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化学进展 2022, Vol. 34 Issue (11): 2417-2431 DOI: 10.7536/PC220302 前一篇   后一篇

• 综述 •

氨/醛基金属有机骨架材料合成及其在吸附分离中的应用

闫保有1, 李旭飞2,1, 黄维秋1,*(), 王鑫雅2,1, 张镇1, 朱兵1   

  1. 1 常州大学 油气储运技术省重点实验室 油气回收工程技术研究中心 常州 213164
    2 常州大学 材料科学与工程学院 常州 213164
  • 收稿日期:2022-03-02 修回日期:2022-05-06 出版日期:2022-11-24 发布日期:2022-06-25
  • 通讯作者: 黄维秋
  • 作者简介:

    黄维秋 常州大学石油工程学院教授(二级),博士生导师,江苏省“油气回收基础理论及其应用”科技创新团队带头人,江苏省“333工程”中青年科技领军人才,江苏省有机废气资源化工程技术中心主任,常州大学油气回收工程技术研究中心主任。目前主要研究方向:油气回收基础理论及应用、石油储存工艺和新型纳米功能材料及其在有机废气治理中应用。

  • 基金资助:
    国家自然科学基金项目(52174058); 江苏省重点研发计划(产业前瞻与共性关键技术)(BE2018065); 江苏省研究生科研与实践创新计划项目(KYCX22_3104)
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Synthesis of Metal-Organic Framework-NH2/CHO and Its Application in Adsorption Separation

Baoyou Yan1, Xufei Li2,1, Weiqiu Huang1(), Xinya Wang2,1, Zhen Zhang1, Bing Zhu1   

  1. 1 Jiangsu Provincial Key Laboratory of Oil & Gas Storage and Transportation Technology, Engineering Technology Research Center for Oil Vapor Recovery, Changzhou University,Changzhou 213164, China
    2 College of Materials Science & Engineering, Changzhou University,Changzhou 213164, China
  • Received:2022-03-02 Revised:2022-05-06 Online:2022-11-24 Published:2022-06-25
  • Contact: Weiqiu Huang
  • About author:
    †The authors contribute equally to this review
  • Supported by:
    National Natural Science Foundation of China(52174058); Key Research and Development Program of Jiangsu Province (Industry Foresight and Common Key Technology)(BE2018065); Postgraduate Research & Practice Innovation Program of Jiangsu Province(KYCX22_3104)

吸附分离过程具有高效率、低能耗等特点,广泛用于石油、化工、制药、环保等诸多领域。其中,吸附分离材料的结构特点(如比表面积、孔径、孔体积、表面官能团等)对吸附分离效果起决定性作用。金属有机骨架(MOF)材料具有优异的孔结构特点,同时其表面还具有丰富的官能团(—NH2、—CHO等),易于后修饰功能化并赋予其特定的功能,从而增强MOF材料与吸附质之间的相互作用,实现较高的吸附容量和分离选择性。以此为导向,本文首先概括了氨/醛基MOF材料的合成策略,总结了亚胺共价后修饰MOF (ICPSM-MOF)材料的研究进展,并重点介绍了这类材料在气、液相吸附分离领域的应用,最后分析了当前ICPSM-MOF材料面临的困难与挑战,并对其未来研究方向进行了展望。

关键词： 金属有机骨架材料, 合成, 共价后修饰, 亚胺缩合反应, 吸附分离

Adsorptive separation has been widely used in petroleum, chemical, pharmaceutical, environmental protection and many other fields due to the advantages of high efficiency and low-energy consumption. Therein, the structural characteristics (such as specific surface area, pore size, pore volume, surface functional groups, etc.) of the adsorbent are the key factors that affect the adsorption capacity and separation efficiency. Metal-organic framework (MOF) materials have excellent pore structures and abundant functional groups (—NH2, —CHO, etc.), which can be easily post-modified and functionalized with specific functions, thus enhancing the interaction between MOFs and adsorbates and achieving high adsorption capacity and separation selectivity. In this context, the synthesis strategies of MOF-NH2/CHO materials were firstly outlined, then the research progress of imine covalently post-modified MOF (ICPSM-MOF) materials was summarized, and their applications in gas and liquid adsorption separation were emphasized. In addition, the difficulties and challenges faced by the current ICPSM-MOFs were finally analyzed, and the future research trend of ICPSM-MOFs was also put forward.

Contents

1 Introduction

2 Synthesis strategies of MOF-NH2/CHO materials

2.1 Synthesis strategies of MOF-NH2 materials

2.2 Synthesis strategies of MOF-CHO materials

3 MOF-NH2/CHO materials are modified by imine covalent post synthetic modification

3.1 Imine covalent post synthetic modification of MOF-NH2 materials (MOF—N=C—R)

3.2 Imine covalent post synthetic modification of MOF-CHO materials (MOF—C=N—R)

4 Adsorption and separation application of ICPSM-MOF materials

4.1 Gas phase adsorption separation

4.2 Liquid phase adsorption separation

5 Conclusion and outlook

Key words: metal-organic framework materials, synthesis, covalent post synthetic modification, imine condensation reaction, adsorption separation
()
图1 以“Metal-organic frameworks”和“Metal-organic frameworks+adsorption/separation”为关键词检索到的每年文献出版数
Fig. 1 Number of publications per year retrieved with keywords “Metal-organic frameworks” and “Metal-organic frameworks + adsorption/separation”
图2 MOF-NH2/CHO材料的构筑以及亚胺共价后修饰示意图
Fig. 2 Schematic diagram of MOF-NH2/CHO materials construction and ICPSM
表1 MOF-NH2材料的配体、合成策略及其结构参数
Table 1 Ligands, synthesis strategies and structure parameters of MOF-NH2
MOF-NH2 Ligands Synthesis strategies BET/(m2·g-1) Pore size/
(nm)		 Pore volume/
(cm3·g-1)		 ref
IRMOF-3(Zn) BDC-NH2 DS (A single ligand) 2185~2400 1.3 - 36,37
UiO-66-NH2(Zr) 1321 0.62 0.54 38
CAU-1(Al)-NH2 1300~1530 - 0.54~0.64 39,40
MIL-53(Al)-NH2 950~1309 1.3 1.03~2.61 41,42
MIL-68(In)-NH2 451~655 - - 43,44
MIL-101(Fe)-NH2 2300~3438 2.5 1.64 45,46
MIL-101(Al)-NH2 2100 - 0.77 46
MIL-101(Cr)-NH2 1443 - 0.67 47
MIL-125(Ti)-NH2 1176 2.23 0.46 48
MIL-88(Fe)-NH2 941 8.8 0.6 49
UMCM-1(Zn)-NH2 BDC-NH2、BTB DS (Mixed ligand) 3973 - - 50
DMOF-1(Zn)-NH2 BDC-NH2、DABCO 1510 0.56 - 50
MIL-101-NH2 BDC PSM 1053~2313 - - 64
ZIF-8-NH2 HATZ PSM 183~1848 - 0.17~1.48 67
图3 用于合成MOF-NH2材料的部分配体: (a) 2-氨基对苯二甲酸,(b) 3-氨基-1,2,4-三唑,(c) 5-氨基四氮唑,(d) 5-(5-氨基四氮唑)-1,3-苯二甲酸,(e) 3-氨基-4-(吡啶-4-基)苯甲酸,(f) 5-氨基-1H-咪唑-4-甲腈,(g) 2-氨基-1,3,5-苯三甲酸,(h) 2-氨基苯并咪唑,(i) 腺嘌呤
Fig. 3 Partial ligands for the synthesis of MOF-NH2: (a) 2-aminoterephthalic acid (BDC-NH2), (b) 3-amino-1,2,4-triazole (HATZ), (c) 5-aminotetrazole (5-AT), (d) 5-(5-Amino-1H-tetrazol-1-yl)-1,3-benzenedicarboxylic acid (H2ATBDC), (e) 3-amino-4-(pyridin-4-yl) benzoic acid (BPA-NH2), (f) 5-Amino-1H-imidazole-4-carbonitrile (cyamIm), (g) 2-amino-1,3,5-benzenetricarboxylate (BTC-NH2), (h) 2-aminobenzimidazole (2-amBzIm), (i) adenine (ade)
图4 MIL-101合成后修饰制备MIL-101-NH2示意图
Fig. 4 Schematic diagram of MIL-101-NH2 preparation by PSM of MIL-101
图5 MIL-101的OMSs上负载melamine、ade和EDA制备MOF-NH2材料示意图
Fig. 5 Schematic diagram of MOF-NH2 prepared by loading melamine, ade and EDA on OMSs of MIL-101
图6 用于合成MOF-CHO材料的部分配体:(a) 咪唑-2-甲醛,(b) 4-甲基咪唑-5-甲醛,(c) 2-甲醛联苯-4,4'-二羧酸, (d) 咪唑-4-甲醛
Fig.6 Partial ligands for the synthesis of MOF-CHO: (a) imidazole-2-carboxaldehyde (ICA), (b) 4-methylimidazole-5-carboxaldehyde (aImeIm), (c) 2-formalbiphenyl-4,4'-dicarboxylicacid (H2BPDC-CHO), (d) imidazole-4-carboxaldehyde (AIdIm)
表2 MOF-CHO材料的配体、合成策略及其结构参数
Table 2 Ligands, synthesis strategies and structure parameters of MOF-CHO
MOF-CHO Ligands Synthesis strategies BET/(m2·g-1) Pore size/(nm) Pore volume/(cm3·g-1) ref
ZIF-90(Zn) ICA DS (A single ligand) 189~1937 0.10~0.91 0.35 71,72
ZIF-93(Zn) aImeIm 864 0.464 1.79 73
ZIF-94(Zn)(SIM-1) aImeIm 480 0.229 0.91 73
UiO-67(Zr)-CHO H2BPDC-CHO 1590 0.74 - 74
Ald-ZIF(Zn) 2-mIm、AldIM DS (Mixed ligand) 1130~1396 0.37~0.63 - 75
图7 (a) 水杨醛修饰IRMOF-3,(b) 吡啶-2-甲醛修饰UMCM-1-NH2,(c) 甲醛修饰UiO-66-NH2,(d) 吡啶-2-甲醛修饰MIL-125-NH2(Ti)的示意图
Fig. 7 Schematic diagram of (a) salicylaldehyde modified IRMOF-3, (b) pyridine-2-carbaldehyde modified UMCM-1-NH2, (c) formaldehyde modified UiO-66-NH2, (d) pyridine-2-carbaldehyde modified MIL-125-NH2(Ti)
图8 MIL-68-NH2/TPA-COF杂化材料合成示意图
Fig. 8 Schematic diagram of the synthesis of MIL-68-NH2/TPA-COF hybrid material
图9 (a) 乙醇胺修饰ZIF-90和(b) ZIF-90/COF-42-B合成示意图
Fig. 9 Schematic diagram of (a) ZIF-90 modification by ethanolamine, (b) ZIF-90/COF-42-B synthesis
图10 (a) 十二胺修饰SIM-1和(b) 氨基配体修饰UiO-67-CHO示意图
Fig. 10 Schematic diagram of (a) SIM-1 modified by dodecylamine, (b) UiO-67-CHO modified by amino ligands
图11 (a) PEI修饰的UiO-66-NH2的合成示意图,(b) UiO-66-NH2与PEIC96/UiO对CO2的吸附量和选择性对比
Fig. 11 (a) Schematic diagram of UiO-66-NH2 modified by PEI, (b) comparisons of adsorption capacities and selectivities on UiO-66-NH2 and PEIC96/UiO for CO2
图12 (a) 2,3,4,5,6,-五氟苄胺修饰ZIF-90示意图,(b) ZIF-90与S-ZIF-90对CO2、CH4和N2的吸附量对比
Fig. 12 (a) Schematic diagram of ZIF-90 modified by 2,3,4,5,6-pentafluorobenzonitrile, (b) comparisons of adsorption capacities on ZIF-90 and S-ZIF-90 for CO2, CH4 and N2
图13 (a) ICA修饰UiO-66-NH2示意图,(b) UiO-66-NH2与UiO-66-NH2/ICA对CO2和CH4的吸附量对比
Fig. 13 (a) Schematic diagram of UiO-66-NH2 modified by ICA, (b) comparisons of adsorption capacities on UiO-66-NH2 and UiO-66-NH2/ICA for CO2 and CH4
图14 乙醇胺修饰ZIF-90示意图以及修饰前后H2/CO2选择性对比
Fig. 14 Schematic diagram of ZIF-90 modified by EA and comparison of H2/CO2 selectivity before and after modification
表3 典型的ICPSM-MOF材料的反应条件、应用领域及作用机理
Table 3 Reaction conditions, application areas and mechanism of action of typical ICPSM-MOF
ICPSM-MOF Reaction conditions Application areas Mechanism ref
ZIF-90/TETA 25℃, 12 h CO2 capture Pore filling adsorption、Thermodynamic equilibrium (-NH2) 100
PEIC/UiO 25℃, 12 h CO2 capture Pore filling adsorption、Thermodynamic equilibrium (-NH2) 93
S-ZIF-90 70℃, 24 h CO2 capture Pore filling adsorption、Thermodynamic equilibrium (F) 95
ZIF-90/GO/EDA 100℃, 18 h/50℃, 4 h CO2 capture Pore filling adsorption、Thermodynamic equilibrium (-NH2) 97
UiO-66-NH2/ICA 80℃, 12 h CO2/CH4 Thermodynamic equilibrium (N)、Size sieving effect 96
UIO-66-NH2/TpPa-1 80℃, 1 h CO2/CH4 Size sieving effect 87
ZIF-90/EA 60℃, 10 h/24 h H2/CO2 Size sieving effect 101
ZIF-90/APTES 110℃, 0.5 h H2/CO2、CO2/CH4 Size sieving effect 100
UiO-66-NH2/sal 40℃, 2 h H2/CO2、H2/CH4 Size sieving effect 38
图15 (a) 盐酸羟胺修饰ZIF-90示意图,(b) U(Ⅵ)在ZIF-90-OM上吸附机理
Fig. 15 (a) Schematic diagram of ZIF-90 modified by hydroxylamine hydrochloride, (b) adsorption mechanism of U(Ⅵ) on ZIF-90-OM
图16 POSS-NH2修饰ZIF-90示意图
Fig. 16 Schematic diagram of ZIF-90 modified by POSS-NH2
表4 典型的ICPSM-MOF材料的反应条件、应用领域及作用机理
Table 4 Reaction conditions, application areas and mechanism of action of typical ICPSM-MOF
ICPSM-MOF Reaction conditions Application areas Mechanism ref
UiO-66-PTC 80℃, 36 h Pb(Ⅱ) Chelation of S、N with Pb(Ⅱ) 107
ZIF-90-OM 60℃, 24 h U(Ⅳ) Interaction between oxygen in -CHO、Zn-OH and N-OH and U(Ⅳ) 108
ZIF-90-ABOA 100℃, 24 h U(Ⅳ) Chelation of amine oxime group with U(Ⅳ) 109
ZIF-90-SH 60℃, 24 h Hg(Ⅱ) Chelation of S、N with Hg(Ⅱ) 106
TSC-ZIF 100℃, 24 h Hg(Ⅱ) Chelation of S、N with Hg(Ⅱ) 75
MIL-101(Cr)-N-2-pyc 40℃, 12 h ANI、FUR、BPA Hydrogen bonding, π-π bonding interactions and electrostatic gravity 47
ZIF-POSS 80℃, 24 h Organic solvents (n-hexane,
toluene, chloroform, sec-
butanol)/water		 Hydrophobic, lipophilic 114
M5C 180℃, 12 h AO、RB Electrostatic interactions, van der Waals forces, hydrogen bonding, the Lewis acid-base and π-π bond interactions 113
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