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UBC Theses and Dissertations

Polymer-analogous denitration, a study of certain hexitol, disaccharide and cellulose nitrates Swan, Eric Paterson

Abstract

The action of methanolic hydrazine with palladium catalyst, methyl magnesium iodide, and hydrogen with cupric acetate catalyst in pyridine solution, on certain hexitol and disaccharide polynitrates were found to be unsuitable methods for complete denitration of these carbohydrate polynitrates. Lithium aluminium hydride was shown to denitrate successfully D-mannitol hexanitrate. The foregoing methods were found to be unsuitable for complete denitration of polysaccharide polynitrates. Hydrogen with palladium-carbon catalyst was shown to denitrate successfully all the carbohydrate polynitrates studied, with good yields of the parent polyol. The use of hydrogen was extended to denitration of cellulose nitrates. In the presence of Raney nickel catalyst a cellulose nitrate containing 13.4% N was reduced to a cellulose nitrate containing 12.1% N. The reduction with hydrogen and Raney nickel catalyst of a heterogeneous cellulose nitrate, containing approximately equal amounts of a cellulose nitrate containing 4.5% N and one containing 12.6% N, was found to yield a cellulose nitrate containing 2.7% N and one containing 12.5% N.

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