Highly-efficient separation of pyromellitic acid and trimellitic acid mixtures via forming deep eutectic solvents: Experiment and calculation

doi:10.1016/j.cjche.2024.09.012

中国化学工程学报 ›› 2024, Vol. 76 ›› Issue (12): 42-48.DOI: 10.1016/j.cjche.2024.09.012

Highly-efficient separation of pyromellitic acid and trimellitic acid mixtures via forming deep eutectic solvents: Experiment and calculation

Wanxiang Zhang¹, Lixia Ji¹, Yucui Hou², Shuhang Ren¹, Weize Wu¹

1. State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical Technology, Beijing 100029, China;
2. Department of Chemistry and Materials, Taiyuan Normal University, Shanxi 030619, China

收稿日期:2024-06-10 修回日期:2024-09-19 接受日期:2024-09-23 出版日期:2024-12-28 发布日期:2024-10-16
通讯作者: Shuhang Ren,E-mail:rensh@mail.buct.edu.cn;Weize Wu,E-mail:wzwu@mail.buct.edu.cn
基金资助:
The authors thank Prof. Zhenyu Liu and Qingya Liu for their helpful discussion and suggestions and the long-term subsidy mechanism from the Ministry of Finance and the Ministry of Education of PRC (BUCT). The project is financially supported by the National Natural Science Foundation of China (21676019 and 21776199).

Highly-efficient separation of pyromellitic acid and trimellitic acid mixtures via forming deep eutectic solvents: Experiment and calculation

Wanxiang Zhang¹, Lixia Ji¹, Yucui Hou², Shuhang Ren¹, Weize Wu¹

1. State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical Technology, Beijing 100029, China;
2. Department of Chemistry and Materials, Taiyuan Normal University, Shanxi 030619, China

Received:2024-06-10 Revised:2024-09-19 Accepted:2024-09-23 Online:2024-12-28 Published:2024-10-16
Contact: Shuhang Ren,E-mail:rensh@mail.buct.edu.cn;Weize Wu,E-mail:wzwu@mail.buct.edu.cn
Supported by:
The authors thank Prof. Zhenyu Liu and Qingya Liu for their helpful discussion and suggestions and the long-term subsidy mechanism from the Ministry of Finance and the Ministry of Education of PRC (BUCT). The project is financially supported by the National Natural Science Foundation of China (21676019 and 21776199).

摘要/Abstract

摘要： Pyromellitic acid (PMA) and trimellitic acid (TMA) are significant chemical raw materials and intermediates. They simultaneously exist in the industry processes of synthesis and are difficult to be separated. In this work, several kinds of biodegradable compounds were chosen as hydrogen bond acceptors (HBAs) to separate PMA and TMA mixtures from acetone solutions via forming deep eutectic solvent (DES). It has been found that all these compounds can separate PMA and TMA mixtures to obtain pure PMA or TMA. However, the interaction between HBAs and PMA or TMA is quite different. Choline chloride cannot extract TMA but can form a DES with PMA in acetone. Hexamethylenetetramine (HA) and L-carnitine (L-car) can form DESs with both PMA and TMA in acetone solution. But when L-car or HA is added, the extraction rate of PMA is larger than that of TMA until the extraction rate of PMA reach 100%, and pure TMA is left in the acetone solution. The selective separation mechanism was explored by infrared spectroscopy combined with quantum chemistry calculation, and the strength and site of the interaction between extractants with PMA and TMA were calculated.

关键词: Separation, Pyromellitic acid, Trimellitic acid, Deep eutectic solvent, Quantum chemistry calculation

Abstract: Pyromellitic acid (PMA) and trimellitic acid (TMA) are significant chemical raw materials and intermediates. They simultaneously exist in the industry processes of synthesis and are difficult to be separated. In this work, several kinds of biodegradable compounds were chosen as hydrogen bond acceptors (HBAs) to separate PMA and TMA mixtures from acetone solutions via forming deep eutectic solvent (DES). It has been found that all these compounds can separate PMA and TMA mixtures to obtain pure PMA or TMA. However, the interaction between HBAs and PMA or TMA is quite different. Choline chloride cannot extract TMA but can form a DES with PMA in acetone. Hexamethylenetetramine (HA) and L-carnitine (L-car) can form DESs with both PMA and TMA in acetone solution. But when L-car or HA is added, the extraction rate of PMA is larger than that of TMA until the extraction rate of PMA reach 100%, and pure TMA is left in the acetone solution. The selective separation mechanism was explored by infrared spectroscopy combined with quantum chemistry calculation, and the strength and site of the interaction between extractants with PMA and TMA were calculated.

Key words: Separation, Pyromellitic acid, Trimellitic acid, Deep eutectic solvent, Quantum chemistry calculation

Wanxiang Zhang, Lixia Ji, Yucui Hou, Shuhang Ren, Weize Wu. Highly-efficient separation of pyromellitic acid and trimellitic acid mixtures via forming deep eutectic solvents: Experiment and calculation[J]. 中国化学工程学报, 2024, 76(12): 42-48.

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Highly-efficient separation of pyromellitic acid and trimellitic acid mixtures via forming deep eutectic solvents: Experiment and calculation

Highly-efficient separation of pyromellitic acid and trimellitic acid mixtures via forming deep eutectic solvents: Experiment and calculation

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