US Government As Represented by the Secretary of the Army

Raja G Duddu

Paritosh R Dave

Reddy Damavarapu

Kathy Yang

Nathaniel S Gelber

C Rao Surapaneni

Rao C Surapaneni

Neha Mehta

Daniel Stec, Iii

Emily A Cordaro

Carl Hu

Neelam Mehta

Robert Lateer

Gartumg Cheng

MaoXi Zhang

John H Hoare

A one-pot process for preparing ammonium and hydroxylammonium salts of bis 5,5'-tetrazole-1,1&#x2032;-dihydroxide, specifically, diammonium bis 5,5&#x2032;-tetrazole-1,1&#x2032;-diolate (ABTOX) and dihydroxylammonium 5,5&#x2032;-bistetrazole-1,1&#x2032;-diolate (TKX-50). The process requires the reaction of sodium azide, dichloroglyoxime, HCl in dioxane solution to form bis 5,5&#x2032;-tetrazole-1,1&#x2032;-dihydroxide and treating this product with either ammonium chloride to produce ABTOX or hydroxylamine hydrochloride to produce TKX-50.

One-pot process for preparation of ammonium and hydroxyl ammonium derivatives of bis 5,5'-tetrazole-1,1&#x2032;-dihydroxide

A novel method for preparing 3-chlorocarbohydroxymoyl-4-nitro-1,2,5-oxadiazole by reacting 4-amino-3-chlorocarbohydroxymoyl-1,2,5-oxadiazole with HOand a tungsten based catalyst and use of the prepared 3-chlorocarbohydroxymoyl-4-nitro-1,2,5-oxadiazole for synthesizing 3,4-Bis(4-nitro-1,2,5-oxadizaol-3-yl)-1,2,5-oxadiazole-N-oxide (DNTF).

Synthesis of 3,4-Bis(4-nitro-1,2,5-oxadizaol-3-yl)-1,2,5-oxadizaole-N-oxide (DNTF) using 3-chlorocarbohydroxymoyl-4-nitro-1,2,5-oxadizaole

Energetic candidate azido heterocycles and their synthesis are described.

Synthesis of azido heterocycles

A method for synthesizing pentanitrohexaazaisowurtzintane under neutral reaction conditions. Which synthesis involves treating a solution of hexanitrohexaazaisowurtzitane in ethyl acetate in the presence of a catalytic quantity of palladium on a carbon substrate, until a heterogeneous mixture is formed. This heterogeneous mixture is hydrogenated under a balloon atmosphere until the starting hexanitrohexaazaisowurtzitane is substantially reacted. The resulting pentanitrohexaazaisowurzitane mixture is filtered, dried and recovered from the dried residue through a Si-gel column.

Hydrogenolytic denitration of polynitro compounds: pentanitrohexaazaisowurtzitane

A lead-free primer energetic composition including Cyanuric Triazide (60%), Tetracene (5%), Barium Nitrate (20%) and Antimony Trisulfide (15%) is produced. The lead-free primer energetic composition is used to construct a primary detonator including a transfer charge of Cyanuric Triazide, which produces a further initiation train that may subsequently detonate a secondary explosive, i.e., HDX, RDX, or a pyrotechnic device.

Lead free detonator and composition

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).

Processes and compositions for nitration of N-substituted isowurtzitane compounds with concentrated nitric acid at elevated temperatures to form HNIW and recovery thereof with high yields and purities. Polymorphic conversions to the epsilon HNIW crystal form at quanititative yields are also described.

Process and compositions for nitration of n-nitric acid at elevated

Processes and compositions for nitration of N-substituted isowurtzitane compounds with concentrated nitric acid at elevated temperatures to form HNIW and recovery of gamma HNIW with high yields and purities. Polymorphic conversion of HNIW crystals to epsilon HNIW crystals is also disclosed.

Growing community of inventors

Hackettstown, NJ, United States of America

Raja G Duddu