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Thermochemical properties of 2-oxo-1,3,5-trinitro-1,3,5-triazacyclohexane in dimethyl sulfoxide

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Abstract

The dissolution properties of 2-oxo-1,3,5-trinitro-1,3,5-triazacyclohexane (Keto-RDX) in dimethyl sulfoxide (DMSO) were studied by using a RD496-2000 Calvet microcalorimeter at four different temperatures under atmospheric pressure. The heat effects, molar enthalpies (Δ diss H), and differential enthalpies (Δ dif H) of dissolution were determined. Furthermore, the corresponding kinetic equations describing the dissolution processes at the four experimental temperatures are dα/dt = 10−2.43 (1 − α)0.63 (T = 298.15 K), dα/dt = 10−2.41 (1 − α)0.67 (T = 303.15 K), dα/dt = 10−2.40 (1 − α)0.75 (T = 308.15 K), and dα/dt = 10−2.38 (1 − α)0.76 (T = 313.15 K). The determined values of the activation energy E and pre-exponential factor A for the dissolution process are 5.99 kJ mol−1 and 10−1.38 s−1, respectively.

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References

  1. Dagley IJ, Kony M. Properties and impact sensitiveness of cyclic nitroamine explosives containing nitroguanidine groups. J Energ Mater. 1995;13:35–56.

    Article  CAS  Google Scholar 

  2. Luis GL, Paz D, Ciller J. On the use of AM1 and PM3 methods on energetic compounds. Propellants Explos Pyrotech. 1993;18:33–40.

    Article  Google Scholar 

  3. Huang DS, Rindone RP. High energy insensitive cyclic nitramines. USP 4937340. 1991.

  4. Kony M, Dagley IJ, Leslie DR. 14N NMR studies on cyclic nitramines correlations of chemical shifts with nitrogen partial atomic charge and π-orbital overlap. J Org Chem. 1994;59:5623–6.

    Article  CAS  Google Scholar 

  5. Bracuti AJ. Crystal structure of 2-nitroimino-5-nitrohexahydro-1,3,5-triazine. USP 20100326575. 2010.

  6. Metelkina EL. 2-Nitroguanidine derivatives: X. synthesis and nitration of 4-nitriminotetrahydro-1,3,5-oxadiazine and 2-nitriminoohexahydro-1,3,5-triazine and their substituted derivatives. Russian. J Org Chem. 2007;43:1437–40.

    CAS  Google Scholar 

  7. Shokrollahl A, Zali A, Pouretedal HR, Keshavarz MH. Synthesis of Keto-RDX and its characterizations calculation. Chinese. J Energ Mater. 2008;16:44–8.

    Google Scholar 

  8. Sikder N, Bulakh NR, Sikder AK. Synthesis, characterization and thermal studies of 2-oxo-1,3,5-trinitro-1,3,5-triazacyclohexane (Keto-RDX or K-6). J Hazard Mater A. 2003;96:109–19.

    Article  CAS  Google Scholar 

  9. Cliff MD, Dagley IJ, Parker RP, Walker G. Synthesis of 2-nitroimino-5-nitrohexahydro-1,3,5-triazine via chloride-assisted nitrolysis of a tertiary amine. Propellants Explos Pyrotech. 1998;23:179–81.

    Article  CAS  Google Scholar 

  10. Zhou C, Zhou YS, Huo H, Wang BZ, Li JK, Pan Q, Ren XN. Synthesis and thermal behavior for 2-nitrimino-5-nitrohexahydro-1,3,5-triazine. Chin J Explos Propellants. 2012;35:32–5.

    CAS  Google Scholar 

  11. Blas L, Klaumünzer M, Pessina F, Braun S, Spitzer D. Nanostructuring of pure and composite-based K6 formulations with low sensitivities. Propellants Explos Pyrotech. 2015;40:938–44.

    Article  CAS  Google Scholar 

  12. Shokrolahi A, Zali A, Mousaviazar A, Keshavarz MH, Hajhashemi H. Preparation of nano-K-6 (Nano-Keto RDX) and determination of its characterization and thermolysis. J Energ Mater. 2011;29:115–26.

    Article  CAS  Google Scholar 

  13. Marthada VK. The enthalpy of solution of SRM 1655 (KCl) in H2O. J Res Nat Bur Stand. 1980;85:467–8.

    Article  Google Scholar 

  14. Li N, Zhao FQ, XuanCL Gao HX, Xiao LB, Yao EG, Qu WG, Hu RZ. Thermochemical properties of 2,6-diamino-3,5-dinitropyrazine-1-oxide in dimethyl sulfoxide and N-methyl pyrrolidone. J Therm Anal Calorim. 2017;127:2511–6.

    Article  CAS  Google Scholar 

  15. Li N, Zhao FQ, Luo Y, Mo HC, Gao HX, Xiao LB, Yao EG, Hu RZ. Study on curing reaction thermokinetics of azide binder/bispropargyl succinate by microcalorimetry. Propellants Explos Pyrotech. 2015;40(6):808–13.

    Article  CAS  Google Scholar 

  16. Li N, Zhao FQ, Luo Y, Gao HX, Yao EG, Zhou ZM, Xiao LB, Hu RZ, Jiang HY. Dissolution thermokinetics of dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate in dimethyl sulfoxide. J Therm Anal Calorim. 2015;122:1023–7.

    Article  CAS  Google Scholar 

  17. Xiao LB, Luo Y, Zhao FQ, Gao HX, Li N, Chen XL, Wang Y, Hu RZ. Dissolution properties of 4,10-dinitro-2,6,8,12-tetraoxa-4,10-diazaisowutrzitane in N-methyl pyrrolidone. J Therm Anal Calorim. 2016;123:659–63.

    Article  CAS  Google Scholar 

  18. Li N, Zhao FQ, Luo Y, Gao HX, Xiao LB, Hu RZ, Ju RH. Dissolution property of N-guanylurea dinitramide in dimethyl sulfoxide and N-methyl pyrrolidone. J Therm Anal Calorim. 2014;112:26–9.

    Google Scholar 

  19. Hu RZ, Zhao FQ, Gao HX, Song JR. Foundation and application of calorimetry. Beijing: Science Press; 2011.

    Google Scholar 

  20. Xiao LB, Zhao FQ, Luo Y, Li N, Gao HX, Xue YQ, Cui ZX, Hu RZ. Thermal behavior and safety of dihydroxylammonium 5,5′-bistetrazole-1-1′-diolate. J Therm Anal Calorim. 2016;123:653–7.

    Article  CAS  Google Scholar 

  21. Künzel M, Yan QL, Šelešovský J, Zeman S, Matyáš R. Thermal behavior and decomposition kinetics of ETN and its mixtures with PETN and RDX. J Therm Anal Calorim. 2014;115:289–99.

    Article  Google Scholar 

  22. Hu RZ, Gao SL, Zhao FQ, Zhang TL, Zhang JJ. Thermal analysis kinetics. Beijing: Science Press; 2008.

    Google Scholar 

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Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (No. 21573173).

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Authors and Affiliations

  1. Science and Technology on Combustion and Explosion Laboratory, Xi’an Modern Chemistry Research Institute, Xi’an, 710065, China

    Na Li, Feng-Qi Zhao, Chun-Lei Xuan, Ting An, Yan-Jing Yang, Hong-Xu Gao, Li-Bai Xiao & Rong-Zu Hu

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  1. Na Li
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Li, N., Zhao, FQ., Xuan, CL. et al. Thermochemical properties of 2-oxo-1,3,5-trinitro-1,3,5-triazacyclohexane in dimethyl sulfoxide. J Therm Anal Calorim 131, 3047–3052 (2018). https://doi.org/10.1007/s10973-017-6757-7

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