505-71-5

Usage

Uses

Used in Military and Defense Applications:
N,N'-dinitroethylenediamine is used as a high-energy explosive in military and defense applications due to its high stability and insensitivity to shock, ensuring safety and reliability in various scenarios.
Used in Propellant Production:
FOX-7 is utilized as a key ingredient in the production of propellants, leveraging its high energy output and thermal stability to enhance the performance of these materials.
Used in Explosive Compositions:
N,N'-dinitroethylenediamine is employed as a component in explosive compositions, where its high energy yield and superior mechanical properties contribute to the effectiveness of the explosives.
Used in Pyrotechnic Compositions:
FOX-7 is used as a pyrotechnic compound, taking advantage of its high energy release and thermal stability to create visually impressive and reliable pyrotechnic effects.

Upstream product

• 4938-92-5 N-(2-formylaminoethyl)formamide 
• 922-89-4 N,N'-dinitro-N,N'-ethanediyl-bis-acetamide 
• 2639-89-6 N,N'-dinitro-N,N'-ethane-1,2-diylbis(carbamic acid) diethyl ester 
• 165896-98-0 1,4-dinitro-piperazine-2,3-dione 
• 41404-99-3 N,N'-divinyl-N,N'-dinitroethylenediamine 
• 5754-91-6 1,3-dinitro-1,3-diazacyclopentane 
• 2536-18-7 1,3-dinitroimidazolidin-2-one 
• 7732-18-5 water 
• 10120-27-1 N-hydroxymethylethylenedinitroamine 
• 120-93-4 imidazolidone 
• 3082-46-0 N,N'-dinitro-N,N'-ethanediyl-bis-carbamic acid dimethyl ester 
• 7664-41-7 ammonia 
• 28236-80-8 N,N'-dichloro-N,N'-dinitro-ethylenediamine 
• 58851-62-0 tetra-N-chloro-ethylenediamine 

Downstream Products

• 14168-48-0 2,5-dinitro-2,5-diaza-1,6-hexanediyl diacetate 
• 10308-90-4 N-methyl-N,N'-dinitroethylenediamine 
• 4164-34-5 2,5-dinitro-2,5-diazahexane 
• 28236-80-8 N,N'-dichloro-N,N'-dinitro-ethylenediamine 
• 107-21-1 ethylene glycol 
• 7732-18-5 water 
• 75-07-0 acetaldehyde 

Relevant academic research and scientific papers

Crystal Engineering of Energetic Materials: Co-crystals of Ethylenedinitramine (EDNA) with Modified Performance and Improved Chemical Stability

In the area of energetic materials, co-crystallization is emerging as a new technology for modifying or enhancing the properties of existing energetic substances. Ethylenedinitramine (EDNA) is a known energetic material which requires attention partly due to its chemical instability originating with its two highly acidic protons. In order to stabilize EDNA, a co-crystallization approach targeting the acidic protons using a series of co-crystallizing agents with suitable hydrogen-bond acceptors was employed. Fifteen attempted co-crystallizations resulted in eight successful outcomes and six of these were crystallographically characterized and all showed evidence of hydrogen bonds to the intended protons. Calculated detonation properties and experimental thermal and impact data for the co-crystals were obtained and compared with those of pure EDNA. The co-crystal of EDNA and 1,2-bis(4-pyridyl)ethylene was recognized as a more thermally stable alternative to EDNA while the co-crystal of EDNA and pyrazine N,N′-dioxide showed comparable detonation strengths (and much improved chemical stability) compared with that of EDNA. The co-crystals EDNA:4,4′-bipyridine and EDNA:pyrazine N,N′-dioxide were found to be about 50 % less impact sensitive than EDNA, all of which illustrate how co-crystallizations can be utilized for successfully modifying specific aspects of energetic materials. The taming of EDNA: Ethylenedinitramine (EDNA) is a known energetic material the chemical instability of which originates with its two highly acidic protons. Co-crystallizations of EDNA demonstrate that the acidic protons can be targeted with suitable hydrogen-bond acceptors, which improves chemical stability and offers an avenue for modulating thermal properties, impact sensitivity, and overall performance of the material (see picture).

Investigation of Ethylenedinitramine as a Versatile Building Block in Energetic Salts, Cocrystals, and Coordination Compounds

Ethylenedinitramine (H2EDN, 1) was prepared in a simple manner and with a high overall yield by direct nitration of 2-imidazolidinone using 100% HNO3 at 0 °C and subsequent hydrolysis in water at 100 °C. The versatility of 1 allows its application as starting material for a broad range of different materials. It was used for the preparation of both various salts and cocrystalline materials incorporating varying amounts of the TATOT moiety. Furthermore, H2EDN was successfully applied in the concept of energetic coordination compounds (ECCs) resulting in five copper(II) and two silver(I) complexes. A reaction path for the direct precipitation or slow crystallization of 17 different salts, including several alkali, alkaline earth, silver, and nitrogen-rich samples, is presented. The substances were extensively characterized by low-temperature single-crystal X-ray diffraction, elemental analysis (EA), IR spectroscopy, differential thermal analysis (DTA), and thermogravimetric analysis (TGA), proving their high thermal stability, especially of the alkali salts. In addition, 1 and all salts were characterized by 1H, 13C, and 14N NMR, whereas 1 was also investigated using the beneficial 1H-15N HMBC NMR spectroscopy. The sensitivities toward various mechanical stimuli according to BAM standard methods, as well as ball drop impact and electrostatic discharge (ESD) were determined using the BAM 1-out-6 method. Hot plate and hot needle tests were performed, followed by further characterization of the copper(II)-based ECCs through laser ignition experiments and UV-vis spectroscopy, offering new candidates for nontoxic, less sensitive laser-ignitable materials. Several detonation parameters were calculated using EXPLO5 (V6.05.02).

Energetic propane-1,3-diaminium and butane-1,4-diaminium salts of N,N′-dinitroethylenediazanide: syntheses, crystal structures and thermal properties

The acidity of the amine H atoms and the consequent salt formation ability of ethylenedinitramine (EDNA) were analyzed in an attempt to improve the thermal stability of EDNA. Two short-chain alkanediamine bases, namely propane-1,3-diamine and butane-1,4-diamine, were chosen for this purpose. The resulting salts, namely propane-1,3-diaminium N,N′-dinitroethylenediazanide, C3H12N22+·C2H4N4O42?, and butane-1,4-diaminium N,N′-dinitroethylenediazanide, C4H14N22+·C2H4N4O42?, crystallize in the orthorhombic space group Pbca and the monoclinic space group P21/n, respectively. The resulting salts display extensive hydrogen-bonding networks because of the presence of ammonium and diazenide ions in the crystal lattice. This results in an enhanced thermal stability and raises the thermal decomposition temperatures to 202 and 221 °C compared to 180 °C for EDNA. The extensive hydrogen bonding present also plays a crucial role in lowering the sensitivity to impact of these energetic salts.

Safe and Convenient Synthesis of Primary N -Nitramines in the Freon Media

A convenient one-pot synthesis of primary aliphatic N-nitramines, which includes the nitration of available N,N′-dialkyloxalamides or N-alkylcarbamates with dinitrogen pentoxide in the 1,1,1,2-tetrafluoroethane media followed by ammonolysis of intermediate N-nitroamides in the same solvent has been developed. The method is environmentally safe, and affords target N-nitramines in up to 94% overall yield.

Process for the synthesis and recovery of nitramines

A method is provided for the synthesis of nitramines, and the recovery of the nitramines from a clathrate.

REACTIVITY OF N-NITROENAMINES

The effect of a substituent at the α-carbon atom of the vinyl group in N-nitroenamines on their reactivity is explained by steric hindrances to pN-?C=C conjugation.The acid-catalyzed rearrangement of N-(tert-butylvinyl)-N-methylnitroamine to N-(1-tert-butyl-2-nitrovinyl)-N-methylamine was discovered.Under analogous conditions methyl(vinyl)-N-nitroamine undergoes cleavage to methylnitroamine and acetaldehyde.Unlike unconjugated N-nitroenamines, which are converted into C-nitroenamines when heated, methyl(vinyl)-N-nitroamine undergoes cleavage by a deamination mechanism with the release of nitrous oxide.

DERIVATIVES OF NITROAMINOMETHANOLS. III. REACTIONS OF 1-NITROAMINOMETHYL ACETATES IN ACIDIC MEDIA

The hydrolysis of 1-nitroaminomethyl acetates with acid catalysis occurs under mild conditions with the formation of primary nitroamines.Increase in the concentration of acid in the reaction mixture leads to deamination of the initial compounds.