CN116925321A - Preparation method and application of metal-free organic polymer catalyst - Google Patents

Preparation method and application of metal-free organic polymer catalyst Download PDF

Info

Publication number
CN116925321A
CN116925321A CN202310722211.5A CN202310722211A CN116925321A CN 116925321 A CN116925321 A CN 116925321A CN 202310722211 A CN202310722211 A CN 202310722211A CN 116925321 A CN116925321 A CN 116925321A
Authority
CN
China
Prior art keywords
metal
organic polymer
polymer catalyst
free organic
triazine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN202310722211.5A
Other languages
Chinese (zh)
Inventor
陕绍云
施兰
刘毅
胡天丁
李双江
姚凯利
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kunming University of Science and Technology
Original Assignee
Kunming University of Science and Technology
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Kunming University of Science and Technology filed Critical Kunming University of Science and Technology
Priority to CN202310722211.5A priority Critical patent/CN116925321A/en
Publication of CN116925321A publication Critical patent/CN116925321A/en
Pending legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—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
    • 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
    • C07D317/34—Oxygen atoms
    • C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
    • C08G18/3842—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
    • C08G18/3851—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing three nitrogen atoms in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Catalysts (AREA)

Abstract

The invention discloses a preparation method of a metal-free organic polymer catalyst, which takes isocyanate and triazine nitrogen-containing heterocyclic organic matters as raw materials, and after reflux reaction for 12-36 hours under the conditions of existence of solvent, nitrogen atmosphere and 80-120 ℃, reaction products are cooled to room temperature, solid-liquid separation, solid washing and drying are carried out, thus obtaining the metal-free organic polymer catalyst 2 The method disclosed by the invention is simple and easy to operate, and is suitable for industrial production and market popularization and application.

Description

Preparation method and application of metal-free organic polymer catalyst
Technical Field
The invention relates to a preparation method of a metal-free organic polymer catalyst and a catalyst for catalyzing CO 2 The application of the catalyst in the conversion into cyclic carbonate belongs to the field of material chemical industry.
Background
With the rapid development of industry, the concentration of carbon dioxide in the atmosphere is rapidly increased, and a plurality of environmental problems such as seawater acidification, climate warming and the like are brought. In addition, CO 2 Is also a C1 resource which has rich reserves, low cost, no toxicity and reproducibility. Realization of CO 2 The emission reduction and the resource utilization are significant for improving the ecological environment. CO 2 Cycloaddition with epoxy compounds not only has 100% atomic efficiency, but also can synthesize high-value cyclic carbonates which are widely used in the fields of batteries, solvents, polyesters, organic synthesis, etc., however, due to CO 2 The inherent thermodynamic stability and kinetic inertness require the development of green, highly efficient catalysts.
Many applications for CO have been reported 2 And cycloaddition reaction catalysts of epoxy compounds, including metal complexes, metal oxides, organic bases, carbon materials, ionic liquids, organic polymers, metal Organic Frameworks (MOFs), covalent Organic Frameworks (COFs), and the like. The catalysts described above show good catalytic properties, but all suffer from certain drawbacks. For example, homogeneous catalysts such as metal complexes, ionic liquids, organic bases, etc. have excellent catalytic activity, but have problems of difficult separation and environmental pollution. Early heterogeneous catalysts such as metal oxides and carbon materials were poorly active and high temperatures and pressures were typically required to catalyze the reaction. In recent years, organic framework materials such as MOFs and COFs are continuously emerging, and the problems of high cost, complex preparation and the like are plagued by people although the catalytic effect is good. In addition, metal-containing catalysts may leach out metal residues from the product, while halogen-containing catalysts, including cocatalysts, may not only corrode equipment, but also cause environmental pollution. Therefore, it is necessary to develop a heterogeneous catalyst which is free of metals, halogen, simple to prepare and has high catalytic activity.
Disclosure of Invention
The invention is thatThe preparation method of the metal-free organic polymer catalyst comprises the steps of taking isocyanate and triazine nitrogen-containing heterocyclic organic matters as raw materials, carrying out reflux reaction for 12-36h in the presence of a solvent and under the atmosphere of nitrogen at 80-120 ℃, cooling a reaction product to room temperature, carrying out solid-liquid separation, and washing and drying solids to obtain the metal-free organic polymer catalyst; the invention prepares the catalyst by a one-step method, and the catalyst prepares CO under the condition of no cocatalyst and solvent 2 The catalyst is converted into cyclic carbonate with epoxide, and has the advantages of obvious catalytic effect, high selectivity, mild reaction condition and recycling for a plurality of times; the catalyst accords with the concept of economy, green and sustainable and is used in CO 2 The method has unique advantages in the aspects of conversion, emission reduction and the like.
The isocyanate is one of p-phenylene diisocyanate, 1, 3-phenylene diisocyanate, toluene-2, 3-diisocyanate and triphenylmethane triisocyanate.
The triazine nitrogen-containing heterocyclic organic matter is one of melamine, 2,4, 6-tri (4-aminophenyl) -1,3, 5-triazine, 2,4, 6-tri (4-aminophenoxy) -1,3, 5-triazine, 2, 6-trihydrazino-1, 3, 5-triazine and triphenylmethane triisocyanate.
The solvent is one or more of dimethyl sulfoxide (DMSO), N-dimethylacetamide, ethylene glycol, methanol, N-dimethylformamide, 1, 4-dioxane and acetic acid.
The molar ratio of the isocyanate to the triazine nitrogen-containing heterocyclic organic matter is 3:1-3.
The catalyst prepared by the method is applied to the synthesis of the cyclic carbonate; specifically, adding a catalyst and epoxide into a high-pressure reaction kettle according to the mol ratio of 1:100-1000, and carrying out CO (carbon monoxide) 2 The autoclave was subjected to 3 times of CO at room temperature before cycloaddition 2 Purging to remove impurities and then adjusting the initial CO 2 Pressure (0.1-1.5 MPa), reacting at 80-120deg.C for 2-10 hr, cooling the autoclave to below 10deg.C with ice bath, slowly releasing residual gas, filtering, collecting catalyst and reaction product, and collecting epoxyThe chemical compound is one of propylene oxide, epichlorohydrin, styrene oxide, cyclohexane oxide and ethylene oxide.
Characterization of the resulting catalyst by Fourier transform Infrared Spectroscopy (FT-IR), finding the formation of-NH-bonds and the corresponding positions-NH in the catalyst 2 And the disappearance of the n=c=o bond, proving that the catalyst has been successfully prepared; nuclear magnetic resonance hydrogen spectrum [ ] 1 H-NMR) also further demonstrates that the catalyst can successfully catalyze CO 2 With epoxides to give cyclic carbonate products.
Compared with the prior art, the invention has the following advantages:
(1) The catalyst is prepared by adopting an environment-friendly and low-cost one-step method with isocyanate and triazine nitrogen-containing heterocyclic organic matters as precursors;
(2) The catalyst is used in CO under the conditions of no cocatalyst and no solvent 2 The catalyst has remarkable catalytic effect, high selectivity, mild reaction condition and recycling for many times in the reaction of converting epoxide into cyclic carbonate, has good structural stability and recoverability, and is easy to separate from products; in addition, the catalyst also has higher catalytic activity on a series of epoxy compounds;
(3) Non-metal, halogen-free heterogeneous catalyst capable of effectively converting CO 2 The design idea of the catalyst is that the secondary pollution caused by participation of transition metal and corrosion of reaction equipment caused by a halogen-containing cocatalyst are avoided;
the catalyst of the invention accords with the concept of economic and green sustainable development and is prepared in CO 2 The method has the advantages of simplicity and easiness in operation, and is suitable for industrial production and market popularization and application.
Drawings
FIG. 1 is a Fourier transform infrared spectrum (FT-IR) diagram of the organic polymer catalyst prepared in example 1; wherein Melamine is Melamine, 1,4-Phenylene diisocyanate is 1, 4-benzene diisocyanate, and UM-OP is a metal-free organic polymer catalyst;
FIG. 2 is a schematic illustration of the application of the organic polymer catalyst prepared in example 1 to the catalysis of epoxyChloropropane and CO 2 Nuclear magnetic resonance hydrogen spectrum of the obtained cyclic carbonate 1 H-NMR) chart.
Detailed Description
The invention is further described below with reference to examples and figures, but is not limited in any way, and any alterations or substitutions based on the teachings of the invention are within the scope of the invention.
Example 1
(1) A three-necked flask with a stirrer and a condenser was filled with melamine (1.01 g,8 mmol), 1, 4-benzene diisocyanate (1.92 g,12 mmol) and 50mL of DMSO as solvents in this order, and then refluxed for 24 hours at 100℃under a nitrogen atmosphere;
(2) After the reaction is finished, cooling the reaction product to room temperature, filtering, alternately washing the solid with deionized water and acetone, and finally vacuum drying at 60 ℃ to obtain a melamine polymer UM-OP; the catalyst obtained was characterized by Fourier transform infrared (FT-IR) and the results are shown in FIG. 1, which shows 3418cm from the FT-IR spectrum -1 And 3470cm -1 The characteristic absorption peak at the site is attributed to-NH in melamine 2 Is free of-NH-in UM-OP 2 And the triazine ring has a characteristic absorption peak of 1552cm -1 Where, description is given of melamine-NH 2 Takes part in the polymerization reaction, and the triazine ring is reserved; at 2270cm -1 The absorption peak at this point is due to the stretching vibration of-n=c=o in 1,4-phenyl diisocyanate, the characteristic absorption peak of-n=c=o in UM-OP disappears, and the stretching vibration peak of c=o is 1635cm -1 This indicates that the reaction was successful and that the result indicated that the metal-free organic polymer catalyst had been successfully prepared;
(3) Application of the catalyst to the catalysis of CO 2 And epoxy compound to synthesize cyclic carbonate, adding melamine polymer (UM-OP) 0.0458g and epoxy chloropropane 2mL into a high-pressure reactor, and introducing pure CO 2 After 3 times of air in the kettle is replaced, CO is introduced 2 After the pressure in the kettle reaches 1.0MPa, the air inlet and outlet valves are closed, the reaction is carried out for 8 hours at 120 ℃, and after the reaction is finished, ice is usedThe bath is used for reducing the temperature of the autoclave to 5 ℃ and slowly releasing residual gas, finally, the reaction product is filtered, and the liquid is collected to obtain the product of the cyclopropylchloro-propylene carbonate, and the nuclear magnetic resonance hydrogen spectrum of the product is [ 1 H-NMR) is shown in fig. 2, from which it can be seen that the chemical shifts of the cyclopropylchloro carbonate are δ=5.06 ppm,4.63ppm,4.43ppm,3.87ppm,3.75ppm, respectively, from which CO is determined 2 Cycloaddition reaction with epoxy chloropropane to generate the cyclic chloropropene carbonate, and calculating the yield and selectivity of the cyclic chloropropene carbonate (CPC) through integration, wherein the yield is 97 percent, and the selectivity is 99 percent;
the filtered filter residue is used as a catalyst, the catalyst is washed by methanol for 4 times, and then is dried in a vacuum oven at 60 ℃ for 8 hours and is reused for CO 2 Cycloaddition reaction with epichlorohydrin to synthesize cyclic carbonate under the same conditions as above 1 The yield of the cyclic chloropropene carbonate is 97% by H-NMR measurement, the catalyst is recycled for the second time, and the yield of the cyclic chloropropene carbonate is 93%; the catalyst is recycled for the third time, and the yield of the cyclopropene carbonate is 92%; the catalyst is recycled for the fourth time, and the yield of the cyclopropenyl carbonate is 90%; the catalyst is recycled for the fifth time, and the yield of the cyclopropenyl carbonate is 87%; the catalyst is recycled for the sixth time, and the yield of the cyclopropenyl carbonate is 83%.
Example 2
(1) A three-neck flask with a stirrer and a condenser is filled with melamine (1.01 g,8 mmol), toluene-2, 5-diisocyanate (2.09 g,12 mmol) and 50mL DMSO as solvents in sequence, and reflux reaction is carried out for 24h under nitrogen atmosphere at 100 ℃;
(2) After the reaction is finished, cooling to room temperature, filtering, alternately washing the solid with deionized water and acetone, and vacuum drying the solid at 60 ℃ to obtain a melamine polymer UM-OP-1, and characterizing the product by using Fourier transform infrared spectroscopy (FT-IR), wherein the result shows that the metal-free organic polymer catalyst has been successfully prepared;
(3) 0.0458g of melamine polymer (UM-OP-1) and 2mL of epichlorohydrin are added into a high-pressure reaction kettle in sequence, and pure CO is introduced 2 3 times of air in the kettle is replaced, and CO is introduced 2 So that the pressure in the kettle reaches 1.0MPaClosing an air inlet and outlet valve, reacting for 8 hours at 120 ℃, after the reaction is finished, reducing the temperature of the autoclave to 8 ℃ by using an ice bath, slowly releasing residual gas, filtering, and collecting liquid, namely the product of the cyclopropenyl carbonate, wherein the yield of the cyclopropenyl carbonate is 93%, and the selectivity is 99%;
example 3
(1) A three-neck flask with a stirrer and a condenser is filled with melamine (1.01 g,8 mmol), 1, 3-benzene diisocyanate (1.92 g,12 mmol) and 50mL of N, N-dimethylformamide which are taken as solvents in sequence, and reflux reaction is carried out for 24 hours at 100 ℃ under nitrogen atmosphere;
(2) After the reaction is finished, cooling to room temperature, filtering, alternately washing the solid with deionized water and acetone, and vacuum drying the solid at 60 ℃ to obtain a melamine polymer UM-OP-2;
(3) 0.0485g of melamine polymer (UM-OP-2) and 2mL of epichlorohydrin are added into a high-pressure reaction kettle in sequence, and pure CO is introduced 2 Replacing the air in the kettle for 3 times, and introducing CO again 2 After the pressure in the autoclave reaches 1.0MPa, the gas inlet and outlet valves are closed, the reaction is carried out for 8 hours at 120 ℃, after the reaction is finished, the temperature of the autoclave is reduced to 6 ℃ by using an ice bath, residual gas is slowly released, finally, the reaction product is filtered, the collected liquid is the cyclic carbonate product, the yield of the cyclic chloropropene carbonate is 95%, and the selectivity is 99%.
Example 4
(1) A three-neck flask with a stirrer and a condenser is filled with melamine (1.01 g,8 mmol), triphenylmethane triisocyanate (4.41 g,12 mmol) and 50mL of N, N-dimethylacetamide as solvents in sequence, and reflux reaction is carried out for 24 hours at 100 ℃ under nitrogen atmosphere;
(2) After the reaction is finished, cooling to room temperature, filtering, alternately washing the solid with deionized water and acetone, and vacuum drying the solid at 60 ℃ to obtain a melamine polymer UM-OP-3;
(3) 0.0846g of melamine polymer (UM-OP-3) and 2mL of epichlorohydrin are added into a high-pressure reaction kettle in sequence, and pure CO is introduced 2 Replacing the air in the kettle for 3 times, and introducing CO again 2 After the pressure in the kettle reaches 1.0MPa, the kettle is closedAnd (3) an air outlet valve, wherein the reaction is carried out for 8 hours at 120 ℃, after the reaction is finished, the temperature of the autoclave is reduced to below 10 ℃ by using an ice bath, residual gas is slowly released, finally, the reaction product is filtered, and liquid is collected, so that the cyclic carbonate product is obtained, the yield of the cyclic chloropropene carbonate is 87%, and the selectivity is 99%.
Example 5
(1) 2,4, 6-tris (4-aminophenyl) -1,3, 5-triazine (2.84 g,8 mmol), 1, 4-benzene diisocyanate (1.92 g,12 mmol) and 50mL DMSO were sequentially put into a 250mL three-neck flask with a stirrer and a condenser, and reflux reaction was carried out at 100℃under nitrogen atmosphere for 24 hours;
(2) After the reaction is finished, cooling to room temperature, filtering, alternately washing the solid with deionized water and acetone, and vacuum drying the solid at 60 ℃ to obtain a melamine polymer UM-OP-4;
(3) 0.0743g of melamine polymer UM-OP-4 and 2mL of epichlorohydrin are sequentially added into a high-pressure reaction kettle, and pure CO is introduced 2 Replacing the air in the kettle for 3 times, and introducing CO again 2 After the pressure in the autoclave reaches 1.0MPa, the gas inlet and outlet valve is closed, the reaction is carried out at the temperature of 120 ℃ for 8h, after the reaction is finished, the temperature of the autoclave is reduced to 3 ℃ by using an ice bath, residual gas is slowly released, finally, the reaction product is filtered, and liquid is collected, so that the cyclic carbonate product is obtained, the yield of the cyclic chloropropene carbonate is 90%, and the selectivity is 99%.

Claims (6)

1. A preparation method of a metal-free organic polymer catalyst is characterized in that: the preparation method comprises the steps of taking isocyanate and triazine nitrogen-containing heterocyclic organic matters as raw materials, carrying out reflux reaction for 12-36h in the presence of a solvent and under the atmosphere of nitrogen at 80-120 ℃, cooling the reaction product to room temperature, carrying out solid-liquid separation, and washing and drying the solid to obtain the metal-free organic polymer catalyst.
2. The method for preparing a metal-free organic polymer catalyst according to claim 1, wherein: the isocyanate is one of terephthalyl diisocyanate, 1,4-phenylene diisocyanate, toluene-2, 3-diisocyanate and triphenylmethane triisocyanate.
3. The method for preparing a metal-free organic polymer catalyst according to claim 1, wherein: the triazine nitrogen-containing heterocyclic organic matter is one of melamine, 2,4, 6-tri (4-aminophenyl) -1,3, 5-triazine, 2,4, 6-tri (4-aminophenoxy) -1,3, 5-triazine, 2, 6-trihydrazino-1, 3, 5-triazine and triphenylmethane triisocyanate.
4. The method for preparing a metal-free organic polymer catalyst according to claim 1, wherein: the solvent is one or more of dimethyl sulfoxide, N-dimethylacetamide, ethylene glycol, methanol, dimethylformamide, 1, 4-dioxane and acetic acid.
5. The method for preparing a metal-free organic polymer catalyst according to claim 1, wherein: the molar ratio of the isocyanate to the triazine nitrogen-containing heterocyclic organic matter is 3:1-3.
6. The metal-free organic polymer catalyst prepared by the method for preparing metal-free organic polymer catalyst according to any one of claims 1 to 5, which catalyzes CO 2 And the application of epoxide cycloaddition reaction in synthesizing cyclic carbonate.
CN202310722211.5A 2023-06-19 2023-06-19 Preparation method and application of metal-free organic polymer catalyst Pending CN116925321A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202310722211.5A CN116925321A (en) 2023-06-19 2023-06-19 Preparation method and application of metal-free organic polymer catalyst

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202310722211.5A CN116925321A (en) 2023-06-19 2023-06-19 Preparation method and application of metal-free organic polymer catalyst

Publications (1)

Publication Number Publication Date
CN116925321A true CN116925321A (en) 2023-10-24

Family

ID=88379659

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202310722211.5A Pending CN116925321A (en) 2023-06-19 2023-06-19 Preparation method and application of metal-free organic polymer catalyst

Country Status (1)

Country Link
CN (1) CN116925321A (en)

Similar Documents

Publication Publication Date Title
Yue et al. Synthesis of cyclic carbonate from CO2 and epoxide using bifunctional imidazolium ionic liquid under mild conditions
CN114656607B (en) Imidazole ion porous organic polymer, preparation and CO catalysis 2 Application method for preparing cyclic carbonate by coupling epoxide
CN114437363B (en) Squaramide derivative group covalent triazine skeleton polymer and application thereof in preparation of cyclic carbonate by catalyzing coupling of carbon dioxide and epoxide
CN111909094A (en) Multi-active center ionic liquid, preparation method and method for catalytically synthesizing cyclic carbonate by using multi-active center ionic liquid
CN116925321A (en) Preparation method and application of metal-free organic polymer catalyst
CN113117745B (en) Preparation method and application of metal-free catalyst
Obeso et al. Gas-phase organometallic catalysis in MFM-300 (Sc) provided by switchable dynamic metal sites
CN112851924B (en) Recyclable nitrogen-containing polycarbonate plastic synthesis method
CN112206808B (en) Catalyst for synthesizing isobutyl isobutyrate and preparation method and application thereof
CN112371150B (en) Nickel-aluminum bimetal nitrogen-carbon doped catalyst, preparation method thereof and application thereof in catalyzing levulinic acid hydrogenation to prepare gamma-valerolactone
CN111574378B (en) Method for efficiently synthesizing dihydroxy ethyl terephthalate without catalysis
Molla et al. Polymer supported rhodium carbonyl complex catalyzed carbonylation of glycerol for the synthesis of carboxylic acids
CN113214077A (en) Method for degrading thermoplastic polyethylene terephthalate
CN112246284B (en) Single-molecule load type metal-organic framework material, preparation method thereof and application thereof in catalytic conversion of carbon dioxide
CN108299240B (en) Method for preparing isophorone diisocyanate
CN108636456B (en) Salen metal complex catalyst, and preparation method and application thereof
CN107641197A (en) A kind of copolyreaction catalyst using carbon dioxide with 7-oxa-bicyclo[4.1.0 as monomer
Kipshagen et al. Formic acid as H 2 storage system: hydrogenation of CO 2 and decomposition of formic acid by solid molecular phosphine catalysts
CN113786837A (en) Method for preparing cyclopentanone and cyclopentanol through furfural hydrogenation rearrangement
CN108424359B (en) Ruthenium complex in water phase for catalyzing CO2Method for preparing formate/formic acid by hydrogenation reduction
CN105778093A (en) Halogen-free catalytic polyphenylene sulfide and preparation method thereof
CN114599660A (en) For the synthesis of CO2Catalyst composition for producing cyclic carbonate with epoxide
CN110721727B (en) Oxford catalyst, preparation method thereof and application thereof in synthesis of multi-functionality five-membered cyclic carbonate
CN116354807B (en) Solvent-free synthesis method of nonmetal catalyst and application thereof
CN114082442B (en) Succinimidyl ionic liquid and method for synthesizing quinazoline-2, 4 (1H, 3H) -diketone by using same as catalyst

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination