Research in Nitromonomers and Their Application to Solid Smokeless Propellants.
Report no. 3, 1 Jan 59-31 Dec 60,
OHIO STATE UNIV RESEARCH FOUNDATION COLUMBUS
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Oxidation of aqueous sodium phenylmethane-nitronate with ammonium persulfate yields d,1-major product and meso-1,2-dinitro-1,2-diphenylethanes along with cis-alpha-nitrostilbene, alpha, beta, gamma-triphenyl-alpha-nitropropene, 3,4,5-triphenylisoxazoline oxide, 3,4,5-triphenylisoxazole, benzaldehyde, and benzoic acid. The complex condensation products are derived by the actions of bases on the 1,2-dinitro-1,2-diphenylethanes or from benzaldehyde and phenylnitromethane. The actions of persulfate on nitronates are greatly accelerated by trace quantities of silver ion. Salts of 1-nitropropane and 2-methyl-1-nitropropane respectively were oxidized with persulfates in the presence or absence of silver ion to give oxidative-dimers. Reaction of potassium 1-nitropentane-1-nitronate with ammonium persulfate yielded valeric acid and valeramide. The sodium salt of phenyldinitromethane is not oxidized by aqueous persulfate. Possible mechanisms for formation of the products of the various oxidation reactions are proposed and discussed. Heterogeneous decompositions of silver salts of primary and secondary nitro compounds give silver, oxidative-dimers and aldehydes or ketones. A study has now been made of homogeneous oxidation of salts of nitro compounds by silver nitrate in acetonitrile-water or dimethyl sulfoxide-water. Oxidations of primary nitronates by silver ion gave poorer yields of oxidative-dimers than did persulfates the reactions are complicated by formation of 1, 1-dinitro compounds, nitro alcohols, nitroolefins and aldehydes. Possible mechanisms for formation of the products obtained from oxidations with silver ion are proposed and discussed. Author
- Organic Chemistry
- Ammunition and Explosives