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

Jing S., Liu Y., Liu D., Guo J.

Central European Journal of Energetic Materials

2016

Vol. 13, no. 1

21--32

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.

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

Bellamy A. J., Golding P.

Central European Journal of Energetic Materials

2008

Vol. 5, nr 2

3-19

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.

The Study of Some Potential New Synthetic Routes to LLM-105 (2,6-Diamino-3,5-dinitropyrazine 1-oxide)

Bellamy A. J., Golding P.

Central European Journal of Energetic Materials

2007

Vol. 4, nr 3

33-57

The synthesis of LLM-105 (2,6-diamino-3,5-dinitropyrazine 1-oxide) via the direct nitration of 2,6-diaminopyrazine 1-oxide is reported. Two synthetic routes to the starting material 2,6-diaminopyrazine 1-oxide have been investigated. The synthesis of 2,6-diamino-3,5-dinitropyrazine by nitration of 2,6-diaminopyrazine and 2,6-diacetamidopyrazine has also been studied. Whilst mono-nitration of 2,6-diaminopyrazine is very selective, further nitration leads to mixtures of 2,6-diamino-3,5-dinitropyrazine, 6-amino-2-keto-3,5-dinitropyrazine and tetraketopiperazine, the latter predominating in many cases. It was shown that tetraketopiperazine is formed by further reaction of the initially formed 2,6-diamino-3,5-dinitropyrazine. Nitration of 2,6-diacetamidopyrazine does furnish 2,6-diamino-3,5-dinitropyrazine, but the yield is poor.