Thermally insensitive explosives synthesis

ANTA (114) readily forms a stable anion on reaction with bases like sodium ethoxide and this anion has been used as a nucleophile for the synthesis of many ANTA derivatives. Laval and co-workers synthesizedDANTNP (116) (calculated VOD 8120 m/s, = 1.84 g/cm, m.p. > 330 °C) from the reaction of 4,6-dichloro-5-nitropyrimidine (115) with two equivalents of ANTA (114) in the presence of sodium ethoxide. Agrawal and co-workers studied the thermal and explosive properties of both ANTA and DANTNP and suggested their use for applications in propellant/explosive formulations where insensitivity coupled with thermal stability is of prime importance. The activation energies of ANTA and DANTNP indicate that DANTNP is more thermally stable than ANTA. 

Amino-1,2,4-triazole is a useful starting material for the synthesis of many 1,2,4-triazole-based explosives. Jackson and Coburn synthesized a number of picryl- and picrylamino-substituted 1,2,4-triazoles. PATO (99) is synthesized from the reaction of 3-amino-1,2,4-triazole (98) with picryl chloride (67). ° PATO has also been synthesized from the reaction of 3-amino-l,2,4-triazole with A,2,4,6-tetranitromethylaniline (tetryl). PATO has a low sensitivity to impact and is thermally stable up to 310 °C. PATO (VOD 7469 m/s) exhibits lower performance to TATB (VOD 8000 m/s) which is the common benchmark standard for thermal stability and insensitivity in explosives. 

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