Renewable imidazolium zwitterions as platform molecules for the synthesis of ionic liquids and materials

Following the principles of green chemistry, a simple and efficient synthesis of functionalised imidazolium zwitterionic compounds from renewable resources was developed based on a modified one-pot Debus-Radziszewski reaction. The combination of different carbohydrate-derived 1,2-dicarbonyl compounds and amino acids is a simple way to modulate the properties and introduce different functionalities. A representative compound was assessed as an acid catalyst, and converted into acidic ionic liquids by reaction with several strong acids. The reactivity of the double carboxylic functionality was explored by esterification with long and short chain alcohols, as well as functionalised amines, which led to the straightforward formation of surfactant-like molecules or bifunctional esters and amides. One of these di-esters is currently being investigated for the synthesis of poly(ionic liquids). The functionalisation of cellulose with one of the bifunctional esters was investigated and preliminary tests employing it for the functionalisation of filter papers were carried out successfully. The imidazolium zwitterions were converted into ionic liquids via hydrothermal decarboxylation in flow, a benign and scalable technique. This method provides access to imidazolium ionic liquids via a simple and sustainable methodology, whilst completely avoiding contamination with halide salts. Different ionic liquids can be generated depending on the functionality contained in the ImZw precursor. Two alanine-derived ionic liquids were assessed for their physicochemical properties and applications as solvents for the dissolution of cellulose and the Heck coupling.

Level thesis:degree_level

thesis.doctoral

Grantor dc:publisher

Universität Potsdam

Year

2015

Author dc:creator

• Kirchhecker, Sarah

Contributors dc:contributor

• Antonietti, Markus

• ionic liquids
• platform chemicals
• renewables
• imidazolium
• green chemistry
• hydrothermal
• ionische Flüssigkeiten
• nachhaltige Chemie
• Zwitterionen
• nachwachsende Rohstoffe

Statement dc:rights

• CC-BY-NC-ND - Namensnennung, nicht kommerziell, keine Bearbeitungen 4.0 International

Repository record source_url

https://publishup.uni-potsdam.de/frontdoor/index/index/docId/7741

OAI identifier oai:identifier

oai:kobv.de-opus4-uni-potsdam:7741