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

Glucosamine-based ionic liquids, potentially green alternatives to common imidazolium based ionic liquids, previously faced limitations in their synthesis due to strong sterical effects resulting from the quarternized ammonium function. In this work we explore several strategies to overcome these limitations, leading to new glycosidic variations and differently substituted ammonium groups.

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.

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