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A Study of the Synthesis and Amination of 2,6-Dialkoxy-3,5-dinitropyrazines

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EN
Abstrakty
EN
A series of 2,6-dialkoxy-3,5-dinitropyrazines (R = Me, Et, Pr) has been synthesized and subjected to amination. The yield and purity of the generated 2,6-diamino-3 ,5-dinitropyrazine was found to be independent of the alkoxy group present in the precursor. This contrasts with the behaviour of 1,3,5-trialkoxy-2,4,6-trinitrobenzene (R = Me, Et, Pr), where the purity of the 1,3,5-triamino- 2,4,6-trinitrobenzene (TATB) produced by amination was very dependent upon the alkoxy group.
Rocznik
Strony
3--19
Opis fizyczny
Bibliogr. 13 poz.
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autor
Bibliografia
  • [1] Pagoria P.F., Mitchell A.R., Schmidt R.D., Simpson R.L., Garcia F., Forbes J., Cutting J., Lee R., Swansiger R., Hoffman D.M., Synthesis, Scale-up and Experimental Testing of LLM-105 (2,6-diamino-3,5-dinitropyrazine 1-oxide, Insensitive Munitions & Energetic Materials Technology Symposium, San Diego, CA, 1998, I-3-1 to I-3-5.
  • [2] Tartakovskii V.A., Shitov O.P., Yudin I.L., Myasnikov V.A., Method for the Preparation of 2,6-Diamino-3 ,5-dinitropyrazine and 6-chloro-3 ,5-dinitro-2-methoxypyrazine as an Intermediate for its Synthesis, SU 1703645 A1 (1992).
  • [3] Kerth J., Kuglstatter W., Synthesis and Characterisation of 2,6-Diamino-3 ,5-dinitropyrazine 1-oxide (NPEX-1), International Annual Conference of ICT, 2001, 32nd (Energetic Materials), 166/1-166/11.
  • [4] Pagoria P., Lee G.S., Mitchell A.R., Schmidt R.D., The Synthesis of Amino- and Nitro-substituted Heterocycles as Insensitive Energetic Materials, Insensitive Munitions & Energetic Materials Technology Symposium, Bordeaux, France, Oct. 8‑11, 2001, 2, 655-661.
  • [5] Bellamy A.J., Golding P., The Study of Some Potential New Synthetic Routes to LLM-105 (2,6-diamino-3,5-dinitropyrazine 1-oxide ), Centr. Europ. J. Energ. Mater., 2007, 4(3), 33-57.
  • [6] Bellamy A.J., Golding P., Ward S.J., A New Synthetic Route to Triaminotrinitrobenzene (TATB), Insensitive Munitions & Energetic Materials Technology Symposium, Bordeaux, France, Oct. 8‑11, 2001, 2, 626-634.
  • [7] Bellamy A.J., Golding P., Ward S.J., Synthesis of TATB and DATB from Trihydroxybenzene and Dihydroxybenzene by Nitration, Alkylation, and Amination, GB 2355713 A (2001).
  • [8] Bellamy A.J., Ward S.J., Golding P., A New Synthetic Route to 1,3,5-Triamino-2,4,6-trinitrobenzene (TATB), Propellants, Explos., Pyrotech., 2002, 27(2), 49-58.
  • [9] Bellamy A.J., Golding P., Ward S.J., Amination of 1,3,5-Trialkoxy-2,4,6-trinitrobenzene; Formation of TATB vs. ADAP (ammonium 3,5-diaminopicrate), 33rd International Annual Conference of ICT (Energetic Materials), (2002), 1/1-1/10.
  • [10] Dressen S., Merrill D., Mancini V., Sanderson A., Velarde S., Pilot Plant Synthesis of Triaminotrinitrobenzene (TATB), Insensitive Munitions & Energetic Materials Technology Symposium (NDIA), 24-28 April 2006, Bristol, UK.
  • [11] Cheeseman G.W.H., Törzs E.S.G., Pyrazines. Part II. The Preparation and Reactions of 2,3-, 2,5- and 2,6-Disubstuted Pyrazines, J. Chem. Soc., 1965, 6681-6688.
  • [12] Schaaf K.H., Spoerri P.E., Syntheses in the Pyrazine Series: the Proof of the Structure and the Reactions of 2,6-dibromopyrazine, J. Org. Chem., 1949, 71, 2043- 2047.
  • [13] Donald K.H., Tetraminopyrazine, 2,3,5-Triamino-6-nitropyrazine, 2,6‑Diamino-3,5-dinitropyrazine, US 3808209 (1974).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BAT1-0034-0046
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