First comprehensive study of energetic (methoxy-NNO-azoxy)furazans: Novel synthetic route, characterization, and property analysis

First comprehensive study of energetic (methoxy-NNO-azoxy)furazans: Novel synthetic route, characterization, and property analysis Full article

Journal

Energetic Materials Frontiers
ISSN: 2666-6472

Output data

Year: 2024, Volume: 6, Number: 3, Pages: 370-382 Pages count : 13 DOI: 10.1016/j.enmf.2024.08.007

Authors

Kulikov Andrey A. ¹ , Leonov Nikita E. ¹ , Klenov Michael S. ¹ , Smirnov Gennady A. ¹ , Strelenko Yurii A. ¹ , Fedyanin Ivan V. ^2,3 , Kon'kova Tatiana S. ⁴ , Matyushin Yurii N. ⁴ , Pivkina Alla N. ⁴ , Tartakovsky Vladimir A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Moscow, 119991, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds Russian Academy of Sciences, Moscow, 119991, Russian Federation
3	HSE University, 101000, Moscow, Russian Federation
4	N. N. Semenov Federal Research Center for Chemical Physics Russian Academy of Sciences, Moscow, 119991, Russian Federation

This paper provides the first in-depth study of energetic methoxy-NNO-azoxy compounds. 3-Amino-4-(methoxy-NNO-azoxy)furazan (7) is a useful precursor to a number of high-enthalpy substituted (methoxy-NNO-azoxy)furazans enriched with explosophoric functionalities (azofurazan 8, nitrofurazan 9, azoxyfurazan 10 and methylene dinitramine 11). It was shown for the first time that the interaction of nitroso compounds with salts of O-substituted N-nitrohydroxylamines leads to the formation of corresponding azoxy-oxy [N(O)=N–O] compounds, as exemplified by the reaction of 3-amino-4-nitrosofurazan (15) with the ammonium salt of O-methyl-N-nitrohydroxylamine (16) to give 3-amino-4-(methoxy-NNO-azoxy)furazan (7). This novel approach turned out to be the most suitable for the multigram synthesis of aminofurazan 7. The resulting (methoxy-NNO-azoxy)furazans 7–11 have good thermal stability (onset decomposition temperatures 148–238 °C), high experimental enthalpies of formation (1435–2750 kJ⋅kg−1) and acceptable densities (1.57–1.75 g⋅cm−3). In terms of detonation performance, all synthesized compounds (detonation velocities D = 7.9–8.5 km⋅s−1, detonation pressures PC–J = 26–32 GPa) lie between 1,3,5-trinitro-1,3,5-triazinane (RDX) (D = 8.9 km⋅s−1, PC–J = 36 GPa) and N-methyl-N-(2,4,6-trinitrophenyl)nitramide (Tetryl) (D = 7.6 km⋅s−1, PC–J = 26 GPa). The sensitivity study was performed and the results were compared to those for prevalent energetic materials. We have shown the extent to which introduction of the methoxy-NNO-azoxy group into a molecule can be used to tune the crucial properties of energetic materials (enthalpy of formation and thermal stability).

Kulikov A.A. , Leonov N.E. , Klenov M.S. , Smirnov G.A. , Strelenko Y.A. , Fedyanin I.V. , Kon'kova T.S. , Matyushin Y.N. , Pivkina A.N. , Tartakovsky V.A.
First comprehensive study of energetic (methoxy-NNO-azoxy)furazans: Novel synthetic route, characterization, and property analysis
Energetic Materials Frontiers. 2024. V.6. N3. P.370-382. DOI: 10.1016/j.enmf.2024.08.007 Scopus OpenAlex

Submitted:	Jun 7, 2024
Accepted:	Aug 28, 2024
Published online:	Aug 31, 2024

≡ Scopus:	2-s2.0-105006939211
≡ OpenAlex:	W4402083445