CN105688842B - A kind of azo-type aromatic copolymer and azo-type aromatic copolymer porous material and preparation method and application - Google Patents
A kind of azo-type aromatic copolymer and azo-type aromatic copolymer porous material and preparation method and application Download PDFInfo
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- CN105688842B CN105688842B CN201610039889.3A CN201610039889A CN105688842B CN 105688842 B CN105688842 B CN 105688842B CN 201610039889 A CN201610039889 A CN 201610039889A CN 105688842 B CN105688842 B CN 105688842B
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
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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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- B01J20/28—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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Abstract
The invention discloses a kind of azo-type aromatic copolymer and azo-type aromatic copolymer porous material and preparation method and application；By the nitryl aromatic class compound with three dimensional topology under the catalysis of active metal and alkaloids, carry out coupling polymerization, up to azo-type aromatic copolymer, azo-type aromatic copolymer further activates under vacuum high-temperature, up to azo-type aromatic copolymer porous material, the azo-type aromatic copolymer porous material specific surface area is high, aperture can arbitrarily regulate and control in the larger context, and polymer thermostable is good, simultaneously polarity itrogen-to-nitrogen bonds is introduced in polymer, porous material is stored and is captured in gas, the numerous areas such as aromatic compound dangerous vapors separation, it has broad application prospects；And the preparation method of azo-type aromatic copolymer and porous material is simple, yield is high, facilitates feasible, suitable industrialized production.
Description
Technical field
The invention discloses a kind of azo-type aromatic copolymer and azo-type aromatic copolymer porous material and preparation methods
And application, belong to functional polymer material field.
Background technology
Under a large amount of combustion of fossil fuel for heat production, electricity production, the carbon dioxide about 13,000,000,000 that is discharged into every year in air
Ton, a series of problems, such as so as to cause climate warming, greenhouse effects.It is infeasible in limitation CO2 emission, two
The capture and utilization of carbonoxide have great significance to the sustainable development of China's economy.CO at present2Capture technique be mainly
Using ammonia spirit, but ammonium hydroxide has corrosivity, toxicity and volatility, it is most important that, the method is chemisorption, and regeneration disappears
Energy consumption is big.Porous organic polymer be different from ammonia spirit be can be by physical method selective absorption CO2, regenerate energy
Consumption is few.The class that carbon capture is present material, the energy and Environmental Studies field hot spot the most is carried out using micropore organic polymer
One of topic has especially great learning value and industrial application value.
But current most of porous organic polymers are weaker to guest molecule adsorption, it is difficult to meet practical application
It is required that.It can be enhanced to CO by carrying out functionalization in hole surface2Adsorption capacity and improve CO2/N2Separation selectivity, therefore
It is most promising method that the hetero atoms such as N are introduced in micropore organic polymer.By the modification to monomer building block, by many richnesses
The group of the atom containing N, such as diazole, imidazoles, triazine are introduced into micropore organic polymer backbones, successfully improve material
Gas separating property.Such as PPFs [Y.Zhu, H.Long, W.Zhang, the Imine-linked porous reported recently
polymer frameworks with high small gas(H2,CO2,CH4,C2H2)uptake and CO2/
N2Selectivity, Chem.Mater.25 (2013) 1630-1635.] etc..However item needed for the synthesis of such nitrogen-functionalization
Part is complicated, and most microporous polymer is made of single building block, and structure is single, specific surface area is low, and can not be to its property
Can specific surface area, carbon dioxide adsorption separation etc. effectively regulated and controled.
With the fast development of new and high technology, the comprehensive performance and hole of environment and new energy field to porous organic polymer
More stringent requirements are proposed for gap regulation and control.And existing porous organic polymer is difficult to meet the needs of application.
Invention content
For current porous organic polymer material, there are single properties, and specific surface area is low, and can not be to its specific surface area
And the performances such as carbon dioxide adsorption separation carry out the defect of Effective Regulation, the purpose of the invention is to provide one kind by a variety of tools
There is the porous polymer that the aryl unit of three dimensional topology is made up of nitrogen-nitrogen key coupling, which can pass through
It selects the different aryl units with three dimensional topology and copolymerization ratios to regulate and control, while introducing azo isopolarity list
Member.
Second object of the present invention is to be to provide a kind of stability good, and specific surface area is high, and aperture and specific surface area
The azo-type aromatic copolymer porous material that can regulate and control in wide range.
Third object of the present invention is to be to provide a kind of easy to operate, and reaction condition is mild, easily controllable, efficiently
The method for preparing the azo-type aromatic copolymer.
Fourth object of the present invention be to provide a kind of easy to operate, reaction condition it is mild prepare the azo-type
The method of aromatic copolymer porous material.
It is weak to micro-molecular gas adsorption capacity for current porous organic polymer material, the problems such as adsorption capacity is low, this hair
The 5th bright purpose is to be to provide a kind of azo organic copolymer Porous materials in aromatic compound dangerous vapors
Separation carbon dioxide gas capture and the application that detaches aspect, and the porous material absorption amount is big, reversibility of adsorption is good, repeatable
It uses, there is wide application prospect.
In order to achieve the above technical purposes, the present invention provides a kind of azo-type aromatic copolymer, the polymer is by having
The aryl unit of three dimensional topology is made up of nitrogen-nitrogen key coupling；
The aryl unit is In at least two.
The porous aromatic copolymer structure of azo-type of the present invention：(as shown in 1 structure of following formula：It is with Ar 'For illustrate)
Wherein,Indicate constitutional repeating unit.
Originally it returns and provides a kind of azo-type aromatic copolymer porous material, the porous material is by the azo-type fragrance
The powder or granular materials that copolymer is constituted.
Preferred scheme, inside powder or granular materials average pore size between 0.5~100nm, specific surface area 800~
2000m2Between/g.It the aperture of porous material can be even by selecting the different aryl units with three dimensional topology to build
Nitrogen type aromatic copolymer come realize regulation and control.Average pore size is between 0.5~2.5nm inside most preferred powder or granular materials,
Specific surface area is in 820~1500m2Between/g；By the aperture of porous material and specific surface area control in the preferred scope, make more
Porous materials are strong to the adsorption capacity of carbon dioxide and benzene vapour etc. and adsorption capacity is larger, have more preferably adsorption effect.
The present invention also provides a kind of method preparing the azo-type aromatic copolymer, this method is that will have three-dimensional
The nitryl aromatic class compound of topological structure under the catalysis of active metal and alkaloids, carry out coupling polymerization to get；
The nitryl aromatic class compound is In at least two.
These nitryl aromatic class compounds that the present invention uses can use for reference existing literature report synthesis, or directly buy
It obtains.
Preferred scheme, coupling polymerization be at a temperature of 40~70 DEG C reaction 5~for 24 hours.Most preferably at a temperature of 60 DEG C
Reaction is for 24 hours.
Preferred scheme, active metal are at least one of zinc, magnesium, copper, nickel, aluminium, titanium, tungsten or molybdenum.More preferably it is zinc.
Preferred scheme, alkaloids be sodium hydroxide, potassium hydroxide, ammonium nitrate, sodium carbonate or sodium bicarbonate at least
It is a kind of.More preferably it is potassium hydroxide.
Preferred scheme, coupling polymerization are sub- using tetrahydrofuran, toluene, n,N-Dimethylformamide, dimethyl in the process
At least one of sulfone, DMAC N,N' dimethyl acetamide, N-Methyl pyrrolidone dissolve the nitryl aromatic class compound.More preferably
The nitryl aromatic class compound is dissolved using N,N-dimethylformamide.
Preferred scheme, coupling polymerization crude product first uses salt acid elution, then uses water, tetrahydrofuran, chloroform successively
After being washed with acetone, under 0.001~0.01MPa vacuum conditions, it is total to get azo-type fragrance to be heated to 105~125 DEG C of dryings
Polymers.
The present invention also provides a kind of method preparing azo-type aromatic copolymer porous material, this method is will be described
Azo-type aromatic copolymer under 0.001~0.01MPa vacuum conditions, be heated to 180~250 DEG C of activation process to get.
Preferred scheme, activation process time are 2~48h；More preferably it is 48h.
Preferred scheme, activating treatment temperature are 200 DEG C.
In technical scheme of the present invention, pass through the choosing of the type to the nitryl aromatic class compound with three dimensional topology
It selects, and difference has the adjusting of the composite reaction ratio of the nitryl aromatic class compound of three dimensional topology；Realize azo-type
The aperture of aromatic copolymer is controllable between 0.5~100nm, and specific surface area is in 800~2000m2It is controllable between/g.
The present invention also provides the applications of the azo-type aromatic copolymer porous material, and the porous material is answered
For being selectively adsorbing and separating for carbon dioxide gas and/or aromatic compound steam.
Compared with the prior art, the advantageous effects that technical scheme of the present invention is brought：
1, a kind of azo-type being made up of nitrogen-nitrogen key coupling the aryl unit with three dimensional topology is obtained for the first time
Aromatic copolymer is coupled, molecule thermal stability is good, and introduces polar nitrogen nitrogen base with porous structure by nitrogen-nitrogen key
Group, makes molecular polarity be changed.
2, azo-type aromatic copolymer of the invention and its porous material specific surface area height and pore size and ratio of composition
Surface area can need to only select different reaction raw materials to combine and match, you can to realize regulation and control arbitrarily to regulate and control in a certain range.One
As can control internal average pore size between 0.5~100nm, specific surface area is in 800~2000m2Between/g.
3, the porous material preparation method of azo-type aromatic copolymer of the invention and its composition is easy to operate, reaction condition
Mildly, at low cost, meet demand of industrial production.
4, azo-type aromatic copolymer porous material of the invention passes through physical method CO absorption2, it is small that regeneration consumes energy；
With traditional porous organic polymer ratio, copolymer can control the specific surface area of synthetic copolymer by adjusting the content of building block
With pore volume and Kong Rong；The copolymer of azo functionalization is to N2Adsorption capacity is weaker, thus in CO2And N2The separation of mixed gas
Etc. having much potentiality.Copolymer has adjustable high specific surface area and big Kong Rong, is based on these characteristics, and this kind of material is being catalyzed
The numerous areas such as agent carrier, gas store and capture, metal ion advanced treating and aromatic compound dangerous vapors detach have
Wide application prospect.
Description of the drawings
【Fig. 1】For 1 azo-type aromatic copolymer of embodiment and the infrared comparison diagram of monomer.
【Fig. 2】For the thermogravimetric curve under the nitrogen environment of 1 azo-type aromatic copolymer of embodiment.
【Fig. 3】For the graph of pore diameter distribution of 1 azo-type aromatic copolymer of embodiment.
Specific implementation mode
The following examples are further illustrations of the invention, rather than limitation is of the invention.
Specific embodiment of the invention reaction intermediate structured testing carries out on following apparatus：In VARIAN1000 types
FT-IR tests are carried out on infrared spectrometer, with KBr pressed disc method sample preparations；Thermogravimetric analysis (TGA) is in PERKIN ELMER TGA7 heat
(10 DEG C/min of heating rate, 25~800 DEG C of test scope) is carried out on analyzer；Specific surface area and pore-size distribution are in ASAP
It is tested (77.3K) on 2020 (Micromeritics) volumetric adsorption analyzer；
Embodiment 1
In the 100mL three-necked flasks with mechanical agitation, thermometer, reflux condensing tube and drying tube, successively by 2,7,
14- trinitro- triptycenes 7mmol, 2,2 ', 7,7 '-tetranitro spiral shell, two fluorenes 3mmol are dissolved into the DMF mixing of the THF and 8mL of 7mL
In liquid, the sodium hydroxide, 1.47g zinc powders and 3mL deionized waters of 1.38g are added, 60 DEG C are warming up under stirring, in nitrogen protection
Under the conditions of react 24 hours.It after reaction solution filtering, with salt acid elution filter residue, is then washed with water, acetone, is produced up to thick after dry
Product.Heated under vacuum of the crude product in 0.001MPa handles 48h to get Porous materials to 180 DEG C, and BET specific surface area is
823m2/ g, average pore size 0.59nm, 5% thermal weight loss temperature is 270 DEG C under condition of nitrogen gas.Dioxy under 273K and 1 atmospheric pressure
The adsorbance for changing carbon is 3.24mmol/g, CO under 273K2/N2Selectivity be 90.Benzene vapour load capacity is 187.3wt%
(353K,1bar)。
Embodiment 2
In the 100mL three-necked flasks with mechanical agitation, thermometer, reflux condensing tube and drying tube, instill 8mL's
In DMF, 2,2,2 ', 2 '-tetramethyl -5,5- dinitro -1,1- loop coil, two indane 3mmol, 4,4 ', 4 "-trinitro-s are sequentially added
Triphenylamine 7mmol, 1.47g zinc powder, the potassium hydroxide of 1.41g and 3mL deionized waters, are warming up to 70 DEG C under stirring, protected in nitrogen
It is reacted 16 hours under the conditions of shield.It after reaction solution filtering, with salt acid elution filter residue, is then washed with water, THF and acetone, after dry
Up to crude product.Heated under vacuum of the crude product in 0.001MPa handles 48h to get Porous materials to get hole material to 190 DEG C
Material, BET specific surface area 950m2/ g, average pore size 1.25nm, 5% thermal weight loss temperature is 292 DEG C under condition of nitrogen gas.
The adsorbance of 273K and 1 atmospheric pressure carbon dioxide is 3.19mmol/g, CO under 273K2/N2Selectivity be 43.Benzene vapour
Load capacity is 141.8wt% (353K, 1bar).
Embodiment 3
In the 100mL three-necked flasks with mechanical agitation, thermometer, reflux condensing tube and drying tube, the two of 6mL are instilled
In methyl sulfoxide, sequentially add 4,4 ', 4 ", 4 " '-tetranitro Tetrabenzene methane 4mmol, 4,4 ', 4 "-trinitro- triphenylamine 4mmol,
1.47g zinc powders, the ammonium nitrate of 2.1g and 2.8mL deionized waters, are warming up to 65 DEG C under stirring, react 20 under the conditions of nitrogen protection
Hour.Reaction solution after filtering, with salt acid elution filter residue.Filter residue is carried through water, THF and acetone rope respectively, is produced up to thick after dry
Product.Heated under vacuum of the crude product in 0.001MPa handles 48h to get Porous materials to get Porous materials, BET to 180 DEG C
Specific surface area is 1310m2/ g, average pore size 2.18nm, 5% thermal weight loss temperature is 359 DEG C under condition of nitrogen gas.273K and 1
The adsorbance of atmospheric pressure carbon dioxide is 3.59mmol/g, CO under 273K2/N2Selectivity be 29.Benzene vapour load capacity is
178.4wt% (353K, 1bar).
Embodiment 4
Under reaction condition same as Example 3, it is 7 to sequentially add molar ratio：The 4,4 ' of 3,4 ", 4 " '-tetranitros four
Phenylmethane and 4,4 ', 4 "-trinitro- triphenylamines carry out cross-coupling polymerization, obtain crude product.Vacuum of the crude product in 0.001MPa
Under the conditions of be heated to 180 DEG C processing 48h to get Porous materials to get Porous materials, BET specific surface area 1280m2/ g, average hole
Diameter is 2.32nm, and 5% thermal weight loss temperature is 371 DEG C under condition of nitrogen gas.The adsorbance of 273K and 1 atmospheric pressure carbon dioxide is
CO under 3.24mmol/g, 273K2/N2Selectivity be 41.Benzene vapour load capacity is 181.9wt% (353K, 1bar).
Embodiment 5
Under reaction condition same as Example 3, it is 3 to sequentially add molar ratio：The 4,4 ' of 7,4 ", 4 " '-tetranitros four
Phenylmethane and 4,4 ', 4 "-trinitro- triphenylamines carry out cross-coupling polymerization, obtain crude product.Vacuum of the crude product in 0.001MPa
Under the conditions of be heated to 180 DEG C processing 48h to get Porous materials to get Porous materials, BET specific surface area 1138m2/ g, average hole
Diameter is 2.01nm, and 5% thermal weight loss temperature is 348 DEG C under condition of nitrogen gas.The adsorbance of 273K and 1 atmospheric pressure carbon dioxide is
CO under 3.46mmol/g, 273K2/N2Selectivity be 52.Benzene vapour load capacity is 167.1wt% (353K, 1bar).
Claims (7)
1. a kind of azo-type aromatic copolymer porous material, it is characterised in that：The powder that be made of azo-type aromatic copolymer or
Granular materials；
The azo-type aromatic copolymer is made up of the aryl unit with three dimensional topology nitrogen-nitrogen key coupling；It is described
Aryl unit be In at least two；
Average pore size is between 0.5~100nm inside the powder or granular materials, and specific surface area is in 800~2000m2/ g it
Between.
2. the method for preparing azo-type aromatic copolymer porous material, it is characterised in that：By the nitro with three dimensional topology
Aromatic compounds carry out coupling polymerization to get azo-type aromatic copolymer under the catalysis of active metal and alkaloids；It will
The azo-type aromatic copolymer under 0.001~0.01MPa vacuum conditions, be heated to 180~250 DEG C of activation process to get；
The nitryl aromatic class compound is In at least two.
3. the method according to claim 2 for preparing azo-type aromatic copolymer porous material, it is characterised in that：Described
Coupling polymerization be at a temperature of 40~70 DEG C reaction 5~for 24 hours.
4. the method according to claim 2 for preparing azo-type aromatic copolymer porous material, it is characterised in that：Described
Active metal is at least one of zinc, magnesium, copper, nickel, aluminium, titanium, tungsten or molybdenum；The alkaloids are sodium hydroxide, hydrogen-oxygen
Change at least one of potassium, ammonium nitrate, sodium carbonate or sodium bicarbonate.
5. the method according to claim 2 for preparing azo-type aromatic copolymer porous material, it is characterised in that：
Using tetrahydrofuran, toluene, N,N-dimethylformamide, dimethyl sulfoxide (DMSO), N, N- dimethyl second during coupling polymerization
At least one of amide, N-Methyl pyrrolidone dissolve the nitryl aromatic class compound；
Coupling polymerization crude product first uses salt acid elution, then after being washed successively with water, tetrahydrofuran, chloroform and acetone, in
Under 0.001~0.01MPa vacuum conditions, 105~125 DEG C of dryings are heated to get azo-type aromatic copolymer.
6. the method according to claim 2 for preparing azo-type aromatic copolymer porous material, it is characterised in that：At activation
The reason time is 2~48h.
7. the application of azo-type aromatic copolymer porous material described in claim 1, it is characterised in that：Applied to aromatics
Object steam is selectively adsorbing and separating.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102258986A (en) * | 2011-06-27 | 2011-11-30 | 华北电力大学（保定） | Molecular imprinting absorbent for separating CO2 in smoke and application thereof |
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| CN102258986A (en) * | 2011-06-27 | 2011-11-30 | 华北电力大学（保定） | Molecular imprinting absorbent for separating CO2 in smoke and application thereof |
Non-Patent Citations (3)
| Title |
|---|
| "Facile synthesis of azo-linked porous organic frameworks via reductive homocoupling for selective CO2 capture";Jingzhi Lu et al;《Journal of Materials Chemistry A》;20140702;第2卷;第13831-13834页 * |
| "An azo-linked porous triptycene network as an absorbent for CO2 and iodine uptake";Qin-Qin Dang et al;《Polymer Chemistry》;20151123;第7卷;实验部分和流程图1 * |
| "Directing the Structural Features of N2-Phobic Nanoporous Covalent Organic Polymers for CO2 Capture and Separation";Hasmukh A. Patel et al;《ChemPubSoc Europe》;20131211;第20卷;图1 * |
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