Optimizing extractants selection for efficient separation of phenols and nitrogen-containing heteroaromatics using hydrogen bond interaction strategies

doi:10.1016/j.cjche.2023.12.011

Abstract

Abstract: Focusing on the use of imidazolium ionic liquids and quaternary ammonium salts-based deep eutectic solvents for the separation of phenols and nitrogen-containing heteroaromatics, the role of heteroaromatics as specific sites for hydrogen bond-based separation has been investigated. These environmentally friendly solvents are known for their ability to form hydrogen bonds with heteroatoms, a key aspect in separation processes. We quantified the hydrogen bond interaction energy to reach the threshold energy for efficient O- and N-heteroaromatics separation. This article provides an in-depth study of the structural nuances of different hydrogen bonding sites and their affinity properties while conducting a comparative evaluation of the separation efficiency of ionic liquids and deep eutectic solvents from a thermodynamic perspective. Results showed that phenols with dual hydrogen bonding recognition sites were easier to separate than nitrogen-containing heteroaromatics. Imidazolium ionic liquids were more suitable for the extraction of nonbasic nitrogen-containing heteroaromatics, and quaternary ammonium salts-based deep eutectic solvents are more effective for phenols and basic nitrogen-containing heteroaromatics, which was confirmed by Fourier transform infrared spectroscopy and empirical tests. Therefore, this study provides a theoretical basis for the strategy design and selection of extractants for the efficient separation of O- and N-containing aromatic compounds.

Key words: Deep eutectic solvents, Hydrogen bond, Ionic liquids, Separation, Solvents, Structural characteristics

摘要： Focusing on the use of imidazolium ionic liquids and quaternary ammonium salts-based deep eutectic solvents for the separation of phenols and nitrogen-containing heteroaromatics, the role of heteroaromatics as specific sites for hydrogen bond-based separation has been investigated. These environmentally friendly solvents are known for their ability to form hydrogen bonds with heteroatoms, a key aspect in separation processes. We quantified the hydrogen bond interaction energy to reach the threshold energy for efficient O- and N-heteroaromatics separation. This article provides an in-depth study of the structural nuances of different hydrogen bonding sites and their affinity properties while conducting a comparative evaluation of the separation efficiency of ionic liquids and deep eutectic solvents from a thermodynamic perspective. Results showed that phenols with dual hydrogen bonding recognition sites were easier to separate than nitrogen-containing heteroaromatics. Imidazolium ionic liquids were more suitable for the extraction of nonbasic nitrogen-containing heteroaromatics, and quaternary ammonium salts-based deep eutectic solvents are more effective for phenols and basic nitrogen-containing heteroaromatics, which was confirmed by Fourier transform infrared spectroscopy and empirical tests. Therefore, this study provides a theoretical basis for the strategy design and selection of extractants for the efficient separation of O- and N-containing aromatic compounds.

关键词: Deep eutectic solvents, Hydrogen bond, Ionic liquids, Separation, Solvents, Structural characteristics

Pengzhi Bei, Rui Zhang, Jie Feng, Antony Rajendran, Wenying Li. Optimizing extractants selection for efficient separation of phenols and nitrogen-containing heteroaromatics using hydrogen bond interaction strategies[J]. Chinese Journal of Chemical Engineering, 2024, 68(4): 43-52.

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