化工学报 ›› 2022, Vol. 73 ›› Issue (11): 5011-5024.DOI: 10.11949/0438-1157.20221062
收稿日期:
2022-07-28
修回日期:
2022-08-25
出版日期:
2022-11-05
发布日期:
2022-12-06
通讯作者:
张香兰
作者简介:
刘潜(1995—),男,博士研究生,460905289@qq.com
基金资助:
Qian LIU(), Xianglan ZHANG(), Zhiping LI, Zhuoqi LI, Hong YU
Received:
2022-07-28
Revised:
2022-08-25
Online:
2022-11-05
Published:
2022-12-06
Contact:
Xianglan ZHANG
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。
中图分类号:
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.
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]+ |
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]- |
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
IL | Tm/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 | Tm/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
IL | MW/(g·mol-1) | Tb/K | Tc/K | Pc/bar | Vc/(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) | Tb/K | Tc/K | Pc/bar | Vc/(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 |
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 |
Component | NRTL parameters/K | RMSD | ||||||
---|---|---|---|---|---|---|---|---|
i-j | aij | aji | bij | bji | cij | |||
{[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 |
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 | aij | aji | bij | bji | cij | |||
{[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
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/ % | ||||
D∶F | NS | FS | RR | |||||||||
[C2mim][DCA] | 1.63 | 6498.37 | 0.3479 | 8 | 3 | 0.42 | 1215.23 ① | 93.43 | 99.99 | 99.99 | 86.69 | |
0.9981 | 7 | 3 | 0.18 | 769.94 ② | ||||||||
[C2py][DCA] | 1.17 | 4197.59 | 0.4403 | 8 | 3 | 0.45 | 1126.48 ① | 95.84 | 99.99 | 99.99 | 91.15 | |
0.9981 | 6 | 3 | 0.11 | 698.65 ② | ||||||||
[C2py][SCN] | 0.73 | 5999.27 | 0.3522 | 6 | 3 | 0.25 | 1027.74 ① | 96.37 | 99.99 | 99.99 | 92.16 | |
0.9981 | 7 | 3 | 0.17 | 727.01 ② |
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/ % | ||||
D∶F | NS | FS | RR | |||||||||
[C2mim][DCA] | 1.63 | 6498.37 | 0.3479 | 8 | 3 | 0.42 | 1215.23 ① | 93.43 | 99.99 | 99.99 | 86.69 | |
0.9981 | 7 | 3 | 0.18 | 769.94 ② | ||||||||
[C2py][DCA] | 1.17 | 4197.59 | 0.4403 | 8 | 3 | 0.45 | 1126.48 ① | 95.84 | 99.99 | 99.99 | 91.15 | |
0.9981 | 6 | 3 | 0.11 | 698.65 ② | ||||||||
[C2py][SCN] | 0.73 | 5999.27 | 0.3522 | 6 | 3 | 0.25 | 1027.74 ① | 96.37 | 99.99 | 99.99 | 92.16 | |
0.9981 | 7 | 3 | 0.17 | 727.01 ② |
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