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121-82-4Relevant articles and documents
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Bachmann et al.
, p. 2769,2771 (1951)
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Berman et al.
, p. 767,775 (1951)
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15N STUDIES OF THE MECHANISMS OF NITRATOIN OF HEXAMETHYLENETETRAMINE AND 3,7-DIACETYL-1,2,5,7-TETRAAZABICYCLONONANE
Crampton, Michael R.,Jones, Michael,Scranage, John K.,Golding, Peter
, p. 1679 - 1684 (1988)
Mechanistic studies of the nitration of hexamethylenetetramine (1) and some derivatives are reported and are compared with acetylation reactions.Nitration reactions, with nitric acid, were carried out using mixtures of - and -compounds and the destination of the nitrogen-isotopes in the products was determined mass spectrometrically.The results show that in nitration of (1) to give 3,7-dinitro-1,3,5,7-tetraazabicyclononane (DPT) extensive ring cleavage occurs to give species containing single amino-nitrogen fragments.Howover the nitration of 3,7-diacetyl- 1,3,5,7-tetraazabicyclononane to 1,5-diacetyl-3,7-dinitro-1,3,5,7-tetraazacyclooctane (DADN) involves selective cleavage of the methylene bridge.A synthesis of DADN by acetolysis of DPT is reported.
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Bachmann,Jenner
, p. 2773 (1951)
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An efficient and solvent-free method to synthesize HMX by nitrolysis of DPT catalyzed by reusable solid acid catalysts
Shaghayeghi Toosi, Foad,Jadidoleslami, Mahdi
, p. 159 - 162 (2016)
Direct nitrolysis of 3,7-dinitro-1,3,5,7-tetraazabicyclo[3,3,1]nonane (DPT) is a feasible way to synthesize HMX, which is one of the most powerful explosives. A new nitrolysis process involving the use of nitric acid and various solid acid catalysts such as silica sulfuric acid, heteropoly acids, and metal nitrates was used as an effective and safe nitrating agents for the nitration of DPT to HMX under mild and heterogeneous conditions with good yields. In order to optimize the process, the reactions were carried out with a varying amount of catalysts and also the catalysts were efficiently recovered.
Investigation of the effect of metallic lewis acid on the nitrolysis of [3,7-diacetyl-1,3,5,7-tetraazabicyclo(3.3.1)-nonane] and hexamine
Shi, Liangwei,Yu, Menglong,Zhang, Yazhu,Qin, Guangming,Lue, Jian,Zhao, Gang
, p. 283 - 287 (2011)
The effect of metallic ions on the nitrolysis of DAPT [3,7-diacetyl-1,3,5, 7-tetraazabicyclo(3.3.1)nonane] and HA (hexamine) was investigated by experimental and theoretical approaches. The combinatorial reagent, M(NO -3)n/Ac2/NH4NO 3 (M=Mg2+, Cu2+, Pb2+, Bi 3+, Fe3+ and Zr4+), was found to be efficient in the experiment of the nitrolysis of DAPT. A key intermediate during the nitrolysis of DAPT was detected by 1H NMR. The formation mechanism of the intermediate was proposed and analyzed. Some discrepant results for the nitrolysis of DAPT and HA catalyzed by different metallic nitrates were explained based on hard-soft and acid-base principle and stabilized energy of ion-complex. From the latter point of view, some cations with high polarizable ligands, e.g., OSO2CF3-, (CF3SO 2)2N-, and (C4F9SO 2)2N-, can increase the yields. Two newly designed catalysts, Cu[(CF3SO2)2N]2 and Cu[(C4F9SO2)2N]2, were tested to be highly efficient. Copyright
Synthesis and characterization of guanidinium difluoroiodate, [C(NH 2)3]+[IF2O2]- and its evaluation as an ingredient in agent defeat weapons
Fischer, Dennis,Klapoetke, Thomas M.,Stierstorfer, Joerg
, p. 660 - 665 (2011)
Ammonium and guanidinium difluoroiodate(V), [NH4] +[IF2O2]- (1a) and [C(NH 2)3]+[IF2O2]- (1b), and diazidoglyoxime, [N3C=N-OH]2 (2) were synthesized and the molecular structures in the solid state of 1b and 2 were elucidated by single-crystal X-ray diffraction. 1b: P1, a = 6.6890(5), b = 10.2880(6), c = 10.30.92(8) A, α = 105.447(6), β = 108.568(7), γ = 91.051(5)°, V = 644.08(8) A3, P = 2.650 g·cm-3; 2: P21/n, a = 4.4211(3), b = 13.7797(9), c = 4.9750(3) A, β = 98.735(6), V = 299.57(3) A3, P = 1.886 g·cm-3. The suitability of compounds 1a and 1b as active ingredients for agent defeat weapons (ADW) with biocidal activity has been shown in detonation tests using geobacillus stearothermophilus spores. In addition, a complete energetic characterization of the promising primary explosive 2 is given.
Novel Method for Directly Nitration of OH-, SH-and NHR-Functions in Organic Molecules by Means of in Situ Generated Carbonic Acid Dinitrate
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Page/Page column 3, (2012/09/22)
The invention relates to a nitration method having the following principles: a phosgene species is converted with two equivalent silver nitrates into a double-mixed anhydride of carbonic acid and nitric acid, known here as carbonic acid dinitrate (I). Said operation is carried out in situ, and the formed dinitrate decomposes spontaneously. In addition to carbon dioxide, nitrate ions and nitronium ions are formed, said ions comprising electrophiles which are necessary for nitration. The solution which is used is acetonitrile, and is insignificant if the alcohol species is dissolved or suspended. The necessary equivalent silver nitrates are introduced into the system and optionally heated or cooled to the desired temperature. Subsequently, the acid chloride is introduced slowly, drop by drop or slowly little by little. Phosgene, diphosgene, triphosgene and chloroformic acid ester can be used as carbonic acid dichloride and monochloride, and their thiocarbonic acid analogues. A brown colouration and precipitated silver chloride display the formation of the carbonic acid reactants, said brown colouration rapidly discolouring due to an immediate reaction of the nitronium ions with the substrate with is to be nitrated. Towards the end of the addition of phosgene, the brown colouration remains for longer and longer until it no longer disappears. Then, it is stirred for another hour at room temperature. In the event of high acid-sensitive educts, non-nucleophilic nitrogen bases such as DBU can be added to the system in order to intercept the formation of nitric acid.