Research advances of extraction separation of phenolic compounds by ionic liquids

doi:10.16085/j.issn.1000-6613.2023-1588

Abstract

Abstract:

Ionic liquids contain imidazolium-based, choline-based, amine-based, quaternary phosphonium-based, pyridinium-based, and pyrrolidinium-based ionic liquids, etc. Ionic liquids are described as green solvents due to their characteristics such as low volatility, nonflammability, thermal stability, and high solubility. Therefore, ionic liquids could be used as efficient extractants or extraction additives for extraction of phenolic compounds in liquid phase. The extraction mechanism and performance of phenolic compounds with different kinds of ionic liquids are reviewed systematically. Then, the latest research progress on extraction and separation of phenolic compounds in liquid phase by ionic liquids are comprehensively summarized. Besides, the influencing factors on extraction of phenolic compounds in liquid phase by ionic liquids are deeply analyzed. Furthermore, the existing problems and development prospect are discussed. In the future, the progress of extraction of phenolic compounds in liquid phase by ionic liquids are mainly in the following three aspects. The used ionic liquids would better have low viscosity, low water solubility, low cost, low toxicity, high stability, high extraction efficiency, high selectivity and high biodegradability. The ionic liquids and the raffinate are facile phase separation and liquids are easily reclaimed from the rich extract phase. The recycled ionic liquids could be reused multiple times and maintain good performance. The ionic liquid extractants and extractors would be highly integrated in order to build a complete extraction system and realize high extraction efficiency.

Key words: ionic liquids, extraction, separation, recovery, phenolic compounds, waste treatment

摘要：

离子液体包括咪唑类、胆碱类、铵类、季类、吡啶类、吡咯烷类等，是一种具有难挥发、不易燃、对热稳定、溶解能力强等优点的绿色溶剂，可充当高效萃取剂或萃取添加剂，用于液相中酚类物质的萃取分离。本文系统地介绍了不同类型离子液体萃取液相中酚类物质的机制和性能，全面追踪了离子液体萃取分离液相中酚类物质的最新研究进展，深入解析了离子液体萃取液相中酚类物质过程的影响因素，整体上分析了离子液体萃取液相中酚类物质存在的问题，最后展望了离子液体萃取液相中酚类物质的发展前景。未来离子液体萃取液相中酚类物质技术的发展方向为以下三个方面：一方面，开发低黏度、低水溶性、低毒性、低成本、高稳定性、高萃取率、高选择性、容易生物降解的离子液体；另一方面，离子液体容易与萃余相分离，回收后的离子液体可多次循环使用且能保持较好的萃取性能；最后，离子液体萃取剂与萃取器要高度统一、有机结合，才能达到最佳的萃取效能。

关键词: 离子液体, 萃取, 分离, 回收, 酚类物质, 废物处理

CLC Number:

TQ028.3

QI Yabing, LIU Ziyan. Research advances of extraction separation of phenolic compounds by ionic liquids[J]. Chemical Industry and Engineering Progress, 2024, 43(10): 5765-5777.

齐亚兵, 刘子炎. 离子液体萃取分离液相中酚类物质的研究进展[J]. 化工进展, 2024, 43(10): 5765-5777.

Figures/Tables 6

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离子液体	原料液	目标组分	萃取机制	萃取工艺条件	分离性能	参考文献
[Emim]SCN	甲苯+正己烷+ 对甲酚	对甲酚	[Emim]SCN的—SCN中的N与甲酚—OH中的H形成较强氢键，实现离子液体对甲酚的萃取。在间、对、邻甲酚3种甲酚异构体中，对甲酚与萃取剂形成的氢键最强	m_甲苯∶m_正己烷∶m_对甲酚=1∶7∶2，m_IL∶m_模拟油=0.2，T=298.15K， t=30min	E_对甲酚=98.25%	[17]
[Emim]Lac	甲苯+己烷+苯酚	苯酚	[Emim]Lac的—COO中的O与苯酚—OH中的H形成较强氢键，实现离子液体对苯酚的萃取	m_甲苯∶m_己烷∶m_苯酚=1∶7∶2，m_IL∶ m_模拟油=1，T=298.15K， t=30min	E_苯酚=99.9%	[18]
[Emim]OAc	异丙基苯+正庚烷+间甲酚	间甲酚	[Emim]OAc的—COO中的O与间甲酚—OH中的H形成较强氢键，实现对间甲酚的萃取	m_异丙基苯∶m_正庚烷∶m_间甲酚= 4∶2∶4，m_IL∶ m_模拟油=0.5，T=298.15K， t=60min	对间甲酚萃取率排序为[Emim]OAc/[Bmim]OAc>[Bmim]Cl>[Bmim]BF₄>[Bmim]PF₆，E_间甲酚=98.85%	[19]
[Emim]Gly、[Emim]Ala（乙腈为稀释剂）	己烷+α-生育酚+β-生育酚+γ-生育酚+δ-生育酚	生育酚	离子液体—COO中的O与生育酚—OH中的H形成较强氢键，离子液体与生育酚异构体形成氢键的强度排序为δ-生育酚>γ-生育酚>α-生育酚，实现对不同生育酚异构体的萃取	T=303.15K， n_IL∶n_乙腈=2∶98，c_δ_-生育酚=1mg/cm³， c_β_&_γ_-生育酚=0.98mg/cm³，c_α_-生育酚=0.2mg/cm³	D_δ_-生育酚=19.2~20.9， D_β_&_γ_-生育酚=9.31~10.5，D_α_-生育酚=1.51~1.55；S_δ_-生育酚/_α_-生育酚=12.7~13.5，S_β_&_γ_-生育酚/_α_-生育酚=6.2~6.8	[20]
[Bmim]Cl	己烷+苯酚或煤液化油馏分	苯酚	离子液体阴离子与苯酚之间的氢键以及咪唑环与苯环之间的π-π共轭作用实现对苯酚的萃取	c_苯酚=5048mg/L，n_IL∶n_苯酚=2~3，T=30℃，t=30min	对苯酚的萃取率排序为[Bmim]Cl>[Bmim]Br>[Bmim]BF₄>[Bmim]PF₆，E_苯酚=99%或92.5%	[21]
[Bmim]NTf₂	生物油水相馏分	苯酚、愈创木酚、4-甲基愈创木酚	[Bmim]NTf₂的阴离子[NTf₂]^-中两个S原子上的O与酚类物质—OH中的H形成较强氢键，[Bmim]NTf₂与酚类物质之间亦存在较弱的范德华力，实现对水相中酚类物质的萃取	m_IL∶m_W=0.4，t=5min	E_苯酚=95.41%，E_愈创木酚=92.04%，E_{4-甲基愈创木酚}=97.98%	[22]
[Hemim]Ac、[Hemim]Pro、[Hemim]Lac、[Hemim]Gly	甲苯+苯酚	苯酚	利用离子液体与苯酚之间的氢键作用以及离子液体咪唑环与苯酚苯环之间的π-π共轭作用实现对苯酚的萃取，氢键起主要作用	c_苯酚=0.2g/mL，n_IL∶n_苯酚=1，T=298.15K， t=60min	E_苯酚=96.06%~96.98%，离子液体的阴离子对苯酚萃取率影响较小	[23]
[OHEmim]NO₃	正己烷+ （苯酚，对甲酚，间甲酚，邻甲酚）	苯酚、对甲酚、间甲酚、邻甲酚	[OHEmim]NO₃的[OHEmim]⁺阳离子—OH中的O、阴离子NO₃^-中的O与酚类物质—OH中的H均可形成氢键，实现对酚类物质的萃取；[OHEmim]NO₃与酚类物质之间的氢键强于[HEmim]NO₃与酚类物质之间的氢键	T=298.15K， p=101.3kPa	S_{苯酚/正己烷}=857~7390，S_{邻甲酚/正己烷}=26~665， S_{间甲酚/正己烷}=241~1289，S_{对甲酚/正己烷}=135~895	[24]
DIL1、DIL2、DIL3	煤焦油	酚类	离子液体的一对阴离子Br^-与酚类物质—OH中的H之间形成氢键，实现对酚类物质的萃取	w_酚类=33.5%，m_IL∶m_酚类=0.5	与单阳离子ILs相比，DILs在油相中的溶解度小得多，热稳定性也好得多，其对苯酚的萃取能力排序为DIL3>DIL2>DIL1；DIL3对煤焦油中酚类的萃取率为93.1%	[25]
[ABZIM]Cl、[DBZIM]Cl、[BZVIM]Cl	苯酚+2,4-二硝基苯酚+2,4-二氯苯酚+芴+荧蒽+ 己烷	苯酚、2,4-二硝基苯酚、2,4-二氯苯酚	Cl^-与酚类物质—OH中的H之间的氢键作用，咪唑苯环与酚类苯环之间的π-π共轭作用，实现对酚类物质的萃取	—	离子液体的阳离子结构对苯酚的萃取率有一定的影响，萃取率排序为烯丙基>苄基>乙烯基：[ABZIM]Cl为萃取剂时E_苯酚=87.72%，E_{2,4-二硝基苯酚}=64.77%，E_{2,4-二氯苯酚}=63.47%	[26]
[C₂Mim]NTf₂、 [C₄Mim]NTf₂、 [C₈Mim]NTf₂、 [C₁₂Mim]NTf₂	苯酚溶液	苯酚	[NTf₂]^-的F与酚类物质—OH中的H之间形成强氢键，实现对酚类物质的萃取	c_苯酚=200mg/L，V_IL∶V_W=1∶3，pH=2，T=298.15K，t=3min	给定烷基链长度的离子液体对苯酚的萃取率排序为吡咯烷类>咪唑类>铵盐类；增加咪唑的烷基链长度会降低对苯酚的萃取率，E_苯酚=77%~80.9%	[27]
[CeMim]NO₃	己烷+苯+（苯酚、间甲酚、对甲酚或邻甲酚）	苯酚、间甲酚、对甲酚或邻甲酚	酚类物质的—OH与离子液体NO₃^-之间形成氢键，离子液体的羧基与酚类物质通过酸碱配位强化了二者之间的氢键，两种作用共同促进了其对酚类物质的萃取	m_己烷∶m_苯∶m_酚类=7∶1∶2，m_IL∶m_模拟油=1∶5，T=298.15K，t=30min	E_间甲酚=98.77%，E_对甲酚= 98.03%，E_邻甲酚=97.65%，E_苯酚=98.14%	[28]
[Bmim]PF₆、 [Hmim]PF₆、 [Omim]PF₆	苯酚、对苯二酚、邻甲酚或邻硝基苯酚溶液	苯酚、对苯二酚、邻甲酚、邻硝基苯酚	—	—	亲水性酚类苯酚和对苯二酚，随咪唑类离子液体阳离子碳链长度增加，对酚类物质的萃取率降低；对于疏水性酚类邻甲酚和邻硝基苯酚，情况恰好相反	[29]

离子液体	原料液	目标组分	萃取机制	萃取工艺条件	分离性能	参考文献
[Emim]SCN	甲苯+正己烷+ 对甲酚	对甲酚	[Emim]SCN的—SCN中的N与甲酚—OH中的H形成较强氢键，实现离子液体对甲酚的萃取。在间、对、邻甲酚3种甲酚异构体中，对甲酚与萃取剂形成的氢键最强	m_甲苯∶m_正己烷∶m_对甲酚=1∶7∶2，m_IL∶m_模拟油=0.2，T=298.15K， t=30min	E_对甲酚=98.25%	[17]
[Emim]Lac	甲苯+己烷+苯酚	苯酚	[Emim]Lac的—COO中的O与苯酚—OH中的H形成较强氢键，实现离子液体对苯酚的萃取	m_甲苯∶m_己烷∶m_苯酚=1∶7∶2，m_IL∶ m_模拟油=1，T=298.15K， t=30min	E_苯酚=99.9%	[18]
[Emim]OAc	异丙基苯+正庚烷+间甲酚	间甲酚	[Emim]OAc的—COO中的O与间甲酚—OH中的H形成较强氢键，实现对间甲酚的萃取	m_异丙基苯∶m_正庚烷∶m_间甲酚= 4∶2∶4，m_IL∶ m_模拟油=0.5，T=298.15K， t=60min	对间甲酚萃取率排序为[Emim]OAc/[Bmim]OAc>[Bmim]Cl>[Bmim]BF₄>[Bmim]PF₆，E_间甲酚=98.85%	[19]
[Emim]Gly、[Emim]Ala（乙腈为稀释剂）	己烷+α-生育酚+β-生育酚+γ-生育酚+δ-生育酚	生育酚	离子液体—COO中的O与生育酚—OH中的H形成较强氢键，离子液体与生育酚异构体形成氢键的强度排序为δ-生育酚>γ-生育酚>α-生育酚，实现对不同生育酚异构体的萃取	T=303.15K， n_IL∶n_乙腈=2∶98，c_δ_-生育酚=1mg/cm³， c_β_&_γ_-生育酚=0.98mg/cm³，c_α_-生育酚=0.2mg/cm³	D_δ_-生育酚=19.2~20.9， D_β_&_γ_-生育酚=9.31~10.5，D_α_-生育酚=1.51~1.55；S_δ_-生育酚/_α_-生育酚=12.7~13.5，S_β_&_γ_-生育酚/_α_-生育酚=6.2~6.8	[20]
[Bmim]Cl	己烷+苯酚或煤液化油馏分	苯酚	离子液体阴离子与苯酚之间的氢键以及咪唑环与苯环之间的π-π共轭作用实现对苯酚的萃取	c_苯酚=5048mg/L，n_IL∶n_苯酚=2~3，T=30℃，t=30min	对苯酚的萃取率排序为[Bmim]Cl>[Bmim]Br>[Bmim]BF₄>[Bmim]PF₆，E_苯酚=99%或92.5%	[21]
[Bmim]NTf₂	生物油水相馏分	苯酚、愈创木酚、4-甲基愈创木酚	[Bmim]NTf₂的阴离子[NTf₂]^-中两个S原子上的O与酚类物质—OH中的H形成较强氢键，[Bmim]NTf₂与酚类物质之间亦存在较弱的范德华力，实现对水相中酚类物质的萃取	m_IL∶m_W=0.4，t=5min	E_苯酚=95.41%，E_愈创木酚=92.04%，E_{4-甲基愈创木酚}=97.98%	[22]
[Hemim]Ac、[Hemim]Pro、[Hemim]Lac、[Hemim]Gly	甲苯+苯酚	苯酚	利用离子液体与苯酚之间的氢键作用以及离子液体咪唑环与苯酚苯环之间的π-π共轭作用实现对苯酚的萃取，氢键起主要作用	c_苯酚=0.2g/mL，n_IL∶n_苯酚=1，T=298.15K， t=60min	E_苯酚=96.06%~96.98%，离子液体的阴离子对苯酚萃取率影响较小	[23]
[OHEmim]NO₃	正己烷+ （苯酚，对甲酚，间甲酚，邻甲酚）	苯酚、对甲酚、间甲酚、邻甲酚	[OHEmim]NO₃的[OHEmim]⁺阳离子—OH中的O、阴离子NO₃^-中的O与酚类物质—OH中的H均可形成氢键，实现对酚类物质的萃取；[OHEmim]NO₃与酚类物质之间的氢键强于[HEmim]NO₃与酚类物质之间的氢键	T=298.15K， p=101.3kPa	S_{苯酚/正己烷}=857~7390，S_{邻甲酚/正己烷}=26~665， S_{间甲酚/正己烷}=241~1289，S_{对甲酚/正己烷}=135~895	[24]
DIL1、DIL2、DIL3	煤焦油	酚类	离子液体的一对阴离子Br^-与酚类物质—OH中的H之间形成氢键，实现对酚类物质的萃取	w_酚类=33.5%，m_IL∶m_酚类=0.5	与单阳离子ILs相比，DILs在油相中的溶解度小得多，热稳定性也好得多，其对苯酚的萃取能力排序为DIL3>DIL2>DIL1；DIL3对煤焦油中酚类的萃取率为93.1%	[25]
[ABZIM]Cl、[DBZIM]Cl、[BZVIM]Cl	苯酚+2,4-二硝基苯酚+2,4-二氯苯酚+芴+荧蒽+ 己烷	苯酚、2,4-二硝基苯酚、2,4-二氯苯酚	Cl^-与酚类物质—OH中的H之间的氢键作用，咪唑苯环与酚类苯环之间的π-π共轭作用，实现对酚类物质的萃取	—	离子液体的阳离子结构对苯酚的萃取率有一定的影响，萃取率排序为烯丙基>苄基>乙烯基：[ABZIM]Cl为萃取剂时E_苯酚=87.72%，E_{2,4-二硝基苯酚}=64.77%，E_{2,4-二氯苯酚}=63.47%	[26]
[C₂Mim]NTf₂、 [C₄Mim]NTf₂、 [C₈Mim]NTf₂、 [C₁₂Mim]NTf₂	苯酚溶液	苯酚	[NTf₂]^-的F与酚类物质—OH中的H之间形成强氢键，实现对酚类物质的萃取	c_苯酚=200mg/L，V_IL∶V_W=1∶3，pH=2，T=298.15K，t=3min	给定烷基链长度的离子液体对苯酚的萃取率排序为吡咯烷类>咪唑类>铵盐类；增加咪唑的烷基链长度会降低对苯酚的萃取率，E_苯酚=77%~80.9%	[27]
[CeMim]NO₃	己烷+苯+（苯酚、间甲酚、对甲酚或邻甲酚）	苯酚、间甲酚、对甲酚或邻甲酚	酚类物质的—OH与离子液体NO₃^-之间形成氢键，离子液体的羧基与酚类物质通过酸碱配位强化了二者之间的氢键，两种作用共同促进了其对酚类物质的萃取	m_己烷∶m_苯∶m_酚类=7∶1∶2，m_IL∶m_模拟油=1∶5，T=298.15K，t=30min	E_间甲酚=98.77%，E_对甲酚= 98.03%，E_邻甲酚=97.65%，E_苯酚=98.14%	[28]
[Bmim]PF₆、 [Hmim]PF₆、 [Omim]PF₆	苯酚、对苯二酚、邻甲酚或邻硝基苯酚溶液	苯酚、对苯二酚、邻甲酚、邻硝基苯酚	—	—	亲水性酚类苯酚和对苯二酚，随咪唑类离子液体阳离子碳链长度增加，对酚类物质的萃取率降低；对于疏水性酚类邻甲酚和邻硝基苯酚，情况恰好相反	[29]

离子液体	原料液	目标组分	萃取机制	萃取工艺条件	分离性能	文献
[Ch]Pro、[Ch]Lac、 [Ch]Gly、[Ch]Ac	甲苯+苯酚	苯酚	离子液体与酚类之间的氢键实现对酚类的萃取	c_苯酚=0.2g/mL，n_IL∶n_苯酚=1，T=298.15K， t=60min	在阴离子相同时，不同类型阳离子对苯酚的萃取率排序为[Ch]>[Hemim]，[Ch]Pro对苯酚的萃取率最高，为99.49%	[23]
[Ch]C₂OO、[Ch]C₈OO、 [Ch]C₁₂OO、[Ch]C₁₄OO （二甲基亚砜为稀释剂）	间甲酚+对甲酚+ 2,6-二甲酚+ 正己烷	间甲酚、对甲酚、 2,6-二甲酚	离子液体与酚类之间的氢键实现对酚类的萃取	T=25℃，V_原料液∶V_萃取剂= 1∶1，c_酚=5mg/mL，t=2h	随阴离子碳链的增长，离子液体对亲水性较强的间甲酚、对甲酚的萃取分配系数减小；离子液体对亲水性较弱的2,6-二甲酚萃取分配系数增大	[30]
[Ch]NTf₂	苯酚（愈创木酚、丁香酚、邻苯二酚）溶液	苯酚、愈创木酚、丁香酚、邻苯二酚	—	T=295.15K，p=0.1MPa，t=48h	D_苯酚=18.59~26.13，D_愈创木酚=59.55~166，D_丁香酚=92~218，D_邻苯二酚=2.07~12；S_苯酚=27.8~41.3，S_愈创木酚=175.1~232.4，S_丁香酚=165.1~309.4，S_邻苯二酚=2.6~16.8	[31]
19种羧酸胆碱类离子液体	苯酚+甲苯	苯酚	离子液体阴阳离子与酚类物质—OH之间形成氢键实现对酚类物质的萃取，阴离子的羧基与酚羟基之间的氢键起主要作用	c_苯酚=0.2g/mL，t=30min	阴离子的结构和烷基碳链长度对苯酚的萃取有重要影响；二元羧酸胆碱对苯酚的萃取率高于一元羧酸胆碱；苯酚的萃取率随阴离子烷基碳链长度增加而降低，随离子液体亲水性增加而提高；E_苯酚=86%~99%	[32]
[Ch]Lac、[Ch]Alic、 [Ch]HOCH₂COO、 [Ch]BrCOO、[Ch]Pro、 [Ch]2C₄H₆(COO)₂	苯酚+甲苯	苯酚	—	c_苯酚=0.2g/mL，t=30min	苯甲酸类胆碱取代基的种类和位置均会对苯酚的萃取产生影响，离子液体对苯酚的萃取分配系数排序为[Ch]2C₄H₆(COO)₂>[Ch]HOCH₂COO>[Ch]Lac>[Ch]Pro>[Ch]Alic>[Ch]BrCOO	[33]

离子液体	原料液	目标组分	萃取机制	萃取工艺条件	分离性能	文献
[Ch]Pro、[Ch]Lac、 [Ch]Gly、[Ch]Ac	甲苯+苯酚	苯酚	离子液体与酚类之间的氢键实现对酚类的萃取	c_苯酚=0.2g/mL，n_IL∶n_苯酚=1，T=298.15K， t=60min	在阴离子相同时，不同类型阳离子对苯酚的萃取率排序为[Ch]>[Hemim]，[Ch]Pro对苯酚的萃取率最高，为99.49%	[23]
[Ch]C₂OO、[Ch]C₈OO、 [Ch]C₁₂OO、[Ch]C₁₄OO （二甲基亚砜为稀释剂）	间甲酚+对甲酚+ 2,6-二甲酚+ 正己烷	间甲酚、对甲酚、 2,6-二甲酚	离子液体与酚类之间的氢键实现对酚类的萃取	T=25℃，V_原料液∶V_萃取剂= 1∶1，c_酚=5mg/mL，t=2h	随阴离子碳链的增长，离子液体对亲水性较强的间甲酚、对甲酚的萃取分配系数减小；离子液体对亲水性较弱的2,6-二甲酚萃取分配系数增大	[30]
[Ch]NTf₂	苯酚（愈创木酚、丁香酚、邻苯二酚）溶液	苯酚、愈创木酚、丁香酚、邻苯二酚	—	T=295.15K，p=0.1MPa，t=48h	D_苯酚=18.59~26.13，D_愈创木酚=59.55~166，D_丁香酚=92~218，D_邻苯二酚=2.07~12；S_苯酚=27.8~41.3，S_愈创木酚=175.1~232.4，S_丁香酚=165.1~309.4，S_邻苯二酚=2.6~16.8	[31]
19种羧酸胆碱类离子液体	苯酚+甲苯	苯酚	离子液体阴阳离子与酚类物质—OH之间形成氢键实现对酚类物质的萃取，阴离子的羧基与酚羟基之间的氢键起主要作用	c_苯酚=0.2g/mL，t=30min	阴离子的结构和烷基碳链长度对苯酚的萃取有重要影响；二元羧酸胆碱对苯酚的萃取率高于一元羧酸胆碱；苯酚的萃取率随阴离子烷基碳链长度增加而降低，随离子液体亲水性增加而提高；E_苯酚=86%~99%	[32]
[Ch]Lac、[Ch]Alic、 [Ch]HOCH₂COO、 [Ch]BrCOO、[Ch]Pro、 [Ch]2C₄H₆(COO)₂	苯酚+甲苯	苯酚	—	c_苯酚=0.2g/mL，t=30min	苯甲酸类胆碱取代基的种类和位置均会对苯酚的萃取产生影响，离子液体对苯酚的萃取分配系数排序为[Ch]2C₄H₆(COO)₂>[Ch]HOCH₂COO>[Ch]Lac>[Ch]Pro>[Ch]Alic>[Ch]BrCOO	[33]

离子液体	原料液	目标组分	萃取机制	萃取工艺条件	分离性能	文献
TPAC	间甲酚+异丙苯	间甲酚	Cl^-与间甲酚之间形成较强氢键实现对间甲酚的萃取	常压，T=25℃	阴离子不变时，随阳离子碳链长度的增加，季铵盐类离子液体对间甲酚的萃取效果呈先上升后下降的趋势；离子液体对间甲酚的分离性能排序为[Emim]OAc>[Bmim]OAc>TPAC>[Bmim]Cl	[8]
[HMEA]L	甲苯+正己烷+ 邻甲酚（间甲酚、对甲酚）	邻甲酚、间甲酚、对甲酚	离子液体与甲酚之间的氢键、酸碱配位和静电相互作用实现对甲酚的萃取	m_甲酚∶m_甲苯∶m_正己烷=2∶1∶7，m_IL∶m_模拟油=1∶5，T=298.15K, t=30min	E_邻甲酚=84.53%，E_间甲酚=94.44%，E_对甲酚=96.83%；D_邻甲酚=5.46，D_间甲酚=16.98，D_对甲酚=30.5	[34]
[TOA]3,4-DMB、 [TOA]4-TBB、 [TOA]4-PB	苯酚溶液	苯酚	离子液体羧酸阴离子中的O与苯酚羟基之间形成氢键实现对苯酚的萃取	V_IL∶V_W=1∶5，c_苯酚=3000mg/L，pH=5，T=298K，t=5min	[TOA]4-PB对苯酚的萃取性能最佳；E_苯酚>95%	[35]
HEDBr、HPDBr、 HBDBr	煤焦油	苯酚	离子液体与苯酚之间形成氢键实现对苯酚的萃取	n_IL∶n_苯酚=0.3，t=5min	HPDBr对苯酚的萃取率最高，E_苯酚=92.7%；双阳离子型离子液体的热稳定性更高，在原料液中的溶解度更小	[36]
[PA]FA、[PA]AC	间甲酚+己烷	间甲酚	在离子液体的氨基、羧基与间甲酚之间的氢键以及与间甲酚间的静电相互作用下实现对间甲酚的萃取	m_间甲酚∶m_己烷=2∶8，m_IL∶m_模拟油=0.2，T=298.15K	[PA]FA的萃取率更高；E_间甲酚=97.8%	[37]
[HMEA]FA、[HDEA]FA、[HTEA]FA、[HMEA]AC、[HDEA]AC、[HTEA]AC	苯酚+正己烷+甲苯	苯酚	醇胺类离子液体与苯酚之间形成氢键实现对苯酚的萃取	m_苯酚∶m_正己烷∶m_甲苯=2∶7∶1，m_IL∶m_模拟油=1∶10，T=25℃，t=20min	6种离子液体对苯酚的萃取率均大于95%；醇胺类离子液体对苯酚的萃取率大于多元醇	[38]