Revisiting the Synthesis of Cellulose Acrylate and Its Modification via Michael Addition Reactions

The synthesis of cellulose acrylate from cellulose withacryloylchloride has been problematic due to unexpected gelation of the reactionmixture, but we discovered that the use of bulky amines was crucialfor the reproducibility of the synthesis of cellulose acrylate. Thesolubility of the obtained cellulose acrylate depended on the reactionconditions due to the possible cross-linking oxa-Michael reactionbetween a remaining hydroxy group and the introduced acrylate group.The synthesized cellulose acrylate worked as a useful precursor ofchemically modified cellulose materials because it reacted with variousfunctionalized nucleophiles such as secondary amines and thiols asa Michael donor. This method was applied to the synthesis of N-methyl-d-glucamine-modified cellulose that worksas an adsorbent for the removal of B(OH)(3) in water.