Synthesis and Thermal Properties of Three Energetic Ion Salts of 3,6-Bis[(1H-1,2,3,4-t etrazol-5-yl)-amino]-1,2,4,5-t etrazine

doi:10.1007/s40242-019-8326-z

Chemical Research in Chinese Universities ›› 2019, Vol. 35 ›› Issue (3): 403-409.doi: 10.1007/s40242-019-8326-z

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Synthesis and Thermal Properties of Three Energetic Ion Salts of 3,6-Bis[(1H-1,2,3,4-t etrazol-5-yl)-amino]-1,2,4,5-t etrazine

ZHOU Jie¹, WU Shaojie¹, ZHANG Wenhui¹, LIU Qing¹, YANG Bin¹, REN Yinghui¹, MA Haixia¹, ZHAO Fengqi², HU Rongzu²

1. Department of Chemical Engineering, Northwest University, Xi'an 710069, P. R. China;
2. Xi'an Modern Chemistry Research Institute, Xi'an 710065, P. R. China

Received:2018-10-08 Revised:2018-11-09 Online:2019-06-01 Published:2019-03-27
Contact: REN Yinghui E-mail:renyinghui_ren@163.com
Supported by:
Supported by the National Natural Science Foundation of China(No.21673179), the Key-point Natural Science Foundation of Shaanxi Province, China(No.2016JZ003) and the Graduate Innovation and Creativity Funds of Northwest University, China (No.YZZ17137).

Abstract

Abstract: Three energetic ion salts of 3,6-bis[(1H-1,2,3,4-tetrazol-5-yl)-amino]-1,2,4,5-tetrazine(BTATz), namely, methylamine salt(compound 1), ethylenediamine salt(compound 2), and diethylamine salt(compound 3), were synthesized and characterized by elemental analysis, Fourier transform infrared spectrometry, ¹H NMR spectroscopy, and ¹³C NMR spectroscopy. The crystal structure of compound 1 was determined by single-crystal X-ray crystallography, and structural analysis revealed that it belonged to the monoclinic system with P2₁/c space group. In addition, the thermal behavior of the three compounds was studied by differential scanning calorimetry and thermogravimetry techniques. The thermal decomposition peak temperatures of the compounds were 574.89, 545.60, and 606.72 K, indicating that the three ion salts exhibited good thermal stability. The kinetic mechanism equations of the main decomposition process and the entropy of activation(ΔS^≠), enthalpy of activation(ΔH^≠), and Gibbs free energy of activation(ΔG^≠) of the three compounds were also obtained. Moreover, the thermal safety of the compounds was evaluated by the values of the self-accelerated decomposition temperature(T_SADT), thermal ignition temperature(T_TIT), and critical temperature of thermal explosion(T_b). The results showed that all the compounds demonstrated good thermal safety, and the thermal safety of compound 3 was better than that of the others.

Key words: 3,6-Bis[(1H-1,2,3,4-tetrazol-5-yl)-amino]-1,2,4,5-tetrazine, Ionic salt, Thermal behavior, Thermal safety

ZHOU Jie, WU Shaojie, ZHANG Wenhui, LIU Qing, YANG Bin, REN Yinghui, MA Haixia, ZHAO Fengqi, HU Rongzu. Synthesis and Thermal Properties of Three Energetic Ion Salts of 3,6-Bis[(1H-1,2,3,4-t etrazol-5-yl)-amino]-1,2,4,5-t etrazine[J]. Chemical Research in Chinese Universities, 2019, 35(3): 403-409.

References 25

[1]	Talawar M. B., Sivabalan R., Mukundan T., Muthurajanet H., Sikder A. K., Gandhe B. R., Subhananda Rao A., J. Hazard. Mater., 2009, 161, 589
[2]	Zhang J. H., Zhang Q. H., Thao T. V., Parrish D. A., Shreeve J. M., J. Am. Chem. Soc., 2015, 137, 1697
[3]	Joo Y. H., Jean'ne M. S., J. Am. Chem. Soc., 2010, 132, 15081
[4]	Liu H. X., Wei Y. Y., Tetrahedron Letters, 2013, 54, 4645
[5]	Roman V. T., Philip P., Maija M. K., J. Phy. Chem., 2015, 119, 8512
[6]	Han Z. Y., Yao Q., Zhang Y. H., Du Z. M., Li F., J. Therm. Anal. Calorium., 2015, 119, 461
[7]	Veauthier J. M., Chavez D. E., Tappan B. C., Parrish D. A., J. Energ. Mater., 2010, 28(3), 229
[8]	Fischer G., Holl G., Klapotke T. M., Weigand J. J., Therm. Acta, 2005, 437, 168
[9]	Han Z. Y., Yao Q., Zhang Y. H., Du Z. M., Li F., J. Therm. Anal. Calor., 2015, 121, 951
[10]	Chavez D. E., Hicky M. A., Naud D., Propell. Explos. Pyrot., 2004, 29(4), 209
[11]	Hickey M. A., Chavez D. E., Naud D., 3,6-Bis(1H-1,2,3,4-tetrazol-5- ylamino)-1,2,4,5-tetrazine or Salt Thereof, US 6657059P, 2003
[12]	Zhang W. H., Liu Q., Ren Y. H., Yang B., Zhang X. B., Zhang C., Ma H. X., Zhao F. Q., Hu R. Z., Chem. Res. Chinese Universities, 2018, 34(2), 254
[13]	Zhang X. B., Ren Y. H., Li W., Zhao F. Q., Wang B. Z., Song J. R., Chem. Res. Chinese Universities, 2013, 29(4), 627
[14]	Liu Q., Yang B., Yang J., Ren Y. H., Zhang X. B., Ma H. X., Xu K. Z., Zhao F. Q., Hu R. Z., J. Coor. Chem., 2017, 70, 2249
[15]	Wang Y. L., Zhao F. Q., Ji Y. P., Yi J. H., Wang W., Xu S. Y., An T., Pei Q., Chem. Res. Chinese Universities, 2014, 30(3), 468
[16]	Liu Q., Chen X., Cao W. L., Yang J., Zhang W. H., Ren Y. H., Zhang X. B., Ma H. X., Zhao F. Q., Hu R. Z., Acta Cryst. C, 2017, 73, 911
[17]	Li W., Ren Y. H., Zhao F. Q., Zhang X. B., Ma H. X., Xu K. Z., Wang B. Z., J. Functional Mater., 2003, 44(22), 3326
[18]	Liu Q., Yang J., Ren Y. H., Ma H. X., Xu K. Z., Zhang C., Zhao F. Q., Hu R. Z., Chin. J. Energy Mater., 2017, 25, 570
[19]	Wang B. Z., Lai W. P., Liu Q., Lian P., Xue Y. Q., Chin. J. Org. Chem., 2008, 28(3), 422
[20]	Zhang X. B., Study of High Nitrogen Tetrazine BTATz Metal Salts/Complexes, Northwest University, Xi'an, 2013
[21]	Sheldrick, G. M., SHELXL-97:Program for the Refinement of Crystal Structures, University of Göttingen, Göttingen, 1997
[22]	Kissinger H. E., Anal. Chem., 1957, 29,1702
[23]	Ozawa T. B., Bull. Chem. Soc. Japan, 1965, 38(11), 1881
[24]	Hu R, Z., Gao S. L., Zhao F. Q., Thermal Analysis Kinetics, 2nd Ed., Science Press, Beijing, 2008
[25]	Zhao F. Q., Hu R. Z., Gao H. X., Ma H. X., New Developments in Hazardous Materials Research, Nova Science Publishers Inc., New York, 2006, 4

Synthesis and Thermal Properties of Three Energetic Ion Salts of 3,6-Bis[(1H-1,2,3,4-t etrazol-5-yl)-amino]-1,2,4,5-t etrazine

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