Direct fully bio-based polymer synthesis by cellulose modification involving simply mixing cellulose and cinnamaldehyde “cinnamon flavor” in an ionic liquid.
To become independent of petroleum
resources, societies have to
develop methods to synthesize full-biobased polymers from natural
products directly. In this study, full-biobased cellulose esters were
synthesized by the oxidative esterification process between cellulose
and natural α,β-unsaturated aldehydes in an ionic liquid
working as solvent and catalyst. The role of the ionic liquid in this
cellulose-modification system was systematically investigated, and
a newly designed noncarboxylate-type ionic liquid, 1-ethyl-3-methylimidazolium
2-pyridinolate (EmimOPy), was developed to prevent a serious side
reaction in which the carboxylate anion of the carboxylate-type ionic
liquid is introduced into the hydroxyl group of cellulose as an ester
group on the products. Under optimized conditions, this oxidative
esterification-reaction system in EmimOPy afforded fully substituted
cellulose ester (up to the degree of substitution = 3.0). Furthermore,
cellulose reacted with several types of aldehyde substrates, even
biobased low-reactive α- or β-substituted unsaturated
aldehydes (e.g., citral and perillaldehyde). Thus, this synthesis
demonstrates excellent atom economy without using any additional catalysts
or activators under metal-free conditions.
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