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Published on: August 23, 2018
Modular synthesis of non-charged and ionic xylan carbamate derivatives from xylan carbonates
Lars Gabriel1, Martin Gericke1, Thomas Heinze1
1Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University of Jena, Centre of Excellence for Polysaccharide Research, Humboldtstraße 10, D-07743 Jena, Germany.
Abstract:
Novel non-charged and ionic xylan carbamate (XC) derivatives were synthesized in a modular approach from xylan phenyl carbonates (XPC) as reactive intermediates. XPC with varying degrees of substitution (DS) from 0.5 to 1.9 were converted with different non-ionic primary and secondary amines in different molar ratio to obtain the corresponding XC with high conversion rates of up to 100%. In a similar way, ionic amines were employed for the aminolysis of XPC to obtain charged XC. The XC were characterized by NMR- and infrared spectroscopy. XPC proofed to be highly versatile building blocks for the preparation of ionic xylan derivatives. The type and amount of charged groups could be tuned efficiently. Moreover, high DS values of up to 1.4 for cationic and 1.8 for anionic XC derivatives could be achieved, which is higher than reported previously for comparable ionic xylan derivatives that were prepared by "conventional" esterification and etherification reactions.
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