CN109134377A - A kind of preparation method of ionic liquid - Google Patents
A kind of preparation method of ionic liquid Download PDFInfo
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- CN109134377A CN109134377A CN201811095257.4A CN201811095257A CN109134377A CN 109134377 A CN109134377 A CN 109134377A CN 201811095257 A CN201811095257 A CN 201811095257A CN 109134377 A CN109134377 A CN 109134377A
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- butyl
- methylimidazole
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- C—CHEMISTRY; METALLURGY
- 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
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Abstract
The invention belongs to technical field of organic synthesis, a kind of preparation method of ionic liquid is disclosed, including magnetic agitation, vacuum drying obtain intermediate product one at reaction conditions for step 1:1- methylimidazole and butyl bromide；Step 2: intermediate product one being configured to aqueous solution, with certain flow rate by chromatographic column, ion exchange is carried out, obtains intermediate product two；Step 3: titrating the concentration of intermediate product two to be measured with benchmark Potassium Hydrogen Phthalate solution, intermediate product two and ethanedioic acid are subjected to acid-base neutralization reaction；Step 4: obtained product vacuum is dry, obtain 1- butyl -3- methylimidazole oxalate.The preparation method obtains the higher ionic liquid of purity by the method for ion exchange resin.
Description
Technical field
The present invention relates to technical field of organic synthesis, more particularly, to a kind of preparation method of ionic liquid.
Background technique
Ionic liquid refers in room temperature or close to liquid, the salt as composed by zwitterion completely is presented at room temperature,
Referred to as low temperature molten salt is a kind of common green catalyst, at present the purity of the synthesis process intermediate ion liquid of ionic liquid
It is relatively low, catalytic efficiency is relatively low.
Notification number is that the document of 101768176 B of CN discloses a kind of ionic liquid, and the ionic liquid is by double oxalic acid boron
Acid esters lithium is constituted with the two class component of organic compound containing amido functionality, or addition organic solvent is by three classes component structure
At；Wherein double oxalic acid borate lithiums account for the 5%~70% of component gross mass, and organic solvent accounts for the 0 of volume components total content
~60%；Although the ionic liquid prepare it is simple, cheap, material easy purification, without vapour pressure, it is non-volatile, pollution-free,
Safety is good, and has preferable thermal stability, wider electrochemical window and higher ionic conductivity, but ionic liquid claims
Amount process is complicated, needs to operate in glove box, inconvenient for operation.
The document that notification number is 103635479 B of CN discloses ionic liquid Bao Han phosphonium salt, and the ionic liquid has not
The characteristics such as halogen atom, excellent heat stability and display hydrophobicity.In formula, R1 indicates the alkyl of carbon number 1-10, R2
Indicate that the alkyl of carbon number 8-20, R3 indicate that the alkyl of carbon number 1-8, n indicate the integer of 1-12.
The carbon number of R2 is more than the carbon number of R1, although the ionic liquid, the purity of the ionic liquid is lower.
Summary of the invention
In view of this, in view of the deficiencies of the prior art, it is an object of the present invention to provide a kind of preparation method of ionic liquid,
By the method for ion exchange resin, the higher ionic liquid of purity is obtained.
In order to achieve the above objectives, the invention adopts the following technical scheme:
A kind of preparation method of ionic liquid, comprising the following steps:
Step 1: by 1- methylimidazole and butyl bromide, magnetic agitation, product wash three with ethyl acetate at reaction conditions
Secondary, vacuum drying obtains 1- butyl -3- methylimidazole bromide；
Step 2: 1- butyl -3- methylimidazole bromide being configured to aqueous solution, which is passed through with certain flow rate equipped with work
In the chromatographic column for the ion exchange resin changed, carries out ion exchange and obtain 1- butyl -3- methylimidazole hydroxide；
Step 3: the concentration of 1- butyl -3- methylimidazole hydroxide is titrated with primary standard substance Potassium Hydrogen Phthalate solution, by 1-
Butyl -3- methylimidazole hydroxide and ethanedioic acid carry out acid-base neutralization reaction；
Step 4: the product for obtaining step 3 being rotated in a rotary evaporator and removes moisture, is put into five oxygen in a vacuum drying oven
Change two phosphorus and remove extra moisture, obtains 1- butyl -3- methylimidazole oxalate.
Further, the reaction condition of the step 1 is water bath with thermostatic control, is passed through nitrogen, is stirred to react, bath temperature is
70-90 DEG C, preferable temperature is 80-85 DEG C.
Further, the molar ratio of the N- methylimidazole and butyl bromide of the step 1 is 1:1.5, and preferred molar ratio is
1:1.1。
Further, the mass fraction of the 1- butyl -3- methylimidazole bromide in the aqueous solution in the step 2 is 60-
70%, preferably 70%.
Further, in the step 2, flow velocity is 10-50 ml/min, and preferable flow rate is 20-40 ml/min.
Further, in the step 2, ion exchange resin activate the step of it is as follows:
S1: impregnating 12-24h for ion exchange resin in clear water, until the as clear as crystal free from admixture of water, ion exchange resin is filled
Enter in chromatographic column；
S2: continuing the sodium hydroxide solution for being 3-5% with mass fraction and elute to the ion exchange resin in chromatographic column, leaching
Washing lotion is tested with silver nitrate and dilute nitric acid solution, up to no precipitating, stops elution；
S3: continue to rinse ion exchange resin 3-5 times with clear water.
Further, the molar ratio of the 1- butyl -3- methylimidazole hydroxide and ethanedioic acid in the step 3 is
2:1。
Further, vacuum drying temperature is 60-80 DEG C in the step 4, drying time 12-30h, preferably vacuum
Dry temperature is 70-75 DEG C, and preferred drying time is 24-28h.
The beneficial effects of the present invention are:
1, the present invention provides a kind of preparation method of ionic liquid, and the ion exchange resin of use activated is carried out to ionic liquid
Body intermediate 1- butyl -3- methylimidazole bromide carries out ion exchange, and the color of obtained ionic liquid is colourless, ionic liquid
Purity is higher, impure less, and carries out in chromatography exchange process carrying out ionic liquid, and bromide ion is by hydrogen in ionic liquid
Oxygen radical ion replaces.
2, the present invention a kind of preparation method of ionic liquid is provided, carry out 1- butyl -3- methylimidazole bromide titrate from
The process of sub-exchange resin can be tested using silver nitrate test solution and dilute nitric acid solution, be detected in ion exchange resin
Whether hydroxide ion is replaced completely by bromide ion.
3, the present invention provides a kind of preparation method of ionic liquid, wherein preparing the mistake of 1- butyl -3- methylimidazole bromide
Cheng Zhong, the molar ratio of strict control 1- methylimidazole and butyl bromide, the bath temperature of reaction, reaction temperature and inflated with nitrogen,
Guarantee that intermediate material 1- butyl -3- methylimidazole bromide purity is higher.
4, the present invention provides a kind of preparation method of ionic liquid, wherein in 1- butyl -3- methylimidazole bromide aqueous solution
It carries out in ion exchange resin ion exchange process, the dropwise addition of strict control 1- butyl -3- methylimidazole bromide aqueous solution is fast
Degree and dropwise addition ratio, the ionic liquid purity guaranteed is higher, and ion exchange capacity is bigger.
Specific embodiment
In order to make the object, technical scheme and advantages of the embodiment of the invention clearer, below in conjunction with the embodiment of the present invention,
The technical solution of the embodiment of the present invention is clearly and completely described.Obviously, described embodiment is of the invention one
Divide embodiment, instead of all the embodiments.Based on described the embodiment of the present invention, those of ordinary skill in the art are obtained
The every other embodiment obtained, shall fall within the protection scope of the present invention.
Embodiment 1
A kind of preparation method of ionic liquid, comprising the following steps:
Step 1:1- methylimidazole and butyl bromide are reacted in three-necked flask with molar ratio 1:1.1, and water bath with thermostatic control, magnetic force stir
Under the conditions of mixing, being condensed back, it is passed through nitrogen, bath temperature is 80 DEG C, obtains product and is washed three times with ethyl acetate, dry in vacuum
It is dried in vacuo under the conditions of 70 DEG C in dry case, obtains 1- butyl -3- methylimidazole bromide；
Step 2: obtained 1- butyl -3- methylimidazole bromide being configured to aqueous solution, is 60% aqueous solution with 20 by mass fraction
Ml/min passes through in the chromatographic column equipped with the ion exchange resin activated, carries out ion exchange and obtains 1- butyl -3- methyl miaow
Azoles hydroxide replaces the hydroxide ion in the ion exchange resin activated by bromide ion, this process, which is used, uses nitric acid
Silver-colored test solution and dilute nitric acid solution are tested.
Step 3: the concentration of 1- butyl -3- methylimidazole hydroxide is titrated with primary standard substance Potassium Hydrogen Phthalate solution,
1- butyl -3- methylimidazole hydroxide and ethanedioic acid are subjected to acid-base neutralization reaction with molar ratio for 2:1；
Step 4: the product of obtained step 3 being rotated in a rotary evaporator and removes moisture, is put into five in a vacuum drying oven
It aoxidizes two phosphorus and removes extra moisture, obtain 1- butyl -3- methylimidazole oxalate.Vacuum drying temperature is 70 DEG C, excellent
The drying time of choosing is obtained 1- butyl -3- methylimidazole oxalate for 24 hours.
The step of ion exchange resin activates is as follows:
S1: ion exchange resin being impregnated in clear water for 24 hours, until the as clear as crystal free from admixture of water, ion exchange resin is packed into
In chromatographic column；
S2: continuing the sodium hydroxide solution for being 3-5% with mass fraction and elute to the ion exchange resin in chromatographic column, leaching
Washing lotion is tested with silver nitrate and dilute nitric acid solution, up to no precipitating, stops elution；
S3: continue to rinse ion exchange resin 5 times with clear water.
Embodiment 2
A kind of preparation method of ionic liquid, comprising the following steps:
Step 1:1- methylimidazole and butyl bromide are reacted in three-necked flask with molar ratio 1:1.2, and water bath with thermostatic control, magnetic force stir
Under the conditions of mixing, being condensed back, it is passed through nitrogen, bath temperature is 85 DEG C, obtains product and is washed three times with ethyl acetate, dry in vacuum
It is dried in vacuo under the conditions of 70 DEG C in dry case, obtains 1- butyl -3- methylimidazole bromide；
Step 2: it is 65% aqueous solution that obtained 1- butyl -3- methylimidazole bromide, which is configured to concentration, is 65% by mass fraction
The aqueous solution is passed through with 20 ml/min in the chromatographic column equipped with the ion exchange resin activated, is carried out ion exchange and is obtained 1-
Butyl -3- methylimidazole hydroxide；
Step 3: the concentration of 1- butyl -3- methylimidazole hydroxide is titrated with primary standard substance Potassium Hydrogen Phthalate solution, by 1-
Butyl -3- methylimidazole hydroxide and ethanedioic acid are that 2:1 carries out acid-base neutralization reaction with molar ratio；
Step 4: step 3 product being rotated in a rotary evaporator and removes moisture, is put into phosphorus pentoxide in a vacuum drying oven
Extra moisture is removed, 1- butyl -3- methylimidazole oxalate is obtained.Vacuum drying temperature is 70 DEG C, preferred dry
Time is for 24 hours.Obtained 1- butyl -3- methylimidazole oxalate.
The step of ion exchange resin activates is as follows:
S1: impregnating 12h for ion exchange resin in clear water, until the as clear as crystal free from admixture of water, ion exchange resin is packed into
In chromatographic column；
S2: continue to elute the ion exchange resin in chromatographic column with the sodium hydroxide solution that mass fraction is 3%, elute
Liquid is tested with silver nitrate and dilute nitric acid solution, up to no precipitating, stops elution；
S3: continue to rinse ion exchange resin 4 times with clear water.
Embodiment 3
A kind of preparation method of ionic liquid, comprising the following steps:
Step 1:1- methylimidazole and butyl bromide are reacted in three-necked flask with molar ratio 1:1.3, and water bath with thermostatic control, magnetic force stir
Under the conditions of mixing, being condensed back, it is passed through nitrogen, bath temperature is 83 DEG C, obtains product and is washed three times with ethyl acetate, dry in vacuum
It is dried in vacuo under the conditions of 80 DEG C in dry case, obtains 1- butyl -3- methylimidazole bromide；
Step 2: it is 70% aqueous solution that obtained 1- butyl -3- methylimidazole bromide, which is configured to concentration, is 67% by mass fraction
The aqueous solution is passed through with 30 ml/min in the chromatographic column equipped with the ion exchange resin activated, is carried out ion exchange and is obtained 1-
Butyl -3- methylimidazole hydroxide；
Step 3: the concentration of 1- butyl -3- methylimidazole hydroxide is titrated with primary standard substance Potassium Hydrogen Phthalate solution, by 1-
Butyl -3- methylimidazole hydroxide and ethanedioic acid are that 2:1 carries out acid-base neutralization reaction with molar ratio；
Step 4: obtained step 3 product being rotated in a rotary evaporator and removes moisture, is put into five oxygen in a vacuum drying oven
Change two phosphorus and remove extra moisture, obtains 1- butyl -3- methylimidazole oxalate.Vacuum drying temperature is 70 DEG C, preferably
Drying time be for 24 hours.Obtained 1- butyl -3- methylimidazole oxalate.
The step of ion exchange resin activates is as follows:
S1: impregnating 12h for ion exchange resin in clear water, until the as clear as crystal free from admixture of water, ion exchange resin is packed into
In chromatographic column；
S2: continue to elute the ion exchange resin in chromatographic column with the sodium hydroxide solution that mass fraction is 5%, elute
Liquid is tested with silver nitrate and dilute nitric acid solution, up to no precipitating, stops elution；
S3: continue to rinse ion exchange resin 4 times with clear water.
Embodiment 4
A kind of preparation method of ionic liquid, comprising the following steps:
Step 1:1- methylimidazole and butyl bromide are reacted in three-necked flask with molar ratio 1:1.4, and water bath with thermostatic control, magnetic force stir
Under the conditions of mixing, being condensed back, it is passed through nitrogen, bath temperature is 83 DEG C, obtains product and is washed three times with ethyl acetate, dry in vacuum
It is dried in vacuo under the conditions of 70 DEG C in dry case, obtains 1- butyl -3- methylimidazole bromide；
Step 2: by obtained 1- butyl -3- methylimidazole bromide be configured to concentration be 60% aqueous solution, by the aqueous solution with
40ml/min passes through in the chromatographic column equipped with the ion exchange resin activated, carries out ion exchange and obtains 1- butyl -3- methyl
Imidazolium hydroxide；
Step 3: the concentration of 1- butyl -3- methylimidazole hydroxide is titrated with primary standard substance Potassium Hydrogen Phthalate solution, by 1-
Butyl -3- methylimidazole hydroxide and ethanedioic acid are that 2:1 carries out acid-base neutralization reaction with molar ratio；
Step 4: obtained 1- butyl -3- N-Methylimidazoleacetic salt is rotated in a rotary evaporator and removes moisture, it is dry in vacuum
It is put into phosphorus pentoxide in dry case and removes extra moisture, obtains 1- butyl -3- methylimidazole oxalate.Vacuum drying temperature
Degree is 72 DEG C, and preferred drying time is for 24 hours.Obtained 1- butyl -3- methylimidazole oxalate.
The step of ion exchange resin activates is as follows:
S1: impregnating 12h for ion exchange resin in clear water, until the as clear as crystal free from admixture of water, ion exchange resin is packed into
In chromatographic column；
S2: continue to elute the ion exchange resin in chromatographic column with the sodium hydroxide solution that mass fraction is 4%, elute
Liquid is tested with silver nitrate and dilute nitric acid solution, up to no precipitating, stops elution；
S3: continue to rinse ion exchange resin 4 times with clear water.
Embodiment 4
A kind of preparation method of ionic liquid, comprising the following steps:
Step 1:1- methylimidazole and butyl bromide are reacted in three-necked flask with molar ratio 1:1.5, and water bath with thermostatic control, magnetic force stir
Under the conditions of mixing, being condensed back, it is passed through nitrogen, bath temperature is 84 DEG C, obtains product and is washed three times with ethyl acetate, dry in vacuum
It is dried in vacuo under the conditions of 70 DEG C in dry case, obtains 1- butyl -3- methylimidazole bromide；
Step 2: obtained 1- butyl -3- methylimidazole bromide is configured to aqueous solution, will by mass fraction be 68% aqueous solution with
35ml/min passes through in the chromatographic column equipped with the ion exchange resin activated, carries out ion exchange and obtains 1- butyl -3- methyl
Imidazolium hydroxide；
Step 3: the concentration of 1- butyl -3- methylimidazole hydroxide is titrated with primary standard substance Potassium Hydrogen Phthalate solution, by 1-
Butyl -3- methylimidazole hydroxide and ethanedioic acid are that 2:1 carries out acid-base neutralization reaction with molar ratio；
Step 4: obtained 1- butyl -3- N-Methylimidazoleacetic salt is rotated in a rotary evaporator and removes moisture, it is dry in vacuum
It is put into phosphorus pentoxide in dry case and removes extra moisture, obtains 1- butyl -3- methylimidazole oxalate.Vacuum drying temperature
Degree is 75 DEG C, and preferred drying time is for 24 hours.Obtained 1- butyl -3- methylimidazole oxalate.
The step of ion exchange resin activates is as follows:
S1: impregnating 12h for ion exchange resin in clear water, until the as clear as crystal free from admixture of water, ion exchange resin is packed into
In chromatographic column；
S2: continue to elute the ion exchange resin in chromatographic column with the sodium hydroxide solution that mass fraction is 5%, elute
Liquid is tested with silver nitrate and dilute nitric acid solution, up to no precipitating, stops elution；
S3: continue to rinse ion exchange resin 4 times with clear water.
Embodiment 5
A kind of preparation method of ionic liquid, comprising the following steps:
Step 1:1- methylimidazole and butyl bromide are reacted in three-necked flask with molar ratio 1:1.5, and water bath with thermostatic control, magnetic force stir
Under the conditions of mixing, being condensed back, it is passed through nitrogen, bath temperature is 84 DEG C, obtains product and is washed three times with ethyl acetate, dry in vacuum
It is dried in vacuo under the conditions of 70 DEG C in dry case, obtains 1- butyl -3- methylimidazole bromide；
Step 2: obtained 1- butyl -3- methylimidazole bromide is configured to aqueous solution, by mass fraction be 70% aqueous solution with
35ml/min passes through in the chromatographic column equipped with the ion exchange resin activated, carries out ion exchange and obtains 1- butyl -3- methyl
Imidazolium hydroxide；
Step 3: the concentration of 1- butyl -3- methylimidazole hydroxide is titrated with primary standard substance Potassium Hydrogen Phthalate solution, by 1-
Butyl -3- methylimidazole hydroxide and ethanedioic acid are that 2:1 carries out acid-base neutralization reaction with molar ratio；
Step 4: obtained 1- butyl -3- N-Methylimidazoleacetic salt is rotated in a rotary evaporator and removes moisture, it is dry in vacuum
It is put into phosphorus pentoxide in dry case and removes extra moisture, obtains 1- butyl -3- methylimidazole oxalate.Vacuum drying temperature
Degree is 75 DEG C, and preferred drying time is for 24 hours.Obtained 1- butyl -3- methylimidazole oxalate.
The step of ion exchange resin activates is as follows:
S1: impregnating 12h for ion exchange resin in clear water, until the as clear as crystal free from admixture of water, ion exchange resin is packed into
In chromatographic column；
S2: continuing the sodium hydroxide solution for being 3-5% with mass fraction and elute to the ion exchange resin in chromatographic column, leaching
Washing lotion is tested with silver nitrate and dilute nitric acid solution, up to no precipitating, stops elution；
S3: continue to rinse ion exchange resin 4 times with clear water.
Finally, it is stated that the above examples are only used to illustrate the technical scheme of the present invention and are not limiting, this field is common
Other modifications or equivalent replacement that technical staff makes technical solution of the present invention, without departing from technical solution of the present invention
Spirit and scope, be intended to be within the scope of the claims of the invention.
Claims (8)
1. a kind of preparation method of ionic liquid, it is characterised in that: the following steps are included:
Step 1: by 1- methylimidazole and butyl bromide, magnetic agitation, product wash three with ethyl acetate at reaction conditions
Secondary, vacuum drying obtains 1- butyl -3- methylimidazole bromide；
Step 2: 1- butyl -3- methylimidazole bromide being configured to aqueous solution, aqueous solution is passed through with certain flow rate equipped with activation
In the chromatographic column for the ion exchange resin crossed, carries out ion exchange and obtain 1- butyl -3- methylimidazole hydroxide；
Step 3: the concentration of 1- butyl -3- methylimidazole hydroxide is titrated with primary standard substance Potassium Hydrogen Phthalate solution, by 1-
Butyl -3- methylimidazole hydroxide and ethanedioic acid acid-base neutralization reaction；
Step 4: the product of obtained step 3 being rotated in a rotary evaporator and removes moisture, is put into five in a vacuum drying oven
It aoxidizes two phosphorus and removes extra moisture, obtain 1- butyl -3- methylimidazole oxalate.
2. a kind of preparation method of ionic liquid according to claim 1, it is characterised in that: the reaction item of the step 1
Part is water bath with thermostatic control, is passed through nitrogen, is stirred to react, and bath temperature is 70-90 DEG C, and preferable temperature is 80-85 DEG C.
3. a kind of preparation method of ionic liquid according to claim 1, it is characterised in that: the N- methyl of the step 1
The molar ratio of imidazoles and butyl bromide is 1:1.5, preferred molar ratio 1:1.1.
4. a kind of preparation method of ionic liquid according to claim 1, it is characterised in that: water-soluble in the step 2
The mass fraction of 1- butyl -3- methylimidazole bromide in liquid be 60-70%, preferably 70%.
5. a kind of preparation method of ionic liquid according to claim 1, it is characterised in that: in the step 2, flow velocity is
10-50 ml/min, preferable flow rate are 20-40 ml/min.
6. a kind of preparation method of ionic liquid according to claim 1, it is characterised in that: in the step 2, ion is handed over
It is as follows to change resin activated step:
S1: impregnating 12-24h for ion exchange resin in clear water, until the as clear as crystal free from admixture of water, ion exchange resin is filled
Enter in chromatographic column；
S2: continuing the sodium hydroxide solution for being 3-5% with mass fraction and elute to the ion exchange resin in chromatographic column, leaching
Washing lotion is tested with silver nitrate and dilute nitric acid solution, up to no precipitating, stops elution；
S3: continue to rinse ion exchange resin 3-5 times with clear water.
7. a kind of preparation method of ionic liquid according to claim 1, it is characterised in that: described in the step 3
The molar ratio of 1- butyl -3- methylimidazole hydroxide and ethanedioic acid is 2:1.
8. a kind of preparation method of ionic liquid according to claim 1, it is characterised in that: vacuum is dry in the step 4
Dry temperature is 60-80 DEG C, drying time 12-30h, and preferably vacuum drying temperature is 70-75 DEG C, preferred drying time
For 24-28h.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111789120A (en) * | 2020-07-29 | 2020-10-20 | 湖南省植物保护研究所 | Bactericide imazalil ionic liquid, and preparation method and application thereof |
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| CN101033213A (en) * | 2007-03-30 | 2007-09-12 | 辽宁大学 | Phenylalanine-1-methyl-3-butyl-imidazole amino acid ionic liquid and preparing method thereof |
| CN102442950A (en) * | 2010-10-12 | 2012-05-09 | 中国科学院过程工程研究所 | Ionic liquid synthesis method based on strong alkaline anion exchange resin |
| CN102516177A (en) * | 2011-11-24 | 2012-06-27 | 南京大学 | Preparation method for high-purity ionic liquid |
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| CN101033213A (en) * | 2007-03-30 | 2007-09-12 | 辽宁大学 | Phenylalanine-1-methyl-3-butyl-imidazole amino acid ionic liquid and preparing method thereof |
| CN102442950A (en) * | 2010-10-12 | 2012-05-09 | 中国科学院过程工程研究所 | Ionic liquid synthesis method based on strong alkaline anion exchange resin |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111789120A (en) * | 2020-07-29 | 2020-10-20 | 湖南省植物保护研究所 | Bactericide imazalil ionic liquid, and preparation method and application thereof |
| CN111789120B (en) * | 2020-07-29 | 2022-04-01 | 湖南省植物保护研究所 | Bactericide imazalil ionic liquid, and preparation method and application thereof |
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