CN113912805A - Organic porous polymer for catalyzing cycloaddition of epoxide and carbon dioxide - Google Patents
Organic porous polymer for catalyzing cycloaddition of epoxide and carbon dioxide Download PDFInfo
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- CN113912805A CN113912805A CN202111344010.3A CN202111344010A CN113912805A CN 113912805 A CN113912805 A CN 113912805A CN 202111344010 A CN202111344010 A CN 202111344010A CN 113912805 A CN113912805 A CN 113912805A
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- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
The invention discloses an organic porous polymer capable of being repeatedly used for catalyzing cycloaddition of epoxide and carbon dioxide and a preparation method thereof. Uniformly mixing an aromatic aldehyde compound, ethidium bromide and a reaction solvent; adding acetic acid, and reacting under the condition of heating and negative pressure; centrifuging at room temperature, washing, and vacuum drying to obtain the organic porous polymer. The polymer can catalyze the cycloaddition reaction of epoxide and carbon dioxide to generate cyclic carbonate under mild conditions, and can be separated from a product through high-speed centrifugation, and the polymer can be reused, so that more selectivity is provided for a heterogeneous catalyst for cycloaddition of epoxide and carbon dioxide.
Description
Technical Field
The invention belongs to the technical field of catalysts, and particularly relates to an organic porous polymer capable of being repeatedly used for catalyzing cycloaddition of epoxide and carbon dioxide and a preparation method thereof.
Background
Carbon dioxide is a major anthropogenic greenhouse gas, and excessive emissions pose many environmental problems, such as climate change and global warming. In an effort to reduce the carbon dioxide content of air, many researchers have focused on carbon dioxide capture, storage, and utilization. Carbon dioxide is an abundant, inexpensive and non-toxic chemical raw material, and is also a thermodynamically stable substance. Therefore, research and development of effective catalysts for reducing CO is required2Activation energy in the reaction, thereby converting CO2To a substance available in the chemical industry. Among them, cycloaddition of carbon dioxide and an epoxide to produce a cyclic carbonate has attracted much attention because of its hundred percent atomic utilization and high added value of the product.
Epoxides and carbon dioxide can be reacted directly to cyclic carbonates by catalytic reactions, and most of the catalysts used today are homogeneous catalysts, including phosphines, quaternary ammonium salts, transition metal complexes and alkali metal salts, because they enable the reaction to be carried out under mild conditions, sometimes even at room temperature and atmospheric pressure. However, the use of homogeneous catalysts still has problems such as removal of the catalyst from the reaction mixture after the reaction and recovery of the catalyst, and thus researchers have been encouraged to develop heterogeneous catalysts that can be recycled. Although many heterogeneous catalysts have been developed, catalysts that are mild in reaction conditions, environmentally friendly, and efficiently recoverable need to be further explored.
Disclosure of Invention
The invention aims to provide an organic porous polymer which can be repeatedly used for catalyzing cycloaddition of epoxide and carbon dioxide and a preparation method thereof. The polymer can catalyze the cycloaddition reaction of epoxide and carbon dioxide to generate cyclic carbonate under mild conditions, and can be separated from a product through high-speed centrifugation, and the polymer can be reused, so that more selectivity is provided for a heterogeneous catalyst for cycloaddition of epoxide and carbon dioxide.
In order to achieve the purpose, the invention adopts the following technical scheme:
the organic porous polymer capable of being repeatedly used for catalyzing cycloaddition of epoxide and carbon dioxide regulates and controls the distribution of active sites of a polymer catalyst material through an aromatic aldehyde compound, so that cyclic carbonate is generated by catalyzing cycloaddition of the epoxide and the carbon dioxide, and the catalyst and a product can be separated through centrifugation after the reaction is finished.
The organic porous polymer has the following specific general formula:
wherein R is aromatic aldehyde organic substances containing different benzene ring numbers (1-10).
The preparation method of the organic porous polymer comprises the following steps: the method comprises the following steps:
(1) adding aromatic aldehyde compound, ethidium bromide and reaction solvent into a schlenk tube, and uniformly mixing.
(2) Then, acetic acid was added as a catalyst and reacted under heating under negative pressure.
(3) After the reaction is finished, the solid is collected at room temperature, washed three times by using a solvent insoluble in the polymer, and dried in vacuum to obtain the organic porous polymer.
The aromatic aldehyde compound is any one of trimesic aldehyde, 3,4', 5-trioxadecyl-1, 1-biphenyl, 1,3, 5-tri (p-formylphenyl) benzene and 1,3, 5-tri (4' -formyl [1,1' -biphenyl ] -4-yl) benzene.
The reaction solvent is any one of 1, 4-dioxane standard solution, N-dimethylformamide, 1, 2-dichlorobenzene standard solution, N-butanol, 1,3, 5-trimethylhexahydro-1, 3, 5-triazine and dimethyl sulfoxide.
The reaction temperature in the step (2) is 100-160 ℃, and the reaction time is 2-6 days.
The washing solvent in the step (3) is any one of tetrahydrofuran, methanol and ethyl acetate.
The molar ratio of the aromatic aldehyde compound to the ethidium bromide to the reaction solvent to the acetic acid is 1.9-2.2: 3: 0.5-0.1: 0.0008-0.001.
The application of the organic porous polymer in catalyzing cycloaddition reaction of epoxide and carbon dioxide comprises the following steps:
(1) adding organic porous polymer and epoxide into a high-pressure reaction kettle, sealing, and filling CO at room temperature2Removing air in the kettle for the third time;
(2) filling with CO2Until the pressure in the reaction kettle reaches 0.6-1.8MPa, and the reaction is carried out for 6-15 hours at 50-150 ℃;
(3) centrifugally separating the catalyst organic porous polymer and the reaction product cyclic carbonate.
The epoxide is any one of epoxypropane, epichlorohydrin, epibromohydrin, styrene oxide, phenyl glycidyl ether, cyclohexene oxide and cyclopentane epoxide.
The invention has the beneficial effects that:
(1) the invention regulates the pore diameter and the distribution of catalytic active sites of the polymer through the aromatic aldehyde compound, is used for catalyzing the cycloaddition of epoxide and carbon dioxide, and has higher catalytic efficiency.
(2) The polymer prepared by the invention has the advantages of mild temperature and moderate pressure for catalyzing the cycloaddition reaction of the epoxide and the carbon dioxide.
(3) The polymer prepared by the invention has the advantages of multiple types of catalytic epoxide substrates, and no inactivation of the activity of the catalyst after repeated use.
(4) The polymer prepared by the invention has the advantage of no need of cocatalyst and solvent.
Drawings
FIG. 1 is an infrared spectrum of an organic porous polymer P3 obtained in example 3.
FIG. 2 shows the results of thermogravimetric analysis of the organic porous polymers P1, P2 and P3 obtained in example 1, example 2 and example 3.
FIG. 3 shows the results of the multi-use performance of the organic porous polymer P3 prepared in example 3 in catalyzing the cycloaddition of epoxide and carbon dioxide.
Detailed Description
In order to make the present invention more comprehensible, the technical solutions of the present invention are further described below with reference to specific embodiments, but the present invention is not limited thereto.
Example 1
0.0486g of trimesic aldehyde and 0.177g of ethidium bromide were put into a 100ml schlenk tube containing 10ml of a 1, 4-dioxane standard solution, mixed uniformly by ultrasonic oscillation, and 0.5ml of 3mol/L acetic acid was added as a catalyst to make the schlenk tube at 77k (N)2Liquid bath) and degassed by a freeze-pump-thaw cycle, followed by a schlenk tube negative pressure reaction at 120 ℃ for 3 days, and after the reaction was completed, the solid was collected at room temperature and washed three times with tetrahydrofuran, and dried under vacuum to obtain organic porous polymer 1 (P1).
Example 2
0.0714g of 3,4', 5-trioxane-1, 1-biphenyl and 0.177g of ethidium bromide were added to a 100ml schlenk tube containing 10ml of 1, 4-dioxane standard solution, mixed well by ultrasonic oscillation, and 0.5ml of 3mol/L acetic acid was added as a catalyst to make the schlenk tube at 77k (N)2Liquid bath) and degassing by freeze-pump-thaw cycle, followed by reaction of schlenk tube under negative pressure at 120 ℃ for 3 days, and the reaction was terminatedThereafter, the solid was collected at room temperature, washed three times with tetrahydrofuran, and dried in vacuo to obtain an organic porous polymer 2 (P2).
Example 3
0.117g of 1,3, 5-tris (p-formylphenyl) benzene and 0.177g of ethidium bromide were put into a 100ml schlenk tube containing 10ml of 1, 4-dioxane standard solution, mixed well by ultrasonic agitation, and 0.5ml of 3mol/L acetic acid was added as a catalyst to make the schlenk tube at 77k (N.sub.2Liquid bath) and degassed by a freeze-pump-thaw cycle, followed by a schlenk tube negative pressure reaction at 120 ℃ for 3 days, after which the solid was collected at room temperature and washed three times with tetrahydrofuran and dried under vacuum to give organic porous polymer 3 (P3).
Example 4
The polymer P10.07g obtained in example 1 was placed in a high-pressure reactor, 1ml of propylene oxide was added, the reactor was sealed, and 1MPa of CO was used at room temperature2The pressure of air in the replacement kettle is kept at 1MPa for six times, the reaction is carried out for 12 hours at the temperature of 90 ℃, and the catalyst and the product are separated by high-speed centrifugation after the reaction is finished. The conversion, determined by gas chromatography, was 85%.
Example 5
As in example 4, the catalyst used was catalyst P3 (0.06 g) from example 2, with a conversion of 41%.
Example 6
As in example 4, the catalyst used was catalyst P2 (0.06 g) from example 3, the conversion being 90%.
Example 7
Placing the polymer P30.07g obtained in example 3 into a high-pressure reaction kettle, adding 1ml of epoxy chloropropane, sealing the reaction kettle, and using 1.4MPa of CO at room temperature2The pressure of air in the replacement kettle is kept at 1.4MPa for six times, the reaction is carried out for 12 hours at the temperature of 100 ℃, and the catalyst and the product are separated by high-speed centrifugation after the reaction is finished. The conversion, determined by gas chromatography, was 99%.
Example 8
As in example 7, the epoxide used was bromopropylene oxide with a conversion of 99%.
Example 9
In the same way as in example 7, the epoxide used was phenyl glycidyl ether, the reaction time was 14h, the reaction temperature was 120 ℃ and the conversion was 93%.
Example 10
In the same way as in example 7, the epoxide used was cyclopentane epoxide, the reaction time was 14h, the reaction temperature was 120 ℃ and the conversion was 75%.
Example 11
In the same way as in example 7, the epoxide used was cyclohexene oxide, the reaction time was 14h, the reaction temperature was 120 ℃ and the conversion was 72%.
TABLE 1 catalysis of polymers for cycloaddition of epoxides with carbon dioxide to form cyclic carbonates
As can be seen from fig. 2, the polymer has good thermal stability and exhibits excellent performance in catalyzing carbon dioxide cycloaddition reactions.
The above description is only a preferred embodiment of the present invention, and all equivalent changes and modifications made in accordance with the claims of the present invention should be covered by the present invention.
Claims (10)
1. An organic porous polymer characterized by: the structural formula is as follows:
wherein R is aromatic aldehyde organic matter containing 1-10 benzene rings.
2. A method of preparing the organic porous polymer of claim 1, wherein: the method comprises the following steps:
(1) uniformly mixing an aromatic aldehyde compound, ethidium bromide and a reaction solvent;
(2) adding acetic acid, and reacting under the condition of heating and negative pressure;
(3) centrifuging at room temperature, washing, and vacuum drying to obtain the organic porous polymer.
3. The method of claim 2, wherein: the aromatic aldehyde compound is any one of trimesic aldehyde, 3,4', 5-trioxadecyl-1, 1-biphenyl, 1,3, 5-tri (p-formylphenyl) benzene and 1,3, 5-tri (4' -formyl [1,1' -biphenyl ] -4-yl) benzene.
4. The method of claim 2, wherein: the reaction solvent is any one of 1, 4-dioxane standard solution, N-dimethylformamide, 1, 2-dichlorobenzene standard solution, N-butanol, 1,3, 5-trimethylhexahydro-1, 3, 5-triazine and dimethyl sulfoxide.
5. The method of claim 2, wherein: the reaction temperature in the step (2) is 100-160 ℃, and the reaction time is 2-6 days.
6. The method of claim 2, wherein: the washing solvent in the step (3) is any one of tetrahydrofuran, methanol and ethyl acetate.
7. The method of claim 2, wherein: the molar ratio of the aromatic aldehyde compound to the ethidium bromide to the reaction solvent to the acetic acid is 1.9-2.2: 3: 0.5-0.1: 0.0008-0.001.
8. Use of an organic porous polymer according to claim 1 or prepared by the method according to claim 2 for catalyzing the cycloaddition reaction of an epoxide with carbon dioxide.
9. Use according to claim 8, characterized in that: the method comprises the following steps:
(1) adding organic porous polymer and epoxide into a high-pressure reaction kettle, sealing, and filling CO at room temperature2Removing air in the kettle for the third time;
(2) filling with CO2Until the pressure in the reaction kettle reaches 0.6-1.8MPa, and the reaction is carried out for 6-15 hours at 50-150 ℃;
(3) centrifugally separating the catalyst organic porous polymer and the reaction product cyclic carbonate.
10. The method of claim 9, wherein: the epoxide is any one of epoxypropane, epichlorohydrin, epibromohydrin, styrene oxide, phenyl glycidyl ether, cyclohexene oxide and cyclopentane epoxide.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114656607A (en) * | 2022-04-06 | 2022-06-24 | 青岛科技大学 | Imidazole ion porous organic polymer, preparation and CO catalysis2Application method for preparing cyclic carbonate by coupling with epoxide |
| CN115960326A (en) * | 2023-01-19 | 2023-04-14 | 大连理工大学 | For CO 2 Ionic covalent organic framework catalyst for preparing cyclic carbonate through cycloaddition, preparation method and application |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114656607A (en) * | 2022-04-06 | 2022-06-24 | 青岛科技大学 | Imidazole ion porous organic polymer, preparation and CO catalysis2Application method for preparing cyclic carbonate by coupling with epoxide |
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| CN115960326A (en) * | 2023-01-19 | 2023-04-14 | 大连理工大学 | For CO 2 Ionic covalent organic framework catalyst for preparing cyclic carbonate through cycloaddition, preparation method and application |
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