CN115715926B - Novel high-performance porous polyion liquid filler and preparation method and application thereof - Google Patents
Novel high-performance porous polyion liquid filler and preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to a novel high-performance porous polyionic liquid filler, and a preparation method and application thereof, wherein the filler comprises the following components: ionic liquid monomer, cross-linking agent, free radical initiator, solution containing small volume anions and solvent. The preparation method comprises the following steps of S1, synthesizing polyionic liquid; step S2: and (3) anion exchange reaction. The novel porous polyion liquid material is used as the filler, has rich pore canal structure and controllable pore diameter, enhances the adsorption effect on organic odor, enlarges the contact surface of the odor and organisms, has the advantages of high mechanical strength, corrosion resistance, aging resistance, small mass, capability of preventing compaction and gas short flow, large specific surface area, capability of absorbing heavy metal ions, sound insulation and vibration reduction, capability of effectively reducing the film forming time, capability of increasing the adhesion quantity and liquid holdup of microorganisms, more contribution to the survival of deodorizing bacteria, buffer function and capability of recycling.
Description
Technical Field
The invention relates to the technical field of industrial waste gas treatment, in particular to a novel high-performance porous polyion liquid filler, and a preparation method and application thereof.
Background
The filler is a core part of the deodorization performance of the biological trickling filtration tower, is used as an important carrier to provide a place for the growth and propagation of microorganisms, is also an important conducting medium, and can provide a large mass transfer area for liquid, gas and solid phases. Therefore, the proper packing is selected to maintain good treatment efficiency of the biological trickling filtration tower, and meanwhile, the operation pressure loss can be reduced, so that the operation and maintenance cost of the trickling filtration tower is saved.
The development process of the filler of the biotrickling filter is gradually transition from organic filler to inorganic filler. The organic filler is used as a carrier for microorganism growth in the biological deodorization process and provides nutrients for the growth of microorganisms, but the filler is gradually consumed and finally collapses due to long-term operation. The existing biotrickling filter mainly uses inorganic inert fillers, and conventional inorganic fillers such as plastic fillers, ceramsite fillers and the like have the defects of small liquid holdup, difficult microorganism adhesion, long film forming time, poor adsorption capacity, saturated adsorption capacity due to the increase of time and the like.
How to design a novel filler which can be used for a biological trickling filter, so that deodorization is more thorough and complete, and the problems of small liquid holdup, difficult adhesion of microorganisms, long film forming time, poor adsorption capacity, saturated adsorption capacity due to the increase of the adsorption capacity along with time and the like of the existing filler can be overcome, so that the novel filler becomes a technical problem to be solved in the field.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide a novel high-performance porous polyionic liquid filler, and a preparation method and application thereof.
Specifically, the invention aims to provide a novel high-performance porous polyionic liquid filler, which comprises the following components in parts by weight: 50.7-73.9 parts of ionic liquid monomer, 25.4-48.3 parts of cross-linking agent and free radical initiator: 0.03-0.15 parts, solution containing small volume of anions 30 parts and solvent 100 parts.
Further, the ionic liquid monomer is 3,3' - (methyl-1, 1-diyl) bis (1-vinyl-3-imidazolium) bisacrylonitrile salt.
Further, the cross-linking agent is one of divinylbenzene and ethylene glycol dimethacrylate.
Further, the free radical initiator is azobisisobutyronitrile and the solvent is methanol.
Further, the solution containing small-volume anions is one of saturated sodium chloride aqueous solution, saturated sodium bromide aqueous solution and saturated sodium acetate aqueous solution.
The invention also aims to provide a preparation method of the novel high-performance porous polyionic liquid filler, which comprises the following steps: step S1, synthesizing polyion liquid; step S2: and (3) anion exchange reaction.
Further, the step S1 includes: s10: mixing ionic liquid monomer, cross-linking agent and solvent under nitrogen protection at a certain temperature and stirring speed; s11: and (3) adding a free radical initiator into the solution obtained in the step (S10) at a certain temperature and stirring speed, refluxing and stirring, cooling, removing the solvent, washing with diethyl ether and deionized water, and vacuum drying to obtain a primary product.
Further, in the step S10, the solvent is methanol, and the solvent is stirred for 2-4 hours at 20-40 ℃ at a rotating speed of 300-500 rpm.
Further, in the step S11, the free radical initiator is dropwise added at the temperature of 20-40 ℃, reflux stirring is carried out for 20-30 hours, the rotating speed is 300-500 revolutions per minute, and the obtained product is placed in a vacuum box at the temperature of 50 ℃ for drying for 12-24 hours.
Further, the step S2 includes: s20: taking 5g of the polyionic liquid in the step S1, adding a solution containing anions with a small volume compared with the polyionic liquid, and stirring at a certain temperature; s21: after the reaction is stopped, decompressing and filtering to obtain solid, washing with absolute ethyl alcohol, and detecting anions under an ultraviolet lamp until the exchange is complete; s22: washing the product obtained in the step S21 by absolute ethyl alcohol and deionized water, and vacuum drying to obtain a final product, namely the porous polyion liquid filler.
Further, the solution containing small volume of anions is added in the step S20 and stirred for 10 to 15 hours at the temperature of 20 to 40 ℃ at the rotating speed of 300 to 500 revolutions per minute.
Further, the product obtained in the step S21 is washed by absolute ethyl alcohol and deionized water in the step S22, then is dried in vacuum at 50 ℃ for 12-24 hours, and is taken out and dried in vacuum to obtain the polyion liquid filler with the porous structure.
The invention further aims at providing an application of the novel high-performance porous polyion liquid filler to a biological trickling filter.
The novel high-performance porous polyionic liquid filler and the preparation method and application thereof have the beneficial effects that:
(1) The novel porous polyion liquid material is adopted as the filler, the porous polyion liquid material has rich pore channel structure and controllable pore size, the porosity of the filler is increased, the adsorption effect on organic odor is enhanced, and the contact surface between the odor and organisms is enlarged; the mechanical strength is high, the corrosion resistance and the aging resistance are high, the mass is low, and the compaction and the occurrence of short gas flow can be prevented; the specific surface area is large, heavy metal ions can be absorbed, the sound insulation and shock absorption can effectively reduce the film forming time, and the microorganism attachment and liquid holdup are increased, so that the deodorant is more beneficial to survival of deodorant bacteria; the pH value of the filler can be changed by adding different substances, the filler has a buffer function, and the filler can be recycled to maintain long-term stable operation of the deodorizing system.
(2) The surfactant is not added in the preparation process, and the surfactant can pollute the water body, soil and other environments, and when the concentration of the surfactant reaches 1mg/L, persistent foam can appear, so that the odor of the water body caused by gas exchange between the water body and the atmosphere is weakened; the surfactant can also reduce the liquid holdup of the polyion liquid, and can interact with liquid components in the cell membrane to force the cell membrane to dissolve and kill microorganisms, so that the method is unfavorable for the attached growth of the microorganisms; can carry out exchange reaction with ions in the water body, changes the pH value, and is unfavorable for the survival of microorganisms. The invention does not add surfactant in the synthesis process, reduces the harm to the environment, prolongs the service cycle of the trickling filtration tower, can repeatedly use the filler for a long time, and is more suitable for the growth of microorganisms.
(3) The porous polyion liquid filler can adsorb heavy metal ions, the heavy metal ions can act with biological macromolecules such as amino acid, nucleic acid, fatty acid and the like in microbial cells, the metal ions can be combined with groups contained in the biological components to replace the original metal on active sites, the metal ion demand of a microbial body is extremely low, when the metal ion content exceeds the threshold value born by microbial growth, metabolic activity is inhibited, even the composition of a biological community is changed, the adaptability to external change impact force is reduced, and the deodorizing capability is greatly reduced, so that the porous polyion material can effectively solve the problem.
(4) The anion exchange preparation method is adopted, and the prepared product has larger specific surface area and higher porosity. By utilizing the anion exchange property, large-volume template anions in the polyion liquid are exchanged into small-volume anions, and the space occupied by the template anions in the polyion liquid is released, so that the porous polyion liquid with high specific surface area and a multistage pore structure is designed and synthesized. The porous polyion liquid synthesized by the anion exchange method has stable nanoparticle morphology, high specific surface area and multi-stage (mesoporous-microporous) porous structure. The porous structure is combined with the large specific surface, so that the fixation of the biological film is promoted, the adhesion and the growth of microorganisms are facilitated, more types of microorganisms can enter the filler, and adsorbed organic matters can be degraded for a longer time without waste. Meanwhile, different microbial communities are easy to form due to different microbial distribution conditions and different conditions, and pollutants with different properties are treated.
Detailed Description
The technical solutions of the embodiments of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention. The specific conditions are not noted in the examples and are carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or apparatus used were conventional products commercially available without the manufacturer's attention.
Preparation of ionic liquid monomer:
slowly dropwise adding dibromomethane solution into a mixture of vinyl imidazole and chloroform by using a constant pressure titration funnel, reflux-stirring, reacting for 24 hours, collecting solid, and vacuum-drying to obtain 3,3' - (methyl-1, 1-diyl) bis (1-vinyl-3-imidazolium) dibromo salt; mixing and stirring the mixture with acrylonitrile and deionized water for reaction for 12 hours, collecting filtrate, concentrating and drying to obtain the product 3,3' - (methyl-1, 1-diyl) bis (1-vinyl-3-imidazolium) bisacrylonitrile salt.
Example 1:
weighing the following raw materials in parts by weight: 50.7 parts of ionic liquid monomer 3,3' - (methyl-1, 1-diyl) bis (1-vinyl-3-imidazolium) bisacrylonitrile salt, 25.4 parts of cross-linking agent divinylbenzene, 0.03 part of free radical initiator azodiisobutyronitrile, 100 parts of solvent methanol and 30 parts of saturated sodium chloride aqueous solution respectively.
(1) The preparation method comprises the following steps:
s1, synthesizing polyionic liquid:
and (3) placing the ionic liquid monomer, the cross-linking agent and the solvent methanol into a round bottom flask, stirring for 2 hours at 20 ℃ under nitrogen atmosphere, rotating at 300 rpm, fully mixing, adding the free radical initiator azodiisobutyronitrile, and refluxing and stirring for 24 hours. After the reaction was completed, cooled to room temperature, the solvent was removed by decantation, and the resulting polymer was washed with diethyl ether and deionized water several times. And drying the product in a vacuum drying oven at 50 ℃ for 12 hours to obtain the primary product polyionic liquid.
S2 anion exchange reaction:
5g of the preliminary product obtained in S1 and a saturated aqueous NaCl solution (30 mL) were stirred in a round-bottomed flask at 20℃for 10 hours at a speed of 300 rpm. After the reaction is stopped, the solid is obtained by decompression and filtration, the steps are repeated by repeated washing with absolute ethyl alcohol, and salicylic acid radical is detected by thin layer chromatography under an ultraviolet lamp until the exchange is complete. The product was washed with absolute ethanol and deionized water and dried in a vacuum oven at 50 ℃ for 12 hours. Obtaining the final product porous polyion liquid. Toluene was used as a treatment target, and the specific surface area, the film formation time, the removal rate, the MLSS, the porosity, and the liquid holding amount were examined, and the test results are shown in table 2.
Example 2:
weighing the following raw materials in parts by weight: 63.3 parts of ionic liquid monomer 3,3' - (methyl-1, 1-diyl) bis (1-vinyl-3-imidazolium) bisacrylonitrile salt, 31.8 parts of cross-linking agent ethylene glycol dimethacrylate, 0.05 part of free radical initiator azodiisobutyronitrile, 100 parts of solvent methanol and 30 parts of saturated sodium bromide aqueous solution.
(1) The preparation method comprises the following steps:
s1, synthesizing polyionic liquid:
and (3) placing the ionic liquid monomer, the cross-linking agent and the solvent methanol into a round bottom flask, stirring for 3 hours at 30 ℃ under nitrogen atmosphere, rotating at 400 rpm, fully mixing, adding the free radical initiator azodiisobutyronitrile, and refluxing and stirring for 24 hours. After the reaction was completed, cooled to room temperature, the solvent was removed by decantation, and the resulting polymer was washed with diethyl ether and deionized water several times. And drying the product in a vacuum drying oven at 50 ℃ for 20 hours to obtain the primary product polyionic liquid.
S2 anion exchange reaction:
5g of the preliminary product obtained in S1 and a saturated aqueous NaBr solution (30 mL) were stirred in a round-bottomed flask at 30℃for 12 hours at a rotation speed of 400 rpm. After the reaction is stopped, the solid is obtained by decompression and filtration, the steps are repeated by repeated washing with absolute ethyl alcohol, and salicylic acid radical is detected by thin layer chromatography under an ultraviolet lamp until the exchange is complete. The product was washed with absolute ethanol and deionized water and dried in a vacuum oven at 50 ℃ for 20 hours. Obtaining the final product porous polyion liquid. Toluene was used as a treatment target, and the specific surface area, the film formation time, the removal rate, the MLSS, the porosity, and the liquid holding amount were examined, and the test results are shown in table 2.
Example 3:
weighing the following raw materials in parts by weight: 73.9 parts of ionic liquid monomer 3,3' - (methyl-1, 1-diyl) bis (1-vinyl-3-imidazolium) bisacrylonitrile salt, 48.3 parts of cross-linking agent divinylbenzene, 0.15 part of free radical initiator azodiisobutyronitrile, 100 parts of solvent methanol and 30 parts of saturated sodium acetate aqueous solution.
(1) The preparation method comprises the following steps:
s1, synthesizing polyionic liquid:
and (3) placing the ionic liquid monomer, the cross-linking agent and the solvent methanol into a round bottom flask, stirring for 4 hours at 40 ℃ under nitrogen atmosphere, rotating at 500 rpm, adding the free radical initiator azodiisobutyronitrile after fully mixing, and refluxing and stirring for 24 hours. After the reaction was completed, cooled to room temperature, the solvent was removed by decantation, and the resulting polymer was washed with diethyl ether and deionized water several times. The product is dried in a vacuum drying oven at 50 ℃ for 24 hours to obtain the preliminary product polyionic liquid.
S2 anion exchange reaction:
5g of the preliminary product obtained in S1 and a saturated aqueous solution of sodium acetate (30 mL) were stirred in a round-bottomed flask at 40℃for 15 hours at a rotation speed of 500 rpm. After the reaction is stopped, the solid is obtained by decompression and filtration, the steps are repeated by repeated washing with absolute ethyl alcohol, and salicylic acid radical is detected by thin layer chromatography under an ultraviolet lamp until the exchange is complete. The product was washed with absolute ethanol and deionized water and dried in a vacuum oven at 50 ℃ for 24 hours. Obtaining the final product porous polyion liquid. Toluene was used as a treatment target, and the specific surface area, the film formation time, the removal rate, the MLSS, the porosity, and the liquid holding amount were examined, and the test results are shown in table 2.
Comparative example 1
Weighing the following raw materials in parts by weight: 50.7 parts of ionic liquid monomer 3,3' - (methyl-1, 1-diyl) bis (1-vinyl-3-imidazolium) bisacrylonitrile salt, 0.03 part of free radical initiator azodiisobutyronitrile, 100 parts of solvent methanol and 30 parts of saturated sodium chloride aqueous solution respectively.
(1) The preparation method comprises the following steps:
s1, synthesizing polyionic liquid:
and placing the ionic liquid monomer and the solvent methanol into a round bottom flask, stirring for 2 hours at 20 ℃ under nitrogen atmosphere, rotating at 300 rpm, fully mixing, adding the free radical initiator azodiisobutyronitrile, and refluxing and stirring for 24 hours. After the reaction was completed, cooled to room temperature, the solvent was removed by decantation, and the resulting polymer was washed with diethyl ether and deionized water several times. And drying the product in a vacuum drying oven at 50 ℃ for 12 hours to obtain the primary product polyionic liquid.
S2 anion exchange reaction:
5g of the preliminary product obtained in S1 and a saturated aqueous NaCl solution (30 mL) were stirred in a round-bottomed flask at 20℃for 10 hours at a speed of 300 rpm. After the reaction is stopped, the solid is obtained by decompression and filtration, the steps are repeated by repeated washing with absolute ethyl alcohol, and salicylic acid radical is detected by thin layer chromatography under an ultraviolet lamp until the exchange is complete. The product was washed with absolute ethanol and deionized water and dried in a vacuum oven at 50 ℃ for 12 hours. Obtaining the final product porous polyion liquid. Toluene was used as a treatment target, and the specific surface area, the film formation time, the removal rate, the MLSS, the porosity, and the liquid holding amount were examined, and the test results are shown in table 2.
Comparative example 2
Weighing the following raw materials in parts by weight: 50.7 parts of ionic liquid monomer 3,3' - (methyl-1, 1-diyl) bis (1-vinyl-3-imidazolium) bisacrylonitrile salt, 25.4 parts of cross-linking agent divinylbenzene, 100 parts of solvent methanol and 30 parts of saturated sodium chloride aqueous solution respectively.
(1) The preparation method comprises the following steps:
s1, synthesizing polyionic liquid:
the ionic liquid monomer, the cross-linking agent and the solvent methanol are placed in a round bottom flask, and are stirred for 2 hours at 20 ℃ under the nitrogen atmosphere, and the rotating speed is 300 revolutions per minute. After the reaction was completed, cooled to room temperature, the solvent was removed by decantation, and the resulting polymer was washed with diethyl ether and deionized water several times. And drying the product in a vacuum drying oven at 50 ℃ for 12 hours to obtain the primary product polyionic liquid.
S2 anion exchange reaction:
5g of the preliminary product obtained in S1 and a saturated aqueous NaCl solution (30 mL) were stirred in a round-bottomed flask at 20℃for 10 hours at a speed of 300 rpm. After the reaction is stopped, the solid is obtained by decompression and filtration, the steps are repeated by repeated washing with absolute ethyl alcohol, and salicylic acid radical is detected by thin layer chromatography under an ultraviolet lamp until the exchange is complete. The product was washed with absolute ethanol and deionized water and dried in a vacuum oven at 50 ℃ for 12 hours. Obtaining the final product porous polyion liquid. Toluene was used as a treatment target, and the specific surface area, the film formation time, the removal rate, the MLSS, the porosity, and the liquid holding amount were examined, and the test results are shown in table 2.
Comparative example 3
Weighing the following raw materials in parts by weight: 50.7 parts of ionic liquid monomer 3,3' - (methyl-1, 1-diyl) bis (1-vinyl-3-imidazolium) bisacrylonitrile salt, 25.4 parts of cross-linking agent divinylbenzene, 0.03 part of free radical initiator azodiisobutyronitrile and 100 parts of solvent methanol.
(1) The preparation method comprises the following steps:
s1, synthesizing polyionic liquid:
and (3) placing the ionic liquid monomer, the cross-linking agent and the solvent methanol into a round bottom flask, stirring for 2 hours at 20 ℃ under nitrogen atmosphere, rotating at 300 rpm, fully mixing, adding the free radical initiator azodiisobutyronitrile, and refluxing and stirring for 24 hours. After the reaction was completed, cooled to room temperature, the solvent was removed by decantation, and the resulting polymer was washed with diethyl ether and deionized water several times. And drying the product in a vacuum drying oven at 50 ℃ for 12 hours to obtain the primary product polyionic liquid.
Toluene was used as a treatment target, and the specific surface area, the film formation time, the removal rate, the MLSS, the porosity, and the liquid holding amount were examined, and the test results are shown in table 2.
From the above examples 1-3, it can be seen that, when 50.7-73.9 parts of ionic liquid monomer, 25.4-48.3 parts of cross-linking agent, 0.03-0.15 parts of free radical initiator, 30 parts of solution containing small volume of anions, and 100 parts of solvent, the specific surface area, film forming time, removal rate, MLSS, porosity and liquid holdup are examined, and the test results are satisfactory, the novel porous polyionic liquid material is adopted as the filler, and the novel porous polyionic liquid material has rich pore structure and controllable pore size, increases the porosity of the filler, enhances the adsorption effect on organic odor, and enlarges the contact surface between the odor and organisms; the mechanical strength is high, the corrosion resistance and the aging resistance are high, the mass is low, and the compaction and the occurrence of short gas flow can be prevented; the specific surface area is large, heavy metal ions can be absorbed, the sound insulation and shock absorption can effectively reduce the film forming time, and the microorganism adhesion and liquid holdup are increased.
As can be seen from comparative examples 1-2, when the cross-linking agent and the free radical initiator are not adopted, the specific surface area, the film forming time, the removal rate, the MLSS, the porosity and the liquid holdup are examined, and the test results are unsatisfactory, because the ionic liquid monomer, the cross-linking agent and the free radical initiator have a certain synergistic effect, and the porosity and the specific surface area of the filler are increased.
As can be seen from comparative example 3, when the anion exchange reaction is not performed by using the solution containing small volume of anions, the specific surface area, the membrane formation time, the removal rate, the MLSS, the porosity and the liquid holdup are examined, and the test results are poor, because the anion exchange property is utilized to exchange large volume of template anions in the polyion liquid into small volume of anions and release the space occupied by the template anions in the polyion liquid, thereby designing and synthesizing the porous polyion liquid with high specific surface area and multi-stage pore structure. The porous polyion liquid synthesized by the anion exchange method has stable nanoparticle morphology, high specific surface area and multi-stage (mesoporous-microporous) porous structure.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
The foregoing description of the preferred embodiments of the invention is not intended to be limiting, but rather is intended to cover all modifications, equivalents, and alternatives falling within the spirit and principles of the invention.
Claims (1)
1. The application of the novel high-performance porous polyion liquid filler in the biotrickling filter is characterized in that the preparation method of the porous polyion liquid filler comprises the following steps:
step S1, synthesizing polyion liquid; step S2: an anion exchange reaction;
the step S1 includes: s10: mixing ionic liquid monomer, cross-linking agent and solvent under nitrogen protection at a certain temperature and stirring speed; s11: adding a free radical initiator into the solution obtained in the step S10 at a certain temperature and stirring speed, refluxing and stirring, cooling, removing the solvent, washing with diethyl ether and deionized water, and vacuum drying to obtain a primary product;
50.7-73.9 parts of ionic liquid monomer, 25.4-48.3 parts of cross-linking agent, 0.03-0.15 part of free radical initiator, 30 parts of solution containing small-volume anions and 100 parts of solvent;
in the step S10, the solvent is methanol, and the solvent is stirred for 2 to 4 hours at the temperature of 20 to 40 ℃ and the rotating speed is 300 to 500 revolutions per minute;
in the step S11, the free radical initiator is dripped at the temperature of 20-40 ℃, the reflux stirring is carried out for 20-30 hours, the rotating speed is 300-500 rpm, and the obtained product is placed in a vacuum box at the temperature of 50 ℃ for drying for 12-24 hours;
the step S2 includes: s20: taking 5g of the polyionic liquid in the step S1, adding a solution containing anions with a small volume compared with the polyionic liquid, and stirring at a certain temperature; s21: after the reaction is stopped, decompressing and filtering to obtain solid, washing with absolute ethyl alcohol, and detecting anions under an ultraviolet lamp until the exchange is complete; s22: washing the product obtained in the step S21 by absolute ethyl alcohol and deionized water, and vacuum drying to obtain a final product, namely the porous polyion liquid filler;
adding a solution containing small volume of anions into the step S20, and stirring at the temperature of 20-40 ℃ for 10-15 hours at the rotating speed of 300-500 rpm;
washing the product obtained in the step S21 by using absolute ethyl alcohol and deionized water in the step S22, vacuum drying at 50 ℃ for 12-24 hours, and taking out the polyion liquid filler with a porous structure after vacuum drying;
the cross-linking agent is ethylene glycol dimethacrylate;
the free radical initiator is azodiisobutyronitrile, and the solvent is methanol;
the solution containing small-volume anions is one of saturated sodium bromide aqueous solution and saturated sodium acetate aqueous solution;
the ionic liquid monomer is 3,3' - (methyl-1, 1-diyl) bis (1-vinyl-3-imidazolium) bisacrylonitrile salt;
the preparation of the ionic liquid monomer comprises the following steps: slowly dropwise adding dibromomethane solution into a mixture of vinyl imidazole and chloroform by using a constant pressure titration funnel, reflux-stirring, reacting for 24 hours, collecting solid, and vacuum-drying to obtain 3,3' - (methyl-1, 1-diyl) bis (1-vinyl-3-imidazolium) dibromo salt; mixing and stirring the mixture with acrylonitrile and deionized water for reaction for 12 hours, collecting filtrate, concentrating and drying to obtain the product 3,3' - (methyl-1, 1-diyl) bis (1-vinyl-3-imidazolium) bisacrylonitrile salt.
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| GB849122A (en) * | 1958-02-03 | 1960-09-21 | Permutit Co Ltd | Improvements relating to ion-exchange resins and their manufacture |
| 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 |
| CN114957900A (en) * | 2022-04-29 | 2022-08-30 | 国家纳米科学中心 | Magnetic porous polyion liquid material, preparation method and device thereof |
| WO2022246381A1 (en) * | 2021-05-20 | 2022-11-24 | Versum Materials Us, Llc | Imidazolium-based poly(ionic liquid)s and use therefore |
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|---|---|---|---|---|
| GB849122A (en) * | 1958-02-03 | 1960-09-21 | Permutit Co Ltd | Improvements relating to ion-exchange resins and their manufacture |
| 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 |
| WO2022246381A1 (en) * | 2021-05-20 | 2022-11-24 | Versum Materials Us, Llc | Imidazolium-based poly(ionic liquid)s and use therefore |
| CN114957900A (en) * | 2022-04-29 | 2022-08-30 | 国家纳米科学中心 | Magnetic porous polyion liquid material, preparation method and device thereof |
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