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UBC Theses and Dissertations

The photochemical decomposition of polynitrates Kitchen, Richard Allen


The photolysis of nitrate esters in solution or in thin solid films occurred readily in the 2650 to 3340 A spectral region. In the presence of diphenylamine, phloroglucinol or hydroquinone, the photoreaction yielded colored products that gave a measure of the extent of the reaction. The most effective wavelength for formation of yellow products from diphenylamine was at 2890 A. Irradiation of ethanol or benzene solutions 0.02 M in diphenylamine and l,4;3,6-dianhydro-D-glucitol-2,5-dinitrate (isosorbide dinitrate), followed by chromatographic separation, gave six organic compounds, two of which were isolated in pure form by adsorption chromatography and identified as 2- and 4-nitrodiphenylamine. Two other colored products were tentatively identified as N-nitroso- and p-nitrosodiphenyl-amine; no trace of the unreacted nitrate ester could be detected. Photolysis of isosorbide dinitrate alone in ethanol solution caused a weight loss of 17.7% in 21 hours and the formation of an unidentified hydrophilic, colorless sirup. A similar product was obtained on irradiation of an anhydrous benzene solution of the dinitrate. Possible mechanisms of the photolysis are discussed.

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