Deciphering the intermolecular interactions for separating bicyclic and tricyclic aromatics via different naphthalene-based solvents

doi:10.1007/s11705-024-2462-9

2024, Vol. 18

Issue (10) : 111 https://doi.org/10.1007/s11705-024-2462-9

Deciphering the intermolecular interactions for separating bicyclic and tricyclic aromatics via different naphthalene-based solvents

Pengzhi Bei¹, Antony Rajendran², Jie Feng¹, Wen-Ying 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, Sivakasi 626005, India

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Abstract

The traditional separation of bicyclic and tricyclic aromatics from coal tar involves complicated multi-steps and consumes significantly more energy. Previous work accomplished the separation between anthracene-phenanthrene isomers using electrostatic interaction, but for the separation between bicyclic and tricyclic aromatics, electrostatic interactions are difficult to produce a recognizable effect. Naphthalene-based solvents, named as naphthaleneacetamide, naphthaleneethanol, naphthalenemethanol, naphthol, naphthylacetic acid, naphthylacetonitrile, and naphthylamine, respectively, were used for the efficient separation of naphthalene and phenanthrene via dispersion interaction. Results showed that the pre-studied structural parameters are the key factors in selecting an efficient solvent. And the substituents on the intermolecular interactions involved in the separation processes had an important impact, which were evaluated. Naphthalenemethanol exhibited a superior performance with a purity of 96.3 wt % naphthalene products because its electron-donating substituent enables the selective recognition of naphthalene via the dispersion interaction. The used naphthalene-based solvents can be regenerated and recycled via back extraction with a purity of over 90 wt % naphthalene products, suggesting solvent structural stability during the regeneration processes. Notably, the naphthalene-based solvents also demonstrated better separation performance for polycyclic aromatics from coal tar with a purity of over 80 wt % for bicyclic aromatics. This study would enhance the utilization of coal tar as a valuable source of polycyclic aromatics besides broadening the knowledge for applying non-bonded interaction in the separation of polycyclic aromatics technologies.

Keywords separation mechanism dispersion interaction coal tar polycyclic aromatic hydrocarbons

Corresponding Author(s): Wen-Ying Li

Just Accepted Date: 29 April 2024 Issue Date: 17 June 2024

Cite this article:

Pengzhi Bei,Antony Rajendran,Jie Feng, et al. Deciphering the intermolecular interactions for separating bicyclic and tricyclic aromatics via different naphthalene-based solvents[J]. Front. Chem. Sci. Eng., 2024, 18(10): 111.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-024-2462-9
https://academic.hep.com.cn/fcse/EN/Y2024/V18/I10/111

Fig.2 Separation effect of different naphthalene-based solvents. K: partition coefficient.

Tab.1 Separation performances of synthesized solvent

Fig.3 The dispersion interaction energy between naphthalenemethanol and naphthalene/phenanthrene.

Fig.4 GC × GC-MS analysis results. (a) Coal tar, (b) bicyclic aromatic hydrocarbons, and (c) tricyclic aromatic hydrocarbons.

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Zihan Xu, Huajie Xu, Lu Liu, Rongpei Jiang, Haisheng Ren, Xiangyuan Li. High-precision standard enthalpy of formation for polycyclic aromatic hydrocarbons predicting from general connectivity based hierarchy with discrete correction of atomization energy[J]. Front. Chem. Sci. Eng., 2022, 16(12): 1743-1750.

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