Isomer distribution of nitro derivatives of diphenylamine in gun propellants: Nitrosamine Chemistry

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Abstract
The derivatisation of diphenylamine (DPA) in single base gun propellants was studied as a function of aging at 80°C. The relative proportions of 2‐nitro DPA and 4‐nitro DPA varied from 32 : 68 to 63 : 37 according to propellant type. Preferences for para substitution were seen in experimental lots “stabilized” with 2‐nitroDPA, 4‐nitroDPA and N‐nitrosoDPA. Increasing water content resulted in higher preferences for ortho substitution. 4‐NitroDPA is a better stabilizer than 2‐nitroDPA. Model studies performed using nitro substituted N‐nitrosamines show that para substitution is preferred in boiling acetic acid. Mechanisms for the conversion of N‐nitrosamines into isomeric nitro derivatives are discussed with relation to the model studies and the behaviour in propellants. Detailed experimental procedures are given for the preparation of N‐nitrosamines.