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

中国化学工程学报 ›› 2024, Vol. 68 ›› Issue (4): 43-52.DOI: 10.1016/j.cjche.2023.12.011

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

Pengzhi Bei¹, Rui Zhang¹, Jie Feng¹, Antony Rajendran², Wenying Li¹

1. State Key Laboratory of Clean and Efficient Coal Utilization, Taiyuan University of Technology, Taiyuan 030024, China;
2. Department of Chemistry, Mepco Schlenk Engineering College (Autonomous), Sivakasi 626005, India

收稿日期:2023-06-13 修回日期:2023-12-25 出版日期:2024-04-28 发布日期:2024-06-28
通讯作者: Wenying Li,E-mail address:ying@tyut.edu.cn
基金资助:
The authors are very grateful for the financial support from the National Natural Science Foundation of China (22038008) and the science and technology innovation project of China Shenhua Coal to Liquid and Chemical Company Limited (MZYHG-2021-01).

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

Pengzhi Bei¹, Rui Zhang¹, Jie Feng¹, Antony Rajendran², Wenying Li¹

1. State Key Laboratory of Clean and Efficient Coal Utilization, Taiyuan University of Technology, Taiyuan 030024, China;
2. Department of Chemistry, Mepco Schlenk Engineering College (Autonomous), Sivakasi 626005, India

Received:2023-06-13 Revised:2023-12-25 Online:2024-04-28 Published:2024-06-28
Contact: Wenying Li,E-mail address:ying@tyut.edu.cn
Supported by:
The authors are very grateful for the financial support from the National Natural Science Foundation of China (22038008) and the science and technology innovation project of China Shenhua Coal to Liquid and Chemical Company Limited (MZYHG-2021-01).

摘要/Abstract

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

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

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]. 中国化学工程学报, 2024, 68(4): 43-52.

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

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

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