Ritter
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Ammonium 2,4,5-trinitroimimidazole & other nitrated imidazoles
From http://enermat.org.ru/explosive-2.html
| Quote: | The transformation of 4-nitroimidazole (3) into 1,4-dinitroimidazole (4) could be brought about by treatment with acetyl nitrate (AcONO2), which could
be generated in the mixed solution of acetic anhydride and fuming nitric acid in acetic acid in situ at low temperature [6]. It took two days to get
excellent yield (95 %) of 4. There are about 3 % of unreacted 3 as the major impurity, which can be removed by the extraction with methylene chloride.
This compound 4 is so thermally unstable at the elevated temperature (over 50 °C) that nitro group of 1-position can be deleted to return to 3.
2,4-Dinitroimidazole (5) was prepared from 4 by thermal rearrangement with refluxing in chlorobenzene [6]. The yield was 93 %. In general, the
synthesized 5 were contaminated with 3 in a small amount. It is probably that very small portion of 4 might go back to 3 during the rearrangement.
Along with above thermal decomposition, 3 in 5 can come from the contaminated 4. To minimized 3 in 5, it is important to get rid of 3 when making 4.
The 3rd nitration to 2,4,5-trinitroimidazole (6) was performed in the mixed acid condition. As the intermediate of potassium 2,4,5-trinitroimidazolate
(7), 6 was not stable enough that we could not isolate that. From the extracted ether solution of 6, the solid of 7 was precipitated with the
saturated K2CO3/KCl solution in good yield (60 %) [15]. It was reported that 6 could be manufactured via 2,4,5-triiodoimidazole, but we chose the
route through 2,4-DNI (5).
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The ChemDraw attachment summarizes the above sequence as well as patent US4028154 to the U.S. ERDA (now DOE).
Ammonium 2,4,5-trinitroimidazole is stated to have explosive power compartable to RDX but with better thermal stability.
[Edited on 25-7-2008 by Ritter]
Ritter
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\"The production of too many useful things results in too many useless people.\"
Karl Marx
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Formatik
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Estimated VOD of the NH4 salt is 8560 m/s, and C-j pressure: 330 kbar. Shock sensitivity (type 12): 50.3 cm. Thermal stability greater than RDX.
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Ritter
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Additional reference:
| Quote: | 2,4,5-Trinitroimidazole-Based Energetic Salts
Haixiang Gao, Chengfeng Ye, OmD. Gupta, Ji-Chang Xiao, MichaelA. Hiskey, Brendan Twamley, Jean'neM. Shreeve
Chemistry - A European Journal 13(14):3853 (2007) |
Ritter
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\"The production of too many useful things results in too many useless people.\"
Karl Marx
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Ritter
Hazard to Others
Posts: 370
Registered: 20-6-2008
Location: Earth
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Mood: Curious
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The explosive properties & preparation of 2,4-dinitroimidazole are disclosed in patent US5387297 along with the preparation of 1,4-dintroimidazole
& its thermal rearrangement to 2,4-dinitromidazole. See http://www.pat2pdf.org/patents/pat5387297.pdf.
Government codes for these materials are stated as follows:
DNI-24 - 2,4-Dintroimidazole
DNI-14 - 1,4-Dinitroimidazole
The detonation pressure of DNI-24 is stated as being equal to that of RDX & TNT but with decreased sensitivity to shock & impact when compared
to those materials.
Ritter
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\"The production of too many useful things results in too many useless people.\"
Karl Marx
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