Polyfunctional Energetic Nitrates Derived from Tris(hydroxymethyl)aminomethane (Tris)

Abstract

A variety of new energetic compounds were synthesized with the tris(hydroxymethyl)aminomethane (Tris) moiety as a building block. The new nitrates were fully characterized, with use of multinuclear NMR spectroscopy, vibrational analysis, mass spectrometry, differential scanning calorimetry, and elemental analysis. The structure of each compound was confirmed by single‐crystal X‐ray diffraction. The energies of formation were calculated with the Gaussian program package, and the detonation parameters were predicted by using the EXPLO5 computer code. Because of the positive oxygen balance (ΩCO) of the presented compounds, their performance data as oxidizers were compared to the common oxidizer ammonium perchlorate.

1,3,4‐Oxadiazole Bridges: A Strategy to Improve Energetics at the Molecular Level

“…Common ways to modify heterocycles at the molecular scale,i ncluding the introduction of various explosophores, such as nitro,d initromethyl, and trinitromethyl, and amino groups. [14][15][16][17] In addition, the introduction of abridge between two energetic units has been shown to have adramatic effect on performance.A ss een in Figure 1, the bridge is mainly afunctional group such as carbonyl, ethylene,azo,and azoxy. and bis(3-nitro-1-(trinitromethyl)-1H-1,2,4-triazol-5-yl)methanone (B), [19] which have acarbonyl group introduced into the conjugated system, show better stability (T d !…”

1,3,4‐Oxadiazole Bridges: A Strategy to Improve Energetics at the Molecular Level

“…Common ways to modify heterocycles at the molecular scale,i ncluding the introduction of various explosophores, such as nitro,d initromethyl, and trinitromethyl, and amino groups. [14][15][16][17] In addition, the introduction of abridge between two energetic units has been shown to have adramatic effect on performance.A ss een in Figure 1, the bridge is mainly afunctional group such as carbonyl, ethylene,azo,and azoxy. Bis(5-(trinitromethyl)-1,3,4-oxadiazol-2-yl)methanone (A) [18] Figure 1.…”

“…Common ways to modify heterocycles at the molecular scale, including the introduction of various explosophores, such as nitro, dinitromethyl, and trinitromethyl, and amino groups [14–17] . In addition, the introduction of a bridge between two energetic units has been shown to have a dramatic effect on performance.…”

Oxygen-Rich Bis(trinitroethyl esters): Suitable Oxidizers as Potential Ammonium Perchlorate Replacements

“…In recent years, several functional groups for HEDOs were investigated, for example, the very toxic fluorodinitromethyl moiety with excellent performance, 6,7 trinitroalkyl compounds, with great performance data and low thermal stability, 8,9 as well as organic nitrates, which are often easily accessed from the corresponding alcohol but can suffer from long-term stability issues. 10,11 Nitrocarbamates are also obtained from alcohols and form a more recently developed class of energetic materials, tending to have lower sensitivities, higher thermal stabilities, and just slightly lower performance as shown by the pentaerythritol derivatives, the tetranitrate (PETN) and the tetranitrocarbamate (PETNC). 12,13 Apart from aliphatic building blocks, oxadiazoles are a choice to combine a nitrogen-and oxygen-containing ring, which possesses usually a high density, with various oxygen-containing moieties.…”