CN110330515A - A kind of nitrogen oxygen mixed ligand Zn complex and preparation method thereof - Google Patents
A kind of nitrogen oxygen mixed ligand Zn complex and preparation method thereof Download PDFInfo
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- B01D53/02—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography
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- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/223—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material containing metals, e.g. organo-metallic compounds, coordination complexes
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Abstract
The invention discloses a kind of nitrogen oxygen mixed ligand Zn complexes and preparation method thereof, belong to polymer self assembles technical field.Its chemical formula is [Zn2(L1)2L2], wherein L1It is 1,3,5- tri- (2- methyl-1 H- imidazoles) benzene ligands, L2For 1,4- phthalic acid or derivatives thereof.Preparation process of the present invention is simple, at low cost, mild condition, and it has good absorption property to carbon dioxide, and selectivity is good, can realize the separation of carbon dioxide Yu nitrogen and methane well, have good application prospect in energy gas purification art.
Description
Technical field
The invention belongs to polymer chemistry, polymer self assembles and supramolecular materials technical fields, and in particular to a kind of nitrogen
Oxygen mixed ligand Zn complex and preparation method thereof.
Background technique
Metal-organic framework materials containing two kinds of coordination atoms of nitrogen and oxygen are mixed by metal ion and oxazolyl and carboxylic acid
Close the crystal structure that is formed by connecting of ligand, there is special cellular structure, pore size and duct environment can be adjusted and
Modification, is a kind of ideal gas absorption separation material.Nitrogen oxygen mixed ligand metal-organic framework materials catch carbon dioxide
It catches and separates and show great potentiality [Chemsuschem, 2014,7,3202], can be used for high-purity gas field of purification, mainly
Adsorption carbon dioxide impurities gas.Studies have shown that can be constructed by using different metal or ligand various novel
The metal-organic framework materials of crystal structure, and design and synthesis are oriented according to its application, this makes it in gas absorption point
There is great application prospect from aspect.
Summary of the invention
Limitation based on existing single ligand to metal-organic framework materials in terms of structure control, and inhaled in carbon dioxide
Fufen is not ideal enough from aspect performance, and it is an object of the invention to design and synthesize the nitrogen oxygen mixing with novel crystal structure to match
Body metal-organic framework materials.
In order to achieve the above objectives, the technical solution adopted by the present invention are as follows:
A kind of nitrogen oxygen mixed ligand Zn complex, chemical formula are [Zn2(L1)2L2], wherein L1For (the 2- methyl-of 1,3,5- tri-
1H- imidazoles) benzene ligand) (I), L2For Isosorbide-5-Nitrae-phthalic acid or its derivative for having substituent group, L1Structural formula is as follows:
The nitrogen oxygen mixed ligand Zn complex crystal belongs to monoclinic system, I 2/a space group, and with 3,4-c connection
Network forms crystal structure, and point symbol is { 3.8^2 } 3 { 8^3.9^3 }, and cell parameter is a=19.356 (3), b=11.6626
(15),α=90, β=102.233 (2), γ=90 °,
The preparation method of the nitrogen oxygen mixed ligand Zn complex includes the following steps:
(1) L is prepared1Ligand: 1,3,5- tribromo-benzene, 2-methylimidazole, potassium carbonate and copper sulphate are mixed and are ground uniformly,
It is fitted into polytetrafluoro liner reactor, baking oven heating reaction is put into after nitrogen purging；After reaction, it is down to room temperature, is washed with water
Retain filter residue after washing suction filtration, extracted, filtered, revolving obtains ligand L1；
(2) L for preparing step (1)1Ligand, L2N,N-dimethylformamide and water is added in ligand and zinc nitrate hexahydrate
In the mixed solvent, is added dropwise concentrated nitric acid, and stirring to solution is clarified；
(3) clear solution prepared by step (2) is moved in vial, is covered, be placed in baking oven and heat reaction, reaction
After, it is filtered, is washed, it is dry, obtain nitrogen oxygen mixed ligand Zn complex.
Water used is deionized water in step (1) and step (2).
L in step (2)1Ligand, L2Ligand and zinc nitrate hexahydrate molar ratio are 2:2:5.Ligand L1Concentration be 6~
7mmol/L。
Step (2) L2Ligand includes 1,4- phthalic acid, 2- amino -1,4- phthalic acid, 2,5- dihydroxy -1,4- benzene two
Formic acid and the fluoro- 1,4- phthalic acid of 2,3,5,6- tetra-.
The dropwise addition volume Yu mixed solvent volume ratio of concentrated nitric acid are 1:200 in step (2).
As a preferred embodiment, 180 DEG C of oven temperature in step (1), the reaction time is for 24 hours；
As a preferred embodiment, n,N-Dimethylformamide and water volume ratio are 3:1 in step (2)；
As a preferred embodiment, the concentration of concentrated nitric acid is 15mol/L in step (2)；
As a preferred embodiment, 80 DEG C of oven temperature in step (3), the reaction time is for 24 hours.
The invention has the following advantages:
The present invention has synthesized a kind of quasi- three-dimension layer column heap of novel zinc-base by ternary imidazole ligands and dicarboxylic acids ligand
Folded crystal structure, synthetic method is simple, and yield is up to 80% or more, and the complex has good adsorptivity to carbon dioxide
Can, selectivity is good, can realize the separation of carbon dioxide Yu nitrogen and methane well, have well in energy gas purification art
Application prospect.
Detailed description of the invention
Fig. 1 is the asymmetric cell of complex embodiment 1 of the present invention.
Fig. 2 is the ligand L of complex embodiment 1 of the present invention1Connection figure.
Fig. 3 is the ligand L of ligand object embodiment 1 of the present invention2Connection figure.
Fig. 4 is the metal connection figure of ligand object embodiment 1 of the present invention.
Fig. 5 is one-dimensional channels figure of the complex embodiment 1 of the present invention in a axis direction.
Fig. 6 is the x-ray diffractogram of powder of complex embodiment 1 of the present invention, in figure, the powder X-ray of 1- complex of the present invention
X ray diffration pattern x, 2- simulation drawing.
Fig. 7 is the x-ray diffractogram of powder of complex embodiment 2 of the present invention, in figure, the powder X-ray of 1- complex of the present invention
X ray diffration pattern x, 2- simulation drawing.
Fig. 8 is the x-ray diffractogram of powder of complex embodiment 3 of the present invention, in figure, the powder X-ray of 1- complex of the present invention
X ray diffration pattern x, 2- simulation drawing.
Fig. 9 is the x-ray diffractogram of powder of complex embodiment 4 of the present invention, in figure, the powder X-ray of 1- complex of the present invention
X ray diffration pattern x, 2- simulation drawing.
Figure 10 is carbon dioxide, methane and the nitrogen etc. of complex embodiment 1 of the present invention and embodiment 2 at a temperature of 298K
Warm adsorption curve comparison diagram.
Figure 11 is the carbon dioxide/methane and two of complex embodiment 1 of the present invention and embodiment 2 in 298K temperature Imitating
Carbonoxide/nitrogen separation index contrast figure.
Figure 12 is the quasi- three-dimension layer and column stacked structure schematic diagram of complex of the present invention.
Specific embodiment
Explanation that the present invention will be further explained combined with specific embodiments below, but specific embodiment is not to the present invention
It is limited in any way.Unless stated otherwise, reagent, method involved in embodiment are reagent and method commonly used in the art.
Embodiment 1
(1) ligand L1Preparation
1,3,5- tribromo-benzene (6.3g, 20mmol), 2-methylimidazole (9.85g, 120mmol), potassium carbonate (11.05g,
80mmol) uniformly, copper sulphate (125mg, 0.5mmol) is added in said mixture in grinding, and it is uniform to continue grinding.It will be above-mentioned solid
Body is fitted into polytetrafluoro liner reactor, and nitrogen purging is packed into stainless steel cauldron after ten minutes, is fastened, is put into 180 DEG C of baking oven
Reaction 24 hours.After reaction, it is down to room temperature, with water filtering and washing (3*100mL), removes inorganic salts and unreacted 2- first
Base imidazoles；By above-mentioned filter residue, methylene chloride extracts (3*250mL methylene chloride), and magnesium sulfate (standing 3-4 hours) is added to dry and remove
Remaining moisture is extracted, is filtered, revolving removes methylene chloride, obtains product, yield 78%.
(2) preparation of nitrogen oxygen mixed ligand Zn complex
L prepared by step (1)1Ligand (3.8mg, 0.012mmol), L2Ligand 1,4- phthalic acid (2mg,
0.012mmol) and zinc nitrate hexahydrate (8mg, 0.03mmol), n,N-Dimethylformamide (1.5mL) and water (0.5mL) is added
10 μ L of concentrated nitric acid (concentration of concentrated nitric acid is 15mol/L) is added dropwise in the mixed solvent, and stirring to solution is clarified；Clear solution is moved
It to 10mL vial, covers, is placed in baking oven and reacts 24 hours for 80 DEG C, after reaction, by light yellow bulk crystal mistake
Filter, n,N-Dimethylformamide washing is dry, obtains nitrogen oxygen mixed ligand Zn complex, yield 83%.
Embodiment 2
(1) ligand L1Preparation
With embodiment 1.
(2) preparation of nitrogen oxygen mixed ligand Zn complex
With embodiment 1, L2Coordination is 2- amino-Isosorbide-5-Nitrae-phthalic acid (2.5mg, 0.012mmol), and crystal color is Huang
Color, yield 81%.
Embodiment 3
(1) ligand L1Preparation
With embodiment 1.
(2) preparation of nitrogen oxygen mixed ligand Zn complex
With embodiment 1, L2Coordination is 2,5- dihydroxy-Isosorbide-5-Nitrae-phthalic acid (2.75mg, 0.012mmol), crystal color
For buff, yield 85%.
Embodiment 4
(1) ligand L1Preparation
With embodiment 1.
(2) preparation of nitrogen oxygen mixed ligand Zn complex
With embodiment 1, L2Coordination is 2,3,5,6- tetra- fluoro- Isosorbide-5-Nitrae-phthalic acids (3.0mg, 0.012mmol), crystal color
To be light yellow, yield 90%.
Embodiment 2 replaces L2Ligand is 2- amino-Isosorbide-5-Nitrae-phthalic acid, and crystal color is by L2Ligand influences, and becomes yellow
Color.
Embodiment 3 replaces L2Ligand is 2,5- dihydroxy-Isosorbide-5-Nitrae-phthalic acid, and crystal color is by L2Ligand influences, and becomes
Buff.
Embodiment 4 replaces L2Ligand is 2,3,5,6- tetra- fluoro- Isosorbide-5-Nitrae-phthalic acids, and crystal color is by L2Ligand influences, and becomes
It is light yellow.
Embodiment 1 and 2 gained crystal of embodiment are shown in attached in the adsorption isothermal curve of 298K carbon dioxide, methane and nitrogen
Figure 10, it can be seen that 1 gained crystal of embodiment is under the conditions of 298K and 1bar, carbon dioxide, methane and nitrogen adsorption capacity difference
For 2.60,0.44 and 0.13mmol/g.By to the similar structure (zinc/triazole/1,4- phthalic acid series layer column in document
Structure) comparison discovery, complex of the present invention is with superior carbon dioxide adsorption performance (see the table below).
Compared to 1 gained crystal of embodiment under the conditions of 298K and 1bar, carbon dioxide, the methane of 2 gained crystal of embodiment
There is certain increase with nitrogen adsorption capacity, and is calculated according to Ideal adsorption solution theory it is found that embodiment 2 has preferable titanium dioxide
Carbon/methane and carbon dioxide/nitrogen separation performance (shown in attached drawing 11).
*Inorg.Chem.2015,54,9862-9868(doi:10.1021/acs.inorgchem.5b01611)。
Claims (4)
1. a kind of nitrogen oxygen mixed ligand Zn complex, which is characterized in that its chemical formula is [Zn2(L1)2L2], wherein L1For 1,3,5-
Three (2- methyl-1 H- imidazoles) benzene ligands (I), L2For Isosorbide-5-Nitrae-phthalic acid or derivatives thereof, (I) structural formula is as follows:
(I)
The nitrogen oxygen mixed ligand Zn complex crystal belongs to monoclinic system, I 2/a space group, and with 3,4-c connection network
Formed crystal structure, point symbol be { 3.8^2 } 3 { 8^3.9^3 }, cell parameter be a=19.356 (3), b=11.6626 (15), c=
36.722 (6), α=90, β=102.233 (2), γ=90 °, V=8101.453；
The 1,4- derivates select 1,4- phthalic acid, 2- amino -1,4- phthalic acid, 2,5- dihydroxy -1,4-
Phthalic acid or the fluoro- 1,4- phthalic acid of 2,3,5,6- tetra-.
2. the method for preparing nitrogen oxygen mixed ligand Zn complex as described in claim 1, which is characterized in that including walking as follows
It is rapid:
(1) L is prepared1Ligand: 1,3,5- tribromo-benzene, 2-methylimidazole, potassium carbonate and copper sulphate are mixed and are ground uniformly, are packed into
In polytetrafluoro liner reactor, baking oven heating reaction is put into after nitrogen purging；After reaction, it is down to room temperature, pumping is washed with water
Retain filter residue after filter, extracted, filtered, revolving obtains ligand L1；
(2) L for preparing step (1)1Ligand, L2The mixing of N,N-dimethylformamide and water is added in ligand and zinc nitrate hexahydrate
In solvent, concentrated nitric acid is then added dropwise, stirring to solution is clarified；
(3) clear solution prepared by step (2) is moved in vial, is covered, be placed in baking oven and heat reaction, reaction terminates
Afterwards, it is filtered, is washed, it is dry, obtain nitrogen oxygen mixed ligand Zn complex；
The L2Ligand selects 1,4- phthalic acid, 2- amino -1,4- phthalic acid, 2,5- dihydroxy -1,4- phthalic acid or 2,3,
The fluoro- 1,4- phthalic acid of 5,6- tetra-.
3. the preparation method of nitrogen oxygen mixed ligand Zn complex as claimed in claim 2, which is characterized in that L in step (2)1Match
Body, L2Ligand and zinc nitrate hexahydrate molar ratio are 2:2:5.
4. the preparation method of nitrogen oxygen mixed ligand Zn complex as claimed in claim 2, which is characterized in that baking oven in step (3)
Reaction temperature is 80 DEG C.
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| CN113877362A (en) * | 2021-10-12 | 2022-01-04 | 西安近代化学研究所 | Selective adsorption and separation method for nitrogen and near gas |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102070659A (en) * | 2010-12-02 | 2011-05-25 | 南开大学 | Zinc organic complex as well as preparation method and application thereof |
| CN104098614A (en) * | 2014-07-23 | 2014-10-15 | 苏州大学 | Zinc coordination polymer as well as preparation method and application thereof |
| CN105732670A (en) * | 2016-01-28 | 2016-07-06 | 洛阳师范学院 | Auto-entangled microporous fluorescent material and preparation method thereof |
| CN106147197A (en) * | 2016-06-30 | 2016-11-23 | 北京化工大学 | A kind of fuel cell many conduction sites polyphenyl ether anion exchange membrane and preparation method thereof |
| CN108623816A (en) * | 2018-07-06 | 2018-10-09 | 陕西理工大学 | A kind of micropore zinc (II) coordination polymer crystal and the preparation method and application thereof |
| CN109369692A (en) * | 2018-11-28 | 2019-02-22 | 新乡学院 | A kind of synthesis for the complex that flexible three imidazole ligands are constructed |
| CN109762178A (en) * | 2019-02-11 | 2019-05-17 | 洛阳师范学院 | A kind of metal-organic framework materials, metal-organic framework materials of rhodamine B-sensitized and its preparation method and application |
-
2019
- 2019-07-31 CN CN201910698155.XA patent/CN110330515B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102070659A (en) * | 2010-12-02 | 2011-05-25 | 南开大学 | Zinc organic complex as well as preparation method and application thereof |
| CN104098614A (en) * | 2014-07-23 | 2014-10-15 | 苏州大学 | Zinc coordination polymer as well as preparation method and application thereof |
| CN105732670A (en) * | 2016-01-28 | 2016-07-06 | 洛阳师范学院 | Auto-entangled microporous fluorescent material and preparation method thereof |
| CN106147197A (en) * | 2016-06-30 | 2016-11-23 | 北京化工大学 | A kind of fuel cell many conduction sites polyphenyl ether anion exchange membrane and preparation method thereof |
| CN108623816A (en) * | 2018-07-06 | 2018-10-09 | 陕西理工大学 | A kind of micropore zinc (II) coordination polymer crystal and the preparation method and application thereof |
| CN109369692A (en) * | 2018-11-28 | 2019-02-22 | 新乡学院 | A kind of synthesis for the complex that flexible three imidazole ligands are constructed |
| CN109762178A (en) * | 2019-02-11 | 2019-05-17 | 洛阳师范学院 | A kind of metal-organic framework materials, metal-organic framework materials of rhodamine B-sensitized and its preparation method and application |
Non-Patent Citations (4)
| Title |
|---|
| JI-AI HUA，等: "Solvent-dependent zinc(II) coordination polymers with mixed ligands: selective sorption and fluorescence sensing", 《DALTON TRANS.》 * |
| JI-AI HUA，等: "Zinc(II) coordination polymers with substituted benzenedicarboxylate and tripodal imidazole ligands: syntheses, structures and properties", 《CRYST ENG COMM》 * |
| JIAN FAN，等: "Novel Metal-Organic Frameworks with Specific Topology from New Tripodal Ligands: 1,3,5-Tris(1-imidazolyl)benzene and 1,3-Bis(1-imidazolyl)-5-(imidazol-1-ylmethyl)benzene", 《INORG. CHEM》 * |
| YI HAN，等: "Diverse architectures of hybrid materials induced by different mixed-ligands and applications in luminescence", 《INORGANIC CHEMISTRY COMMUNICATIONS》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113877362A (en) * | 2021-10-12 | 2022-01-04 | 西安近代化学研究所 | Selective adsorption and separation method for nitrogen and near gas |
| CN113877362B (en) * | 2021-10-12 | 2023-09-12 | 西安近代化学研究所 | Method for selectively adsorbing and separating nitrogen and near gas |
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