Synthesis and Characterization of Salts of the 3,6‐Dinitro‐[1,2,4]triazolo[4,3‐b][1,2,4]triazolate Anion: Insensitive Energetic Materials Available From Economical Precursors

Abstract

In this work, the treatment of 3,6,7-triamino- [1,2,4]triazolo[4,3-b][1,2,4]triazole (TATOT) [1] with sulfuric acid and sodium nitrite results in elimination of the N-amine and the formation of the new energetic anion 3,6-dinitro-[1,2,4]triazolo[4,3-b][1,2,4]triazolate (DNTT) via nitro-Sandmeyer chemistry. This new energetic anion is available in a convenient and inexpensive three-step process from in-1197 expensive commercial starting materials. Several nitrogen rich salts of this material have been prepared and their chemical (infrared, Raman, NMR, single-crystal X-ray) and energetic (impact, friction, thermal) properties determined. As a rule, this class of energetic salts are insensitive energetic materials.Scheme 2. Synthesis of DNTT salts 2-4 from 1.

Tetrazole Azasydnone (C2N7O2H) And Its Salts: High‐Performing Zwitterionic Energetic Materials Containing A Unique Explosophore

“…High-nitrogen heterocyclesm ake up the backboneo fm any energetic materials. [6][7][8] Heterocycles such as tetrazoles, [9,10] tetrazines, [11][12][13][14] triazoles [15][16][17] and triazines [18,19] have all found extensiveu se in the design of new energetic materials. Their nitrogen contentc ontributes to the energetic properties of [a] M. L. Gettings these materials due to high heats of formation as ar esult of the thermodynamic driving force of nitrogenous compounds towardst he formation of nitrogen gas.…”

Titanium Superoxide for the Oxidation of Amines: Synthesis of bis(3‐nitro‐1H‐1,2,4‐triazol‐5‐yl)methane and its Metal Salts

“…The method we employed (Scheme 1. Method A) was based on a modification of the synthesis for silver 3,6‐dinitro‐[1,2,4]triazolo[4,3‐b][1,2,4]triazolate [15] . A solution of DABTM in water and 20 % sulfuric acid was added dropwise to a solution of sodium nitrite while maintaining a temperature between 60 and 70 °C.…”

“…Method A) was based on a modification of the synthesis for silver 3,6-dinitro- [1,2,4]triazolo [4,3b] [1,2,4]triazolate. [15] A solution of DABTM in water and 20 % sulfuric acid was added dropwise to a solution of sodium nitrite while maintaining a temperature between 60 and 70 °C. The combined mixture was then stirred for 2 hours at temperature before being subsequently cooled, acidified, and extracted with ethyl acetate.…”

Sensitive Energetics from the N‐Amination of 4‐Nitro‐1,2,3‐Triazole

“…Within the field of energetic materials, the development of new explosives possessing high performance and high stability is a major goal . Unfortunately, many examples exist suggesting that high performance and high stability are often mutually exclusive.…”

“…Within the field of energetic materials, the development of new explosives possessing high performance and high stability is a major goal. [1][2][3][4][5][6][7] Unfortunately, many examples exist suggesting that high performance and high stability are often mutually exclusive. There are three main ways to impart explosive energy content to an energetic molecule; the incorporation of fuel and oxidizer in the same molecule (as seen in traditional energetics such as RDX and PETN), creating compounds possessing ring or cage strain, and incorporating large amounts of nitrogen to give rise to high heats of formation.…”