Synthesis of New Energetic Materials Based on Furazan Rings and Nitro‐NNO‐azoxy Groups

Synthesis of New Energetic Materials Based on Furazan Rings and Nitro‐NNO‐azoxy Groups Full article

Journal

ChemistrySelect
ISSN: 2365-6549

Output data

Year: 2020, Volume: 5, Number: 39, Pages: 12243-12249 Pages count : 7 DOI: 10.1002/slct.202003182

Authors

Leonov Nikita E. ¹ , Klenov Michael S. ¹ , Anikin Oleg V. ¹ , Churakov Aleksandr M. ¹ , Strelenko Yurii A. ¹ , Voronin Alexey A. ¹ , Lempert David B. ² , Muravyev Nikita V. ³ , Fedyanin Ivan V. ^4,5 , Semenov Sergei E. ^6,1 , Tartakovsky Vladimir A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences 47 Leninsky prosp., 119991 Moscow, Russian Federation
2	Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 Academician Semenov avenue, 142432 Chernogolovka, Moscow region, Russian Federation
3	Semenov Institute of Chemical Physics, Russian Academy of Sciences, 4 Kosygina Street, Building 1, 119991 Moscow, Russian Federation
4	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova Street, 119991 Moscow, Russian Federation
5	Plekhanov Russian University of Economics, Stremyanny per. 36, 117997 Moscow, Russian Federation
6	Moscow Chemical Lyceum 4 Tamozhenniy proezd, 111033 Moscow, Russian Federation

Energetic compounds 1–6, consisting of one or two furazan rings linked by azo or azoxy bridges and one or two nitro-NNO-azoxy substituents, were synthesized by nitration of the corresponding tert-butyl-NNO-azoxy precursors with NO2BF4. Novel methods for the synthesis of 3,4-bis(tert-butyl-NNO-azoxy)furazan (7) and bis-4,4′-(tert-butyl-NNO-azoxy)-3,3′-azoxyfurazan (21) were elaborated. The nitro-NNO-azoxy compounds obtained display high calculated detonation performance (vD=8.07–9.40 km s−1 and PC-J=27.4–43.4 GPa) that is superior to the corresponding nitrofurazans (DNF, DNAzF, DNAF). The replacement of nitrofurazans with the corresponding (nitro-NNO-azoxy)furazans increases the specific impulse of the model solid composite propellant formulations by 2–10 s, which is due to high calculated heats of formation (600–892 kcal kg−1) and positive oxygen balance (0–20 %) of the latter compounds.

Leonov N.E. , Klenov M.S. , Anikin O.V. , Churakov A.M. , Strelenko Y.A. , Voronin A.A. , Lempert D.B. , Muravyev N.V. , Fedyanin I.V. , Semenov S.E. , Tartakovsky V.A.
Synthesis of New Energetic Materials Based on Furazan Rings and Nitro‐NNO‐azoxy Groups
ChemistrySelect. 2020. V.5. N39. P.12243-12249. DOI: 10.1002/slct.202003182 WOS Scopus OpenAlex

≡ Web of science:	WOS:000580579000026
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