CN114456295B - Preparation method of porous polyion liquid - Google Patents

Preparation method of porous polyion liquid Download PDF

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CN114456295B
CN114456295B CN202210097738.9A CN202210097738A CN114456295B CN 114456295 B CN114456295 B CN 114456295B CN 202210097738 A CN202210097738 A CN 202210097738A CN 114456295 B CN114456295 B CN 114456295B
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vinylimidazole
liquid
cyanomethyl
porous
polyionic liquid
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CN114456295A (en
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张哲�
靳亚娥
张乐
聂瑞
葸皎
彭辉
马国富
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Pingdingshan Deyuan Fine Chemicals Co ltd
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Baiyin Division Innovation Research Institute Of Northwest Normal University
Northwest Normal University
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F126/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F126/06—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/28—Treatment of water, waste water, or sewage by sorption
    • C02F1/285—Treatment of water, waste water, or sewage by sorption using synthetic organic sorbents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/34—Introducing sulfur atoms or sulfur-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/28—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a liquid phase from a macromolecular composition or article, e.g. drying of coagulum
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2101/00—Nature of the contaminant
    • C02F2101/30—Organic compounds
    • C02F2101/34—Organic compounds containing oxygen
    • C02F2101/345—Phenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2339/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Derivatives of such polymers
    • C08J2339/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member

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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • Polymers & Plastics (AREA)
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Abstract

The invention provides a preparation method of a porous polyionic liquid, which comprises the following steps: under the action of tetraalkylammonium hydroxide, the cationic polyionic liquid is self-assembled in a solvent to form the porous polyionic liquid. Compared with the prior art, the method can prepare the porous polyion liquid with different pore sizes by regulating and controlling the concentration of the cationic polyion liquid in the system, has the characteristics of simple operation and controllable and easy regulation of the pore sizes, can rapidly and simply optimize the pore structure of the polyion liquid according to the size of pollutant molecules flexibly, and is a low-cost and green method for improving the adsorption performance of the porous polyion liquid.

Description

Preparation method of porous polyion liquid
Technical Field
The invention particularly relates to a preparation method of a porous polyionic liquid.
Background
Ionic liquids are organic molten salts composed of ionic liquid positive and negative ions that are in a liquid state at or near room temperature. The polyionic liquid is polymerized by ionic liquid monomers, and has the characteristics of ionic liquid and polymer and overcomes the flow of ionic liquidMobility. According to charged ions in the main chain, polyionic liquids can be classified into: 1. cationic polyionic liquid, namely, cation is connected with a polymer main chain through covalent bonds, 2, anionic polyionic liquid, namely, anion is connected with the polymer main chain through covalent bonds, 3, amphoteric polyionic liquid, namely, cation and anion are connected with the polymer main chain through covalent bonds, and at present, the research of preparing cationic polyionic liquid through imidazole salt monomer polymerization is more. Through ion exchange (can be carried out before polymerization (monomer) or after polymerization (polymer)), polyion liquid with different counter ions can be obtained, the ion conductivity, hydrophilicity and hydrophobicity and other performances of the polyion liquid are regulated, and common counter ions of the cationic polyion liquid have Cl - 、Br - 、I - 、BF 4 - 、PF 6 - 、NO 3 - 、R’SO 4 - 、CF 3 SO 3 - 、PhSO 3 - 、Tf 2 N - 、(CF 3 ) 2 N - 、 (CN) 2 N - Etc.
The porous polyion liquid not only has the characteristics of the pore structure, high specific surface area and the like of the traditional adsorbent, but also has the advantages of high conductivity, large polarity and the like, and the porous polyion liquid can directly obtain a corresponding porous structure or graft the ionic liquid onto a polymer with the porous structure when an ionic liquid monomer is polymerized, but the pore structure of the polyion liquid is not easy to control and regulate by adopting the mode. Qiang Zhao et al in paper Hierarchically Structured Nanoporous Poly (Ionic Liquid Membranes: facile Preparation and Application in Fiber-optical pH Sensing) disclose a method of preparing a nanoporous polyionic Liquid membrane by reacting poly [ 1-cyanomethyl-3-vinylimidazole bis (trifluoromethylsulfonyl) imide]（PCMVImTf 2 N) and polyacrylic acid (PAA) are coated on glass, dried at 80 ℃ for 1h, soaked with 0.2wt% ammonia water for 2h, the carboxyl of the PAA is deprotonated under the action of the ammonia water, and the carboxylate anions and PCMVImTf are utilized 2 Electrostatic interactions of N imidazole cations and phase separation in waterAnd (3) separating to obtain the nano-porous polyion liquid membrane. Without ammonia treatment, a dense film without pores was obtained. The method can flexibly obtain the porous polyionic liquid, but has the defects that the porous polyionic liquid contains polyacrylic acid components and is not suitable for the use of counter ions such as halogen (such as Br) - 、Cl - ) Is a polyionic liquid.
Water is one of the most important resources for human survival and for the circulation of the ecosystem. At present, various industries such as textile industry, food industry, cosmetic industry, pharmaceutical industry and the like generate a large amount of wastewater, and many of the wastewater contains phenolic and azo organic pollutants, so that the wastewater is potentially harmful to human beings and the environment. P-nitrophenol (PNP) is a typical representation of phenolic contaminants, which can cause damage to organisms even at low concentrations. As a result, removal of organic contaminants from a body of water is becoming increasingly important. Amutha Chinnappan et al report on Green synthesis, characterization and catalytic efficiency of hypercross-linked porous polymeric ionic liquid networks towards 4-nitrophenol reduction, mainly on the synthesis of a porous polystyrene-ionic liquid material with a specific surface area of 541.13 m 2 And/g, using it as a catalyst to convert p-nitrophenol to p-aminophenol. In the article of Hierarchical porous polymeric ionic liquids with excellent adsorption performance for phenolic compounds reported by Lili Zhang et al, the adsorption of p-nitrophenol by the prepared imidazolyl polyionic liquid reaches 460 mg/g, and the imidazolyl polyionic liquid is an adsorbent with application prospect. In the paper Highly Salt Resistant Polymer Supported Ionic Liquid Adsorbent for Ultrahigh Capacity Removal of p-Nitrophenol from Water published by Meng Cheng et al, 1-amino-3 methyl imidazole bromide is grafted onto chloromethyl styrene to adsorb p-nitrophenol, the adsorption capacity can reach over 1269 mg/g, and the product has the highest adsorption capacity to p-nitrophenol, which is a polyion liquid adsorbent reported at present, but chloromethyl styrene is used in the product, so that the manufacturing cost and process of the product are influenced.
Disclosure of Invention
In order to solve the problem that the pore size of the existing cationic porous polyionic liquid is not easy to regulate and control, the invention provides a method for preparing the porous polyionic liquid, which can simply and flexibly regulate and control the pore size of the porous polyionic liquid.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows.
A method for preparing a porous polyionic liquid, comprising:
under the action of tetraalkylammonium hydroxide, the cationic polyionic liquid is self-assembled in a solvent to form the porous polyionic liquid.
Preferably, the cationic polyionic liquid is an imidazole polyionic liquid.
Preferably, the imidazole polyionic liquid has the following chemical structure:wherein R is alkyl or cyanoalkyl, A - Is Cl - 、Br - 、I - 、BF 4 - 、PF 6 - 、NO 3 - 、R’SO 4 - 、CF 3 SO 3 - 、PhSO 3 - 、Tf 2 N - 、(CF 3 ) 2 N - 、(CN) 2 N - R' is alkyl, the carbon number of the alkyl is 1-8, and the carbon number of the cyanoalkyl is 2-9.
Alkyl is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl, and cyanoalkyl is cyanomethyl, cyanoethyl, cyanopropyl, cyanobutyl, cyanopentyl, cyanohexyl, cyanoheptyl or cyanooctyl.
Preferably, the tetraalkylammonium hydroxide is tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, or tetrabutylammonium hydroxide.
Preferably, the concentration of the tetraalkylammonium hydroxide in the system is 1-10wt%.
More preferably, the concentration of tetraalkylammonium hydroxide is 2 to 5wt%.
Preferably, the specific operation of the method comprises:
(1) Dissolving cationic polyion liquid to obtain solution A;
(2) Dissolving tetraalkylammonium hydroxide to obtain a solution B;
(3) And (3) dropwise adding the solution A into the solution B under stirring, and self-assembling to obtain the porous polyion liquid.
Preferably, the cationic polyionic liquid is poly [ 1-cyanomethyl-3-vinylimidazole bis (trifluoromethanesulfonyl) imide ].
Preferably, the cationic polyionic liquid is dissolved with N, N-Dimethylimide (DMF).
Preferably, the tetraalkylammonium hydroxide is dissolved with ethylene glycol.
Preferably, the preparation process of the poly [ 1-cyanomethyl-3-vinylimidazole bis (trifluoromethanesulfonyl) imide ] comprises the following steps:
synthesis of 1-cyanomethyl-3-vinylimidazole ammonium bromide monomer: reacting 1-vinylimidazole with bromoacetonitrile in an acetone solvent to obtain 1-cyanomethyl-3-vinylimidazole ammonium bromide;
synthesis of Poly (1-cyanomethyl 3-vinylimidazole ammonium bromide): dissolving 1-cyanomethyl-3-vinylimidazole ammonium bromide in a dimethyl sulfoxide (DMSO) solvent, and carrying out reflux reaction under the action of an initiator to obtain poly (1-cyanomethyl-3-vinylimidazole ammonium bromide);
anion exchange: dissolving poly (1-cyanomethyl-3-vinylimidazole ammonium bromide) in water, adding bis (trifluoromethanesulfonyl) imide lithium salt, and reacting to obtain poly [ 1-cyanomethyl-3-vinylimidazole bis (trifluoromethanesulfonyl) imide ].
Preferably, the molar ratio of 1-vinylimidazole to bromoacetonitrile is 1:1, and the reaction is carried out at room temperature.
Preferably, the initiator is Azobisisobutyronitrile (AIBN), the amount of the initiator is 1-3% of the mass of the monomer, and the temperature of the reflux reaction is 70-80 ℃.
Preferably, the dosage of the lithium bistrifluoromethane sulfonyl imide salt is 1.2-1.5 times of the mass of the poly (1-cyanomethyl 3-vinylimidazole ammonium bromide), and the reaction is carried out at room temperature.
The porous polyion liquid is prepared by the method.
The porous polyion liquid is used as an adsorbent in the treatment of phenolic pollutant wastewater.
Preferably, the phenolic contaminant is nitrophenol.
More preferably, the nitrophenol is para-nitrophenol.
Advantageous effects
Compared with the prior art, the method can prepare the porous polyion liquid with different pore sizes by regulating and controlling the concentration of the cationic polyion liquid in the system, has the characteristics of simple operation and controllable and easy regulation of the pore size, and can rapidly, simply and conveniently optimize the pore structure of the polyion liquid according to the size of pollutant molecules.
The porous polyion liquid can design proper pore distribution of adsorption of the phenolic compound according to the molecular size of the phenolic compound, and positive charges carried by the cationic polyion body can form electrostatic interaction with the phenolic compound with negative charges, so that the porous polyion liquid is an excellent phenolic pollutant adsorbent.
With PCMVImTf 2 N is an example, and after being optimized by the method of the invention, the PCMVImTf can be obviously displayed 2 N is capable of absorbing p-nitrophenol, and the maximum absorption capacity can reach 820.3mg/g, so that the method is a way for rapidly and effectively improving the absorption performance of the porous polyion liquid with low cost.
Drawings
FIG. 1 is a scanning electron micrograph of the PILC of the present invention.
FIG. 2 is an infrared spectrum of the PILC of the present invention.
FIG. 3 is an adsorption kinetics plot for PILC of the present invention.
FIG. 4 is a graph showing the effect of pH on the adsorption of p-nitrophenol by PILC according to the present invention.
Detailed Description
The technical scheme of the invention is further described in detail below with reference to the attached drawings and the preferred embodiments.
Tetraalkylammonium hydroxides are very hygroscopic and can rapidly absorb carbon dioxide in air to form carbonates. The commodity is usually an aqueous solution with a concentration of 10% -25%.
Example 1 PCMVImTf 2 N is an example
Synthesis of 1-cyanomethyl-3-vinylimidazole ammonium bromide monomer (CMVImBr): 5 g (0.106 mol) 1-vinylimidazole and 6.37 g (0.106 mol) bromoacetonitrile were added to a 100 mL round bottom flask containing 14 mL acetone. The mixture was stirred at room temperature for 24 hours, filtered and washed three times with diethyl ether and finally dried under vacuum at room temperature for 24 hours.
Synthesis of poly (1-cyanomethyl 3-vinylimidazole ammonium bromide) (PCAVImBr): 4g of CMVImBr and 80 mg of AIBN were added to a round-bottomed flask containing 40 mL of DMSO, the mixture was refluxed under stirring at 75℃for 24 hours under nitrogen, the reaction mixture was added dropwise to excess THF (tetrahydrofuran) as it cooled to room temperature, the precipitate was filtered and washed with a large amount of ethanol, and finally dried under vacuum at 60℃for further use.
Anion exchange: 10 g of PCAVImBr is dissolved in 200 mL deionized water, 100 mL of 13 g bis (trifluoromethanesulfonyl) imide lithium salt (LiTFSl) aqueous solution is added dropwise into the PCAVImBr solution, the reaction mixture is stirred for 2 hours at room temperature, the precipitate is filtered and washed three times with deionized water, finally the solution is dried in vacuum at 60 ℃ to obtain poly [ 1-cyanomethyl-3-vinylimidazole bis (trifluoromethanesulfonyl) imide]（PCMVImTf 2 N, indicated by PIL).
Preparation of porous polyion liquid adsorbent: an amount of PCMVImTf 2 N was dissolved in DMF and stirred to form a homogeneous clear solution. 30 mL ethylene glycol and 5 mL of 25% tetramethylammonium hydroxide solution were added to a beaker and placed in an ultrasonic (model SonifierW-450D) bath at 25 ℃.3 mL PCMVImTf 2 The N solution was added drop wise to the tetramethylammonium hydroxide solution with stirring (900 rpm) and ultrasound (40% ultrasound amplitude). Adding PCMVImTf 2 The N solution immediately became turbid, and after the addition was completed, the ultrasonic treatment was continued for 5 min. Centrifugally collecting, washing with ethanol for 4 times, and vacuum drying at 50deg.C until constant weight to obtain porous PCMVImTf 2 N (indicated by PILC). Nitrogen adsorption and desorption experiments show that the concentration of PIL in DMF is 15wt%, and the obtained PILC pore size is 59.76 nm. For other cationic type of dissociationThe sub-liquid can realize the regulation of the pore size according to the step.
The results of the regulation of the pore volume of PILC by its concentration in DMF are given in the following table:
fig. 1 is a scanning electron micrograph of PILC, which is a nano-scale particle.
FIG. 2 is an infrared spectrum of PILC, 1625 cm -1 Is the stretching vibration peak of C=N bond on imidazole ring, 1328 cm -1 Is a characteristic peak of S=O bond in anion, 1360-1020 cm -1 Is a characteristic peak of C-N bond in acetonitrile. These characteristic peaks indicate that the preparation of the porous polyionic liquid was successful.
Adsorption experiment
5 mg of PILC was weighed into a 50 mL Erlenmeyer flask containing 20 mL different concentrations of p-nitrophenol (PNP) and the mixture was then shaken by a shaker at 150 rpm. After a certain period of time, the mixture was taken out, and its absorbance was measured with UV-vis to obtain the residual concentration of p-nitrophenol.
(1) Adsorption kinetics study
As can be seen from FIG. 3, the equilibrium time for PILC adsorption of PNP is 4h, and the maximum adsorption amount can reach 820.3mg/g. Under the same adsorption conditions, the maximum adsorption amount of PIL to PNP before unregulated is only 87.1 mg/g.
(2) Influence of the pH of the solution on the adsorption capacity
As can be seen from fig. 4, the adsorption of PNP by the PILC is best under neutral conditions.
Finally, it should be noted that: the foregoing description is only a preferred embodiment of the present invention, and the present invention is not limited thereto, but it is to be understood that modifications and equivalents of some of the technical features described in the foregoing embodiments may be made by those skilled in the art, although the present invention has been described in detail with reference to the foregoing embodiments. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims (14)

1. A method for preparing a porous polyionic liquid, comprising:
under the action of tetraalkylammonium hydroxide, the cationic polyionic liquid is self-assembled in a solvent to form porous polyionic liquid;
the cationic polyionic liquid is imidazole polyionic liquid, and the imidazole polyionic liquid has the following chemical structure:wherein R is alkyl or cyanoalkyl, A - Is Cl - 、Br - 、I - 、BF 4 - 、PF 6 - 、NO 3 - 、R’SO 4 - 、CF 3 SO 3 - 、PhSO 3 - 、Tf 2 N - 、(CF 3 ) 2 N - 、(CN) 2 N - R' is alkyl, the carbon number of the alkyl is 1-8, and the carbon number of the cyanoalkyl is 2-9;
the specific operation process comprises the following steps:
(1) Dissolving cationic polyion liquid to obtain solution A;
(2) Dissolving tetraalkylammonium hydroxide to obtain a solution B;
(3) And (3) dropwise adding the solution A into the solution B under stirring, and self-assembling to obtain the porous polyion liquid.
2. The method of manufacturing according to claim 1, characterized in that: the tetraalkylammonium hydroxide is tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, or tetrabutylammonium hydroxide.
3. The method of manufacturing according to claim 1, characterized in that: the concentration of the tetraalkylammonium hydroxide in the system is 1-10wt%.
4. A method of preparation according to claim 3, characterized in that: the concentration of the tetraalkylammonium hydroxide is 2-5wt%.
5. The method of manufacturing according to claim 1, characterized in that: the cationic polyionic liquid is poly [ 1-cyanomethyl-3-vinylimidazole bis (trifluoromethanesulfonyl) imide ].
6. The method of manufacturing according to claim 5, wherein: the cationic polyionic liquid was dissolved with N, N-dimethylimide and the tetraalkylammonium hydroxide with ethylene glycol.
7. The method of manufacturing according to claim 5 or 6, characterized in that: the preparation process of the poly [ 1-cyanomethyl-3-vinylimidazole bis (trifluoromethanesulfonyl) imide ] comprises the following steps:
synthesis of 1-cyanomethyl-3-vinylimidazole ammonium bromide monomer: reacting 1-vinylimidazole with bromoacetonitrile in an acetone solvent to obtain 1-cyanomethyl-3-vinylimidazole ammonium bromide;
synthesis of Poly (1-cyanomethyl 3-vinylimidazole ammonium bromide): dissolving 1-cyanomethyl-3-vinylimidazole ammonium bromide in a dimethyl sulfoxide solvent, and carrying out reflux reaction under the action of an initiator to obtain poly (1-cyanomethyl-3-vinylimidazole ammonium bromide);
anion exchange: dissolving poly (1-cyanomethyl-3-vinylimidazole ammonium bromide) in water, adding bis (trifluoromethanesulfonyl) imide lithium salt, and reacting to obtain poly [ 1-cyanomethyl-3-vinylimidazole bis (trifluoromethanesulfonyl) imide ].
8. The method of manufacturing according to claim 7, wherein: the molar ratio of the 1-vinylimidazole to bromoacetonitrile is 1:1, and the reaction is carried out at room temperature.
9. The method of manufacturing according to claim 7, wherein: the initiator is azodiisobutyronitrile, the amount of the initiator is 1-3% of the mass of the monomer, and the temperature of the reflux reaction is 70-80 ℃.
10. The method of manufacturing according to claim 7, wherein: the dosage of the lithium bis (trifluoromethanesulfonyl) imide is 1.2-1.5 times of the mass of the poly (1-cyanomethyl 3-vinylimidazole ammonium bromide), and the reaction is carried out at room temperature.
11. The porous polyionic liquid prepared by the method of any one of claims 1-10.
12. Use of the porous polyionic liquid of claim 11 as an adsorbent in the treatment of phenolic pollutant wastewater.
13. The use according to claim 12, characterized in that: the phenolic contaminant is nitrophenol.
14. The use according to claim 13, characterized in that: the nitrophenol is p-nitrophenol.
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CN114716597B (en) * 2022-05-18 2023-04-11 河北科技大学 Solid ionic organic porous polymer and preparation method and application thereof
CN115193418B (en) * 2022-07-26 2023-09-26 西北师范大学 Preparation method of polyion liquid/attapulgite hybrid material and application of polyion liquid/attapulgite hybrid material in adsorption of p-nitrophenol

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US20090266230A1 (en) * 2004-08-05 2009-10-29 Maciej Radosz Poly(ionic liquid)s as new materials for co2 separation and other applications
CN105542048A (en) * 2015-11-16 2016-05-04 浙江理工大学 Polymeric ionic liquids ordered structure and preparation method thereof
CN109400771A (en) * 2018-10-26 2019-03-01 绍兴文理学院 The preparation method and applications of super cross-linked porous poly ion liquid material
CN110078702A (en) * 2019-05-30 2019-08-02 中国科学院过程工程研究所 A kind of method of poly ion liquid frame catalyst preparation cyclic carbonate

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090266230A1 (en) * 2004-08-05 2009-10-29 Maciej Radosz Poly(ionic liquid)s as new materials for co2 separation and other applications
CN105542048A (en) * 2015-11-16 2016-05-04 浙江理工大学 Polymeric ionic liquids ordered structure and preparation method thereof
CN109400771A (en) * 2018-10-26 2019-03-01 绍兴文理学院 The preparation method and applications of super cross-linked porous poly ion liquid material
CN110078702A (en) * 2019-05-30 2019-08-02 中国科学院过程工程研究所 A kind of method of poly ion liquid frame catalyst preparation cyclic carbonate

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