(580a) Bio-Based Amphiphile Preparation through Aldehyde Assisted Lignocellulosic Biomass Fractionation

The environmental concerns over fossil-derived surfactants, a ubiquitous consumer chemical, necessitates the search for sustainable bio-based alternatives. Lignocellulosic biomass contains abundant polar functional groups (in particular hydroxyl groups), which can be extracted and used directly as natural hydrophiles. However, these reactive and vulnerable groups are prone to degradation during fractionation processes. Here, we prepared bio-based amphiphiles using native hydrophilic molecules from biomass in a facile two-step “protection-deprotection” reaction. First, the diol structure of xylan and lignin were actively protected from degradation by forming cyclic acetals with fatty aldehyde during fractionation. The long alkyl chain in aldehyde simultaneously introduces hydrophobic counterparts. Second, blocked hydrophiles were partially released through deprotection. A series of amphiphilic xylose acetals and ethers has been obtained by the hydrogenolysis of xylose diacetal catalysed by Pd/C. Meanwhile, lignin-based amphiphilic polymers were prepared through acidic hydrolysis in a biphasic reaction. The amphiphilic properties of both families were utilized in emulsion stabilization, exhibiting promising surfactant properties.