KR20110080004A - Carbon dioxide absorbents using the imidazolium-based ionic liquid compound comprising fluorinated olefin - Google Patents

Abstract

PURPOSE: A carbon dioxide absorbent using imidazolium ionic liquid compounds containing fluorinated olefin is provided to ensure thermal stability and excellent carbon dioxide absorption ability. CONSTITUTION: An imidazolium ionic liquid compound containing fluorinated olefin with carbon dioxide absorption ability is denoted by chemical formula 1. A method for preparing the imidazolium ionic liquid compound comprises: a step of reacting Brensted acid with 1,2-dialkylimidazole of chemical formula 2 under the presence of an organic solvent to form a salt; and a step of adding fluorinated olefin gas to the salt. Brensted acid is HCl, CF_3CO_2H, CH_3CO_2H, HBF_4, (CF_3SO_2)_2NH, or CF_3SO_3H. The organic solvent is tetrahydrofuran.

Description

Carbon dioxide absorbents using the imidazolium-based ionic liquid compound comprising fluorinated olefins

The present invention relates to a carbon dioxide absorbent using an imidazolium-based ionic liquid compound containing a fluorine-containing olefin having a carbon dioxide absorption capacity.

Absorption, adsorption, separation membrane, deep cooling, etc. are used to separate carbon dioxide from exhaust gas and natural gas of chemical plants, power plants, and large boilers. In particular, when the concentration of carbon dioxide emitted is low, absorption or adsorption methods are frequently used. The absorption method or the adsorption method can be selectively separated only some of the gas that is absorbed or adsorbed to the absorbent or the adsorbent is widely used industrially, but there is a disadvantage that the periodic replacement is necessary because the absorbent and the adsorbent are chemically modified during the separation process. . In the case of using a solid adsorbent, it is advantageous to apply it when the adsorbent replacement cycle is long due to the small chemical deformation of the adsorbent. On the other hand, the absorption method uses a liquid absorbent, which makes it easy to replace the absorbent. Although widely used for gas separation, there is a disadvantage in that the absorbent is chemically modified.

As carbon dioxide absorbers, amines such as monoethanolamine (MEA), N-methyldiethanolamine (NDEA), and diethanolamine (DEA) are most widely used. This is because alkaline amine absorbents form a chemical bond with carbon dioxide, an acidic gas, and when heated, the bond is broken and carbon dioxide is degassed and recovered and the absorbent can be regenerated.

However, this process has some serious problems. Specifically, the problem of decomposition of the amine by impurities such as SOx and NOx contained in the absorbent gas, the irreversible decomposition of the amine by the high temperature used to break the chemical bond between the carbon dioxide and the absorbent in the regeneration step of the absorbent, the amine Problems such as deterioration of absorbent performance due to irreversible decomposition and replenishment of absorbent, corrosion of absorber by amine itself or decomposition products, contamination of regenerated gaseous carbon dioxide by vapor pressure of absorbent, etc. are pointed out as disadvantages.

In order to compensate for the disadvantages of the amine-based aqueous solution absorbents, methods for physically absorbing carbon dioxide using organic solvents such as selexol, IFPexol, and NFM have been reported. The most important point of the organic solvent absorbent is that carbon dioxide absorption requires much lower energy for carbon dioxide recovery and solvent regeneration because the carbon dioxide absorption is achieved only by the physical interaction between the solvent and the carbon dioxide, not the chemical bond as in the aqueous amine solution. In practice, when amine absorbers are used, carbon dioxide recovery and absorbent regeneration require energy-intensive high temperature stripping processes, but in the case of physical absorption, carbon dioxide dissolved in the solvent can be recovered simply by changing the pressure without raising the temperature. Can be. However, the physical absorption process also has the following disadvantages.

(1) Low CO2 Absorption Capacity: Organic solvents generally exhibit much lower CO2 absorption capacity than amine aqueous solutions, so the circulation rate of the absorbent is high and therefore a larger device is needed.

(2) High circulation rate: The physical absorption process by organic solvents usually requires more than twice the absorbent circulation rate compared with the amine solution, which requires more capital and equipment costs.

(3) Loss of Solvent: Solvents used for physical absorption do not have high boiling point and tend to be lost during the absorption and regeneration process. This solvent loss can be minimized through cooling or washing, but has the disadvantage of requiring additional equipment installation costs.

Therefore, there has been a need for the development of new absorbents that can overcome the disadvantages of amine absorbers and organic solvent absorbers.

In order to overcome the shortcomings of the recent absorbents, US Patent No. 6,849,774, US Patent No. 6,623,659 and US Patent Publication No. 2008/0146849 have no volatility and high thermal stability while maintaining a liquid phase at a temperature below 100 ° C. It is known to use ionic liquids as absorbents. Ionic liquids are polar salt compounds composed of organic cations and organic or inorganic anions and have a property of dissolving gas molecules such as CO, CO ₂ , SO ₂ , and N ₂ O well. The solubility of the gas absorbed in the ionic liquid depends on the degree of interaction between the gas and the ionic liquid, and therefore the polarity, acidity, and basicity of the ionic liquid can be modified by appropriately modifying the cations and anions of the ionic liquid. Changes in basicity, nucleophilicity, etc., can control the solubility of certain gases to some extent.

Typical ionic liquids include quaternary ammonium, that is, imidazolium, pyrazolium, triazolium, pyridinium, pyridinium Dodge titanium, pyrimidinyl titanium, organic cations containing nitrogen, and Cl ^-, Br ^-, I ^- halogens, such as _{^{, BF 4 -, PF 6 -}} , (CF 3 SO 2) 2 N -, CF 3 SO 3 -, MeSO 3 -, NO 3 -, CF 3 CO 2 -, CH 3 CO 2 - consisting of the anions such as Compounds are known and have been reported to have relatively high carbon dioxide absorption, especially when anions contain fluorine atoms. However, these ionic liquid absorbents also have a significantly lower carbon dioxide absorption ability than the amine absorbents, or are vulnerable to moisture and decomposed by moisture contained in the mixed gas, thereby gradually reducing the absorption capacity or excessively high manufacturing cost, thereby reducing economic efficiency. have.

In particular, tetrafluoroborate (BF ₄ ^-), hexafluorophosphate (PF ₆ ^-), trifluoromethyl sulfonimide _{(CF 3 SO 2) 2 N} -) an ionic liquid having an anion containing a fluorine atom and the like are Although it has a relatively high solubility in acidic gases such as carbon dioxide and carbon disulfide, the synthesis of these ionic liquids usually requires two or more complex manufacturing processes, and the manufacturing costs are too high for industrial use. .

Accordingly, the present inventors have studied diligently to solve the problems of the conventional organic solvent absorbent, and as a result, the imidazole including fluorine-containing olefin obtained by reacting 1,2-dialkylimidazole compound, brested acid and fluorine-containing olefin The cerium-based ionic liquid compound has a high thermal and chemical stability while having a high absorption capacity to carbon dioxide, has a low viscosity, as well as easy to synthesize and found the present invention.

An object of the present invention is to provide an imidazolium-based ionic liquid compound containing a fluorine-containing olefin having a carbon dioxide absorption capacity.

Another object of the present invention to provide a method for producing an imidazolium-based ionic liquid compound containing the fluorine-containing olefin.

Another object of the present invention to provide a carbon dioxide absorbent comprising an imidazolium-based ionic liquid compound containing the fluorine-containing olefin.

Another object of the present invention is to provide a method for separating carbon dioxide from a gas mixture using a carbon dioxide absorbent comprising an imidazolium-based ionic liquid compound containing the fluorine-containing olefin.

In order to achieve the above object, the present invention provides an imidazolium-based ionic liquid compound containing a fluorine-containing olefin represented by the following formula (1).

[Formula 1]

(In Formula 1, R ¹ and R ² are C ₁ ~ C ₆ linear or branched alkyl, R ³ is H, F or CF ₃ , X is Cl, CF ₃ CO ₂ , CH ₃ CO ₂ , BF ₄ , (CF ₃ SO ₂ ) ₂ N or CF ₃ SO _3. )

The present invention also provides a method for producing an imidazolium-based ionic liquid compound including the fluorine-containing olefin of the formula (1).

Furthermore, the present invention provides a carbon dioxide absorbent comprising an imidazolium-based ionic liquid compound including the fluorine-containing olefin of Formula 1.

The present invention also provides a method for separating carbon dioxide from a gas mixture using a carbon dioxide absorbent comprising an imidazolium-based ionic liquid compound containing a fluorine-containing olefin of the formula (1).

The imidazolium-based ionic liquid compound including the fluorine-containing olefin according to the present invention has a very low vapor pressure, excellent thermal and chemical stability, excellent carbon dioxide absorption ability, and a relatively low temperature of desorbed carbon dioxide. It can be carried out in, and can be effectively used as a carbon dioxide absorbent because there is almost no decrease in absorption capacity even when repeated use can maintain the initial absorption capacity even when repeated absorption and degassing.

1 is a schematic diagram of a carbon dioxide absorption experiment apparatus.
Figure 2 is a graph showing the absorption rate of carbon dioxide during carbon dioxide adsorption and desorption repeated experiments of the imidazolium-based ionic liquid compound containing a fluorine-containing olefin according to an embodiment of the present invention.

EMBODIMENT OF THE INVENTION Hereinafter, this invention is demonstrated in detail.

The present invention provides an imidazolium-based ionic liquid compound including a fluorine-containing olefin represented by the following formula (1).

(In Formula 1, R ¹ and R ² are C ₁ ~ C ₆ linear or branched alkyl, R ³ is H, F or CF ₃ , X is Cl, CF ₃ CO ₂ , CH ₃ CO ₂ , BF ₄ , (CF ₃ SO ₂ ) ₂ N or CF ₃ SO _3. )

The imidazolium-based ionic liquid compound including the fluorine-containing olefin of Formula 1 may be selected from the group consisting of the following compounds:

,

,

,

,

,

,

,

및

.

,

,

,

And

.

The imidazolium-based ionic liquid compound including the fluorine-containing olefin of Formula 1 has a low viscosity while maintaining a liquid phase at room temperature.

In addition, the present invention comprises the steps of forming a salt by reacting 1,2-dialkylimidazole represented by the following formula (2) and Brenstead acid in an organic solvent (step 1); And

Fluorine-containing fluorine of Formula 1 comprising the step (step 2) to obtain a imidazolium-based ionic liquid compound containing a fluorine-containing olefin represented by the formula (1) by adding a fluorine-containing olefin gas to the salt produced in step 1 It provides a method for producing an imidazolium-based ionic liquid compound containing an olefin.

(In Formula 2, R ¹ and R ² are C ₁ to C ₆ linear or branched alkyl.)

The compounds according to the present invention can be obtained by reacting 1,2-dialkylimidazole with brested acid and fluorine-containing olefins, and various types of 1,2-dialkylimidazole compounds, brendsteadic acid and By combining the fluorine-containing olefins, an imidazolium-based ionic liquid compound containing various kinds of fluorine-containing olefins can be obtained.

In this case, the brendsteadic acid may be HCl, CF ₃ CO ₂ H, CH ₃ CO ₂ H, HBF ₄ , (CF ₃ SO ₂ ) ₂ NH, CF ₃ SO ₃ H and the like, the fluorinated olefin is CF ₃ CF = CF ₂ , CF ₂ = CF ₂ , CF ₂ = CHF and the like can be used.

In the production method according to the present invention, the organic solvent is preferably tetrahydrofuran (THF), but is not limited thereto.

In the case of step 1, the reaction may be performed at room temperature and atmospheric pressure for 1 to 3 hours. For step 2, the reaction may be performed at room temperature and 1 to 50 atmospheres for 5 to 36 hours.

Furthermore, the present invention provides a carbon dioxide absorbent using an imidazolium-based ionic liquid compound including the fluorine-containing olefin of Formula 1.

When the imidazolium-based ionic liquid compound including the fluorine-containing olefin according to the present invention is used as the carbon dioxide absorbent, the energy consumed in the degassing process of the absorbed carbon dioxide is much smaller than that of the amine absorbent, This is because it is much easier to remove carbon dioxide from the ionic liquid compound in which carbon dioxide is absorbed by physical interaction than in the amine solution to which it is bound.

In addition, the imidazolium-based ionic liquid compound including the fluorine-containing olefin according to the present invention shows a much higher carbon dioxide absorption capacity than the organic solvent absorbent. This is because F atoms with a high electronegativity in the imidazolium-based ionic liquid compound molecule including the fluorine-containing olefin can interact with oxygen atoms of carbon dioxide. Therefore, when the imidazolium-based ionic liquid compound including the fluorine-containing olefin according to the present invention is used as the absorbent, the circulation rate of the absorbent can be lowered compared to the organic solvent absorbent, thereby significantly reducing the size of the device. Furthermore, since the imidazolium-based ionic liquid compound including the fluorine-containing olefin according to the present invention has a very low absorption rate of hydrocarbons compared to the organic solvent absorbent, only carbon dioxide is selectively absorbed when used in hydrocarbon purification such as natural gas containing carbon dioxide impurities. Therefore, the loss of the target hydrocarbon can be minimized.

In addition, when the imidazolium-based ionic liquid compound containing a fluorine-containing olefin according to the present invention is used as a carbon dioxide absorbent, there is almost no loss of the absorbent. Since the imidazolium-based ionic liquid compound including fluorine-containing olefins used in the present invention has a very low vapor pressure, the possibility of the loss of the carbon dioxide absorbent is very small, and since it is chemically stable, the loss of the carbon dioxide absorbent by decomposition is also very low. .

Imidazolium-based ionic liquid compound containing a fluorine-containing olefin of the formula (1) according to the present invention shows a carbon dioxide absorption amount of more than 0.3 mole fraction in the carbon dioxide absorption experiment to compare 1-butyl-3-methylimidazolium tetrafluoroborate (carbon dioxide) Absorption amount: 0.15 mole fraction) or 1-ethyl-3-methylimidazolium ethyl sulfate (carbon dioxide absorption amount: 0.08 mole fraction) was found to absorb about two times more carbon dioxide (see Table 2). In addition, in the reuse experiment, the imidazolium-based ionic liquid compound including the fluorine-containing olefin according to the present invention had an absorption equilibrium of about 200 seconds even when repeated five absorption-degassing experiments. It was not observed that it was possible to reuse (see Figure 2).

Therefore, the imidazolium-based ionic liquid compound including the fluorine-containing olefin according to the present invention not only possesses excellent carbon dioxide absorption ability, but also can perform degassing of absorbed carbon dioxide at a relatively low temperature, There is little reduction and can be effectively used as a carbon dioxide absorbent.

In this case, the carbon dioxide absorbent may include at least one imidazolium-based ionic liquid compound including the fluorine-containing olefin.

In addition, the present invention comprises the steps of absorbing carbon dioxide using a carbon dioxide absorbent comprising an imidazolium-based ionic liquid compound including a fluorine-containing olefin of the formula (1) in the gas mixture (step 1); And

It provides a method of separating the carbon dioxide from the gas mixture comprising the step of degassing the carbon dioxide absorbed by the carbon dioxide absorbent (step 2).

In the method for separating carbon dioxide from the gas mixture according to the present invention, the preferred temperature at the time of absorbing carbon dioxide is in the range of 0 ° C to 80 ° C, more preferably in the range of 20 ° C to 50 ° C, and the preferred pressure is from atmospheric pressure to 60 atmospheres. Range. When absorbing carbon dioxide, the lower the temperature and the higher the pressure, the higher the amount of carbon dioxide absorbed. In particular, as the pressure increases, the amount of carbon dioxide absorbed increases almost linearly (see Tables 2 and 3).

In the method for separating carbon dioxide from the gas mixture according to the present invention, the preferred temperature for degassing the absorbed carbon dioxide is in the range of room temperature to 100 ° C, more preferably in the range of 40 to 80 ° C, and the preferred pressure is atmospheric pressure.

In the method for separating carbon dioxide from the gas mixture according to the present invention, the gas mixture may be exhaust gases, natural gas, etc. discharged from chemical plants, power plants, large boilers, and the like.

Hereinafter, the present invention will be described in more detail by the following examples. However, the following examples merely illustrate the present invention, and the contents of the present invention are not limited by the following examples.

< Example  1 ~ 7> Fluorinated olefins  inclusive Imidazolium Ionic Liquid  Synthesis of Compound

 Tetrahydrofuran (THF) was added to a 100 mL stainless steel high pressure reactor equipped with a pressure gauge and a temperature controller, and 1,2-dialkylimidazole and brested acid were reacted at room temperature for 1 hour to prepare a salt. . The salt and the fluorine-containing olefin were reacted for 24 hours at room temperature and 4 atm pressure. After the reaction was completed, the solvent contained in the product was removed under vacuum to obtain an imidazolium-based ionic liquid compound containing a liquid fluorine-containing olefin.

The obtained ionic liquid was confirmed its structure by LC-Mass and NMR.

The imidazolium-based ionic liquid compound including the kind of imidazole, brested acid and fluorine-containing olefins and the resulting fluorine-containing olefins used in the synthesis are summarized in Table 1 below.

Example Imidazole Brested acid Olefin Ionic liquid compound produced One 1-ethyl-2-methyl imidazole CF ₃ CO ₂ H CF ₃ CF = CF ₂

2 1-butyl-2-methyl imidazole CH ₃ CO ₂ H CF ₃ CF = CF ₂

3 1-hexyl-2-methyl imidazole HCl CF ₃ CF = CF ₂

4 1,2-dimethyl imidazole CF ₃ SO ₂ H CF ₃ CF = CF ₂

5 1,2-dimethyl imidazole (CF ₃ SO ₂ ) ₂ NH CF ₃ CF = CF ₂

6 1,2-dimethyl imidazole BF ₄ CF ₂ = CF ₂

7 1,2-dimethyl imidazole PF ₆ CE ₂ = CHF

< Comparative example  1 ~ 2>

1-Butyl-3-methylimidazolium tetrafluoroborate or 1-ethyl-3-methylimidazolium ethylsulfate was used as the carbon dioxide absorbent.

< Experimental Example  1> Carbon Dioxide Absorption Test

In order to determine whether the imidazolium-based ionic liquid compound including the fluorine-containing olefin according to the present invention can be used as a carbon dioxide absorbent, the following experiment was performed.

Specifically, carbon dioxide absorption performance experiments were performed using the apparatus of FIG. 1. The device of FIG. 1 is similar to that commonly used in physical absorption processes, with a 60 mL stainless steel absorption reactor (R1) with a thermometer (T2) attached, a pressure transducer (P1) for high pressure (0 to 1000 psi). ), Consisting of a 75 mL carbon dioxide storage cylinder (S2) and a stirrer (1) attached to the thermometer (T1), it is installed in a thermostat to measure the ability to absorb carbon dioxide at a certain temperature. In addition, the carbon dioxide supply container (S1) and the pressure gauge (P2) is provided outside the thermostat.

10 g of an imidazolium-based ionic liquid compound containing the fluorinated olefins of Examples 1 to 7 or the compound of Comparative Examples 1 to 2 was charged into the absorption reactor (R1) of FIG. 1, and the temperature of the thermostat was maintained at 25 ° C. . After filling the carbon dioxide with a certain pressure in the carbon dioxide storage cylinder (S2), open the valve (V4) to expand the carbon dioxide in the absorption reactor (R1) to adjust the initial pressure of the absorption reactor (R1) and the total system to 10 atm. The amount of carbon dioxide absorbed in the imidazolium-based ionic liquid compound including the fluorine-containing olefin is measured by measuring the degree to which the pressure of the carbon dioxide storage cylinder (S2) decreases until the absorption equilibrium is reached. Calculated. Intake experiments of carbon dioxide were carried out at 10 atm and room temperature, and degassing was performed by leaving the valve open at room temperature and atmospheric pressure for 30 minutes.

The mole fraction of carbon dioxide was calculated by the same method as in Equation 1 below.

The measurement results are shown in Table 2.

division Absorbing pressure
(atmospheric pressure) Absorption temperature
(℃) CO2 uptake
(Mole fraction) Example 1 10 25 0.32 Example 2 10 25 0.31 Example 3 10 25 0.31 Example 4 10 25 0.32 Example 5 10 25 0.34 Example 6 10 25 0.33 Example 7 10 25 0.30 Comparative Example 1 10 25 0.15 Comparative Example 2 10 25 0.08

As shown in Table 2, the imidazolium-based ionic liquid compound containing a fluorine-containing olefin according to the present invention exhibits a carbon dioxide absorption amount of 0.3 mole fraction or more, thereby comparing 1-butyl-3-methylimidazolium tetrafluoroborate (carbon dioxide). Absorption amount: 0.15 mole fraction) or 1-ethyl-3-methylimidazolium ethyl sulfate (carbon dioxide absorption amount: 0.08 mole fraction) was found to absorb about two times more carbon dioxide. Therefore, since the imidazolium-based ionic liquid compound including the fluorine-containing olefin according to the present invention has excellent carbon dioxide absorption ability, it can be usefully used as a carbon dioxide absorbent.

< Experimental Example  2> Carbon dioxide uptake test by temperature

In order to determine the change of carbon dioxide absorption according to the temperature of the imidazolium-based ionic liquid compound including the fluorine-containing olefin according to the present invention, the following experiment was performed.

Using the imidazolium-based ionic liquid compound containing a fluorine-containing olefin prepared in Example 1 as an absorbent, and the absorption pressure is fixed at 20 atm, while changing the absorption temperature as shown in Table 3 below the same as Experimental Example 1 Carbon dioxide absorption experiment was carried out by the method, the results are shown in Table 3.

division Absorbing pressure
(atmospheric pressure) Absorption temperature
(℃) CO2 uptake
(Mole fraction) Example 1 20 25 0.51 20 40 0.49 20 50 0.45 20 60 0.42

As shown in Table 3, the carbon dioxide absorption of the imidazolium-based ionic liquid compound including the fluorine-containing olefin according to the present invention decreases as the absorption temperature increases.

< Experimental Example  3> Carbon dioxide uptake test by initial pressure

In order to determine the change of carbon dioxide uptake according to the initial pressure of the imidazolium-based ionic liquid compound including the fluorine-containing olefin according to the present invention was carried out the following experiment.

Using an imidazolium-based ionic liquid compound containing a fluorine-containing olefin prepared in Example 1 as an absorbent, and the absorption temperature is fixed at 25 ℃, while changing the initial absorption pressure as shown in Table 4 and Experimental Example 1 Carbon dioxide absorption experiments were performed in the same manner, and the results are shown in Table 4.

division Absorbing pressure
(atmospheric pressure) Absorption temperature
(℃) CO2 uptake
(Mole fraction) Example 1 One 25 0.08 5 25 0.18 20 25 0.51

As shown in Table 4 and Figure 2, it can be seen that the carbon dioxide absorption of the imidazolium-based ionic liquid compound including the fluorine-containing olefin according to the present invention increases rapidly as the initial pressure of the carbon dioxide increases.

Therefore, by appropriately adjusting the initial pressure and the absorption temperature of the carbon dioxide can increase the carbon dioxide absorption amount of the imidazolium-based ionic liquid compound including the fluorine-containing olefin according to the present invention.

< Experimental Example  4> Fluorinated olefins  inclusive Imidazolium Ionic Liquid  Reuse Experiment of Compound

When reusing the imidazolium-based ionic liquid compound containing a fluorine-containing olefin according to the present invention to investigate the change of carbon dioxide absorption amount was carried out the following experiment.

The absorption temperature and pressure were fixed at 25 DEG C and 10 atm, respectively, and then the absorption and degassing were repeated five times in the same manner as in Experiment 1, using the imidazolium-based ionic liquid compound including the fluorinated olefin of Example 1 as an absorbent. And the result is shown in FIG.

As shown in FIG. 2, the absorption equilibrium of carbon dioxide reached about 200 seconds in 1 to 5 times, and no decrease in absorption capacity was observed even after repeated use.

Therefore, the imidazolium-based ionic liquid compound including the fluorine-containing olefin according to the present invention not only possesses excellent carbon dioxide absorption ability, but also can perform degassing of absorbed carbon dioxide at a relatively low temperature, There is little reduction and can be effectively used as a carbon dioxide absorbent.

S1: CO2 Container
S2: cylinder for storing carbon dioxide
R1: stainless steel absorption reactor
P1: pressure gauge
P2: pressure gauge
T1: thermometer
T2: thermometer
1: stirrer

Claims (16)

Imidazolium-based ionic liquid compound containing a fluorine-containing olefin having a carbon dioxide absorption capacity represented by the following formula (1):
[Formula 1]

(In Formula 1, R ¹ and R ² are C ₁ ~ C ₆ linear or branched alkyl, R ³ is H, F or CF ₃ , X is Cl, CF ₃ CO ₂ , CH ₃ CO ₂ , BF ₄ , (CF ₃ SO ₂ ) ₂ N or CF ₃ SO _3. )
The imidazolium-based ionic liquid compound according to claim 1, wherein the ionic liquid compound is selected from the group consisting of the following compounds:

,

,

,

,

,

And

.
Forming a salt by reacting 1,2-dialkylimidazole represented by the following Chemical Formula 2 with brensted acid under an organic solvent (step 1); And
The fluorine-containing olefin of claim 1 comprising the step (step 2) of obtaining an imidazolium-based ionic liquid compound containing a fluorine-containing olefin represented by the formula (1) by adding a fluorine-containing olefin gas to the salt produced in step 1 Method for producing an imidazolium-based ionic liquid compound containing.
(2)

(In Formula 2, R ¹ and R ² are C ₁ to C ₆ linear or branched alkyl.)

[Formula 1]

(In Formula 1, R ¹ and R ² are C ₁ ~ C ₆ linear or branched alkyl, R ³ is H, F or CF ₃ , X is Cl, CF ₃ CO ₂ , CH ₃ CO ₂ , BF ₄ , (CF ₃ SO ₂ ) ₂ N or CF ₃ SO _3. )
The method of claim 3, wherein the brendsteadic acid is selected from the group consisting of HCl, CF ₃ CO ₂ H, CH ₃ CO ₂ H, HBF ₄ , (CF ₃ SO ₂ ) ₂ NH, and CF ₃ SO ₃ H. A method for producing an imidazolium-based ionic liquid compound containing a fluorine-containing olefin.
The method of claim 3, wherein the fluorinated olefin is CF ₃ CF = CF ₂ , CF ₂ = CF ₂ And CF ₂ = CHF. A method for producing an imidazolium-based ionic liquid compound comprising a fluorine-containing olefin.
The method for producing an imidazolium-based ionic liquid compound according to claim 3, wherein the organic solvent is tetrahydrofuran.
The method of claim 3, wherein the reaction of Step 1 is carried out at room temperature and atmospheric pressure.
The method of claim 3, wherein the reaction of Step 2 is performed at room temperature and 1 to 50 atm.
Carbon dioxide absorbent comprising an imidazolium-based ionic liquid compound containing a fluorine-containing olefin of claim 1.
Absorbing carbon dioxide using the carbon dioxide absorbent of claim 9 in a gas mixture (step 1); And
Degassing the carbon dioxide absorbed by the carbon dioxide absorbent (step 2).
11. The method of claim 10, wherein the temperature at the time of absorbing carbon dioxide in step 1 is from 0 ° C to 80 ° C.
The method of claim 10, wherein the temperature at the time of absorbing carbon dioxide in step 1 is 20 ℃ to 50 ℃.
The method of claim 10, wherein the pressure when absorbing carbon dioxide in step 1 is from atmospheric pressure to 60 atm.
The method of separating carbon dioxide from a gas mixture according to claim 10, wherein the temperature when degassing the carbon dioxide in step 2 is from room temperature to 100 ° C.
The method of claim 10, wherein the temperature when degassing the carbon dioxide in step 2 is 40 ℃ to 80 ℃.
11. The method of claim 10, wherein the pressure when degassing carbon dioxide in step 2 is atmospheric pressure.

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