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[(3-Nitro-1H-1,2,4-triazol-1-yl)-NNO-azoxy]furazans: energetic materials containing an N(O)N–N fragment Научная публикация

Журнал RSC Advances
ISSN: 2046-2069
Вых. Данные Год: 2021, Том: 11, Номер: 39, Страницы: 24013-24021 Страниц : 9 DOI: 10.1039/d1ra03919a
Авторы Gulyaev Dmitry A. 1 , Klenov Michael S. 1 , Churakov Aleksandr M. 1 , Strelenko Yurii A. 1 , Fedyanin Ivan V. 2,3 , Lempert David B. 4 , Kosareva Ekaterina K. 5 , Kon’kova Tatiana S. 5 , Matyushin Yurii N. 5 , Tartakovsky Vladimir A. 1
Организации
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 Plekhanov Russian University of Economics, Moscow 117997, Russian Federation
4 Institute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka, Moscow region 142432, Russian Federation
5 N. N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, Moscow 119991, Russian Federation

Реферат: The strategy for the synthesis of substituted [(3-nitro-1H-1,2,4-triazol-1-yl)-NNO-azoxy]furazans 4–7, in which the distal nitrogen of the azoxy group is bonded to the nitrogen atom of the azole ring, includes, firstly, the reaction of 1-amino-3-nitro-1H-1,2,4-triazole with 2,2,2-trifluoro-N-(4-nitrosofurazan-3-yl)acetamide in the presence of dibromisocyanuric acid followed by removing of the trifluoroacetyl protecting group to afford aminofurazan (4). Transformation of the amino group in the latter made it possible to synthesize the corresponding nitro (5), azo (6), and methylene dinitramine (7) substituted furazans. The compounds synthesized are thermally stable (decomposition onset temperatures 147–228 °C), exhibit acceptable densities (1.77–1.80 g cm−3) and optimal oxygen balance (the oxidizer excess coefficients α = 0.42–0.71). Their standard enthalpies of formation (576–747 kcal kg−1) were determined experimentally by combustion calorimetry and these compounds have been estimated as potential components of solid composite propellants. In terms of the specific impulse level, model solid composite propellant formulations based on nitro and methylene dinitramine substituted furazans 5 and 7 outperform similar formulations based on CL-20 by 1–4 s, and formulations based on HMX and RDX by 5–8 s.
Библиографическая ссылка: Gulyaev D.A. , Klenov M.S. , Churakov A.M. , Strelenko Y.A. , Fedyanin I.V. , Lempert D.B. , Kosareva E.K. , Kon’kova T.S. , Matyushin Y.N. , Tartakovsky V.A.
[(3-Nitro-1H-1,2,4-triazol-1-yl)-NNO-azoxy]furazans: energetic materials containing an N(O)N–N fragment
RSC Advances. 2021. V.11. N39. P.24013-24021. DOI: 10.1039/d1ra03919a WOS Scopus OpenAlex
Идентификаторы БД:
≡ Web of science: WOS:000678301300017
≡ Scopus: 2-s2.0-85111083591
≡ OpenAlex: W3210465576
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