Modular synthesis of non-charged and ionic xylan carbamate derivatives from xylan carbonates

Lars Gabriel; Martin Gericke; Thomas Heinze

doi:10.1016/j.carbpol.2018.12.012

Modular synthesis of non-charged and ionic xylan carbamate derivatives from xylan carbonates

Carbohydr Polym. 2019 Mar 1:207:782-790. doi: 10.1016/j.carbpol.2018.12.012. Epub 2018 Dec 7.

Authors

Lars Gabriel¹, Martin Gericke², Thomas Heinze³

Affiliations

¹ Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University of Jena, Centre of Excellence for Polysaccharide Research, Humboldtstraße 10, D-07743 Jena, Germany.
² Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University of Jena, Centre of Excellence for Polysaccharide Research, Humboldtstraße 10, D-07743 Jena, Germany. Electronic address: martin.gericke@uni-jena.de.
³ Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University of Jena, Centre of Excellence for Polysaccharide Research, Humboldtstraße 10, D-07743 Jena, Germany. Electronic address: thomas.heinze@uni-jena.de.

PMID: 30600065
DOI: 10.1016/j.carbpol.2018.12.012

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.

Keywords: Chemical modification; Polyelectrolytes; Polysaccharides; Xlyan derivatives; Xylan carbamates; Xylan phenyl carbonates.