Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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A Study on the Synthesis of Ammonium Dinitramide

ADN(Ammonium Dinitramide)의 합성

  • 정규현 (인하대학교 이과대학 화학과) ;
  • 심현호 (인하대학교 이과대학 화학과)
  • Published : 19971200
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Abstract

Recently ADN was disclosed to replace AP or AN as a solid oxidizer. 3-N,N-Dinitraminopropanitrile, a key intermediate in the preparation of ADN, was synthesized from bis(2-cyanoethyl)amine by the sequence: nitration of bis(2-cyanoethyl)amine followed by decyanoethylation by base and the second nitration with NO2BF4. 3-N-Nitro-bis(2-cyanoethyl)amine could also be obtained by the oxidation of the corresponding N-nitroso compound.

Ammonium dinitramide(ADN)은 최근에 개발된 고체 산화제로 ammonium perchlorate(AP)나 ammonium nitrate(AN) 등을 대체할 수 있다. Bis(2-cyanoethyl)amine에 니트로화 반응을 시킨 후 염기 처리하여 cyanoethyl기를 제거하고 NA2BF4를 사용하여 두번째 니트로 기를 도입하면 ADN 합성에 중요한 중간체인 3-N-Nitro-bis(2-cyanoethyl)amine은 N-nitroso 화합물의 산화반응으로 얻을 수도 있다.

Keywords

References

  1. Chem & Eng. News v.17 Borman, S.
  2. J. Phys. Chem. v.100 Russell, T. P.;Miller, P. J.
  3. PCT int. Appl. Bottaro, J. C.;Schmitt, R. J.;Penwell, P. E.;Ross, D. S.
  4. WO 91/19669,19670; U. S. Patent 5,254,324 Bottaro, J. C.;Schmitt, R. J.;Penwell, P. E.;Ross, D. S.
  5. Kayaku Gakkashi v.57 Hatano, H.;Onda, T.;Shinno, K.;Miyazaki, S.;Matsuura, S.
  6. Russ. Chem. Bull. v.43 Lukyanov, O. A.;Gorelik, V. P.;Tartakovskii, V. A.
  7. Russ. Chem. Bull. v.43 Lukyanov, O. A.;Shlykova, N. I.;Tartakovskii, V. A.
  8. Russ. Chem. Bull. v.44 Lukyanov, O. A.;Agevnin, A. R.;Leichenko, A. A.;Seregina, N. M.;Tartakovskii, V. A.
  9. Russ. Chem. Bull. v.44 Shlyapochnikov, V. A.;Oleneva, G. I.;Cherskaya, N. O.;Lukyanov, O. A.;Gorelik, V. P.;Anikin, O. V.;Tartakovskii, V. A.
  10. Kayaku Gakkashi v.58 Takishita, Y.;Teramoto, Y.
  11. J. Phys. Chem. A v.101 Oxley, J.;Smith, J.;Zheng, W. O.;Rogers, E.;Coburn, M.
  12. Nitration, Methods and Mechanism Olah, A.;Malhotra, R.;Narang, S. C.
  13. Can. J. Research v.26B Chute, W. J.;Herring, K. G.;Toonbs, L. E.;Wright, G. F.
  14. J. Org. Chem. v.23 Framkel, M. B.;Vanneman, C. R.
  15. Ger. 1,085,116. Reilly, E. L.
  16. CA. v.56
  17. J. Am. Chem. Soc. v.76 Emmono, W. D.
  18. J. Org. Chem. v.60 Marchald, A. P.;Rajagopal, S. G.;Bott, S. G.;Arckibald, T. G.
  19. J. Am. Chem. Soc. v.77 Robson, J. H.;Reinhart, J.
  20. Collect. Czech. Chem. Commun. v.42 Kaderabek, V.;Denkstein, J.
  21. Brit. Pat. 1,126,591. Aerojet-General Corp.
  22. CA v.70