The photochemical decomposition of polynitrates
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 effecti...
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ndltd-UBC-oai-circle.library.ubc.ca-2429-399962018-01-05T17:49:52Z The photochemical decomposition of polynitrates Kitchen, Richard Allen Polynitrates Photochemistry 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 2012-01-10T23:14:07Z 2012-01-10T23:14:07Z 1960 Text Thesis/Dissertation http://hdl.handle.net/2429/39996 eng 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. University of British Columbia |
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English |
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Polynitrates Photochemistry |
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Polynitrates Photochemistry Kitchen, Richard Allen The photochemical decomposition of polynitrates |
description |
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 |
author |
Kitchen, Richard Allen |
author_facet |
Kitchen, Richard Allen |
author_sort |
Kitchen, Richard Allen |
title |
The photochemical decomposition of polynitrates |
title_short |
The photochemical decomposition of polynitrates |
title_full |
The photochemical decomposition of polynitrates |
title_fullStr |
The photochemical decomposition of polynitrates |
title_full_unstemmed |
The photochemical decomposition of polynitrates |
title_sort |
photochemical decomposition of polynitrates |
publisher |
University of British Columbia |
publishDate |
2012 |
url |
http://hdl.handle.net/2429/39996 |
work_keys_str_mv |
AT kitchenrichardallen thephotochemicaldecompositionofpolynitrates AT kitchenrichardallen photochemicaldecompositionofpolynitrates |
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1718596530099716096 |