A New Approach for the Synthesis of 2,3,4а,6,7,8а,9,10-Octaaza-4,8-dioxo-3,4,4a,7,8,8а,9,9a,10,10а-decahydroanthracene and High-Energy Performance Characterization of Its Dinitramide Salt

Author:

Glukhacheva Vera S.1ORCID,Il’yasov Sergey G.1ORCID,Il’yasov Dmitri S.1,Zhukov Egor E.1ORCID,Eltsov Ilia V.2ORCID,Nefedov Andrey A.23

Affiliation:

1. Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences (IPCET SB RAS), Biysk 659322, Russia

2. Department of Natural Sciences, Novosibirsk State University, Novosibirsk 630090, Russia

3. Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences (NIOCh SB RAS), Novosibirsk 630090, Russia

Abstract

A simple, one-pot regioselective method for the synthesis of a high-nitrogen tricycle, 2,3,4а,6,7,8а,9,10-octaaza-4,8-dioxo-3,4,4a,7,8,8а,9,9a,10,10а-decahydroanthracene, with a yield of 27% was developed on a starting urea basis as a result of studies focused on finding new, more efficient approaches to the synthesis of high-energy derivatives of dinitramic acid (DNA). This tricycle was further treated to furnish 2,3,4а,6,7,8а,9,10-octaaza-4,8-dioxo-3,4,4a,7,8,8а,9a,10а-octohydroanthracene-9,10-ion-bis(dinitramide). The resultant salt of dinitramic acid exhibited inhibitory properties towards the burning rate of pyrotechnic compositions, reducing it by 30%, and possessed good thermal stability due to a high decomposition temperature above 260 °C and a low sensitivity to mechanical stimuli. The structural features of the new tricycle-based dinitramide salt were characterized via 2D NMR spectroscopy and double-focusing sector mass spectrometry (DFS).

Funder

Ministry of Science and Higher Education of the Russian Federation

Publisher

MDPI AG

Subject

General Materials Science

Reference36 articles.

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