Selective aminolysis of mixed esters of cellulose

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Abstract
Aminolysis of cellulose esters was investigated. Of the amines tested (pyrrolidine, n‐butylamine, sec‐butylamine, 2,2‐dimethylpropylamine, piperidine, cyclohexylamine, morpholine), pyrrolidine was the most reactive. The rate of aminolysis by pyrrolidine was approximately the same in dioxane as in dimethyl sulfoxide (DMSO). Using pyrrolidine in DMSO, the relative order of reactivity of the cellulose esters studied was acetate > butyrate ≫ phenylpropionate. With two mixed esters, cellulose acetate 2‐phenylpropionate and cellulose acetate polystyrene carboxylate, deacetylation could be achieved with high specificity. Pyrrolidine in DMSO may also be used to perform a controlled deacetylation of cellulose triacetate in a homogeneous solution down to a degree of substitution of about 0.05. The aminolysis conditions did not cause any degradation of the cellulose chains.