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Progress in Chemistry 2022, Vol. 34 Issue (11): 2417-2431 DOI: 10.7536/PC220302 Previous Articles   Next Articles

• Review •

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: Revised: Online: Published:
  • 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)
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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
Fig. 1 Number of publications per year retrieved with keywords “Metal-organic frameworks” and “Metal-organic frameworks + adsorption/separation”
Fig. 2 Schematic diagram of MOF-NH2/CHO materials construction and ICPSM
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
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)
Fig. 4 Schematic diagram of MIL-101-NH2 preparation by PSM of MIL-101
Fig. 5 Schematic diagram of MOF-NH2 prepared by loading melamine, ade and EDA on OMSs of MIL-101
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)
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
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)
Fig. 8 Schematic diagram of the synthesis of MIL-68-NH2/TPA-COF hybrid material
Fig. 9 Schematic diagram of (a) ZIF-90 modification by ethanolamine, (b) ZIF-90/COF-42-B synthesis
Fig. 10 Schematic diagram of (a) SIM-1 modified by dodecylamine, (b) UiO-67-CHO modified by amino ligands
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
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
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
Fig. 14 Schematic diagram of ZIF-90 modified by EA and comparison of H2/CO2 selectivity before and after modification
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
Fig. 15 (a) Schematic diagram of ZIF-90 modified by hydroxylamine hydrochloride, (b) adsorption mechanism of U(Ⅵ) on ZIF-90-OM
Fig. 16 Schematic diagram of ZIF-90 modified by POSS-NH2
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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