4185-47-1Relevant articles and documents
Synthesis, Optimization, and Thermal Risk Analysis of One-Pot N-Nitrodiethanolamine Dinitrate Synthesis
Li, Wei,Feng, Wei,Hao, Jie,Guo, Zichao,Chen, Liping,Chen, Wanghua
, p. 2388 - 2393 (2019)
N-Nitrodiethanolamine dinitrate (DINA) is a nitramine explosive containing both O-nitro and N-nitro groups. In this work, the synthesis of DINA by nitration of diethanolamine hydrochloride (DEAHC) with the fuming nitric acid/acetic anhydride (HNO3/Ac2O) system was developed and optimized. It was found that large amounts of acetic anhydride and low reaction temperature are favorable to the yield of DINA. When the DEAHC:HNO3:Ac2O molar ratio was 1:4.5:6 and the initial reaction temperature was decreased to 5 °C, the yield of DINA reached a?92%. The thermal risk of this synthesis route was also analyzed. The value of TD24 for the final reaction mixture was calculated to be 61.9 °C, which is significantly higher than the MTSR for the synthesis process. This indicates that as long as the addition immediately stops in case of the cooling failure scenario, decomposition of the formed DINA will not occur. The above analysis shows that the DINA synthesis approach reported here is favorable in terms of both productivity and safety.
Positive Electron Impact and Chemical Ionization Mass Spectra of Some Nitramine Nitrates
Rowley, J. A.
, p. 997 - 1000 (1989)
The positive electron impact (EI) and isobutane chemical ionization (CI) mass spectra of six nitramine nitrates were studied with the aid of some accurate mass measurements.In the EI spectra, β fission relative to both the nitramine and nitrate ester is important.In the CI spectra a major ion occurs at + and was found to be mainly due to +.All of the compounds except N-(2 hydroxyethyl)-N-(2',4',6'-trinitrophenyl)nitramine nitrate gave an + ion.The + ion in the isobutane CI mass spectra of tetryl is also due to +.
Experiment and Simulations for the Thermal Safety of the Nitration Reaction Liquid of the Final State in the Synthesis Process ofN-Nitrodihydroxyethyl Dinitrate (DINA)
An, Jing,Chang, Hai,Ding, Li,Wang, Xiaofeng,Zhou, Jing,Zhu, Yanlong
, p. 2110 - 2118 (2021/09/18)
In the synthesis process ofN-nitrodihydroxyethyl dinitrate (DINA) with the HNO3-Mg(NO3)2method, the thermal stability of the nitration reaction liquid of the final state is poor, which leads to the thermal runaway of the entire reaction system easily. The research on the thermal runaway reaction under actual reaction conditions indicates high consumption and high risk. In this article, thermal decomposition behavior and isothermal thermal decomposition kinetics of the nitration reaction liquid of the final state in the synthesis process of DINA were investigated by differential scanning calorimetry (DSC) and microcalorimetry. The mechanism of the stability of the nitration reaction liquid was explored. The thermal safety of the material in a large-scale reactor was simulated and predicted by a thermal simulation software on the basis of kinetic parameters including activation energy, pre-exponential factors, and mechanistic functions. These findings not only avoid the risk and consumption of large-size materials but also guide their application in process optimization, inherent safety design, and handling.
Synthetic method of diethanol nitramine dinitrate
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Paragraph 0036; 0037; 0038, (2020/10/21)
The invention relates to a synthetic method of diethanol nitramine dinitrate. The method comprises the following steps: adding acetic anhydride containing a small amount of fuming nitric acid I into areaction kettle as a backing material, simultaneously adding diethanol amine hydrochloride and fuming nitric acid II at a certain reaction temperature, heating to carry out heat preservation reactionafter the feeding is finished, and finally cooling and washing the reaction product, carrying out suction filtration and drying the reaction product to obtain the final product. The method is high inreaction speed and uniform in heat release, and the synthesis process is easy to control; the product diethanol nitramine dinitrate is synthesized in one step, so that the reaction efficiency is improved; in the product synthesis process, the existence time of the unstable intermediate in the reaction system is short, so that the unstable intermediate can be quickly converted into diethanol nitramine dinitrate, and compared with a magnesium nitrate synthesis method, the safety is obviously improved.
Clean nitrations: Novel syntheses of nitramines and nitrate esters by nitrodesilylation reactions using dinitrogen pentoxide (N2O5)
Millar, Ross W.,Philbin, Simon P.
, p. 4371 - 4386 (2007/10/03)
In this novel nitration method dinitrogen pentoxide (N2O5) in an inert solvent is used as the nitrating agent, thereby removing the need for strong acids as the reaction medium. The N2O5 cleaves heteroatom-silicon bonds, in silylamines and silyl ethers respectively, to yield the desired energetic groupings (nitramines or nitrate esters respectively) without liberation of acids which would occur with conventional substrates (amines or alcohols). These nitrodesilylation reactions proceed cleanly and in good yield, and the scope of the reaction is illustrated by 29 examples, some of which produce high energy compounds, notably plasticisers and an energetic polymer precursor. These reactions are therefore potentially clean nitrations for the manufacture of energetic compounds which will minimise the impact of this activity on the environment in the future.
Synthesis of β-nitroxyalkylnitramines
Tanakovsky,Ermakov,Vinogradov,Sigai
, p. 1024 - 1025 (2007/10/03)
β-Nitroxyalkylnitramines were obtained by nitration of β-hydroxyalkyl sulfamates, products of the condensation of derivatives of sulfamic acid with alkene oxides, by a mixture of HNO3 and H2SO4.
Preparation of Nitramine-Nitrates by Ring-Opening Nitration of Aziridines by Dinitrogen Pentoxide (N2O5)
Golding, Peter,Millar, Ross W,Paul, Norman C,Richards, David H
, p. 7063 - 7076 (2007/10/02)
Thirteen aziridines, bearing various types of substituents on the ring nitrogen, were treated with N2O5 in chlorinated solvents at sub-ambient temperature and formed 1,2-nitramine-nitrate products by a novel ring-opening nitration reaction analogous to that established for the corresponding oxygen heterocycles (epoxides).A wide variety of classes of aziridine underwent the reaction (N-alkyl, N-(nitroaryl), N-acyl and N-imidyl), the yields in many cases being high (70-82percent), although in one category (the N-(alkylcarbonyl)aziridines) competing deacylation reactions resulted in reduced yields.Also, aziridines bearing groups capable of liberating nitric acid with N2O5 (i.e. those with O-H, N-H or unsubstituted aryl groups) gave rise to greatly reduced yields of the nitramine-nitrates owing to competing rections, principally polymerisation/oligomerisation.
