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Research on a New Synthesis of LLM-105 Using N-Nitroso-bis(cyanomethyl)amine

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Treść / Zawartość
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Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
A new three-step synthetic method was designed to prepare 2,6-diamino- 3,5-dinitropyrazine 1-oxide (LLM-105) with an overall yield of 43.5%, using iminodiacetonitrile, triethylamine and hydroxylamine hydrochloride as the starting materials, and involved nitrosylation, cyclization and nitration. The structure of LLM-105 was characterized by FTIR, 1H NMR spectroscopy and elemental analysis. The crucial factors and mechanism of the cyclization were explored. Thermal decomposition, mechanical sensitivity and the purity of the LLM-105 were determined by TG-DTA, an impact sensitivity instrument and high performance liquid chromatography (HPLC) respectively. The results showed that LLM-105 synthesised via 2,6-diamino-3,5-dinitropyrazine (ANPZ) was less sensitive to impact, but the LLM-105 synthesized by the new method had some obvious advantages in terms of purity, security and production costs. Moreover, the LLM-105 synthesized by this new method can be initiated reliably without recrystallization.
Rocznik
Strony
21--32
Opis fizyczny
Bibliogr. 20 poz., rys., tab.
Twórcy
autor
  • School of Chemical Engineering and Environment, North University of China, Taiyuan 030051, China
autor
  • School of Chemical Engineering and Environment, North University of China, Taiyuan 030051, China
autor
  • School of Chemical Engineering and Environment, North University of China, Taiyuan 030051, China
autor
  • School of Chemical Engineering and Environment, North University of China, Taiyuan 030051, China
Bibliografia
  • [1] Pagoria P.F., Synthesis of LLM-105, Propellants Explos. Pyrotech., 1995, 20(1), 38-42.
  • [2] Pagoria P.F., Scale-up and Characterization of 2, 6-Diamino-3, 5-dinitropyrazine-1-oxide, Propellants Explos. Pyrotech., 1998, 23(3), 156-160.
  • [3] Li H.B., Cheng B.B., Synthesis of ANPZ and Crystal Structure of ANPZ DMSO (1:1), Chemical Research and Application, 2007, 19(3), 293.
  • [4] Li H.B., Cheng B.B., Liu S.J., Nie F.D., Li J.S., Recrystallization and Properties of LLM-105, Energ. Mater., 2008, 16(6), 686.
  • [5] Pagoria P.F., Synthesis, Scale-up and Experimental Testing of ANPZO, Proc. 1998 Insensitive Munitions and Energetic Materials Technology Symposium, San Diego, 1998.
  • [6] Glascoe E.A., Tan N., Koerner J., Pressure and Temperature Dependent Deflagration Rate Measurements of ANPZO and TATB Based Explosive, JANNAF 25th Propulsion Systems Hazards, United States, 2009.
  • [7] Glascoe E.A., Maienschein J.L., Deflagration Rate Measurements of Three Insensitive High Explosives: ANPZO, TATB and DAAF, 14th Int. Detonation Symposium, United States, 2010.
  • [8] Averkiev B.B., Antipin M.Y., Yudin I.L., Sheremetev A.B., Four 3-Cyanodifurazanyl Ethers: Potential Propellants, J. Mol. Struct., 2002, 606, 139-146.
  • [9] Tran T.D., Pagoria P.F., Hoffman D.M., Simpson R.L., Lee R.S., Characterization of 2,6-Diamino-3,5-dinitropyrazine-1-oxide (LLM-105) as an Insensitive High Explosive Material, 33rd Int. Annu. Conf. ICT, Karlsruhe, Germany, 2002.
  • [10] Hoffman D.M., Lorenz K.T., Cunningham B., Formulation and Mechanical of ANPZO-PBXs, 39th Int. Annu. Conf. ICT, Karlsruhe, Germany, 2008.
  • [11] Weese R.K., Burnham A.K., Physical Characterization of RX-55-AE-5 a Formulation of 97.5% 2,6-Diamino-3,5-dinitropyrazine-1-oxide (ANPZO) and 2.5% Viton A, Lawrence Livermore National Laboratory Report No. UCRLCONF- 214557, 2005.
  • [12] Weese R.K., Burnham A.K., Turner H.C., Tran T.D., Exploring the Physical, Chemical and Thermal Characteristics of a New Potentially Insensitive High Explosive: RX-55-AE-5, J. Therm. Anal. Calorim., 2007, 89, 465.
  • [13] Guo F.B., Liu Y.C., Liu D.C., Yu Y.W., Optimization of the Synthetical Craft of 2,6-Diamino-3,5-dinitropyrazine-1-oxide, Chinese Journal of Explosives & Propellants, 2006, 29(1), 17-19.
  • [14] Wang Z.Y., Development on Some New Insensitive Individual Explosives Abroad, Energ. Mater., 2003, 11(4), 227-230.
  • [15] Pagoria P.F., Alexander R.M., Bala K., New Synthesis of 2,6-Diamino-3,5-dinitropyrazine 1-oxide from 2,6-Diaminopyrazine 1-oxide, US Patent 20090299067, 2009.
  • [16] Pagoria P.F., Mao X.Z., Synthesis of Pyrazines Including 2,6-Diaminopyrazine 1-oxide (DAPO) and 2,6-Diamino-3,5-dinitropyrazine 1-oxide (LLM-105), US Patent 20100267955, 2010.
  • [17] Bellamy A.J., Golding P., A New Synthetic Route to LLM-105 (2,6-Diamino-3,5-dinitropyrazine 1-oxide), New Trends Res. Energ. Mater., Proc. Semin., 11th, Pardubice, Czech Republic, 2008, 465-474.
  • [18] Bellamy A.J., Golding P., The Study of Some Potential New Synthetic Routes to LLM-105 (2,6-Diamino-3,5-dinitropyrazine 1-oxide), Cent. Eur. J. Energ. Mater., 2007, 4(3), 33-57.
  • [19] He W.D., Zhou G., Li J.S., Tian A.M., Molecular Design of Analogues of 2,6-Diamino-3,5-dinitropyrazine 1-oxide, J. Mol. Struct., 2004, 668, 201-208.
  • [20] Li H.B., Cheng B.B., Synthesis of 2,6-Diamino-3,5-dinitropyrazine 1-oxide, Chinese Journal of Organic Chemistry, 2007, 27(1), 112-115.
Uwagi
Opracowanie ze środków MNiSW w ramach umowy 812/P-DUN/2016 na działalność upowszechniającą naukę.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-ec070bff-a0e8-49e2-81d6-1d87233e006e
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