): 6464-6471.
- [20] Klapötke, T. M.; Stierstorfer, J. Nitration Products of 5-Amino-1H-tetrazole and Methyl-5-amino-1H-tetrazoles – Structures and Properties of Promising Energetic Materials. Helv. Chir. Acta 2007, 90(11): 2132-2150.
- [21] Joo, Y. H.; Gao, H.; Parrish, D. A.; Cho, S. G.; Goh, E. M.; Shreeve, J. M. Energetic Salts Based on Nitroiminotetrazole-containing Acetic Acid. J. Mater. Chem. 2012, 22(13): 6123-6130.
- [22] Swain, P. K.; Singh, H.; Tewari, S. P. J. Energetic Ionic Salts Based on Nitrogenrich Heterocycles: a Prospective Study. J. Mol. Liq. 2010, 151(2-3): 87-96.
- [23] Moulin, A.; Bibian, M.; Blayo, A. L.; Habnouni, S. E.; Martinez, J.; Fehrentz, J. A. Synthesis of 3,4,5-Trisubstituted-1,2,4-triazoles. J. Am. Chem. Soc. 2010, 110(4):1809-1827.
- [24] Frija, L. M. T.; Ismael, A.; Cristiano, M. L. S. Photochemical Transformations of Tetrazole Derivatives: Applications in Organic Synthesis. Molecules 2010, 15(5):3757-3774.
- [25] Habibi, D.; Nasrollahzadeh, M.; Faraji, A. R.; Bayat, Y. Efficient Synthesis of Arylaminotetrazoles in Water. Tetrahedron 2010, 66(21): 3866-3870.
- [26] Zhilin, A. Y.; Ilyushin, M. A.; Tselinskii, I. V.; Kozlov, A. S.; Kuz’mina, N. E. Synthesis and Properties of Tetraamminebis(1-methyl-5-aminotetrazole-N3,N4) cobalt(III) Perchlorate. Russ. J. Appl. Chem. 2002, 75: 1849-1851.
- [27] Li, F.; Cong, X.; Du, Z.; He, C.; Zhao, L.; Meng, L. 1,1’-Diamino-5,5’-azotetrazole: a Nitrogen Rich Compound. New J. Chem. 2012, 36(10): 1953-1956.
- [28] Bocian, W.; Jaiwinski, J.; Koiminski, W.; Stefaniak, L.; Webb, G. A. A Multinuclear NMR Study of Some Mesoionic 1,3-Dimethyltetrazoles, 1- and 2-Methyltetrazoles and Related Compounds. J. Chem. Soc. 1994, 2(6): 1327-1332.
- [29] Brady, L. E. Electron Impact-induced Fragmentation of 5-Aminotetrazole. J. Heterocyclic Chem. 1970, 7(5): 1223-1225.
- [30] Jafari, S. Synthesized Energetic Derivatives of Tetrazole in the Presence of Nano-Catalysts. M.Sc. Thesis, Malek Ashtar University, 2014.
- [31] Einberg, F. Alkylation of 5-Substituted Tetrazoles with a Chlorocarbonyl Compounds. J. Org. Chem. 1970, 35(11): 3978-3980.
- [32] Klapötke, T. M.; Sproll, S. M. Synthesis of Functionalized Tetrazenes as Energetic Compounds. J. Org. Chem. 2009, 74(6): 2460-2466.
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-10215322-f5d6-494a-aa41-4eab6b0ff302