CN1060760C - Process for refining ethyl acetate and butanone from mixed solution containing ethyl acetate and butanone - Google Patents
Process for refining ethyl acetate and butanone from mixed solution containing ethyl acetate and butanone Download PDFInfo
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- CN1060760C CN1060760C CN97107722A CN97107722A CN1060760C CN 1060760 C CN1060760 C CN 1060760C CN 97107722 A CN97107722 A CN 97107722A CN 97107722 A CN97107722 A CN 97107722A CN 1060760 C CN1060760 C CN 1060760C
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Abstract
The present invention provides technology capable of refining ethyl acetate and butanone from a mixed solution containing ethyl acetate and butanone, wherein the mixed solution contains components such as water, ethanol, butanone, ethyl acetate, etc; boiling points of the ethyl acetate, the ethanol and the butanone in the components are extraordinarily similar; moreover, the ethyl acetate, the ethanol, the butanone and water mutually form binary azeotrope and ternary azeotrope with extraordinarily similar boiling points; the binary azeotrope and the ternary azeotrope can not be strictly separated by an ordinary rectification method. The technology adopts an extractive rectification method, and enhances mutual relative volatility among components under the action of an extraction solvent. Consequently, the ethyl acetate with high purity and the butanone with high purity are obtained.
Description
The present invention relates to be a kind of can be from the mixing solutions that contains ethyl acetate and butanone the technology of purified acetic acid ethyl ester and butanone, particularly be a kind of can be from the mixing solutions that is rich in ethyl acetate and butanone the novel process of purified acetic acid ethyl ester and butanone.
Be rich in the mixing solutions of ethyl acetate and butanone and contain components such as water, ethanol, butanone, ethyl acetate, wherein, ethyl acetate, ethanol, butanone three boiling point are very approaching, and ethyl acetate, ethanol, butanone, water form very approaching binary and the ternary azeotrope of boiling point between mutually, can't be with its strict separation with common rectificating method.
Be rich in the mixing solutions of ethyl acetate and butanone and contain ethyl acetate 20~60% (mol), contain butanone 1~50% (mol), all the other components are the second alcohol and water.
The boiling point of each component and its binary and ternary azeotropic are each other formed and boiling point following (seeing Table 1) in the mixing solutions: table 1:
The component title | Boiling point ℃ | Azeotrope boiling point ℃ | Azeotrope is formed (Wt%) |
Ethanol | 78.5 | 74.8 | 34 |
Butanone | 79.6 | 66 | |
Ethanol | 78.5 | 78.2 | 95.6 |
| 100 | 4.4 | |
Ethyl acetate | 77.2 | 77.0 | 82 |
Butanone | 79.6 | 18 | |
Ethyl acetate | 77.2 | 70.4 | 91.9 |
| 100 | 8.1 | |
Ethanol | 78.5 | 71.8 | 31 |
Ethyl acetate | 77.2 | 69 |
The component title | Boiling point ℃ | Azeotrope boiling point ℃ | Azeotrope is formed (Wt%) |
Butanone | 79.6 | 73.4 | 88 |
| 100 | 12 | |
Ethyl acetate | 77.2 | 70.2 | 82.6 |
Ethanol | 78.5 | 8.4 | |
| 100 | 9.0 | |
Ethanol | 78.5 | 73.2 | 14.0 |
Butanone | 79.6 | 75.0 | |
| 100 | 11.0 |
As can be seen from Table 1, ethyl acetate can't be refined to product specification with common rectificating method.
Domestic " modern chemical industry " reported " the separating technology research of single stage method synthesizing ethyl acetate " on 1996 11 phases, this process water is made solvent, take the extraction method that combines with extracting rectifying, ethyl acetate is separated from the mixture of moisture, acetaldehyde, ether, acetone, acetate, butanone, ethyl acetate.But the ethyl acetate purity that it obtains has only 93.2% (weight percent).
United States Patent (USP) has been described the method for isolating ethyl acetate by extracting rectifying from the second alcohol and water No. 4379028, and its extraction solvent that adopts is dimethyl sulfoxide (DMSO), N, dinethylformamide, ethylene glycol, propylene glycol and other mixed solvent.But do not contain butanone in its raw mix, and because the existence of butanone makes the highly purified ethyl acetate of acquisition difficulty more.
The processing method that United States Patent (USP) has been described by extracting rectifying isolating ethyl acetate from the second alcohol and water for No. 4569726, its extraction solvent that adopts is polyoxyethylene glycol, dipropylene glycol, glycol ether, triglycol, and their mixed solvent.But do not contain butanone in its raw mix equally.
United States Patent (USP) has been described the method for isolating ethyl acetate under anhydrous condition by extracting rectifying from butanone No. 4470881, its extraction solvent is 455 kinds of solvents and mixed solvent, but have only two kinds of components of ethyl acetate and butanone in its raw mix, and under anhydrous condition, carry out.
The object of the present invention is to provide a kind of extraction rectification technique method that can from contain ethyl acetate, ethanol, butanone, water mixed solution, make with extra care out the butanone of the ethyl acetate and 95~99.0% (mole) ((mol)) that concentration is 99.0% (mole) ((mol)).
The object of the present invention is achieved like this:
Technical process of the present invention (flow process 1) is as shown in Figure 1: contain ethyl acetate, ethanol, the mixing solutions of butanone and water is introduced as raw material by system, enter ethyl acetate tower middle part, extraction solvent adds from tower top, can contain 99% (mole) ethyl acetate product more than ((mol)) from the cat head extraction like this, extraction contains extraction solvent at the bottom of the tower, ethanol, the solution of butanone and water, enter the butanone rectifying tower, extraction solvent adds from tower top, the butanone that so just can contain 95~99% (mole) ((mol)) from the cat head extraction, extraction contains extraction solvent at the bottom of the tower, the solution of second alcohol and water, at last, this solution enters extraction solvent and reclaims rectifying tower, and purpose is to reclaim extraction solvent, from cat head recovered water and alcoholic acid mixture solution, extraction extraction solvent at the bottom of the tower recycles.
Mole (mol) inlet amount that enters the extraction solvent in the ethyl acetate tower in the above-mentioned technology (flow process 1) is 2~4 times of tower rising quantity of steam, reflux ratio is 3~6, the cat head produced quantity is about the amount of ethyl acetate in the raw material, mole (mol) inlet amount that enters the extraction solvent in the butanone rectifying tower is 2~5 times of the interior rising quantity of steam of tower, reflux ratio is 3~6, and the cat head produced quantity is about the amount of butanone in the charging.
The present invention also can adopt shown in the technical process as shown in Figure 2 (flow process 2): contain ethyl acetate, ethanol, the mixing solutions of butanone and water is by introducing outside the system as raw material, mix with the azeotrope that contains ethyl acetate from ethyl acetate recovery tower cat head distilled, enter the ethyl acetate tower, extraction solvent adds from tower top, can stay out from cat head like this and contain 99% (mole) ethyl acetate product more than ((mol)), extraction contains extraction solvent at the bottom of the tower, ethyl acetate, ethanol, the solution of butanone and water, then, this solution enters ethyl acetate and reclaims rectifying tower, purpose is to reclaim ethyl acetate wherein, utilize ethyl acetate and ethanol, butanone and water form the characteristic of the thing that boils, make ethyl acetate from the cat head extraction, return the ethyl acetate tower, circulation is reclaimed, extraction contains extraction solvent at the bottom of the tower, ethanol, the solution of butanone and water, enter the butanone rectifying tower, extraction solvent adds from tower top, the butanone that so just contains 95~99% (mole) ((mol)) from the cat head extraction, extraction contains extraction solvent at the bottom of the tower, the solution of second alcohol and water, at last, this solution enters extraction solvent and reclaims rectifying tower, purpose is to reclaim extraction solvent, from cat head recovered water and alcoholic acid mixture solution, extraction extraction solvent at the bottom of the tower recycles.
Mole (mol) inlet amount that above-mentioned technology (flow process 2) enters the extraction solvent in the ethyl acetate tower is 2~4 times of tower rising quantity of steam, reflux ratio is 3~6, the cat head produced quantity is about the amount of ethyl acetate in the raw material, mole (mol) inlet amount that enters the extraction solvent in the butanone rectifying tower is 2~5 times of the interior rising quantity of steam of tower, reflux ratio is 3~6, and the cat head produced quantity is about the amount of butanone in the charging.
The present invention also can adopt technical process (flow process 3) as shown in Figure 3: contain ethyl acetate, ethanol, the mixing solutions of butanone and water is by introducing outside the system as raw material, mix with the azeotrope that contains ethyl acetate from ethyl acetate product column overhead distilled, enter the ethyl acetate extraction rectifying tower, extraction solvent adds from tower top, extraction contains extraction solvent at the bottom of the tower, ethanol, the solution of butanone and water, contain 95% (mole) ethyl acetate more than ((mol)) from the cat head extraction, then, this solution enters the ethyl acetate product rectifying tower, purpose is further purified acetic acid ethyl ester, utilize ethyl acetate and ethanol, butanone and water form the characteristic of azeotrope, contain butanone from the cat head extraction, the azeotrope of water and ethyl acetate, returning the circulation of ethyl acetate extraction rectifying tower reclaims, extraction contains the ethyl acetate product of ethyl acetate 99% (mole) more than ((mol)) at the bottom of the tower, extraction contains extraction solvent at the bottom of the ethyl acetate extraction rectifying Tata, ethanol, the solution of butanone and water, enter the butanone rectifying tower, extraction solvent adds from tower top, the butanone that so just contains 95~99% (mole) ((mol)) from the cat head extraction, extraction contains extraction solvent at the bottom of the tower, the solution of second alcohol and water, at last, this solution enters extraction solvent and reclaims rectifying tower, purpose is to reclaim extraction solvent, from cat head recovered water and alcoholic acid mixture solution, extraction extraction solvent at the bottom of the tower recycles.
Mole (mol) inlet amount that enters the extraction solvent in the ethyl acetate extraction rectifying tower in the above-mentioned technology (flow process 3) is 2~4 times of the interior rising quantity of steam of tower, reflux ratio is 3~6, the cat head produced quantity is approximately greater than the amount of ethyl acetate in the raw material, mole (mol) inlet amount that enters the extraction solvent of butanone rectifying tower is 2~5 times of the interior rising quantity of steam of tower, reflux ratio is 3~6, and the cat head produced quantity is about the amount of butanone in the charging.
Process using extraction fractional distillation of the present invention by the processing condition of control tower, under the effect of extraction solvent, has increased component relative volatility each other, thereby has obtained highly purified ethyl acetate and butanone.
The extraction solvent that the present invention takes is acetonitrile, ethylene glycol, propylene glycol.
Technical process (flow process 1) is that with the difference of technical process (flow process 2) technical process (flow process 2) has increased an ethyl acetate and reclaimed rectifying tower, and operation control is more prone to.
Technical process (flow process 3) then from cat head with the whole extraction of ethyl acetate, by azeotropic distillation acetate acetate is purified again.Purpose also is that operation control is more prone to than technical process (flow process 1).
The effect of extraction solvent is to improve component relative volatility each other, particularly ethyl acetate the relative volatility of butanone can be brought up to more than 1.40 from 1.08, thereby reaches separation requirement (seeing Table 2).
Table 2:
Liquid phase is formed | Ethyl acetate | Ethanol | Butanone | Water | Ethylene glycol | α1 | α2 |
Liquid phase is formed vapour phase and is formed | 0.24615 0.82631 | 0.06944 0.11733 | 0.01302 0.03678 | 0.02281 0.01958 | 0.64858 | 1.188 | 1.672 |
Liquid phase is formed vapour phase and is formed | 0.13855 0.60615 | 0.16714 0.29601 | 0.02442 0.07841 | 0.02323 0.01943 | 0.64666 | 1.3625 | 1.813 |
Liquid phase is formed vapour phase and is formed | 0.11860 0.59992 | 0.16153 0.30680 | 0.02052 0.07415 | 0.02489 0.01866 | 0.67446 | 1.400 | 1.903 |
α 1 is the relative volatility of ethyl acetate to butanone in the table 2.
The present invention can make with extra care out acetic acid ethyl ester that concentration is 99% (mole) ((mol)) and 95~99.0% pure structures from contain ethyl acetate, ethanol, butanone, water mixed solution (butanone (mol), operation control easily.
Introduce embodiments of the invention below in conjunction with accompanying drawing:
Fig. 1 is technical process Fig. 1 of the present invention.
Fig. 2 is technical process Fig. 2 of the present invention.
Fig. 3 is technical process Fig. 3 of the present invention.
Embodiment 1:
Referring to Fig. 1, the mixing solutions that raw material is composed as follows enters ethyl acetate tower 1, and the earth material height of tower is 10M, for pressing court of a feudal ruler perforated plate corrugated filler, contains ethylene glycol 99.5% (mol) solvent and adds from filler top.Reflux ratio is 3, and cat head obtains ethyl acetate product.Each strand material is composed as follows:
Ethyl acetate ethanol butanone water glycol flow midship mol/h mixing solutions raw material 0.3440 0.5223 0.1160 0.0177/20 ethyl acetate product 0.9902 0.0000 0.0015 0.0083/6.9 ethylene glycol ///0.005 0.9950 60 tower bottoms forms 0.0006 0.1429 0.0314 0.0082 0.8169 73.1
The tower bottoms of ethyl acetate tower enters butanone tower 2, and the solvent that contains ethylene glycol 99.5% adds from filler top, and the packed height of tower is 10M, and reflux ratio is 4.The butanone solution that cat head extraction 95% (mole) ((mol)) is above, the tower still obtains the solution that contains extraction solvent, second alcohol and water composed as follows.
Ethyl acetate ethanol butanone water glycol flow mol/h butanone solution 0.0186 0.0046 0.9632 0.0136 2.2 tower bottomss are formed/0.0986 0.0017 0.0070 0.8927 105.9 ethylene glycol ///0.005 0.9950 35
The tower bottoms of butanone tower enters extraction solvent and reclaims rectifying tower 3 as raw material, and the packed height of tower is 7M, and reflux ratio is 1.Ethanol, butanone, the aqueous solution that the cat head extraction is composed as follows, the tower still obtains extraction distillation solvent.
Ethanol butanone water glycol flow mol/h overhead distillate 0.9595 0.0165 0.0240/10.88 tower bottomss // 0.0051 0.9949 95.02
Embodiment 2:
Referring to Fig. 2, the mixing solutions that raw material is composed as follows mixes with the azeotrope that contains ethyl acetate composed as follows, be preheated to 80 ℃, enter ethyl acetate tower 4, the packed height of tower is 10M, be protruded corrugated sheet packing, the solvent that contains ethylene glycol 99.5% adds from filler top.Reflux ratio is 3.5.Cat head obtains ethyl acetate product.Each strand material is composed as follows:
Ethyl acetate ethanol butanone water glycol flow mol/h mixed solution raw material 0.3440 0.5223 0.1160 0.0177/20 contains 0.4367 0.4221 0.1074 0.0338/2.5 azeotropic mixture ethyl acetate product, 0.9905 0.0000 0.0015 0.0080/6.92 ethylene glycol of ethyl acetate ///0.005 0.9950 60
Ethyl acetate tower tower bottoms composed as follows enters ethyl acetate recovery tower 5, and the packed height of tower is 10M, and reflux ratio is 8.The azeotrope that contains ethyl acetate composed as follows is from the cat head extraction, and the tower still obtains the solution that contains extraction solvent, ethanol, butanone and water composed as follows.
Ethyl acetate ethanol butanone water glycol flow mol/h feed composition (acetate 0.0148 0.1522 0.0341 0.0090 0.7899 75.58 acetate tower tower bottomss) contains 0.4367 0.4221 0.1074 0.0338/2.5 azeotrope tower bottomss of ethyl acetate and forms 0.0006 0.1429 0.0314 0.0082 0.8169 73.08
The tower bottoms of ethyl acetate recovery tower enters butanone tower 6 as raw material, and later on embodiment 1, the sequence number 7 among Fig. 2 is the solvent distillation recovery tower.
Embodiment 3:
Referring to Fig. 3, the mixing solutions that raw material is composed as follows mixes with the azeotrope that contains ethyl acetate composed as follows, enters ethyl acetate tower 8, and the packed height of tower is 10M, is protruded corrugated sheet packing, and the solvent that contains ethylene glycol 99.5% adds from tamping top.Reflux ratio is 3.5.Cat head obtains the thick product of ethyl acetate, and each strand material is composed as follows:
Ethyl acetate ethanol butanone water glycol flow mol/h mixed solution raw material 0.3440 0.5223 0.1160 0.0177/20 contains 0.7902 0.4221 0.1 074 0.0338/0.99 azeotropic mixture ethyl acetate crude product, 0.9724 0.0184 0.0078 0.0011/7.85 ethylene glycol of ethyl acetate ///0.005 0.9950 60
Then, the thick product of ethyl acetate enters ethyl acetate product rectifying tower 9, and the packed height of tower is 10M, and reflux ratio is 15.The azeotrope that contains ethyl acetate composed as follows is from the cat head extraction, and the tower still obtains ethyl acetate product.
Ethyl acetate ethanol butanone water glycol flow mol/h contains 0.7902 0.4221 0.1074 0.0338/0.99 azeotrope ethyl acetate product 0.9988 0.0000 0.0000 0.0012/6.86 of ethyl acetate
The tower bottoms of ethyl acetate tower enters butanone tower 10 as raw material, later on embodiment 1.Sequence number 11 among Fig. 3 is the solvent distillation recovery tower.
Extraction solvent in the various embodiments described above also can adopt acetonitrile or propylene glycol or other extraction solvent.
Claims (7)
1, a kind of from contain ethyl acetate and butanone mixing solutions purified acetic acid ethyl ester and butanone technology, it is characterized in that described technology comprises the steps:
A1, extracting rectifying ethyl acetate: the mixing solutions that contains ethyl acetate and ethanol and butanone and water, enter ethyl acetate tower middle part, extraction solvent adds from tower top, under the effect of extraction solvent, contain ethyl acetate product more than 99% volumetric molar concentration from the cat head extraction, extraction contains the solution of extraction solvent, ethanol, butanone and water at the bottom of the tower;
B1, the extracting rectifying butanone: the solution that contains extraction solvent, ethanol, butanone and water that comes from (a1) step enters butanone rectifying tower middle part, extraction solvent adds from tower top, under the effect of extraction solvent, contain the butanone of 95~99% volumetric molar concentrations from the cat head extraction, extraction contains the solution of extraction solvent, second alcohol and water at the bottom of the tower;
C1, extraction solvent reclaim: contain extraction solvent, water, alcoholic acid solution from what (b1) step was come, enter extraction solvent and reclaim the rectifying tower middle part, from cat head recovered water and alcoholic acid mixture solution, stay out extraction solvent at the bottom of tower, extraction solvent recycles.
2, as claimed in claim 1 from contain ethyl acetate and butanone mixing solutions purified acetic acid ethyl ester and butanone technology, it is characterized in that the described mole of feed amount that enters the extraction solvent in the ethyl acetate tower is 2~4 times of tower rising quantity of steam, reflux ratio is 3~6, the cat head produced quantity is about the amount of ethyl acetate in the raw material, the mole of feed amount that enters the extraction solvent in the butanone rectifying tower is 2~5 times of the interior rising quantity of steam of tower, reflux ratio is 3~6, and the cat head produced quantity is about the amount of butanone in the raw material.
3, a kind of from contain ethyl acetate and butanone mixing solutions purified acetic acid ethyl ester and butanone technology, it is characterized in that described technology comprises the steps:
A2, extracting rectifying ethyl acetate: the mixing solutions that contains ethyl acetate, ethanol, butanone and water, mix with the ethyl acetate azeotrope that contains that returns from (b2) step, enter ethyl acetate tower middle part, extraction solvent adds from cat head top, under the effect of extraction solvent, stay out the ethyl acetate product that contains more than 99% volumetric molar concentration from cat head, take to contain the solution of extraction solvent, ethyl acetate, ethanol, butanone and water at the bottom of the tower;
B2, ethyl acetate reclaims: from the next solution that contains extraction solvent, ethyl acetate, ethanol, butanone and water of (a2) step, enter ethyl acetate and reclaim the rectifying tower middle part, contain the ethyl acetate azeotrope from the cat head extraction, return step (a2), extraction contains the solution of extraction solvent, ethanol, butanone and water at the bottom of the tower;
C2, the extracting rectifying butanone: the solution that contains extraction solvent, ethanol, butanone and water that comes from (b2) step enters butanone rectifying tower middle part, extraction solvent adds from cat head top, under the effect of extraction solvent, contain the butanone of 95~99% volumetric molar concentrations from the cat head extraction, extraction contains the solution of extraction solvent, second alcohol and water at the bottom of the tower;
D2, extraction solvent reclaims; Contain extraction solvent, water, alcoholic acid solution from what (c2) step was come, enter extraction solvent and reclaim the rectifying tower middle part, from cat head recovered water and alcoholic acid mixture solution, stay out extraction solvent at the bottom of tower, extraction solvent recycles.
4, as claimed in claim 3 from contain ethyl acetate and butanone mixing solutions purified acetic acid ethyl ester and butanone technology, it is characterized in that the described mole of feed amount that enters the extraction solvent in the ethyl acetate tower is 2~4 times of the interior rising quantity of steam of tower, reflux ratio is 3~6, the cat head produced quantity is about the amount of ethyl acetate in the raw material, the mole of feed amount that enters the extraction solvent of butanone rectifying tower is 2~5 times of the interior rising quantity of steam of tower, reflux ratio is 3~6, and the cat head produced quantity is about the amount of butanone in the inlet amount.
5, a kind of from contain ethyl acetate and butanone mixing solutions purified acetic acid ethyl ester and butanone technology, it is characterized in that described technology comprises the steps:
A3, extracting rectifying ethyl acetate: the mixing solutions that contains ethyl acetate, ethanol, butanone and water, mix with the ethyl acetate azeotrope that contains that comes from (b3) step, enter ethyl acetate tower middle part, extraction solvent adds from cat head top, under the effect of extraction solvent, stay out ethyl acetate more than content 95% volumetric molar concentration from cat head, extraction contains the solution of extraction solvent, ethanol, butanone and water at the bottom of the tower;
B3, ethyl acetate product is refining: the ethyl acetate that contains more than 95% volumetric molar concentration of coming from (a3) step enters ethyl acetate product rectifying tower middle part, the azeotrope that contains butanone, water and ethyl acetate from the cat head extraction, return step (a3), extraction contains the ethyl acetate product more than ethyl acetate 99% volumetric molar concentration at the bottom of the tower;
C3, the extracting rectifying butanone: the solution that contains extraction solvent, ethanol, butanone and water that comes from (a3) step enters butanone rectifying tower middle part, extraction solvent adds from cat head top, under the effect of extraction solvent, contain the butanone of 95~99% volumetric molar concentrations from the cat head extraction, extraction contains the solution of extraction solvent, second alcohol and water at the bottom of the tower;
D3, extraction solvent reclaim: contain extraction solvent, water, alcoholic acid solution from what (C3) step was come, enter extraction solvent and reclaim rectifying tower, and from cat head recovered water and alcoholic acid mixture solution, extraction extraction solvent at the bottom of the tower, extraction solvent recycles.
6, as claimed in claim 5 from contain ethyl acetate and butanone mixing solutions purified acetic acid ethyl ester and butanone technology, it is characterized in that the described mole of feed amount that enters the extraction solvent in the ethyl acetate extraction rectifying tower is 2~4 times of the interior rising quantity of steam of tower, reflux ratio is 3~6, the cat head produced quantity is approximately greater than the amount of ethyl acetate in the raw material, the mole of feed amount that enters the extraction solvent in the butanone rectifying tower is 2~5 times of the interior rising quantity of steam of tower, reflux ratio is 3~6, and the cat head produced quantity is about the amount of butanone in the inlet amount.
7, as one of claim 1~6 described from contain ethyl acetate and butanone mixing solutions purified acetic acid ethyl ester and butanone technology, it is characterized in that described extraction solvent can adopt acetonitrile, ethylene glycol, propylene glycol.
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CN102180790B (en) * | 2011-03-11 | 2013-03-20 | 济南圣泉集团股份有限公司 | Method for removing water from ethyl acetate and butanone mixed solvent |
CN105130779B (en) * | 2015-08-06 | 2017-12-05 | 南通大学 | A kind of device and method for separating butanone, ethyl acetate and isopropanol water solution |
CN105622415B (en) * | 2016-02-18 | 2020-12-04 | 国药集团化学试剂有限公司 | Method for improving quality of ethyl acetate |
CN114716317B (en) * | 2022-05-20 | 2024-01-12 | 广东工业大学 | Method for separating ethyl acetate from aqueous solution by using eucalyptol |
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JPS5186392A (en) * | 1975-01-28 | 1976-07-28 | Seiko Instr & Electronics | HYOJISOCHINODENKYOKUKOZO |
JPS55115833A (en) * | 1979-02-28 | 1980-09-06 | Nittetsu Kakoki Kk | Separation of ester and ketone |
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JPS5186392A (en) * | 1975-01-28 | 1976-07-28 | Seiko Instr & Electronics | HYOJISOCHINODENKYOKUKOZO |
JPS55115833A (en) * | 1979-02-28 | 1980-09-06 | Nittetsu Kakoki Kk | Separation of ester and ketone |
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