CN111215148B - ZIF @ TU-POP composite catalyst and preparation method and application thereof - Google Patents

ZIF @ TU-POP composite catalyst and preparation method and application thereof Download PDF

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CN111215148B
CN111215148B CN202010161548.XA CN202010161548A CN111215148B CN 111215148 B CN111215148 B CN 111215148B CN 202010161548 A CN202010161548 A CN 202010161548A CN 111215148 B CN111215148 B CN 111215148B
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韩正波
房挺
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    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
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Abstract

The invention belongs to the technical field of chemical catalytic materials, and particularly provides a ZIF @ TU-POP composite catalyst and a preparation method and application thereof. Adding urea, sodium sulfite solution and acetic acid into deionized water containing phenylenediamine, stirring for 24-36h at 90-120 ℃, filtering, washing, and vacuum drying to obtain 1, 3-bis (4-aminophenyl) urea; adding 1, 3-bis (4-aminophenyl) urea, cyanuric chloride and ZIF materials into dry dimethyl sulfoxide, reacting at 15-25 ℃, adding N, N-diisopropylethylamine, stirring, adding the crude product into ice to form a solid after the reaction is finished, filtering, and washing with dichloromethane, tetrahydrofuran and ethyl acetate in sequence to obtain the target product. The yield of cyclic carbonate generated by catalyzing epoxypropane and carbon dioxide by the ZIF @ TU-POP composite catalyst can reach 99% at most, and the conversion rate can still reach more than 90% after the cyclic carbonate is repeatedly utilized for 4 times.

Description

ZIF @ TU-POP composite catalyst and preparation method and application thereof
Technical Field
The invention relates to a ZIF @ TU-POP composite catalyst and a preparation method and application thereof, belonging to the technical field of chemical catalytic materials.
Background
For a long time, fossil fuel combustion produces CO2Emissions are increasing and widely recognized as a major cause of global climate change and related environmental problems. Carbon capture and separation of CO in flue gas after combustion2Is to reduce industrial CO2Discharge and obtain CO to atmosphere2A feasible method of control of the concentration. And cyclic carbonate is widely used in carbonate polycarbonate as an important organic solventThe production of the compound, aprotic polar solvent, medicine, intermediate of fine chemical engineering, petroleum additive and the like are important chemical raw materials. Thus CO is converted into2The conversion into cyclic carbonate has better economic benefits. The preparation method of the prior cyclic carbonate mainly comprises the following steps: phosgene process, direct olefin oxycarbonylation from CO2Cycloaddition of an epoxide. The virulent phosgene used in the phosgene method is basically eliminated at present; cyclic carbonates can be prepared in one step from olefins by direct oxidative carbonylation of olefins, however, the addition of noble metal oxidation catalysts is required, increasing costs.
Zeolitic Imidazole Framework (ZIFs) materials can be designed and tailored for specific functions in their structure and topology due to the abundance of metal node and ligand geometries and connectivity. High specific surface area and pore volume, easily adjustable pore diameter, for CO2For high capture and absorption, can be used as capture fixed CO2A catalyst for conversion to cyclic carbonates. POPs are a class of porous materials formed by joining together purely organic monomers (usually aromatic or conjugated) through strong covalent bonds. The various synthetic possibilities of POPs allow precise control of their nanopore structure and surface chemistry at the molecular level, aiming at increasing CO by thermodynamic effects2Adsorption capacity and selectivity to other gases. Therefore, the ZIF and POP are combined together through reasonable regulation to form a ZIF @ POP material so as to catalyze the conversion of the cyclic carbonate.
Disclosure of Invention
The invention aims to solve the problems that a precious metal catalyst is expensive, the catalyst is easy to poison and secondary pollution is easy to cause in the existing catalytic process, and the like.
In order to achieve the purpose, the invention adopts the technical scheme that: a preparation method of a ZIF @ TU-POP composite catalyst comprises the following steps:
1) adding urea, sodium sulfite solution and acetic acid into deionized water containing phenylenediamine, stirring for 24-36h at 90-120 ℃, filtering, washing with hot water, and vacuum drying to obtain 1, 3-bis (4-aminophenyl) urea;
2) adding 1, 3-bis (4-aminophenyl) urea, cyanuric chloride and ZIF shell materials into dry dimethyl sulfoxide for reaction, adding N, N-diisopropylethylamine, stirring for 24-36 hours, adding the crude product into ice to form a solid after the reaction is finished, filtering, and washing with dichloromethane, tetrahydrofuran and ethyl acetate in sequence to obtain the target product.
Preferably, in the ZIF @ TU-POP composite catalyst, in the step 1), the phenylenediamine is any one of o-phenylenediamine, m-phenylenediamine and p-phenylenediamine.
Preferably, in the above ZIF @ TU-POP composite catalyst, in step 1), the molar ratio of urea: 1-phenylenediamine: 0.8-1.
Preferably, in the above ZIF @ TU-POP composite catalyst, in the step 2), the molar ratio of 1, 3-bis (4-aminophenyl) urea: cyanuric chloride: ZIF housing material ═ 1: 0.66-0.7: 0.4-0.5.
Preferably, in the ZIF @ TU-POP composite catalyst, in the step 2), the N, N-diisopropylethylamine is added dropwise.
Preferably, in the step 2), the preparation method of the ZIF @ TU-POP composite catalyst comprises the following steps: zn (NO)3)2·6H2O or Co (NO)3)2·6H2Dissolving O in methanol to obtain a solution A, dissolving 2-methylimidazole in methanol to obtain a solution B, mixing the solution A and the solution B, stirring for 24 hours, filtering, washing with methanol, and drying in vacuum to obtain the ZIF shell material.
Preferably, in the step 2), the reaction temperature is 15-25 ℃, and the reaction time is 24-36 h.
The ZIF @ TU-POP composite catalyst is applied to catalytic synthesis of cyclic carbonate.
Preferably, the above application, method is as follows: adding the propylene oxide and the ZIF @ TU-POP composite catalyst into a high-pressure reaction kettle at 1MPa and CO2Reacting for 12-24h at 80 ℃ in atmosphere.
Preferably, in the above application, the ZIF @ TU-POP composite catalyst is added in an amount of 0.06g/g propylene oxide.
The invention has the beneficial effects that:
(1) the preparation method is simple, the raw materials are easy to obtain, and the price is low;
(2) the ZIF material is adopted as a carrier, so that the catalytic activity is improved, and the ZIF material is not easy to leach;
(3) easy to recycle, can effectively reduce secondary pollution and improve the reusability of the catalyst.
Drawings
FIG. 1 is a FT-IR plot of the ZIF @ TU-POP composite catalyst prepared in example 2.
FIG. 2 is an XRD pattern of the ZIF @ TU-POP composite catalyst prepared in example 2.
FIG. 3 is an adsorption profile of the ZIF @ TU-POP composite catalyst prepared in example 2.
FIG. 4 is a scanning electron micrograph of the ZIF @ TU-POP composite prepared in example 4.
FIG. 5 is a graph of the cycle experimental yield of the ZIF @ TU-POP composite catalyst prepared in example 5.
Detailed Description
The present invention will be described in detail below with reference to specific examples, but the present invention is not limited to the following examples, and various modifications and implementations are included within the technical scope of the present invention without departing from the content and scope of the present invention.
EXAMPLE 1 preparation of ZIF housing Material
Preparation of ZIF-8: adding Zn (NO)3)2·6H2Dissolving O1.68 g in 80ml of methanol to obtain solution A, dissolving 2-methylimidazole 3.7g in 80ml of methanol to obtain solution B, mixing solution A and solution B, stirring for 24h, filtering, washing with methanol, and vacuum drying at 60 ℃ for 12h to obtain ZIF-8.
Preparation of ZIF-67: mixing Co (NO)3)2·6H2O1.69 g was dissolved in 80ml of methanolDissolving 3.7g of 2-methylimidazole in 80ml of methanol to obtain a solution B, mixing and stirring the solution A and the solution B for 24 hours, filtering, and drying in vacuum to obtain ZIF-67.
Example 2 ZIF-8@ TU-POP composite catalyst
1. Synthetic route of ZIF-8@ TU-POP composite catalyst
Figure BDA0002405975550000031
2. Preparation of ZIF-8@ TU-POP composite catalyst
Urea 3g, 2ml of a 39% sodium hydrogen sulfite solution and 2ml of acetic acid were added to 50ml of deionized water containing 4g of p-phenylenediamine, and the mixture was stirred at 90 ℃ for 24 hours, followed by filtration and washing with a large amount of hot water, followed by vacuum drying to obtain the product 1, 3-bis (4-aminophenyl) urea. 1g of 1, 3-bis (4-aminophenyl) urea, 1.5g of cyanuric chloride and 500mg of ZIF-8 are added into 10ml of dry dimethyl sulfoxide, the reaction temperature is kept at 15 ℃, 2ml of N, N-diisopropylethylamine is added dropwise, stirring is carried out for 24 hours, after the reaction is finished, a crude product is added into ice to form a solid, and then the solid is filtered and washed by dichloromethane, tetrahydrofuran and ethyl acetate in sequence to obtain the ZIF-8@ TU-POP composite catalyst. And FT-IR (FIG. 1), XRD (FIG. 2), N were applied to the catalyst2Adsorption test (fig. 3). The FT-IR chart shows that-NH-peak, triazine peak and imidazole ring characteristic peak exist, the XRD chart shows that Bragg diffraction peak of composite material XRD is consistent with diffraction peak of ZIF-8, so that successful compounding can be shown, and N is tested2The adsorption performance can show that the composite material has a large amount of micropore structures and a small amount of mesoporous structures.
3. Application of ZIF-8@ TU-POP composite catalyst in catalytic synthesis of cyclic carbonate
Adding 1.2ml of epoxypropane and 60mg of ZIF-8@ TU-POP composite catalyst into a high-pressure reaction kettle, and reacting at 1MPa for CO2The reaction was carried out at 80 ℃ for 12 hours and the yield of cyclic carbonate was determined by GC after the end of the reaction. The yield of the propylene carbonate can reach 95% in 12 hours, and the conversion rate can still reach 94% when the propylene carbonate is repeatedly used for 4 times.
The synthetic route of the cyclic carbonate synthesized by catalyzing propylene oxide and carbon dioxide by ZIF-8@ TU-POP is as follows:
Figure BDA0002405975550000041
example 3 ZIF-67@ TU-POP composite catalyst
1. Synthetic route of ZIF-67@ TU-POP composite catalyst
Figure BDA0002405975550000042
2. Preparation of ZIF-67@ TU-POP composite catalyst
Urea 3g, 39% sodium bisulfite solution 2ml and acetic acid 2ml were added to 50ml deionized water containing 4g p-phenylenediamine and the mixture was stirred at 90 ℃ for 24h, then filtered and washed with copious amounts of hot water and dried under vacuum to give the product 1, 3-bis (4-aminophenyl) urea. 1g of 1, 3-bis (4-aminophenyl) urea, 1.4g of cyanuric chloride and 400mg of ZIF-67 are added into 10ml of dry dimethyl sulfoxide, the reaction temperature is kept at 15 ℃, 2ml of N, N-diisopropylethylamine is added dropwise, stirring is carried out for 24 hours, after the reaction is finished, a solid is formed by adding a crude product into ice, and then the solid is filtered and washed by dichloromethane, tetrahydrofuran and ethyl acetate sequentially to obtain the ZIF-67@ TU-POP composite material catalyst.
3. Application of ZIF-67@ TU-POP composite catalyst in catalytic synthesis of cyclic carbonate
Adding 1.2ml of epoxypropane and 60mg of ZIF-67@ TU-POP composite catalyst into a high-pressure reaction kettle, and reacting at 1MPa for CO2The reaction is carried out for 12 hours at the temperature of 80 ℃, and the ZIF-67@ TU-POP composite catalyst is tested and analyzed by a cyclic carbonate synthesis catalytic experiment, so that the yield of the propylene carbonate can reach 98% in 12 hours, and the conversion rate can still reach 94% when the propylene carbonate is repeatedly used for 4 times.
Example 4 ZIF-8@ TU-POP-m composite catalyst
1. Synthetic route of ZIF-8@ TU-POP-m composite catalyst
Figure BDA0002405975550000051
2. Preparation of ZIF-8@ TU-POP-m composite catalyst
Urea 3g, a 39% sodium hydrogen sulfite solution 2ml and acetic acid 2ml were added to 50ml of deionized water containing 4g of m-phenylenediamine, and the mixture was stirred at 90 ℃ for 24 hours, followed by filtration and washing with a large amount of hot water, followed by vacuum drying to obtain 1, 3-bis (4-aminophenyl) urea as a product. Adding 1g of 1, 3-bis (4-aminophenyl) urea and 2g of cyanuric chloride 400mgZIF-8 into 10ml of dry dimethyl sulfoxide, keeping the reaction temperature at 15 ℃, dropwise adding 2ml of N, N-diisopropylethylamine, stirring for 24 hours, after the reaction is finished, adding a crude product into ice to form a solid, filtering the solid, washing the solid with dichloromethane, tetrahydrofuran and ethyl acetate in sequence to obtain the ZIF @ TU-POP-m composite material catalyst, and performing SEM (figure 4) test on the catalyst, wherein the appearance is shown in the figure and shows that the composite material is completely compounded.
3. Application of ZIF-8@ TU-POP-m composite catalyst in catalytic synthesis of cyclic carbonate
Adding 1.2ml of epoxypropane and 60mg of ZIF-8@ TU-POP-m composite catalyst into a high-pressure reaction kettle, and reacting at 1MPa for CO2The reaction was carried out at 80 ℃ for 12 hours and the yield of cyclic carbonate was determined by GC after the end of the reaction. The yield of the propylene carbonate can reach 94% in 12h, and the conversion rate can still reach 95% when the propylene carbonate is repeatedly used for 4 times.
Example 5 ZIF-67@ TU-POP-o hybrid catalyst
1. Synthetic route of ZIF-67@ TU-POP-o composite catalyst
Figure BDA0002405975550000052
2. Preparation of ZIF-67@ TU-POP-o composite catalyst
Urea 3g, 2ml of a 39% sodium hydrogen sulfite solution and 2ml of acetic acid were added to 50ml of deionized water containing 4g of o-phenylenediamine, and the mixture was stirred at 90 ℃ for 24 hours, followed by filtration and washing with a large amount of hot water, followed by vacuum drying to obtain the product 1, 3-bis (4-aminophenyl) urea. Adding 1.8g of 1, 3-bis (4-aminophenyl) urea and 2g of cyanuric chloride 400mgZIF-67 into 10ml of dry dimethyl sulfoxide, keeping the reaction temperature at 15 ℃, dropwise adding 2ml of N, N-diisopropylethylamine, stirring for 24 hours, adding the crude product into ice to form a solid after the reaction is finished, filtering the solid, and washing the solid with dichloromethane, tetrahydrofuran and ethyl acetate in sequence to obtain the ZIF-67@ TU-POP-o composite catalyst.
3. Application of ZIF-67@ TU-POP-o composite catalyst in catalytic synthesis of cyclic carbonate
Adding 1.2ml of epoxypropane and 60mg of ZIF-67@ TU-POP-o composite catalyst into a high-pressure reaction kettle, and reacting at 1MPa for CO2The reaction is carried out for 12 hours at the temperature of 80 ℃, the ZIF-67@ TU-POP-o composite catalyst is subjected to cyclic carbonate synthesis catalytic experiment test analysis, the yield of propylene carbonate can reach 99% in 12 hours, the conversion rate can still reach 95% when the catalyst is repeatedly utilized for 4 times, XRD (X-ray diffraction) test is carried out on the circulated catalyst (figure 5), and the Bragg diffraction peak of the catalyzed catalyst and the Bragg diffraction peak before catalysis are not obviously changed can be seen from an XRD (X-ray diffraction) diagram.

Claims (9)

1. A ZIF @ TU-POP composite catalyst is characterized in that the preparation method comprises the following steps:
1) adding urea, sodium sulfite solution and acetic acid into deionized water containing p-phenylenediamine, stirring for 24-36h at 90-120 ℃, filtering, washing with hot water, and vacuum drying to obtain 1, 3-bis (4-aminophenyl) urea;
2) adding 1, 3-bis (4-aminophenyl) urea, cyanuric chloride and ZIF shell materials into dry dimethyl sulfoxide for reaction, adding N, N-diisopropylethylamine, stirring for 24-36 hours, adding the crude product into ice to form a solid after the reaction is finished, filtering, and washing with dichloromethane, tetrahydrofuran and ethyl acetate in sequence to obtain the target product.
2. The ZIF @ TU-POP composite catalyst as claimed in claim 1, wherein in the step 1), the molar ratio of urea: p-phenylenediamine = 1: 0.8-1.
3. The ZIF @ TU-POP composite catalyst as claimed in claim 1, wherein N, N-diisopropylethylamine is added dropwise in the step 2).
4. The ZIF @ TU-POP composite catalyst as claimed in claim 1, wherein, in the step 2), the molar ratio of 1, 3-bis (4-aminophenyl) urea: cyanuric chloride: ZIF housing material = 1: 0.66-0.7: 0.4-0.5.
5. The ZIF @ TU-POP composite catalyst as claimed in claim 1, wherein, in the step 2), the preparation method of the ZIF shell material comprises the following steps: adding Zn (NO)3)2·6H2O or Co (NO)3)2·6H2Dissolving O in methanol to obtain a solution A, dissolving 2-methylimidazole in methanol to obtain a solution B, mixing the solution A and the solution B, stirring for 24 hours, filtering, washing with methanol, and drying in vacuum to obtain the ZIF shell material.
6. The ZIF @ TU-POP composite catalyst as claimed in claim 1, wherein the reaction temperature in step 2) is 15-25 ℃ and the reaction time is 24-36 h.
7. The use of the ZIF @ TU-POP composite catalyst of claim 1 in the catalytic synthesis of cyclic carbonates.
8. Use according to claim 7, characterized in that the method is as follows: adding the propylene oxide and the ZIF @ TU-POP composite catalyst into a high-pressure reaction kettle at 1MPa and CO2Reacting for 12-24h at 80 ℃ under the atmosphere.
9. The use of claim 7, wherein the amount of ZIF @ TU-POP composite catalyst added is 0.06g/g propylene oxide.
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