CN114570337B - High-water-vapor-adsorption ionic liquid adsorbent and synthesis method and application thereof - Google Patents
High-water-vapor-adsorption ionic liquid adsorbent and synthesis method and application thereof Download PDFInfo
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Abstract
The invention discloses a method for synthesizing a high-moisture-content adsorption agglomeration ionic liquid adsorbent, belonging to the field of adsorption science and technology. A synthesis method of a high-water vapor adsorption polyion liquid adsorbent is characterized by realizing the preparation of the solid polyion liquid adsorbent with high-water vapor adsorption capacity through four steps of ionization, ion replacement, polymerization and product purification. Different from the existing polyion liquid, the polyion liquid monomer has a short carbon chain and acetic acid anions which are repeatedly arranged, has high water vapor adsorption capacity, and can be widely applied to the fields of drying, dehumidification, adsorption heat storage, seawater desalination by an adsorption method, sewage treatment and the like. The polyion liquid adsorbent is used as a porous solid, overcomes the defects of easy leakage, easy pollution, easy flowing and the like of the ionic liquid, and is suitable for large-scale industrial application.
Description
Technical Field
The invention relates to a synthesis method of a high-water vapor adsorption polyion liquid adsorbent, belonging to the field of adsorption science and technology.
Background
Steam adsorption is an important problem in the fields of drying, seawater desalination, adsorption heat storage and the like, and development of an adsorbent having high steam adsorption capacity is a main target in these fields. Traditional adsorbents such as silica gel, molecular sieves, inorganic hydrated salts, metal organic frameworks and ionic liquids show excellent water vapor adsorption and heat storage performances in some aspects, but the development and practical application of the traditional adsorbents are greatly limited by inherent defects, so that a novel efficient water vapor adsorbent system is urgently needed.
Ionic liquids are organic salts consisting of anions and cations and exhibiting a molten state below 100 ℃, and are considered as one of the "most potential new materials in the future" by the medium. The ionic liquid has structure adjustability, can be synthesized into the ionic liquid with specific functions by introducing functional groups with specific properties, and most of the hydrophilic ionic liquid and the hydrophobic ionic liquid have extremely strong water absorbability, and the ionic liquid has good thermal stability and environmental friendliness. Although the ionic liquid has higher water vapor adsorption capacity, the ionic liquid has high viscosity and small contact area with water vapor, reduces the heat and mass transfer rate and even the adsorption rate in an ionic liquid system, and the liquid form of the ionic liquid is easy to form a mixture with other substances and is difficult to separate.
The polyionic liquid is a solid polymer material formed by polymerizing unsaturated ionic liquid monomers, and is used in polymer electrolyte and CO 2 The method has important application value and wide application prospect in the fields of adsorption, catalysis, electric conduction, microwave absorption and the like. The polyion liquid not only has chemical stability, thermal stability, high conductivity and structural adjustability similar to those of the ionic liquid, but also shows inherent mechanical stability, flexibility and pore structure adjustability of the polymer, can overcome the defects of low water vapor adsorption capacity and easiness in leakage of the traditional ionic liquid adsorbent, and is very hopefully applied to the development of a novel efficient water vapor adsorption technology.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a method for synthesizing an ionic liquid adsorbent by adsorbing and agglomerating high water vapor, and aims to provide a method for synthesizing the ionic liquid adsorbent.
The technical scheme of the invention is as follows:
a synthesis method of a high-water vapor adsorption polyion liquid adsorbent mainly comprises the following steps:
(1) Ionization: preparing a halogenated 1-vinyl-3-methylimidazole ionic liquid by taking N-vinylimidazole and liquefied monohalomethane as raw materials through a quaternization reaction, wherein the molar ratio of the N-vinylimidazole to the liquefied monohalomethane is 0.80-1, the reaction temperature is 50-100 ℃, and the reaction time is 4-12 hours;
(2) Ion replacement: adding ammonium acetate into halogenated 1-vinyl-3-methylimidazole ionic liquid, and obtaining 1-vinyl-3-methylimidazole acetate ionic liquid through ion exchange reaction, wherein the molar ratio of the halogenated 1-vinyl-3-methylimidazole ionic liquid to the ammonium acetate is 0.85-1, the reaction temperature is 30-80 ℃, and the reaction time is 1-6 hours;
(3) Polymerization: dissolving acetic 1-vinyl-3-methylimidazole ionic liquid in dimethylformamide, adding azobisisobutyronitrile, and synthesizing the acetic 1-vinyl-3-methylimidazole ionic liquid into the acetic 1-vinyl-3-methylimidazole ionic liquid through polymerization, wherein the mass ratio of the dimethylformamide in a reaction system is 10-50% and the mass ratio of the azobisisobutyronitrile is 0.5-2%;
(4) Product purification: soaking the product obtained in the step (3) in ethanol for 2-6 hours to ensure that the ethanol just exceeds the product, replacing impurities such as dimethylformamide, azobisisobutyronitrile and the like in the product with the ethanol, then filtering, continuing the operation for 2 times on the obtained solid, and then drying the filtered solid at 50-100 ℃ for 4-8 hours to completely remove residual ethanol to obtain pure polyacetylated 1-vinyl-3-methylimidazole ionic liquid.
Wherein the monohalomethane comprises one of monochloromethane, monobromomethane and monoiodomethane.
Wherein the polymerization reaction in step (3) can be carried out by microwave polymerization, ultraviolet polymerization, thermal polymerization, or the likeThe mode is that the ultraviolet polymerization condition is 25 ℃, the effective ultraviolet wavelength is 365nm, the power is 6-12W, and the ultraviolet light intensity is 200-600mW/cm 2 The ultraviolet polymerization time is 60-240min; the microwave polymerization conditions are that the microwave power is 100-400W, the microwave radiation time is 60-120s, and the microwave radiation program is started and stopped alternately for 5-10 s; the thermal polymerization condition is heating at 60-100 deg.C for 120-240min.
Wherein, the molar ratio of acetic acid anion to 1-vinyl-3-methylimidazole cation in the polyacetylated 1-vinyl-3-methylimidazole ionic liquid prepared according to the technical scheme of the invention is 0.95-1.0, and the purity of the polyacetylated 1-vinyl-3-methylimidazole ionic liquid product is more than 90%.
The invention has the following effects and benefits: a synthesis method of a high-water vapor adsorption polyion liquid adsorbent is characterized by realizing the preparation of the solid polyion liquid adsorbent with high-water vapor adsorption capacity through four steps of ionization, ion replacement, polymerization and product purification. Different from the existing polyion liquid, the polyion liquid monomer has a short carbon chain and acetic acid anions which are repeatedly arranged, has high water vapor adsorption capacity, and can be widely applied to the fields of drying, dehumidification, adsorption heat storage, seawater desalination by an adsorption method, sewage treatment and the like. The polyion liquid adsorbent is used as a porous solid, overcomes the defects of easy leakage, easy pollution, easy flowing and the like of the ionic liquid, and is suitable for large-scale industrial application.
Detailed Description
The following technical scheme further illustrates the specific implementation mode of the invention.
Example 1
A synthesis method of a high-water vapor adsorption polyion liquid adsorbent mainly comprises the following steps:
(1) Ionization: 1 mol (94.12 g) of N-vinylimidazole and 1 mol (50.49 g) of liquefied monochloromethane are taken as raw materials, and the chlorinated 1-vinyl-3-methylimidazole ionic liquid is prepared through quaternization reaction at the reaction temperature of 80 ℃ for 8 hours;
(2) Ion replacement: adding 1 mol (77.08 g) of ammonium acetate into the obtained 1-vinyl-3-methylimidazole chloride ionic liquid, and carrying out ion exchange reaction to obtain 1-vinyl-3-methylimidazole acetate ionic liquid, wherein the reaction temperature is 70 ℃, and the reaction time is 3 hours;
(3) Polymerization: dissolving the obtained acetic acid 1-vinyl-3-methylimidazole ionic liquid (about 170 g) in 114g of dimethylformamide, adding 1.43g of azobisisobutyronitrile, and synthesizing the acetic acid 1-vinyl-3-methylimidazole ionic liquid into the acetic acid 1-vinyl-3-methylimidazole ionic liquid through polymerization reaction, wherein the polymerization method adopts a thermal polymerization method, the thermal polymerization condition is heating at 80 ℃ for 180min, and the mass ratio of the dimethylformamide in the reaction system is 40% and the mass ratio of the azobisisobutyronitrile is 0.5%;
(4) Product purification: and (4) soaking the product obtained in the step (3) in 300g of ethanol for 4 hours to ensure that the ethanol just exceeds the product, replacing impurities such as dimethylformamide, azodiisobutyronitrile and the like in the product with the ethanol, filtering, continuing the operation for 2 times on the obtained solid, and drying the filtered solid at 80 ℃ for 6 hours to completely remove residual ethanol to obtain the pure polyacetylated 1-vinyl-3-methylimidazole ionic liquid.
The molar ratio of acetate anion to 1-vinyl-3-methylimidazole cation in the polyacetylated 1-vinyl-3-methylimidazole ionic liquid product prepared according to this example was 0.99, and the purity of the polyacetylated 1-vinyl-3-methylimidazole ionic liquid product was 98%.
The water vapor adsorption capacity of the polyacetylated 1-vinyl-3-methylimidazole ionic liquid is tested by using a dynamic vapor adsorption instrument under the test condition of 25 ℃, and the saturated adsorption capacity of the polyacetylated 1-vinyl-3-methylimidazole ionic liquid prepared in the embodiment under the relative humidity of 90% is 1.26g/g.
Example 2
A synthesis method of a high-water vapor adsorption polyion liquid adsorbent mainly comprises the following steps:
(1) Ionization: preparing brominated 1-vinyl-3-methylimidazole ionic liquid by quaternization reaction at the temperature of 60 ℃ for 10 hours by using 0.5 mol (47.06 g) of N-vinylimidazole and 0.5 mol (47.47 g) of liquefied monobromomethane as raw materials;
(2) Ion replacement: adding 0.5 mol (38.54 g) of ammonium acetate into the obtained brominated 1-vinyl-3-methylimidazole ionic liquid, and carrying out ion replacement reaction to obtain the acetic acid 1-vinyl-3-methylimidazole ionic liquid, wherein the reaction temperature is 40 ℃, and the reaction time is 5 hours;
(3) Polymerization: dissolving the obtained acetic acid 1-vinyl-3-methylimidazole ionic liquid (about 85 g) in 21.8g of dimethylformamide, adding 2.18g of azodiisobutyronitrile, and synthesizing the acetic acid 1-vinyl-3-methylimidazole ionic liquid into the acetic acid 1-vinyl-3-methylimidazole ionic liquid through polymerization reaction by adopting an ultraviolet polymerization method, wherein the polymerization method adopts an ultraviolet polymerization method, the ultraviolet polymerization condition is 25 ℃, the effective ultraviolet wavelength is 365nm, the power is 8W, and the ultraviolet light intensity is 400mW/cm 2 The ultraviolet polymerization time is 180min, wherein the mass ratio of dimethylformamide in the reaction system is 20 percent, and the mass ratio of azobisisobutyronitrile is 2 percent;
(4) Product purification: and (4) soaking the product obtained in the step (3) in 150g of ethanol for 4 hours to ensure that the ethanol just exceeds the product, replacing impurities such as dimethylformamide, azodiisobutyronitrile and the like in the product with the ethanol, filtering, continuing the operation for 2 times on the obtained solid, and drying the filtered solid at 60 ℃ for 8 hours to completely remove residual ethanol to obtain the pure polyacetylated 1-vinyl-3-methylimidazole ionic liquid.
The molar ratio of acetate anion to 1-vinyl-3-methylimidazole cation in the polyacetylated 1-vinyl-3-methylimidazole ionic liquid product prepared according to this example was 0.96, and the purity of the polyacetylated 1-vinyl-3-methylimidazole ionic liquid product was 95%.
The dynamic steam adsorption instrument is utilized to test the water vapor adsorption capacity of the polyacetylated 1-vinyl-3-methylimidazole ionic liquid, the test condition is 25 ℃, and the saturated adsorption capacity of the polyacetylated 1-vinyl-3-methylimidazole ionic liquid prepared in the embodiment at 90% relative humidity is 1.18g/g.
Claims (8)
1. A synthesis method of a high-water vapor adsorption polyion liquid adsorbent is characterized by comprising the following steps:
(1) Ionization: taking N-vinylimidazole and liquefied monohalomethane as raw materials, preparing halogenated 1-vinyl-3-methylimidazole ionic liquid through quaternization, wherein the molar ratio of the N-vinylimidazole to the liquefied monohalomethane is 0.80-1, and the reaction temperature is 50-100 o C, the reaction time is 4-12 hours;
(2) Ion replacement: adding ammonium acetate into halogenated 1-vinyl-3-methylimidazole ionic liquid, and obtaining the 1-vinyl-3-methylimidazole acetate ionic liquid through ion exchange reaction, wherein the molar ratio of the halogenated 1-vinyl-3-methylimidazole ionic liquid to the ammonium acetate is 0.85-1, and the reaction temperature is 30-80 o C, the reaction time is 1-6 hours;
(3) Polymerization: synthesizing the acetoxylated 1-vinyl-3-methylimidazole ionic liquid into the polyacetoxylated 1-vinyl-3-methylimidazole ionic liquid through polymerization reaction;
(4) Product purification: and (4) soaking the product obtained in the step (3) in ethanol, and then filtering and drying to obtain the pure polyacetylated 1-vinyl-3-methylimidazole ionic liquid.
2. The method of claim 1, wherein the monohalomethane comprises one or more of monochloromethane, monobromomethane, and iodomethane.
3. The synthesis method according to claim 1, wherein the polymerization reaction in step (3) utilizes one or more of microwave polymerization, ultraviolet polymerization and thermal polymerization;
UV polymerization conditions were 25 o C, the effective ultraviolet wavelength is 365nm, the power is 6-12W, and the intensity of the ultraviolet light is 200-600mW/cm 2 The ultraviolet polymerization time is 60-240min;
the microwave polymerization conditions are that the microwave power is 100-400W, the microwave radiation time is 60-120s, and the microwave radiation program is that 5-10s start and stop are alternately carried out;
the thermal polymerization condition is heating at 60-100 deg.C for 120-240min.
4. The synthesis method according to claim 1, wherein the molar ratio of acetate anion to 1-vinyl-3-methylimidazole cation in the prepared polyacetylated 1-vinyl-3-methylimidazole ionic liquid product is 0.95-1.0, and the purity of the polyacetylated 1-vinyl-3-methylimidazole ionic liquid product is more than 90%.
5. The method of synthesis according to claim 1,
dissolving the acetic acid 1-vinyl-3-methylimidazole ionic liquid in dimethylformamide, adding azobisisobutyronitrile, and synthesizing the acetic acid 1-vinyl-3-methylimidazole ionic liquid into the poly acetic acid 1-vinyl-3-methylimidazole ionic liquid through polymerization, wherein the mass ratio of the dimethylformamide in a reaction system is 10-50% and the mass ratio of the azobisisobutyronitrile is 0.5-2%.
6. The synthesis method according to claim 1, wherein the product of the step (4) is purified: soaking the product obtained in the step (3) in ethanol for 2-6 hours to ensure that the ethanol just exceeds the product, replacing impurities of dimethylformamide and azobisisobutyronitrile in the product by the ethanol, then filtering, continuing the operation for 2 times on the obtained solid, and then filtering to obtain a solid with the content of 50-100 percent o And C, drying for 4-8 hours to completely remove residual ethanol to obtain pure polyacetylated 1-vinyl-3-methylimidazole ionic liquid.
7. A polyacetylated imidazolyl ionic liquid obtained by the synthesis process of any one of claims 1 to 6.
8. Use of the polyacetylated imidazolyl ionic liquid of claim 7 as an adsorbent for water vapor adsorption.
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| US8734673B2 (en) * | 2008-08-08 | 2014-05-27 | The University Of Toledo | Boron selective ionic liquids and polymeric ionic liquids, methods of making and methods of use thereof |
| US20120134905A1 (en) * | 2009-06-25 | 2012-05-31 | Vtu Holding Gmbh | Method of use of an ionic liquid and device for sorption of a gas |
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| CN101337938A (en) * | 2007-07-04 | 2009-01-07 | 中国纺织科学研究院 | Method for synthesizing acetate ionic liquid |
| CN108273477A (en) * | 2018-02-07 | 2018-07-13 | 厦门大学 | A kind of porous poly ion liquid adsorbent and its application |
| CN109092265A (en) * | 2018-09-10 | 2018-12-28 | 陕西科技大学 | A kind of Studies On Preparation And Properties of Cellulose-based Adsorbents and its preparation method and application that polyimidazole is ion liquid modified |
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