油酚分离过程离子液体萃取溶剂的多尺度筛选

doi:10.11949/0438-1157.20221062

摘要/Abstract

摘要：

离子液体作为萃取溶剂已广泛用于油酚混合物的分离，但由于阴阳离子的可调控性，不同离子液体的性质差异较大，快速筛选得到具有应用前景的离子液体至关重要。针对间甲酚-异丙苯分离体系，采用COSMO-RS模型考察不同阴阳离子结构对离子液体分离性能的影响，并通过分子间相互作用能进行分析。在此基础上，提出一种多尺度的离子液体筛选方法，该方法包含无限稀释热力学性质计算、物性估算、相平衡关系计算和过程性能评价。该多尺度方法从分子尺度到单级平衡尺度，再到多级平衡尺度对离子液体进行逐步筛选。结果表明，1-乙基吡啶硫氰酸盐([C₂py][SCN])和1-乙基吡啶双氰胺盐([C₂py][DCA])是最终筛选得到的两种更具有油酚分离应用前景的离子液体。

关键词: 离子液体, COSMO-RS模型, 相平衡, 过程模拟, 间甲酚-异丙苯, 分离

Abstract:

Ionic liquids have been widely used as extractive solvents for the separation of oil-hydroxybenzene mixtures. However, due to the adjustability of cation and anion, the properties of different ionic liquids vary greatly. It is essential to quickly screen ionic liquids with application prospects. For the m-cresol-cumene separation system, the influences of different cation and anion structures on the separation performance of ionic liquids was investigated by COSMO-RS model, and the separation mechanism was analyzed by intermolecular interaction energy. On this basis, a multiscale ionic liquid screening method including the calculation of infinite dilution thermodynamic properties, the estimation of physical properties, the calculation of phase equilibria, and the evaluation of process performance was proposed. The multiscale method gradually screens ionic liquids from molecular scale to single-stage equilibrium scale, and then to multi-stage equilibrium scale. The results show that 1-ethyl-pyridinium thiocyanate ([C₂py][SCN]) and 1-ethyl-pyridinium dicyanamide ([C₂py][DCA]) are two ionic liquids with more application prospects for the separation of oleophenol obtained by final screening.

Key words: ionic liquids, COSMO-RS model, phase equilibria, process simulation, m-cresol-cumene, separation

中图分类号:

TQ 021.8

刘潜, 张香兰, 李志平, 栗卓琦, 喻红. 油酚分离过程离子液体萃取溶剂的多尺度筛选[J]. 化工学报, 2022, 73(11): 5011-5024.

Qian LIU, Xianglan ZHANG, Zhiping LI, Zhuoqi LI, Hong YU. Multiscale screening of ionic liquids as extractive solvents for oil-hydroxybenzene separation[J]. CIESC Journal, 2022, 73(11): 5011-5024.

图/表 19

表1 阳离子的名称和缩写

Table 1 Names and abbreviations of cations

Cations	Names	Abbreviations
[C01]	1-ethyl-3-methyl-imidazolium	[C₂mim]⁺
[C02]	1-propyl-3-methyl-imidazolium	[C₃mim]⁺
[C03]	1-butyl-3-methyl-imidazolium	[C₄mim]⁺
[C04]	1-pentyl-3-methyl-imidazolium	[C₅mim]⁺
[C05]	1-hexyl-3-methyl-imidazolium	[C₆mim]⁺
[C06]	1-ethyl-pyridinium	[C₂py]⁺
[C07]	1-propyl-pyridinium	[C₃py]⁺
[C08]	1-butyl-pyridinium	[C₄py]⁺
[C09]	1-pentyl-pyridinium	[C₅py]⁺
[C10]	1-hexyl-pyridinium	[C₆py]⁺
[C11]	1-ethyl-1-methyl-pyrrolidinium	[C₂mpyr]⁺
[C12]	1-propyl-1-methyl-pyrrolidinium	[C₃mpyr]⁺
[C13]	1-butyl-1-methyl-pyrrolidinium	[C₄mpyr]⁺
[C14]	1-pentyl-1-methyl-pyrrolidinium	[C₅mpyr]⁺
[C15]	1-hexyl-1-methyl-pyrrolidinium	[C₆mpyr]⁺
[C16]	1-ethyl-1-methyl-piperidinium	[C₂mpip]⁺
[C17]	1-propyl-1-methyl-piperidinium	[C₃mpip]⁺
[C18]	1-butyl-1-methyl-piperidinium	[C₄mpip]⁺
[C19]	1-pentyl-1-methyl-piperidinium	[C₅mpip]⁺
[C20]	1-hexyl-1-methyl-piperidinium	[C₆mpip]⁺
[C21]	4-ethyl-4-methyl-morpholinium	[C₂mmor]⁺
[C22]	4-propyl-4-methyl-morpholinium	[C₃mmor]⁺
[C23]	4-butyl-4-methyl-morpholinium	[C₄mmor]⁺
[C24]	4-pentyl-4-methyl-morpholinium	[C₅mmor]⁺
[C25]	4-hexyl-4-methyl-morpholinium	[C₆mmor]⁺
[C26]	ethyl-trimethyl-ammonium	[N₂₁₁₁]⁺
[C27]	propyl-trimethyl-ammonium	[N₃₁₁₁]⁺
[C28]	butyl-trimethyl-ammonium	[N₄₁₁₁]⁺
[C29]	pentyl-trimethyl-ammonium	[N₅₁₁₁]⁺
[C30]	hexyl-trimethyl-ammonium	[N₆₁₁₁]⁺

表2 阴离子的名称和缩写

Table 2 Names and abbreviations of anions

Anions	Names	Abbreviations
[A01]	acetate	[Ac]^-
[A02]	chloride	[Cl]^-
[A03]	bromide	[Br]^-
[A04]	hydrogen sulfate	[HSO₄]^-
[A05]	methyl sulfate	[MeSO₄]^-
[A06]	ethyl sulfate	[EtSO₄]^-
[A07]	dicyanamide	[DCA]^-
[A08]	thiocyanate	[SCN]^-
[A09]	tricyanomethane	[C(CN)₃]^-
[A10]	nitrate	[NO₃]^-
[A11]	tetrafluoroborate	[BF₄]^-
[A12]	hexafluorophosphate	[PF₆]^-

图1 不同阳离子的离子液体在无限稀释下的分离性能

Fig.1 Separation performance of ionic liquids with different cations at infinite dilution

图2 不同烷基含碳数的吡啶离子液体和间甲酚、异丙苯之间的相互作用能

Fig.2 Interaction energy between pyridine ionic liquids with different alkyl carbon numbers and m-cresol, and cumene

图3 不同阴离子的离子液体在无限稀释下的分离性能

Fig.3 Separation performance of ionic liquids with different anions at infinite dilution

图4 不同阴离子的离子液体和间甲酚之间的相互作用能

Fig.4 Interaction energy between ionic liquids with different anions and m-cresol

图5 离子液体多尺度筛选方法流程图

Fig.5 Flowsheet of ionic liquid multiscale screening method

图6 360种离子液体和乙二醇在无限稀释下的热力学性质

Fig.6 Thermodynamic properties of 360 ionic liquids and glycol at infinite dilution

图7 无限稀释热力学性质初步筛选得到的47种离子液体█初步筛选得到的离子液体

Fig.7 47 prescreened ionic liquids by infinite dilution thermodynamic properties

图8 47种初步筛选得到的离子液体的熔点和黏度

Fig.8 Melting point and viscosity of 47 prescreened ionic liquids

表3 由无限稀释热力学性质和物性约束筛选得到的7种离子液体（以乙二醇为基准溶剂）

Table 3 7 ionic liquids screened after the first two steps by infinite dilution thermodynamic properties and physical property constraints （with glycol as the benchmark）

IL	$C m ∞$	$S m ∞$	$W 1 ∞$	$W 2 ∞$	T_m/K	η/cP
[C₂mim][DCA]	19.87	728.37	0.0281	7.66×10^-4	275.58	19.91
[C₃mim][DCA]	19.99	584.74	0.0375	1.32×10^-3	271.82	23.23
[C₂py][DCA]	14.53	825.36	0.0181	5.44×10^-4	263.55	20.47
[C₃py][DCA]	16.46	628.81	0.0284	1.07×10^-3	259.79	23.88
[C₃mim][SCN]	21.66	515.33	0.0429	1.33×10^-3	297.27	52.05
[C₂py][SCN]	21.08	686.24	0.0285	5.57×10^-4	288.99	45.85
[C₃py][SCN]	18.53	567.55	0.0334	1.09×10^-3	285.24	53.51
Glycol	3.35	80.66	0.0508	1.44×10^-3	260.25	17.33

表3 由无限稀释热力学性质和物性约束筛选得到的7种离子液体（以乙二醇为基准溶剂）

Table 3 7 ionic liquids screened after the first two steps by infinite dilution thermodynamic properties and physical property constraints （with glycol as the benchmark）

IL	$C m ∞$	$S m ∞$	$W 1 ∞$	$W 2 ∞$	T_m/K	η/cP
[C₂mim][DCA]	19.87	728.37	0.0281	7.66×10^-4	275.58	19.91
[C₃mim][DCA]	19.99	584.74	0.0375	1.32×10^-3	271.82	23.23
[C₂py][DCA]	14.53	825.36	0.0181	5.44×10^-4	263.55	20.47
[C₃py][DCA]	16.46	628.81	0.0284	1.07×10^-3	259.79	23.88
[C₃mim][SCN]	21.66	515.33	0.0429	1.33×10^-3	297.27	52.05
[C₂py][SCN]	21.08	686.24	0.0285	5.57×10^-4	288.99	45.85
[C₃py][SCN]	18.53	567.55	0.0334	1.09×10^-3	285.24	53.51
Glycol	3.35	80.66	0.0508	1.44×10^-3	260.25	17.33

图9 COSMO-RS计算前两步筛选得到的7种离子液体在不同进料组成下的分离性能

Fig.9 COSMO-RS calculated separation performance at different feed compositions of 7 ionic liquids screened after steps 1 and 2

表4 3种离子液体的摩尔质量、沸点、临界参数、偏心因子和密度

Table 4 Molecular weights， normal boiling points， critical properties， acentric factors， and densities of 3 ionic liquids

IL	MW/(g·mol^-1)	T_b/K	T_c/K	P_c/bar	V_c/(cm³·mol^-1)	ω	ρ/(g·cm^-3)
[C₂mim][DCA]	177.2	670.64	998.48	35.1	562.0	0.3548	1.0750
[C₂py][DCA]	174.2	736.28	1123.34	32.6	571.1	0.2336	1.0243
[C₂py][SCN]	166.2	676.19	926.58	29.0	554.7	0.6922	1.0970

表5 3种离子液体的理想气体热容多项式系数

Table 5 Polynomial coefficients of ideal gas heat capacity of 3 ionic liquids

IL	A₀/(J·mol^-1·K^-1)	A₁/(J·mol^-1·K^-2)	A₂/(J·mol^-1·K^-3)	A₃/(J·mol^-1·K^-4)
[C₂mim][DCA]	13.371	0.76460	-3.728×10^-4	-3.68×10^-8
[C₂py][DCA]	20.691	0.66048	-2.091×10^-4	-4.43×10^-8
[C₂py][SCN]	-22.939	0.56668	-7.310×10^-5	-8.73×10^-8

表6 3个｛离子液体+间甲酚+异丙苯｝三元体系的NRTL参数和均方根偏差

Table 6 NRTL parameters and RMSD values of three ｛ionic liquid + m-cresol + cumene｝ ternary systems

Component	NRTL parameters/K					RMSD
i-j	a_ij	a_ji	b_ij	b_ji	c_ij	RMSD
{[C₂mim][DCA] (1) + m-cresol (2) + cumene (3)}
1-2	3.57	-1.77	684.03	-299.00	0.3	0.0139
1-3	2.48	-3.42	-108.54	2630.06	0.2
2-3	28.46	-7.23	5067.29	2902.47	0.3
{[C₂py][DCA] (1) + m-cresol (2) + cumene (3)}
1-2	0.65	-1.64	1459.52	-351.76	0.3	0.0157
1-3	2.38	-2.47	39.90	2356.43	0.2
2-3	37.04	-6.78	5271.13	2685.83	0.3
{[C₂py][SCN] (1) + m-cresol (2) + cumene (3)}
1-2	4.18	-0.87	974.17	-637.33	0.3	0.0178
1-3	4.46	-1.63	-513.91	2097.21	0.2
2-3	15.66	-5.45	5657.96	2101.41	0.3

图10 离子液体萃取分离间甲酚和异丙苯的过程模拟流程图

Fig.10 Process simulation flowsheet for the separation of m-cresol and cumene using ionic liquids as the extractive solvent

图11 满足间甲酚和异丙苯分离要求萃取塔塔板数和基于质量的溶剂-进料比关系

Fig.11 Mass ratio of solvent-to-feed (S/F) as a function of the number of stages in the extraction column to meet the separation requirements of m-cresol and cumene

图12 满足间甲酚和异丙苯分离要求时萃取塔塔板数和异丙苯回收率的关系

Fig.12 Recovery ratio of cumene as a function of the number of stages in the extraction column when meeting the separation requirements of m-cresol and cumene

表7 3种离子液体萃取分离间甲酚和异丙苯过程模拟的主要结果

Table 7 Main results of process simulation for the separation of m-cresol and cumene using 3 ionic liquids

Extraction column (298.15 K, 1 ×10⁵ Pa, 8 stages)			Distillation column (0.005 ×10⁵ Pa)					Cumene product		m-Cresol product
IL	IL makeup/ (kg·h^-1)	IL in recycle/ (kg·h^-1)	Operating conditions				Heat duty/ kW	Recovery ratio/ %	Mass purity/ %	Recovery ratio/ %	Mass purity/ %
IL	IL makeup/ (kg·h^-1)	IL in recycle/ (kg·h^-1)	D∶F	NS	FS	RR	Heat duty/ kW	Recovery ratio/ %	Mass purity/ %	Recovery ratio/ %	Mass purity/ %
[C₂mim][DCA]	1.63	6498.37	0.3479	8	3	0.42	1215.23 ^①	93.43	99.99	99.99	86.69
[C₂mim][DCA]	1.63	6498.37	0.9981	7	3	0.18	769.94 ^②	93.43	99.99	99.99	86.69
[C₂py][DCA]	1.17	4197.59	0.4403	8	3	0.45	1126.48 ^①	95.84	99.99	99.99	91.15
[C₂py][DCA]	1.17	4197.59	0.9981	6	3	0.11	698.65 ^②	95.84	99.99	99.99	91.15
[C₂py][SCN]	0.73	5999.27	0.3522	6	3	0.25	1027.74 ^①	96.37	99.99	99.99	92.16
[C₂py][SCN]	0.73	5999.27	0.9981	7	3	0.17	727.01 ^②	96.37	99.99	99.99	92.16

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