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

[Display omitted] •xylan aryl carbonates are versatile building blocks for modular synthesis approaches.•activated phenyl carbonates can be converted into functional xylan carbamates.•primary and secondary amines can be employed for quantitative conversion.•final properties are defined by the molecular structure of the activated intermediate.•an- and cationic xylan derivatives are both accessible from the same intermediate. 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.