CN114349706A - Hydroxyl functional ionic liquid and preparation method thereof - Google Patents
Hydroxyl functional ionic liquid and preparation method thereof Download PDFInfo
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- CN114349706A CN114349706A CN202210013382.6A CN202210013382A CN114349706A CN 114349706 A CN114349706 A CN 114349706A CN 202210013382 A CN202210013382 A CN 202210013382A CN 114349706 A CN114349706 A CN 114349706A
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Abstract
The invention relates to the technical field of ionic liquid, in particular to hydroxyl functional ionic liquid and a preparation method thereof. Under the protection of nitrogen, slowly dropwise adding 2-bromoethanol and toluene into N-methylimidazole for reaction, and reacting and washing with anhydrous ether for several times after the reaction is finished to obtain a solid crude product 1-hydroxyethyl-3-methylimidazole bromine salt; dissolving the solid crude product by using a mixed solution of ethyl acetate and acetonitrile, recrystallizing, performing suction filtration, and drying; adding deionized water into the purified 1-hydroxyethyl-3-methylimidazole bromine salt for dilution, pouring the diluted solution into hydroxide type anion exchange resin, taking an effluent after the reaction is finished, adding propionic acid into hydroxide type intermediate 1-hydroxyethyl-3-methylimidazole, stirring the mixture at room temperature for reaction, performing rotary evaporation to remove water, and performing vacuum drying to obtain the target product. The method has the advantages of simple operation, low cost, high purity and strong stability.
Description
Technical Field
The invention relates to the technical field of ionic liquid, in particular to hydroxyl functional ionic liquid and a preparation method thereof.
Background
The ionic liquid has wide application in the fields of electrochemistry, catalytic reaction, chromatography, organic synthesis, biochemistry, solar cells, separation technology and the like, and has excellent physical properties such as good thermal stability, high conductivity, low electrochemical window, low flammability, low melting point, low vapor pressure, high ion density and the like. Has attracted extensive attention and research. Ionic liquids are organic salts which are liquid at room temperature and which are composed of an organic cation and an organic or inorganic anion. This molten salt in liquid form is distinguished from other ionic compounds.
With the development of science and technology, people are inevitably discharged with a lot of acid gases in production and life. Causing global warming and a series of environmental problems. Therefore, how to effectively treat the acid gas is an important task. The ionic liquid has great adjustability and processability and can be used for absorbing acid gas. The functional ionic liquid containing hydroxyl has remarkable absorption capacity on acid gases such as carbon dioxide, sulfur dioxide, hydrogen sulfide and the like.
Disclosure of Invention
The research on the ionic liquid at the present stage is not so perfect, and the new ionic liquid is continuously developed. The functional ionic liquid containing hydroxyl has the advantages of simple operation, low cost, high purity and strong stability.
In order to achieve the purpose, the technical scheme of the invention is as follows: a hydroxyl functional ionic liquid has a structural formula shown as (I):
the preparation method of the hydroxyl functional ionic liquid comprises the following steps:
1) synthesis of 1-hydroxyethyl-3-methylimidazolium bromide salt: under the protection of nitrogen, slowly dropwise adding 2-bromoethanol and toluene into N-methylimidazole for reaction, and reacting and washing with anhydrous ether for several times after the reaction is finished to obtain a solid crude product 1-hydroxyethyl-3-methylimidazole bromine salt;
2) purification of 1-hydroxyethyl-3-methylimidazolium bromide salt: dissolving the solid crude product by using a mixed solution of ethyl acetate and acetonitrile, recrystallizing, performing suction filtration, and drying;
3) synthesizing an oxyhydrogen type intermediate 1-hydroxyethyl-3-methylimidazole: adding deionized water into purified 1-hydroxyethyl-3-methylimidazolium bromide for dilution, pouring into hydroxide type anion exchange resin, collecting effluent after reaction, and continuously using AgNO3-HNO3Detecting the solution until the detection solution is precipitated or turbid, and stopping collecting;
4) adding propionic acid into the hydroxyl type intermediate 1-hydroxyethyl-3-methylimidazole, carrying out stirring reaction at room temperature, carrying out rotary evaporation to remove water, and carrying out vacuum drying to obtain the target ionic liquid 1-hydroxyethyl-3-methylimidazolic acid.
In the above preparation method of the hydroxyl functional ionic liquid, in step 1), the molar ratio of N-methylimidazole to 2-bromoethanol is 1: 1.1.
in the preparation method of the hydroxyl functional ionic liquid, in the step 1), the reaction temperature is 110 ℃, and the reaction time is 48 hours.
In the above preparation method of the hydroxyl functional ionic liquid, in step 2), the ratio by volume of ethyl acetate: acetonitrile 2: 1.
In the preparation method of the hydroxyl functional ionic liquid, in the step 2), the drying temperature is 65 ℃ and the drying time is 24 hours.
In the above preparation method of the hydroxyl functional ionic liquid, in step 3), the purified 1-hydroxyethyl-3-methylimidazolium bromide salt is prepared by the following steps: deionized water 1:1.
In the above preparation method of a hydroxyl functional ionic liquid, in step 4), the molar ratio of the hydroxyl type intermediate 1-hydroxyethyl-3-methylimidazole: propionic acid 1:1.
in the above preparation method of the hydroxyl functional ionic liquid, in the step 4), the stirring reaction time is 48 hours.
The invention synthesizes the hydroxyl functional ionic liquid on the basis of the bromine functional ionic liquid. The experiment expands the types of the ionic liquid, effectively ensures the purity of the obtained product, is convenient for effectively researching the physicochemical properties of the ionic liquid, and promotes the development of the ionic liquid.
Drawings
Fig. 1 is a hydrogen spectrum of the hydroxyl functional ionic liquid prepared in example 1.
Fig. 2 is a carbon spectrum of the hydroxyl functional ionic liquid prepared in example 1.
Detailed Description
The invention is further illustrated by the following specific examples. The invention is not limited to the embodiments, but may be varied slightly without departing from the scope of the invention.
Example 1A hydroxyl functional Ionic liquid
The preparation method comprises the following steps:
1) preparing a functional imidazole ionic liquid bromide salt containing hydroxyl:
adding a proper amount of 80ml of N-methyl imidazole into a three-neck flask, slowly adding 178ml of 2-bromoethanol under the protection of nitrogen, heating and stirring by using an oil bath pot after dropwise addition is finished, and carrying out reflux reaction for 48 hours at the temperature of 110 ℃. The product obtained is washed three times with a mixture of 10ml of ethyl acetate and 5ml of acetonitrile, recrystallized and filtered off with suction. And then putting the liquid into a dryer, and drying for 24h to obtain the 1-hydroxyethyl-3-methylimidazolium bromide ionic liquid. The molar ratio of N-methylimidazole to 2-bromoethanol is 1: 1.1.
2) And (3) taking 717 rows of anion exchange resin, and performing activation regeneration and treatment to obtain the hydroxide-type anion exchange resin. Loading the hydroxide anion exchange resin into a column, washing with water to neutrality, and draining. And pouring the 1-hydroxyethyl-3-methylimidazolium bromide ionic liquid into resin, and reacting for 2-4 h. Collecting the effluent liquid after the reaction is finished, and continuously using AgNO when the effluent liquid is collected3-HNO3And (5) detecting the solution until the detection solution is precipitated or turbid, and stopping collecting.
3) Mixing the 60ml hydroxide type ionic liquid and 50ml propionic acid, reacting for 48h at room temperature, rotary evaporating to remove water, and vacuum drying at 55 deg.C for 3 days to obtain 1-hydroxyethyl-3-methylimidazolium propionate subphase liquid with yield of 85.6% and purity of 98%. The molar ratio of the 1-hydroxyethyl-3-methylimidazolium bromide to the propionic acid is 1:1.
FIG. 1 is a nuclear magnetic hydrogen spectrum of the prepared ionic liquid, the characteristic peak of each hydrogen and the position of the hydrogen on the corresponding functional group of the ionic liquid are shown in FIG. 1, and the characteristic peak of the hydrogen in FIG. 1 accords with the position of the hydrogen contained in the 1-hydroxyethyl-3-methylimidazolium propionate ionic liquid. FIG. 2 is a nuclear magnetic carbon spectrum of the prepared ionic liquid, the characteristic peak of each carbon and the position of the corresponding ionic liquid carbon are shown in FIG. 2, and the characteristic peak of the carbon in FIG. 2 accords with the position of each group carbon of the 1-hydroxyethyl-3-methylimidazolium propionate ionic liquid.
Claims (9)
1. A hydroxyl functional ionic liquid is characterized by having a structural formula shown as (I):
2. the preparation method of the hydroxyl functional ionic liquid as claimed in claim 1, which is characterized by comprising the following steps:
1) synthesis of 1-hydroxyethyl-3-methylimidazolium bromide salt: under the protection of nitrogen, slowly dropwise adding 2-bromoethanol and toluene into N-methylimidazole for reaction, and reacting and washing with anhydrous ether for several times after the reaction is finished to obtain a solid crude product 1-hydroxyethyl-3-methylimidazole bromine salt;
2) purification of 1-hydroxyethyl-3-methylimidazolium bromide salt: dissolving the solid crude product by using a mixed solution of ethyl acetate and acetonitrile, recrystallizing, performing suction filtration, and drying;
3) synthesizing an oxyhydrogen type intermediate 1-hydroxyethyl-3-methylimidazole: adding deionized water into purified 1-hydroxyethyl-3-methylimidazolium bromide for dilution, pouring into hydroxide type anion exchange resin, collecting effluent after reaction, and continuously using AgNO3-HNO3Detecting the solution until the detection solution is precipitated or turbid, and stopping collecting;
4) adding propionic acid into the hydroxyl type intermediate 1-hydroxyethyl-3-methylimidazole, carrying out stirring reaction at room temperature, carrying out rotary evaporation to remove water, and carrying out vacuum drying to obtain the target ionic liquid 1-hydroxyethyl-3-methylimidazolic acid.
3. The method for preparing hydroxyl functional ionic liquid according to claim 2, wherein in the step 1), the molar ratio of N-methylimidazole to 2-bromoethanol is 1: 1.1.
4. the method for preparing hydroxyl functional ionic liquid according to claim 2, wherein the reaction temperature in the step 1) is 110 ℃ and the reaction time is 48 h.
5. The method for preparing hydroxyl functional ionic liquid according to claim 2, wherein in the step 2), the volume ratio of ethyl acetate: acetonitrile 2: 1.
6. The method for preparing hydroxyl functional ionic liquid according to claim 2, wherein in the step 2), the drying temperature is 65 ℃ and the drying time is 24 h.
7. The method for preparing hydroxyl functional ionic liquid according to claim 2, wherein in the step 3), the volume ratio of the purified 1-hydroxyethyl-3-methylimidazolium bromide is as follows: deionized water 1:1.
8. The method for preparing hydroxyl functional ionic liquid according to claim 2, wherein in the step 4), the molar ratio of the hydroxyl type intermediate 1-hydroxyethyl-3-methylimidazole: propionic acid 1:1.
9. the method for preparing hydroxyl functional ionic liquid according to claim 2, wherein the stirring reaction time in the step 4) is 48 h.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115536588A (en) * | 2022-11-10 | 2022-12-30 | 辽宁大学 | Hydroxy glycine functional ionic liquid, preparation method thereof and application thereof in iodine extraction |
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| CN102559807A (en) * | 2012-01-31 | 2012-07-11 | 青岛科技大学 | Method of in-situ enzymatic hydrolysis of cellulose in ionic liquid |
| CN106220566A (en) * | 2016-07-21 | 2016-12-14 | 辽宁大学 | A kind of with amino acid whose ionic liquid and its preparation method and application |
| CN107353252A (en) * | 2017-08-03 | 2017-11-17 | 辽宁大学 | A kind of ionic liquid with carboxylic acid and its preparation method and application |
| CN107602475A (en) * | 2017-10-31 | 2018-01-19 | 辽宁大学 | Propyl imidazole taurine ionic liquid of 1 methyl 3 and its preparation method and application |
| CN110330459A (en) * | 2019-07-18 | 2019-10-15 | 中国科学院过程工程研究所 | A kind of carboxylate ion liquid and the preparation method and application thereof |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102559807A (en) * | 2012-01-31 | 2012-07-11 | 青岛科技大学 | Method of in-situ enzymatic hydrolysis of cellulose in ionic liquid |
| CN106220566A (en) * | 2016-07-21 | 2016-12-14 | 辽宁大学 | A kind of with amino acid whose ionic liquid and its preparation method and application |
| CN107353252A (en) * | 2017-08-03 | 2017-11-17 | 辽宁大学 | A kind of ionic liquid with carboxylic acid and its preparation method and application |
| CN107602475A (en) * | 2017-10-31 | 2018-01-19 | 辽宁大学 | Propyl imidazole taurine ionic liquid of 1 methyl 3 and its preparation method and application |
| CN110330459A (en) * | 2019-07-18 | 2019-10-15 | 中国科学院过程工程研究所 | A kind of carboxylate ion liquid and the preparation method and application thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115536588A (en) * | 2022-11-10 | 2022-12-30 | 辽宁大学 | Hydroxy glycine functional ionic liquid, preparation method thereof and application thereof in iodine extraction |
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