Novel trinitroethanol derivatives: high energetic 2-(2,2,2-trinitroethoxy)-1,3,5-triazines
| Autor: | Vladimir A. Zalomlenkov, Marina I. Struchkova, Victor E. Parfenov, Aleksei B. Sheremetev, Vladimir V. Bakharev, David B. Lempert, Nadezhda V. Palysaeva, Evgeniy V. Yurtaev, Kyrill Yu. Suponitsky, Alexander A. Gidaspov |
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| Rok vydání: | 2016 |
| Předmět: |
010405 organic chemistry
General Chemical Engineering Ether General Chemistry Nuclear magnetic resonance spectroscopy 010402 general chemistry 01 natural sciences 0104 chemical sciences chemistry.chemical_compound Differential scanning calorimetry chemistry Elemental analysis Nucleophilic substitution Moiety Organic chemistry Single crystal Trinitromethane |
| Zdroj: | RSC Advances. 6:34921-34934 |
| ISSN: | 2046-2069 |
| DOI: | 10.1039/c6ra05826d |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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