Issue 49, 2016
From the journal:

Chemical Communications

From FOX-7 to H-FOX to insensitive energetic materials with hypergolic properties†

Dharavath Srinivas,a   Lauren A. Mitchell,b   Damon A. Parrishc  and  Jean'ne M. Shreeve*a  

* Corresponding authors

a Department of Chemistry, University of Idaho, Moscow, USA
E-mail: jshreeve@uidaho.edu
Fax: +1-208-885-9146

b Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA

c Naval Research Laboratory, Code 6030, Washington, D.C. 20375-5001, USA

Abstract

Nitrogen/halogen rich derivatives, 3, 4, 8, and 9 of FOX-7 (1,1-diamino-2,2-dinitroethene), and H-FOX (1-hydrazinyl-2,2-dinitroethenamine) have been synthesized, characterized and found to exhibit good energetic properties. Compound 4 displays hypergolic properties with commonly utilized fuels such as monomethyl hydrazine (MMH), and hydrazine hydrate (HH), as well as with ethylenediamine (EN), and 1,3-diaminopropane (DAP) showing ignition delay times between 2.5 to 10 ms. Additionally, the hypergolic properties of 4 and 8 were further studied by using ammonia borane as a fuel solubilized in a green ionic liquid, 1-allyl-3-methyl imidazolium dicyanamide, (1 : 1 molar ratio). This is a new role for a derivative of H-FOX. The energetic and physical properties of all the molecules were either measured or calculated. All of materials were characterized by NMR, and infrared spectra, elemental analyses, and differential scanning calorimetry. Single crystal X-ray structural measurements for 4 and 9 were helpful in their confirmation.

Graphical abstract: From FOX-7 to H-FOX to insensitive energetic materials with hypergolic properties

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Article information

DOI
https://doi.org/10.1039/C6CC02669A
Article type
Communication
Submitted
30 Mar 2016
Accepted
23 May 2016
First published
23 May 2016

Chem. Commun., 2016,52, 7668-7671

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From FOX-7 to H-FOX to insensitive energetic materials with hypergolic properties

D. Srinivas, L. A. Mitchell, D. A. Parrish and J. M. Shreeve, Chem. Commun., 2016, 52, 7668 DOI: 10.1039/C6CC02669A

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