CN114716317B - 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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- CN114716317B CN114716317B CN202210565881.6A CN202210565881A CN114716317B CN 114716317 B CN114716317 B CN 114716317B CN 202210565881 A CN202210565881 A CN 202210565881A CN 114716317 B CN114716317 B CN 114716317B
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- ethyl acetate
- eucalyptol
- aqueous solution
- mixture
- separating
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 title claims abstract description 213
- 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 47
- 229960005233 cineole Drugs 0.000 title claims abstract description 47
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 239000007864 aqueous solution Substances 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000000605 extraction Methods 0.000 claims abstract description 36
- 239000000203 mixture Substances 0.000 claims description 22
- 238000003756 stirring Methods 0.000 claims description 7
- 239000012535 impurity Substances 0.000 claims description 2
- 239000012071 phase Substances 0.000 claims 6
- 239000007791 liquid phase Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 22
- 238000000926 separation method Methods 0.000 abstract description 5
- 239000010642 eucalyptus oil Substances 0.000 abstract description 4
- 229940044949 eucalyptus oil Drugs 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 3
- 230000009286 beneficial effect Effects 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
- 239000000243 solution Substances 0.000 description 14
- 241000219927 Eucalyptus Species 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 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
- 230000000844 anti-bacterial 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
- 238000011161 development Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 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
- 239000003205 fragrance Substances 0.000 description 1
- 239000008369 fruit flavor Substances 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
- 239000002075 main ingredient Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling 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
- 235000019605 sweet taste sensations Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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
Landscapes
- 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 in aqueous solution by using eucalyptol, which adopts the technical scheme that the method for separating ethyl acetate in the aqueous solution at normal temperature by using eucalyptol (main component of eucalyptol) is used as an extractant to extract ethyl acetate in 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 more favorably reduced; simple extraction equipment is beneficial to improving the stability and reliability of the separation process and reducing the maintenance cost; the eucalyptus oil is derived from eucalyptus and is a renewable resource, so that the eucalyptus oil is an environment-friendly, natural and harmless solvent for people and livestock, and the eucalyptol is taken as a green extractant, so that the treatment of the purified industrial organic wastewater and the protection of the ecological environment are facilitated, and 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, and has camphor smell and herb taste. The molecular weight of eucalyptol is 154.249g/mol, CAS number 470-82-6, boiling point of the eucalyptol is 176 ℃, melting point of the eucalyptol is 1-1.5 ℃, solidifying point of the eucalyptol is 1 ℃, and flash point of the eucalyptol is 47-48 ℃. Dissolved in ethanol, diethyl ether, chloroform, glacial acetic acid, glycerol and most of the non-volatile oils, chemically stable, and slightly soluble in water. Eucalyptus oil is derived from eucalyptus and is the main ingredient of eucalyptus extract. The eucalyptus oil is extracted from eucalyptus leaves by a steam distillation method, is a natural green renewable solvent, and accords with the industrial production strategy of sustainable development at present. No research and industrial application of eucalyptol (or eucalyptol) in ethyl acetate extraction are found.
Ethyl acetate, also called ethyl acetate, is a colorless transparent liquid, has slightly sweet taste and pungent smell, and is a very important chemical raw material and industrial solvent. Ethyl acetate can be used in products such as paint, adhesive, ethyl cellulose and the like; has good antibacterial effect in certain medicine aspects; can be used as main raw materials of various fruit flavors and fragrances such as pineapple, banana and the like; is widely applied to various fields of chemical industry.
The ethyl acetate has certain solubility in water (for example, the ethyl acetate is dissolved in the water at 25 ℃ for 8.08%), organic wastewater containing the ethyl acetate is easy to generate in the production and use links of the ethyl acetate, and the direct discharge of the ethyl acetate not only can waste, but also can pollute the water body. Binary (water and 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 that the ethyl acetate-water system can not be effectively separated by simple distillation, and the energy consumption in the rectification separation process is higher.
Disclosure of Invention
In view of this, the present invention discloses a process for efficiently separating ethyl acetate from an aqueous solution.
The invention also discloses application of the method.
The aim of the invention is achieved by the following technical scheme:
a method for separating ethyl acetate from an aqueous solution by using eucalyptol, comprising the steps of:
s1, pretreatment: removing impurities in the ethyl acetate aqueous solution to obtain a first mixture;
s2, extracting: adding eucalyptol to the first mixture to prepare a second mixture; stirring the second mixture, standing, and layering the second mixture to obtain an upper extraction phase and a lower raffinate phase;
s3, separating an extraction phase from a raffinate phase, and collecting the extraction phase;
s4, separating eucalyptol in the extract phase to obtain ethyl acetate.
Further, the above-mentioned ethyl acetate aqueous solution separation method, wherein the ethyl acetate includes but is not limited to ethyl acetate.
Further, the volume ratio of 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 dosage of the eucalyptol, but the production cost is increased.
Further, stirring the second mixture in S2 means stirring the second mixture at room temperature at 500rpm for 10min.
The inventor finds that the extraction effect of eucalyptol in the second mixture on ethyl acetate is stable, the method can achieve better 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 has weak dependence on the temperature. The method can achieve better extraction effect by stirring for 10min at the rotation speed of 500rpm, and the change of the extraction effect is not obvious due to the increase of the rotation speed and the prolonged time.
Further, the standing in S3 means that the second mixture is left standing at normal temperature for 1h.
The invention also provides application of the method for separating ethyl acetate from the aqueous solution by using eucalyptol (or eucalyptol) in sewage treatment, ethyl acetate production and ethyl acetate recovery.
Compared with the prior art, the invention has the following advantages:
(1) The eucalyptol is stable in alcohol and slightly soluble in water, and is a renewable natural environment-friendly solvent.
(2) Only 0.3% of eucalyptol can be dissolved in water at 25 ℃, and the eucalyptol and water are hardly mutually dissolved, so that the loss of eucalyptol can be reduced to the minimum in the extraction process, and the recycling rate of eucalyptol is improved.
(3) The eucalyptus oil-cineole is abundant in China and is derived from eucalyptus leaves, a large amount of eucalyptus is planted in China, but the eucalyptus leaves are often directly discarded or burnt, and the invention is beneficial to utilizing discarded eucalyptus She Feiwu. The eucalyptol is selected as the extractant, which is innovative and meets the green and environment-friendly research.
(4) The eucalyptol has excellent extraction performance, and the invention can effectively treat industrial wastewater containing ethyl acetate.
Drawings
FIG. 1 is a gas chromatogram before extraction with 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 with an aqueous ethyl acetate solution having a concentration of 1000ppm (1.0 g/L);
FIG. 4 is a gas chromatogram after extraction of an aqueous ethyl acetate solution having a concentration of 20000ppm (20.0 g/L) with eucalyptol;
FIG. 5 is a gas chromatogram after extraction of an aqueous ethyl acetate solution at a concentration of 5000ppm (5.0 g/L) with eucalyptol;
FIG. 6 is a gas chromatogram of an aqueous ethyl acetate solution at a concentration of 1000ppm (1.0 g/L) after extraction with eucalyptol.
Detailed Description
The following claims are presented in further detail in connection with the detailed description, but are not to be construed as limiting the invention, as any person who makes a limited number of modifications within the scope of the claims is within the scope of the claims.
Sample 1 to be separated
2.0g of ethyl acetate with the purity of more than or equal to 99.5 percent is weighed and added into a 100ml volumetric flask, and deionized water is added to fix the volume to 100ml. Under normal temperature, the rotation speed of the magnetic stirrer is 500rpm, and the magnetic stirrer is stirred until the ethyl acetate is completely dissolved in water, and no oil drop exists on the water surface, so that the ethyl acetate aqueous solution with the concentration of 20.0g/L before extraction is obtained. The ethyl acetate content was calibrated to 20000ppm by gas chromatography.
Example 1
50ml of the ethyl acetate aqueous solution in the sample 1 to be separated was placed in an equilibrium kettle, 50ml of eucalyptol (purity 99%, the same applies below) was added, and the stirring was carried out at a magnetic stirrer rotation speed of 500rpm at room temperature for 10min and allowed to stand for 1h. After standing, the solution is clear and transparent, the upper phase and the lower phase are separated, and the ethyl acetate content in the raffinate phase is 3052ppm by using a gas chromatography method. The single-stage extraction rate of the ethyl acetate in the process is 84.7%.
Sample 2 to be separated
The ethyl acetate aqueous solution of the sample 1 to be separated is taken to be 25m1, injected into a volumetric flask of 100m1, and deionized water is added to fix the volume to 100ml. The magnetic stirrer rotation speed was 500rpm at normal temperature. An aqueous solution of ethyl acetate of 5.0g/L before extraction was obtained. The ethyl acetate solution content was calibrated to 5000ppm by gas chromatography.
Example 2
50ml of the ethyl acetate aqueous solution in the sample 2 to be separated is put into a balance kettle, 50ml of eucalyptol is added, and the mixture is stirred for 10min under the condition of normal temperature and the rotating speed of a magnetic stirrer is 500rpm and is kept stand for 1h. After standing, the solution is clear and transparent, the upper phase and the lower phase are separated, and the ethyl acetate solution content in the raffinate phase is 580ppm by gas chromatography. The single-stage extraction rate of the ethyl acetate in the process is 88.4 percent.
Sample 3 to be separated
The ethyl acetate aqueous solution of the sample 2 to be separated is taken to 20ml and put into a 100ml volumetric flask, and deionized water is added to fix the volume to 100ml. The magnetic stirrer rotation speed was 500rpm at normal temperature. An aqueous solution of ethyl acetate of 1.0g/L before extraction was obtained. The ethyl acetate solution content was calibrated to 1000ppm by gas chromatography.
Example 3
50ml of the ethyl acetate aqueous solution in the sample 3 to be separated is put into a balance kettle, 50ml of eucalyptol is added, and the mixture is stirred for 10min under the condition of normal temperature and the rotating speed of a magnetic stirrer is 500rpm and is kept stand for 1h. After standing, the solution is clear and transparent, the upper phase and the lower phase are separated, and the ethyl acetate content in the raffinate phase is 170ppm by using a gas chromatography method. The single-stage extraction rate of ethyl acetate in the process is 83.0%.
Specific chromatograms, refer to figure 1, are gas chromatograms before extraction of ethyl acetate aqueous solution with concentration of 20.0 g/L; the retention time was 1.89min as the water peak and 2.68min as ethyl acetate; FIG. 2 is a gas chromatogram before extraction with an aqueous ethyl acetate solution having a concentration of 5.0 g/L; the retention time was 1.89min as the water peak and 2.68min as ethyl acetate; FIG. 3 is a gas chromatogram before extraction with an aqueous ethyl acetate solution at a concentration of 1.0 g/L; the retention time was 1.87min as the water peak and 2.66min as ethyl acetate. FIG. 4 is a gas chromatogram after extraction of an aqueous solution containing ethyl acetate at 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 aqueous solution containing ethyl acetate at 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 aqueous solution containing ethyl acetate at a concentration of 1.0 g/L; the retention time was 1.87min as the water peak, 2.66min as ethyl acetate and 5.08min as eucalyptol.
The foregoing is a detailed implementation of the invention, but is not meant to limit the invention to such. Modifications of the method will continue to be apparent to those skilled in the relevant art in light of the present teachings, and such alternatives are intended to be within the scope of the present teachings.
Claims (3)
1. A method for separating ethyl acetate from an aqueous solution by using eucalyptol, comprising the steps of:
s1, pretreatment: removing particulate impurities from the ethyl acetate aqueous solution to obtain a first mixture;
s2, extracting: adding a certain proportion of eucalyptol into the first mixture to prepare a second mixture; stirring the second mixture for 5-15 min at normal temperature, standing for 0.5-1.5. 1.5 h, and layering the second mixture into two clear transparent and stable liquid phases to obtain an upper extraction phase and a lower extraction phase;
s3, separating an extraction phase from a raffinate phase, and collecting the extraction phase;
s4, separating eucalyptol in the extraction phase to obtain ethyl acetate;
the volume ratio of eucalyptol to the first mixture is 1:1.
2. The method according to claim 1, characterized in that: in the step S2, the second mixture is stirred for 10min at normal temperature with the rotation speed of a magnetic stirrer of 500rpm.
3. The method according to claim 1, characterized in that: the standing in S2 means that the second mixture is left standing at the same temperature as the stirring temperature for 1 hour.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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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| Publication Number | Publication Date |
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| CN114716317A CN114716317A (en) | 2022-07-08 |
| CN114716317B true CN114716317B (en) | 2024-01-12 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| 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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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 |
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