A method of increasing the yield of methanol lignin was devised in collaboration with Mr. J. Swartz. Some of the methoxyl groups of completely methylated methanol lignin were shown to be probably anolic in nature. Catalytic reduction of this material, using two of the more recently developed catalysts, Was attempted, the results obtained being entirely negative. The optimum conditions for complete demethylation of the methylated lignin with hydriodic acid were determined, and the rate of the reaction investigated. The alkoxyl group in the initial material was shown to be exclusively methoxyl. The major solid product of the demethylation was investigated; as obtained it contained iodine, and a method for the removal of the latter was devised. Examination of this material showed that dehydroxylation had occurred to a large extent, and that the residual hydroxyl groups wer e largely (90%) phenolic in nature. A theory as to the mechanism of this dehydroxylation has been advanced, together with supporting evidence. A comparison of two methods of synthesis of benzo-2,3- (dioxin-l,4-dihydride-5,6) has been made.

Hibbert, H. (Supervisor)