CN114460224A - Method for screening ionic liquid regenerated solvent based on thermodynamic property - Google Patents
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- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N25/00—Investigating or analyzing materials by the use of thermal means
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
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Abstract
The invention relates to the technical field of ionic liquid regeneration in an extraction separation process, and discloses a method for screening out a regenerated solvent of an ionic liquid based on thermodynamic properties of the ionic liquid and three-dimensional solubility parameters of a solvent to be selected. Firstly, Flory-Huggins interaction parameters between the ionic liquid and the organic solvent are measured according to a reverse gas chromatography technology, and the three-dimensional solubility parameters of the solvent to be selected are used for calculating the contribution values D, P and H of the dispersion solubility parameter, the polar solubility parameter and the hydrogen bond solubility parameter of the organic solvent to the total solubility parameter. And accurately screening out the solvent with good regeneration effect according to the distance between the organic solvent and the substance component to be separated in the component contribution diagram. The ionic liquid thermodynamic property and the three-dimensional solubility parameter of the substance to be separated established by the invention can accurately determine the solvent regenerated by the ionic liquid. The method has the characteristics of wide screening solvent, high practicability and strong universality, and has a guiding effect on production practice.
Description
Technical Field
The invention relates to the field of ionic liquid regeneration, and belongs to the technical field of screening of regenerated solvents in extraction separation based on thermodynamic properties of ionic liquids. .
Background
The ionic liquid is a salt substance which is in a liquid state at room temperature or at a temperature close to the room temperature, and the ionic liquid generally consists of organic cations and inorganic anions and has a plurality of characteristics: the liquid temperature range is wide and can reach hundreds of degrees; has high stability; the steam pressure is low and the steam is hardly volatilized; the ionic liquid has the properties similar to organic solvents, has good solubility for a plurality of organic matters and inorganic matters, has a plurality of types of anions and cations, and the properties of the ionic liquid can be adjusted by changing the structures of the cations or the anions. Therefore, theoretically, for any system or reaction, the corresponding functionalized ionic liquid can be synthesized. Due to these characteristics, ionic liquids are becoming a hot spot of research at home and abroad. At present, the method is widely applied to the fields of catalysis, electrochemistry, extraction separation and the like.
Based on the above advantages, ionic liquids are often used for extractive separation. For example, metal ions are extracted from waste water, benzene is extracted from alkanes, and phenol is extracted from kerosene. However, since ionic liquids are expensive, recovery and reuse of ionic liquids are extremely important in extraction and separation. The regeneration and reuse of ionic liquid are not involved in the prior extraction separation. The regeneration of ionic liquid is crucial to the perfection of the extraction process, and the methods for regenerating ionic liquid are various, and because the ionic liquid has the characteristics of zero vapor pressure, nonflammability and non-volatility, the kerosene has relatively low boiling point and strong volatility. Therefore, a typical regeneration method is to regenerate the ionic liquid by means of reduced pressure distillation. In the experiment of extracting phenol by using ionic liquid, in the method for separating the ionic liquid from phenol, neutral oil with a lower boiling point can be volatilized at first due to a lower distillation temperature, so that phenol with a relatively higher boiling point can be volatilized by raising the temperature, and the separation of the neutral oil, the phenol and the ionic liquid is finally realized. However, this method inevitably has many disadvantages. On one hand, the boiling point of phenol is relatively high, so that the time of reduced pressure distillation is too long, the cost is increased, and the phenol is not suitable for large-scale application; on the other hand, because of strong binding force between the ionic liquid and the phenol, the phenol cannot be completely separated from the ionic liquid even if the ionic liquid is distilled under reduced pressure, and the recycling of the ionic liquid is influenced.
Disclosure of Invention
The invention provides a regenerated solvent for screening out ionic liquid based on thermodynamic properties of the ionic liquid and three-dimensional solubility parameters of a solvent to be selected, and overcomes the defects of the prior art. The method can effectively solve the defects of reagent waste, poor practicability and universality in the existing method; the ionic liquid is applied to the regeneration of the ionic liquid in extraction separation, and the problems of relevant documents and reports are not found.
The technical scheme adopted by the invention is as follows:
the invention relates to the technical field of ionic liquid regeneration in extraction separation, in particular to a regenerated solvent for screening out ionic liquid based on thermodynamic properties of the ionic liquid and three-dimensional solubility parameters of a solvent to be selected; Flory-Huggins interaction parameters and infinite dilution activity coefficients between the ionic liquid and the organic solvent are measured according to a reverse gas chromatography technology, and are compared with the real dissolution situation of the ionic liquid in the solvent. And calculating the contribution values D, P and H of the dispersion solubility parameter, the polar solubility parameter and the hydrogen bond solubility parameter of the organic solvent to the total solubility parameter according to the three-dimensional solubility parameter of the solvent to be selected. Then, drawing the three-dimensional solubility parameters D, P and H of the solvent to be selected in a component contribution diagram containing the contribution value of the three-dimensional solubility parameter of the material component to be separated to the total solubility parameter; and the solvent with good regeneration effect can be accurately screened out according to the distance between the organic solvent and the substance component to be separated in the component contribution diagram. The method can quickly and accurately determine the solvents regenerated by different ionic liquids through the established ionic liquid thermodynamic properties and the three-dimensional solubility parameters of the solvents to be selected, greatly shortens the screening period compared with the traditional method, reduces the workload, saves the consumption of experimental materials, has the characteristics of wide screening solvent, high practicability and strong universality, improves the working efficiency, reduces the operation cost, and has a guiding function on production practice.
The following is further optimization or/and improvement of the technical scheme of the invention:
an extraction separation solvent screening method based on ionic liquid thermodynamic properties is characterized in that Flory-Huggins interaction parameters and infinite dilution activity coefficients between ionic liquid and an organic solvent are measured by combining reverse gas chromatography, and are compared with real dissolution conditions of five ionic liquids in the solvent, so that a common poor solvent of the five ionic liquids is selected; in addition, HSP of phenol and 49 organic solvents are found in a data simulation library, a triangular net graph is drawn, the spatial position distance between the phenol and the organic solvents is calculated, and the good solvent of the phenol is preferably selected by taking ether as a critical solvent. The ionic liquid is regenerated by combining a poor solvent of the ionic liquid with a good solvent of phenol, preferably by selecting several suitable stripping solvents.
Experimental procedure for ionic liquid regeneration: . (1) Adding ionic liquid with the oil agent ratio of 1.0 into 10 mL of phenol-toluene solution with the initial phenol concentration of 50 g/L at room temperature, stirring at 25 ℃ for 30 min, standing for 30 min, taking the upper layer solution, analyzing by gas chromatography, and separating the lower layer ionic liquid mixed phase by using a separating funnel for later use. (2) Adding the separated ionic liquid mixed phase into a round-bottom flask, adding excessive organic solvent, stirring at 30 deg.C for 60 min, separating the lower ionic liquid phase with a separating funnel, removing the organic solvent remained in the ionic liquid by distillation under reduced pressure, vacuum drying at 80 deg.C for 10 h to completely remove volatile components, and repeating the step three times. (3) The regenerated ionic liquid was added to 10 mL of a phenol-toluene solution having an initial phenol concentration of 50 g/L, stirred at 25 ℃ for 30 min, and then allowed to stand for 30 min, and the upper layer solution was taken out and analyzed by gas chromatography. (4) And performing infrared characterization on the ionic liquid before and after regeneration.
The ionic liquid used above is 1-allyl-3-methylimidazol [ AMIM ] Cl chloride, 1-allyl-3-ethylimidazol [ AEIM ] Cl chloride, 1-allyl-3-butylimidazolium [ ABIM ] Cl chloride, 1-allyl-3-methylimidazol [ AMIM ] Br bromide, 1-allyl-3-methylimidazol [ AMIM ] I iodide.
The invention relates to the technical field of ionic liquid regeneration in extraction separation, in particular to a regenerated solvent for screening out ionic liquid based on thermodynamic properties of the ionic liquid and three-dimensional solubility parameters of components to be separated; according to the thermodynamic property of the ionic liquid, Flory-Huggins interaction parameters and infinite dilution activity coefficients between the ionic liquid and the organic solvent are calculated through reverse gas chromatography measurement, and meanwhile, the contribution values D, P and H of polar solubility parameters and hydrogen bond solubility parameters of separated components to the total solubility parameter are calculated. Then, the contribution values D, P and H of the three-dimensional solubility parameter of the component to be separated to the total solubility parameter are drawn in a component contribution diagram containing the contribution values of the three-dimensional solubility parameter of the component of the substance to be separated to the total solubility parameter; and (3) quickly screening out the solvent with good ionic liquid regeneration effect according to the distance between the ionic liquid in the component contribution diagram and the substance component to be separated. The invention can quickly and accurately determine the solvents regenerated by different ionic liquids through the established component contribution diagram. Compared with the traditional method, the method greatly shortens the screening period, reduces the workload and saves the consumption of experimental materials. The method has the characteristics of wide screening solvent, high practicability and high universality, improves the working efficiency, reduces the operation cost and has a guiding effect on production practice.
Example 1: reuse of ionic liquids: (1) at room temperature, respectively adding four groups of 1-allyl-3 methylimidazole chloride with the oil ratio of 1.0 into 10 mL of phenol-toluene solution with the initial phenol concentration of 50 g/L, stirring at 25 ℃ for 30 min, standing for 30 min, taking the upper layer solution, analyzing by gas chromatography, and separating the lower ionic liquid mixed phase by using a separating funnel for later use. (2) Adding the separated first group of mixed phase of 1-allyl-3-methylimidazole chloride into a round-bottom flask, adding excessive diethyl ether, stirring at 30 ℃ for 60 min, separating the lower ionic liquid phase by using a separating funnel, removing the organic solvent remained in the ionic liquid by reduced pressure distillation, and drying at 80 ℃ for 10 h in vacuum to completely remove volatile components. (3) The regenerated ionic liquid was added to 10 mL of a phenol-toluene solution having an initial phenol concentration of 50 g/L, stirred at 25 ℃ for 30 min, and then allowed to stand for 30 min, and the upper layer solution was taken out and analyzed by gas chromatography. (4) And (3) repeating the step (2) twice, three times and four times on the separated mixed phase of the 1-allyl-3-methylimidazole chloride in the second group to the fourth group, and then performing the step (3) to detect the concentration of the phenol. The experimental method for regenerating the ionic liquid comprises the following steps: (1) 1-allyl-3-methylimidazole chloride having an oil ratio of 1.0 was added to 10 mL of a phenol-toluene solution having an initial phenol concentration of 50 g/L at room temperature. Stirring at 25 deg.C for 30 min, standing for 30 min, collecting the upper layer solution, analyzing with gas chromatography, and separating the lower layer ionic liquid mixed phase with separating funnel. (2) Adding the separated ionic liquid mixed phase into a round-bottom flask, adding excessive organic solvent, stirring at 30 deg.C for 60 min, separating the lower ionic liquid phase with a separating funnel, removing the organic solvent remained in the ionic liquid by distillation under reduced pressure, vacuum drying at 80 deg.C for 10 h to completely remove volatile components, and repeating the step three times. (3) The regenerated ionic liquid was added to 10 mL of a phenol-toluene solution having an initial phenol concentration of 50 g/L, stirred at 25 ℃ for 30 min, and then allowed to stand for 30 min, and the upper layer solution was taken out and analyzed by gas chromatography. (4) The chlorinated 1-allyl-3 methylimidazole before and after regeneration was subjected to infrared characterization.
Example 2: reuse of ionic liquids: (1) at room temperature, respectively adding four groups of 1-allyl-3 ethylimidazole chloride with the oil ratio of 1.0 into 10 mL of phenol-toluene solution with the initial phenol concentration of 50 g/L, stirring at 25 ℃ for 30 min, standing for 30 min, taking the upper layer solution, analyzing by using a gas chromatograph, and separating the lower ionic liquid mixed phase by using a separating funnel for later use. (2) Adding the separated first group of 1-allyl-3-ethylimidazole chloride mixed phase into a round-bottom flask, adding excessive diethyl ether, stirring at 30 ℃ for 60 min, separating the lower ionic liquid phase by using a separating funnel, removing the organic solvent remained in the ionic liquid by reduced pressure distillation, and completely removing volatile components by vacuum drying at 80 ℃ for 10 h. (3) The regenerated 1-allyl-3-ethylimidazole chloride was added to 10 mL of a phenol-toluene solution having an initial phenol concentration of 50 g/L, stirred at 25 ℃ for 30 min, and then allowed to stand for 30 min, and the upper layer solution was taken out and analyzed by gas chromatography. (4) And (3) repeating the step (2) twice, three times and four times on the mixed phase of the chlorinated 1-allyl-3-ethylimidazole separated out from the second group to the fourth group, and then performing the step (3) to detect the concentration of the phenol. Experimental method for regenerating ionic liquid: (1) adding 1-allyl-3 ethylimidazole chloride with an oil ratio of 1.0 into 10 mL of phenol-toluene solution with the initial phenol concentration of 50 g/L at room temperature, stirring at 25 ℃ for 30 min, standing for 30 min, taking the upper layer solution, analyzing by using a gas chromatograph, and separating the lower ionic liquid mixed phase by using a separating funnel for later use. (2) Adding the separated ionic liquid mixed phase into a round-bottom flask, adding excessive organic solvent, stirring at 30 deg.C for 60 min, separating the lower ionic liquid phase with a separating funnel, removing the organic solvent remained in the ionic liquid by distillation under reduced pressure, vacuum drying at 80 deg.C for 10 h to completely remove volatile components, and repeating the step three times. (3) The regenerated 1-allyl-3-ethylimidazole chloride was added to 10 mL of a phenol-toluene solution having an initial phenol concentration of 50 g/L, stirred at 25 ℃ for 30 min, and then allowed to stand for 30 min, and the upper layer solution was taken out and analyzed by gas chromatography. (4) Infrared characterization was performed on 1-allyl-3 ethylimidazole chloride before and after regeneration.
Experimental example 3: reuse of ionic liquids: (1) at room temperature, respectively adding four groups of 1-allyl-3-butylimidazole chloride with an oil ratio of 1.0 into 10 mL of phenol-toluene solution with an initial phenol concentration of 50 g/L, stirring at 25 ℃ for 30 min, standing for 30 min, taking the upper layer solution, analyzing by gas chromatography, and separating the lower ionic liquid mixed phase by using a separating funnel for later use. (2) Adding the separated first group of 1-allyl-3-butylimidazole chloride mixed phase into a round-bottom flask, adding excessive diethyl ether, stirring at 30 deg.C for 60 min, separating the lower ionic liquid phase with a separating funnel, removing the organic solvent remained in the ionic liquid by reduced pressure distillation, and vacuum drying at 80 deg.C for 10 h to completely remove volatile components. (3) The regenerated 1-allyl-3-butylimidazole chloride was added to 10 mL of a phenol-toluene solution having an initial phenol concentration of 50 g/L, stirred at 25 ℃ for 30 min, and then allowed to stand for 30 min, and the upper layer solution was taken out and analyzed by gas chromatography. (4) And (3) repeating the step (2) twice, three times and four times on the separated mixed phase of the chlorinated 1-allyl-3-butylimidazole of the second group to the fourth group, and then performing the step (3) to detect the concentration of the phenol. The experimental method for regenerating the ionic liquid comprises the following steps: (1) adding 1-allyl-3-butylimidazole chloride with an oil ratio of 1.0 into 10 mL of phenol-toluene solution with an initial phenol concentration of 50 g/L at room temperature, stirring at 25 ℃ for 30 min, standing for 30 min, taking the upper layer solution, analyzing by gas chromatography, and separating the lower ionic liquid mixed phase by using a separating funnel for later use. (2) Adding the separated ionic liquid mixed phase into a round-bottom flask, adding excessive organic solvent, stirring at 30 deg.C for 60 min, separating the lower ionic liquid phase with a separating funnel, removing the organic solvent remained in the ionic liquid by distillation under reduced pressure, vacuum drying at 80 deg.C for 10 h to completely remove volatile components, and repeating the step three times. (3) The regenerated 1-allyl-3-butylimidazole chloride was added to 10 mL of a phenol-toluene solution having an initial phenol concentration of 50 g/L, stirred at 25 ℃ for 30 min, and then allowed to stand for 30 min, and the upper layer solution was taken out and analyzed by gas chromatography. (4) Infrared characterization was performed on 1-allyl-3-butylimidazole chloride before and after regeneration.
Experimental example 4: and (3) recycling the ionic liquid: (1) at room temperature, four groups of brominated 1-allyl-3 methylimidazole with the oil ratio of 1.0 are respectively added into 10 mL of phenol-toluene solution with the initial phenol concentration of 50 g/L, the mixture is stirred for 30 min at 25 ℃, then the mixture is kept still for 30 min, the upper layer solution is taken and analyzed by gas chromatography, and the lower ionic liquid mixed phase is separated by a separating funnel for standby. (2) Adding the separated first group of brominated 1-allyl-3 methylimidazole mixed phase into a round-bottom flask, adding excessive diethyl ether, stirring at 30 ℃ for 60 min, separating the lower ionic liquid phase by using a separating funnel, removing the organic solvent remained in the ionic liquid by reduced pressure distillation, and drying at 80 ℃ for 10 h in vacuum to completely remove volatile components. (3) The regenerated brominated 1-allyl-3 methylimidazole was added to 10 mL of a phenol-toluene solution having an initial phenol concentration of 50 g/L, stirred at 25 ℃ for 30 min, and then allowed to stand for 30 min, and the upper layer solution was taken out and analyzed by gas chromatography. (4) And (4) repeating the step (2) twice, three times and four times on the separated mixed phase of the brominated 1-allyl-3 methylimidazole of the second group to the fourth group, and then performing the step (3) to detect the concentration of the phenol. Experimental method for regenerating ionic liquid: (1) adding brominated 1-allyl-3 methylimidazole with an oil agent ratio of 1.0 into 10 mL of phenol-toluene solution with the initial phenol concentration of 50 g/L at room temperature, stirring at 25 ℃ for 30 min, standing for 30 min, taking the upper layer solution, analyzing by using a gas chromatography, and separating the lower ionic liquid mixed phase by using a separating funnel for later use. (2) Adding the separated ionic liquid mixed phase into a round-bottom flask, adding excessive organic solvent, stirring at 30 deg.C for 60 min, separating the lower ionic liquid phase with a separating funnel, removing the organic solvent remained in the ionic liquid by distillation under reduced pressure, vacuum drying at 80 deg.C for 10 h to completely remove volatile components, and repeating the step three times. (3) The regenerated brominated 1-allyl-3 methylimidazole was added to 10 mL of a phenol-toluene solution having an initial phenol concentration of 50 g/L, stirred at 25 ℃ for 30 min, and then allowed to stand for 30 min, and the upper layer solution was taken out and analyzed by gas chromatography. (4) Infrared characterization was performed on the brominated 1-allyl-3 methylimidazole before and after regeneration.
Experimental example 5: reuse of ionic liquids: (1) respectively adding four groups of iodinated 1-allyl-3 methylimidazole with an oil ratio of 1.0 into 10 mL of phenol-toluene solution with an initial phenol concentration of 50 g/L at room temperature, stirring at 25 ℃ for 30 min, standing for 30 min, taking the upper layer of solution, analyzing by gas chromatography, and separating the lower ionic liquid mixed phase by using a separating funnel for later use. (2) Adding the first group of separated mixed phase of iodinated 1-allyl-3-methylimidazole into a round-bottom flask, adding excessive diethyl ether, stirring at 30 deg.C for 60 min, separating the lower ionic liquid phase with a separating funnel, removing the organic solvent remained in the ionic liquid by reduced pressure distillation, and vacuum drying at 80 deg.C for 10 h to completely remove volatile components. (3) The regenerated 1-allyl-3-methylimidazole iodide was added to 10 mL of a phenol-toluene solution having an initial phenol concentration of 50 g/L, stirred at 25 ℃ for 30 min, and then allowed to stand for 30 min, and the upper layer solution was taken out and analyzed by gas chromatography. (4) And (3) repeating the step (2) twice, three times and four times on the separated second group to fourth group of the iodized 1-allyl-3 methylimidazole mixed phase, and then performing the step (3) to detect the concentration of the phenol. The experimental method for the regenerated ionic liquid comprises (1) adding 1-allyl-3 methylimidazole iodide with an oil ratio of 1.0 into 10 mL of phenol-toluene solution with an initial phenol concentration of 50 g/L at room temperature, stirring at 25 ℃ for 30 min, standing for 30 min, taking the upper layer solution, analyzing by gas chromatography, and separating the lower ionic liquid mixed phase by using a separating funnel for later use. (2) Adding the separated ionic liquid mixed phase into a round-bottom flask, adding excessive organic solvent, stirring at 30 deg.C for 60 min, separating the lower ionic liquid phase with a separating funnel, removing the organic solvent remained in the ionic liquid by distillation under reduced pressure, vacuum drying at 80 deg.C for 10 h to completely remove volatile components, and repeating the step three times. (3) The regenerated 1-allyl-3-methylimidazole iodide was added to 10 mL of a phenol-toluene solution having an initial phenol concentration of 50 g/L, stirred at 25 ℃ for 30 min, and then allowed to stand for 30 min, and the upper layer solution was taken out and analyzed by gas chromatography. (4) The iodinated 1-allyl-3 methylimidazole before and after regeneration was subjected to infrared characterization.
Flory-Huggins interaction parameters between 5 ionic liquids and a probe solvent were determined by reverse gas chromatography (IGC). At 30 ℃, a total of 27 solvents are common poor solvents for five ionic liquids, including: normal alkane, cyclopentane, cyclohexane, isooctane, o-xylene, m-xylene, p-xylene, ethylbenzene, propylbenzene, butylbenzene, 3-pentanone, hexene, cyclohexene, octene, diethyl ether, butyl ether, tetrahydrofuran, methyl acetate, ethyl acetate, methyl propionate, ethyl propionate.
The infinite dilution activity coefficient of the ionic liquid with the probe solvent was determined by IGC assay. At 30 ℃, a total of 22 solvents are common poor solvents for five ionic liquids, including: normal alkane, cyclopentane, cyclohexane, isooctane, propylbenzene, butylbenzene, hexene, cyclohexene, octene, diethyl ether, butyl ether, tetrahydrofuran, methyl acetate, ethyl acetate, methyl propionate, ethyl propionate; the common poor solvent of the five ionic liquids calculated by the two methods is basically consistent with the solvent which is not miscible with the probe solvent and is found in the experimental result of the dissolution of the ionic liquid, so that the conclusion can be drawn by combining the two methods with the actual dissolution condition: 22 solvents in total, namely normal alkane, cyclopentane, cyclohexane, isooctane, propylbenzene, butylbenzene, hexene, cyclohexene, octene, diethyl ether, butyl ether, tetrahydrofuran, methyl acetate, ethyl acetate, methyl propionate and ethyl propionate, are common poor solvents of the five ionic liquids;
as shown in FIG. 2, which is a diagram of X, Y, Z axes of D, P, H triangles, the HSP distribution of phenol and 49 solvents is obtained, and according to the principle of "similar compatibility" between solvents, the smaller the spatial distance between phenol and solvent, the closer the Hansen solubility of phenol and the solvent is, the higher the solubility of phenol. In contrast, as the spacing distance increases, the solubility of phenol by such solvents gradually decreases;
according to previous experimental studies, diethyl ether is a solvent with good solubility for phenol. Therefore, ether is used herein as a critical solvent, and when the space distance between phenol and the solvent is smaller than the space distance between ether and phenol, it is defined as a good solvent for phenol. Conversely, a space distance greater than diethyl ether and phenol is defined as a poor solvent. The data above show that: the total 19 solvents of sec-butyl alcohol, tert-butyl alcohol, isobutyl alcohol, isopropanol, propanol, methyl formate, ethanol, tetrahydrofuran, methyl propionate, ethyl acetate, methyl acetate, 1, 4-dioxane, propylene oxide, methanol, thiophene, acetone, ethyl propionate and pyridine are good solvents of phenol; the optimal counter-solvent for the regeneration of the ionic liquid is as follows: the solvent has the smallest dissolving capacity on ionic liquid, but has larger solubility on phenol. Therefore, the ideal optimal counter-solvent is to satisfy: the ionic liquid is a poor solvent of the ionic liquid and is a good solvent of phenol.
The ionic liquid has 22 kinds of poor solvents, namely n-alkane, cyclopentane, cyclohexane, isooctane, propyl benzene, butylbenzene, hexene, cyclohexene, octene, diethyl ether, butyl ether, tetrahydrofuran, methyl acetate, ethyl acetate, methyl propionate and ethyl propionate; there are 19 good solvents for phenol, and these have small to large spatial distances from phenol in the order: sec-butyl alcohol, tert-butyl alcohol, isobutyl alcohol, isopropanol, propanol, methyl formate, ethanol, tetrahydrofuran, methyl propionate, ethyl acetate, methyl acetate, 1, 4-dioxane, propylene oxide, methanol, thiophene, acetone, ethyl propionate and pyridine. Only tetrahydrofuran, methyl propionate, ethyl acetate, methyl acetate, ethyl propionate, these 5 solvents meet the optimal counter-solvent preference conditions. Namely, the 5 solvents are not only common poor solvents of the five ionic liquids, but also good solvents of phenol. And the space distances between the 5 solvents and the phenol are in the order from small to large: tetrahydrofuran, methyl propionate, ethyl acetate, methyl acetate, ethyl propionate, i.e. the 5 solvents have a high to low dissolving capacity for phenol in the order of: tetrahydrofuran, methyl propionate, ethyl acetate, methyl acetate, ethyl propionate. According to the principle of "similar compatibility" between materials, as the spatial distance between phenol and a solvent is closer, the HSP of the phenol and the solvent is closer, so that the phenol can be better dissolved in the solvent; based on the above analysis: the sequence of predicting the regeneration efficiency of the 5 counter-extraction solvents on the ionic liquid from large to small is as follows: tetrahydrofuran, methyl propionate, ethyl acetate, methyl acetate, ethyl propionate; furthermore, the space distance between the 5 counter-solvents and phenol is greater than that of the critical solvent ether selected here, and the determination of the number of regenerations of the ionic liquid: in fig. 3, it can be seen that the final extraction concentration of phenol is significantly reduced in the former two times before the regeneration with diethyl ether, while the concentration of phenol is substantially unchanged after the three times of regeneration, and therefore, the number of back extraction experiments is selected to be three times;
as can be seen from fig. 4-8, the counter-solvent selected successfully regenerates five ionic liquids, and after regeneration, the functional groups of the ionic liquid are substantially consistent with those of the pure ionic liquid, which indicates that the counter-solvent does not damage the structure of the ionic liquid, and no chemical reaction occurs between the ionic liquid and the counter-solvent, which is only a physical adsorption process;
the back extraction experiment result is shown in fig. 1, and as can be seen from fig. 1, after five good solvents regenerate five ionic liquids, the back extraction effect is superior to that of the critical solvent diethyl ether. Experimental results show that tetrahydrofuran is the best regeneration effect of all good solvents after the regeneration of the five ionic liquids, and the final concentration of phenol is the lowest of the five solvents after the three times of regeneration;
the final extraction concentrations of the five counter-extraction solvents are in the order of small to large: tetrahydrofuran, methyl propionate, ethyl acetate, methyl acetate, ethyl propionate. And the space distances between the five solvents and the phenol are in the order from small to large: tetrahydrofuran, methyl propionate, ethyl acetate, methyl acetate, ethyl propionate. The results show that: the final extraction concentration of the good solvent after the regeneration of the ionic liquid is in direct proportion to the distance between the phenol and the good solvent, namely the smaller the distance between the phenol and the good solvent is, the lower the final phenol concentration is, and the better the regeneration effect is.
Drawings
FIG. 1 shows the back extraction effect of five good solvents and diethyl ether on five ionic liquids
FIG. 2 is a diagram showing the distribution of 49 solvents HSP in the phenol group
FIG. 3. results of four back extractions of [ AMIM ] Cl in ether solution
FIG. 4 Infrared Pattern of pure [ AMIM ] Cl and regenerated [ AMIM ] Cl
FIG. 5 Infrared Pattern of pure [ AEIM ] Cl and regenerated [ AEIM ] Cl
FIG. 6 Infrared Spectroscopy of pure [ ABIM ] Cl and regenerated [ ABIM ] Cl
FIG. 7 Infrared Pattern of pure [ AMIM ] Br and regenerated [ AMIM ] Br
FIG. 8 is an infrared image of pure [ AMIM ] I and regenerated [ AMIM ] I.
Claims (6)
1. The invention relates to the technical field of ionic liquid regeneration in an extraction separation process, in particular to a regenerated solvent for screening out ionic liquid based on the thermodynamic property of the ionic liquid and the three-dimensional solubility parameter of a solvent to be selected; Flory-Huggins interaction parameters and infinite dilution activity coefficients between the ionic liquid and the organic solvent are measured according to a reverse gas chromatography technology; meanwhile, calculating the contribution values D, P and H of the dispersion solubility parameter, the polar solubility parameter and the hydrogen bond solubility parameter of the organic solvent to the total solubility parameter according to the three-dimensional solubility parameter of the solvent to be selected; drawing the three-dimensional solubility parameters D, P and H of the solvent to be selected in a component contribution graph containing the contribution value of the three-dimensional solubility parameter of the material component to be separated to the total solubility parameter; according to the distance between the organic solvent and the substance component to be separated in the component contribution diagram, the solvent with good regeneration effect can be accurately screened out.
2. The method for screening out the regenerated solvent of the ionic liquid based on the thermodynamic properties of the ionic liquid and the three-dimensional solubility parameters of the solvent to be selected according to claim 1, which is characterized in that the organic solvent with good regeneration effect can be screened out accurately and rapidly.
3. The method for screening the regenerated solvent of the ionic liquid based on the thermodynamic properties of the ionic liquid and the three-dimensional solubility parameters of the candidate solvent according to claim 1 or 2, characterized in that Flory-Huggins interaction parameters and infinite dilution activity coefficients between the ionic liquid and the organic solvent are measured according to a reverse gas chromatography technique, and compared with the real dissolution situation of the ionic liquid in the solvent, in addition, a component contribution diagram containing the three-dimensional solubility values of the candidate solvent is obtained according to the following method: step one, drawing an equilateral triangle by using the contribution values D, P and H of the dispersion solubility parameter, the polar solubility parameter and the hydrogen bond solubility parameter to the total solubility parameter to obtain a solvent ternary diagram; and secondly, accurately and quickly presuming the solvent with good extraction and regeneration effects according to the distance between the organic solvent and the substance component to be separated in the component contribution diagram.
4. The method for screening and regenerating ionic liquid based on thermodynamic properties of ionic liquid and three-dimensional solubility parameters of candidate solvent according to claim 3, wherein the regenerated ionic liquid is obtained by the following method: step one, adding ionic liquid into 10 mL of phenol-toluene solution with the initial phenol concentration of 50 g/L at room temperature, stirring for 30 min at a certain temperature, standing for 30 min, taking the upper layer solution, analyzing by using a gas chromatograph, and separating the lower layer ionic liquid mixed phase by using a separating funnel for later use; secondly, adding the separated ionic liquid mixed phase into a round-bottom flask, adding excessive organic solvent, stirring for 60 min at 30 ℃, separating a lower ionic liquid phase by using a separating funnel, removing the organic solvent remained in the ionic liquid by reduced pressure distillation, drying for 10 h at 80 ℃ in vacuum, completely removing volatile components, and repeating the step for three times; thirdly, adding the regenerated ionic liquid into 10 mL of phenol-toluene solution with the initial phenol concentration of 50 g/L, stirring for 30 min at 25 ℃, standing for 30 min, and taking the upper layer solution for analysis by gas chromatography; (4) and performing infrared characterization on the ionic liquid before and after regeneration.
5. The method for screening the regenerated solvent of the ionic liquid according to claim 4, wherein the method for screening the regenerated solvent of the ionic liquid is based on thermodynamic properties of the ionic liquid and three-dimensional solubility parameters of a candidate solvent; the ionic liquid is characterized by comprising 1-allyl-3 methylimidazolium chloride [ AMIM ] Cl, 1-allyl-3 ethylimidazolium chloride [ AEIM ] Cl, 1-allyl-3 butylimidazolium chloride [ ABIM ] Cl, 1-allyl-3 methylimidazolium bromide [ AMIM ] Br and 1-allyl-3 methylimidazolium iodide [ AMIM ] I.
6. The method for screening out the regenerated solvent of the ionic liquid based on the thermodynamic properties of the ionic liquid and the three-dimensional solubility parameters of the candidate solvent as claimed in claim 4, wherein the selected extractant comprises tetrahydrofuran, methyl propionate, ethyl acetate, methyl acetate, ethyl propionate.
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