CN105688842A - Azo-type aromatic copolymer and azo-type aromatic copolymer porous material as well as preparation methods and application - Google Patents
Azo-type aromatic copolymer and azo-type aromatic copolymer porous material as well as preparation methods and application Download PDFInfo
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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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- B01D—SEPARATION
- B01D53/00—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
- 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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- B01J20/28057—Surface area, e.g. B.E.T specific surface area
- B01J20/28064—Surface area, e.g. B.E.T specific surface area being in the range 500-1000 m2/g
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
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- 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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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Abstract
The invention discloses an azo-type aromatic copolymer and an azo-type aromatic copolymer porous material as well as preparation methods and application. The azo-type aromatic copolymer is obtained by coupling and polymerizing a nitryl aromatic compound with a three-dimensional topological structure under the catalysis of active metal and alkali type substances; the azo-type aromatic copolymer porous material is obtained by further activating the azo-type aromatic copolymer in vacuum and at a high temperature. The azo-type aromatic copolymer porous material is high in specific surface area, and a pore diameter of the material can be randomly regulated and adjusted in a larger range; the thermal stability of the polymer is good; meanwhile, a polar nitrogen-nitrogen bond is introduced into the polymer, and the porous material has a wide application prospect in a plurality of fields including gas storage and capturing, separation of aromatic compound harmless steam and the like; the preparation methods of the azo-type aromatic copolymer and the azo-type aromatic copolymer porous material are simple, high in yield and convenient and feasible, and are suitable for industrial production.
Description
Technical field
The invention discloses a kind of azo-type aromatic copolymer and azo-type aromatic copolymer porous material and preparation method and application, belong to functional high polymer material field。
Background technology
For heat production, electrogenesis a large amount of combustion of fossil fuel under, be discharged into the carbon dioxide in air about 13,000,000,000 tons every year, thus causing the series of problems such as climate warming, greenhouse effect。In the restriction infeasible situation of CO2 emission, the catching and utilize the sustainable development to China's economy to have great significance of carbon dioxide。Current CO2Capture technique mainly adopt ammonia spirit, but ammonia has corrosivity, toxicity and volatility, it is most important that, the method is chemisorbed, and regeneration consumed energy is big。What porous organic polymer was different from ammonia spirit is to pass through physical method selective absorption CO2, regenerated energy consumption is few。Adopting micropore organic polymer to carry out, carbon catches is one of the problem of present material, the energy and environmental studies field focus the most, has learning value great especially and industrial application value。
But current most of porous organic polymer is more weak to guest molecule adsorption, it is difficult to meet the requirement of practical application。Can strengthen CO by carrying out functionalization at hole surface2Absorption affinity and improve CO2/N2Separation selectivity, therefore introducing the hetero atoms such as N in micropore organic polymer is the most promising method。By the modification to monomer building block, by many groups rich in atom N, it is incorporated in micropore organic polymer backbones such as diazole, imidazoles, triazine etc., successfully improves the gas separating property of material。Such as PPFs [Y.Zhu, H.Long, W.Zhang, the Imine-linkedporouspolymerframeworkswithhighsmallgas (H reported recently2,CO2,CH4,C2H2)uptakeandCO2/N2Selectivity, Chem.Mater.25 (2013) 1630-1635.] etc.。But complicated condition needed for the synthesis of this kind of nitrogen-functionalization, and most microporous polymer is to be made up of single building block, structure is single, specific surface area is low, and cannot its performance such as specific surface area, carbon dioxide adsorption separation etc. effectively be regulated and controled。
Along with combination property and the hole regulation and control of porous organic polymer are had higher requirement by the fast development of new and high technology, environment and new energy field。And existing porous organic polymer is difficult to meet the demand of application。
Summary of the invention
Single property is there is for current porous organic polymer material, specific surface area is low, and the performances such as its specific surface area and carbon dioxide adsorption separation cannot be carried out the defect of Effective Regulation, it is an object of the invention to be in that to provide a kind of porous polymer being made up of the multiple aryl unit with three dimensional topology by nitrogen-nitrogen key coupling, this polymer aperture by selecting the different aryl unit with three dimensional topology and copolymerization ratios to regulate and control, can be simultaneously introduced azo isopolarity unit。
Second purpose of the present invention is to be in that to provide a kind of good stability, and specific surface area is high, and the azo-type aromatic copolymer porous material that aperture and specific surface area can regulate and control in a big way。
3rd purpose of the present invention is to be in that to provide a kind of easy and simple to handle, and reaction condition is gentle, it is easy to the method control, prepared described azo-type aromatic copolymer efficiently。
4th purpose of the present invention is to be in that to provide a kind of simple to operate, method preparing described azo-type aromatic copolymer porous material that reaction condition is gentle。
For current porous organic polymer material, micro-molecular gas absorption affinity is weak, the problems such as adsorption capacity is low, 5th purpose of the present invention be in that to provide the separation at aromatic dangerous vapors of a kind of described azo organic copolymer Porous materials or carbon dioxide catch with separate in application, porous material absorption amount is big, reversibility of adsorption good for this, reusable, it is widely applied prospect。
In order to realize above-mentioned technical purpose, the invention provides a kind of azo-type aromatic copolymer, this polymer is consisted of nitrogen-nitrogen key coupling the aryl unit with three dimensional topology；
Described aryl unit is Middle at least two。
The azo-type porous aromatic copolymer structure of the present invention: (as shown in following formula 1 structure: with Ar ' forIllustrate for example)
Wherein,Represent constitutional repeating unit。
Originally return and provide a kind of azo-type aromatic copolymer porous material, powder that this porous material is made up of described azo-type aromatic copolymer or granular materials。
The internal average pore size of preferred scheme, powder or granular materials is between 0.5～100nm, and specific surface area is at 800～2000m2Between/g。The aperture of porous material can by selecting the different aryl unit structure azo-type aromatic copolymers with three dimensional topology to realize regulation and control。Most preferred powder or the internal average pore size of granular materials are between 0.5～2.5nm, and specific surface area is at 820～1500m2Between/g；The aperture of porous material and specific surface area are controlled in this preferable range, make porous material that high adsorption capacity and the adsorption capacity of carbon dioxide and benzene vapour etc. is relatively big, there is adsorption effect more preferably。
Present invention also offers a kind of method preparing described azo-type aromatic copolymer, the method be the nitryl aromatic compounds by having three dimensional topology under the catalysis of active metal and alkaloids, carry out coupling polymerization, to obtain final product；
Described nitryl aromatic compounds is Middle at least two。
These nitryl aromatic compounds that the present invention adopts can use for reference the synthesis of existing bibliographical information, or is directly commercially available。
Preferred scheme, coupling polymerization is reaction 5～24h at 40～70 DEG C of temperature。It most preferably is at 60 DEG C of temperature and reacts 24h。
Preferred scheme, active metal is at least one in zinc, magnesium, copper, nickel, aluminum, titanium, tungsten or molybdenum。It is more preferably zinc。
Preferred scheme, alkaloids is at least one of sodium hydroxide, potassium hydroxide, ammonium nitrate, sodium carbonate or sodium bicarbonate。It it is more preferably potassium hydroxide。
Preferred scheme, adopts at least one in oxolane, toluene, DMF, dimethyl sulfoxide, N,N-dimethylacetamide, N-Methyl pyrrolidone to dissolve described nitryl aromatic compounds in coupling polymerization process。N,N-dimethylformamide is more preferably adopted to dissolve described nitryl aromatic compounds。
Preferred scheme, coupling polymerization crude product first adopts salt acid elution, more successively with after water, oxolane, chloroform and washing with acetone, under 0.001～0.01MPa vacuum condition, is heated to 105～125 DEG C and dries, obtain azo-type aromatic copolymer。
Present invention also offers a kind of method preparing azo-type aromatic copolymer porous material, the method be by described azo-type aromatic copolymer under 0.001～0.01MPa vacuum condition, be heated to 180～250 DEG C of activation processing, to obtain final product。
Preferred scheme, the activation processing time is 2～48h；It is more preferably 48h。
Preferred scheme, activating treatment temperature is 200 DEG C。
In technical scheme, by the selection of the type to the nitryl aromatic compounds with three dimensional topology, and difference has the adjustment of composite reaction ratio of nitryl aromatic compounds of three dimensional topology；Realizing aperture controllable between 0.5～100nm of azo-type aromatic copolymer, specific surface area is at 800～2000m2Controllable between/g。
Present invention also offers the application of described azo-type aromatic copolymer porous material, described porous material is applied to being selectively adsorbing and separating of carbon dioxide and/or aromatic steam。
Hinge structure, the Advantageous Effects that technical scheme is brought:
1, a kind of azo-type aromatic copolymer being made up of by nitrogen-nitrogen key coupling the aryl unit with three dimensional topology is obtained first, it has loose structure, by nitrogen-nitrogen key coupling, molecule Heat stability is good, and introduce the nitrogen nitrogen groups of polarity, make molecular polarity be changed。
2, the porous material specific surface area of the azo-type aromatic copolymer of the present invention and composition thereof is high and pore size and specific surface area can arbitrarily regulation and control in certain limit, only need to select different reaction raw materials combinations and proportioning, regulation and control can be realized。Generally can controlling internal average pore size between 0.5～100nm, specific surface area is at 800～2000m2Between/g。
3, the azo-type aromatic copolymer of the present invention and the porous material preparation method of composition thereof are simple to operate, and reaction condition is gentle, and cost is low, meets demand of industrial production。
4, the azo-type aromatic copolymer porous material of the present invention passes through physical method CO absorption2, regeneration consumed energy is little；With traditional porous organic polymer ratio, copolymer can pass through to regulate the specific surface area of the content control synthetic copolymer of building block and pore volume and pore volume；The copolymer of azo functionalization is to N2Absorption affinity is more weak, thus at CO2And N2The separation etc. of mixing gas has much potentiality。The numerous areas such as copolymer has adjustable high specific surface area and big pore volume, and based on these characteristics, this kind of material stores at catalyst carrier, gas and catches, metal ion advanced treating separates with aromatic dangerous vapors have broad application prospects。
Accompanying drawing explanation
[Fig. 1] is the infrared comparison diagram of embodiment 1 azo-type aromatic copolymer and monomer。
[Fig. 2] is the thermogravimetric curve under the nitrogen environment of embodiment 1 azo-type aromatic copolymer。
[Fig. 3] is the graph of pore diameter distribution of embodiment 1 azo-type aromatic copolymer。
Detailed description of the invention
Following example are further illustrating the present invention, rather than the restriction present invention。
Specific embodiment of the invention reaction intermediate structured testing carries out on following apparatus: carry out FT-IR test on VARIAN1000 type infrared spectrometer, with KBr pressed disc method sample preparation；Thermogravimetric analysis (TGA) carries out (10 DEG C/min of heating rate tests scope 25～800 DEG C) on PERKINELMERTGA7 thermal analyzer；Specific surface area and pore-size distribution carry out testing (77.3K) on ASAP2020 (Micromeritics) volumetricadsorptionanalyzer；
Embodiment 1
In the 100mL there-necked flask with mechanical agitation, thermometer, reflux condensing tube and drying tube; successively by 2; 7; 14-trinitro-triptycene 7mmol, 2,2 ', 7; 7 '-tetranitro spiral shell two fluorenes 3mmol is dissolved in the DMF mixed liquor of THF and the 8mL of 7mL; add the sodium hydroxide of 1.38g, 1.47g zinc powder and 3mL deionized water, under stirring, be warming up to 60 DEG C, react 24 hours when nitrogen protection。After reacting liquid filtering, with salt acid elution filtering residue, then with water, washing with acetone, namely obtain thick product after drying。Thick product processes 48h at the heated under vacuum to 180 DEG C of 0.001MPa, obtains Porous materials, and its BET specific surface area is 823m2/ g, average pore size is 0.59nm, and under condition of nitrogen gas, 5% thermal weight loss temperature is 270 DEG C。The adsorbance of 273K and 1 atmospheric pressure carbon dioxide is CO under 3.24mmol/g, 273K2/N2Selectivity be 90。Benzene vapour load capacity is 187.3wt% (353K, 1bar)。
Embodiment 2
In the 100mL there-necked flask with mechanical agitation, thermometer, reflux condensing tube and drying tube; instill in the DMF of 8mL, be sequentially added into 2,2; 2 '; 2 '-tetramethyl-5,5-dinitro-1,1-volution two indane 3mmol, 4; 4 '; 4 "-trinitro-triphenylamine 7mmol, 1.47g zinc powder, the potassium hydroxide of 1.41g and 3mL deionized water, be warming up to 70 DEG C under stirring, reacts 16 hours when nitrogen protection。After reacting liquid filtering, with salt acid elution filtering residue, then with water, THF and washing with acetone, namely obtain thick product after drying。Thick product processes 48h at the heated under vacuum to 190 DEG C of 0.001MPa, obtains Porous materials, obtains Porous materials, and its BET specific surface area is 950m2/ g, average pore size is 1.25nm, and under condition of nitrogen gas, 5% thermal weight loss temperature is 292 DEG C。The adsorbance of 273K and 1 atmospheric pressure carbon dioxide is CO under 3.19mmol/g, 273K2/N2Selectivity be 43。Benzene vapour load capacity is 141.8wt% (353K, 1bar)。
Embodiment 3
In the 100mL there-necked flask with mechanical agitation, thermometer, reflux condensing tube and drying tube; instill in the dimethyl sulfoxide of 6mL; it is sequentially added into 4; 4 ', 4 ", 4 " '-tetranitro Tetrabenzene methane 4mmol, 4; 4 '; 4 "-trinitro-triphenylamine 4mmol, 1.47g zinc powder, the ammonium nitrate of 2.1g and 2.8mL deionized water, be warming up to 65 DEG C under stirring, reacts 20 hours when nitrogen protection。Reactant liquor after filtering, with salt acid elution filtering residue。Filtering residue carries through water, THF and acetone rope respectively, namely obtains thick product after drying。Thick product processes 48h at the heated under vacuum to 180 DEG C of 0.001MPa, obtains Porous materials, obtains Porous materials, and its BET specific surface area is 1310m2/ g, average pore size is 2.18nm, and under condition of nitrogen gas, 5% thermal weight loss temperature is 359 DEG C。The adsorbance of 273K and 1 atmospheric pressure carbon dioxide is CO under 3.59mmol/g, 273K2/N2Selectivity be 29。Benzene vapour load capacity is 178.4wt% (353K, 1bar)。
Embodiment 4
Under the reaction condition identical with embodiment 3, be sequentially added into that mol ratio is 7:3 4,4 ', 4 ", 4 " '-tetranitro Tetrabenzene methane and 4,4 ', 4 "-trinitro-triphenylamine carries out cross-coupling polymerization, obtains thick product。Thick product processes 48h at the heated under vacuum to 180 DEG C of 0.001MPa, obtains Porous materials, obtains Porous materials, and its BET specific surface area is 1280m2/ g, average pore size is 2.32nm, and under condition of nitrogen gas, 5% thermal weight loss temperature is 371 DEG C。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 the reaction condition identical with embodiment 3, be sequentially added into that mol ratio is 3:7 4,4 ', 4 ", 4 " '-tetranitro Tetrabenzene methane and 4,4 ', 4 "-trinitro-triphenylamine carries out cross-coupling polymerization, obtains thick product。Thick product processes 48h at the heated under vacuum to 180 DEG C of 0.001MPa, obtains Porous materials, obtains Porous materials, and its BET specific surface area is 1138m2/ g, average pore size is 2.01nm, and under condition of nitrogen gas, 5% thermal weight loss temperature is 348 DEG C。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 (10)
1. an azo-type aromatic copolymer, it is characterised in that: it is made up of by nitrogen-nitrogen key coupling the aryl unit with three dimensional topology；
Described aryl unit is Middle at least two。
2. an azo-type aromatic copolymer porous material, it is characterised in that: powder that the azo-type aromatic copolymer described in claim 1 is constituted or granular materials。
3. azo-type aromatic copolymer porous material according to claim 2, it is characterised in that: powder or the internal average pore size of granular materials are between 0.5～100nm, and specific surface area is at 800～2000m2Between/g。
4. the method for preparation azo-type aromatic copolymer described in claim 1, it is characterised in that: by there is the nitryl aromatic compounds of three dimensional topology under the catalysis of active metal and alkaloids, carrying out coupling polymerization, to obtain final product；
Described nitryl aromatic compounds is Middle at least two。
5. the method preparing azo-type aromatic copolymer according to claim 4, it is characterised in that: described coupling polymerization is reaction 5～24h at 40～70 DEG C of temperature。
6. the method preparing azo-type aromatic copolymer according to claim 4, it is characterised in that: described active metal is at least one in zinc, magnesium, copper, nickel, aluminum, titanium, tungsten or molybdenum；Described alkaloids is at least one of sodium hydroxide, potassium hydroxide, ammonium nitrate, sodium carbonate or sodium bicarbonate。
7. the method preparing azo-type aromatic copolymer according to claim 4, it is characterised in that:
Coupling polymerization process adopt at least one in oxolane, toluene, N,N-dimethylformamide, dimethyl sulfoxide, DMAC N,N' dimethyl acetamide, N-Methyl pyrrolidone dissolve described nitryl aromatic compounds；
Coupling polymerization crude product first adopts salt acid elution, more successively with after water, oxolane, chloroform and washing with acetone, under 0.001～0.01MPa vacuum condition, is heated to 105～125 DEG C and dries, obtain azo-type aromatic copolymer。
8. the method preparing azo-type aromatic copolymer porous material, it is characterised in that: azo-type aromatic copolymer claim 3～7 any one method prepared, under 0.001～0.01MPa vacuum condition, is heated to 180～250 DEG C of activation processing, to obtain final product。
9. the method preparing azo-type aromatic copolymer porous material according to claim 8, it is characterised in that: the activation processing time is 2～48h。
10. the application of the azo-type aromatic copolymer porous material described in Claims 2 or 3, it is characterised in that: it is applied to being selectively adsorbing and separating of carbon dioxide and/or aromatic steam。
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Cited By (3)
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| CN107488261A (en) * | 2017-06-14 | 2017-12-19 | 中南大学 | A kind of rich carboxylic micropore organic polymer material and preparation method thereof |
| CN110756059A (en) * | 2019-11-04 | 2020-02-07 | 华东理工大学 | Preparation method of mixed matrix membrane with porous ionic polymer as disperse phase and application of mixed matrix membrane in gas separation |
| CN110787663A (en) * | 2019-11-15 | 2020-02-14 | 中南大学 | High permeability polymer composite membrane for gas separation and method of making the same |
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| US20130139834A1 (en) * | 2006-12-07 | 2013-06-06 | British American Tobacco (Investments) Limited | Polymers Selective for Nitro-Containing Compounds and Methods of Using the Same |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107488261A (en) * | 2017-06-14 | 2017-12-19 | 中南大学 | A kind of rich carboxylic micropore organic polymer material and preparation method thereof |
| CN110756059A (en) * | 2019-11-04 | 2020-02-07 | 华东理工大学 | Preparation method of mixed matrix membrane with porous ionic polymer as disperse phase and application of mixed matrix membrane in gas separation |
| CN110756059B (en) * | 2019-11-04 | 2021-12-03 | 华东理工大学 | Preparation method of mixed matrix membrane with porous ionic polymer as disperse phase and application of mixed matrix membrane in gas separation |
| CN110787663A (en) * | 2019-11-15 | 2020-02-14 | 中南大学 | High permeability polymer composite membrane for gas separation and method of making the same |
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