Environmental issues in the synthesis and purification of 5-nitrotetrazole sodium salt

Ilyushin, M. A.; Smirnov, A. V.; Андреев, В. Н.; Целинский, И. В.; Шугалей, И. В.; Нестерова, О. В.

doi:10.1134/s1070363215130034

Cited by 11 publications

(6 citation statements)

References 10 publications

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“…Complex synthesis. NCP complex was synthesized through the interaction of cobalt aquapentaamminate with sodium 5nitrotetrazolate [30][31][32][33] in an acidic media for three hours at elevated temperature. [34] The properties of the obtained NCP complex corresponded to those given in the works.…”

Section: Methodsmentioning

confidence: 99%

Laser initiation of modified complex cobalt (III) perchlorate

Ilyushin

Voznyakovskii

Шугалей

et al. 2021

Zeitschrift anorg allge chemie

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The article presents the results of quantum-chemical calculations of an isolated molecule of pentaammine-(5-nitro-2Htetrazolato-N 2 )cobalt (III) perchlorate (complex 1, NCP) and the products of its possible primary decomposition stage. Using Quantum chemical calculations in the approximation of the density functional theory, it was shown that the decomposition of complex 1 probably starts with the destruction of the 5nitrotetrazole ligand and the elimination of the nitrogen molecule, but not with the elimination of the coordinated ammonia molecule from the inner sphere of the cobalt complex. The likelihood of this mechanism increases with the addition of highly conductive nanocarbon additives. The effect of the addition of multilayer graphene additives on the interaction of laser radiation with the above complex has been examined in detail, and two variants of mechanisms for this effect have been identified. A real model of a laser detonator based on the experimental data, has been created.

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Section: Methodsmentioning

confidence: 99%

Laser initiation of modified complex cobalt (III) perchlorate

Ilyushin

Voznyakovskii

Шугалей

et al. 2021

Zeitschrift anorg allge chemie

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“…We have personally watched an undisturbed reaction begin the process of microdetonations in the absence of any external stimuli. The phenomenon was first described as “explosiveness” by von Herz, “minor detonations” by Gilligan and Kamlet and more recently as microexplosions or microdetonations. − The phenomenon would lead to audible snapping within the reactor vessel and, in some cases, glass fracture . The von Herz synthesis also required filtration of the sensitive acidic intermediate hydronium copper(II)-tris(5-nitrotetrazolate) trihydrate ([H 3 O][Cu(NT) 3 ·3H 2 O]), often colloquially referred to as the “acid salt”. ,,, Another method of synthesis was proposed by Koldobskii and Ostrovskii et al in which a Sandmeyer reaction was conducted without a copper sulfate “catalyst”, avoiding isolation of copper(II)-tris(5-nitrotetrazolate) trihydrate.…”

Section: Introductionmentioning

confidence: 99%

“…Complete elimination of microdetonations was attempted but led to sodium nitrite and other impurities in the NaNT product, making it unsuitable for synthesizing DBX-1 . Other suggested improvements were the use of flow reactors to further reduce microdetonation risk and utilizing an absorption/desorption technique to isolate NaNT without risk associated with isolating its sensitive anhydrous salt . Recently, Salan et al proposed a synthesis method of NaNT utilizing a “catch and release” catalyst which would stabilize the diazonium tetrazolate salt intermediate until it was oxidized to NaNT and thereupon be “released” from the catalyst.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 5-Nitrotetrazolate via the Aqueous Oxidation of 5-Aminotetrazole

Zuckerman

Manship

Smith

et al. 2022

Org. Process Res. Dev.

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The preparation of the important energetic precursor sodium nitrotetrazolate has long been plagued by safety and purity problems. The prevailing synthesis methods utilizing the Sandmeyer reaction proceed via sensitive, explosive intermediates and would be classified as a high-hazard process. In this work, we directly oxidize precursor 5-aminotetrazole to 5-nitrotetrazole in aqueous solution utilizing a heterogeneous titanium superoxide catalyst, skipping the sensitive intermediates inherent in the current industrial Sandmeyer route and providing a vastly safer process with a yield of 50−65%. The prepared sodium nitrotetrazole is of high purity and therefore is directly useful in the synthesis of the primary explosive DBX-1, which is a synthesis that is highly sensitive to impurities. The improved safety and excellent product purity demonstrates the superiority of our route.

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“…Fronabarger and Williams suggested limiting the danger of microdetonations by conducting synthesis in a continuous flow or microreactors as opposed to batch reaction . Ilyushin et al . suggested an alternative workup method in which the NaNT product was absorbed by a microporous absorbent and desorbed into the desired medium of the next reaction.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 5‐Nitrotetrazolates by the Direct Oxidation of 5‐Aminotetrazole in a Single‐Pot Synthesis without Isolation of Explosive Intermediates

2020

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A readily available oxidizer, potassium superoxide can be used for the oxidation of 5-amino-1H-tetrazole (5-AT) to 5-nitrotetrazole (5-NT) in high yields in a single-pot synthesis. This strategy reduces the synthesis of this important energetic material down to a single step and eliminates highly sensitive diazonium and copper salt primary explosive intermediates. Use of dimethyl sulfoxide along with molecular sieves and 18crown-6 as phase transfer catalyst promoted faster reaction rates and greater yield. The overall yield of this process is 48-53 % and the resultant aqueous solution of product was effectively used for the preparation of nitrotetrazole-containing primary explosive DBX-1. Unlike current methods of nitrotetrazole preparation, this entirely solution-based route results in a final solution of sodium nitrotetrazolate, without the need to handle energetic intermediates or products, making it the safest method of nitrotetrazole preparation reported to date.

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Environmental issues in the synthesis and purification of 5-nitrotetrazole sodium salt

Cited by 11 publications

References 10 publications

Laser initiation of modified complex cobalt (III) perchlorate

Laser initiation of modified complex cobalt (III) perchlorate

Synthesis of 5-Nitrotetrazolate via the Aqueous Oxidation of 5-Aminotetrazole

Synthesis of 5‐Nitrotetrazolates by the Direct Oxidation of 5‐Aminotetrazole in a Single‐Pot Synthesis without Isolation of Explosive Intermediates

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