Periodate oxidation of cellulose to produce dialdehyde cellulose (DAC) received a considerable amount of research interest in sustainable materials development lately. Besides the possibilities offered by DAC itself, the introduced aldehyde functionalities furthermore allow for derivatizations, <i>e.g.,</i> over reductions, oxidations, or reactions with <i>N</i>-nucleophiles. While the literature on these topics is plentiful, it turned out not to be conclusive and, in some parts, even contradictory. In attempts to implement DAC chemistry to add functionality to cellulose fibers, we thus encountered various problems. These can be attributed to the peculiarities of DAC including its tendency towards beta elimination and the formation of highly crosslinked and stable structures. Consequently, efforts were undertaken to better understand and tackle these fundamental issues. By applying state of the art analytical techniques like solution state cellulose NMR spectroscopy and an indirect GPC protocol, new insights into the occurring side reactions could be obtained. The results of critical investigations concerning contaminations with residual oxidizing iodine compounds, reductive aminations of DAC and the depolymerization during periodate oxidation will be presented. We highlight the importance of side reactions in DAC chemistry and present strategies to avoid them, thereby providing a refined toolbox for cellulose derivatization and valorization.

Side reactions in dialdehyde cellulose chemistry critically revisited

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