CN116396223A - Synthesis method of high-purity acetic acid imidazole ionic liquid - Google Patents
Synthesis method of high-purity acetic acid imidazole ionic liquid Download PDFInfo
- Publication number
- CN116396223A CN116396223A CN202310658651.9A CN202310658651A CN116396223A CN 116396223 A CN116396223 A CN 116396223A CN 202310658651 A CN202310658651 A CN 202310658651A CN 116396223 A CN116396223 A CN 116396223A
- Authority
- CN
- China
- Prior art keywords
- acetic acid
- ionic liquid
- imidazole
- solution
- acid type
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title claims abstract description 139
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims abstract description 129
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 36
- 238000001308 synthesis method Methods 0.000 title abstract description 6
- -1 imidazole cation halide Chemical class 0.000 claims abstract description 34
- 239000011347 resin Substances 0.000 claims abstract description 27
- 229920005989 resin Polymers 0.000 claims abstract description 27
- 239000000243 solution Substances 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000007864 aqueous solution Substances 0.000 claims abstract description 13
- 239000003957 anion exchange resin Substances 0.000 claims abstract description 12
- 239000011259 mixed solution Substances 0.000 claims abstract description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims abstract description 10
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000001450 anions Chemical class 0.000 claims abstract description 7
- 150000004820 halides Chemical class 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 238000010790 dilution Methods 0.000 claims abstract description 5
- 239000012895 dilution Substances 0.000 claims abstract description 5
- 230000002194 synthesizing effect Effects 0.000 claims description 12
- 238000004821 distillation Methods 0.000 claims description 8
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims description 6
- 229960003750 ethyl chloride Drugs 0.000 claims description 6
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims description 4
- 238000001514 detection method Methods 0.000 claims description 3
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 claims description 2
- 238000012797 qualification Methods 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- ZXLOSLWIGFGPIU-UHFFFAOYSA-N 1-ethyl-3-methyl-1,2-dihydroimidazol-1-ium;acetate Chemical compound CC(O)=O.CCN1CN(C)C=C1 ZXLOSLWIGFGPIU-UHFFFAOYSA-N 0.000 description 6
- FQERWQCDIIMLHB-UHFFFAOYSA-N 1-ethyl-3-methyl-1,2-dihydroimidazol-1-ium;chloride Chemical compound [Cl-].CC[NH+]1CN(C)C=C1 FQERWQCDIIMLHB-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000005342 ion exchange Methods 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- YSTQDJNWDMBAOZ-UHFFFAOYSA-N [Br].C(C)N1CN(C=C1)C Chemical compound [Br].C(C)N1CN(C=C1)C YSTQDJNWDMBAOZ-UHFFFAOYSA-N 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WWFKDEYBOOGHKL-UHFFFAOYSA-N 1-ethyl-3-methyl-1,2-dihydroimidazol-1-ium;bromide Chemical compound Br.CCN1CN(C)C=C1 WWFKDEYBOOGHKL-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940006460 bromide ion Drugs 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J47/00—Ion-exchange processes in general; Apparatus therefor
- B01J47/016—Modification or after-treatment of ion-exchangers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J47/00—Ion-exchange processes in general; Apparatus therefor
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- 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
Abstract
The invention belongs to the technical field of ionic liquid synthesis, and discloses a synthesis method of high-purity acetic acid imidazole ionic liquid, which comprises the following steps: reacting N-methylimidazole with halide to obtain imidazole cation halide mixed solution; purifying the mixed solution of the imidazole cationic halides, and then adding water for dilution to obtain the solution of the imidazole cationic halides; replacing anions in the anion exchange resin with acetate ions by adopting an acetic acid aqueous solution; and (3) enabling the imidazole cation halide solution to flow through acetate-substituted resin, replacing halogen anions of the imidazole cation halide with acetate ions to obtain acetic acid type imidazole ionic liquid, and concentrating the acetic acid type imidazole ionic liquid to obtain the imidazole cation ionic liquid. The acetic acid type imidazole ionic liquid with the purity of more than 99 percent can be prepared by adopting the method.
Description
Technical Field
The invention belongs to the technical field of ionic liquid synthesis, and particularly relates to a synthesis method of high-purity acetic acid imidazole ionic liquid.
Background
The statements herein merely provide background information related to the present disclosure and may not necessarily constitute prior art.
The ionic liquid is a liquid molten salt which consists of anions and cations and has a melting point of room temperature or below, and has unique physical and chemical properties, wherein the acetic acid type imidazole ionic liquid is favored by mild reaction performance, extremely strong dissolution capacity, excellent chemical stability and thermal stability. However, the purity of the acetic acid type imidazole ionic liquid prepared by the existing synthesis method is only 87% -90%, so that the use of the ionic liquid cannot be popularized.
Disclosure of Invention
Aiming at the defects existing in the prior art, the invention aims to provide a synthesis method of high-purity acetic acid type imidazole ionic liquid.
In order to achieve the above object, the present invention is realized by the following technical scheme:
a method for synthesizing high-purity acetic acid imidazole ionic liquid comprises the following steps:
reacting N-methylimidazole with halide to obtain imidazole cation halide mixed solution;
purifying the mixed solution of the imidazole cationic halides, and then adding water for dilution to obtain the solution of the imidazole cationic halides;
replacing anions in the anion exchange resin with acetate ions by adopting an acetic acid aqueous solution;
and (3) enabling the imidazole cation halide solution to flow through acetate-substituted resin, replacing halogen anions of the imidazole cation halide with acetate ions to obtain acetic acid type imidazole ionic liquid, and concentrating the acetic acid type imidazole ionic liquid.
The beneficial effects achieved by one or more embodiments of the present invention described above are as follows:
the acetic acid type imidazole ionic liquid with the purity of more than 99 percent can be prepared by adopting the method.
Detailed Description
It should be noted that the following detailed description is illustrative and is intended to provide further explanation of the invention. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
A method for synthesizing high-purity acetic acid imidazole ionic liquid comprises the following steps:
reacting N-methylimidazole with halide to obtain imidazole cation halide mixed solution;
purifying the mixed solution of the imidazole cationic halides, and then adding water for dilution to obtain the solution of the imidazole cationic halides;
replacing anions in the anion exchange resin with acetate ions by adopting an acetic acid aqueous solution;
and (3) enabling the imidazole cation halide solution to flow through acetate-substituted resin, replacing halogen anions of the imidazole cation halide with acetate ions to obtain acetic acid type imidazole ionic liquid, and concentrating the acetic acid type imidazole ionic liquid to obtain the imidazole cation ionic liquid.
The mixed solution of the imidazole cationic halides is easy to crystallize and solidify after being purified, and is more stable after being diluted by water.
The resin may be a C-217 anion exchange resin.
In some embodiments, the halide is selected from ethyl chloride, ethyl bromide, or butyl chloride.
In some embodiments, the mixed solution of imidazolium cations and halides is purified by distillation under reduced pressure. The purification efficiency can be improved.
In some embodiments, the mass percent of the imidazolium halide after dilution with water is 10% or less and 3% or more.
In some embodiments, the concentration of the aqueous acetic acid solution that anionically displaces the anion exchange resin is greater than or equal to 10% and less than or equal to 25%.
Preferably, the amount of the aqueous acetic acid solution is 4 to 8 times the volume of the resin.
Preferably, the flow rate of the aqueous acetic acid solution in the anion exchange resin is less than or equal to 45ml/min.
In some embodiments, the method further comprises the step of detecting a resin outlet solution parameter.
Preferably, the qualification index of the resin outlet solution parameter detection is: halogen ions account for less than 1% of the solute by mass.
The invention is further illustrated below with reference to examples.
Example 1
The synthesis of the 1-ethyl-3-methylimidazole acetate comprises the following steps:
(1) 100g of 1-methylimidazole and 133g of bromoethane are taken by a one-pot method, the bromoethane is dropwise added into the 1-methylimidazole at a constant speed under the condition of controlling the temperature to be 90 ℃, and the temperature is kept for 24 hours at 90 ℃ after the dropwise addition is finished.
(2) And (3) carrying out reduced pressure distillation on the solution obtained in the step (1), introducing high-purity nitrogen in the distillation process to improve the purification effect, controlling the vacuum degree to be-0.095 to-0.098 MPa, and treating for 60min at the oil bath temperature of 100 ℃ to obtain the high-purity 1-ethyl-3-methylimidazole bromide.
(3) Adding high-purity 1-ethyl-3-methylimidazole bromine salt into pure water to prepare the 1-ethyl-3-methylimidazole bromine salt water solution with the concentration of 3 percent.
(4) Adding resin with the volume of 75% of the volume of the chromatographic column into a C-217 type anion exchange resin with the diameter of 60mm and the height of 1000mm, carrying out conventional acid-base regeneration, flushing the resin to be neutral by pure water, carrying out ion exchange by flowing through the resin at a flow rate of 30ml/min by using a 10% concentration pure acetic acid aqueous solution with the volume of 5 times of the resin, and replacing anions in the resin with acetate ions to obtain the acetic acid type resin.
(5) The 3% strength 1-ethyl-3-methylimidazole bromine aqueous solution of step (3) was passed through the resin at a flow rate of 18ml/min for ion exchange.
(6) And (3) detecting ions in the resin discharge by adopting a bromide ion type ion meter, when the concentration of the bromide ions accounts for less than 1% of the mass percentage of the non-aqueous solution, starting to collect the outlet solution of the chromatographic column, and when the concentration of the bromide ions accounts for more than or equal to 1% of the mass percentage of the non-aqueous solution, stopping collecting.
The collected solution is concentrated to remove water (reduced pressure distillation) to obtain high-purity 1-ethyl-3-methylimidazole acetate, and the purity of the high-purity 1-ethyl-3-methylimidazole acetate is 99.7%.
Example 2
The synthesis of the 1-ethyl-3-methylimidazole acetate comprises the following steps:
(1) 100g of 1-methylimidazole and 79g of chloroethane are taken by a one-pot method, the chloroethane is introduced into the 1-methylimidazole at a constant speed under the condition of controlling the temperature to be 95 ℃, and the temperature is kept for 20 hours at 95 ℃ after the reaction is finished. The chloroethane is gas, and the chloroethane is introduced into the autoclave from the bottom of the autoclave by adopting a gas steel bottle and controlling proper pressure and flow rate to react.
(2) And (3) carrying out reduced pressure distillation on the solution obtained in the step (1), introducing high-purity nitrogen in the distillation process to improve the purification effect, controlling the vacuum degree to be-0.095 to-0.098 MPa, and treating for 60min at the oil bath temperature of 100 ℃ to obtain the high-purity 1-ethyl-3-methylimidazole chloride.
(3) Adding high-purity 1-ethyl-3-methylimidazole chloride into pure water to prepare 5% concentration 1-ethyl-3-methylimidazole chloride aqueous solution.
(4) Adding resin with the volume of 70% of the volume of the chromatographic column into a C-217 type anion exchange resin with the diameter of 60mm and the height of 1000mm, carrying out conventional acid-base regeneration, flushing the resin to be neutral by pure water, carrying out ion exchange by flowing through the resin at a flow rate of 40ml/min by using a pure acetic acid water solution with the concentration of 20% and the dosage of 6 times of the volume of the resin, and replacing anions in the resin with acetate ions to obtain the acetic acid type resin.
(5) The ion exchange is carried out by passing the 5% strength 1-ethyl-3-methylimidazole chloride aqueous solution of step (3) through the resin at a flow rate of 18 ml/min.
(6) And (3) adopting a chloride ion meter to perform ion detection on the resin discharge, when the chloride ion concentration is less than 1% of the mass percentage of the non-aqueous solution, starting to collect the chromatographic column outlet solution, and when the chloride ion concentration is more than or equal to 1% of the mass percentage of the non-aqueous solution, stopping collecting.
The collected solution is concentrated to remove water (reduced pressure distillation) to obtain high-purity 1-ethyl-3-methylimidazole acetate, and the purity of the high-purity 1-ethyl-3-methylimidazole acetate is 99.6%.
The above description is only of the preferred embodiments of the present invention and is not intended to limit the present invention, but various modifications and variations can be made to the present invention by those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A method for synthesizing high-purity acetic acid imidazole ionic liquid is characterized in that: the method comprises the following steps:
reacting N-methylimidazole with halide to obtain imidazole cation halide mixed solution;
purifying the mixed solution of the imidazole cationic halides, and then adding water for dilution to obtain the solution of the imidazole cationic halides;
replacing anions in the anion exchange resin with acetate ions by adopting an acetic acid aqueous solution;
and (3) enabling the imidazole cation halide solution to flow through acetate-substituted resin, replacing halogen anions of the imidazole cation halide with acetate ions to obtain acetic acid type imidazole ionic liquid, and concentrating the acetic acid type imidazole ionic liquid to obtain the imidazole cation ionic liquid.
2. The method for synthesizing the high-purity acetic acid type imidazole ionic liquid according to claim 1, which is characterized in that: the halide is selected from the group consisting of ethyl chloride, ethyl bromide, and butyl chloride.
3. The method for synthesizing the high-purity acetic acid type imidazole ionic liquid according to claim 1, which is characterized in that: and purifying the mixed solution of the imidazole cationic halides by adopting a reduced pressure distillation mode.
4. The method for synthesizing the high-purity acetic acid type imidazole ionic liquid according to claim 1, which is characterized in that: the mass percentage of the imidazole cationic halide after being diluted by water is less than or equal to 10 percent and more than or equal to 3 percent.
5. The method for synthesizing the high-purity acetic acid type imidazole ionic liquid according to claim 1, which is characterized in that: the concentration of the aqueous acetic acid solution for anion exchange resin is 10% or more.
6. The method for synthesizing the high-purity acetic acid type imidazole ionic liquid according to claim 5, which is characterized in that: the concentration of the aqueous acetic acid solution in which the anion exchange resin is anion-exchanged is 25% or less.
7. The method for synthesizing the high-purity acetic acid type imidazole ionic liquid according to claim 5, which is characterized in that: the amount of the aqueous acetic acid solution is 4-8 times of the volume of the resin.
8. The method for synthesizing the high-purity acetic acid type imidazole ionic liquid according to claim 5, which is characterized in that: the flow rate of the acetic acid aqueous solution in the anion exchange resin is less than or equal to 45ml/min.
9. The method for synthesizing the high-purity acetic acid type imidazole ionic liquid according to claim 1, which is characterized in that: further comprising the step of detecting a resin outlet solution parameter.
10. The method for synthesizing the high-purity acetic acid type imidazole ionic liquid according to claim 9, which is characterized in that: the qualification index of the resin outlet solution parameter detection is as follows: halogen ions account for less than 1% of the solute by mass.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202310658651.9A CN116396223A (en) | 2023-06-06 | 2023-06-06 | Synthesis method of high-purity acetic acid imidazole ionic liquid |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202310658651.9A CN116396223A (en) | 2023-06-06 | 2023-06-06 | Synthesis method of high-purity acetic acid imidazole ionic liquid |
Publications (1)
Publication Number | Publication Date |
---|---|
CN116396223A true CN116396223A (en) | 2023-07-07 |
Family
ID=87020196
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202310658651.9A Pending CN116396223A (en) | 2023-06-06 | 2023-06-06 | Synthesis method of high-purity acetic acid imidazole ionic liquid |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN116396223A (en) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100041869A1 (en) * | 2005-03-15 | 2010-02-18 | Mcgill University | Ionic liquid supported synthesis |
CN102190623A (en) * | 2011-03-25 | 2011-09-21 | 中国纺织科学研究院 | Method for preparing imidazole acetate ionic liquid |
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 |
-
2023
- 2023-06-06 CN CN202310658651.9A patent/CN116396223A/en active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100041869A1 (en) * | 2005-03-15 | 2010-02-18 | Mcgill University | Ionic liquid supported synthesis |
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 |
CN102190623A (en) * | 2011-03-25 | 2011-09-21 | 中国纺织科学研究院 | Method for preparing imidazole acetate ionic liquid |
Non-Patent Citations (1)
Title |
---|
尹旺: "咪唑类离子液体的合成及在纤维素水解中的应用研究", 中国优秀硕士学位论文全文数据库 工程科技I辑, vol. 2012, no. 2, pages 016 - 219 * |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
SE448636B (en) | Sodium chlorate prodn. by electrolysis of sodium chloride | |
JP5666196B2 (en) | Copper sulfate recovery method and copper sulfate recovery device | |
EP1966086B1 (en) | Method of purifying an aqueous solution | |
JPS6012344B2 (en) | How to treat acrylamide aqueous solution | |
CN102408309A (en) | Method for purifying glycerol waste liquid | |
CN105905914B (en) | A kind of preparation method of EHM extra high modulus silicate | |
CN116396223A (en) | Synthesis method of high-purity acetic acid imidazole ionic liquid | |
CN107117653A (en) | A kind of method for preparing high-purity ammonium poly-vanadate | |
CN101392417A (en) | Method for recovering ion liquid solvent from cellulose spinning by combination method | |
US11802060B2 (en) | Brine purification process | |
CN115925890A (en) | Method for purifying anti-new coronavirus neutralizing antibody | |
CN109336054A (en) | A method of recycling iodine from salt-making mother liquor | |
CN112480035A (en) | N-methylmorpholine and purification method thereof, methylmorpholine oxide and preparation method thereof | |
CN102675081B (en) | Preparation method of high-purity acetic acid | |
CN102190623A (en) | Method for preparing imidazole acetate ionic liquid | |
CN218944439U (en) | 1, 4-butynediol deionization system | |
CN115321559B (en) | Device and method for producing high-concentration sodium sulfate solution by nanofiltration membrane concentration technology | |
CN216472550U (en) | Device for removing silicon element in reactor coolant | |
CN101664612A (en) | Method for purifying and separating ionic liquid from water | |
JPH073485A (en) | Method for electrolyzing alkaline metal chloride | |
CN108658044A (en) | A kind of purification process of hydroiodic acid | |
CN111232928A (en) | Chlorine dioxide preparation and purification device and preparation method thereof | |
JP2001247305A (en) | Method for recovering boron | |
CN110003137B (en) | Method for removing impurities in HPPO (high pressure propylene oxide) process by using silane coupling agent modified material | |
CN105036080A (en) | Method for preparing high-concentration refined hydrochloric acid by using tail gas hydrogen chloride generated from chloroacetic acid production |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20230707 |