多孔离子液体的构筑及应用

doi:10.6023/A22010053

化学学报 ›› 2022, Vol. 80 ›› Issue (6): 848-860.DOI: 10.6023/A22010053 上一篇

综述

多孔离子液体的构筑及应用

李晓倩, 张靖, 苏芳芳, 王德超, 姚东东^*(), 郑亚萍^*()

西北工业大学化学与化工学院西安 710129

投稿日期:2022-01-27 发布日期:2022-07-07
通讯作者: 姚东东, 郑亚萍

作者简介:

李晓倩, 西北工业大学化学与化工学院材料学专业在读博士研究生, 研究方向为多孔离子液体的构筑及其气体吸附分离与催化转化应用.

张靖, 西北工业大学化学与化工学院在读硕士研究生, 研究方向为先进多孔液体的合成及其催化应用.

苏芳芳, 西北工业大学化学与化工学院化学专业在读博士研究生, 研究方向为先进多孔液体及无溶剂纳米流体的合成及其在光热转化领域的应用.

王德超, 西北工业大学化学与化工学院化学专业博士研究生在读, 研究方向为新型分离复合材料(无溶剂纳米流体与多孔液体及其膜材料)、碳捕集和吸附工艺、化工过程计算机模拟.

姚东东, 西北工业大学化学与化工学院副教授, 2013年获得中国科学院化学所高分子化学与物理专业博士学位, 神奈川大学博士后, 长期从事杂化多孔液体和聚合物纳米复合材料的制备及其应用研究.

郑亚萍, 西北工业大学化学与化工学院教授, 博士生导师, 美国康奈尔大学访问学者, 研究方向为多孔液体、无溶剂纳米流体的构筑及其在CO₂捕集、聚合物基复合材料纳米填料、膜分离、催化转化、光热转换等领域的应用. 现已主持完成国家自然科学基金、陕西省自然科学基金、航空科学基金等国家级、省部级纵向课题和横向课题20余项. 在AFM、ACS Nano、Angew. Chem.、Small、JMCA、CEJ、Nano-Micro Lett等权威期刊发表论文180余篇; 授权国家发明专利12件; 参编高等学校教材4部.

基金资助:
西北工业大学博士论文创新基金(CX2021110); 国家自然科学基金(21905228); 航空科学基金(2018ZF53065)

Construction and Application of Porous Ionic Liquids

Xiaoqian Li, Jing Zhang, Fangfang Su, Dechao Wang, Dongdong Yao(), Yaping Zheng()

School of Chemistry and Chemical Engineering, Northwestern Polytechnical University, Xi′an 710129, China

Received:2022-01-27 Published:2022-07-07
Contact: Dongdong Yao, Yaping Zheng
Supported by:
Innovation Foundation for Doctor Dissertation of NWPU(CX2021110); National Natural Science Foundation of China(21905228); Aeronautical Science Foundation of China(2018ZF53065)

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摘要/Abstract

多孔液体(Porous Liquids, PLs)是一类结合了多孔固体永久性孔隙与液态流动性优势的新材料. 自2007年, PLs的概念被首次提出以来, 其在合成策略与应用领域方面均取得了较大的突破. 然而, 传统的PLs因高黏度、高密度、高熔点与高原材料成本等缺陷极大程度制约了其在流动工业系统中的大规模应用. 因此, 迫切需要寻求理想的位阻溶剂用于制备先进的多孔液体. 离子液体(Ionic Liquids, ILs)因独特的可调节物理特性、非挥发性、高稳定性、易获得、经济性高、低再生能耗等特性, 使其成为构筑PLs中最具有应用前景的理想溶剂之一. 在过去的5年间, 基于多种ILs与先进多孔固体(如有机笼、金属有机框架、中空碳、沸石、多孔聚合物等)制备的多孔离子液体(Porous Ionic Liquids, PILs)被陆续报道. PILs独特的永久性孔隙、无溶剂挥发、再生能力强、黏度可调、低熔点、高稳定性等特性加快了其在气体吸附、分离、催化、萃取、分子分离等领域的快速发展. 本综述围绕PILs的构筑策略、特性、应用领域等阐述了其研究进展. 最后, 对PILs在制备中存在的挑战与未来的研究方向进行了归纳与展望.

关键词: 多孔离子液体, 多孔液体, 离子液体, 气体吸附, 分离, 催化

The concept of porous liquids (PLs) was initially proposed and divided into three types in 2007 by James, which combine the merits of porous solids and flowing liquids. Recently, PLs have made great progress in preparations and applications. However, challenges for PLs still present to be addressed including their high density, viscosity melting temperatures, and materials cost, which severely limit their large-scale applications in flowing systems. Therefore, it is urgent to look for ideal sterically hindered solutions to construct PLs materials. Notably, the unique properties of ionic liquids (ILs), such as the tunable physicochemical properties for task-specific applications, economic, low regeneration energy requirements, enable them as promising candidates for constructing novel porous ionic liquids (PILs). Over the past five years, PILs based on ILs and existing advanced porous solids, such as porous organic cages (POCs), metal-organic frameworks (MOFs), porous carbons, zeolites, porous polymers, etc., have successively witnessed the achievement in synthesis strategies and applications. Notably, PILs exhibit remarkable properties including permanent porosity, negligible volatility, high thermal/chemical stability, non-corrosivity, adjustable melting temperature, viscosity, high gas solubilities, and fast gas diffusion, which have accelerated their applications in gas adsorption/separation, chiral separation, catalytic conversion, extraction, molecular separations, and other fields. In this review, we summarized recent research progress on the synthesis strategies, properties, and applications of PILs. In the end, challenges and future developments for PILs are summarized and prospected.

Key words: porous ionic liquids, porous liquids, ionic liquids, gas capture, separation, catalysis

引用此文

李晓倩, 张靖, 苏芳芳, 王德超, 姚东东, 郑亚萍. 多孔离子液体的构筑及应用[J]. 化学学报, 2022, 80(6): 848-860.

Xiaoqian Li, Jing Zhang, Fangfang Su, Dechao Wang, Dongdong Yao, Yaping Zheng. Construction and Application of Porous Ionic Liquids[J]. Acta Chimica Sinica, 2022, 80(6): 848-860.

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图/表 24

图1. 传统液体与三种类型多孔液体的对比[6]

Figure 1. Comparison of conventional liquids and three types of porous liquids[6]

图2. (a) 两步法制备HS-liquid策略; (b) HS-liquid支撑膜的气体分离示意图; (c) PEGS (i), HS-liquid (ii), SS-liquid (iii), CS-liquid (iv)与CS/Ni-liquid (v)的气体渗透量[23]

Figure 2. (a) Two-step synthetic strategy for porous liquid fabrication, HS=hollow silica, OS=organosilane; (b) schematic representation of gas separation in membrane supported HS-liquid; (c) gas permeability obtained on (i) PEGS, (ii) HS-liquid, (iii) SS-liquid, (iv) CS-liquid, and (v) CS/Ni-liquid[23]

图3. (a) HCS-liquid多孔液体的制备方法; (b) HCS-liquid的模量-温度曲线与照片; (c) HCS-liquid, PEGS, SCS-liquid和PILs-PEGS的CO2吸附-脱附曲线(25 ℃, 1 MPa)[38]

Figure 3. (a) Synthesis strategy for HCS-liquid; (b) modulus- temperature curve and photograph (inset) of the HCS-liquid; (c) CO2 adsorption-desorption isotherms of HCS-liquid, PEGS, SCS-liquid and PILs-PEGS composite collected below 1 MPa at 25 ℃, respectively[38]

图4. HCS与HCS-PILs-PEGS的合成策略[39]

Figure 4. Schematic illustration of the synthesis of HCS and HCS-PILs-PEGS[39]

图5. (a)阴离子共价笼(ACC)合成策略与结构式; (b) 15-冠醚-5和二环己基-18-冠醚-6的化学结构; (c)冠醚-ACC多孔液体的合成路线[41]

Figure 5. (a) Synthetic procedure and chemical structure of anionic covalent cage (ACC); (b) chemical structures of 15-crown-5 and dicyclohexano-18-crown-6; (c) representation of synthetic procedures for the crown ether-ACC porous liquids[41]

图6. (a)笼1~3的制备; (b)笼2结合了一系列不同的丙醇和丁醇异构体, 主客腔的形状匹配越好, 结合越牢固[42]

Figure 6. (a) Preparation of cages 1~3; (b) cage 2 bound a range of different propanol and butanol isomers; a better shape match between guest and host cavity led to a stronger binding [42]

图7. (a)离子交换法合成多孔液体Im-UiO-PL的示意图; (b) Deim-UiO-66的孔隙分布; (c)不同吸附剂的CO2催化转化对比(黑色代表CO2的催化转化量, 红色代表吸附剂的吸收量)[43]

Figure 7. (a) Schematic synthesis of porous MOF liquid Im-UiO-PL via an ionic-exchange method; (b) the pore space in Deim-UiO-66; (c) the experimental results of catalytic conversion of CO2 with different adsorbents (black bars represent the transformed amount of CO2, red bars represent the adsorbed amount of adsorbents)[43]

Type	Sample name	Viscosity/ (Pa•s at 25 ℃)	T_m/℃	CO₂ adsorption	Ref.
PLs	PS-OS@SiNRs	Like-gel	15, 20	3.3, 4.8% (w) (0 ℃)	^[15]
	HS@OS@PEGs	6.8 at 40 ℃	20	CO₂/N₂ separation	^[23]
	HS@OS@PEGs	4.2 at 50 ℃	20	CO₂/N₂ separation
	UiO-66-liquids	14.000	–4.83	0.25 mmol•g^-1 (1 MPa 25 ℃)	^[44]
	UiO-66-liquid-M2070	4.6	–6.1	2.68 mmol•g^-1 (1 MPa 25 ℃)	^[45]
PILs	HCS-liquids	High viscosity	12	55.9% (w) (0.1 MPa)	^[38]
	100-P[VHIm]-PEGS	8.9 at 50 ℃	9.8	1.8 mmol•g^-1(0.3 MPa)	^[39]
	18-C-6-PL	—	50	0.43 mmol•g^-1(1 MPa)	^[41]

表1. Ⅰ型多孔离子液体与现有传统Ⅰ型多孔液体的黏度、熔点与CO2吸附量的对比

Table 1. Comparison of the viscosity, melting temperature, and CO2 adsorption capacity of type Ⅰ porous ionic liquids to coexisting traditional type Ⅰ porous liquids

图8. 冠醚笼多孔液体的合成[46]

Figure 8. Preparation of the crown ether cage porous liquids[46]

图9. (a)高度溶解性混乱笼33:133; (b) 14种用于提高笼溶解度和尺寸排除的有机溶剂; (c)尺寸排除-溶剂被添加到已吸附氙的多孔液体中(20% w/V 33:133溶于PCP); (d)用氯仿(1.0摩尔当量相对于笼)从纯溶剂(1 mL, 虚线)和多孔液体(20% w/V, 200 mg的33:133溶于1 mL的溶剂中)测量的平均氙吸收值; (e)不同黏度下, 33:133HAP与33:133TBA的氙吸附量曲线[47]

Figure 9. (a) Synthesis of a highly-soluble scrambled 33:133 cage mixture; (b) the 14 bulky solvents screened for both cage solubility and size-exclusion from the cage cavity; (c) scheme illustrating the size-exclusion screen for potential porous liquid solvents-each candidate solvent was added to a known xenon-loaded porous liquid (33:133 20% in PCP); (d) average xenon uptake measured by displacement from the neat solvents (1 mL, dashed lines) and from each porous liquid (200 mg 33:133 with 1 mL PCP, 20% w/V) using chloroform (1.0 molar equivalent relative to cage)-average of 3 measurements; (e) the xenon adsorption capacity of 33:133HAP and 33:133TBA at different viscosities[47]

图10. (a) MOP-18多孔液体的制备示意图; (b) 15-冠醚-5与MOP-18间的平均力势(PMF)及15-冠醚-5接近MOP-18窗口的路径; (c)单个MOP-18周围15-冠醚-5沿X轴和Y轴的密度分布, 高密度和低密度分别用黄色和蓝色显示; CO2透过PLs-5% (w)/氧化石墨烯膜(d)和15冠醚-5/氧化石墨烯膜(e)的示意图[48]

Figure 10. (a) Schematic of preparation of MOP-18 based porous liquids; (b) the potential of mean force (PMF) between 15-crown-5 and MOP-18, and insert shows the path that 15-crown-5 approaches square windows of MOP-18; (c) the distribution density of 15-crown-5 around a single MOP-18 along X-axis and Y-axis; the high and low values are shown in yellow and blue respectively. Illustrated channels of CO2 passing through PLs-5% (w)/GO membrane (d) and 15-crown-5/GO membrane (e)[48]

图11. (a)多孔液体15-C-5-PL的照片; (b)在25 ℃下, 15-C-5-PL的正电子寿命轨迹图谱[41]

Figure 11. (a) Photographs and (b) the positron lifetime traces of 15-C-5-PL collected at 25 ℃ [41]

图12. ZIF-8多孔液体形成示意图[49]

Figure 12. Schematic illustration of the formation of ZIF-8 porous liquid[49]

图13. (a)多孔离子液体的制备示意图; (b)在模拟快照中多孔液体中的自由体积(绿色区域), 白色区代表孔隙空间, ZIF-8和HKUST-1在多孔液体中存在孔, Mg-MOF-74中孔隙被填充[50]

Figure 13. (a) Preparation and characterization of the porous liquid; (b) identification of free volume (green regions) in simulation snapshots determined, the white regions inside the MOF are also void space, ZIF-8 and HKUST-1 with pores in PILs, then pores in Mg-MOF-74 were filled[50]

图14. H-ZSM-5-liquid/[P66614][Br]的制备策略[51]

Figure 14. Depiction of the preparation strategy for the porous liquid zeolites (H-ZSM-5-liquid/[P66614][Br])[51]

图15. 基于相似的相容性原理制备多孔液体UIO-66-liquid/ [M2070][IPA]的示意图[53]

Figure 15. Fabrication based on a similar compatibility principle of the MOF-based porous liquid UIO-66-liquid/[M2070][IPA] [53]

图16. 低黏度ZIF-67-PILs的合成策略示意图[54]

Figure 16. Illustration of synthesis strategy for ZIF-67-PILs with low viscosity[54]

图17. ZIF-8-PILs(ZIF-8/[Bpy][NTf2])的合成示意图[55]

Figure 17. The synthesis of ZIF-8-PILs (ZIF-8/[Bpy][NTf2])[55]

图18. (a)聚离子液体[M2070][PSS]的合成; (b) HCNS-liquid的制备策略[56]

Figure 18. (a) Synthesis of the poly(ionic liquid)s (PILs, [M2070][PSS]); (b) the depiction of the preparation strategy for the HCNS-liquid[56]

图19. 醋酸四烷基膦离子液体吸收CO2的机理[57]

Figure 19. Mechanism of CO2 absorption by a tetraalkylphosphonium acetate ionic liquid[57]

图20. COFs基多孔离子液体制备示意图[59]

Figure 20. Illustration of synthesis strategy for COFs porous ionic liquids[59]

图21. HPMo@ZIF-8-PIL的制备示意图[60]

Figure 21. Schematic illustration of the formation of HPMo@ZIF-8-PIL[60]

图22. 双功能沸石多孔液体(MCM-22-PL)的deacetalization- Knoevenagel反应路线[62]

Figure 22. Reaction pathway of bifunctional zeolite porous liquid (MCM-22-PL) system of the cascade deacetalization-Knoevenagel condensation[62]

Type	Sample name	Viscosity/ (Pa•s at 25 ℃)	T_m/℃	CO₂ adsorption (25 ℃)	Ref.
PLs	PL1	5.1		30.8 cm³•g^-1 (1 MPa)	^[28]
	PL4	6.0	–35	29.0 cm³•g^-1 (1 MPa)
	PL5	11.0		12.4 cm³•g^-1 (1 MPa)
	ZIF-8-g-BPEI -10	1.7	–70.1	0.98 mL•g^-1 (1 MPa)	^[27]
	ZIF-8-g-BPEI -20	7.1	–60.1	3.49 mL•g^-1 (1 MPa)	^[27]
	ZIF-8/[P66614][NTf₂]	—	—	2.12% (w) (0.5 MPa)	^[33]
PILs	ZIF-8/[DBU-PEG][NTf₂]	—	—	1.56 mmol•g^-1 (1 MPa)	^[49]
	ZIF-8/[Bpy][NTf₂]	—	—	2.5% (w)	^[50]
	H-ZSM-5-liquid	9.550	–13.5	2% (w) (1 MPa)	^[51]
	UiO-66-liquid	—	8	7.32% (w) (1 MPa)	^[52]
	ZIF-67-PLs-2	0.54		5.77 mmol•g^-1 (0.1 MPa)	^[54]
	ZIF-67-PLs-5	0.93	–67	7.12 mmol•g^-1 (0.1 MPa)
	ZIF-67-PLs-10	1.89	—	9.54 mmol•g^-1 (0.1 MPa)

表2. Ⅲ型多孔离子液体与现有传统Ⅲ型多孔液体的黏度、熔点与CO2吸附量的对比

Table 2. Comparison of the viscosity, melting temperature, and CO2 adsorption capacity of type Ⅲ porous ionic liquids to coexisting traditional type Ⅲ porous liquids

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	(刘文巧, 李臻, 夏春谷, 化学进展, 2018, 30, 1143.) doi: 10.7536/PC180106

多孔离子液体的构筑及应用

Construction and Application of Porous Ionic Liquids

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