Novel trinitroethanol derivatives: high energetic 2-(2,2,2-trinitroethoxy)-1,3,5-triazines

Novel trinitroethanol derivatives: high energetic 2-(2,2,2-trinitroethoxy)-1,3,5-triazines Full article

Journal

RSC Advances
ISSN: 2046-2069

Output data

Year: 2016, Volume: 6, Number: 41, Pages: 34921-34934 Pages count : 14 DOI: 10.1039/c6ra05826d

Authors

Gidaspov Alexander A. ¹ , Zalomlenkov Vladimir A. ¹ , Bakharev Vladimir V. ¹ , Parfenov Victor E. ¹ , Yurtaev Evgeniy V. ¹ , Struchkova Marina I. ² , Palysaeva Nadezhda V. ² , Suponitsky Kyrill Yu ³ , Lempert David B. ⁴ , Sheremetev Aleksei B. ²

Affiliations

1	Samara State Technical University, Samara, 443100, Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp, Moscow 119991, Russian Federation
3	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Science, Moscow 119991, Russian Federation
4	Institute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka, Moscow Region, 142432 Russian Federation

The multicomponent reaction of 2,4,6-trichloro-1,3,5-triazine with potassium trinitromethane and trinitroethanol was exploited for the first synthesis of the hetaryl trinitroethyl ether, 2,4-bis(2,2,2-trinitroethoxy)-6-trinitrometyl-1,3,5-triazine 13. The use of compound 13 as a scaffold for the synthesis of substituted trinitroethoxytriazine by sequential nucleophilic substitution processes is described. A number of trinitroethoxytriazines bearing a range of functional groups, including 2,4,6-tris(2,2,2-trinitroethoxy)-1,3,5-triazine 16, have been prepared. There has been no previous incorporation of the trinitroethoxy moiety to a heteroaromatic ring. All trinitroethoxytriazines were fully characterized using IR and multinuclear NMR spectroscopy, elemental analysis, and differential scanning calorimetry (DSC), and, in some cases, 16, 20 and 21, with single crystal X-ray structuring. When compared to the aliphatic trinitroethoxy compounds, the trinitroethoxytriazines show better energetic performance as calculated. The impact sensitivities and ignition points of the novel oxygen and nitrogen-rich triazines were measured. The ability of the applied trinitroethoxytriazines in solid composite propellants as well as in gas generant compositions for airbag inflators was evaluated. The straightforward preparation of these ethers highlights them as valuable new environmentally friendly and high-performing nitrogen and oxygen-rich materials.

Gidaspov A.A. , Zalomlenkov V.A. , Bakharev V.V. , Parfenov V.E. , Yurtaev E.V. , Struchkova M.I. , Palysaeva N.V. , Suponitsky K.Y. , Lempert D.B. , Sheremetev A.B.
Novel trinitroethanol derivatives: high energetic 2-(2,2,2-trinitroethoxy)-1,3,5-triazines
RSC Advances. 2016. V.6. N41. P.34921-34934. DOI: 10.1039/c6ra05826d WOS Scopus OpenAlex

≡ Web of science:	WOS:000374049700099
≡ Scopus:	2-s2.0-84966378438
≡ OpenAlex:	W2329069563