Efficient Liquid–Liquid Extraction of Benzene from Its Mixture with

Jul 23, 2019 - Because the boiling point of benzene (80.1 °C) and cyclohexane (80.7 °C) is much lower than that of DMSO (189 °C) at atmospheric pressu...
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Article Cite This: Ind. Eng. Chem. Res. XXXX, XXX, XXX−XXX

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Efficient Liquid−Liquid Extraction of Benzene from Its Mixture with Cyclohexane by Utilizing Hyperbranched Polymeric Ammoniums Salts Zhiwei Wang,†,∥ Xuan Yuan,†,∥ Guoxing Yang,‡,§ Weidong Zhang,† Lijia Liu,*,† Hongxing Dong,*,† Chunhong Zhang,† Jianwei Bai,† and Linghui Meng§

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Key Laboratory of Superlight Materials & Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China ‡ School of Chemical and Chemical Engineering, Harbin Institute of Technology, Harbin 150001, China § Daqing Petrochemical Research Center, Petrochemical Research Institute, China National Petroleum Corporation, Daqing 163714, China ABSTRACT: A novel hyperbranched polymeric quaternary ammonium salt (HPQAS) with benzene rings in the structure (PVBC-TMA) was synthesized by self-condensing vinyl polymerization followed with quaternary amination reaction. Meanwhile, a hyperbranched polyamidoamine (PAMAM) was separately neutralized with different acids to produce the HPQASs without benzene rings. These HPQASs were dissolved in DMSO and used to extract benzene from its mixture with cyclohexane. The liquid−liquid equilibrium (LLE) data indicate that the HPQAS/DMSO mixture showed a higher selectivity coefficient (19.92) than DMSO ( CH3NH3+/C6H6 (18.8 kcal·mol−1) > (CH3)3NH+/C6H6 (15.9 kcal·mol−1)21), PVBC-TMA having quaternary ammonium groups showed superior extraction performance compared to the PAMAM salts having −CH2NH3+ groups. Especially when the contents of benzene in the raffinate phase was high and close to the azeotropic composition, PVBC-TMA still showed considerable extraction performance, which was obviously higher than the PAMAM salts (Figure 8). In addition to the difference in the ammonium structure, the main difference in the chemical structure between the PAMAM salts and PVBC-TMA is that PVBC-TMA contains a large amount of benzene rings while PAMAM does not. π−π interaction between aromatic rings also is a widely existing nonbonding weak interaction.24,25 Here, the cavity structure containing benzene rings of the hyperbranched PVBC-TMA was thought to be able to easily interact with the benzene due to the π−π interaction formed between the benzene ring in PVBC-TMA with the benzene in the solution. Hence, this afforded PVBC-TMA the higher extraction performance than the PAMAM salts having no benzene rings, although the binding of benzene with the quaternary ammonium in PVBCTMA is weaker than with −CH2NH3+ in PAMAM salts. When the benzene concentration in the system was low, the

Figure 9. Selectivity coefficient of the DMSO + HPQAS system and the reported systems for extracting benzene from its mixture of cyclohexane.

HPQAS system for benzene is at a relative high level, compared to the reported data. Since the solvent used in this paper is mainly DMSO, which has been commercialized on a large scale, considering the relatively large annual production volume of petrochemical industry, it is more economically suitable for industrialization than ionic liquid. Meanwhile, since the highest selectivity coefficient reached 19.92, the DMSO + HPQAS system can compete with some ionic liquids such as [EMim][ESO4],28 and the selectivity of the DMSO + HPQAS system is higher than some ionic liquids I

DOI: 10.1021/acs.iecr.9b01667 Ind. Eng. Chem. Res. XXXX, XXX, XXX−XXX

Article

Industrial & Engineering Chemistry Research including [mim][ClO4]+[C1mim][DMP].10 Therefore, the DMSO + HPQAS system can replace some ionic liquids as a good separation agent to extract benzene from cyclohexane. And for the separation of benzene from cyclohexane by salt extraction, the DMSO + HPQAS system shows a higher selectivity than other reported systems. The selectivity is very close to the KSCN + DMSO system in our previous study.32 However, KSCN is prone to corrosion and blockage of pipes and is unstable under sunlight, while HPQAS has better stability and weak corrosivity. In addition, the distribution ratio of DMSO + HPQAS as the extractant for separating benzene from the cyclohexane mixture is also measured and compared with the reported systems (Figure 10). The distribution ratio of the DMSO +

benzene/cyclohexane mixture were thought to contribute to the extraction process. This was the first example of applying the hyperbranched polymeric ammonium in the separation of benzene/cyclohexane. The HPQAS is expected to be widely applied in industry and expand the field of salt extraction.

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AUTHOR INFORMATION

Corresponding Authors

*[email protected] (L-J. Liu). *[email protected] (H-X. Dong). ORCID

Lijia Liu: 0000-0002-2181-747X Chunhong Zhang: 0000-0001-6068-8140 Author Contributions ∥

These authors contributed equally: Zhiwei Wang and Xuan Yuan.

Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS This work is supported by the National Natural Science Foundations of China (21576060, 51373044, 21574033) and Heilongjiang Province (E2016019) and the Fundamental Research Funds for the Central Universities (3072019CF1011 and HEUCFQ1417). Sincerely thanks for help from Mr. Y. Yusof.

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Figure 10. Distribution ratio of the DMSO + HPQAS system and the reported systems for extracting benzene from its mixture of cyclohexane.

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HPQAS system is slightly lower than that for pure DMSO, but it is still at the medium level in the reported data (Figure 10). This means that the DMSO + HPQAS system is more suitable for separating small amounts of benzene from large amounts of cyclohexane to obtain high purity cyclohexane.

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CONCLUSIONS In this work, two types of HPQASs, PVBC-TMA with benzene rings and PAMAM salts without benzene rings, were successfully synthesized. All the HPQASs showed good thermal stability. DMSO + HPQAS solutions were utilized in the extracted benzene from its mixture with cyclohexane. LLE data of the benzene + cyclohexane + DMSO + HPQAS system were obtained at T = 298.15 K under atmospheric pressure and the selectivity coefficients were calculated. Adding HPQAS in DMSO clearly improved the extraction performance (extraction selectivity of the DMSO + HPQAS system reached 19.92, while for pure DMSO < 15); the extraction selectivity of the DMSO + HPQAS system is close to or higher than extraction selectivities of some ionic liquids. PVBC-TMA having benzene rings showed a higher extraction performance than the PAMAM salts without benzene rings, especially when the benzene concentration is high. Even when the composition of benzene/cyclohexane is close to that of the azeotropioc state, PVBC-TMA still showed a considerable extraction selectivity. The type of counteranions of the HPQASs had an insignificant effect on the extraction selectivity. The cation−π and π−π interactions between the ammonium ion and the benzene ring in the HPQAS with benzene in the J

DOI: 10.1021/acs.iecr.9b01667 Ind. Eng. Chem. Res. XXXX, XXX, XXX−XXX

Article

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DOI: 10.1021/acs.iecr.9b01667 Ind. Eng. Chem. Res. XXXX, XXX, XXX−XXX