Comprehensive evaluation of the role of phenolate based ionic liquid on extracting pyrrole from diverse sources: A combined molecular dynamics simulation study and experiment validation

Overview: Effective Separation of Oxygen-, Nitrogen-, and Sulfur-Containing Aromatics in High-Temperature Coal Tar by Ionic Liquids and Deep Eutectic Solvents: Experimental and Computational

“…Although hydrogen bonds dominate DESs to selectively extract NCAs, − the acidic DESs used will inevitably produce acid–base interaction with pyridine, which can effectively facilitate the separation of BNCAs from HTCT. Interestingly, pyrrole can also be isolated from toluene through 1-ethyl-3-methylimidazolium phenolate by hydrogen bond between a H atom in pyrrole and an O atom in phenolate anion …”

“…As demonstrated in Figure , the hydrogen bond, acid–base interaction, and/or VDWFs can be introduced by −COOH in CC/malonic acid (MA) and nitrogen atom in quinoline, which is stronger than the interaction between CC/MA and carbazole by reduced density gradient (RDG) analysis . The hydrogen bond (N–H···O) and π···π interaction between pyrrole and phenolate anion are much stronger than C–H···π interaction between 1-ethyl-3-methylimidazolium cation and pyrrole as well as the interaction between toluene and pyrrole . Therefore, the hydrogen bond, cation/anion···π, π···π, VDWF, and/or acid–base interaction are widely distributed in ILs/DESs and NCAs, especially the strength of the hydrogen bond between ILs/DESs and BNCAs/NNCAs can sensitively change with the HBA/HBD, which is an irreplaceable factor for ILs/DESs to be used for extracting value-added NCAs from HTCT.…”

“…Interestingly, pyrrole can also be isolated from toluene through 1-ethyl-3-methylimidazolium phenolate by hydrogen bond between a H atom in pyrrole and an O atom in phenolate anion. 71 A new kind of basic DESs composed of crown ether (CE), metal hydroxide, and polyethylene glycol (PEG) was synthesized based on the electrostatic interaction between alkali metal ions (Na + or K + ) and CE as well as hydrogen bonds. The CE-based DESs containing PEG-400 can more superiorly extract carbazole than indole and pyrrole, suggesting that PEG with the medium chain length and suitable viscosity plays a significant role.…”

“…80 The hydrogen bond (N−H•••O) and π•••π interaction between pyrrole and phenolate anion are much stronger than C−H•••π interaction between 1-ethyl-3-methylimidazolium cation and pyrrole as well as the interaction between toluene and pyrrole. 71 Therefore, the hydrogen bond, cation/anion•••π, π•••π, VDWF, and/or acid−base interaction are widely distributed in ILs/DESs and NCAs, especially the strength of the hydrogen bond between ILs/DESs and BNCAs/NNCAs can sensitively change with the HBA/HBD, which is an irreplaceable factor for ILs/DESs to be used for extracting value-added NCAs from HTCT.…”