Abstract
Two energetic salts, DPHT DNS H2O(1) and DHT 2DNS 2H2O(2)[DPHT=3-(3,5-dimethyl-1H-pyrazol-1-yl)-6-hydrazinyl-1,2,4,5-tetrazine; DHT=3,6-dihydrazinyl-1,2,4,5-tetrazine], were synthesized from S-tetrazine with 3,5-dinitrosalicylic acid(DNS). Compounds 1 and 2 were structurally characterized by elemental analysis, infra-red spectroscopy, and single-crystal X-ray diffraction. The thermal behavior of the title compounds was studied by differential scanning calorimetry(DSC) and thermogravimetry(TG). The non-isothermal decomposition kinetics of compound 2 were investigated. The self-accelerating decomposition temperature, thermal ignition temperature, and critical temperatures of thermal explosion were obtained to evaluate the thermal safety of compound 2. The results show compounds 1 and 2 decompose at 150.8 and 179.2 °C, respectively. The TSADT and Tb of compound 2 are higher than those of DHT, which indicates compound 2 is a potential candidate for energetic materials that have good thermal stability.
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Chavez D. E., Hiskey M. A., Gilardi R. D., Org. Lett., 2004, 6(17), 2889
Chavez D. E., Tappan B. C., Hiskey M. A., Son S. F., Harry H., Montoya D., Hagelberg S., Propell. Explos. Pyrot., 2005, 30(6), 412
Huynh M. H. V., Hiskey M. A., Chavez D. E., Naud D. L., Gilardi R. D., J. Am. Chem. Soc., 2005, 127(36), 12537
Chavez D. E., Parrish D. A., J. Heterocyclic. Chem., 2009, 46(1), 88
Chavez D. E., Hanson S. K., Veauthier J. M., Parrish D. A., Angew. Chem. Int. Ed., 2013, 52(27), 6876
Breiner M. M., Chavez D. E., Myers T. W., Gilardi R. D., Synlett., 2015, 26(4), 557
Piercey D. G., Chavez D. E., Heimsch S., Kirst C., Klapötke T. M., Stierstorfer J., Propell. Explos. Pyrot., 2015, 40(4), 491
Yin P., Shreeve J. M., Angew. Chem. Int. Ed., 2015, 54(48), 14721
Joo Y. H., Shreeve J. M., J. Am. Chem. Soc., 2010, 132(42), 15081
Chavez D. E., Parrish D., Preston D. N., Mares I. W., Propell. Explos. Pyrot., 2012, 37(6), 647
Zhang H. H., Jia S. Y., Wang B. Z., Wang X. J., Zhou C., Lian W. P., Li J. Z., Chinese J. Expl. Propell., 2014, 37(2), 23
** X. H., Hu B. C., Liu Z. L., Lv C. X., Chinese J. Expl. Propell., 2014, 37(2), 18
Wang R. H., Xu H. Y., Guo Y., Sa R. J., Shreeve J. M., J. Am. Chem. Soc., 2010, 132(34), 11904
Thottempudi V., Shreeve J. M., J. Am. Chem. Soc., 2011, 133(49), 19982
Marcus H. J., Tetrazine Compounds, US3244702, 1966
Talawar M. B., Sivabalan R. Senthilkumar N., Prabhu G., Asthana S. N., J. Hazard. Mater., 2004, 113(1), 11
Hu Y., Ma H. X., Li J. F., Gao R., Song J. R., B. Korean Chem. Soc., 2010, 31(10), 2897
Feng J. L., Zhang J. G., Wang K., Zhang T. L., Chem. J. Chinese Universities, 2011, 32(7), 1519
Xu K. Z., Zhao F. Q., Ren Y. H., Ma H. X., Song J. R., Hu R. Z., Acta Phys-Chim. Sin., 2009, 25(2), 309
Chavez D. E., Hiskey M. A., J. Energ. Mater., 1999, 17(4), 357
Oxley J. C., Smith J. L., Chen H., Thermochim. Acta, 2002, 384(1), 91
Zhang J. G., Yin X., Wu J. T., Sun M., Feng J. L., Zhang T. L., Zhou Z. N. T., Chinese J. Inorg. Chem., 2013, 29(12), 2587
Zhang H., Zhao F. Q., Yi J. H., Zhang X. H., Hu R. Z., Xu S. Y., Chinese J. Inorg. Chem., 2009, 25(5), 869
Zhao F. Q., Zhang H., An T., Zhang X. H., Gao H. X., Song X. D., Chinese J. Energ. Mater., 2014, 22(5), 635
Liu X. Y., Su Z. Y., Ji W. X., Chen S. P., Wei Q., **e G., Yang X. W., Gao S. L., J. Phys. Chem. C, 2014, 118(41), 23487
Ma H. X., Yan B., Li Z. N., Guan Y. L., Song J. R., Xu K. Z., Hu R. Z., J. Hazard. Mater., 2009, 169(1–3), 1068
Chavez D. E., Hiskey M. A., J. Heterocyclic. Chem., 1998, 35(6), 1329
Sheldrick G. M., SHELXS 97, Program for Crystal Structure Solution, University of Göttingen, Göttingen, 1997
Dolomanov O. V., Blake A. J., Champness N. R., Schröder M., J. Appl. Crystallogr., 2003, 36(5), 1283
Kissinger H. E., Anal. Chem., 1957, 29(11), 1702
Ozawa T. B., Chem. Soc. Jpn., 1965, 38(11), 1881
Ma H. X., Yan B., Li Z. N., Song J. R., Hu R. Z., J. Therm. Anal. Calorim., 2009, 95(2), 437
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Supported by the National Natural Science Foundation of China(Nos.21673179, 21504067) and the National Students’ Innovation and Entrepreneurship Training Program, China(No.201710697038).
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Crystal Structures, Thermal Behavior Analysis and Thermal Safety of Two Energetic Salts of Hydrazinyl-1,2,4,5-tetrazine with 3,5-Dinitrosalicylic Acid
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Chen, X., Zeng, T., Zhang, C. et al. Crystal Structures, Thermal Behavior Analysis and Thermal Safety of Two Energetic Salts of Hydrazinyl-1,2,4,5-tetrazine with 3,5-Dinitrosalicylic Acid. Chem. Res. Chin. Univ. 34, 959–964 (2018). https://doi.org/10.1007/s40242-018-8169-z
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DOI: https://doi.org/10.1007/s40242-018-8169-z