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. / Science, Faculty of / Chemistry, Department of / Graduate
| Identifer | oai:union.ndltd.org:UBC/oai:circle.library.ubc.ca:2429/39996 |
| Date | January 1960 |
| Creators | Kitchen, Richard Allen |
| Publisher | University of British Columbia |
| Source Sets | University of British Columbia |
| Language | English |
| Detected Language | English |
| Type | Text, Thesis/Dissertation |
| Rights | For non-commercial purposes only, such as research, private study and education. Additional conditions apply, see Terms of Use https://open.library.ubc.ca/terms_of_use. |
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