Scope and Limitations in the Synthesis of Glucosamine‐based Ionic Liquids

Abstract

This research article focuses on the synthesis of ionic liquids from glucosamine, a renewable material obtained from chitin. Our group previously experienced some obstacles in the synthesis of these glucosamine‐based ionic liquids, often due to the sterical hindrance induced by the dimethylated amino‐group. In this work we present a method using Borch reductive amination to overcome these limitations to achieve a dimethylethylamino‐group. We furthermore expanded upon the library of glucosamine‐based ionic liquids with new glycosidic groups, discovered a new shortened reaction procedure by skipping a deprotection step and finally compared the thermal properties of the ionic products to get an insight into structure‐property relationships.

Synthesis, biocompatibility, and antimicrobial properties of glucose-based ionic liquids

“…In recent years, these carbohydrate-based ionic liquids (CHILs) [13][14][15] have found several potential applications, like a positive inuence on the rate and selectivity of Diels-Alder cycloadditions, 16 the possibility to adsorb metal cations like Pb 2+ and Cd 2+ from an aqueous solution, 17,18 as precursors for N-doped carbon materials 19 or as supported ionic liquid phase for the immobilized Candida antarctica lipase B biocatalyst (Novozym 435). 20 Jopp et al recently developed several synthetic processes to produce ILs based on carbohydrates such as riboses, 21 glucosamine, 22 and glucose, 20 and has furthermore proven remarkable biocompatibility of glucose and pentose-based pyridinium ILs. 23 However, many syntheses towards these CHILs include several reaction steps, including insertion and removal of protecting groups and inserting a leaving group to enable following quaternization with N-heterocycles or amines.…”

“…Jopp et al recently developed several synthetic processes to produce ILs based on carbohydrates such as riboses, 21 glucosamine, 22 and glucose, 20 and has furthermore proven remarkable biocompatibility of glucose and pentose-based pyridinium ILs. 23 However, many syntheses towards these CHILs include several reaction steps, including insertion and removal of protecting groups and inserting a leaving group to enable following quaternization with N-heterocycles or amines.…”