CN110294712B - Preparation method of high-purity imidazole acetate ionic liquid - Google Patents
Preparation method of high-purity imidazole acetate ionic liquid Download PDFInfo
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
Abstract
The invention belongs to the technical field of ionic liquid synthesis, and particularly relates to a preparation method of high-purity imidazole acetate ionic liquid, which comprises the steps of reacting a 1-alkyl-3-methylimidazole halogenated product with lithium perchlorate to obtain a high-purity 1-alkyl-3-methylimidazole perchlorate ionic liquid intermediate; then carrying out double decomposition reaction on the intermediate and potassium acetate or ammonium acetate to obtain the 1-alkyl-3-methylimidazole acetate ionic liquid, wherein the raw materials are cheap and easy to obtain, the raw materials or intermediate byproducts are free of heavy metal or other pollution, the reaction is thorough, the reaction yield is higher than 90.0%, the product purity is higher than 99.0%, the halogen residue in the product is less than or equal to 5ppm, and the content of K ions or ammonium radicals in the product is less than 200 ppm.
Description
Technical Field
The invention belongs to the field of ionic liquid synthesis, and particularly relates to a preparation method of a high-purity ionic liquid with imidazole (ring) as a cation and acetate as an anion.
Background
The ionic liquid is a new functional material, has the advantages of extremely low vapor pressure, high conductivity, stable chemical property, flowable physical form and the like, and is a hot spot with great development prospect in research of researchers at home and abroad at present. Besides the advantages, the ionic liquid has the characteristics of multiple types, and both the anion structure and the cation structure can be subjected to molecular grafting according to the needs, so that the ionic liquid is a future chemical material with universality; on the other hand, the ionic liquid has the greatest advantages of environmental protection and no volatile loss in the using process, and the concept of environmental protection is very suitable for the concept of environmental protection. At present, the ionic liquid is applied in the directions of catalytic esterification, functional addition, functional solvent dissolution, electrochemistry and the like in a pilot scale mode, and the industrialized application scale is realized in individual fields.
The research on the ionic liquid in physical property and structure in China is more and more intensive, and compared with the concept of application from experiments to production in the early century, the research is at the level of predicting the application direction from the structure. With the progress of research, it has been realized that small amounts of impurities in ionic liquids have a significant influence on their properties and applications, in particular with regard to viscosity, conductivity, dissolution/catalytic activity, etc., and can even have a decisive influence. It is often noted that different databases or documents describe the properties of the same ionic liquid in a very different way, and ultimately, the properties are caused by different synthetic methods and different purities. High purity ionic liquids are critical to basic research and applications.
The synthesis of high-purity ionic liquid depends on the purification of reaction raw materials, the control of reaction conditions, synthesis skills, a purification method of products and the like (ionic liquid-property preparation and application, dandong, P37). Acetate is an ionic liquid with a wide application range, such as 1-ethyl-3-methylimidazole acetate, and is applied in the directions of dissolving cellulose, chitin, recrystallizing chemicals and the like at present, but acetate is very active due to chemical properties, has high synthesis difficulty, is complex in process and is difficult to control the purity of a product.
At present, acetic acid ionic liquid synthesis methods are shown in more than ten methods in the declaration, and imidazole halide is generally prepared by one-step or multi-step conversion.
EMIMBr is reacted with silver acetate to prepare EMIMOAc ionic liquid. The reaction can be completed at room temperature, the reaction time is short, and the purification steps are few. However, the raw material AgAc is expensive, is easy to decompose when exposed to light, needs special protection measures, increases the preparation cost of the ionic liquid, and is not beneficial to realizing industrialization.
Resin ion exchange method: the ion exchange resin is changed into OH type, EMIMCl or EMIMBr is changed into EMIMOH through resin exchange, so that an aqueous solution of EMIMOH is obtained, and then the aqueous solution reacts with acetic acid. The method has long time in the synthesis process, needs continuous detection in the midway, has unstable intermediate products and is difficult to control the product purity.
The preparation method of 1-ethyl-3-methylimidazole acetate is proposed in the Wanyi week of northwest kingdom university, and EMIMBr is synthesized by using N-methylimidazole and bromoethane, and then EMIMOAc is synthesized by using lead acetate as ion exchange. The method has the advantages of numerous byproducts and serious environmental pollution, and a large amount of lead ions remain in the product in a complexing mode.
CN1914181A discloses two preparation methods of imidazole acetate ionic liquid, wherein the preparation processes of the two methods are complex, the used raw material alkoxide is high in price and inflammable, reactants are extremely sensitive to water, the cost is high, the control is not facilitated, and impurities such as sulfur, barium and the like are easily introduced.
CN101337938A discloses a method for preparing imidazole acetate ionic liquid, which comprises dissolving inorganic acetate and halide ionic liquid containing target cations in organic alcohol solvent, respectively, to prepare organic alcohol solution; carrying out double decomposition reaction under the stirring condition to obtain reaction mixed liquid; cooling, filtering, collecting filtrate, and removing organic alcohol solvent in the filtrate to obtain imidazole acetate ionic liquid. The method can obtain the imidazole acetate ionic liquid by one-step conversion of the imidazole halide ionic liquid, and the used inorganic acetate and organic alcohol solvents are low in price and low in toxicity, but the yield and the purity of the obtained imidazole acetate ionic liquid are low.
CN101108827A discloses a method for preparing acetic acid type ionic liquid, which comprises the steps of mixing potassium acetate, ethanol and imidazole halide for reaction, carrying out ion exchange, cooling the obtained mixture to-20-0 ℃, and filtering to remove solid byproduct salt and potassium acetate which may exist in the mixture. This process is similar to the process disclosed in CN101337938A but still does not produce ionic liquids in high yield and purity.
CN102190623A on the basis of CN101337938A, part of organic alcohol in a reaction system is distilled off in the reaction process; and filtering the reaction mixed solution and removing the organic alcohol in the filtrate to obtain the imidazole acetate ionic liquid, wherein the yield can reach 99.3 percent at most. The synthesis routes of the two are similar, and during the actual operation process, the salts such as potassium chloride, potassium bromide and the like generated by ion exchange in the reaction generate precipitation in the alcohol solution, and the precipitation is filtered and separated. The method is simple, convenient and economical, has little pollution to the environment, but before the reaction, because EMIMCl or EMIMBr is easy to absorb water and is difficult to dry, and the synthesized byproduct KCl has high solubility in water, even if the water is extremely micro, the product contains potassium ions of about 5000 plus 10000ppm and a large amount of halogen ions, and the whole production condition uses a large amount of ethanol.
CN103420915A discloses adding weighed 1-substituent imidazole and dimethyl carbonate into an ionic liquid preparation device to obtain 1-substituent-3-methylimidazole methyl carbonate; adding the weighed glacial acetic acid into a three-neck flask, and reacting the glacial acetic acid with 1-substituent-3-methylimidazole methyl carbonate to obtain 1-substituent-3-methylimidazole acetate type ionic liquid; and purified using a high vacuum distillation apparatus. The method can prepare the acetic acid ionic liquid under the conditions of normal pressure and low temperature without additional solvents, catalysts and reaction kettles. However, the reaction has low conversion rate (up to 91.5 percent), and a great deal of 1-substituted imidazole raw material remains in the product. Moreover, during the synthesis process, the C at the 2-position of the 1-substituted imidazole reacts with dimethyl carbonate to generate some carbonyl byproducts, so that the product is impure.
In summary, the current preparation method of the acetic acid ionic liquid has the following problems: the feedstock contains heavy metals or other contaminants; the raw materials are expensive; the reaction is not completely carried out or disproportionation easily occurs; the reaction process is slow; the reaction conditions are harsh, and the product has more water, halogen and metal ion residues.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and seek to design a preparation method of high-purity imidazole acetate ionic liquid, wherein a 1-alkyl-3-methylimidazole halogenated product reacts with lithium perchlorate to obtain a high-purity 1-alkyl-3-methylimidazole perchlorate ionic liquid intermediate; then carrying out double decomposition reaction on the intermediate and potassium acetate or ammonium acetate to obtain the 1-alkyl-3-methylimidazole acetate ionic liquid, wherein the raw materials are cheap and easy to obtain, the raw materials or intermediate byproducts are free of heavy metal or other pollution, the reaction is thorough, the reaction yield is higher than 90.0%, and the product purity is higher than 99.0%.
The object of the invention is thus achieved: a preparation method of high-purity imidazole acetate ionic liquid comprises the following steps:
(1) dissolving the 1-alkyl-3-methylimidazole halogenated product with water with the mass of about 1/3 to obtain a solution A; dissolving lithium perchlorate in water with the mass of about 2 times of that of the lithium perchlorate to obtain solution B;
(2) mixing the solution A and the solution B, adding a proper amount of dichloromethane, and mechanically stirring for reaction for 12 hours;
(3) separating to obtain water phase as waste liquid, recovering, washing the organic phase with pure water about 1/3 volume, and washing several times until AgNO is adopted3No precipitate, namely no halogen residue, is detected by the solution;
(4) carrying out vacuum rotary evaporation on the organic phase without halogen residues in the step (3) at 80 ℃ to obtain a high-purity 1-alkyl-3-methylimidazole perchlorate ionic liquid intermediate;
(5) adding 2-5 times of ethanol into the intermediate to obtain an ethanol solution of 1-alkyl-3-methylimidazole perchlorate;
(6) slowly adding potassium acetate or ammonium acetate into the solution in batches under the condition of vigorous stirring; during the addition process, the solid is continuously dissolved and separated out; continuously stirring and reacting for 12-48 hours;
(7) stopping stirring, freezing to-15 deg.C, and maintaining for 12-36 hr to age impurities;
(8) filtering, recovering a filter cake, and performing rotary evaporation on the filtrate at 80 ℃ to obtain a crude product;
(9) adding a certain amount of 18-crown-6 into dichloromethane to form a mixed solution, wherein the mass of 18-crown-6 is 0.5-2% of that of dichloromethane, then adding a crude product into the mixed solution with the volume of 3-5 times of that of the crude product, freezing to-15 ℃, keeping for 12-36 hours, filtering, and carrying out rotary evaporation on the filtrate at 60 ℃;
(10) and removing the 18-crown-6 liquid to obtain the high-purity 1-alkyl-3-methylimidazole acetate ionic liquid.
In the invention, the halogenated product of the 1-alkyl-3-methylimidazole has the following structural formula (I):
wherein R is C1-C8The linear alkyl group of (1) is preferably an ethyl group, a butyl group,Hexyl or octyl, more preferably ethyl or butyl, and X is selected from Cl or Br.
In the invention, the 1-alkyl-3-methylimidazole acetate ionic liquid has the following structural formula (II):
wherein R is C1-C8The linear alkyl group of (3) is preferably one of ethyl, butyl, hexyl and octyl, and more preferably ethyl or butyl.
In step (1) of the present invention, the molar ratio of the 1-alkyl-3-methylimidazole halogenated product to lithium perchlorate is 1.0: (0.8-2.0). In the step (2), the adding amount of the dichloromethane is close to the mass of the mixed solution of the solution A and the solution B.
In step (6) of the present invention, it is preferable that potassium acetate or ammonium acetate is added in a solid form, the total amount is added in an amount equimolar to 1-alkyl-3-methylimidazole perchlorate, it is preferable that potassium acetate is added, and it is preferable that it is added in 4 portions.
The high purity in the invention means that the purity is higher than 99.0%.
The reaction equation involved in the invention is as follows:
in the formula: m is K+Or NH4 +Is preferably K+. In the invention, 1-alkyl-3-methylimidazole perchlorate ionic liquid is used as an intermediate in the first step of reaction to replace a halide to be used as a reaction raw material to react with potassium acetate or ammonium acetate, and compared with the halide, the reaction is carried out by one step more, so that the synthesis and purification are easier, and the residues and entrainment of halogen, metal ions and other anions can be avoided; the second step of reaction, the solubility of the potassium perchlorate or ammonium perchlorate byproduct in water is small, the water in the raw material has little influence on the purity of the product, the residual potassium or ammonium in the product is little, the purity is high, and the K in the product can be greatly reduced+Or NH4+The purity of the obtained product is greatly improved by the residue; dichloromethane and 18-crown-6 are used as purification solvents, so that alkali metal ions in the ionic liquid can be greatly reduced; potassium acetate or ammonium acetate can be directly added into the ethanol solvent of 1-alkyl-3-methylimidazole perchlorate in a solid form, and the dosage of ethanol is less.
Compared with the prior art, the invention has the following advantages and remarkable progress:
the raw materials are cheap and easy to obtain, and the raw materials or intermediate byproducts do not have heavy metal or other pollution; the reaction is thorough without disproportionation and other side reactions; the reaction yield is higher than 90.0%; the product purity is high, generally more than 99.0 percent, even up to 99.4 percent; the halogen residue in the product is less than or equal to 5ppm, and the content of K ions or ammonium radicals in the product is less than 200 ppm; the reaction speed is moderate.
Detailed Description
The following further describes the embodiments of the present invention.
Example 1
Preparing 1-ethyl-3-methylimidazole acetate ionic liquid:
dissolving 1.0mol of 1-ethyl-3-methylimidazole chloride salt in 48g of water to obtain a solution A, and dissolving 1.2mol of lithium perchlorate in 254g of water to obtain a solution B; mixing the solution A and the solution B, adding 575g of dichloromethane, and mechanically stirring to react for 12 hours; separating, collecting water phase as waste liquid, recovering, washing organic phase with 260g of pure water for 5 times, and AgNO3Detecting the solution without precipitation; the organic phase is subjected to vacuum rotary evaporation at the temperature of 80 ℃ to obtain 193g of 1-ethyl-3-methylimidazole perchlorate ionic liquid intermediate with the yield of 91.9%; adding 579g of ethanol, slowly adding 90.1g of potassium acetate in 4 batches under vigorous stirring, continuously dissolving and separating out solids in the adding process, and continuously stirring for reacting for 24 hours; stopping stirring, freezing to-15 deg.C, maintaining for 24 hr, filtering, recovering filter cake, and rotary steaming filtrate at 80 deg.C; cooling to room temperature, adding 4 times volume of mixed solution of dichloromethane and 18-crown-6 (crown ether is mixed with dichloromethane in advance, accounting for 1% of dichloromethane mass), freezing to-15 deg.C, maintaining for 24 hr, filtering, and rotary evaporating filtrate at 60 deg.C; removing 18-crown-6 liquidThe total amount of the obtained 1-ethyl-3-methylimidazole acetate ionic liquid is 154.0g, the yield is 90.5%, the purity is 99.3% by high performance liquid chromatography detection, the K ion residue is less than or equal to 120ppm, and the Cl ion residue is less than or equal to 5 ppm.
Example 2
Preparation of 1-butyl-3-methylimidazole acetate ionic liquid:
dissolving 1.0mol of 1-butyl-3-methylimidazolium bromide salt with 58g of water to obtain a solution A, and dissolving 0.8mol of lithium perchlorate with 170g of water to obtain a solution B; mixing the solution A and the solution B, adding 531g of dichloromethane, and mechanically stirring for reaction for 12 hours; separating, cleaning organic phase with 278g pure water for 3 times, and AgNO3Detecting the solution without precipitation; the organic phase is subjected to vacuum rotary evaporation at the temperature of 80 ℃ to obtain 178.4g of 1-butyl-3-methylimidazole perchlorate ionic liquid intermediate with the yield of 93.7 percent; 446g of ethanol is added, 79.8g of potassium acetate is slowly added in 4 batches under the condition of vigorous stirring, solid is continuously dissolved and separated out in the adding process, and the stirring reaction is continuously carried out for 12 hours; stopping stirring, freezing to-15 deg.C, maintaining for 36 hr, filtering, and rotary steaming the filtrate at 80 deg.C; cooling to room temperature, adding 3 times volume of mixed solution of dichloromethane and 18-crown-6 (crown ether is mixed with dichloromethane in advance, accounting for 0.5% of dichloromethane mass), freezing to-15 deg.C, maintaining for 12 hr, filtering, and rotary evaporating filtrate at 60 deg.C; the 18-crown-6 liquid is removed, and the total amount of the 1-butyl-3-methylimidazolium acetate ionic liquid is 145.9g, the yield is 92.0%, the purity is 99.4% by high performance liquid chromatography, the K ion residue is less than or equal to 60ppm, and the Cl ion residue is less than or equal to 5 ppm.
Example 3
Preparing 1-octyl-3-methylimidazole acetate ionic liquid:
dissolving 1.0mol of 1-octyl-3-methylimidazole chloride salt in 78g of water to obtain a solution A, and dissolving 2.0mol of lithium perchlorate in 426g of water to obtain a solution B; mixing the solution A and the solution B, adding 841g of dichloromethane, and mechanically stirring to react for 12 hours; separating, collecting water phase as waste liquid, recovering, washing organic phase with 256g pure water for 3 times, and AgNO3Detecting the solution without precipitation; the organic phase is rotary evaporated in vacuo at 80 ℃ to give 193g of 1-octyl-3-methylimidazole perchlorate ionic liquid intermediate with a yield of 91.9%; 965g of ethanol is added, 90.1g of potassium acetate is slowly added in 4 batches under vigorous stirring, solid dissolution and precipitation are not stopped in the adding process, and stirring reaction is continued for 48 hours; stopping stirring, freezing to-15 deg.C, maintaining for 12 hr, filtering, and recovering filter cake; rotary steaming the filtrate at 80 ℃; cooling to room temperature, adding 5 times volume of mixed solution of dichloromethane and 18-crown-6 (crown ether is mixed with dichloromethane in advance, accounting for 2% of dichloromethane mass), freezing to-15 deg.C, maintaining for 36 hr, filtering, and rotary evaporating filtrate at 60 deg.C; and removing the 18-crown-6 liquid, so as to obtain 248.3g of 1-octyl-3-methylimidazole acetate ionic liquid in total, wherein the yield is 90.0%, the purity is 99.1% by high performance liquid chromatography, the K ion residue is less than or equal to 100ppm, and the Cl ion residue is less than or equal to 5 ppm.
Example 4
Preparation of 1-ethyl-3-methylimidazole acetate ionic liquid:
dissolving 1.0mol of 1-ethyl-3-methylimidazole chloride salt in 48g of water to obtain a solution A, and dissolving 1.2mol of lithium perchlorate in 254g of water to obtain a solution B; mixing the solution A and the solution B, adding 575g of dichloromethane, and mechanically stirring to react for 12 hours; separating, collecting water phase as waste liquid, recovering, washing organic phase with 260g of pure water for 5 times, and AgNO3Detecting the solution without precipitation; the organic phase is subjected to vacuum rotary evaporation at the temperature of 80 ℃ to obtain 193g of 1-ethyl-3-methylimidazole perchlorate ionic liquid intermediate with the yield of 91.9%; adding 579g of ethanol, slowly adding 70.6g of ammonium acetate in 4 batches under vigorous stirring, continuously dissolving and separating out solids in the adding process, and continuously stirring for reacting for 24 hours; stopping stirring, freezing to-15 deg.C, maintaining for 24 hr, filtering, recovering filter cake, and rotary steaming the filtrate at 80 deg.C; cooling to room temperature, adding 4 times volume of mixed solution of dichloromethane and 18-crown-6 (crown ether is mixed with dichloromethane in advance, accounting for 1% of dichloromethane mass), freezing to-15 deg.C, maintaining for 24 hr, filtering, and rotary evaporating filtrate at 60 deg.C; removing 18-crown-6 liquid to obtain 154.0g of 1-ethyl-3-methylimidazolium acetate ionic liquid in total, wherein the yield is 90.5%, the purity is 99.0% by high performance liquid chromatography, the ammonium radical residue is less than or equal to 120ppm, and the Cl ion residue isThe residue is less than or equal to 5 ppm.
Comparative example 1
Preparation of 1-ethyl-3-methylimidazole acetate ionic liquid:
adding 1.0mol of 1-ethyl-3-methylimidazole chloride salt into 880g of ethanol, slowly adding 90.1g of potassium acetate in 4 batches under vigorous stirring, continuously dissolving and separating out solids in the adding process, and continuously stirring for reacting for 24 hours; stopping stirring, freezing to-15 ℃, keeping for 24 hours, filtering, recovering filter cakes, and carrying out rotary evaporation on the filtrate at 80 ℃ to obtain 153.0g of 1-ethyl-3-methylimidazole acetate ionic liquid in total, wherein the yield is 90.0%, the purity is 97.0% by high performance liquid chromatography, the K ion residue is 8200ppm, and the Cl ion residue is 6400 ppm.
Comparative example 2
The same as in example 1 except that dichloromethane was not added gave 19g of 1-ethyl-3-methylimidazole perchlorate ionic liquid intermediate in a yield of 9.0%.
Comparative example 3
Same as example 1, except that no crown ether 18-crown-6 was added to methylene chloride in the final purification step, the yield was 90.5%, the purity was 98.8%, the K ion residue was 1200ppm, and the Cl ion residue was 5ppm or less.
Therefore, the preparation method of the invention has the advantages of thorough reaction, no disproportionation and no other side reaction; the reaction yield is higher than 90.0%; the product purity is high, generally more than 99.0 percent, even up to 99.4 percent; the halogen residue in the product is less than or equal to 5ppm, and the content of K ions or ammonium radicals in the product is less than 200 ppm; the reaction speed is moderate.
Claims (7)
1. The preparation method of the imidazole acetate ionic liquid is characterized by comprising the following steps:
(1) dissolving 1-alkyl-3-methylimidazole halide by using water with the mass of about 1/3 to obtain a solution A; dissolving lithium perchlorate in water with the mass of about 2 times of that of the lithium perchlorate to obtain solution B;
(2) mixing the solution A and the solution B, adding a proper amount of dichloromethane, and mechanically stirring for reaction for 12 hours;
(3) separating to obtain water phase as waste liquid, recovering, and using organic phase1/3 volume of pure water, and cleaning for several times until AgNO is adopted3No precipitate, namely no halogen residue, is detected by the solution;
(4) carrying out vacuum rotary evaporation on the organic phase without halogen residues in the step (3) at the temperature of 80 ℃ to obtain a 1-alkyl-3-methylimidazole perchlorate ionic liquid intermediate;
(5) adding 2-5 times of ethanol into the intermediate to obtain an ethanol solution of 1-alkyl-3-methylimidazole perchlorate;
(6) slowly adding potassium acetate or ammonium acetate into the solution in batches under the condition of vigorous stirring; during the addition process, the solid is continuously dissolved and separated out; continuously stirring and reacting for 12-48 hours;
(7) stopping stirring, freezing to-15 deg.C, and maintaining for 12-36 hr to age impurities;
(8) filtering, recovering a filter cake, and performing rotary evaporation on the filtrate at 80 ℃ to obtain a crude product;
(9) adding a certain amount of 18-crown-6 into dichloromethane to form a mixed solution, wherein the mass of 18-crown-6 is 0.5-2% of that of dichloromethane, then adding a crude product into the mixed solution with the volume of 3-5 times of that of the crude product, freezing to-15 ℃, keeping for 12-36 hours, filtering, and carrying out rotary evaporation on the filtrate at 60 ℃;
(10) removing the 18-crown-6 liquid to obtain 1-alkyl-3-methylimidazolium acetate ionic liquid;
the halogenated product of the 1-alkyl-3-methylimidazole has the following structural formula (I):
wherein R is C1-C8X is selected from one of Cl or Br;
the 1-alkyl-3-methylimidazole acetate ionic liquid has the following structural formula (II):
whereinR is C1-C8Linear alkyl group of (1).
2. The method for preparing imidazole acetate ionic liquid according to claim 1, wherein R is one of ethyl, butyl, hexyl, and octyl.
3. The method for preparing imidazole acetate ionic liquid according to claim 2, wherein R is ethyl or butyl.
4. The method for preparing imidazole acetate ionic liquid according to claim 1, wherein in the step (1), the molar ratio of the 1-alkyl-3-methylimidazole halogenated product to the lithium perchlorate is 1.0: (0.8-2.0).
5. The method for preparing imidazole acetate ionic liquid according to claim 1, wherein in the step (6), the potassium acetate or ammonium acetate is added in a solid form, and the total amount is added in an equimolar amount with 1-alkyl-3-methylimidazole perchlorate.
6. The method for preparing imidazole acetate ionic liquid according to claim 5, characterized in that potassium acetate is added.
7. The method for preparing imidazole acetate ionic liquid according to claim 6, wherein potassium acetate is added in 4 batches.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101337938A (en) * | 2007-07-04 | 2009-01-07 | 中国纺织科学研究院 | Method for synthesizing acetate ionic liquid |
| CN101633641A (en) * | 2009-08-11 | 2010-01-27 | 华南师范大学 | Preparation method of imidazole type ionic liquid |
| CN102190623A (en) * | 2011-03-25 | 2011-09-21 | 中国纺织科学研究院 | Method for preparing imidazole acetate ionic liquid |
| CN102603644A (en) * | 2012-01-19 | 2012-07-25 | 林州市科能材料科技有限公司 | Production method of alkylimidazole ionic liquid |
-
2019
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101337938A (en) * | 2007-07-04 | 2009-01-07 | 中国纺织科学研究院 | Method for synthesizing acetate ionic liquid |
| CN101633641A (en) * | 2009-08-11 | 2010-01-27 | 华南师范大学 | Preparation method of imidazole type ionic liquid |
| CN102190623A (en) * | 2011-03-25 | 2011-09-21 | 中国纺织科学研究院 | Method for preparing imidazole acetate ionic liquid |
| CN102603644A (en) * | 2012-01-19 | 2012-07-25 | 林州市科能材料科技有限公司 | Production method of alkylimidazole ionic liquid |
Non-Patent Citations (2)
| Title |
|---|
| Ionic liquid ion exchange: exclusion from strong interactions condemns cations to the most weakly interacting anions and dictates reaction equilibrium;Pieter Naert 等;《Green Chem.》;20180810;第20卷;4277-4286 * |
| Thermodynamic and molecular origin of interfacial rate enhancements and endo-selectivities of a Diels–Alder reaction;Vijay Beniwal等;《Phys.Chem.Chem.Phys.》;20170109;第19卷;4297-4306 * |
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