2536-18-7Relevant academic research and scientific papers
ELECTROPHILIC TETRAALKYLAMMONIUM NITRATE NITRATION. I. CONVENIENT NEW ANHYDROUS NITRONIUM TRIFLATE SYNTHESIS AND IN-SITU HETEROCYCLIC N-NITRATION
Adams, Christopher M.,Sharts, Clay M.,Shackelford, Scott A.
, p. 6669 - 6672 (1993)
Keywords: Anhydrous Nitration, Nitronium Triflate, Tetrabutylammonium Nitrate, Triflic Anhydride Reaction of tetra-n-butylammonium nitrate and triflic anhydride, CF3SO2OSO2CF3 (Tf2O), in dichloromethane (CH2Cl2) solvent at 0 degrees C, produces anhydrous nitronium nitrate, NO2OSO2CF3 (NO2OTf).Subsequent introduction of various heterocycles and their N-acetylated analogs yield N-nitrated products in 20-76 percent yield with an overall one-pot procedure.
Investigation of Ethylenedinitramine as a Versatile Building Block in Energetic Salts, Cocrystals, and Coordination Compounds
Gruhne, Michael S.,Lommel, Marcus,Wurzenberger, Maximilian H. H.,Klap?tke, Thomas M.,Stierstorfer, J?rg
, p. 4816 - 4828 (2021)
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
Roodt, Gerhard T.,Uprety, Bhawna,Levendis, Demetrius C.,Arderne, Charmaine
, p. 54 - 60 (2019)
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.
Bis(hydrazinium) N,N′-dinitroethylenediaminate(2-)
Bircher,Ochsenbein,Hauser,Burgi
, p. 2002 - 2004 (1996)
The title compound, 2N2H5+ .C2H2N4O42-, is an inherently insensitive high-energy material. The anion has Ci symmetry and is almost planar. The nitrate groups are asymmetric, with a mean nitrate N - O distance longer than that found in N,N′-dinitroethylenediamine and an N1 - N2 distance close to a double-bond value.
Nitration of carbonic, sulfuric and oxalic acid-derived amides in liquid carbon dioxide
Kuchurov, Ilya V.,Fomenkov, Igor V.,Zlotin, Sergei G.,Tartakovsky, Vladimir A.
, p. 81 - 83 (2013/05/08)
N-Nitro- and N,N'-dinitroamides of carbonic, sulfuric and oxalic acids have been prepared in 76-99% yield by the nitration of the corresponding amides with dinitrogen pentoxide in liquid carbon dioxide.
1-Nitroimidazolidin-2-one and its hydrolysis to 1-amino-2-nitroaminoethane
Astakhov,Stepanov,Kruglyakova,Kekin
, p. 575 - 576 (2007/10/03)
A simple procedure for 1-amino-2-nitroaminoethane preparation consisting in nitration of 2-imidasolidinone into mononitro derivative with subsequent hydrolysis was developed. The hydrolysis process was studied by spectrophotometric and volumetric methods.
A Convenient Method For N-Nitration Using Ammonium Nitrate/Trifluoroacetic Anhydride
Suri, Suresh Chander,Chapman, Robert D.
, p. 743 - 745 (2007/10/02)
A mixture of ammonium nitrate and trifluoroacetic anhydride is found to be a convenient reagent for N-nitration in the synthesis of nitramines, nitramides, and nitrimides.Yields are comparable to those from conventional, but less convenient or safe, nitrating reagents.
