Nitrogen‐rich Compounds with Multiple Azole Rings: Gas Generant, Enthalpy Enhancer and Applicable Cationic Component

Nitrogen‐rich polyazole derivatives were designed and synthesized from the commercially available 4,5‐dicyano‐2‐aminoimidazole. The relatively simple synthesis of multiple azole rings in desired compounds with good yields allows for an efficient scale‐up. All synthesized compounds were characterized...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2021-02, Vol.10 (2), p.421-427
Main Authors: Mathpati, Ramling S., Ghule, Vikas D., Dharavath, Srinivas
Format: Article
Language:English
Subjects:
Cations
Derivatives
Energetic cationic component
Energetic materials
Enthalpy
Enthalpy enhancer
Gas generators
Nitrogen
NMR
Nuclear magnetic resonance
Organic chemistry
Synthesis
Tetrazoles
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Summary:Nitrogen‐rich polyazole derivatives were designed and synthesized from the commercially available 4,5‐dicyano‐2‐aminoimidazole. The relatively simple synthesis of multiple azole rings in desired compounds with good yields allows for an efficient scale‐up. All synthesized compounds were characterized by NMR and vibrational spectroscopy, elemental analysis, and DSC studies. The impact and friction sensitivities were measured by the BAM apparatus. The energy content of the target compounds was predicted by using density functional methods. Performing cautious characterization point out that these compounds offer a good combination of high nitrogen‐ and energy‐content with insensitivity towards friction and impact stimuli. These results indicate the superior potential of these nitrogen‐rich polyazole derivatives for enthalpy enhancement, gas generant, and cationic components in energetic salts. Nitrogen‐rich compounds with multiple tetrazoles, oxadiazole, and imidazole rings were synthesized conveniently using the 4,5‐dicyano‐2‐aminoimidazole. All the target compounds possess high nitrogen content (49 to 71%) and have high positive energy content than those of RDX and HMX, owing to the enormous N−N/C−N bonds in the backbone. DSC‐TGA and BAM sensitivity tests indicate that all the compounds are thermally stable and insensitive towards impact and friction. The synthesized nitrogen‐rich compounds are potential candidates for enthalpy enhancement, gas generators, and source of cation moiety in energetic salts.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202000592