Skip to main content
SpringerLink
Log in

Synthesis of N,N-dialkylnitramines from secondary ammonium nitrates in liquid or supercritical carbon dioxide

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

An efficient explosion-proof method was developed for the preparation of N,N-dialkylnitramines by treatment of dialkylammonium nitrates with a mixture of nitric acid and acetic anhydride in the presence of ZnCl2 in liduid or supercritical carbon dioxide.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. R. Mayer, Explosives, 5-th ed. (Electronic), Wiley-VCH Verlag, GmbH, 2002.

    Google Scholar 

  2. Pat. Fr. 1377695; Chem. Abstr., 1965, 62, 11087.

  3. Pat. GB 1005860; Chem. Abstr., 1965, 63, 71911.

    Google Scholar 

  4. J. Giziewicz, S. F. Wnuk, M. J. Robins, J. Org. Chem., 1999, 64, 2149.

    Article  CAS  Google Scholar 

  5. O. Gorchs, M. Hernandez, L. Garriga, E. Pedroso, A. Grandas, J. Farras, Org. Lett., 2002, 4, 1827.

    Article  CAS  Google Scholar 

  6. R. L. Willer, J. Org. Chem., 1984, 49, 5150.

    Article  CAS  Google Scholar 

  7. J. H. Robson, J. Reinhart, J. Am. Chem. Soc., 1955, 77, 2453.

    Article  CAS  Google Scholar 

  8. R. L. Willer, R. L. Atkins, J. Org. Chem., 1984, 49, 5147.

    Article  CAS  Google Scholar 

  9. W. D. Emmons, A. S. Pargano, T. E. Stevens, J. Org. Chem., 1958, 23, 311.

    Article  CAS  Google Scholar 

  10. P. Golding; R. W. Millar, N. C. Paul, D. H. Richards, Tetrahedron Lett., 1988, 29, 2735.

    Article  CAS  Google Scholar 

  11. R. W. Millar, S. P. Philbin, Tetrahedron, 1997, 53, 4371.

    Article  CAS  Google Scholar 

  12. W. D. Emmons, J. P. Freeman, J. Am. Chem. Soc., 1955, 77, 4387.

    Article  CAS  Google Scholar 

  13. J. C. Bottaro, R. J. Schmitt, C. D. Bedford, J. Org. Chem., 1987, 52, 2292.

    Article  CAS  Google Scholar 

  14. C. M. Adams, C. M. Sharts, S. A. Shackelford, Tetrahedron Lett., 1993, 34, 6669.

    Article  CAS  Google Scholar 

  15. J. H. Robson, J. Am. Chem. Soc., 1955, 77, 107.

    Article  CAS  Google Scholar 

  16. S. C. Suri, R. D. Chapman, Synthesis, 1988, 743.

  17. A. A. Stotskii, N. I. Novatskaya, E. K. Legostaeva, B. V. Gidaspov, Zh. Org. Khim., 1978, 14, 1183 [J. Org. Chem USSR (Engl. Transl.), 1978, 14].

    CAS  Google Scholar 

  18. W. J. Chute, G. E. Dunn, J. C. MacKenzie, G. S. Myers, G. N. R. Smart, J. W. Suggitt, G. F. Wright, Can. J. Res., 1948, 26B, 114

    CAS  Google Scholar 

  19. G. F. Wright, W. J. Chute, Pat. USA 2461582, 1944, Chem. Abstr., 1949, 43, 22675.

    Google Scholar 

  20. R. Span, W. Wagner, J. Phys. Chem. Ref. Data, 1996, 25, 1509.

    CAS  Google Scholar 

  21. V. A. Rabinovich, Z. Ya. Khavin, Kratkii khimicheskii spravochnik [Brief Chemical Handbook], Eds A. A. Potekhin, A. I. Efimova, Khimiya, Leningrad, 1991, 432 pp. (in Russian).

    Google Scholar 

  22. Y. Sasson, G. Rothenberg, in Handbook of Green Chemistry and Technology, Eds J. Clark, D. Macquarrie, Blackwell Science Ltd., 2002.

  23. P. G. Jessop, J. Supercrit. Fluids, 2006, 38, 211.

    Article  CAS  Google Scholar 

  24. R.S. Oakes, A.A. Clifford, C.M. Rayner, J. Chem. Soc., Perkin Trans. 1, 2001, 917.

  25. E. J. Beckman, J. Supercrit. Fluids, 2004, 28, 121.

    Article  CAS  Google Scholar 

  26. M. J. Burk, S. Feng, M.F. Gross, W. Tumas, J. Am. Chem. Soc., 1995, 117, 8277

    Article  CAS  Google Scholar 

  27. J. Xiao, S. C. A. Nefkens, P. G. Jessop, T. Ikariya, R. Noyori, Tetrahedron Lett., 1996, 37, 2813.

    Article  CAS  Google Scholar 

  28. Z. K. Lopez-Castillo, R. Flores, I. Kani, J. P. Fackler, Ind. Eng. Chem. Res., 2002, 41 3075

    Article  CAS  Google Scholar 

  29. I. Kani, M. A. Omary, M. A. Rawashdeh-Omary, Z. K. Lopez-Castillo, R. Flores, A. Akgerman, J. P. Fackler, Tetrahedron, 2002, 58, 3923

    Article  CAS  Google Scholar 

  30. F. Zhao, Y. Ikushima, M. Chatterjee, O. Sato, M. Arai, J. Supercrit. Fluids, 2003, 27, 65

    Article  CAS  Google Scholar 

  31. F. Zhao, S.-I. Fujita, J. Sun, Y. Ikushima, M. Arai, Chem. Commun., 2004, 2326

  32. M. Berthod, G. Mignani, M. Lemaire, Tetrahedron Asym., 2004, 15, 1121

    Article  CAS  Google Scholar 

  33. X. Dong, C. Erkey, J. Mol. Catal. A: Chem., 2004, 211, 73.

    Article  CAS  Google Scholar 

  34. Y. Guo, A. Akgerman, Ind. Eng. Chem. Res., 1997, 36, 4581

    Article  CAS  Google Scholar 

  35. Y. Guo, A. Akgerman, J. Supercrit. Fluids, 1999, 15, 63

    Article  CAS  Google Scholar 

  36. C.R. Yonker, J. C. Linehan, J. Organomet. Chem., 2002, 650, 249.

    Article  CAS  Google Scholar 

  37. C. Erkey, E. L. Diz, G. Suss-Fink, X. Dong, Catal. Commun., 2002, 3, 213

    Article  CAS  Google Scholar 

  38. S. Haji, C. Erkey, Tetrahedron, 2002, 58, 3929

    Article  CAS  Google Scholar 

  39. S.-I. Fujita, S. Fujisawa, B. M. Bhanage, M. Arai, Tetrahedron Lett., 2004, 45, 1307

    Article  CAS  Google Scholar 

  40. S.-I. Fujita, S. Fujisawa, B.M. Bhanage, Y. Ikushima, M. Arai, Eur. J. Org. Chem., 2004, 2881.

  41. H. Hori, C. Six, W. Leitner, Macromolecules, 1999, 32, 3178

    Article  CAS  Google Scholar 

  42. S. A. Mang, P. Dokolas, A. B. Holmes, Org. Lett., 1999, 1, 125

    Article  CAS  Google Scholar 

  43. T. J. de Vries, R. Duchateau, M. A. G. Vorstman, J. T. F. Keurentjes, Chem. Commun., 2000, 263

  44. H. Hori, C. Six, W. Leitner, Appl. Organomet. Chem., 2001, 15, 145

    Article  CAS  Google Scholar 

  45. F. Stassin, O. Halleux, R. Jerome, Macromolecules, 2001, 34, 775

    Article  CAS  Google Scholar 

  46. M. Kemmere, T. de Vries, M. Vorstman, J. Keurentjes, Chem. Eng. Sci., 2001, 56, 4197

    Article  CAS  Google Scholar 

  47. T. J. de Vries, M. F. Kemmere, J. T. F. Keurentjes, Macromolecules, 2001, 37, 4241

    Article  Google Scholar 

  48. S. Yoda, D. Bratton, S. M. Howdle, Polymer, 2004, 45, 7839

    Article  CAS  Google Scholar 

  49. D. Bratton, M. Brown, S. M. Howdle, Macromolecules, 2005, 38, 1190

    Article  CAS  Google Scholar 

  50. X. Hu, M. T. Blanda, S. R. Venumbaka, P. E. Cassidy, Polym. Adv. Technol., 2005, 16, 146.

    Article  CAS  Google Scholar 

  51. M. B. Talawar, R. Sivabalan, T. Mukundan, H. Muthurajan, A. K. Sikder, B. R. Gandhe, A. Subhananda Rao, J. Hazardous Materials, 2009, 161, 589.

    Article  CAS  Google Scholar 

  52. G. W. Nauflett, R. E. Farncomb, in JANNAF Propellant Development and Characterization Subcommittee and Safety and Environmental Protection Subcommittee Joint Meeting, US, 1998, pp. 1–13.

  53. W. D. Emmons, J. Am. Chem. Soc., 1954, 76, 3470.

    Article  CAS  Google Scholar 

  54. A. D. Wright, R. D. Bowen, K. R. Jennings, J. Chem. Soc. Perkin Trans. 2, 1989, 1521.

  55. W. P. Norris, J. Am. Chem. Soc., 1959, 81, 3346.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    I. V. Kuchurov, I. V. Fomenkov & S. G. Zlotin

Authors
  1. I. V. Kuchurov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. V. Fomenkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. G. Zlotin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. V. Kuchurov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1995–1999, October, 2009.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kuchurov, I.V., Fomenkov, I.V. & Zlotin, S.G. Synthesis of N,N-dialkylnitramines from secondary ammonium nitrates in liquid or supercritical carbon dioxide. Russ Chem Bull 58, 2058–2062 (2009). https://doi.org/10.1007/s11172-009-0282-1

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-009-0282-1

Key words

Search

Navigation