CN112225634A - Method for separating cyclohexane and tert-butyl alcohol by liquid-liquid extraction-flash evaporation - Google Patents
Method for separating cyclohexane and tert-butyl alcohol by liquid-liquid extraction-flash evaporation Download PDFInfo
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- CN112225634A CN112225634A CN202011066657.XA CN202011066657A CN112225634A CN 112225634 A CN112225634 A CN 112225634A CN 202011066657 A CN202011066657 A CN 202011066657A CN 112225634 A CN112225634 A CN 112225634A
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- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 title claims abstract description 91
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims abstract description 31
- 239000007788 liquid Substances 0.000 title claims abstract description 21
- 238000001704 evaporation Methods 0.000 title claims abstract description 11
- 230000008020 evaporation Effects 0.000 title claims abstract description 11
- 238000000622 liquid--liquid extraction Methods 0.000 claims abstract description 34
- 238000000638 solvent extraction Methods 0.000 claims abstract description 34
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 24
- 238000000926 separation method Methods 0.000 claims abstract description 23
- 239000002608 ionic liquid Substances 0.000 claims abstract description 21
- 238000000605 extraction Methods 0.000 claims abstract description 7
- 239000000463 material Substances 0.000 claims abstract description 5
- 238000011084 recovery Methods 0.000 claims abstract description 5
- 238000004064 recycling Methods 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 24
- PXKPKGHXANCVMC-UHFFFAOYSA-N 3-butyl-1-methyl-1,2-dihydroimidazol-1-ium;trifluoromethanesulfonate Chemical compound OS(=O)(=O)C(F)(F)F.CCCCN1CN(C)C=C1 PXKPKGHXANCVMC-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- ULNIIYXAXLNRIE-UHFFFAOYSA-N cyclohexane;2-methylpropan-2-ol Chemical compound CC(C)(C)O.C1CCCCC1 ULNIIYXAXLNRIE-UHFFFAOYSA-N 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 claims description 2
- KAIPKTYOBMEXRR-UHFFFAOYSA-N 1-butyl-3-methyl-2h-imidazole Chemical compound CCCCN1CN(C)C=C1 KAIPKTYOBMEXRR-UHFFFAOYSA-N 0.000 claims description 2
- -1 1-butyl-3-methylimidazole dicyandiamide salt Chemical class 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 5
- 238000005265 energy consumption Methods 0.000 abstract description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 238000000895 extractive distillation Methods 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003254 gasoline additive Substances 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/005—Processes comprising at least two steps in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/86—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Abstract
The invention relates to a method for separating cyclohexane and tert-butyl alcohol by liquid-liquid extraction-flash evaporation and a device suitable for the method. According to the method, imidazole ionic liquid is used as an extracting agent, cyclohexane and tert-butyl alcohol firstly enter a liquid-liquid extraction tower for extraction and separation, high-purity cyclohexane is obtained at the top of the liquid-liquid extraction tower, materials at the bottom of the liquid-liquid extraction tower enter a flash tank for separation, high-recovery tert-butyl alcohol is obtained at the top of the flash tank, and high-purity ionic liquid is obtained at the bottom of the flash tank for recycling. The method has the advantages of low energy consumption, simple process, high purity of cyclohexane after separation and the like, the adopted imidazole ionic liquid serving as the extracting agent is almost non-volatile, the loss of the extracting agent is reduced, and the imidazole ionic liquid is easy to recover, good in chemical thermal stability, green and pollution-free.
Description
Technical Field
The invention belongs to the field of chemical separation and purification, and particularly relates to a method for separating a mixture of cyclohexane and tert-butyl alcohol by liquid-liquid extraction-flash evaporation, and further relates to a method for separating cyclohexane and tert-butyl alcohol by liquid-liquid extraction-flash evaporation by taking imidazole ionic liquid as an extracting agent and firstly adopting an extraction tower and then adopting a flash tank.
Background
Cyclohexane is useful as a solvent, binder diluent, and oil extractant for rubbers, paints, and varnishes. Tert-butanol is a widely used organic solvent. It is commonly used as a gasoline additive, a solvent for organic reaction processes, and a coating. The separation of tert-butanol and water during the co-oxidation of propylene/isobutane is a relatively difficult matter. For the tertiary butanol dehydration system, cyclohexane is typically selected as the entrainer. Thus, during the separation, a mixture of cyclohexane and tert-butanol is produced. It has been a question of how to separate the cyclohexane-tert-butanol azeotrope. At present, various methods for separating the azeotrope exist, such as pressure swing distillation, azeotropic distillation, extractive distillation and the like. Furthermore, liquid-liquid extraction is also an effective method. The ionic liquid is a room temperature liquid and is considered as a green environment-friendly solvent. In recent years, ionic liquids have attracted extensive attention of researchers due to their advantages of low volatility, environmental friendliness, good thermal stability, strong solubility, designability, and the like. These excellent properties make them highly effective functional compounds in many fields. In the field of separation and purification, ionic liquids are distinguished by their good solubility in organic and inorganic substances.
Cyclohexane and tert-butanol form an azeotrope with an azeotropic point of 71.91 ℃ at atmospheric pressure, wherein the mass fraction of cyclohexane is 66.74% and the mass fraction of water is 33.26%. Because of the existence of azeotrope in the mixture, the effective separation can not be realized by adopting the common rectification method.
Chinese patent CN103539663B discloses a method for separating ethyl acetate from cyclohexane, phenol is used as an extractant, and a mixture is separated by extractive distillation. However, the method adopts carcinogenic substance phenol as an extracting agent, and has great harm to human bodies and environment.
Chinese patent CN108976115A discloses a method for separating cyclohexane and acetic acid, which uses water as an entrainer, adopts an azeotropic distillation method to separate cyclohexane and acetic acid, and obtains cyclohexane with acetic acid content of 1-100 ppm at the tower top.
The prior cyclohexane treatment and separation technology has the problems of resource waste, high energy consumption, low removal rate and the like.
The invention adopts a liquid-liquid extraction-flash evaporation device to realize the high-purity recovery of cyclohexane in a cyclohexane-tert-butanol mixture, imidazole ionic liquid is taken as an extracting agent, and the characteristic of high solubility of tert-butanol in the extracting agent is utilized to realize that the purity of separated cyclohexane is up to more than 99.95 percent; the characteristic that the extracting agent has high boiling point and does not form an azeotrope with other substances is utilized, so that the extracting agent can be recycled, the separation cost is reduced, and the method has low energy consumption and simple process.
Disclosure of Invention
[ problem to be solved ]
The invention aims to provide a device for separating cyclohexane and tert-butyl alcohol by liquid-liquid extraction-flash evaporation.
It is another object of the present invention to provide a method for the liquid-liquid extraction-flash separation of cyclohexane and tert-butanol using said apparatus.
Another object of the present invention is to provide the use of imidazole-based ionic liquids as extractants in the liquid-liquid extraction-flash separation of cyclohexane and tert-butanol.
[ solution ]
The invention is realized by the following technical scheme.
A method for separating cyclohexane and tert-butyl alcohol by liquid-liquid extraction-flash evaporation is characterized in that a device for realizing the method mainly comprises the following parts: a liquid-liquid extraction column (LET), a flash tank (F1), a condenser (C1), a heater (H1) and a heater (H1); wherein the bottom of the liquid-liquid extraction column (LET) is connected with a heater (H1) and connected into a flash tank (F1);
the method for separating cyclohexane and tert-butyl alcohol by liquid-liquid extraction-flash evaporation by adopting the device comprises the following steps:
(1) the method comprises the following steps that a mixture of cyclohexane and tertiary butanol enters from the bottom of a liquid-Liquid Extraction Tower (LET), an extracting agent enters from the top of the liquid-Liquid Extraction Tower (LET), after effective contact extraction and separation, raffinate phase cyclohexane is produced as a product from the top of the liquid-Liquid Extraction Tower (LET), and a small amount of residual mixture of cyclohexane, extract phase tertiary butanol and the extracting agent enters a flash tank (F1) after being heated by a heater (H1) from the bottom of the liquid-Liquid Extraction Tower (LET);
(2) after the mixture is flashed by a flash tank (F1), the top material flow obtains a mixture of cyclohexane and tertiary butanol, the mixture is recycled, almost pure extractant is extracted from the bottom of the flash tank (F1), the material flow at the bottom of the flash tank (F1) enters a cooler (E1) for cooling, and then enters a liquid-liquid extraction column (LET) for recycling;
the extractant is imidazole ionic liquid.
According to another preferred embodiment of the invention, it is characterized in that: the operating pressure of the liquid-Liquid Extraction Tower (LET) is normal pressure, the number of tower plates is 5-15, the temperature of the liquid-Liquid Extraction Tower (LET) is 28-30.5 ℃, and the operating pressure of the flash tank (F1) is 0.01-0.02 atm.
According to another preferred embodiment of the invention, it is characterized in that: the extractant is imidazole ionic liquid and comprises 1-n-butyl-3-methylimidazole trifluoromethanesulfonate, 1-butyl-3-methylimidazole bis (trifluoromethanesulfonyl) imide, 1-butyl-3-methylimidazole dicyandiamide salt and other ionic liquid.
According to another preferred embodiment of the invention, it is characterized in that: the mass ratio of the feed flow of the extracting agent to the cyclohexane-tert-butyl alcohol mixture is 1-2.
According to another preferred embodiment of the invention, it is characterized in that: in the cyclohexane-tert-butanol binary mixed solution, the mass fraction of cyclohexane is 66.74%, and the mass fraction of water is 33.26%.
According to another preferred embodiment of the invention, it is characterized in that: the purity of the cyclohexane at the top of the extraction tower is higher than 99.95 percent, and the recovery rate of the tertiary butanol recovered by a flash tank (F1) is higher than 98 percent.
[ advantageous effects ]
Compared with the prior art, the invention mainly has the following beneficial effects:
(1) the method is adopted to separate the cyclohexane and the tertiary butanol, so that the cyclohexane with high purity and the tertiary butanol with high recovery rate are obtained, the high-purity component is obtained from the binary azeotropic mixture, and the problem that the cyclohexane and the tertiary butanol are difficult to separate is solved.
(2) The method has the advantages of simple process, less investment equipment and high purity of cyclohexane after separation, and the adopted imidazole ionic liquid as the extractant is easy to recover, has good chemical thermal stability, is green and has no pollution.
(3) The adopted extractant imidazole ionic liquid is almost non-volatile, the loss of the extractant is reduced, the secondary pollution of cyclohexane and tertiary butanol is avoided, in addition, the extractant is easy to recycle, and the separation cost is reduced.
Drawings
FIG. 1 is a process flow diagram of the present invention for liquid-liquid extraction-flash separation of cyclohexane and tert-butanol.
In the figure, LET-liquid extraction column; f1-flash tank; c1-condenser; h1-heaters, numbers representing the lines.
Detailed Description
Example 1:
the feed flow is 1000kg/h, the feed contains 66.74% of cyclohexane and 33.26% (mass fraction) of tertiary butanol, the theoretical plate number of a liquid-liquid extraction column (LET) is 5, a mixture of cyclohexane and tertiary butanol enters from the bottom of the liquid-liquid extraction column (LET), an extracting agent enters from the top of the liquid-liquid extraction column (LET), the extracting agent is 1-n-butyl-3-methylimidazole trifluoromethanesulfonate ionic liquid, the flow is 1600kg/h (the feed flow mass ratio of the extracting agent to the mixture of cyclohexane and tertiary butanol is 1.6), and the temperature of the liquid-liquid extraction column (LET) is 28 ℃. The flash tank (F1) was operated at 0.01bar with a cyclohexane purity of 99.96% after separation and a tert-butanol yield of 99.2%.
Example 2:
the feed flow is 1000kg/h, the feed contains 66.74% of cyclohexane and 33.26% (mass fraction) of tertiary butanol, the theoretical plate number of a liquid-liquid extraction column (LET) is 10, a mixture of cyclohexane and tertiary butanol enters from the bottom of the liquid-liquid extraction column (LET), an extracting agent enters from the top of the liquid-liquid extraction column (LET), the extracting agent is 1-n-butyl-3-methylimidazole trifluoromethanesulfonate ionic liquid, the flow is 1800kg/h (the feed flow mass ratio of the extracting agent to the mixture of cyclohexane and tertiary butanol is 1.6), and the temperature of the liquid-liquid extraction column (LET) is 29 ℃. The operating pressure of the flash tank (F1) was 0.015bar, the isolated phenol had a purity of 99.97% and the yield of tert-butanol was 99.2%.
Example 3:
the feed flow is 1000kg/h, the feed contains 66.74% of cyclohexane and 33.26% (mass fraction) of tertiary butanol, the theoretical plate number of a liquid-liquid extraction column (LET) is 15, a mixture of cyclohexane and tertiary butanol enters from the bottom of the liquid-liquid extraction column (LET), an extracting agent enters from the top of the liquid-liquid extraction column (LET), the extracting agent is 1-n-butyl-3-methylimidazole trifluoromethanesulfonate ionic liquid, the flow is 1900kg/h (the feed flow mass ratio of the extracting agent to the mixture of cyclohexane and tertiary butanol is 1.6), and the temperature of the liquid-liquid extraction column (LET) is 30.5 ℃. The operating pressure of the flash tank (F1) was 0.02bar, the isolated phenol had a purity of 99.97% and the yield of tert-butanol was 99.4%.
Claims (6)
1. A method for separating cyclohexane and tert-butyl alcohol by liquid-liquid extraction-flash evaporation is characterized in that a device for realizing the method mainly comprises the following parts: a liquid-liquid extraction column (LET), a flash tank (F1), a condenser (C1), and a heater (H1); wherein the bottom of the liquid-liquid extraction column (LET) is connected with a heater (H1) and connected into a flash tank (F1);
the method for separating cyclohexane and tert-butyl alcohol by liquid-liquid extraction-flash evaporation by adopting the device comprises the following steps:
(1) the method comprises the following steps that a mixture of cyclohexane and tertiary butanol enters from the bottom of a liquid-Liquid Extraction Tower (LET), an extracting agent enters from the top of the liquid-Liquid Extraction Tower (LET), after effective contact extraction and separation, raffinate phase cyclohexane is produced as a product from the top of the liquid-Liquid Extraction Tower (LET), a small amount of cyclohexane is remained, and a mixture of extract phase tertiary butanol and the extracting agent enters a flash tank (F1) after being heated by a heater (H1) from the bottom of the liquid-Liquid Extraction Tower (LET);
(2) after the mixture is flashed by a flash tank (F1), the top material flow obtains a mixture of cyclohexane and tertiary butanol, the mixture is recycled, almost pure extractant is extracted from the bottom of the flash tank (F1), the material flow at the bottom of the flash tank (F1) enters a cooler (E1) for cooling, and then enters a liquid-liquid extraction column (LET) for recycling;
the extractant is imidazole ionic liquid.
2. The liquid-liquid extraction-flash separation method of cyclohexane and tert-butanol according to claim 1, characterized in that: the operating pressure of the liquid-Liquid Extraction Tower (LET) is normal pressure, the number of tower plates is 5-15, the temperature of the liquid-Liquid Extraction Tower (LET) is 28-30.5 ℃, and the operating pressure of the flash tank (F1) is 0.01-0.02 atm.
3. The liquid-liquid extraction-flash separation method of cyclohexane and tert-butanol according to claim 1, characterized in that: the extractant is imidazole ionic liquid and comprises 1-n-butyl-3-methylimidazole trifluoromethanesulfonate, 1-butyl-3-methylimidazole bis (trifluoromethanesulfonyl) imide, 1-butyl-3-methylimidazole dicyandiamide salt and other ionic liquid.
4. The liquid-liquid extraction-flash separation method of cyclohexane and tert-butanol according to claim 1, characterized in that: the mass ratio of the feed flow of the extracting agent to the cyclohexane-tert-butyl alcohol mixture is 1-2.
5. The liquid-liquid extraction-flash separation method of cyclohexane and tert-butanol according to claim 1, characterized in that: in the cyclohexane-tert-butanol binary mixed solution, the mass fraction of cyclohexane is 66.74%, and the mass fraction of water is 33.26%.
6. The liquid-liquid extraction-flash separation method of cyclohexane and tert-butanol according to claim 1, characterized in that: the purity of the cyclohexane at the top of the extraction tower is higher than 99.95 percent, and the recovery rate of the tertiary butanol recovered by a flash tank (F1) is higher than 99.95 percent.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011066657.XA CN112225634A (en) | 2020-10-02 | 2020-10-02 | Method for separating cyclohexane and tert-butyl alcohol by liquid-liquid extraction-flash evaporation |
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| CN202011066657.XA CN112225634A (en) | 2020-10-02 | 2020-10-02 | Method for separating cyclohexane and tert-butyl alcohol by liquid-liquid extraction-flash evaporation |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113200820A (en) * | 2021-05-08 | 2021-08-03 | 青岛科技大学 | Method for separating dimethyl carbonate and methanol by using imidazole ionic liquid |
| CN113214049A (en) * | 2021-05-08 | 2021-08-06 | 青岛科技大学 | Method for separating isopropanol and isopropyl ether by liquid-liquid extraction-flash evaporation |
| CN114773157A (en) * | 2022-04-11 | 2022-07-22 | 桐乡市思远环保科技有限公司 | Method for separating and purifying tert-butyl alcohol by using ionic liquid |
-
2020
- 2020-10-02 CN CN202011066657.XA patent/CN112225634A/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| YING XU ET AL: "Mechanism Analysis for Separation of Cyclohexane and tert-Butanol System via Ionic Liquids as Extractants and Process Optimization", 《ACS SUSTAINABLE CHEMISTRY & ENGINEERING》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113200820A (en) * | 2021-05-08 | 2021-08-03 | 青岛科技大学 | Method for separating dimethyl carbonate and methanol by using imidazole ionic liquid |
| CN113214049A (en) * | 2021-05-08 | 2021-08-06 | 青岛科技大学 | Method for separating isopropanol and isopropyl ether by liquid-liquid extraction-flash evaporation |
| CN114773157A (en) * | 2022-04-11 | 2022-07-22 | 桐乡市思远环保科技有限公司 | Method for separating and purifying tert-butyl alcohol by using ionic liquid |
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Application publication date: 20210115 |