CN114716317A - Method for separating ethyl acetate from aqueous solution by using eucalyptol - Google Patents
Method for separating ethyl acetate from aqueous solution by using eucalyptol Download PDFInfo
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- CN114716317A CN114716317A CN202210565881.6A CN202210565881A CN114716317A CN 114716317 A CN114716317 A CN 114716317A CN 202210565881 A CN202210565881 A CN 202210565881A CN 114716317 A CN114716317 A CN 114716317A
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- ethyl acetate
- eucalyptol
- mixture
- aqueous solution
- separating
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 title claims abstract description 219
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 title claims abstract description 44
- WEEGYLXZBRQIMU-WAAGHKOSSA-N Eucalyptol Chemical compound C1C[C@H]2CC[C@]1(C)OC2(C)C WEEGYLXZBRQIMU-WAAGHKOSSA-N 0.000 title claims abstract description 44
- 229960005233 cineole Drugs 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims abstract description 28
- 239000007864 aqueous solution Substances 0.000 title claims abstract description 22
- 238000000605 extraction Methods 0.000 claims abstract description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000000203 mixture Substances 0.000 claims description 23
- 239000000243 solution Substances 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 11
- 239000012535 impurity Substances 0.000 claims description 2
- 239000012071 phase Substances 0.000 claims 6
- 239000007791 liquid phase Substances 0.000 claims 1
- 239000002245 particle Substances 0.000 claims 1
- 239000010642 eucalyptus oil Substances 0.000 abstract description 8
- 229940044949 eucalyptus oil Drugs 0.000 abstract description 8
- 238000000926 separation method Methods 0.000 abstract description 4
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 238000005265 energy consumption Methods 0.000 abstract description 2
- 239000002351 wastewater Substances 0.000 abstract description 2
- 244000166124 Eucalyptus globulus Species 0.000 abstract 1
- 244000144972 livestock Species 0.000 abstract 1
- 238000012423 maintenance Methods 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 238000004817 gas chromatography Methods 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- 241000219927 Eucalyptus Species 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 240000008790 Musa x paradisiaca Species 0.000 description 1
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- RFFOTVCVTJUTAD-UHFFFAOYSA-N cineole Natural products C1CC2(C)CCC1(C(C)C)O2 RFFOTVCVTJUTAD-UHFFFAOYSA-N 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229940007062 eucalyptus extract Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000004434 industrial solvent Substances 0.000 description 1
- 239000010842 industrial wastewater Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Extraction Or Liquid Replacement (AREA)
Abstract
The invention discloses a method for separating ethyl acetate from an aqueous solution by using eucalyptol, which has the technical scheme that the method is a method for separating ethyl acetate from the aqueous solution at normal temperature by using eucalyptol (eucalyptol, main components of eucalyptus oil), wherein the eucalyptol is used as an extracting agent to extract the ethyl acetate from the aqueous solution, so that the ethyl acetate in water can be efficiently separated, the purity of the ethyl acetate is favorably maintained, the separation efficiency is improved, and the energy consumption of separation operation is favorably reduced; the simple extraction equipment is beneficial to improving the stability and reliability of the separation process and reducing the maintenance cost; because the eucalyptus oil is derived from eucalyptus and is a renewable resource, the eucalyptus oil is an environment-friendly, natural and harmless solvent to people and livestock, and the eucalyptol serving as a green extractant is beneficial to the treatment and purification of industrial organic wastewater and the protection of ecological environment, and simultaneously, the safety of the treated water body is improved.
Description
Technical Field
The invention relates to a method for separating ethyl acetate from an aqueous solution, in particular to a method for separating ethyl acetate from an aqueous solution by using eucalyptol.
Background
Eucalyptol, also known as eucalyptol, is a colorless transparent oily liquid with a camphor smell and herbal flavor. The eucalyptol has the molecular weight of 154.249g/mol, the CAS number of 470-82-6, the boiling point of 176 ℃, the melting point of 1-1.5 ℃, the freezing point of 1 ℃ and the flash point of 47-48 ℃. Soluble in ethanol, diethyl ether, chloroform, glacial acetic acid, glycerol and most of the non-volatile oils, chemically stable, slightly soluble in water. Eucalyptus oil is derived from eucalyptus, and is the main component of eucalyptus extract. The eucalyptus oil is extracted from the eucalyptus leaves by using a steam distillation method, is a natural green renewable solvent, and accords with the current industrial production strategy of sustainable development. At present, the research and industrial application of the eucalyptol (or the eucalyptus oil) in the aspect of ethyl acetate extraction are not found.
Ethyl acetate, also known as ethyl acetate, is a colorless transparent liquid, slightly sweet in taste, has pungent odor, and is a very important chemical raw material and industrial solvent. The ethyl acetate can be used in products such as paint, adhesive, ethyl cellulose and the like; has good bacteriostatic effect in certain medical aspects; can be used as main raw materials of various fruit essences and flavors such as pineapple, banana and the like; the method is widely applied to various fields of chemical industry.
Ethyl acetate has a certain solubility in water (for example, ethyl acetate is dissolved in water at 25 ℃ by 8.08%), in the production and use links of ethyl acetate, organic wastewater containing ethyl acetate is easily generated, and direct discharge of ethyl acetate not only wastes but also pollutes water. The binary (water + ethyl acetate) is an azeotrope system, the azeotropic temperature is 77.1 ℃ under normal pressure, and the azeotrope contains 6.1 percent of water, so the ethyl acetate-water system is separated by simple distillation, the ethyl acetate cannot be effectively separated, and the energy consumption in the rectification separation process is higher.
Disclosure of Invention
In view of the above, the present invention discloses a method for effectively separating ethyl acetate from an aqueous solution.
The invention also discloses an application of the method.
The purpose of the invention is realized by the following technical scheme:
a method for separating ethyl acetate from water solution by using eucalyptol comprises the following steps:
s1, pretreatment: removing impurities in the ethyl acetate aqueous solution to obtain a first mixture;
s2, extraction: adding eucalyptol to the first mixture to form a second mixture; stirring the second mixture, standing, and layering the second mixture to obtain an upper extract phase and a lower raffinate phase;
s3, separating the extract phase from the raffinate phase, and collecting the extract phase;
s4, separating the eucalyptol in the extraction phase to obtain ethyl acetate.
Further, in the above method for separating ethyl acetate from water, the ethyl acetate includes, but is not limited to, ethyl acetate.
Further, the volume ratio of the eucalyptol to the first mixture is 1: 1.
Through multiple experiments, the volume ratio of the eucalyptol to the first mixture is 1: 1, the extraction rate of the eucalyptol to the ethyl acetate in the first mixture is the highest, and the extraction rate cannot be further increased by continuously increasing the using amount of the eucalyptol, but the production cost is increased.
Further, in the step S2, the step of stirring the second mixture is to stir the second mixture at a rotation speed of 500rpm for 10min at normal temperature.
The inventor finds that the extraction effect of the eucalyptol in the second mixture on the ethyl acetate is stable, the method can achieve a good extraction effect under the condition of normal temperature, the change of the extraction effect is not obvious when the temperature is increased or reduced, and the method is not strong in temperature dependence. The method can achieve better extraction effect by stirring for 10min at the rotating speed of 500rpm, and the extraction effect is not remarkably changed by increasing the rotating speed and prolonging the time.
Further, the standing in S3 means that the second mixture is allowed to stand at normal temperature for 1 hour.
The invention also provides application of the method for separating ethyl acetate from the aqueous solution by using the eucalyptol (or the eucalyptus oil) in sewage treatment, ethyl acetate production and ethyl acetate recovery.
Compared with the prior art, the invention has the following advantages and beneficial effects:
(1) eucalyptol is chemically stable, slightly soluble in water, and is a renewable natural environment-friendly solvent.
(2) At 25 ℃, only 0.3 percent of eucalyptol can be dissolved in water, and the eucalyptol and the water are almost insoluble, so that the loss of the eucalyptol can be reduced to the minimum in the extraction process, and the reutilization rate of the eucalyptol is improved.
(3) The eucalyptus oil, namely the cineole, is rich in China and is derived from eucalyptus leaves, a large number of eucalypts are planted in China, but the eucalyptus leaves are usually directly discarded or burnt, and the method is favorable for utilizing the discarded eucalyptus leaves. The eucalyptol is selected as the extracting agent, so that the method is innovative and accords with the research of green and environmental protection.
(4) The eucalyptol has excellent extraction performance, and the method can effectively treat the industrial wastewater containing the ethyl acetate.
Drawings
FIG. 1 is a gas chromatogram before extraction of an aqueous ethyl acetate solution having a concentration of 20000ppm (20.0 g/L);
FIG. 2 is a gas chromatogram before extraction of an aqueous ethyl acetate solution having a concentration of 5000ppm (5.0 g/L);
FIG. 3 is a gas chromatogram before extraction of a 1000ppm (1.0g/L) aqueous ethyl acetate solution;
FIG. 4 is a gas chromatogram of an aqueous ethyl acetate solution having a concentration of 20000ppm (20.0g/L) extracted with eucalyptol;
FIG. 5 is a gas chromatogram of an aqueous solution of ethyl acetate at a concentration of 5000ppm (5.0g/L) after extraction with eucalyptol;
FIG. 6 is a gas chromatogram of an aqueous ethyl acetate solution having a concentration of 1000ppm (1.0g/L) after extraction with eucalyptol.
Detailed Description
The following claims are hereby incorporated into the detailed description of the invention, with the understanding that the invention is not to be limited in any way, as any number of modifications may be made by one within the scope of the claims and the invention is still within the scope of the claims.
Sample to be separated 1
Weighing 2.0g of ethyl acetate with the purity of more than or equal to 99.5 percent, adding the ethyl acetate into a 100ml volumetric flask, and adding deionized water to the volumetric flask to reach 100 ml. Under the condition of normal temperature, the rotating speed of a magnetic stirrer is 500rpm, the stirring is carried out until the ethyl acetate is completely dissolved in the water, no oil drop exists on the water surface, and the ethyl acetate water solution with the concentration of 20.0g/L before extraction is obtained. The ethyl acetate content was determined to be 20000ppm by gas chromatography.
Example 1
50ml of ethyl acetate aqueous solution in a sample 1 to be separated is taken and put into a balance kettle, 50ml of eucalyptol (purity 99 percent, the same below) is added, the rotation speed of a magnetic stirrer is 500rpm under the condition of normal temperature, the mixture is stirred for 10min, and the mixture is kept stand for 1 h. Standing, separating the lower raffinate phase from the clear upper and lower phases, and measuring the ethyl acetate content of the raffinate phase to 3052ppm by gas chromatography. The single stage extraction rate of process ethyl acetate was 84.7%.
25m of 1 of the ethyl acetate aqueous solution of the sample 1 to be separated is poured into a 100m1 volumetric flask, and deionized water is added to the flask to reach 100 ml. Under the condition of normal temperature, the rotating speed of the magnetic stirrer is 500 rpm. 5.0g/L of an aqueous ethyl acetate solution before extraction was obtained. The ethyl acetate solution was rated for 5000ppm by gas chromatography.
Example 2
And (3) taking 50ml of the ethyl acetate aqueous solution in the sample 2 to be separated, putting the 50ml of eucalyptol into a balance kettle, adding 50ml of eucalyptol, stirring for 10min at the normal temperature at the rotating speed of 500rpm of a magnetic stirrer, and standing for 1 h. Standing to obtain clear solution, separating the lower raffinate phase from the upper and lower phases, and measuring the content of ethyl acetate solution in the raffinate phase by gas chromatography to 580 ppm. The single stage extraction yield of process ethyl acetate was 88.4%.
Sample to be separated 3
And (3) taking 20ml of the ethyl acetate aqueous solution of the sample 2 to be separated, putting the ethyl acetate aqueous solution into a 100ml volumetric flask, and adding deionized water to the volume to be 100 ml. Under the condition of normal temperature, the rotating speed of the magnetic stirrer is 500 rpm. An aqueous ethyl acetate solution of 1.0g/L before extraction was obtained. The ethyl acetate solution content was calibrated to 1000ppm by gas chromatography.
Example 3
And (3) taking 50ml of ethyl acetate aqueous solution in the sample 3 to be separated, putting the 50ml of eucalyptol into a balance kettle, adding 50ml of eucalyptol, stirring for 10min at the normal temperature at the rotating speed of 500rpm of a magnetic stirrer, and standing for 1 h. Standing, separating the lower raffinate phase from the clear upper and lower phases, and measuring the ethyl acetate content in the raffinate phase by gas chromatography to be 170 ppm. The single-stage extraction rate of the process ethyl acetate was 83.0%.
Referring to FIG. 1, the specific chromatogram is a gas chromatogram before extraction of an ethyl acetate aqueous solution with the concentration of 20.0 g/L; the retention time is 1.89min as water peak, and 2.68min as ethyl acetate; FIG. 2 is a gas chromatogram before extraction of an aqueous ethyl acetate solution having a concentration of 5.0 g/L; the retention time is 1.89min as water peak, and 2.68min as ethyl acetate; FIG. 3 is a gas chromatogram before extraction of an aqueous ethyl acetate solution having a concentration of 1.0 g/L; the retention time was 1.87min for water peak and 2.66min for ethyl acetate. FIG. 4 is a gas chromatogram after extraction of an ethyl acetate-containing aqueous solution having a concentration of 20.0 g/L; the retention time is 1.89min as water peak, 2.66min as ethyl acetate, and 5.10min as eucalyptol; FIG. 5 is a gas chromatogram after extraction of an ethyl acetate-containing aqueous solution having a concentration of 5.0 g/L; the retention time is 1.87min as water peak, 2.67min as ethyl acetate, and 5.11min as eucalyptol; FIG. 6 is a gas chromatogram after extraction of an ethyl acetate-containing aqueous solution having a concentration of 1.0 g/L; the retention time is 1.87min as water peak, 2.66min as ethyl acetate, and 5.08min as eucalyptol.
The above is a detailed implementation of the present invention, but the present invention is not limited thereto. It will be apparent to those skilled in the relevant art that modifications may be made to the method in light of the above teachings and that such alternatives are within the scope of the invention.
Claims (4)
1. A method for separating ethyl acetate from water solution by using eucalyptol comprises the following steps:
s1, pretreatment: removing particle impurities in the ethyl acetate aqueous solution to obtain a first mixture;
s2, extraction: adding eucalyptol in a certain proportion into the first mixture to prepare a second mixture; standing the second mixture for 0.5-1.5h at normal temperature after stirring for 5-15min, and obtaining an upper extract phase and a lower raffinate phase after the second mixture is layered into two clear, transparent and stable liquid phases;
s3, separating the extraction phase from the raffinate phase, and collecting the extraction phase;
s4, separating the eucalyptol in the extraction phase to obtain ethyl acetate.
2. The method of claim 1, wherein: the volume ratio of eucalyptol to the first mixture is 1: 1.
3. The method of claim 1, wherein: the step of stirring the second mixture in S2 is to stir the second mixture for 10min at normal temperature with a magnetic stirrer rotating speed of 500 rpm.
4. The method of claim 1, wherein: the standing in S3 means that the second mixture is allowed to stand at the same temperature as the stirring temperature for 1 hour.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202210565881.6A CN114716317B (en) | 2022-05-20 | 2022-05-20 | Method for separating ethyl acetate from aqueous solution by using eucalyptol |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202210565881.6A CN114716317B (en) | 2022-05-20 | 2022-05-20 | Method for separating ethyl acetate from aqueous solution by using eucalyptol |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115231991A (en) * | 2022-07-31 | 2022-10-25 | 广东工业大学 | Method for separating isopropanol in aqueous solution by using eucalyptol and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1177591A (en) * | 1997-10-16 | 1998-04-01 | 化学工业部西南化工研究院 | Process for refining ethyl acetate and butanone from mixed solution containing ethyl acetate and butanone |
| CN105820035A (en) * | 2016-04-21 | 2016-08-03 | 广东工业大学 | Method for utilizing cycloalkanol in eucalyptol separation water solution and application of cycloalkanol |
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2022
- 2022-05-20 CN CN202210565881.6A patent/CN114716317B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1177591A (en) * | 1997-10-16 | 1998-04-01 | 化学工业部西南化工研究院 | Process for refining ethyl acetate and butanone from mixed solution containing ethyl acetate and butanone |
| CN105820035A (en) * | 2016-04-21 | 2016-08-03 | 广东工业大学 | Method for utilizing cycloalkanol in eucalyptol separation water solution and application of cycloalkanol |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115231991A (en) * | 2022-07-31 | 2022-10-25 | 广东工业大学 | Method for separating isopropanol in aqueous solution by using eucalyptol and application thereof |
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