Molecular mechanism and extraction performance evaluation of choline chloride-based deep eutectic solvents for phenol separation from oil: Different glycols as hydrogen bond donors

Highly efficient separation of phenols from coal-to-liquids can enhance the economics of the coal conversion process. The selection of extractants with high extraction efficiency and low neutral oil entrainment is significant for energy development strategy. In this study, four ChCl-based DESs with different glycols as hydrogen bond donors (HBDs) were designed for the separation of phenol/toluene mixtures and the experimental results were analyzed by theoretical calculations. The experimental results showed that ChCl-EG had the highest extraction efficiency (94.02 %) and the least entrainment of toluene (0.449 g). Meanwhile, it could be regenerated and reused four times with no significant change in extraction capacity. The formation of hydrogen bonds between DESs and phenol was elucidated by σ-profile based on COSMO-SAC model. Multi-scale simulations and comparative analyses of the micro-mechanisms of the DESs system were carried out using quantum chemical (QC) and molecular dynamics (MD). It was shown that the attraction of DESs to phenol was mainly due to hydrogen bonds and vdW forces, with hydrogen bond interaction between Cl− in ChCl and H atom in phenol hydroxyl group being dominant. As the chain length of HBDs increased, the interaction of DESs with phenol was enhanced, while the entrainment of toluene also increased. Overall, the effect on the separation of phenol by different chain lengths of glycols as HBDs is elucidated. This study provides a theoretical reference for selecting and designing other DES extractants to separate phenol/toluene systems and similar systems.