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Application and Development of 3,4-Bis(3-nitrofurazan-4-yl)furoxan (DNTF)

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Abstract

Energetic materials such as furazan and furoxan exhibit superior energy performance due to their high enthalpy of formation and density. Their research as energetic materials has attracted close attention. Among such compounds, DNTF is the most representative and the most efficient material with the advantages of high energy density, high enthalpy of formation, and high nitrogen content, while high mechanical sensitivity and poor thermal stability retard its application. This paper reviews the development of DNTF over recent decades from the points of synthesis, structure, physicochemical properties, and practical applications. Perspectives of DNTF research and development are also considered.

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REFERENCES

  1. Zhou, S., and Wu, W., Chem. Ind. Times, 1997, vol. 11, p. 3.

    CAS  Google Scholar 

  2. Nielsen, A.T., Chafin, A.P., Christian, S.L., Moore, D.W., Nadler, M.P., Nissan, R.A., Vanderah, D.J., Gilardi, R.D., George, C.F., and Flippen-Anderson, J.L., Tetrahedron, 1998, vol. 54, p. 11793. https://doi.org/10.1016/S0040-4020(98)83040-8

    Article  CAS  Google Scholar 

  3. Sikder, A.K., and Sikder, N., J. Hazard. Mater., 2004, vol. 112, p. 1. https://doi.org/10.1016/j.jhazmat.2004.04.003

    Article  CAS  PubMed  Google Scholar 

  4. Wang, Y., Liu, Y., Song, S., Yang, Z., Qi, X., Wang, K., Liu, Y., Zhang, Q., and Tian, Y., Nat. Commun., 2018, vol. 9, p. 2444. https://doi.org/10.1038/s41467-018-04897-z

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Xue, Q., Bi, F., Zhang, J., Zhang, J., Wang, B., and Zhang, S., Chin. J. Org. Chem., 2019, vol. 39, p. 1244. https://doi.org/10.6023/cjoc201811029

    Article  CAS  Google Scholar 

  6. Sheremetev, A.B., J. Heterocycl. Chem., 1995, vol. 32, p. 371. https://doi.org/10.1002/jhet.5570320201

    Article  CAS  Google Scholar 

  7. Wang, J., Li, J., Liang, Q., Huang, Y., and Dong, H., Propellants, Explos., Pyrotech., 2008, vol. 33, p. 347. https://doi.org/10.1002/prep.200800225

    Article  CAS  Google Scholar 

  8. Kazakov, A.I., Dashko, D.V., Nabatova, A.V., Stepanov, A.I., and Lempert, D.B., Combust., Explos. Shock Waves, 2018, vol. 54, p. 147. https://doi.org/10.1134/S001050821802003X

    Article  Google Scholar 

  9. Stepanov, A.I., Dashko, D.V., and Astrat'ev, A.A., Cent. Eur. J. Energ. Mater., 2012, vol. 9, p. 329.

    CAS  Google Scholar 

  10. Hu, H., and Zhang, Z., China Patent 02101092.7, 2002.

  11. Zheng, W., and Wang, J., Chin. J. Energ. Mater., 2006, vol. 6, p. 463.

    Google Scholar 

  12. Sheremetev, A.B., Ivanova, E.A., Spiridonova, N.P., Melnikova, S.F., Tselinsky, I.V., Suponitsky, K.Yu., and Antipin, M.Yu., J. Heterocycl. Chem., 2005, vol. 42, p. 1237. https://doi.org/10.1002/jhet.5570420634

    Article  CAS  Google Scholar 

  13. Sheremetev, A.B., Makhova, N.N., and Friedrichsen, W., Adv. Heterocycl. Chem., Academic Press., 2001, vol. 78, p. 65. https://doi.org/10.1016/S0065-2725(01)78003-8

    Article  CAS  Google Scholar 

  14. Emmons, W.D., J. Am. Chem. Soc., 1954, vol. 76, p. 3468. https://doi.org/10.1021/ja01642a029

    Article  CAS  Google Scholar 

  15. Wang, J., Dong, H., and Huang, Y., China Patent 200410029246.8, 2006.

  16. Wang, J., Zhou, X., Zhang, X., Li, J., and Huang, Y., Chin. J. Energ. Mater., 2011, vol. 19, p. 747.

    Google Scholar 

  17. Wang, J., Li, J., Yang, G., Zhou, X., Ma, Q., Huang, J., and Zhang, L., China Patent 103965131, 2014.

  18. Zhang, J., Zhou, J., Bi, F., and Wang, B., Chin. Chem. Lett., 2020, vol. 31, p. 2375. https://doi.org/10.1016/j.cclet.2020.01.026

    Article  CAS  Google Scholar 

  19. Zhai, L., Bi, F., Luo, Y., Wang, N., Zhang, J., and Wang, B., Sci. Rep., 2019, vol. 9, p. 4321. https://doi.org/10.1038/s41598-019-39723-z

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. Zhou, Y.-S., Zhang, Z.-Z., Li, J.-K., Guan, X.-R., Huang, X.-P., and Zhou, C., Chin. J. Explos. Propellants, 2005, vol. 28, p. 43. https://doi.org/10.14077/j.issn.1007-7812.2005.02.013

    Article  CAS  Google Scholar 

  21. Olofson, R.A., and Michelman, J.S., J. Org. Chem., 1965, vol. 30, p. 1854. https://doi.org/10.1021/jo01017a034

    Article  CAS  Google Scholar 

  22. Ma, H.-X., Song, J.-R., **ao, H.-M., Hu, R.-Z., and Zhao, F.-Q., Chin. J. Explos. Propellants, 2006, vol. 3, p. 43. https://doi.org/10.14077/j.issn.1007-7812.2006.03.013

    Article  Google Scholar 

  23. Kotomin, A.A., Kozlov, A.S., and Dushenok, S.A., Russ. J. Phys. Chem. B+, 2007, vol. 1, p. 573. https://doi.org/10.1134/S1990793107060103

    Article  Google Scholar 

  24. Kim, T.K., Choe, J.H., Lee, B.W., and Chung, K.-H., Bull. Korean Chem. Soc., 2012, vol. 33, p. 2765. https://doi.org/10.5012/bkcs.2012.33.8.2765

    Article  CAS  Google Scholar 

  25. Zhao, F.Q., Qu, W.G., Gao, H.X., and Luo, Y., Sci. Sin.: Chim., 2014, vol. 44, p. 953. https://doi.org/10.1360/N032014-00017

    Article  CAS  Google Scholar 

  26. Zhao, F.-Q., Chen, P., Hu, R.-Z., Luo, Y., Zhang, Z.-Z., Zhou, Y.-S., Yang, X.-W., Gao, Y., Gao, S.-L., and Shi, Q.-Z., J. Hazard. Mater., 2004, vol. 113, p. 67. https://doi.org/10.1016/j.jhazmat.2004.07.009

    Article  CAS  Google Scholar 

  27. Sinditskii, V.P., Burzhava, A.V., Sheremetev, A.B., and Aleksandrova, N.S., Propellants, Explos., Pyrotech., 2012, vol. 37, p. 575. https://doi.org/10.1002/prep.201100095

    Article  CAS  Google Scholar 

  28. Gao, H.-X., Zhao, F.-Q., Hu, R.-Z., Xu, K.-Z., Zhang, H., Wang, P., Du, Z.-M., Xu, S.-Y., Yi, J.-H., Ma, H.-X., Chang, C.-R., and Song, J.-R., Chem. J. Chin. Univ., 2008, vol. 29, p. 981.

    CAS  Google Scholar 

  29. Zhang, G., **, S., Li, L., Li, Y., Li, Z., Wang, D., Zhang, B., **g, B., and Shu, Q., J. Therm. Anal. Calorim., 2016, vol. 126, p. 1185. https://doi.org/10.1007/s10973-016-5666-5

    Article  CAS  Google Scholar 

  30. Tsyshevsky, R.V. and Kuklja, M.M., Molecules, 2013, vol. 18, p. 8500. https://doi.org/10.3390/molecules18078500

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  31. Tsyshevsky, R., Pagoria, P., Zhang, M., Racoveanu, A., DeHope, A., Parrish, D., and Kuklja, M.M., J. Phys. Chem. C, 2015, vol. 119, p. 3509. https://doi.org/10.1021/jp5118008

    Article  CAS  Google Scholar 

  32. Tsyshevsky, R.V., Sharia, O., and Kuklja, M.M., Molecules, 2016, vol. 21, p. 236. https://doi.org/10.3390/molecules21020236

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  33. Xue, L., Zhao, F.-Q., **ng, X.-L., Gao, H.-X., Xu, S.-Y., and Hu, R.-Z., Chin. J. Energ. Mater., 2009, vol. 32, p. 53. https://doi.org/10.14077/j.issn.1007-7812.2009.06.015

    Article  Google Scholar 

  34. Lan, G.-C., Wang, J.-L., Chen, L.-Z., Hou, H., Li, J., and Gao, Y.-P., J. Chem. Thermodynamics, 2015, vol. 89, p. 264. https://doi.org/10.1016/j.jct.2015.06.003

    Article  CAS  Google Scholar 

  35. Liu, N., Li, Y.-N., Zeman, S., Shu, Y.-J., Wang, B.-Z., Zhou, Y.-S., Zhao, Q.-L., and Wang, W.-L., CrystEngComm, 2016, vol. 18, p. 2843. https://doi.org/10.1039/C6CE00049E

    Article  CAS  Google Scholar 

  36. Song, L., Zhao, F.-Q., Xu, S.-Y., and Ju, X.-H., J. Mol. Graphics Modell., 2019, vol. 92, p. 303. https://doi.org/10.1016/j.jmgm.2019.08.008

    Article  CAS  Google Scholar 

  37. Song, L., Zhao, F.-Q., Xu, S.-Y., Ju, X.-H., and Ye, C.-C., Propellants, Explos., Pyrotech., 2020, vol. 45, p. 1. https://doi.org/10.1002/prep.201900398

    Article  CAS  Google Scholar 

  38. Ravi, P., Badgujar, D.M., Gore, G.M., Tewari, S.P., and Sikder, A.K., Propellants, Explos., Pyrotech., 2011, vol. 36, p. 393. https://doi.org/10.1002/prep.201100047

    Article  CAS  Google Scholar 

  39. Wang, Q.-H., Zhang, Y.-A., and **, D.-Y., Chin. J. Explos. Propellants, 2004, vol. 27, p. 14.

    Google Scholar 

  40. Wang, Q.-H., Chin. J. Explos. Propellants, 2003, vol. 26, p. 57. https://doi.org/10.14077/j.issn.1007-7812.2003.03.016

    Article  Google Scholar 

  41. Liu, Y., Liu, Z.-R., and Yin, C.-M., Chin. J. Energ. Mater., 2004, vol. 12, p. 227.

    CAS  Google Scholar 

  42. Liu, N., Zeman, S., Shu, Y.-J., Wu, Z.-K., Wang, B.-Z., and Yin, S.-W., RSC Adv., 2016, vol. 6, p. 59141. https://doi.org/10.1039/C6RA12041E

    Article  CAS  Google Scholar 

  43. Gao, J., Wang, H., Luo, Y.-M., Wang, H.-X., and Wang, W., Chin. J. Explos. Propellants, 2020, vol. 43, p. 213. https://doi.org/10.14077/j.issn.1007-7812.201811018

    Article  CAS  Google Scholar 

  44. Ren, X.-N., Heng, S.-Y., Shao, Y.-H., Liu, Z.-R., Zhang, G., Wang, X.-H., and Han, F., Chin. J. Energ. Mater., 2009, vol. 17, p. 455.

    CAS  Google Scholar 

  45. Zhou, W.-J., Liu, Z.-R., Zhang, G., Heng, S.-Y., Zhang, L.-Y., Wang, X.-H., and Ren, X.-N., The 4th Joint China/Japan Chemical Engineering Symposium, vol. 1, Chengdu, 2007, p. 1014.

  46. Shao, Y.-H., Ren, X.-N., and Liu, Z.-R., J. Therm. Anal. Calorim., 2011, vol. 103, p. 617. https://doi.org/10.1007/s10973-010-0993-4

    Article  CAS  Google Scholar 

  47. **ong, X.-F., Wang, H., Gao, J., Luo, Y.-M., and Wang, H.-X., Chin. J. Explos. Propellants, 2011, vol. 34, p. 32. https://doi.org/10.14077/j.issn.1007-7812.2011.03.009

    Article  Google Scholar 

  48. Wang, H., Gao, J., Shen, F., and Wang, X., Explos. Mater., 2020, vol. 49, p. 21. https://doi.org/10.3969/j.issn.1001-8352.2020.04.004

    Article  Google Scholar 

  49. Sun, J., Yuan, B.-H., Gu, H.-P., Wang, Q.-H., Wang, L.-X., and Zhao, K., Chin. J. Explos. Propellants, 2011, vol. 34, p. 29.

    Google Scholar 

  50. Sikder, A.K., and Reddy, S., Propellants, Explos., Pyrotech., 2013, vol. 38, p. 14. https://doi.org/10.1002/prep.201200002

    Article  CAS  Google Scholar 

  51. Yadav, A., Pant, C.S., and Das, S., Propellants, Explos., Pyrotech., 2020, vol. 45, p. 1. https://doi.org/10.1002/prep.201900329

    Article  CAS  Google Scholar 

  52. Zhao, F.-Q., Chen, P., Luo, Y., Zhang, R.-E., Zhang, Z.-Z., Zhou, Y.-S., and Li, S.-W., J. Propul. Technol., 2004, vol. 25, p. 570. https://doi.org/10.13675/j.cnki.tjjs.2004.06.021

    Article  CAS  Google Scholar 

  53. Zou, Z., Zhao, F., Zhang, M., Tian, J., and Wang, X., Explos. Mater., 2019, vol. 48, p. 11. https://doi.org/10.3969/j.issn.1001-8352.2019.04.002

    Article  Google Scholar 

  54. Meng, L.-L., Qi, X.-F., Wang, J.-N., and Fan, X.-Z., Chin. J. Explos. Propellants, 2015, vol. 38, p. 86. https://doi.org/10.14077/j.issn.1007-7812.2015.03.017

    Article  Google Scholar 

  55. Li, X., Wang, B.-L., Lin, Q.-H., and Chen, L.-P., J. Energ. Mater., 2016, vol. 34, p. 409. https://doi.org/10.1080/07370652.2015.1112447

    Article  CAS  Google Scholar 

  56. Feng, X.-J., Yang, J.-G., Xu, H.-T., and Tian, X., Chin. J. Energ. Mater., 2016, vol. 24, p. 752.

    CAS  Google Scholar 

  57. Wang, H., Gao, J., Tao, J., Luo, Y.-M., and Jiang, Q.-L., Chin. J. Energ. Mater., 2019, vol. 27, p. 897.

    Google Scholar 

  58. Yu, S., and Li, H., J. Chem., 2016, vol. 2016, p. 1. https://doi.org/10.1155/2016/6521913

    Article  CAS  Google Scholar 

  59. An, C.-W., Li, W.-X., Wen, X.-M., Wang, J.-Y., Wei, Y.-J., and Yu, B.-S., Chin. J. Energ. Mater., 2017, vol. 25, p. 132.

    CAS  Google Scholar 

  60. An, C., Wen, X., Wang, J., and Wu, B., Cent. Eur. J. Energ. Mater., 2016, vol. 13, p. 397.

    Article  CAS  Google Scholar 

  61. Wei, L., Wang, Q.-L., Liu, S.-W., Zhu, C.-Y., Guo, F., and Zhang, Y.-B., Chin. J. Explos. Propellants, 2009, vol. 32, p. 17.

    CAS  Google Scholar 

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Funding

Financial support from the **’an Modern Chemistry Research Institute [no. 204J20190387] is gratefully acknowledged. Sincere thanks to all the authors for their hard work on this article.

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  1. School of Environment and Safety Engineering, North University of China, 030051, Taiyuan, China

    Y. Li, J. M. Yuan, W. Zhao, Y. Qu, X. W. **ng, J. W. Meng & Y. C. Liu

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  1. Y. Li
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  2. J. M. Yuan
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  3. W. Zhao
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  4. Y. Qu
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Li, Y., Yuan, J.M., Zhao, W. et al. Application and Development of 3,4-Bis(3-nitrofurazan-4-yl)furoxan (DNTF). Russ J Gen Chem 91, 445–455 (2021). https://doi.org/10.1134/S1070363221030142

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