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化学进展 2020, Vol. 32 Issue (9): 1274-1293 DOI: 10.7536/PC200118 前一篇   后一篇

• 综述 •

离子液体固载化及应用研究

康美荣1, 金福祥1, 李臻1, 宋河远1,**(), 陈静1,**()   

  1. 1. 中国科学院兰州化学物理研究所 羰基合成与选择氧化国家重点实验室 兰州 730000
  • 收稿日期:2020-06-30 修回日期:2020-05-15 出版日期:2020-09-24 发布日期:2020-06-30
  • 通讯作者: 宋河远, 陈静
  • 作者简介:
    ** Corresponding author e-mail: (Heyuan Song); (Jing Chen)
  • 基金资助:
    *国家自然科学基金项目(21673259); 江苏省自然科学基金项目(BK20171241)
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Research and Application of Supported Ionic Liquids

Meirong Kang1, Fuxiang Jin1, Zhen Li1, Heyuan Song1,**(), Jing Chen1,**()   

  1. 1. State Key Laboratory of Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China
  • Received:2020-06-30 Revised:2020-05-15 Online:2020-09-24 Published:2020-06-30
  • Contact: Heyuan Song, Jing Chen
  • Supported by:
    The work was supported by the National Natural Science Foundation of China(21673259); the National Science Foundation of Jiangsu Province of China(BK20171241)

离子液体固载化是将离子液体通过物理吸附或化学键合的方法负载到不同的载体上,得到一种新型固体材料,兼具了离子液体与载体的特征,能够显著提升离子液体的利用率,解决离子液体黏度大、传质及分离困难等问题,拓展了离子液体的应用领域。本文根据不同的载体类型,综述了近年来离子液体固载化的研究进展及应用情况,总结了不同载体的优缺点及现阶段研究和应用发展中存在的一些问题,并对固载化离子液体的应用前景进行了展望。

关键词： 离子液体, 固载化, 载体, 多相催化, 复合材料

Supported ionic liquid is a new kind of solid materials prepared by loading ionic liquids onto different carriers through physical adsorption or chemical bonding, which has the characteristics of both ionic liquids and carriers. This process can significantly improve the utilization of ionic liquids, solve the problems of high viscosity, mass transfer and separation of ionic liquids, and expand the application field of ionic liquids. This paper reviews the research progress and application of supported ionic liquids in recent years, summarizes the advantages and disadvantages of different carriers and some problems existing in the current application. Furthermore, the prospect to the development and application of supported ionic liquids is also discussed.

Contents

1 Introduction

2 Immobilization of ionic liquids

2.1 Methods of immobilization

2.2 Immobilization of ionic liquids onto silica gel

2.3 Immobilization of ionic liquids onto polymer

2.4 Immobilization of ionic liquids onto molecular sieve

2.5 Immobilization of ionic liquids onto magnetic materials

2.6 Immobilization of ionic liquids onto metal-organic frameworks

2.7 Immobilization of ionic liquids onto other carriers

3 Conclusion and outlook

Key words: ionic liquid, supported, carrier, heterogeneous catalysis, composite material
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图1 S-[bpim][HCO3]结构式[11]
Fig.1 Structure of S-[bpim][HCO3] [11]
图2 [(CH2)3SO3HVIm]HSO4/硅胶制备示意图[12]
Fig.2 Preparation diagram of [(CH2)3SO3HVIm]HSO4/SiO2[12]
图3 固载型离子液体结构式[16]
Fig.3 Structural of supported ionic liquids[16]
图4 固载型离子液体IL-Ala/SiO2结构式[17]
Fig.4 Structural of immobilized ionic liquid IL-Ala/SiO2[17]
图5 [Pmim]AlCl3/SiO2的制备示意图[19]
Fig.5 Preparation diagram of [Pmim]AlCl3/SiO2[19]
图6 [Silica-Ps-im]HSO4的合成路线[23]
Fig.6 Synthetic route of [Silica-Ps-im]HSO4[23]
图7 KCC-1/IL/PbS结构示意图[24]
Fig.7 Structure of KCC-1/IL/PbS[24]
图8 固载型离子液体合成路线[26]
Fig.8 Synthetic route of immobilized ionic liquids[26]
图9 Si-P8883TFSI/SiO2分子结构式[27]
Fig.9 Structure of Si-P8883TFSI/Si2[27]
图10 固载离子液体结构示意图[29]
Fig.10 Structure of immobilized ionic liquids[29]
图11 MPM-C6V-SO3CF3-IL结构式[33]
Fig.11 Structure of MPM-C6V-SO3CF3-IL[33]
图12 P(4-VPBSA)[HSO4]合成过程[34]
Fig.12 Synthetic route of P(4-VPBSA)[HSO4] [34]
图13 CS-VImPS-PW合成路线[37]
Fig.13 Synthetic route of CS-VImPS-PW[37]
图14 PEK-C-ILs结构式[38]
Fig.14 Structure of PEK-C-ILs[38]
图15 MMFP-IL结构式[39]
Fig.15 Structure of MMFP-IL[39]
图16 PVC固载型离子液体的合成[40]
Fig.16 Synthetic route of PVC immobilized ionic liquid[40]
图17 固载化烷基咪唑离子液体的制备[41]
Fig.17 Preparation of supported alkylimidazolium ionic liquids[41]
图18 PS-CH2-[TSiIm][Cl]结构式[42]
Fig.18 Structure of PS-CH2-[TSiIm][Cl][42]
图19 Resin-X结构式[44]
Fig.19 Structure of Resin-X[44]
图20 [PolyVMPS]PW结构示意图[47]
Fig.20 Structure of [PolyVMPS]PW[47]
图21 Poly(VPyPS)-PW制备过程[51]
Fig.21 Synthetic route of Poly(VPyPS)-PW[51]
图22 PAILs合成路线[54]
Fig.22 Synthetic route of PAILs[54]
图23 离子液体聚合物结构式[55]
Fig.23 Structure of polymeric ionic liquids[55]
图24 离子液体及其聚合物的结构式[57]
Fig.24 Structure of polymerizable ionic liquids and polymeric ionic liquids[57]
图25 Poly(AMPS-BA-co-HEMA)和poly(AMPS-DMAEMA-co-HEMA)结构式[59]
Fig.25 Structure of poly(AMPS-BA-co-HEMA) and poly(AMPS-DMAEMA-co-HEMA) [59]
图26 NO3@PIL和N3@PIL制备过程[60]
Fig.26 Synthetic process of NO3@PIL and N3@PIL[60]
图27 HIILsBr/MCM-41制备过程[64]
Fig.27 Synthetic process of HIILsBr/MCM-41[64]
图28 MCM-22-[CeMIM]Cl/(ZnBr2)2的结构式[65]
Fig.28 Structure of MCM-22-[CeMIM]Cl/(ZnBr2)2[65]
图29 [MCM-41@(CH2)3-1-MIM]Br3的结构式[69]
Fig.29 Structure of [MCM-41@(CH2)3-1-MIM]Br3[69]
图30 SBA-15-pr-ILOH[74]、$[SBA-15-Ps-im]HSO_{4}$[75]和IL-PRO/SBA-15[76]结构式
Fig.30 Structure of SBA-15-Pr-ILOH[74]、$[SBA-15-Ps-im]HSO_{4}$[75] and IL-PRO/SBA-15[76]
图31 SBA-IL-HPW结构示意图[78]
Fig.31 Structure of SBA-IL-HPW[78]
图32 固载离子液体合成过程[83]
Fig.32 Synthetic process of supported ionic liquid[83]
图33 [NaZSM-5IMBs]HSO4结构式[84]
Fig.33 Structure of [NaZSM-5IMBs]HSO4[84]
图34 Fe3O4NPs/IL/Pd(0)结构式[86]
Fig.34 Structure of Fe3O4NPs/IL/Pd(0) [86]
图35 Fe3O4@IL纳米粒子结构式[90]
Fig.35 Structure of Fe3O4@IL[90]
图36 固载离子液体结构式[92]
Fig.36 Structure of the supported ionic liquid[92]
图37 固载离子液体anion-DMIL@SIO2@Fe3O4结构式[95]
Fig.37 Structure of anion-DMIL@SIO2@Fe3O4[95]
图38 Fe3O4@SiO2-IL结构式[97]
Fig.38 Structure of Fe3O4@SiO2-IL[97]
图39 MIL-101(Cr)固载离子液体催化剂结构式[101]
Fig.39 Structure of the MIL-101(Cr) supported ionic liquid[101]
图40 氨基功能化的咪唑类离子液体结构式[106]
Fig.40 Structure of the supported ionic liquid[106]
图41 NpmimBF4-FDU合成路线[113]
Fig.41 Synthetic route of the NpmimBF4-FDU[113]
图42 Na+-MMT-[pmim]HSO4[117]和HT-IL结构式[119]
Fig.42 Structure of Na+-MMT-[pmim]HSO4 and HT-IL[119]
图43 PMO-IL-SH[120]和Ni@IL-PMO结构式[121]
Fig.43 Structure of PMO-IL-SH and Ni@IL-PMO[121]
表1 CO2与环氧丙烷环加成反应合成碳酸丙烯酯
Table 1 Synthesis of propylene carbonate by cycloaddition reaction of CO2 and propylene oxide
Carrier IL Loading means Reaction condition Yield/% Time of reuseb ref
Amount of catalyst T/℃ t/h
SiO2 [(EtO)3SiPMIm]Cl Chemical bonding 8.0 wt% 140 4 84.5 4 18
SiO2 [Pmim]AlCl3 Chemical bonding 6.4 wt% 150 10 98.6 3 19
SiO2 [Bmim]OH Chemical bonding 1.8 mol% 120 10 99.1 4 20
SiO2 [mim]HSO4 Chemical bonding 24.0 wt% 140 5 87.2 6 21
Polystyrene resin HBIMBr Chemical bonding 12.0 wt% 120 3 92.7 5 29
Bifunctional hyperbranched polymers Py-HBPIL(Br)@rGO Chemical bonding 2.4 wt% 120 8 99.0 6 30
P-based polymer nanoparticles NPILs-BPA Chemical bonding 0.5 mol.% 150 4 99.0 7 31
MCM-41 HIILsBr Chemical bonding 6.0 wt.% 115 4 89.9 3 64
MCM-22 [CeMIM]Cl/(ZnBr2)2 Chemical bonding 2.0 mol% 120 2 97.4 3 65
SiO2@Fe3O4 TiCl5-DMIL Chemical bonding 8.6 wt% 100 2 95.0 5 95
MIL-101(SO3H) BMImCl Chemical bonding 0.2 mol% 120 15 -a 5 100
MIL-101(Cr) TSIL Chemical bonding 11.5 wt% 110 6 93.1 5 101
GO [SmIm]I-HA Chemical bonding 4.0 wt% 140 4 95.0 5 115
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摘要

离子液体固载化及应用研究