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

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.

Graphical abstract

Keywords

separation mechanism / dispersion interaction / coal tar / polycyclic aromatic hydrocarbons

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Competing interests

The authors declare that they have no competing interests.

Acknowledgements

The authors gratefully acknowledge financial support provided by the National Natural Science Foundation of China (Grant No. 22038008) and the China Shenhua Coal-to-Liquids Chemical Co., Ltd. Science and Technology Innovation Project (Grant No. MZYHG-2021-01).

Electronic Supplementary Material

Supplementary material is available in the online version of this article at https://doi.org/10.1007/s11705-024-2462-9 and is accessible for authorized users.

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