The synthesis of fructose-based surfactants.

This study describes the synthesis of a new class of surfactants that is based on the bioderived building blocks fructose, fatty acid methyl esters (FAME), and hydroxy propionitrile (cyanoethanol, 3-HP). The synthesis is scalable, is carried out at ambient conditions, and does not require chromatography. The produced surfactants have excellent surfactant properties with critical micelle concentrations and Krafft points comparable to current glucose-based surfactants.

Substituted anilides from chitin-based 3-acetamido-furfural.

The synthesis of aromatic compounds from biomass-derived furans is a key strategy in the pursuit of a sustainable economy. Within this field, a Diels-Alder/aromatization cascade reaction with chitin-based furans is emerging as a powerful tool for the synthesis of nitrogen-containing aromatics. In this study we present the conversion of chitin-based 3-acetamido-furfural (3A5F) into an array of di- and tri-substituted anilides in good to high yields (62-90%) via a hydrazone mediated Diels-Alder/aromatization sequence. The addition of acetic anhydride expands the dienophile scope and improves yields. Moreover, replacing the typically used dimethyl hydrazone with its pyrrolidine analogue, shortens reaction times and further increases yields. The hydrazone auxiliary is readily converted into either an aldehyde or a nitrile group, thereby providing a plethora of functionalized anilides. The developed procedure was also applied to 3-acetamido-5-acetylfuran (3A5AF) to successfully prepare a phthalimide.