CN109232886A - A kind of preparation method and application of the conjugation microporous polymer based on carbazole group - Google Patents
A kind of preparation method and application of the conjugation microporous polymer based on carbazole group Download PDFInfo
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- CN109232886A CN109232886A CN201810858381.5A CN201810858381A CN109232886A CN 109232886 A CN109232886 A CN 109232886A CN 201810858381 A CN201810858381 A CN 201810858381A CN 109232886 A CN109232886 A CN 109232886A
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0666—Polycondensates containing five-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0672—Polycondensates containing five-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only one nitrogen atom in the ring
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- 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
- B01D53/14—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 absorption
- B01D53/1493—Selection of liquid materials for use as absorbents
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/20—Organic absorbents
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- B01D2252/2053—Other nitrogen compounds
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Abstract
The preparation method and application for being conjugated microporous polymer based on carbazole group that the present invention provides a kind of, sequence carries out according to the following steps for it: 0.32 ~ 0.48 mmol monomer, 30 mL anhydrous organic solvents and the anhydrous catalyst of 2.5 ~ 3.0 mmol are sequentially added in the pressure pipe that high temperature drying is crossed, and it is passed through inert gas and empties pressure-resistant inner air tube, it is protected from light magnetic agitation 20-30 h at 160 ~ 180 DEG C, 100 mL alcohols are added and terminate reaction.Stop heating, room temperature magnetic agitation 15-60min, filtering, gained precipitating successively uses methanol, concentrated hydrochloric acid, pure water rinsing three times, gained crude product is placed in Soxhlet extractor, 24 h of Soxhlet extraction successively is distinguished with alcohols, organic solvent, tetrahydrofuran, and products therefrom is obtained into black powder in 65-85 DEG C of 24 h of vacuum drying.The present invention is applied to CO2The absorption of equal sour gas.
Description
Technical field
The invention belongs to capillary copolymer material fields, are related to a kind of system of conjugation microporous polymer based on carbazole group
Preparation Method and application.
Background technique
Greenhouse effects cause the living environment of the mankind and seriously threaten, CO2Emission reduction and trapping become the mankind concern
Key subjects, for CO2Trapping, the method industrially absorbed frequently with solution, although such method, which has, absorbs fast, technique letter
Single, the advantages that treating capacity is big, but the energy consumption of this method is high, severe corrosion equipment in the process, substantially increases industrial cost.
And solid absorbent is because of the advantages that its energy consumption is low, corrosion-free equipment, it has also become CO2One important research direction of trapping.Currently,
For CO2The solid absorbent of trapping has very much, wherein conjugation microporous polymer is due to stable chemical property, biggish
The features such as specific surface area, uniform narrow nanoscale pore-size distribution and lower skeletal density, shows in gas absorption aspects
Huge development prospect.
Due to conjugation microporous polymer absorption and store the performance of gas by the space structure of monomer, duct pattern with
And various influences such as effective chemical group, and the space structure of monomer is determining for the final absorbent properties of microporous polymer
Qualitative factor, therefore seek suitable monomer material, it is real to obtain the conjugation microporous polymer for possessing better steric configuration
Existing CO2Efficient trapping be research conjugation microporous polymer important goal.
Summary of the invention
The purpose of the present invention is to provide for a kind of preparation method of conjugation microporous polymer based on carbazole group and answers
With to be combined into monomer, synthetic polymer, by the sky for increasing monomer to be conjugated intercalated nucleus and carbazole group of good performance
Between torsion resistance to increase the specific surface area of polymer realize good gas absorption performance.
To achieve the above object, used technical solution is as follows by the present invention:
The preparation method for being conjugated microporous polymer based on carbazole group that the present invention provides a kind of, the preparation method press following step
Rapid sequence carries out:
Sequentially added in the pressure pipe that high temperature drying is crossed 0.32 ~ 0.48 mmol monomer, 30 mL anhydrous organic solvents and 2.5 ~
The anhydrous catalyst of 3.0 mmol, and be passed through inert gas and empty pressure-resistant inner air tube, magnetic agitation 20- is protected from light at 160 ~ 180 DEG C
30 h are added 100 mL alcohols and terminate reaction.
Stop heating, room temperature magnetic agitation 15-60min, filtering, gained precipitating is successively with methanol, concentrated hydrochloric acid, pure water rinsing
Three times, gained crude product is placed in Soxhlet extractor, successively uses alcohols, organic solvent, 24 h of tetrahydrofuran Soxhlet extraction, it will
Products therefrom obtains black powder in 65-85 DEG C of 24 h of vacuum drying, and a kind of as described conjugation micropore based on carbazole group is poly-
Close object.
As a kind of restriction of the invention, the monomer is the structural formula both ends being formed by connecting by carbazole group and intercalated nucleus
For carbazole group, center is the compound of intercalated nucleus.
It is further limited as of the invention, the intercalated nucleus is the compound of the group containing electron rich.
As second of restriction of the invention, the synthetic method of the monomer sequentially carries out according to the following steps:
(1) activation of copper powder
160 ~ 240 mg Cu powder are weighed, is added in 200 mL conical flasks, sequentially adds the dense HCl of 5 mL and 100 mL acetone, magnetic force
25-35min is stirred, is filtered.Adding into acetone will be precipitated, 3 ~ 5 iodine grains are added, 25 ~ 35min of magnetic agitation continues to activate, will
Obtained rufous Cu powder filters out the catalyst as next step reaction.
(2) synthesis of monomer
Under inert gas shielding, sequentially added in the dry pyriform reaction flask of 100 mL 1.20 ~ 1.90 mmol intercalated nucleus, 750 ~
Copper powder, 4.5 ~ 8.0 mmol potassium carbonate and the 20 mL nitrobenzenes that 1000 mg carbazoles, 160 ~ 240 mg are activated.Oil bath heating is to anti-
160 ~ 200 DEG C of temperature are answered, magnetic agitation is for 24 hours.
It is cooled to room temperature after reaction, is distilled nitrobenzene solution with oil pump, room temperature adds after distillation
Enter 30 mL ammonium hydroxide magnetic agitation, 3 h and removes catalyst.Then, organic extractant phase, organic phase nothing are carried out with water and methylene chloride
Water Na2SO4Dry, Rotary Evaporators are spin-dried for methylene chloride, and gained crude product carries out separating-purifying with silicagel column and obtains the list
Body.
As the third restriction of the invention, the organic solvent is in chloroform, carbon tetrachloride, acetone and methylene chloride
It is a kind of.
As the 4th kind of restriction of the invention, the anhydrous catalyst is anhydrous ferric trichloride.
As the 5th kind of restriction of the invention, the inert gas is one or both of nitrogen, argon gas.
As the 6th kind of restriction of the invention, the alcohols is one of methanol, ethyl alcohol, ethylene glycol, isopropanol.
The application for being conjugated microporous polymer based on carbazole group that the present invention also provides a kind of, it is described to be based on carbazole group
Conjugation microporous polymer be applied to sour gas trapping.
There are also a kind of restriction, the conjugation microporous polymers based on carbazole group to be applied to CO by the present invention2Trapping.
Due to the adoption of the above technical solution, compared with prior art, the present invention acquired beneficial effect is:
Carbazole is a kind of azaaromatics with rigid condensed cyclic structure in the present invention.Such compound is with higher
Photo and thermal stability, the azacyclo- in structure is to CO2Equal sour gas have certain absorption, biggish conjugated system in structure
So that the compound molecule is had the function of stronger interior electric charge transfer and certain specific functional group can be introduced under certain condition, because
And it is with certain designability, is the ideal material of synthesis of conjugate microporous polymer.
In the present invention be conjugated microporous polymer not only have stable chemical property, biggish specific surface area, uniformly it is narrow
Nanoscale pore-size distribution and the features such as lower skeletal density, and it selects different intercalated nucleus that can synthesize different spaces
The poromerics of configuration, to CO2Equal sour gas have good absorbent properties.
A kind of preparation method of conjugation microporous polymer based on carbazole group provided by the invention has easy to operate, nothing
Pollution, it is low in cost the advantages that, this method has huge application prospect in field of environment protection and gas storage art.
Detailed description of the invention
Fig. 1 is the synthetic route chart of polymer PC z-TT-Cz；
Fig. 2 is the synthetic route chart of polymer PC z-DTBT-Cz；
Fig. 3 is respectively the steric configuration figure of polymer PC z-TT-Cz and polymer PC z-DTBT-Cz；
Fig. 4 is respectively the graph of pore diameter distribution of polymer PC z-TT-Cz and polymer PC z-DTBT-Cz；
Fig. 5 is the gas absorption performance data of polymer PC z-TT-Cz and polymer PC z-DTBT-Cz；
Fig. 6 is temperature and pressure respectively to the shadow of the gas absorption performance of polymer PC z-TT-Cz and polymer PC z-DTBT-Cz
It rings.
Specific embodiment
Below with reference to embodiment, the invention will be further described, it will be appreciated by those skilled in the art that the present invention and unlimited
In following embodiment, any improvements and changes made on the basis of the present invention are all within protection scope of the present invention.
Experimental method used in following embodiments is conventional method unless otherwise specified.
The materials, reagents and the like used in the following examples is commercially available unless otherwise specified.
The preparation method of the polymer PC z-TT-Cz of embodiment 1 a kind of
The preparation method sequentially carries out according to the following steps:
(1) activation of copper powder
200 mg Cu powder are weighed, is added in 200 mL conical flasks, sequentially adds the dense HCl of 5 mL and 100 mL acetone, magnetic agitation
30 min are filtered.Adding into acetone will be precipitated, 3 ~ 5 iodine grains are added, 30 min of stirring continue to activate, the rufous that will be obtained
Cu powder filters out the catalyst as next step reaction.
(2) synthesis of monomer
Under argon gas protection, 1.85 mmol compounds 1,928 mg carbazoles, 200 are sequentially added in the dry pyriform reaction flask of 100 mL
Copper powder, 7.4 mmol potassium carbonate and the 20 mL nitrobenzenes of mg activation.Oil bath heating is to 180 DEG C of reaction temperature, magnetic agitation
24h。
It is cooled to room temperature after reaction, is distilled nitrobenzene solution with oil pump, room temperature adds after distillation
Enter 30 mL ammonium hydroxide magnetic agitation, 3 h and removes catalyst.Then, carry out organic extractant phase with water and methylene chloride, after it is organic
Mutually use anhydrous Na2SO4Dry, Rotary Evaporators are spin-dried for solvent, and silica white fries sample loading, and silicagel column carries out separating-purifying.Eluant, eluent
The petroleum ether for being 4:1 for volume ratio: methylene chloride collects yellow colour band, obtains the monomer Cz-TT-Cz of final yellow powder, produces
Amount is 220 mg, yield 36.7%.
(3) synthesis of polymer PC z-TT-Cz
0.40 mmol monomer Cz-TT-Cz, 30 mL are sequentially added in the pressure pipe that high temperature drying is crossed through CaH2Dry chlorine
Imitative and 2.82 mmol anhydrous ferric trichlorides, and be passed through nitrogen and make to be protected from light magnetic agitation at 180 DEG C for oxygen-free environment in pressure pipe
100 mL methanol are added after 24 h and terminate reaction.
Stopping heating, 30 min of room temperature magnetic agitation, filtering precipitates and successively uses methanol, concentrated hydrochloric acid, pure water rinsing three times,
Gained crude product is placed in Soxhlet extractor, methanol, chloroform, 24 h of tetrahydrofuran Soxhlet extraction are successively used, by products therefrom
The polymer PC z-TT-Cz that 24 h obtain black powder is dried in vacuo at 80 DEG C.
The preparation method of 2 ~ 6 polymer PC z-TT-Cz of embodiment
Embodiment 2 ~ 6 be respectively polymer PC z-TT-Cz a kind of preparation method, the preparation method according to the following steps sequence into
Row: (1) activation of copper powder, the synthesis of (2) monomer, the synthesis of (3) polymer PC z-TT-Cz.
The operating procedure of embodiment 2 ~ 6 is similar to Example 1, only the type, dosage of intercalated nucleus, organic solvent,
The type and reaction temperature of alcohols and inert gas, reaction time, the yield etc. of product are different, specifically see the table below:
The preparation method of the polymer PC z-DTBT-Cz of embodiment 7 a kind of
The preparation method sequentially carries out according to the following steps:
(1) activation of copper powder
200 mg Cu powder are weighed, is added in 200 mL conical flasks, sequentially adds the dense HCl of 5 mL and 100 mL acetone, magnetic agitation
30 min are filtered.Adding into acetone will be precipitated, 3 ~ 5 iodine grains are added, 30 min of stirring continue to activate, the rufous that will be obtained
Cu powder filters out the catalyst as next step reaction.
(2) synthesis of monomer
Under argon gas protection, 1.24 mmol compounds 2,620 mg carbazoles, 200 are sequentially added in the dry pyriform reaction flask of 100 mL
Copper powder, 4.96 mmol potassium carbonate and the 20 mL nitrobenzenes of mg activation.Oil bath heating is to 180 DEG C of reaction temperature, magnetic agitation
24h。
It is cooled to room temperature after reaction, is distilled nitrobenzene solution with oil pump, room temperature adds after distillation
Enter 30 mL ammonium hydroxide magnetic agitation, 3 h and removes catalyst.Then, carry out organic extractant phase with water and methylene chloride, after it is organic
Mutually use anhydrous Na2SO4Dry, Rotary Evaporators are spin-dried for solvent, and silica white fries sample loading, and silicagel column carries out separating-purifying.Eluant, eluent
The petroleum ether for being 4:1 for volume ratio: methylene chloride collects aubergine colour band, obtains the monomer Cz- of final aubergine powder
DTBT-Cz, yield are 240 mg, and yield is 42.0 %.
(3) synthesis of polymer PC z-DTBT-Cz
0.37 mmol monomer Cz-DTBT-Cz, 30 mL are sequentially added in the pressure pipe that high temperature drying is crossed through CaH2Dry
Chloroform and 2.55 mmol anhydrous ferric trichlorides, and be passed through nitrogen and make to be protected from light magnetic force for oxygen-free environment at 180 DEG C and stir in pressure pipe
The termination reaction of 100 mL methanol is added after mixing 24 h.
Stopping heating, 30 min of room temperature magnetic agitation, filtering precipitates and successively uses methanol, concentrated hydrochloric acid, pure water rinsing three times,
Gained crude product is placed in Soxhlet extractor, methanol, chloroform, 24 h of tetrahydrofuran Soxhlet extraction are successively used, by products therefrom
The polymer PC z-DTBT-Cz that 24 h obtain black powder is dried in vacuo at 80 DEG C.
The preparation method of 8 ~ 12 polymer PC z-DTBT-Cz of embodiment
Embodiment 8 ~ 12 be respectively polymer PC z-DTBT-Cz a kind of preparation method, the preparation method according to the following steps sequence
It carries out: (1) activation of copper powder, the synthesis of (2) monomer, the synthesis of (3) polymer PC z-DTBT-Cz.
The operating procedure of embodiment 8 ~ 12 is similar to Example 7, only the type, dosage of intercalated nucleus, organic solvent,
The type and reaction temperature of alcohols and inert gas, reaction time, the yield etc. of product are different, specifically see the table below:
The steric configuration and pore-size distribution of embodiment 13 polymer PC z-TT-Cz and polymer PC z-DTBT-Cz
Fig. 3 (a) is the steric configuration of polymer PC z-TT-Cz, and Fig. 3 (b) is the steric configuration of polymer PC z-DTBT-Cz.
Fig. 4 (a) is the pore-size distribution of polymer PC z-TT-Cz, as shown, the main aperture of polymer PC z-TT-Cz is distinguished
Cloth exists in 0.54 ~ 1.00 nm, only a small amount of mesoporous distribution greater than 2 nm, no macropore；
Fig. 4 (b) is the pore-size distribution of polymer PC z-DTBT-Cz, as shown, the main aperture of polymer PC z-DTBT-Cz is distinguished
Cloth has a certain amount of mesoporous distribution for being greater than 2 nm in 0.52 ~ 1.00 nm.
The gas absorption performance of embodiment 14 polymer PC z-TT-Cz and polymer PC z-DTBT-Cz
Fig. 5 is the gas absorption performance data of polymer PC z-TT-Cz and polymer PC z-DTBT-Cz, as shown, polymer
PCz-DTBT-Cz has stronger gas sorption ability compared with polymer PC z-TT-Cz, and chief reason may be two kinds of polymer
Accumulation pattern affects CO to a certain extent2Adsorbance, the packed structures of polymer PC z-DTBT-Cz filiform are more advantageous to
CO2The attachment of molecule increases the specific surface of material additionally due to intercalated nucleus DTBT makes the spatial warping degree of polymer become larger
Product, the collective effect of the two make CO2Adsorption capacity enhancing.
15 temperature and pressure of embodiment is respectively to the gas absorption of polymer PC z-TT-Cz and polymer PC z-DTBT-Cz
The influence of performance
Fig. 6 is temperature and pressure respectively to the shadow of the gas absorption performance of polymer PC z-TT-Cz and polymer PC z-DTBT-Cz
Ring, as can be seen from the figure at 273K, 1bar polymer PC z-DTBT-Cz CO2Adsorbance is 13.1wt%.298K, 1bar
The CO of lower polymer PC z-DTBT-Cz2Adsorbance is 8.9wt%.The CO of polymer PC z-TT-Cz at 273K, 1bar2Adsorbance
For 9.5wt%.The CO of polymer PC z-TT-Cz under 298K, 1bar2Adsorbance is 7.7wt%.
It can be seen from the results above that two kinds of polymer has certain CO under conditions of 1bar in 273K and 298K2It inhales
Attached amount, but at 273K, 1bar, the CO of polymer PC z-DTBT-Cz2Adsorbance is 1.38 times of polymer PC z-TT-Cz, main
The reason of wanting may be that the accumulation pattern of two kinds of polymer affects CO to a certain extent2Adsorbance, polymer PC z-
The packed structures of DTBT-Cz filiform are more advantageous to CO2The attachment of molecule, additionally due to intercalated nucleus DTBT makes the space of polymer
Torsion resistance becomes larger, and increases the specific surface area of material, and the collective effect of the two makes CO2Adsorption capacity enhancing.
Embodiment 1-15 is only presently preferred embodiments of the present invention, is not the limit of other forms made for the present invention
Fixed, any person skilled in the art is changed or is modified as equivalent change as enlightenment possibly also with above-mentioned technology contents
The equivalent embodiment of change.But all technical spirits without departing from the claims in the present invention are simple to made by above embodiments
Modification, equivalent variations and remodeling still fall within the range of the claims in the present invention protection.
Claims (10)
1. a kind of preparation method of the conjugation microporous polymer based on carbazole group, it is characterised in that: the preparation method is by following
Sequence of steps carries out:
Sequentially added in the pressure pipe that high temperature drying is crossed 0.32 ~ 0.48 mmol monomer, 30 mL anhydrous organic solvents and 2.5 ~
The anhydrous catalyst of 3.0 mmol, and be passed through inert gas and empty pressure-resistant inner air tube, magnetic agitation 20- is protected from light at 160 ~ 180 DEG C
30 h are added 100 mL alcohols and terminate reaction；
Stop heating, room temperature magnetic agitation 15-60min, filtering, gained precipitating is successively with methanol, concentrated hydrochloric acid, pure water rinsing three
Time, gained crude product is placed in Soxhlet extractor, alcohols, organic solvent, 24 h of tetrahydrofuran Soxhlet extraction are successively used, by institute
It obtains product and obtains black powder in 65-85 DEG C of 24 h of vacuum drying, a kind of as described conjugation microporous polymer based on carbazole group
Object.
2. a kind of preparation method of conjugation microporous polymer based on carbazole group as described in claim 1, it is characterised in that:
The monomer is that the structural formula both ends being formed by connecting by carbazole group and intercalated nucleus are carbazole group, and center is the chemical combination of intercalated nucleus
Object.
3. a kind of preparation method of conjugation microporous polymer based on carbazole group as claimed in claim 2, it is characterised in that:
The intercalated nucleus is the compound of the group containing electron rich.
4. a kind of preparation method of conjugation microporous polymer based on carbazole group as described in claim 1, it is characterised in that:
The synthetic method of the monomer sequentially carries out according to the following steps:
(1) activation of copper powder
160 ~ 240 mg Cu powder are weighed, is added in 200 mL conical flasks, sequentially adds the dense HCl of 5 mL and 100 mL acetone, magnetic force
25-35min is stirred, is filtered, adding into acetone will be precipitated, 3 ~ 5 iodine grains are added, 25 ~ 35min of magnetic agitation continues to activate, will
Obtained rufous Cu powder filters out the catalyst as next step reaction；
(2) synthesis of monomer
Under inert gas shielding, sequentially added in the dry pyriform reaction flask of 100 mL 1.20 ~ 1.90 mmol intercalated nucleus, 750 ~
1000 mg carbazoles, 160 ~ 240 mg activation copper powder, 4.5 ~ 8.0 mmol potassium carbonate and 20 mL nitrobenzenes, oil bath heating is to anti-
Answer 160 ~ 200 DEG C of temperature, magnetic agitation for 24 hours,
It is cooled to room temperature after reaction, is distilled nitrobenzene solution with oil pump, room temperature is added 30 after distillation
3 h of mL ammonium hydroxide magnetic agitation removes catalyst, then, carries out organic extractant phase with water and methylene chloride, and organic phase is with anhydrous
Na2SO4Dry, Rotary Evaporators are spin-dried for methylene chloride, and gained crude product carries out separating-purifying with silicagel column and obtains the monomer.
5. a kind of preparation method of conjugation microporous polymer based on carbazole group as described in claim 1, it is characterised in that:
The organic solvent is one of chloroform, carbon tetrachloride, acetone and methylene chloride.
6. a kind of preparation method of conjugation microporous polymer based on carbazole group as described in claim 1, it is characterised in that:
The anhydrous catalyst is anhydrous ferric trichloride.
7. a kind of preparation method of conjugation microporous polymer based on carbazole group as described in claim 1 or 4, feature exist
In: the inert gas is one or both of nitrogen, argon gas.
8. a kind of preparation method of conjugation microporous polymer based on carbazole group as described in claim 1, it is characterised in that:
The alcohols is one of methanol, ethyl alcohol, ethylene glycol, isopropanol.
9. a kind of application of the conjugation microporous polymer based on carbazole group, it is characterised in that: being total to based on carbazole group
Yoke microporous polymer is applied to the trapping of sour gas.
10. a kind of application of conjugation microporous polymer based on carbazole group as claimed in claim 9, it is characterised in that: institute
The conjugation microporous polymer based on carbazole group is stated applied to CO2Trapping.
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| CN115073714A (en) * | 2022-08-04 | 2022-09-20 | 浙江吉泰新材料股份有限公司 | Polycarbazole with side chain containing nitroxide free radical and preparation method and application thereof |
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Application publication date: 20190118 |