油酚分离过程低共熔溶剂的筛选及萃取性能研究

doi:10.11949/0438-1157.20220578

摘要/Abstract

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

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

中图分类号:

TQ 028.4

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.

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.

图/表 19

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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