Separation of m-cresol from aromatic hydrocarbon and alkane using ionic liquids via hydrogen bond interaction

doi:10.1016/j.cjche.2018.11.009

Abstract

Abstract: Low temperature coal tar contained a large amount of phenols, aromatic hydrocarbons and alkanes; the separation of phenols from coal tar has a great significance to the deep processing of coal tar. In this work, the separation of m-cresol from cumene and n-heptane by liquid-liquid extraction using ionic liquids (ILs) as extractants was studied. The suitable ILs were screened by conductor-like screening model for real solvents (COSMO-RS) model and the liquid-liquid phase equilibrium (LLE) experiments were to verify the accuracy of the screening results. The extraction conditions such as extraction time, extraction temperature and mass ratio of ILs to model oils were evaluated. An internal mechanism of the m-cresol extract by ILs was revealed by COSMO-RS calculation and FT-IR. The results showed that the selected ILs can extract m-cresol effectively from cumene and n-heptane, 1-ethyl-3-methylimidazolium acetate (emimCH₃COO) was the best extraction solvent. A hydrogen bond between anion of ILs and phenolic hydroxyl groups was observed. M-cresol in model oils could be extracted with extraction efficiencies up to 98.85% at an emimCH₃COO:model oils mass ratio of 0.5 and 298.15 K, emimCH₃COO could be regenerated and reused for 4 cycles without obvious decreases in extraction efficiency and extractant mass.

Key words: Extraction, M-cresol, Ionic liquids, Separation, COSMO-RS, Hydrogen bond

摘要： Low temperature coal tar contained a large amount of phenols, aromatic hydrocarbons and alkanes; the separation of phenols from coal tar has a great significance to the deep processing of coal tar. In this work, the separation of m-cresol from cumene and n-heptane by liquid-liquid extraction using ionic liquids (ILs) as extractants was studied. The suitable ILs were screened by conductor-like screening model for real solvents (COSMO-RS) model and the liquid-liquid phase equilibrium (LLE) experiments were to verify the accuracy of the screening results. The extraction conditions such as extraction time, extraction temperature and mass ratio of ILs to model oils were evaluated. An internal mechanism of the m-cresol extract by ILs was revealed by COSMO-RS calculation and FT-IR. The results showed that the selected ILs can extract m-cresol effectively from cumene and n-heptane, 1-ethyl-3-methylimidazolium acetate (emimCH₃COO) was the best extraction solvent. A hydrogen bond between anion of ILs and phenolic hydroxyl groups was observed. M-cresol in model oils could be extracted with extraction efficiencies up to 98.85% at an emimCH₃COO:model oils mass ratio of 0.5 and 298.15 K, emimCH₃COO could be regenerated and reused for 4 cycles without obvious decreases in extraction efficiency and extractant mass.

关键词: Extraction, M-cresol, Ionic liquids, Separation, COSMO-RS, Hydrogen bond

Qian Liu, Xianglan Zhang, Wei Li. Separation of m-cresol from aromatic hydrocarbon and alkane using ionic liquids via hydrogen bond interaction[J]. Chinese Journal of Chemical Engineering, 2019, 27(11): 2675-2686.

Qian Liu, Xianglan Zhang, Wei Li. Separation of m-cresol from aromatic hydrocarbon and alkane using ionic liquids via hydrogen bond interaction[J]. 中国化学工程学报, 2019, 27(11): 2675-2686.

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