Bicyclic guanidine superbase carboxylate salts for cellulose dissolution

Bicyclic guanidines are utilized in organic synthesis as base catalysts or reagents. They also offer a platform for coordination chemistry, for example in CO2 activation, and their carboxylate salts offer an efficient media for cellulose dissolution. We have studied a series of bicyclic guanidines with varying ring sizes and with varying methyl substituents with a specific aim to find hydrolytically stable acetate salts for dissolution and processing of cellulose. Different superbase synthesis pathways were tested, followed by hydrolytic stability and cellulose dissolution capacity tests. The synthesis pathways were designed to enable the scale up of the production of the superbases considering the availability of the starting molecules and the feasibility of the synthesis. As a result, we found several hydrolytically stable bicyclic guanidine structures, which can overcome many of the reoccurring problems as carboxylate salts or free bases.