Synthesis of Mixed Chitin Esters via Acylation of Chitin in Deep Eutectic Solvents

Abstract

The development of efficient derivatization methods of chitin, such as acylation, has been identified to confer new properties and functions to chitin. In this study, we investigate the synthesis of mixed chitin esters via the acylation of chitin in deep eutectic solvents (DESs) comprising 1-allyl-3-methylimidazolum chloride and 1,1,3,3-tetramethylguanidine based on a previous study that reported the development of efficient acylation of chitin in the DES to obtain single chitin esters. A stearoyl group was selected as the first substituent, which was combined with several bulky acyl and long oleoyl groups as the second substituents. After dissolution of chitin in the DES (2 wt%), the acylation reactions were conducted using stearoyl and the desired acyl chlorides for 1 h + 24 h at 100 °C in the resulting solutions. The IR and 1H NMR spectra of the isolated products confirmed the structures of mixed chitin esters with two different substituents. The substituent ratios in the derivatives, which were estimated via the 1H NMR analysis, were changed according to the feed ratios of two acyl chlorides.