CN108751163A - A kind of preparation method of nitrogen-doped porous carbon material - Google Patents
A kind of preparation method of nitrogen-doped porous carbon material Download PDFInfo
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- CN108751163A CN108751163A CN201810782862.2A CN201810782862A CN108751163A CN 108751163 A CN108751163 A CN 108751163A CN 201810782862 A CN201810782862 A CN 201810782862A CN 108751163 A CN108751163 A CN 108751163A
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- C01B32/00—Carbon; Compounds thereof
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
- B01J20/20—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising free carbon; comprising carbon obtained by carbonising processes
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28054—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their surface properties or porosity
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
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Abstract
The present invention provides a kind of preparation method of nitrogen-doped porous carbon material.Cuprous chloride catalyst with nanoscale is prepared using solvent-thermal method, select 1,3,5- triaminobenzenes, 1, either other combination of monomers for having similar structures prepare the covalent organic framework material with regular aperture or irregular bore diameter porous material to 4- dibromobenzenes under the catalysis of stannous chloride nanocrystal.The porous material nitrogen element content of the method disclosed in the present preparation is high, pore structure is abundant, with big specific surface area, gas absorption performance is good, not only enrich the preparation method of nitrogen-doped porous carbon material, also have operating procedure simple and practicable, preparation process is not high to equipment requirement, the features such as being easy to industrialized mass production.
Description
Technical field
The invention belongs to gas adsorption material preparation field more particularly to a kind of preparation sides of nitrogen-doped porous carbon material
Method.
Background technology
Porous carbon materials due to having many advantages, such as that hydrophobic, density is low, stability is good, specific surface area is high, physicochemical property is adjustable,
People are caused in recent years and are extensively studied interest, are applied to the fields such as gas storage, heterogeneous catalysis and organic photoelectric.
Nitrogen is introduced in carbon material can further adjust structure, surface chemical property and the electronic conductivity of material, make it have
More wide application development prospect.Nitrogen-doped porous carbon material in addition to have the advantages that porous carbon materials it is all other than, with its solely
Special machinery, electronics, optical property etc. is further in the application range of absorption, superhard material, catalysis and fuel cell etc.
Expand.The introducing of nitrogen-atoms can change the Cloud Distribution of carbon-coating, play the role of raising heat of adsorption, improve adsorptive selectivity,
Therefore nitrogen-doped porous carbon material is considered as a kind of ideal adsorbent.
Traditional nitrogen atom doping complex procedures, cost is higher, and doping level is limited.Meanwhile building porous structure
Template is not suitable for mass producing.New synthetic method is explored, exploitation preparation method is simple, controllable, has high nitrogen-containing
And the abundant Nitrogen-rich porous carbon material of pore passage structure becomes the key subject in current porous carbon materials field, to N doping porous carbon
The research and development of material has great importance.
Invention content
A kind of preparation method of nitrogen-doped porous carbon material is proposed, using stannous chloride nanocrystal as catalyst,
Prepare the nitrogen-doped porous carbon material for having covalent organic framework.
The present invention adopts the following technical scheme that：
A kind of preparation method of nitrogen-doped porous carbon material, includes the following steps：
(1) chlorination copper powders are placed in autoclave, ethyl alcohol is added, be uniformly mixed, react one at a certain temperature
It the section time, is cooled to room temperature, decompression filters, and vacuum drying obtains the cuprous chloride catalyst with nanoscale；
(2) by the aromatic amino compounds such as 1,3,5- triaminobenzene, Isosorbide-5-Nitrae-dibromobenzene and stannous chloride nanocrystal or
Other combination of monomers for having similar structures of person are distributed in organic solvent, at a certain temperature, in certain time, certain solvent
In, under inert gas shielding, synthesize nitrogen-doped porous carbon material.
For a period of time, temperature is preferably 160 DEG C for reaction at a certain temperature in step (1), and the time is preferably for 24 hours.
Cuprous chloride catalyst size is 2~10nm in step (1).
The aromatic amino compounds such as 1,3,5- triaminobenzenes include 1,3,5- triaminobenzenes, 2,4,6- tri- in step (2)
Ethylo benzene -1,3,5- trimethylamines, 2,4,6- trimethylbenzenes -1,3,5- triamines, 1,3,5- triamidos -2,4,6- trinitrobenzens and its
Derivative.
The mass ratio of 1,3,5- triaminobenzenes, Isosorbide-5-Nitrae-dibromobenzene and the total amount of stannous chloride nanocrystal in step (2)
Preferably 0.5: 1: 0.1.
Other in step (2) have similar structures combination of monomers include 1,3,5- tribromo-benzenes and p-phenylenediamine, 1,3,5-
Triaminobenzene and 1,3- dibromobenzenes, 1,3,5- tribromo-benzene and 1,3- diaminobenzenes etc..
In step (2) reaction temperature be 0~380 DEG C, preferred temperature be 80 DEG C, the reaction process duration be 2h~
72h, preferred time are 12h, and solvent for use is the organic solvents such as acetonitrile, n,N-Dimethylformamide and dimethyl sulfoxide (DMSO), excellent
The solvent of choosing is acetonitrile.
The present invention has following advantage：
(1) nitrogen-doped porous carbon material is prepared using nanometer stannous chloride as the polycondensation reaction of catalyst, synthesis has
The covalent organic framework in regular aperture or the porous structure in irregular aperture, enrich the preparation of nitrogen-doped porous carbon material
Method.
(2) porous material prepared by the present invention, nitrogen element content is high, pore structure is abundant, with big specific surface area, gas
Body absorption property is good.
(3) operating procedure of the present invention is simple and practicable, and preparation process is not high to equipment requirement, is easy to industrialized mass production.
Description of the drawings
Fig. 1 is the schematic diagram for the covalent organic framework material that the method for the present invention synthesis has regular aperture.
Fig. 2 is the schematic diagram that the method for the present invention synthesizes irregular bore diameter porous material.
Fig. 3 is the transmission electron microscope picture of nitrogen-doped porous carbon material prepared by the method for the present invention.
Fig. 4 is the nitrogen adsorption desorption curve graph of nitrogen-doped porous carbon material prepared by the method for the present invention.
Specific implementation mode
Of the invention for ease of understanding, it is as follows that the present invention enumerates embodiment.Those skilled in the art are it will be clearly understood that the implementation
Example is used only for helping to understand the present invention, should not be regarded as a specific limitation of the invention.
Embodiment 1
(1) 0.8524g Copper dichloride dihydrates are weighed, the autoclave that volume is 50mL polytetrafluoroethyllining linings is placed in
In, 25mL ethyl alcohol is added, is uniformly mixed, kettle cover is covered tightly.
(2) autoclave is put in Muffle furnace, is reacted for 24 hours at 160 DEG C.It is cooled to room temperature, decompression filters, product
It is dried in vacuo 12h at 50 DEG C.Under nitrogen protection atmosphere, it is placed in shady place preservation, obtains the stannous chloride with 2~10nm
Nanocrystal.
(3) by 1,3, the 5- triaminobenzenes of 0.025g cuprous chloride crystals powder, 0.246g Isosorbide-5-Nitraes-dibromobenzene and 0.123g
It is dissolved in 5.0mL acetonitriles, nitrogen is added and forms protective atmosphere, temperature is maintained 80 DEG C, flow back 12h.
(4) reaction mixture therein is taken out, is washed respectively with 25% ammonium hydroxide, water, acetone, kept dry.
Fig. 1 includes the schematic diagram that the present embodiment prepares the covalent organic framework material with regular aperture.
Fig. 3 includes the transmission electron microscope picture that the present embodiment prepares nitrogen-doped porous carbon material.
Fig. 4 includes the nitrogen adsorption desorption curve graph of nitrogen-doped porous carbon material manufactured in the present embodiment.
Embodiment 2
(1) 0.8524g Copper dichloride dihydrates are weighed, the autoclave that volume is 50mL polytetrafluoroethyllining linings is placed in
In, 25mL ethyl alcohol is added, is uniformly mixed, kettle cover is covered tightly.
(2) autoclave is put in Muffle furnace, is reacted for 24 hours at 160 DEG C.It is cooled to room temperature, decompression filters, product
It is dried in vacuo 12h at 50 DEG C.Under nitrogen protection atmosphere, it is placed in shady place preservation, obtains the stannous chloride with 2~10nm
Nanocrystal.
(3) by 1,3, the 5- triaminobenzenes of 0.025g cuprous chloride crystals powder, 0.246g Isosorbide-5-Nitraes-dibromobenzene and 0.123g
It is dissolved in 5.0mL acetonitriles, nitrogen is added and forms protective atmosphere, temperature is maintained 120 DEG C, flow back 10h.
(4) reaction mixture therein is taken out, is washed respectively with 25% ammonium hydroxide, water, acetone, kept dry.
Embodiment 3
(1) 0.8524g Copper dichloride dihydrates are weighed, the autoclave that volume is 50mL polytetrafluoroethyllining linings is placed in
In, 25mL ethyl alcohol is added, is uniformly mixed, kettle cover is covered tightly.
(2) autoclave is put in Muffle furnace, is reacted for 24 hours at 160 DEG C.It is cooled to room temperature, decompression filters, product
It is dried in vacuo 12h at 50 DEG C.Under nitrogen protection atmosphere, it is placed in shady place preservation, obtains the stannous chloride with 2~10nm
Nanocrystal.
(3) by 2,4, the 6- triethyl groups of 0.025g cuprous chloride crystals powder, 0.236g Isosorbide-5-Nitraes-dibromobenzene and 0.249g
Benzene -1,3,5- trimethylamines are dissolved in 5.0mL acetonitriles, and nitrogen is added and forms protective atmosphere, temperature are maintained 120 DEG C, reflux
10h。
(4) reaction mixture therein is taken out, is washed respectively with 25% ammonium hydroxide, water, acetone, kept dry.
Embodiment 4
(1) 0.8524g Copper dichloride dihydrates are weighed, the autoclave that volume is 50mL polytetrafluoroethyllining linings is placed in
In, 25mL ethyl alcohol is added, is uniformly mixed, kettle cover is covered tightly.
(2) autoclave is put in Muffle furnace, is reacted for 24 hours at 160 DEG C.It is cooled to room temperature, decompression filters, product
It is dried in vacuo 12h at 50 DEG C.Under nitrogen protection atmosphere, it is placed in shady place preservation, obtains the stannous chloride with 2~10nm
Nanocrystal.
(3) by 2,4, the 6- trimethyls of 0.025g cuprous chloride crystals powder, 0.236g Isosorbide-5-Nitraes-dibromobenzene and 0.249g
Benzene -1,3,5- triamines are dissolved in 5.0mL acetonitriles, and nitrogen is added and forms protective atmosphere, temperature are maintained 120 DEG C, reflux
10h。
(4) reaction mixture therein is taken out, is washed respectively with 25% ammonium hydroxide, water, acetone, kept dry.
Embodiment 5
(1) 0.8524g Copper dichloride dihydrates are weighed, the autoclave that volume is 50mL polytetrafluoroethyllining linings is placed in
In, 25mL ethyl alcohol is added, is uniformly mixed, kettle cover is covered tightly.
(2) autoclave is put in Muffle furnace, is reacted for 24 hours at 160 DEG C.It is cooled to room temperature, decompression filters, product
It is dried in vacuo 12h at 50 DEG C.Under nitrogen protection atmosphere, it is placed in shady place preservation, obtains the stannous chloride with 2~10nm
Nanocrystal.
(3) by 1,3, the 5- triamidos-of 0.025g cuprous chloride crystals powder, 0.236g Isosorbide-5-Nitraes-dibromobenzene and 0.258g
2,4,6- trinitrobenzens are dissolved in 5.0mL acetonitriles, and nitrogen is added and forms protective atmosphere, temperature are maintained 120 DEG C, reflux
10h。
(4) reaction mixture therein is taken out, is washed respectively with 25% ammonium hydroxide, water, acetone, kept dry.
Embodiment 6
(1) 0.8524g Copper dichloride dihydrates are weighed, the autoclave that volume is 50mL polytetrafluoroethyllining linings is placed in
In, 25mL ethyl alcohol is added, is uniformly mixed, kettle cover is covered tightly.
(2) autoclave is put in Muffle furnace, is reacted for 24 hours at 160 DEG C.It is cooled to room temperature, decompression filters, product
It is dried in vacuo 12h at 50 DEG C.Under nitrogen protection atmosphere, it is placed in shady place preservation, obtains the stannous chloride with 2~10nm
Nanocrystal.
(3) 0.01g cuprous chloride crystals powder, 0.314g 1,3,5- tribromo-benzenes and 0.108g p-phenylenediamine are dissolved in
In 5.0mL acetonitriles, nitrogen is added and forms protective atmosphere, temperature is maintained 120 DEG C, flow back 10h.
(4) reaction mixture therein is taken out, is washed respectively with 25% ammonium hydroxide, water, acetone, kept dry.
Embodiment 7
(1) 0.8524g Copper dichloride dihydrates are weighed, the autoclave that volume is 50mL polytetrafluoroethyllining linings is placed in
In, 25mL ethyl alcohol is added, is uniformly mixed, kettle cover is covered tightly.
(2) autoclave is put in Muffle furnace, is reacted for 24 hours at 160 DEG C.It is cooled to room temperature, decompression filters, product
It is dried in vacuo 12h at 50 DEG C.Under nitrogen protection atmosphere, it is placed in shady place preservation, obtains the stannous chloride with 2~10nm
Nanocrystal.
(3) by 0.01g cuprous chloride crystals powder, 0.314g 1,3,5- tribromo-benzenes and 0.108g 1,3- diaminobenzenes are molten
Solution is added nitrogen and forms protective atmosphere in 5.0mL acetonitriles, and temperature is maintained 120 DEG C, and flow back 10h.
(4) reaction mixture therein is taken out, is washed respectively with 25% ammonium hydroxide, water, acetone, kept dry.
Fig. 2 lower parts include the synthesis schematic diagram that the present embodiment prepares porous material.
Embodiment 8
(1) 0.8524g Copper dichloride dihydrates are weighed, the autoclave that volume is 50mL polytetrafluoroethyllining linings is placed in
In, 25mL ethyl alcohol is added, is uniformly mixed, kettle cover is covered tightly.
(2) autoclave is put in Muffle furnace, is reacted for 24 hours at 160 DEG C.It is cooled to room temperature, decompression filters, product
It is dried in vacuo 12h at 50 DEG C.Under nitrogen protection atmosphere, it is placed in shady place preservation, obtains the stannous chloride with 2~10nm
Nanocrystal.
(3) by 0.025g cuprous chloride crystals powder, 0.246g 1,1,3,5- triaminobenzenes of 3- dibromobenzenes and 0.123g
It is dissolved in 5.0mL acetonitriles, nitrogen is added and forms protective atmosphere, temperature is maintained 80 DEG C, flow back 12h.
(4) reaction mixture therein is taken out, is washed respectively with 25% ammonium hydroxide, water, acetone, kept dry.
Subpackage method containing the present embodiment in the tops Fig. 2 prepares the synthesis schematic diagram of porous material.
Applicant states that the present invention illustrates detailed process equipment and the technological process of the present invention by above-described embodiment,
But the invention is not limited in above-mentioned detailed process equipment and technological processes, that is, it is above-mentioned detailed not mean that the present invention has to rely on
Process equipment and technological process could be implemented.Person of ordinary skill in the field it will be clearly understood that any improvement in the present invention,
The addition of equivalence replacement and auxiliary element to each raw material of product of the present invention, the selection etc. of concrete mode all fall within the present invention's
Within protection domain and the open scope.
Claims (7)
1. a kind of preparation method of nitrogen-doped porous carbon material, includes the following steps：
(1) chlorination copper powders are placed in autoclave, ethyl alcohol is added, be uniformly mixed, when reacting one section at a certain temperature
Between, it is cooled to room temperature, decompression filters, and vacuum drying obtains the cuprous chloride catalyst with nanoscale；
(2) by the aromatic amino compounds such as 1,3,5- triaminobenzene, Isosorbide-5-Nitrae-dibromobenzene and stannous chloride nanocrystal or its
The combination of monomers that he has similar structures is distributed in organic solvent, at a certain temperature, in certain time, in certain solvent,
Under inert gas shielding, nitrogen-doped porous carbon material is synthesized.
2. preparation method according to claim 1, which is characterized in that step reacts one at a certain temperature described in (1)
The section time, temperature is preferably 160 DEG C, and the time is preferably for 24 hours.
3. preparation method according to claim 1, which is characterized in that cuprous chloride catalyst size described in step (1)
For 2~10nm.
4. preparation method according to claim 1, which is characterized in that the virtues such as 1,3,5- triaminobenzenes described in step (2)
Fragrant race's amino-compound includes 1,3,5- triaminobenzenes, 2,4,6- triethylbenzenes -1,3,5- trimethylamines, 2,4,6- trimethylbenzenes -
1,3,5- triamine, 1,3,5- triamidos -2,4,6- trinitro- benzene and its derivatives.
5. preparation method according to claim 1, which is characterized in that 1,3,5- triaminobenzenes, Isosorbide-5-Nitrae-dibromo in step (2)
Benzene and the mass ratio of the total amount of stannous chloride nanocrystal are preferably 0.5: 1: 0.1.
6. preparation method according to claim 1, which is characterized in that other have similar structures described in step (2)
Combination of monomers include 1,3,5- tribromo-benzenes and p-phenylenediamine, 1,3,5- triaminobenzene and 1,3- dibromobenzenes, 1,3,5- tribromo-benzene and
1,3- diaminobenzene etc..
7. preparation method according to claim 1, which is characterized in that described in step (2) at a certain temperature, one timing
In, react in certain solvent, temperature is 0~380 DEG C, and preferred temperature is 80 DEG C, the reaction process duration be 2h~
72h, preferred time are 12h, and solvent for use is the organic solvents such as acetonitrile, n,N-Dimethylformamide and dimethyl sulfoxide (DMSO), excellent
The solvent of choosing is acetonitrile.
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| CN112108187A (en) * | 2020-09-27 | 2020-12-22 | 江南大学 | Copper-supported catalyst of biguanide-based covalent organic framework material and preparation method and application thereof |
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| CN108751163B (en) | 2021-09-14 |
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