Synthetic Routes for Designing Furanic and Non Furanic Biobased Surfactants from 5-Hydroxymethylfurfural

Abstract

5-hydroxymethylfurfural (HMF) is one of the most valuable biomass platform molecules, enabling the construction of a plethora of high value-added furanic compounds. In particular, in the last decade, HMF has been considered as a starting material for designing biobased surfactants, not only because of its renewability and carbon footprint, but also because of its enhanced biodegradability. This Review presents recent examples of the different approaches to link the hydrophilic and lipophilic moieties into the hydrophobic furan (and tetrahydrofuran) ring, giving a variety of biobased surfactants that have been classified here according to the charge of the head polar group. Moreover, strategies for the synthesis of different non-furanic structures surfactant molecules (such as levulinic acid, cyclopentanols, and aromatics) derived from HMF are described. The new HMF-based amphiphilic molecules presented here cover a wide range of hydrophilic-lipophilic balance values and have suitable surfactant properties such as surface tension activity and critical micelle concentration, to be an important alternative for the replacement of non-sustainable surfactants.

Keywords: 3-hydroxycyclopentanol; 5-hydroxymethylfurfural; aromatics; levulinic acid; surfactants.