Synthesis and Thermodynamic Properties of M₂L[M=Li, Na; L=3,6-Bis(1H-1,2,3,4-tetrazol-5-yl-amino)-1,2,4,5-tetrazine]

Abstract

Two novel energetic alkalic metal salts of 3,6-bis(1H-1,2,3,4-tetrazol-5-yl-amino)-1,2,4,5-tetrazine (BTATz), Li₂(BTATz)·6H₂O(compound 1) and Na₂(BTATz)·2H₂O(compound 2), have been synthesized by the reac-tion of BTATz with lithium hydroxide or sodium hydroxide in dimethylsulfoxide(DMSO) solution, respectively, and their structures were characterized by means of elemental analysis and Fourier transform infrared spectrometry(FTIR). Moreover, the single-crystal structure of compound 1 was determined by single crystal X-ray diffraction. It crystal-lizes in the monoclinic space group P1/c. Furthermore, their thermal decomposition behaviors were investigated by means of differential scanning calorimetry(DSC) and thermogravimetry-differential thermal gravimetry(TG-DTG). The results show that the exothermic decomposition peak temperatures for compounds 1 and 2 were 642.65 and 644.46 K, respectively, and the kinetic equations of the main exothermic decomposition were also derived from non-isothermal method. Additionally, the thermal safety of the two compounds was evaluated by calculating self-accelerating decomposition temperature(T _SADT) and critical temperature of thermal explosion(T _b). The results(the TSADT and T _b values are 605.43 and 635.69 K for compound 1; 607.38 and 638.96 K for compound 2) reveal that the two compounds exhibit better thermal safety than BTATz.

Keywords

3,6-Bis(1H-1,2,3,4-tetrazol-5-yl-amino)-1,2,4,5-tetrazine(BTATz) / Alkalic metal salt / Thermal behavior / Thermodynamic property / Thermal safety

References

[1] Dippold A., Klapotke T. M., Martin F. A. Z. Anorg. Allg. Chem., 2011, 637: 1181.

[2] Huang H. F., Zhou Z. M., Liang L. X., Song J. R., Wang K., Cao D., Bian C. M., Sun W. W., Xue M. Z. Anorg. Allg. Chem., 2012, 638: 392.

[3] Myers T. W., Bjorgaard J. A., Brown K. E., Chavez D. E., Hanson S. K., Scharff R. J., Tretiak S., Veautheir J. M. J. Am. Chem. Soc., 2016, 138: 4685.

[4] Ren Y. H., Li W., Zhang X. B., Zhao F. Q., Yi J. H., Ma H. X., Xu K. Z., Song J. R. Chin. J. Appl. Chem., 2013, 30: 1036.

[5] Zhang J. G., Liang Y. H., Feng J. L., Wang K., Zhang T. L., Zhang Z. N., Yang L. Z. Anorg. Allg. Chem., 2012, 638: 1212.

[6] Yi J. H., Zhao F. Q., Ren Y. H., Wang B. Z., Zhou C., Ren X. N., Xu S. Y., Hao H. X., Hu R. Z. J. Therm. Anal. Calorium, 2011, 104: 1029.

[7] Wang Y. L., Zhao F. Q., Xu K. Z., Ji Y. P., Yi J. H., Chen B., An T. Inorg. Chim. Acta, 2013, 405: 505.

[8] Hickey M. A., Chavez D. E., Naud D. Preparation of 3,3′-Azobis(6-amino-1,2,4,5-tetrazine), 2002.

[9] 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, 2003.

[10] Yue S. T., Yang S. Q. Chin. J. Energy. Mater., 2004, 12: 155.

[11] Wang B. Z., Lai W. P., Liu Q., Lian P., Xue Y. Q. Chin. J. Org. Chem., 2008, 28: 422.

[12] Saikia A., Sivabalan R., Polke B. G., Gore G. M., Singh A., Rao A. S., Sikder A. K. J. Hazard. Mater., 2009, 170: 306.

[13] Zhang X. G., Zhu H., Yang S. Q., Zhang W., Zhao F. Q., Liu Z. R., Pan Q. Chin J. Prop. Technol., 2007, 28: 322.

[14] Li N., Zhao F. Q., Luo Y., Mao H. C., Xiao L. B., Gao H. X., An T., Hu R. Z. J. Solution Chem., 2014, 43: 1250.

[15] Yi J. H., Zhao F. Q., Wang B. Z., An T., Wang Y., Gao H. X. J. Therm. Anal. Calor, 2014, 115: 1227.

[16] Naud D., Hiskey M. A. Proc. Combust. Inst., 2000, 28: 919.

[17] Hickey M. A., Chavez D. E., Naud D. Low-smoke Pyrotechnic Compositions, US 6312537P, 2001.

[18] Li S. W., Zhao F. Q., Yuan C., Luo Y., Gao Y. Chin. J. Solid Rocket Tech., 2002, 25: 36.

[19] Hickey M. A., Chavez D. E., Naud D. Propellant Containing 3,6-Bis(1H-1,2,3,4-tetrazol-5-yl-amino)-1,2,4,5-tetrazine or Salts Thereof, 2002.

[20] Wu B., Yang H. W., Tang Y. X., Wang Z. X., Lu C. X., Cheng G. B. J. Energ. Mater., 2015, 33: 180.

[21] Ma C., Huang J., Ma H. X., Xu K. Z., Lv X. Q., Song J. R., Zhao N. N., He J. Y., Zhao Y. S. J. Mol. Struct., 2013, 1036: 521.

[22] Zhou T. H., Wang X. H., Xu K. Z., Song J. R., Zhao F. Q. Inorg. Chim. Acta, 2016, 453: 149.

[23] Guo J. J., Huang J., Song J. R., Miao K. H., Cao W. L. Chem. Res. Chinese Universities, 2016, 32(5): 812.

[24] 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.

[25] Wang S. W., Wu B. D., Yang L., Zhang T. L., Zhou Z. N., Zhang J. G. Chem. Res. Chinese Universities, 2012, 28(4): 585.

[26] Wang Y. L., Zhao F. Q., Ji Y. P., Pan Q., Yi J. H., An T., Wang W., Yu T., Lu X. M. J. Anal. Appl. Pyrol., 2012, 98: 231.

[27] Jin X. H., Hu B. C., Liu Z. L. J. Braz. Chem. Soc., 2015, 26: 124.

[28] Li W., Ren Y. H., Zhao P. Q., Zhang X. B., Ma H. X., Yu K. Z., Wang B. Z. J. Functional Mater., 2013, 22: 3326.

[29] Yi J. H., Zhao F. Q., Wang B. Z., Liu Q., Zhou C., Hu R. Z., Xu S. Y., Zhang L. Y., Ren X. N. J. Hazard. Mater., 2010, 181: 432.

[30] 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.

[31] Zhang X. B., Ren Y. H., Li W., Zhao F. Q., Yi J. H., Wang B. Z., Song J. R. J. Coord. Chem., 2013, 66: 2051.

[32] 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. Coord. Chem., 2017, 70: 2249.

[33] Zhang X. B. Study of High Nitrogen TetrazineBTATz Metal Salts/complexes, 2013, Xi’an: Northwest Universities.

[34] Hu Y. Theoretical Study on the Interaction Between s-Tetrazine Compounds, 2010, Xi’an: Northwest Universities.

[35] Dolomanov O. V., Bourhis L. J., Gildea R. J., Howard J. A., Pusch-mann H. J. Appl. Cryst., 2009, 42: 339.

[36] Sheldrick G. M. Acta Cryst., 2015, 71: 3.

[37] Zhao F. Q., Hu R. Z., Gao H. X., Ma H. X., New Development in hazardous Materials Research, Nova Science Publishers Inc., New York, 2006, 4

[38] Ren Y. H., Li D., Yi J. H., Zhao F. Q., Ma H. X., Xu K. Z., Song J. R. Bull. Korean Chem. Soc., 2010, 31: 1988.

[39] Ma H. X., Song J. R., Zhao F. Q., Hu R. Z., Xiao H. M. J. Chem. Phys., 2007, 111: 8642.

[40] Xu K. Z., Song J. R., Zhao F. Q., Chao Z. H., Ma H. X., Hu R. Z., Gao H. X., Huang J. Acta Chim. Sinica, 2007, 65: 2827.