Solvents selection for separation of biphenyl from FCC diesel: experimental and computational thermodynamics

doi:10.11949/0438-1157.20221304

Abstract

Abstract:

For the biphenyl-dodecane system, the COSMO-RS model was used to predict the infinite dilution activity coefficients of biphenyl and dodecane in different ionic liquids. The separation performance of ionic liquids was evaluated and screened by several indicators, and 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIM][BF₄]) was considered as the most potential extractant. The ternary liquid-liquid equilibrium data of biphenyl-dodecane-extractant systems at atmospheric pressure and 303.2 K were measured by liquid-liquid equilibrium experiment. With dimethyl sulfoxide and furfural as benchmark extractants, the separation performance of [BMIM][BF₄] as extractants was evaluated. Finally, the computational chemistry theory was used to explore the separation mechanism of different extractants for biphenyl-dodecane system. The C—H…π interaction, π-π interaction and hydrogen bond interaction are considered to be the most important interactions between the extractant and biphenyl.

Key words: extraction, phase equilibria, thermodynamics properties, ionic liquids, predictive molecular thermodynamics

摘要：

针对联苯-正十二烷分离体系，首先采用COSMO-RS模型预测了联苯和正十二烷在不同离子液体中的无限稀释活度系数，通过溶解能力和选择性两个指标对离子液体的分离性能进行了评估和筛选，1-丁基-3-甲基咪唑四氟硼酸盐（[BMIM][BF₄]）被认为是最有潜力的萃取剂。液-液相平衡实验测定了常压、温度为303.2 K条件下，联苯-正十二烷-萃取剂的三元液液相平衡数据。以二甲基亚砜（DMSO）和糠醛为基准萃取剂，评估了[BMIM][BF₄]作为萃取剂的分离性能。最后，计算化学理论被用于探究不同萃取剂用于联苯-正十二烷体系的分离机理。C—H…π相互作用、π-π相互作用和氢键作用被认为是萃取剂与联苯之间最主要的相互作用。

关键词: 萃取, 相平衡, 热力学性质, 离子液体, 预测型分子热力学

CLC Number:

TQ 028.3

Tengfei GAO, Guoxuan LI, Zhigang LEI. Solvents selection for separation of biphenyl from FCC diesel: experimental and computational thermodynamics[J]. CIESC Journal, 2022, 73(12): 5314-5323.

高腾飞, 李国选, 雷志刚. 从催化裂化柴油中分离联苯的溶剂筛选：实验和计算热力学[J]. 化工学报, 2022, 73(12): 5314-5323.

Figures/Tables 6

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阳离子			阴离子
编号	名称	阳结构式	编号	名称	结构式
C01	[MMIM]⁺		A01	[Ac]^-
C02	[EMIM]⁺		A02	[NO₃] ^-
C03	[EEIM]⁺		A03	[Tf₂N] ^-
C04	[OMIM]⁺		A04	[SCN] ^-
C05	[BMIM]⁺		A05	[DCA] ^-
C06	[HMIM]⁺		A06	[BF₄] ^-
C07	[C₂OHMIM]⁺		A07	[PF₆] ^-

阳离子			阴离子
编号	名称	阳结构式	编号	名称	结构式
C01	[MMIM]⁺		A01	[Ac]^-
C02	[EMIM]⁺		A02	[NO₃] ^-
C03	[EEIM]⁺		A03	[Tf₂N] ^-
C04	[OMIM]⁺		A04	[SCN] ^-
C05	[BMIM]⁺		A05	[DCA] ^-
C06	[HMIM]⁺		A06	[BF₄] ^-
C07	[C₂OHMIM]⁺		A07	[PF₆] ^-

萃余相			萃取相			D	S
w₁	w₂	w₃	w₁	w₂	w₃	D	S
正十二烷 (1) + 联苯 (2) + [BMIM][BF₄] (3)
0.3100	0.6781	0.0119	0.0025	0.2537	0.7438	0.37	46.40
0.4220	0.5731	0.0049	0.0024	0.2290	0.7686	0.40	69.09
0.5133	0.4845	0.0022	0.0023	0.2041	0.7936	0.42	93.21
0.6013	0.3975	0.0011	0.0022	0.1783	0.8196	0.45	125.44
0.6835	0.3159	0.0006	0.0019	0.1472	0.8509	0.47	164.14
0.7892	0.2104	0.0004	0.0017	0.1170	0.8813	0.56	253.61
0.8771	0.1227	0.0002	0.0015	0.0810	0.9174	0.66	376.04
0.9482	0.0516	0.0001	0.0014	0.0526	0.9460	1.02	704.84
正十二烷 (1) + 联苯 (2) + 糠醛 (3)
0.7779	0.1784	0.0437	0.0425	0.4188	0.5387	2.35	42.95
0.7971	0.1605	0.0425	0.0370	0.3831	0.5799	2.39	51.37
0.8174	0.1415	0.0412	0.0320	0.3432	0.6249	2.43	62.01
0.8389	0.1213	0.0398	0.0273	0.2987	0.6740	2.46	75.60
0.8618	0.0999	0.0384	0.0231	0.2494	0.7275	2.50	93.09
0.8860	0.0771	0.0369	0.0194	0.1950	0.7857	2.53	115.87
0.9118	0.0529	0.0354	0.0160	0.1354	0.8486	2.56	145.79
0.9390	0.0272	0.0338	0.0131	0.0704	0.9165	2.59	185.31
正十二烷 (1) + 联苯 (2) + DMSO (3)
0.8841	0.1054	0.0105	0.0325	0.3892	0.5784	3.69	100.55
0.9008	0.0891	0.0101	0.0320	0.3506	0.6174	3.94	110.91
0.9175	0.0727	0.0098	0.0320	0.3079	0.6601	4.23	121.32
0.9340	0.0566	0.0095	0.0328	0.2605	0.7068	4.61	131.26
0.9499	0.0409	0.0092	0.0345	0.2074	0.7581	5.08	139.85
0.9651	0.0259	0.0090	0.0376	0.1475	0.8148	5.69	145.98
0.9790	0.0122	0.0089	0.0430	0.0791	0.8779	6.51	148.38

萃余相			萃取相			D	S
w₁	w₂	w₃	w₁	w₂	w₃	D	S
正十二烷 (1) + 联苯 (2) + [BMIM][BF₄] (3)
0.3100	0.6781	0.0119	0.0025	0.2537	0.7438	0.37	46.40
0.4220	0.5731	0.0049	0.0024	0.2290	0.7686	0.40	69.09
0.5133	0.4845	0.0022	0.0023	0.2041	0.7936	0.42	93.21
0.6013	0.3975	0.0011	0.0022	0.1783	0.8196	0.45	125.44
0.6835	0.3159	0.0006	0.0019	0.1472	0.8509	0.47	164.14
0.7892	0.2104	0.0004	0.0017	0.1170	0.8813	0.56	253.61
0.8771	0.1227	0.0002	0.0015	0.0810	0.9174	0.66	376.04
0.9482	0.0516	0.0001	0.0014	0.0526	0.9460	1.02	704.84
正十二烷 (1) + 联苯 (2) + 糠醛 (3)
0.7779	0.1784	0.0437	0.0425	0.4188	0.5387	2.35	42.95
0.7971	0.1605	0.0425	0.0370	0.3831	0.5799	2.39	51.37
0.8174	0.1415	0.0412	0.0320	0.3432	0.6249	2.43	62.01
0.8389	0.1213	0.0398	0.0273	0.2987	0.6740	2.46	75.60
0.8618	0.0999	0.0384	0.0231	0.2494	0.7275	2.50	93.09
0.8860	0.0771	0.0369	0.0194	0.1950	0.7857	2.53	115.87
0.9118	0.0529	0.0354	0.0160	0.1354	0.8486	2.56	145.79
0.9390	0.0272	0.0338	0.0131	0.0704	0.9165	2.59	185.31
正十二烷 (1) + 联苯 (2) + DMSO (3)
0.8841	0.1054	0.0105	0.0325	0.3892	0.5784	3.69	100.55
0.9008	0.0891	0.0101	0.0320	0.3506	0.6174	3.94	110.91
0.9175	0.0727	0.0098	0.0320	0.3079	0.6601	4.23	121.32
0.9340	0.0566	0.0095	0.0328	0.2605	0.7068	4.61	131.26
0.9499	0.0409	0.0092	0.0345	0.2074	0.7581	5.08	139.85
0.9651	0.0259	0.0090	0.0376	0.1475	0.8148	5.69	145.98
0.9790	0.0122	0.0089	0.0430	0.0791	0.8779	6.51	148.38

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