CN103274931A - Solvent for separating carboxylic acid mixtures by extraction and rectification - Google Patents
Solvent for separating carboxylic acid mixtures by extraction and rectification Download PDFInfo
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- CN103274931A CN103274931A CN2013102204545A CN201310220454A CN103274931A CN 103274931 A CN103274931 A CN 103274931A CN 2013102204545 A CN2013102204545 A CN 2013102204545A CN 201310220454 A CN201310220454 A CN 201310220454A CN 103274931 A CN103274931 A CN 103274931A
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- acetate
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- 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
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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Abstract
The invention discloses a solvent for separating carboxylic acid mixtures by extraction and rectification. The solvent is mainly composed of ionic liquid. The solvent can be absolute ionic liquid and also can be a mixture of ionic liquid and preparation materials of cations and anions thereof. The cations of ionic liquid are organic amine. The anions are carboxyl groups. The solvent for extracting, rectifying and separating carboxylic acid mixtures can raise the relative volatilities among components, can raise the separation efficiency, and can reduce the production cost.
Description
Technical field
The present invention relates to a kind of solvent that separates mixture of carboxylic acids, specifically, is the solvent of a kind of extracting rectifying separation carboxylic acid-water and carboxylic acid-carboxylicesters, carboxylic acid-alcohol, carboxylic acid-ketone, carboxylic acid-aldehyde mixture.。
Background technology
Have a large amount of mixtures that contains carboxylic acid and produce in the production of carboxylic acid and use, though they can not form azeotrope, relative volatility is separated comparatively difficulty close to 1, adopts the method for conventional distillation and azeotropic distillation more.Conventional distillation technology simply is easy to control, but required stage number is more, and energy consumption is big, and the required stage number of azeotropic distillation is less, but the consumption of entrainer is big, and configuration is complicated, and operation control is comparatively complicated.
Extracting rectifying has become one of separation method important in the chemical industry, and its application is more and more general, and the performance of solvent plays crucial effects to sepn process in the selected extracting rectifying.
US5167774 and US4729848 disclose the method separating acetic acid of taking extracting rectifying and the mixture of water, the former selects for use tetramethylene sulfone, adiponitrile as solvent, the latter selects for use oil of mirbane, methyl phenyl ketone, positive enanthic acid etc. as solvent, this method selection of Extractant scope is wide, operation is easy to control, and separating effect is better than conventional distillation and azeotropic distillation, but has the extraction agent large usage quantity, the plate number is many, the weakness that energy consumption is big.
CN101306989B discloses a kind of method of extractive distillation with salt acetic acid water mixture, and this method separation efficiency is higher, and stage number is few, and energy consumption is less, thereby but the easy crystallization of inorganic salt that adds separate out and can stop up column plate, column plate is caused corrosion.
Summary of the invention
Be difficult to separate relative volatility near the problem of 1 mixture of carboxylic acids with the method for rectifying in order to solve, the invention provides a kind of solvent that extracting rectifying separates mixture of carboxylic acids that can be used for, can improve the relative volatility between mixture, improve separation efficiency, cut down the consumption of energy.
The solvent that can be used for the extracting rectifying vinegar stock provided by the invention is that organic amine, negatively charged ion are that the ionic liquid of carboxylate radical is main ingredient with the positively charged ion, can be pure ionic liquid, also can be the mixture of ionic liquid and its zwitterion raw material.
When solvent used in the present invention is used for extracting rectifying separation mixture of carboxylic acids, the mixture of carboxylic acids diagram of system is revealed tangible salt effect, can significantly improve the relative volatility between each component, improve separation efficiency, reduce energy consumption, reduce production costs.
Embodiment
The solvent that extracting rectifying provided by the invention separates mixture of carboxylic acids is that positively charged ion, carboxylate radical are that anion ion liquid is main composition with the organic amine.This ionic liquid and traditional organic extraction solvent phase ratio, have the following advantages: (1) does not almost have vapour pressure, and is non-volatile, colourless, and nothing is smelt; (2) has bigger equilibrium temperature scope and better chemical stability; (3) the mixture of carboxylic acids diagram of system is revealed tangible salt effect, can improve the relative volatility between component.Thereby the used solvent of the present invention both had extractive distillation and separated the high advantage of mixture of carboxylic acids efficient, had again to reclaim conveniently, pollution-free, and the advantage of plasma liquid can overcome conventional extraction solvent and be difficult for the shortcoming of separating with the purpose product.
The positively charged ion of ionic liquid of the present invention is organic amine, can be C
1~ C
20Monoamine, diamine and tertiary amine.
The negatively charged ion of ionic liquid of the present invention is carboxylate radical, can be C
1~ C
20The monocarboxylic acid root.
When mixture of carboxylic acids preferable formic acid-water of the present invention, formic acid-butyl formate, acetic acid-water, acetic acid-propyl acetate, acetic acid-butylacetate, acetic acid-isobutyl acetate, acetic acid-sec-butyl acetate, acetic acid-butanols, propionic acid-butyl propionate, butyric acid-butyl butyrate, extracting rectifying separate used solvent and mixture of carboxylic acids mass ratio be 1:0.01 ~ 99.
Further specify the present invention below by example, but the present invention is not limited to this.
Use the improved Rose vapor-liquid equilibrium still of the two circulations of vapour-liquid to measure vapor-liquid equilibrium data in the example: in boiling-house, to add confected materials liquid, begin heating; Feed water coolant in the prolong above it, solution comes to life behind the certain hour.When temperature reach stable after, reequilibrate 0.5-1 hour, get vapour then simultaneously, liquid two-phase sample is analyzed, and calculates the relative volatility (R) of each component.Its calculation formula is as follows:
R=(
y 1/
y 2)/(
x 1/
x 2)
In the formula,
y 1With
y 2Be respectively the massfraction of two components in the gas phase,
x 1With
x 2Be respectively the massfraction of two components in the liquid phase.
Example 1
(1) preparation triethyl ammonium acetate
The 0.5mol triethylamine added be equipped with in the four neck flasks of agitator, prolong, thermometer, constant pressure funnel, be heated to 70 ℃, drip the glacial acetic acid of 0.5mol, mechanical stirring constant temperature back flow reaction in the flask by constant pressure funnel.To react the liquid underpressure distillation of gained after reaction finishes, and add anhydrous diethyl ether then and carry out extracting and washing, and carry out underpressure distillation again and remove remaining ether, vacuum-drying is spent the night under 60 ℃ of conditions, gets the triethyl ammonium acetate.
(2) extraction ability of investigation ionic liquid
In being the mixed solution of water of 50% formic acid and 50%, massfraction adds ionic liquid triethyl ammonium acetate as solvent, the mass ratio of solvent and mixture is 1:4, measure vapor-liquid equilibrium data, calculate its relative volatility, never 1.03 during solubilizing agent is increased to 2.65.
Example 2
(1) preparation tributyl ammonium formate
The 0.5mol Tributylamine added be equipped with in the four neck flasks of agitator, prolong, thermometer, constant pressure funnel, be heated to 30 ℃, drip the formic acid of 0.5mol, mechanical stirring constant temperature back flow reaction in the flask by constant pressure funnel.To react the liquid underpressure distillation of gained after reaction finishes, and add Skellysolve A then and carry out extracting and washing, and carry out underpressure distillation again and remove remaining Skellysolve A, vacuum-drying is spent the night under 60 ℃ of conditions, gets the tributyl ammonium formate.
(2) extraction ability of investigation ionic liquid
Method according to example 1 (2) step joins the mixing species that massfraction is 20% propionic acid and 80% butyl propionate with the tributyl ammonium formate, measures vapor-liquid equilibrium data, calculates its relative volatility, and never 1.08 during solubilizing agent is increased to 1.79.
Example 3
Method according to example 1 (2) step joins the mixing species that massfraction is 30% butyric acid and 70% butyl butyrate with the tributyl ammonium formate, measures vapor-liquid equilibrium data, calculates its relative volatility, and never 1.06 during solubilizing agent is increased to 1.82.
Example 4
(1) preparation tributyl ammonium acetate
The 0.5mol Tributylamine added be equipped with in the four neck flasks of agitator, prolong, thermometer, constant pressure funnel, be heated to 70 ℃, drip the glacial acetic acid of 0.5mol, mechanical stirring constant temperature back flow reaction in the flask by constant pressure funnel.To react the liquid underpressure distillation of gained after reaction finishes, and add Skellysolve A then and carry out extracting and washing, and carry out underpressure distillation again and remove remaining Skellysolve A, vacuum-drying is spent the night under 60 ℃ of conditions, gets the tributyl ammonium acetate.
(2) extraction ability of investigation ionic liquid
Method according to example 1 (2) step joins the tributyl ammonium acetate in the mixed solution that massfraction is 60% acetic acid and 40% propyl acetate, measures vapor-liquid equilibrium data, calculates its relative volatility, and never 1.56 during solubilizing agent is increased to 2.69.
Example 5
Method according to example 1 (2) step joins the tributyl ammonium acetate in the mixed solution of acetic acid and butylacetate, measures vapor-liquid equilibrium data, calculates its relative volatility, and never 1.27 during solubilizing agent is increased to 1.44.
Example 6
Method according to example 1 (2) step joins the tributyl ammonium acetate in the mixed solution that massfraction is 20% acetic acid and 80% isobutyl acetate, measures vapor-liquid equilibrium data, calculates its relative volatility, and never 1.01 during solubilizing agent is increased to 1.83.
Example 7
Method according to example 1 (2) step joins the tributyl ammonium acetate in the mixed solution that massfraction is 80% acetic acid and 20% sec-butyl acetate, measures vapor-liquid equilibrium data, calculates its relative volatility, and never 1.15 during solubilizing agent is increased to 2.08.
Example 8
(1) preparation tributyl ammonium propionic salt
The 0.5mol Tributylamine added be equipped with in the four neck flasks of agitator, prolong, thermometer, constant pressure funnel, be heated to 70 ℃, drip the propionic acid of 0.5mol, mechanical stirring constant temperature back flow reaction in the flask by constant pressure funnel.To react the liquid underpressure distillation of gained after reaction finishes, and add Skellysolve A then and carry out extracting and washing, and carry out underpressure distillation again and remove remaining Skellysolve A, vacuum-drying is spent the night under 60 ℃ of conditions, gets the tributyl ammonium propionic salt.
(2) extraction ability of investigation ionic liquid
Method according to example 1 (2) step joins the tributyl ammonium propionic salt in the mixed solution of acetic acid and butanols, measures vapor-liquid equilibrium data, calculates its relative volatility, and never 1.05 during solubilizing agent is increased to 1.75.
Example 9
(1) preparation tributyl ammonium butyrates
The 0.5mol Tributylamine added be equipped with in the four neck flasks of agitator, prolong, thermometer, constant pressure funnel, be heated to 70 ℃, drip the butyric acid of 0.5mol, mechanical stirring constant temperature back flow reaction in the flask by constant pressure funnel.To react the liquid underpressure distillation of gained after reaction finishes, and add Skellysolve A then and carry out extracting and washing, and carry out underpressure distillation again and remove remaining Skellysolve A, vacuum-drying is spent the night under 60 ℃ of conditions, gets the tributyl ammonium butyrates.
(2) extraction ability of investigation ionic liquid
Method according to example 1 (2) step joins the tributyl ammonium butyrates in the mixed solution of formic acid and butyl formate, measures vapor-liquid equilibrium data, calculates its relative volatility, and never 1.33 during solubilizing agent is increased to 1.85.
Example 10
Method according to example 1 (2) step joins the tributyl ammonium butyrates in the mixed solution that massfraction is 70% propyl acetate and 30% acetic acid, measures vapor-liquid equilibrium data, calculates its relative volatility, and never 1.56 during solubilizing agent is increased to 2.49.
Example 11
(1) preparation trioctylammonium acetate
The 0.5mol trioctylamine added be equipped with in the four neck flasks of agitator, prolong, thermometer, constant pressure funnel, be heated to 70 ℃, drip the glacial acetic acid of 0.5mol, mechanical stirring constant temperature back flow reaction in the flask by constant pressure funnel.To react the liquid underpressure distillation of gained after reaction finishes, and add Skellysolve A then and carry out extracting and washing, and carry out underpressure distillation again and remove remaining Skellysolve A, vacuum-drying is spent the night under 60 ℃ of conditions, gets the trioctylammonium acetate.
(2) extraction ability of investigation ionic liquid
Method according to example 1 (2) step joins the trioctylammonium acetate in the mixed solution of acetic acid and sec-butyl acetate, measures vapor-liquid equilibrium data, calculates its relative volatility, and never 1.15 during solubilizing agent is increased to 1.88.
Example 8
(1) preparation butyl ammonium acetate
The 0.5mol butylamine added be equipped with in the four neck flasks of agitator, prolong, thermometer, constant pressure funnel, be heated to 30 ℃, drip the glacial acetic acid of 0.5mol, mechanical stirring constant temperature back flow reaction in the flask by constant pressure funnel.To react the liquid underpressure distillation of gained after reaction finishes, and add anhydrous diethyl ether then and carry out extracting and washing, and carry out underpressure distillation again and remove remaining ether, vacuum-drying is spent the night under 60 ℃ of conditions, gets butyl ammonium acetate.
(2) extraction ability of investigation ionic liquid
Method according to example 1 (2) step joins butyl ammonium acetate in the mixed solution of acetic acid and water, measures vapor-liquid equilibrium data, calculates its relative volatility, and never 1.63 during solubilizing agent is increased to 3.77.
The solvent that is used for the extracting rectifying mixture of carboxylic acids that the present invention uses has increased the relative volatility between component to a great extent, can improve separation efficiency, reduce energy consumption, and ionic liquid is non-volatile, it is convenient, pollution-free to reclaim, alternative extraction solvent commonly used overcomes the shortcoming in its use.
Claims (14)
1. an extracting rectifying separates the solvent of mixture of carboxylic acids, and described solvent contains carboxylic acid ammonium's ionic liquid, can be pure ionic liquid, also can be the mixture that ionic liquid and its zwitterion prepare raw material.
2. solvent as claimed in claim 1, the positively charged ion that it is characterized in that described ionic liquid is C
1~ C
20Monobasic, binary and ternary organic amine.
3. solvent as claimed in claim 1, the negatively charged ion that it is characterized in that described ionic liquid is C
1~ C
20The monocarboxylic acid root.
4. solvent as claimed in claim 1 is characterized in that ionic liquid and preparation raw mix intermediate ion liquid are 1:0.01 ~ 99 with the mass ratio for preparing raw material.
5. solvent as claimed in claim 1 is characterized in that described mixture of carboxylic acids is carboxylic acid-water and carboxylic acid-carboxylicesters, carboxylic acid-alcohol, carboxylic acid-ketone, carboxylic acid-aldehyde, carboxylic acid-ether, carboxylic acid-amine.
6. as the described solvent of claim 1-5, it is characterized in that the carboxylic acid in the described mixture of carboxylic acids is C
1~ C
20Monocarboxylic acid.
7. as the described solvent of claim 1-6, it is characterized in that the carboxylicesters in the described mixture of carboxylic acids is monocarboxylic ester, the preferable formic acid methyl esters, ethyl formate, propyl formate, isopropyl formate, butyl formate, tetryl formate, sec.-butyl formate, pentyl formate, isoamyl formate, hexyl formate, methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butylacetate, isobutyl acetate, sec-butyl acetate, tert.-butyl acetate, pentyl acetate, Isoamyl Acetate FCC, sec-amyl acetate, tert.-amyl acetate, hexyl acetate, methyl amyl acetate, methyl propionate, ethyl propionate, propyl propionate, isopropyl propionate, butyl propionate, isobutyl propionate, sec-butyl propionate, amyl propionate, isoamyl propionate, the secondary pentyl ester of propionic acid, methyl-butyrate, methyl isobutyrate, butyric acid acetic acid, ethyl isobutyrate, propyl butyrate, isobutyl butyrate, propyl isobutyrate, isobutyl isobutyrate, butyl butyrate, isobutyl butyrate, isobutyl isobutyrate, pentyl butyrate, isoamyl butyrate, tert.-amyl butyrate, isoamyl isobutyrate
As the described solvent of claim 1-6, it is characterized in that the alcohol in the described mixture of carboxylic acids is monohydroxy-alcohol, particular methanol, ethanol, propyl alcohol, Virahol, butanols, isopropylcarbinol, sec-butyl alcohol, the trimethyl carbinol, 1-amylalcohol, 2-amylalcohol, 3-amylalcohol, primary isoamyl alcohol, sec.-amyl alcohol, tertiary amyl alcohol, 1-hexanol, 2-hexanol, 3-hexanol, isohexyl alcohol.
8. as the described solvent of claim 1-6.
9. it is characterized in that the ketone in the described mixture of carboxylic acids is monoketone, preferred 2-acetone, 2-butanone, 2 pentanone, propione, methyl-n-butyl ketone, 3-hexanone, 2-heptanone, dipropyl ketone.
10. as the described solvent of claim 1-6, it is characterized in that the aldehyde in the described mixture of carboxylic acids is monoaldehyde, preferred butyraldehyde, isobutyric aldehyde, valeral, isovaleric aldehyde, hexanal, enanthaldehyde, octanal.
11. as the described solvent of claim 1-10, the carbon atom number that it is characterized in that the carboxylic acid in the described mixture of carboxylic acids and the carbon atom number of ionic liquid anionic carboxylic acid root can be identical also can be different.
12. as the described solvent of claim 1-11, it is characterized in that solvent used when extracting rectifying separates mixture of carboxylic acids and the mass ratio of mixture of carboxylic acids are: 1:0.01 ~ 99.
13. as the described solvent of claim 1-12, it is characterized in that the massfraction of carboxylic acid in the mixture of carboxylic acids that extracting rectifying separates is full concentration range.
14. as the described solvent of claim 1-13, it is characterized in that the pressure that carries out extracting rectifying can be decompression, normal pressure and pressurization, absolute pressure is 0-10MPa.
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Cited By (7)
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| CN104370694A (en) * | 2014-11-07 | 2015-02-25 | 济南大学 | Separation method of isobutanol-ethyl isobutyrate azeotrope by batch extraction rectification |
| CN104370693A (en) * | 2014-11-07 | 2015-02-25 | 济南大学 | Separation method for batch extractive distillation of methanol-propyl formate azeotrope |
| CN105037154A (en) * | 2015-07-17 | 2015-11-11 | 济南大学 | Isopropanol-methyl isobutyrate azeotrope distillation separation method by using mixed solvent as the extraction solvent |
| CN105254489A (en) * | 2015-10-21 | 2016-01-20 | 南京工业大学 | Method for extracting and separating succinic acid |
| CN107235827A (en) * | 2017-06-13 | 2017-10-10 | 济南大学 | A kind of method of separating formic pentyl ester and amylalcohol |
| CN107473967A (en) * | 2017-07-05 | 2017-12-15 | 北京化工大学 | A kind of method that ion liquid abstraction rectifying removes acid and water simultaneously |
| CN108911962A (en) * | 2018-06-15 | 2018-11-30 | 成都本则生科技有限公司 | A method of the high efficiency extraction Pantothenic acid from enzymolysis liquid |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104370694A (en) * | 2014-11-07 | 2015-02-25 | 济南大学 | Separation method of isobutanol-ethyl isobutyrate azeotrope by batch extraction rectification |
| CN104370693A (en) * | 2014-11-07 | 2015-02-25 | 济南大学 | Separation method for batch extractive distillation of methanol-propyl formate azeotrope |
| CN105037154A (en) * | 2015-07-17 | 2015-11-11 | 济南大学 | Isopropanol-methyl isobutyrate azeotrope distillation separation method by using mixed solvent as the extraction solvent |
| CN105254489A (en) * | 2015-10-21 | 2016-01-20 | 南京工业大学 | Method for extracting and separating succinic acid |
| CN105254489B (en) * | 2015-10-21 | 2017-04-12 | 南京工业大学 | Method for extracting and separating succinic acid |
| CN107235827A (en) * | 2017-06-13 | 2017-10-10 | 济南大学 | A kind of method of separating formic pentyl ester and amylalcohol |
| CN107473967A (en) * | 2017-07-05 | 2017-12-15 | 北京化工大学 | A kind of method that ion liquid abstraction rectifying removes acid and water simultaneously |
| CN108911962A (en) * | 2018-06-15 | 2018-11-30 | 成都本则生科技有限公司 | A method of the high efficiency extraction Pantothenic acid from enzymolysis liquid |
| CN108911962B (en) * | 2018-06-15 | 2021-04-23 | 成都本则生科技有限公司 | Method for efficiently extracting D-pantoic acid from enzymatic hydrolysate |
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