Nitraza‐/Oxa‐Propylene‐ and Hydrazonemethylene‐Bridged 1,2,4‐Nitraminotriazoles and Selected Salts

Harter, Alexander G.; Klapötke, Thomas M.; Krumm, Burkhard; Lechner, Jasmin T.; Riedelsheimer, Christian

doi:10.1002/ejoc.202300302

Cited by 3 publications

(4 citation statements)

References 33 publications

(73 reference statements)

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“…Comparing the sensitivities of the oxa-bridged compounds with those of the nitrazapropane-bridged compounds confirms the results in the literature: [30] 9 to 11 are clearly less sensitive than 1 to 3. The sensitivities of the two ECCs (12 and 13) stand out showing very low values, both of which are in the range of primary explosives, with sensitivities towards impact being classified as very sensitive and towards friction as extremely sensitive.…”

Section: Sensitivities and Energetic Propertiessupporting

confidence: 87%

“…[38] Since the literature suggests that oxapropane-bridged compounds are more stable than nitrazapropane-bridged compounds, the three isomers of oxapropane-bridged tetrazole were also synthesized and compared with the nitraminebridged compounds. [30] The 1,1'-isomer 9 has been mentioned once before in the literature, however, in this work it was prepared via an alternative route and fully characterized for the first time in terms of its energetic properties. [39]…”

Section: Introductionmentioning

confidence: 96%

“…[26][27] In the literature it is reported that bridged energetic materials show a higher stability. [28][29][30] In the previously reported compounds, simple saturated carbon chains have usually been used to act as bridging units, but also oxa, azo or nitramine bridged compounds have been reported. [30][31][32] As is shown on the left side of Figure 1, many compounds with nitrazapropane or trinitrazaheptane as the bridging unit have been reported.…”

Section: Introductionmentioning

confidence: 99%

“…[28][29][30] In the previously reported compounds, simple saturated carbon chains have usually been used to act as bridging units, but also oxa, azo or nitramine bridged compounds have been reported. [30][31][32] As is shown on the left side of Figure 1, many compounds with nitrazapropane or trinitrazaheptane as the bridging unit have been reported. Open-chain nitramine compounds such as the bridged bis-azides or bridged azoles are already known in literature (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Bridged Tetrazoles with Promising Properties and Potential Applications by a One‐Step Finkelstein Reaction

Lechner,

Riedelsheimer,

Endraß

et al. 2023

Chemistry A European J

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Numerous nitramine bridged compounds which show promising combinations of properties have already been identified in the area of energetic materials. In this work, four new nitrazapropane bridged tetrazoles, as well as four new trinitrazaheptane tetrazoles and three oxapropane bridged tetrazoles were synthesized and fully characterized. These new compounds can all be synthesized by a simple, one‐step synthesis using Finkelstein conditions. All of these new energetic materials were characterized using NMR spectroscopy, single crystal X‐ray diffraction, vibrational analysis and elemental analysis. The thermal behaviour of these compounds was studied by differential thermal analysis (DTA) and partly by thermogravimetric analysis (TGA). The BAM standard method was used to determine the sensitivities towards impact (IS) and friction (FS). The enthalpies of formation were calculated at the CBS‐4M level, and the energetic performances were calculated using the EXPLO5 (V6.06.01) computer code. The properties of the new compounds were compared to each other as well as to the known energetic material RDX. Moreover, the iron(II) and copper(II) perchlorate complexes with 1,3‐bis‐1,1‐tetrazolylnitrazapropane as ligand were prepared and investigated.

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Section: Sensitivities and Energetic Propertiessupporting

confidence: 87%

Section: Introductionmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of Bridged Tetrazoles with Promising Properties and Potential Applications by a One‐Step Finkelstein Reaction

Lechner,

Riedelsheimer,

Endraß

et al. 2023

Chemistry A European J

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Investigation and Characterization of Nitrazapropane‐, Oxapropane‐ and Trinitrazaheptane‐Bridged Nitro Esters

Lechner,

Riedelsheimer,

Gerold

et al. 2023

Eur J Org Chem

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In this work, 1,3‐dinitroxy‐2‐nitrazapropane and 1,7‐dinitroxy‐2,4,6‐trinitrazaheptane were synthesized and investigated. Starting from hexamine, the open‐chain compounds were prepared by a modified Bachmann procedure which is commonly used for the synthesis of hexogen (RDX) and octogen (HMX). All new compounds were characterized by NMR spectroscopy, X‐ray diffraction, vibrational analysis and elemental analysis. Their thermal behavior was studied by differential thermal analysis (DTA) and thermogravimetric analysis (TGA). The sensitivities towards impact (IS) and friction (FS) were determined according to the BAM (Bundesanstalt für Materialforschung und ‐prüfung) standard method. Their energetic properties, which were determined from the energies of formation at the CBS‐4 M level, were calculated using the EXPLO5 computer code. Moreover, 1,3‐dinitroxy‐2‐oxapropane was synthesized and investigated. The various compounds were compared with each other and with the commonly used explosives in terms of their physicochemical properties and detonation behavior.

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Trinitroethyl hydrazides of dicarbonic acids – Energetic compounds with high oxygen and nitrogen content

Klapötke,

Krumm,

Riedelsheimer

2024

Propellants Explo Pyrotec

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Many currently used energetic materials need to be replaced with new compounds due to toxicity or other drawbacks. Among these is the oxidizer ammonium perchlorate, often used in solid state propellants, which itself, as well as its combustion products, poses health and environmental issues. Herein, three new polynitro energetic compounds are presented containing trinitroethyl moieties. Starting from easily available starting materials, such as malonic acid ethylester, diglycolic and diaminodiacetic acid, simple and straightforward syntheses were performed to obtain first the corresponding hydrazides and subsequently the trinitroethyl hydrazides in good yields and high purity. These compounds have a positive oxygen balance (assuming to the formation of CO), a high oxygen and nitrogen content and moderate densities. Full characterization was performed by NMR spectroscopy, vibrational analysis and elemental analysis. By using the Gaussian program package, the heats of formation were calculated and the energetic parameters were estimated utilizing the EXPLO5 computer code.

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Nitraza‐/Oxa‐Propylene‐ and Hydrazonemethylene‐Bridged 1,2,4‐Nitraminotriazoles and Selected Salts

Cited by 3 publications

References 33 publications

Synthesis of Bridged Tetrazoles with Promising Properties and Potential Applications by a One‐Step Finkelstein Reaction

Synthesis of Bridged Tetrazoles with Promising Properties and Potential Applications by a One‐Step Finkelstein Reaction

Investigation and Characterization of Nitrazapropane‐, Oxapropane‐ and Trinitrazaheptane‐Bridged Nitro Esters

Trinitroethyl hydrazides of dicarbonic acids – Energetic compounds with high oxygen and nitrogen content

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