Screening of deep eutectic solvents and study on extraction performance for oil-hydroxybenzene separation

doi:10.11949/0438-1157.20220578

Abstract

Abstract:

The efficient separation of phenolic compounds from low-temperature coal tar is of great industrial significance. 40 deep eutectic solvents (DESs) were screened for m-cresol-cumene separation by conductor-like screening model for real solvents (COSMO-RS). The indexes of screening process included capacity, selectivity, and performance index at infinite dilution. In addition, the σ-profile and σ-potential of m-cresol, cumene, and the screened DESs were used to analyze the molecular interactions, which could interpret the high extraction performance of the screened DESs. The screening results were verified by liquid-liquid equilibrium (LLE) experiments, and the extraction process conditions were optimized. The results show that choline chloride (ChCl)∶ethylene glycol (EG) (1∶2), ChCl∶glycerol (Gly) (1∶2), ChCl∶lactic acid (LA) (1∶2) demonstrate the higher performance index and are preliminarily screened as extractants. There is a strong hydrogen bond between 3 screened DESs and m-cresol, as well as a repulsive interaction between 3 screened DESs and cumene. Both COSMO-RS calculation and LLE experimental results show that ChCl∶EG (1∶2) presents the highest distribution coefficient and selectivity. Moreover, ChCl∶EG (1∶2) has the lowest viscosity, which is selected as the most suitable extractant for m-cresol-cumene separation. When the temperature and the mass ratio of ChCl∶EG (1∶2) to model oil are 25℃ and 1∶1, respectively, the ChCl∶EG (1∶2) can extract 98.41% of the m-cresol with only 8.41% entrained cumene, and ChCl∶EG (1∶2) has good recycling performance.

Key words: deep eutectic solvents, extraction, COSMO-RS model, m-cresol-cumene separation, phase equilibria, experimental validation

摘要：

低温煤焦油中酚类化合物的高效分离在工业上具有重要意义。采用COSMO-RS模型对40种用于间甲酚-异丙苯分离的低共熔溶剂进行筛选，结合σ-profile和σ-potential对筛选得到的低共熔溶剂的高萃取性能进行分析。并采用液液相平衡实验对筛选结果进行验证，优化了萃取工艺条件。结果表明，COSMO-RS模型筛选得到的氯化胆碱(ChCl)∶乙二醇(EG)(1∶2)、ChCl∶丙三醇(Gly)(1∶2)、ChCl∶乳酸(LA)(1∶2)三种低共熔溶剂与间甲酚之间存在较强的氢键相互作用，与异丙苯之间存在排斥作用。液液相平衡实验证实了COSMO-RS筛选结果的可靠性，其中ChCl∶EG(1∶2)具有最高的分配系数和选择性系数，且黏度最低，被选定为最佳的低共熔溶剂。在25℃、ChCl∶EG(1∶2)与模型油质量比为1∶1时，ChCl∶EG(1∶2)对间甲酚萃取率高达98.41%，同时异丙苯夹带量仅为8.41%，并且具有良好的循环使用性能。

关键词: 低共熔溶剂, 萃取, COSMO-RS模型, 间甲酚-异丙苯分离, 相平衡, 实验验证

CLC Number:

TQ 028.4

Qian LIU, Xianglan ZHANG, Zhiping LI, Yulong LI, Mengxing HAN. Screening of deep eutectic solvents and study on extraction performance for oil-hydroxybenzene separation[J]. CIESC Journal, 2022, 73(9): 3915-3928.

刘潜, 张香兰, 李志平, 李玉龙, 韩梦醒. 油酚分离过程低共熔溶剂的筛选及萃取性能研究[J]. 化工学报, 2022, 73(9): 3915-3928.

Figures/Tables 19

References 45

1	Jiao T T, Li C S, Zhuang X L, et al. The new liquid-liquid extraction method for separation of phenolic compounds from coal tar[J]. Chemical Engineering Journal, 2015, 266: 148-155.
2	Jiao T T, Wang H Y, Dai F, et al. Thermodynamics study on the separation process of cresols from hexane via deep eutectic solvent formation[J]. Industrial & Engineering Chemistry Research, 2016, 55(32): 8848-8857.
3	Gai H J, Qiao L, Zhong C Y, et al. A solvent based separation method for phenolic compounds from low-temperature coal tar[J]. Journal of Cleaner Production, 2019, 223: 1-11.
4	刘潜, 何天琦, 刘小菡, 等. 乙二醇-尿素复配溶剂萃取分离模拟油酚混合物[J]. 化学工业与工程, 2020, 37(4): 23-29.
	Liu Q, He T Q, Liu X H, et al. Extraction of phenolic compounds from model oil with glycol-urea composite extractant[J]. Chemical Industry and Engineering, 2020, 37(4): 23-29.
5	Liu X K, Zhang X L. Solvent screening and liquid-liquid measurement for extraction of phenols from aromatic hydrocarbon mixtures[J]. The Journal of Chemical Thermodynamics, 2019, 129: 12-21.
6	Jiao T T, Gong M M, Zhuang X L, et al. A new separation method for phenolic compounds from low-temperature coal tar with urea by complex formation[J]. Journal of Industrial and Engineering Chemistry, 2015, 29: 344-348.
7	彭艳枚, 崔现宝, 张缨, 等. 甲醇-乙酸甲酯-1-丁基-3-甲基咪唑双三氟甲磺酰亚胺盐的等压汽液平衡[J]. 化学工业与工程, 2013, 30(6): 27-31.
	Peng Y M, Cui X B, Zhang Y, et al. Isobaric vapor-liquid equilibrium for methanol-methyl acetate-1-butyl-3-methylimidazolium bis[(trifluoromethyl) sulfonyl]imide at 101.3 kPa[J]. Chemical Industry and Engineering, 2013, 30(6): 27-31.
8	Hou Y C, Ren Y H, Peng W, et al. Separation of phenols from oil using imidazolium-based ionic liquids[J]. Industrial & Engineering Chemistry Research, 2013, 52(50): 18071-18075.
9	Yao C F, Hou Y C, Ren S H, et al. Efficient separation of phenolic compounds from model oils by dual-functionalized ionic liquids[J]. Chemical Engineering and Processing-Process Intensification, 2018, 128: 216-222.
10	李文秀, 张羽, 曹颖, 等. 离子液体用于四氢呋喃-乙醇-水三元共沸物系分离的研究[J]. 化工学报, 2020, 71(4): 1676-1682.
	Li W X, Zhang Y, Cao Y, et al. Study on separation of tetrahydrofuran-ethanol-water ternary azeotrope system by ionic liquid[J]. CIESC Journal, 2020, 71(4): 1676-1682.
11	Jiao T T, Qin X Z, Zhang H W, et al. Separation of phenol and pyridine from coal tar via liquid-liquid extraction using deep eutectic solvents[J]. Chemical Engineering Research and Design, 2019, 145: 112-121.
12	Li G S, Xie Q, Liu Q, et al. Separation of phenolic compounds from oil mixtures by betaine-based deep eutectic solvents[J]. Asia-Pacific Journal of Chemical Engineering, 2020, 15(6): e2515.
13	Yi L, Feng J, Li W Y, et al. High-performance separation of phenolic compounds from coal-based liquid oil by deep eutectic solvents[J]. ACS Sustainable Chemistry & Engineering, 2019, 7(8): 7777-7783.
14	Liu Q, Zhang X L. Systematic method of screening deep eutectic solvents as extractive solvents for m-cresol/cumene separation[J]. Separation and Purification Technology, 2022, 291: 120853.
15	Song Z, Hu X T, Wu H Y, et al. Systematic screening of deep eutectic solvents as sustainable separation media exemplified by the CO₂ capture process[J]. ACS Sustainable Chemistry & Engineering, 2020, 8(23): 8741-8751.
16	Lei Z G, Zhang J G, Li Q S, et al. UNIFAC model for ionic liquids[J]. Industrial & Engineering Chemistry Research, 2009, 48(5): 2697-2704.
17	Lei Z G, Dai C N, Liu X, et al. Extension of the UNIFAC model for ionic liquids[J]. Industrial & Engineering Chemistry Research, 2012, 51(37): 12135-12144.
18	董一春. 离子液体预测型热力学模型及其在萃取精馏分离甲缩醛和甲醇中的应用[D]. 北京: 北京化工大学, 2020.
	Dong Y C. Predictive thermodynamics models for ionic liquids and their application in the separation of methylal and methanol mixture by extractive distillation[D]. Beijing: Beijing University of Chemical Technology, 2020.
19	Chen G Z, Song Z, Qi Z W, et al. Neural recommender system for the activity coefficient prediction and UNIFAC model extension of ionic liquid-solute systems[J]. AIChE Journal, 2021, 67(4): e17171.
20	Song Z, Zhang C Y, Qi Z W, et al. Computer-aided design of ionic liquids as solvents for extractive desulfurization[J]. AIChE Journal, 2018, 64(3): 1013-1025.
21	Chao H, Song Z, Cheng H Y, et al. Computer-aided design and process evaluation of ionic liquids for n-hexane-methylcyclopentane extractive distillation[J]. Separation and Purification Technology, 2018, 196: 157-165.
22	Song Z, Li X X, Chao H, et al. Computer-aided ionic liquid design for alkane/cycloalkane extractive distillation process[J]. Green Energy & Environment, 2019, 4(2): 154-165.
23	Klamt A, Eckert F. COSMO-RS: a novel and efficient method for the a priori prediction of thermophysical data of liquids[J]. Fluid Phase Equilibria, 2000, 172(1): 43-72.
24	陈燕鑫, 童赛, 张美景, 等. 基于COSMO-RS模型L-丙氨酸-L-谷胺酰胺结晶溶剂的筛选及其溶液热力学性质研究[J]. 化学工业与工程, 2016, 33(3): 31-38.
	Chen Y X, Tong S, Zhang M J, et al. Solvent screening via COSMO-RS model and measurement of solution thermodynamics for crystallization of N-(2)-L-alanyl-L-glutamine[J]. Chemical Industry and Engineering, 2016, 33(3): 31-38.
25	刘潜, 张香兰, 李巍. 基于COSMO-RS模型的分离油酚混合物的离子液体萃取剂筛选[J]. 化工学报, 2018, 69(12): 5100-5111.
	Liu Q, Zhang X L, Li W. Screening ionic liquids solvent for separation of oil and hydroxybenzene mixtures based on COSMO-RS model[J]. CIESC Journal, 2018, 69(12): 5100-5111.
26	Hizaddin H F, Ramalingam A, Hashim M A, et al. Evaluating the performance of deep eutectic solvents for use in extractive denitrification of liquid fuels by the conductor-like screening model for real solvents[J]. Journal of Chemical & Engineering Data, 2014, 59(11): 3470-3487.
27	Hadj-Kali M K, Hizaddin H F, Wazeer I, et al. Liquid-liquid separation of azeotropic mixtures of ethanol/alkanes using deep eutectic solvents: COSMO-RS prediction and experimental validation[J]. Fluid Phase Equilibria, 2017, 448: 105-115.
28	成洪业, 漆志文. 低共熔溶剂用于萃取分离的研究进展[J]. 化工进展, 2020, 39(12): 4896-4907.
	Cheng H Y, Qi Z W. Research progress of deep eutectic solvent for extractive separation[J]. Chemical Industry and Engineering Progress, 2020, 39(12): 4896-4907.
29	吴明尧. 基于季铵盐低共熔溶剂的柑橘精油脱萜过程研究[D]. 上海: 华东理工大学, 2021.
	Wu M Y. Extractive deterpenation of citrus essential oils using quaternary ammonium-based deep eutectic solvents[D]. Shanghai: East China University of Science and Technology, 2021.
30	张志刚, 张德彪, 张亲亲, 等. 基于COSMO-RS方法筛选离子液体分离乙酸乙酯-乙腈共沸物[J]. 化工学报, 2019, 70(1): 146-153.
	Zhang Z G, Zhang D B, Zhang Q Q, et al. Screening of ionic liquids for separation of ethyl acetate-acetonitrile azeotrope based on COSMO-RS[J]. CIESC Journal, 2019, 70(1): 146-153.
31	李军芳, 毛学锋, 胡发亭. 中低温煤焦油酚油馏分中酚类化合物的组成[J]. 煤炭转化, 2019, 42(2): 32-38.
	Li J F, Mao X F, Hu F T. Composition of phenolic compounds in phenol oil distillate of medium and low temperature coal tar[J]. Coal Conversion, 2019, 42(2): 32-38.
32	易兰. 煤直接转化液体产物中芳香族化合物缔合结构解析与组分分离[D]. 杭州: 浙江大学, 2020.
	Yi L. Association structure analysis and component separation of aromatic compounds in liquid products from direct coal conversion[D]. Hangzhou: Zhejiang University, 2020.
33	Ji Y A, Hou Y C, Ren S H, et al. Highly efficient separation of phenolic compounds from oil mixtures by imidazolium-based dicationic ionic liquids via forming deep eutectic solvents[J]. Energy & Fuels, 2017, 31(9): 10274-10282.
34	Liu Q, Zhang X L, Li W. 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.
35	李明宴, 李进龙, 彭昌军, 等. 基于COSMO-SAC模型研究离子液体对氨水溶液汽液平衡的影响[J]. 化工学报, 2022, 73(3): 1044-1053.
	Li M Y, Li J L, Peng C J, et al. The effect of ionic liquids on the vapor-liquid equilibrium of ammonia-water solution by the COSMO-SAC[J]. CIESC Journal, 2022, 73(3): 1044-1053.
36	Salleh Z, Wazeer I, Mulyono S, et al. Efficient removal of benzene from cyclohexane-benzene mixtures using deep eutectic solvents-COSMO-RS screening and experimental validation[J]. The Journal of Chemical Thermodynamics, 2017, 104: 33-44.
37	Cheng H Y, Liu C Y, Zhang J J, et al. Screening deep eutectic solvents for extractive desulfurization of fuel based on COSMO-RS model[J]. Chemical Engineering and Processing-Process Intensification, 2018, 125: 246-252.
38	Wu Z M, Liu C Y, Cheng H Y, et al. Tuned extraction and regeneration process for separation of hydrophobic compounds by aqueous ionic liquid[J]. Journal of Molecular Liquids, 2020, 308: 113032.
39	Yao C F, Hou Y C, Ren S H, et al. Selective extraction of aromatics from aliphatics using dicationic ionic liquid-solvent composite extractants[J]. Journal of Molecular Liquids, 2019, 291: 111267.
40	方静, 张淑婷, 李婷婷, 等. 离子液体用于燃油萃取脱硫的选择与过程优化[J]. 化工学报, 2017, 68(9): 3434-3441.
	Fang J, Zhang S T, Li T T, et al. Selection and process optimization of ionic liquids for desulfurization[J]. CIESC Journal, 2017, 68(9): 3434-3441.
41	Yao C F, Hou Y C, Ren S H, et al. Efficient separation of phenol from model oils using environmentally benign quaternary ammonium-based zwitterions via forming deep eutectic solvents[J]. Chemical Engineering Journal, 2017, 326: 620-626.
42	Ji Y A, Hou Y C, Ren S H, et al. Separation of phenolic compounds from oil mixtures using environmentally benign biological reagents based on Brønsted acid-Lewis base interaction[J]. Fuel, 2019, 239: 926-934.
43	Wu Z M, Zeng Q, Cheng H Y, et al. Extractive separation of tetralin-dodecane mixture using tetrabutylphosphonium bromide-based deep eutectic solvent[J]. Chemical Engineering and Processing-Process Intensification, 2020, 149: 107822.
44	Guo W J, Hou Y C, Wu W Z, et al. Separation of phenol from model oils with quaternary ammonium salts via forming deep eutectic solvents[J]. Green Chemistry, 2013, 15(1): 226-229.
45	Liu Q, Zhang X L. Highly efficient separation of phenolic compounds from low-temperature coal tar by composite extractants with low viscosity[J]. Journal of Molecular Liquids, 2022, 360: 119417.

HBA	HBD	HBA∶HBD(molar ratio)	Abbreviation
choline chloride	ethylene glycol	1∶2	ChCl∶EG (1∶2)
choline chloride	glycerol	1∶2	ChCl∶Gly (1∶2)
choline chloride	tetraethylene glycol	1∶3	ChCl∶TEG (1∶3)
choline chloride	xylitol	1∶2	ChCl∶Xy (1∶2)
choline chloride	D-sorbitol	1∶2	ChCl∶Ds (1∶2)
choline chloride	2,2,2-trifluoroacetamide	1∶2	ChCl∶TFA (1∶2)
choline chloride	trifluoroacetic acid	1∶2	ChCl∶TrFA (1∶2)
choline chloride	p-toluenesulfonic acid	1∶2	ChCl∶PTSA (1∶2)
choline chloride	lactic acid	1∶2	ChCl∶LA (1∶2)
choline chloride	lactic acid	1∶3	ChCl∶LA (1∶3)
choline chloride	lactic acid	1∶4	ChCl∶LA (1∶4)
choline chloride	lactic acid	1∶5	ChCl∶LA (1∶5)
choline chloride	lactic acid	1∶6	ChCl∶LA (1∶6)
choline chloride	oxalic acid	1∶2	ChCl∶OA (1∶2)
choline chloride	malonic acid	1∶2	ChCl∶MA (1∶2)
choline chloride	malic acid	1∶2	ChCl∶MAA (1∶2)
choline bromide	glycerol	1∶2	ChBr∶Gly (1∶2)
choline bromide	trifluoroacetic acid	1∶2	ChBr∶TrFA (1∶2)
betaine hydrochloride	glycerol	1∶2	BHC∶Gly (1∶2)
betaine hydrochloride	trifluoroacetic acid	1∶2	BHC∶TrFA (1∶2)
tetraethylammonium chloride	glycerol	1∶5	TEAC∶Gly (1∶5)
tetraethylammonium chloride	D-sorbitol	1∶3	TEAC∶Ds (1∶3)
tetraethylammonium chloride	2,2,2-trifluoroacetamide	1∶3	TEAC∶TFA (1∶3)
tetraethylammonium chloride	benzoic acid	1∶4	TEAC∶BA (1∶4)
tetraethylammonium chloride	oxalic acid	1∶3	TEAC∶OA (1∶3)
tetraethylammonium bromide	ethylene glycol	1∶4	TEAB∶EG (1∶4)
tetraethylammonium bromide	glycerol	1∶4	TEAB∶Gly (1∶4)
tetraethylammonium bromide	trifluoroacetic acid	1∶4	TEAB∶TrFA (1∶4)
tetraethylammonium bromide	glutaric acid	1∶4	TEAB∶GA (1∶4)
tetraethylammonium bromide	benzoic acid	1∶4	TEAB∶BA (1∶4)
tetraethylammonium bromide	levulinic acid	1∶4	TEAB∶LEA (1∶4)
tetraethylammonium bromide	oxalic acid	1∶4	TEAB∶OA (1∶4)
tetrabutylammonium bromide	ethylene glycol	1∶4	TBAB∶EG (1∶4)
tetrabutylammonium bromide	benzoic acid	1∶4	TBAB∶BA (1∶4)
tetrabutylammonium bromide	levulinic acid	1∶4	TBAB∶LEA (1∶4)
tetrabutylphosphonium bromide	ethylene glycol	1∶4	TBPB∶EG (1∶4)
tetrabutylphosphonium bromide	benzoic acid	1∶4	TBPB∶BA (1∶4)
benzyltrimethylammonium chloride	glycerol	1∶4	BTMAC∶Gly (1∶4)
benzyltrimethylammonium chloride	glycerol	1∶5	BTMAC∶Gly (1∶5)
benzyltrimethylammonium chloride	glycerol	1∶6	BTMAC∶Gly (1∶6)

HBA	HBD	HBA∶HBD(molar ratio)	Abbreviation
choline chloride	ethylene glycol	1∶2	ChCl∶EG (1∶2)
choline chloride	glycerol	1∶2	ChCl∶Gly (1∶2)
choline chloride	tetraethylene glycol	1∶3	ChCl∶TEG (1∶3)
choline chloride	xylitol	1∶2	ChCl∶Xy (1∶2)
choline chloride	D-sorbitol	1∶2	ChCl∶Ds (1∶2)
choline chloride	2,2,2-trifluoroacetamide	1∶2	ChCl∶TFA (1∶2)
choline chloride	trifluoroacetic acid	1∶2	ChCl∶TrFA (1∶2)
choline chloride	p-toluenesulfonic acid	1∶2	ChCl∶PTSA (1∶2)
choline chloride	lactic acid	1∶2	ChCl∶LA (1∶2)
choline chloride	lactic acid	1∶3	ChCl∶LA (1∶3)
choline chloride	lactic acid	1∶4	ChCl∶LA (1∶4)
choline chloride	lactic acid	1∶5	ChCl∶LA (1∶5)
choline chloride	lactic acid	1∶6	ChCl∶LA (1∶6)
choline chloride	oxalic acid	1∶2	ChCl∶OA (1∶2)
choline chloride	malonic acid	1∶2	ChCl∶MA (1∶2)
choline chloride	malic acid	1∶2	ChCl∶MAA (1∶2)
choline bromide	glycerol	1∶2	ChBr∶Gly (1∶2)
choline bromide	trifluoroacetic acid	1∶2	ChBr∶TrFA (1∶2)
betaine hydrochloride	glycerol	1∶2	BHC∶Gly (1∶2)
betaine hydrochloride	trifluoroacetic acid	1∶2	BHC∶TrFA (1∶2)
tetraethylammonium chloride	glycerol	1∶5	TEAC∶Gly (1∶5)
tetraethylammonium chloride	D-sorbitol	1∶3	TEAC∶Ds (1∶3)
tetraethylammonium chloride	2,2,2-trifluoroacetamide	1∶3	TEAC∶TFA (1∶3)
tetraethylammonium chloride	benzoic acid	1∶4	TEAC∶BA (1∶4)
tetraethylammonium chloride	oxalic acid	1∶3	TEAC∶OA (1∶3)
tetraethylammonium bromide	ethylene glycol	1∶4	TEAB∶EG (1∶4)
tetraethylammonium bromide	glycerol	1∶4	TEAB∶Gly (1∶4)
tetraethylammonium bromide	trifluoroacetic acid	1∶4	TEAB∶TrFA (1∶4)
tetraethylammonium bromide	glutaric acid	1∶4	TEAB∶GA (1∶4)
tetraethylammonium bromide	benzoic acid	1∶4	TEAB∶BA (1∶4)
tetraethylammonium bromide	levulinic acid	1∶4	TEAB∶LEA (1∶4)
tetraethylammonium bromide	oxalic acid	1∶4	TEAB∶OA (1∶4)
tetrabutylammonium bromide	ethylene glycol	1∶4	TBAB∶EG (1∶4)
tetrabutylammonium bromide	benzoic acid	1∶4	TBAB∶BA (1∶4)
tetrabutylammonium bromide	levulinic acid	1∶4	TBAB∶LEA (1∶4)
tetrabutylphosphonium bromide	ethylene glycol	1∶4	TBPB∶EG (1∶4)
tetrabutylphosphonium bromide	benzoic acid	1∶4	TBPB∶BA (1∶4)
benzyltrimethylammonium chloride	glycerol	1∶4	BTMAC∶Gly (1∶4)
benzyltrimethylammonium chloride	glycerol	1∶5	BTMAC∶Gly (1∶5)
benzyltrimethylammonium chloride	glycerol	1∶6	BTMAC∶Gly (1∶6)

Raffinate phase			Extract phase			D	S
w₁	w₂	w₃	w'₁	w'₂	w'₃	D	S
1. {[ChCl∶EG (1∶2)] (1) + m-cresol (2) + cumene (3)}
0.0000	0.0041	0.9959	0.8481	0.1241	0.0278	30.27	1083.20
0.0000	0.0054	0.9946	0.8099	0.1589	0.0312	29.42	936.75
0.0003	0.0066	0.9931	0.7768	0.1899	0.0333	28.77	856.59
0.0006	0.0078	0.9916	0.7426	0.2188	0.0386	28.06	721.56
0.0012	0.0089	0.9899	0.7103	0.2445	0.0452	27.48	602.79
0.0022	0.0099	0.9879	0.6810	0.2687	0.0503	27.14	532.90
0.0031	0.0108	0.9861	0.6530	0.2908	0.0562	26.93	473.02
0.0039	0.0116	0.9845	0.6265	0.3105	0.0630	26.77	418.09
2. {[ChCl∶Gly (1∶2)] (1) + m-cresol (2) + cumene (3)}
0.0000	0.0081	0.9919	0.8561	0.1223	0.0216	15.10	694.44
0.0001	0.0108	0.9891	0.8194	0.1566	0.0240	14.50	596.87
0.0005	0.0136	0.9859	0.7860	0.1881	0.0259	13.83	526.02
0.0009	0.0162	0.9829	0.7530	0.2170	0.0300	13.39	439.20
0.0017	0.0188	0.9795	0.7227	0.2443	0.0330	12.99	385.42
0.0029	0.0211	0.9760	0.6911	0.2689	0.0400	12.74	310.60
0.0041	0.0237	0.9722	0.6626	0.2906	0.0468	12.26	254.86
0.0056	0.0257	0.9687	0.6333	0.3105	0.0562	12.08	208.30
3. {[ChCl∶LA (1∶2)] (1) + m-cresol (2) + cumene (3)}
0.0000	0.0086	0.9914	0.8528	0.1226	0.0246	14.25	573.41
0.0002	0.0115	0.9883	0.8137	0.1568	0.0295	13.63	456.49
0.0006	0.0141	0.9853	0.7782	0.1862	0.0356	13.20	365.12
0.0010	0.0168	0.9822	0.7407	0.2155	0.0438	12.83	287.50
0.0019	0.0195	0.9786	0.7088	0.2408	0.0504	12.35	239.88
0.0029	0.0219	0.9752	0.6749	0.2636	0.0615	12.04	190.76
0.0044	0.0241	0.9715	0.6439	0.2830	0.0731	11.74	156.06
0.0058	0.0260	0.9682	0.6095	0.3002	0.0903	11.55	123.84

Raffinate phase			Extract phase			D	S
w₁	w₂	w₃	w'₁	w'₂	w'₃	D	S
1. {[ChCl∶EG (1∶2)] (1) + m-cresol (2) + cumene (3)}
0.0000	0.0041	0.9959	0.8481	0.1241	0.0278	30.27	1083.20
0.0000	0.0054	0.9946	0.8099	0.1589	0.0312	29.42	936.75
0.0003	0.0066	0.9931	0.7768	0.1899	0.0333	28.77	856.59
0.0006	0.0078	0.9916	0.7426	0.2188	0.0386	28.06	721.56
0.0012	0.0089	0.9899	0.7103	0.2445	0.0452	27.48	602.79
0.0022	0.0099	0.9879	0.6810	0.2687	0.0503	27.14	532.90
0.0031	0.0108	0.9861	0.6530	0.2908	0.0562	26.93	473.02
0.0039	0.0116	0.9845	0.6265	0.3105	0.0630	26.77	418.09
2. {[ChCl∶Gly (1∶2)] (1) + m-cresol (2) + cumene (3)}
0.0000	0.0081	0.9919	0.8561	0.1223	0.0216	15.10	694.44
0.0001	0.0108	0.9891	0.8194	0.1566	0.0240	14.50	596.87
0.0005	0.0136	0.9859	0.7860	0.1881	0.0259	13.83	526.02
0.0009	0.0162	0.9829	0.7530	0.2170	0.0300	13.39	439.20
0.0017	0.0188	0.9795	0.7227	0.2443	0.0330	12.99	385.42
0.0029	0.0211	0.9760	0.6911	0.2689	0.0400	12.74	310.60
0.0041	0.0237	0.9722	0.6626	0.2906	0.0468	12.26	254.86
0.0056	0.0257	0.9687	0.6333	0.3105	0.0562	12.08	208.30
3. {[ChCl∶LA (1∶2)] (1) + m-cresol (2) + cumene (3)}
0.0000	0.0086	0.9914	0.8528	0.1226	0.0246	14.25	573.41
0.0002	0.0115	0.9883	0.8137	0.1568	0.0295	13.63	456.49
0.0006	0.0141	0.9853	0.7782	0.1862	0.0356	13.20	365.12
0.0010	0.0168	0.9822	0.7407	0.2155	0.0438	12.83	287.50
0.0019	0.0195	0.9786	0.7088	0.2408	0.0504	12.35	239.88
0.0029	0.0219	0.9752	0.6749	0.2636	0.0615	12.04	190.76
0.0044	0.0241	0.9715	0.6439	0.2830	0.0731	11.74	156.06
0.0058	0.0260	0.9682	0.6095	0.3002	0.0903	11.55	123.84

System	Extractant^①	T/℃	η/(mPa·s)	E/%	N/%
m-cresol (30%) + cumene (70%)	ChCl∶EG (1∶2)	25	43.87	98.41	8.41
m-cresol (30%) + cumene (70%)	[emim][HSO₄]∶EG (1∶2)	25	51.81	98.11	8.34
m-cresol (30%) + cumene (70%)	[emim][HSO₄]∶Gly (1∶2)	25	317	95.17	7.06
m-cresol (30%) + cumene (70%)	[emim][HSO₄]	25	1172	98.25	7.28
m-cresol (30%) + cumene (70%)	[emim][OAc]	25	132.9	99.5	26.93
m-cresol (30%) + cumene (70%)	[bmim][PF₆]	25	366	89.59	27.67