A pathway to improve detoxification processes by selective extraction of phenols and sugars from aqueous media using sustainable solvents

Highlights

• Carboxylic acid-based hydrophobic eutectic solvents were formed and characterized.

• Extraction efficiency of hydrophobic eutectic solvents and bio-based solvents were obtained by HPLC-DAD/RI.

• Selective extraction of phenols from sugar-rich aqueous streams could enhance fermentation processes.

• Best selectivity and efficiency results were obtained with cyclopentyl methyl ether.

• The experimental results were analyzed by means of COSMO-RS methodology.

Abstract

Integrated biorefineries are the current trend to produce energy, biochemicals and biofuels. A variety of sugar-rich biorefinery streams can be further valorized by fermentation but the presence of inhibitory compounds hinders the fermentation yields. This paper proposes a detoxification method by selective liquid extraction of phenolic compounds using sustainable solvents to improve the fermentation of sugar-rich aqueous streams. Specifically, three hydrophobic eutectic solvents constituted by binary mixtures of octanoic, decanoic or dodecanoic acid (octanoic: decanoic acid 1:1, octanoic: dodecanoic acid 3:1, decanoic: dodecanoic acid 2:1) and three bio-based solvents (2-methyltetrahydrofuran, cyclopentyl methyl ether and limonene) were selected to analyze their capacity to extract representative phenolic compounds (phenol, o-cresol, guaiacol, syringol and vanillin) from aqueous solutions. Extraction efficiencies of individual compounds and mixtures of them were evaluated at different concentrations and temperatures using the proposed solvents. Finally, the liquid extraction of a solution containing 500 mg/L of phenolic compounds and 50 g/L of glucose, as a representative concentration in biorefinery streams, was performed. The distribution of the target compounds in each phase after the extraction process was analyzed by HPLC-DAD in the case of phenolic compounds and HPLC-RI for glucose, and discussed in terms of selectivity. The results obtained are very promising, as the studied solvents can easily extract phenolic compounds but not glucose, which could improve the subsequent sugar fermentation process. In particular, the bio-based solvent cyclopentyl methyl ether provided extraction efficiencies of phenolic compounds above 93%, while that of glucose remained lower than 4%. Finally, all the experimental results were analyzed by means of COSMO-RS methodology, obtaining reliable trends and concluding that the ability of the solvents to form hydrogen bonds with phenolic compounds determines the extraction efficiencies.