US Government As Represented by the Secretary of the Army

Nathaniel S Gelber

Paritosh R Dave

Reddy Damavarapu

Raja G Duddu

C Rao Surapaneni

Kathy Yang

Rao C Surapaneni

MaoXi Zhang

1-Methyl-2,4,5-Trinitroimidazole is synthesized starting from 4-nitroimidazole using stepwise nitration method and further methylation using Dimethylsulphate. It is relatively insensitive to impact and its thermal stability is excellent. The calculated detonation properties indicate that its performance is about 30% better than TATB. It can be prepared easily, with reasonable yield, starting from commercially available Imidazole. Results from impact sensitivity, friction sensitivity, time-to-explosion temperature and vacuum stability tests indicate that it is less sensitive than both RDX and HMX. The good oxygen balance and measured heat of formation data of this material indicate that its propellant performance should be good.

Melt-cast explosive material

The invention relates to a novel polyazido compound: 2,2-dinitro-1,3-diazidopropane.

Polyazido compounds

The compound 3a,8a-bis-azidomethyl-3a,4,8a,9-tetrahydro-3H,8H-bis-[1,2,3]triazolo[1,5-a;1&#x2033;,5&#x2033;-d]pyrazine, whose structure is depicted below, is disclosed:

The compound 2,2-bis(azidomethyl)oxirane, whose structure is depicted below, is disclosed:

This invention relates to a series of novel compounds having the general structures A and B:including 2-azido-2-azidomethyl-1,3-diazidopropane (1), 2-azidomethyl-2-hydroxy-1,3-diazidopropane (2), 2-azidomethyl-2-nitrato-1,3-diazidopropane (3), 2-azidomethyl-2-nitro-1,3-diazidopropane (4), 2,2-dinitro-1,3-diazidopropane (5), methallyidiazide (6), a dimer of methallyidiazide (6), comprising 3a,8a-Bis-azidomethyl-3a,4,8a,9-tetrahydro-3H,8H-bis[1,2,3]triazolo[1,5-a;1&#x2033;,5&#x2033;-d]pyrazine (6-Dimer), 1,3-diazidoacetone (7), and 2-Oximido-1,3-diazidopropane (8). Also shown are reaction intermediates of these compounds, including 2,2-bis(chloromethyl)oxirane (9), and 2,2-bis(azidomethyl)oxirane (10). In addition, a number of potentially useful energetic compounds have been prepared from the low molecular weight polyazido compounds above, including N-2(azido-1-azidomethyl-ethylidene)-N&#x2033;-(2,4-dinitrophenyl)-hydrazine (7-DNPH), 1,3-Bis(4-carboxytriazolyl)2,2-dinitropropane (12), Tris(4-carboxytriazolomethyl)methanol (13), Benzene-1,3,5-tricarboxylic acid tris(2-azido-1,1-bisazidomethyl-ethyl)ester (14), Adamantane 1,3,5,7-tetracarboxylic acid tetrakis(2-azido-1,1-bisazidomethyl-ethyl)ester (15), Adamantane carboxylic acid 2-azido-1,1-bisazidomethyl-ethyl)ester (16), cubane 1,3,5,7-tetracarboxylic acid tetrakis (2-azido-1,1-bisazidomethyl-ethyl)ester (17), cubane 1,4-dicarboxylic acid bis(2-azido-1,1-bisazidomethyl-ethyl)ester (18).

1,3,5,7-Tetraacetyloctahydro-1,3,5,7-tetrazocine is produced in improved ld by reacting 1,5-diacetyl-1,3,5,7-tetraazabicyclo-[3.3.1]-nonane with acetic anhydride in the presence of a metal acetate, such as sodium acetate.

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Morristown, NJ, United States of America

Nathaniel S Gelber