CN109369397B - Ag+Method for separating methyl linolenate by coupling extraction of-short-chain polyol - Google Patents
Ag+Method for separating methyl linolenate by coupling extraction of-short-chain polyol Download PDFInfo
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- CN109369397B CN109369397B CN201811457206.1A CN201811457206A CN109369397B CN 109369397 B CN109369397 B CN 109369397B CN 201811457206 A CN201811457206 A CN 201811457206A CN 109369397 B CN109369397 B CN 109369397B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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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
Abstract
The invention provides Ag+A process for extracting and separating methyl linolenate by coupling short-chain polyol includes methyl esterifying the vegetable oil containing linolenic acid, extracting, washing, back extracting, and vacuum removing solvent to obtain high-purity methyl linolenate product. The innovation of the invention is that the extractant used in the extraction process is Ag+Short-chain polyol mixed solution, which is different from the extracting agent used in the prior silver ion complexing extraction. The advantages are that: the method is simple to operate and can be carried out at normal temperature and normal pressure; the short-chain polyol has low cost; the silver ion complexation method has high extraction selectivity on methyl linolenate, the back-extraction capability of the back-extraction agent is strong, the methyl linolenate product with the purity of 97.03% can be obtained through 1-stage extraction, 2-stage washing and 3-stage back-extraction, and the yield of the methyl linolenate is 75.18%.
Description
Technical Field
The invention relates to the technical field of oil separation and purification, in particular to an extraction method for extracting and separating methyl linolenate from vegetable oil, and specifically relates to Ag+A method for separating methyl linolenate by coupling extraction of short-chain polyol.
Background
Linolenic acid is an omega-3 series of polyunsaturated fatty acids, has the functions of maintaining lipoprotein balance, regulating cholesterol metabolism and reducing blood pressure and blood fat, and is a fatty acid necessary for human bodies. However, linolenic acid cannot be synthesized by the human body and must be taken from the outside. Linolenic acid is often present in the form of glyceride together with oleic acid, linoleic acid, palmitic acid, etc. in linseed oil, perilla seed oil, Chinese tallow kernel oil, etc. Since the properties between unsaturated fatty acids are similar, differing only in carbon chain length and number of double bonds, there is a great difficulty in separation. The existing methods for separating polyunsaturated fatty acid ester include urea inclusion method, molecular distillation method, freezing crystallization method and silver ion complexation method. The silver ion complexation method relies on Ag+The complex reaction with the carbon-carbon double bond of unsaturated fatty acid methyl ester occurs, the selectivity is high, and the purity of the obtained target product is high. In operation, silver salt is dissolved in water or ionic liquid, and silver nitrate aqueous solution orThe ionic liquid solution is used as an extracting agent to extract and separate the methyl linolenate. When the linolenic acid (ester) is extracted and separated by using a silver nitrate aqueous solution, the linolenic acid (ester) with low polarity is difficult to dissolve in the silver nitrate aqueous solution with high polarity, the extraction rate is extremely low, and methanol must be added into the silver nitrate aqueous solution to adjust the polarity of the linolenic acid (ester) so as to increase the solubility of the methyl linolenate in an extraction phase. The addition of methanol has four adverse effects on the separation: 1) the solubility of silver nitrate in an extraction phase is reduced; 2) the solubility of linolenic acid (ester) in the extract phase is increased, and the solubility of other fatty acid (ester) in the extract phase is also increased, so that the separation selectivity and the purity of the linolenic acid (ester) in the product are reduced; 3) the intersolubility of the extract phase and the raw material phase (oil phase) is increased, so that the residual quantity of silver nitrate in the oil phase is increased, and the loss of the silver nitrate is caused; 4) the densities of the extraction phase and the raw material phase are reduced, and the time for the two phases to separate is increased. When the silver nitrate ionic liquid is used for extraction, the ionic liquid has high price, high viscosity and high operation cost.
Aiming at the problems in the implementation process of the existing silver ion complexing method, the invention provides a method for coupling and extracting short-chain polyol and silver salt, which uses the short-chain polyol with low price to replace methanol water solution or ionic liquid with high price to dissolve the silver salt so as to solve the problems.
Disclosure of Invention
Aiming at the defects of the prior technical scheme, the invention aims to provide Ag+Method for separating methyl linolenate by coupling extraction of-short-chain polyol, which adopts Ag+The short-chain polyol solution is used as an extracting agent, and can efficiently and easily extract and separate the methyl linolenate from the mixed fatty acid methyl ester.
The invention realizes the purpose through the following technical scheme:
ag+-a method for separating methyl linolenate by coupling extraction of short-chain polyol, comprising the following steps:
1) methyl esterification of vegetable oil containing linolenic acid to prepare mixed fatty acid methyl ester
Linolenic acid-containing vegetable oils are converted to mixed fatty acid methyl esters by methyl esterification. Methyl esterification of vegetable oils containing linolenic acid is carried out by a known method: weighing 20g of methanol and 1g of KOH, mixing and dissolving, adding into 100g of vegetable oil containing linolenic acid, stirring and refluxing for reaction for 1 hour at the temperature of 60 ℃, standing and layering, taking an upper oil layer, washing the upper oil layer to be neutral by water, and removing water in vacuum to obtain the mixed fatty acid methyl ester.
2) Coupling extraction separation of linolenic acid methyl ester by short-chain polyol and silver salt
2.1) adding silver salt into short-chain polyol for dissolving, and stirring and mixing uniformly under the condition of keeping out of the sun to form Ag+-short-chain polyol solution of Ag+-short chain polyol solution as extractant;
2.2) diluting the mixed fatty acid methyl ester obtained in the step 1) by using a diluent to obtain a mixed fatty acid methyl ester solution;
2.3) Ag obtained in the step 2.1)+-mixing the short-chain polyol solution with the mixed fatty acid methyl ester solution obtained in step 2.2), and extracting by stirring under the condition of keeping out of the sun;
2.4) standing for layering after stirring is finished, taking a lower-layer extract phase, and washing for 1-3 times by using a detergent with the same volume;
2.5) back-extracting the washed extract phase for 1-3 times by using a back-extracting agent with the same volume;
2.6) standing and layering after the back extraction is finished, taking an upper layer of back extraction phase, combining, and then distilling under reduced pressure to remove the solvent to obtain a methyl linolenate product; taking the lower layer, distilling under reduced pressure to remove the solvent, and taking the solvent as an extracting agent to be circularly used in the step 2.3) to enter the next extraction and separation process of the methyl linolenate;
2.7) taking the washing phase obtained in the step 2.4), and removing the solvent by reduced pressure distillation to obtain a byproduct rich in methyl oleate and methyl linoleate.
The Ag+-a method for separating methyl linolenate by coupling and extracting short-chain polyol, wherein the short-chain polyol in the step 2.1) is one of propylene glycol, butanediol, pentanediol and glycerol, preferably butanediol, and most preferably 1, 4-butanediol.
The Ag+Separation of linolenic acid methyl ester by coupling extraction of short-chain polyolThe silver salt in step 2.1) is silver nitrate or silver tetrafluoroborate, preferably silver tetrafluoroborate.
The Ag+Method for separating methyl linolenate by coupling extraction of short-chain polyol and Ag+The silver salt concentration of the short-chain polyol solution is 0.1-0.6g/mL, preferably 0.5 g/mL.
The Ag+-short-chain polyol coupling extraction separation of methyl linolenate, the diluent in step 2.2) being a low polar/non-polar organic solvent, preferably petroleum ether.
The Ag+The method for separating the methyl linolenate by coupling extraction of the short-chain polyol, wherein the detergent in the step 2.4) is a low-polarity/non-polar organic solvent without double bonds, and is preferably one of petroleum ether, n-hexane and n-heptane.
The Ag+The method for separating the methyl linolenate by coupling extraction of the short-chain polyol comprises the step 2.5) of using the stripping agent which is a low-polarity/non-polar organic solvent containing double bonds/triple bonds or a mixed solvent of the low-polarity/non-polar organic solvent containing double bonds/triple bonds and a non-polar organic solvent I, wherein the non-polar organic solvent I is petroleum ether or n-heptane, and the stripping agent is preferably 1-hexene.
The Ag+The method for extracting and separating the methyl linolenate by coupling short-chain polyol comprises the step 1) of extracting and separating the methyl linolenate by using the vegetable oil containing the linolenic acid, namely linseed oil or Chinese tallow kernel oil.
The Ag+-short-chain polyol coupling extraction method for separating methyl linolenate, and Ag in step 2.3)+The ratio of the short-chain polyol solution to the mixed fatty acid methyl ester solution is preferably 1: 1; the extraction temperature is 20-50 ℃, preferably 20-25 ℃; the extraction stirring time is 10-180min, preferably 30 min.
The Ag+The method for separating the linolenic acid methyl ester by coupling extraction of the short-chain polyol has the back extraction temperature of 20-50 ℃ in the step 2.5), and preferably 30-35 ℃; the back-extraction stirring time is 10-180min, preferably 30 min.
The Ag+The method for separating the methyl linolenate by coupling extraction of the short-chain polyol, wherein the stirring speed in the step 2.1) is 300-500 rpm.
The Ag+The method for separating the methyl linolenate by coupling extraction of the short-chain polyol, wherein the extracting agent is recycled for 1-5 times.
By adopting the technical scheme, compared with the existing silver ion complex extraction method, the method has the following beneficial effects:
compared with the method for dissolving silver salt by using methanol aqueous solution as a solvent, the method selects the low-carbon-chain polyol as the solvent to dissolve the silver salt, so that the solubility of the silver salt is increased, and the hydration of silver ions is avoided, thereby improving the extraction capacity and selectivity of methyl linolenate. The low-carbon-chain polyol is used for replacing a methanol water solution, so that the residue of silver salt in a product can be reduced, and the loss of the silver salt is reduced;
compared with the method of dissolving silver salt by using ionic liquid as a solvent, the method selects the low-carbon-chain polyol as the solvent to dissolve the silver salt, and reduces the operation cost because the price of the low-carbon-chain polyol is far lower than that of the ionic liquid;
the low-carbon chain polyol is used as a solvent to dissolve the silver salt, has certain selective dissolving capacity on the methyl linolenate, and is beneficial to the extraction and separation of the methyl linolenate;
fourthly, the extract liquor is washed and back extracted successively. The methyl palmitate, the methyl stearate, the methyl oleate and most of the methyl linoleate in the extract can be removed by washing with the detergent disclosed by the invention, so that the purity of the methyl linoleate in the product is improved. By using the back extraction agent of the invention for back extraction, almost all the methyl linolenate in the extraction phase can be back extracted into the back extraction agent phase due to the action of the back extraction agent and the silver salt, thereby improving the yield of the methyl linolenate;
the extractant in the invention can be circularly used for the extraction and separation of the methyl linolenate through simple desolventizing treatment;
the method has the advantages of normal temperature and pressure, simple operation, low cost of the low-carbon chain polyol, low consumption of the carrier silver salt, low energy consumption in the process, high separation selectivity and easy realization.
Detailed Description
The technical solution of the present invention is further described below with reference to specific examples:
example 1 (AgBF)4Single-stage extraction of butanediol solution, 400mg/mL of methyl ester petroleum ether solution as the starting phase, two-stage washing with n-heptane, three-stage back extraction of 1-hexene)
1) Preparation of Chinese tallow kernel oil methyl ester (mixed fatty acid methyl ester)
The Chinese tallow kernel oil methyl esterification adopts a known method: weighing 20g of methanol and 1g of KOH, mixing and dissolving, adding into 100g of Chinese tallow kernel oil, stirring and refluxing at 60 ℃ for 1 hour, standing for layering, taking an upper oil layer, washing with water to neutrality, and removing water in vacuum to obtain Chinese tallow kernel oil methyl ester (mixed fatty acid methyl ester);
2）AgBF4coupling extraction of linolenic acid methyl ester with butanediol
50mL of 1, 4-butanediol was added with 25g of AgBF4And intensively stirring under the condition of keeping out of the sun to obtain transparent and uniform AgBF4Butanediol solution, stirring speed 300 rpm.
② adding 20g of mixed fatty acid methyl ester into 50mL of petroleum ether to obtain 400mg/mL of fatty acid methyl ester petroleum ether solution.
Thirdly, AgBF in step I4Adding 50mL of fatty acid methyl ester petroleum ether solution obtained in the step II into the butanediol solution, stirring for 30min at normal temperature in a dark place, and performing extraction separation.
Fourthly, standing for 30min in dark after the extraction is finished. Measuring after 30min to obtain 33.84mL of upper extraction raffinate phase and 55.12mL of lower extraction extract phase; analyzing the contents of the methyl linolenate in the raw material before extraction and the extracted upper raffinate phase by using gas chromatography; the content of the methyl linoleate in the raw material is 37.45 percent, and the content of the methyl linoleate in the lower extraction phase is 61.60 percent; the extraction rate of the methyl linolenate is 89.84%.
3) Washing the extract phase to increase the content of methyl linoleate in the extract phase
Taking the lower extraction phase (oil-alcohol phase) obtained in the step 2), adding 55.12mL of n-heptane, stirring at normal temperature in the dark for 30min, and washing and separating; after stirring, standing in dark for 30 min. In this example the oil-alcohol phase was washed 2 times with n-heptane.
And 2, washing the lower oil-alcohol phase for 2 times, combining the washing agent n-heptane in the step 3), and removing the n-heptane by reduced pressure distillation to obtain an oily substance, namely a byproduct rich in methyl oleate and methyl linoleate. The removal rates of methyl oleate and methyl linoleate in the oil-alcohol phase are 47.10% and 65.59% respectively, and the loss rate of methyl linolenate is 15.08%; the content of methyl linoleate in the washed oil-alcohol phase was 4.55%, the content of methyl linoleate was 14.32%, and the purity of methyl linolenate was 77.42%.
4) Back extraction of linolenic acid methyl ester
Adding 55.28mL of 1-hexene (the volume of which is consistent with that of the lower layer oil-alcohol phase after washing) into the extraction phase in the step I in the step 3), stirring for 30min at normal temperature in a dark place, and performing back extraction separation; after stirring, standing in dark for 30 min. In this example, the lower oil-alcohol phase was back-extracted 3 times with 1-hexene, and the volume of 1-hexene back-extractant added for each time was identical to the volume of the oil-alcohol phase after the previous back-extraction.
And 2, after 3 times of back extraction of the lower oil-alcohol phase, combining the 1-hexene back extraction phases obtained in the step 4), and removing 1-hexene through reduced pressure evaporation to obtain a methyl linolenate product, wherein the obtained product has the mass of 4.0504g and is analyzed by gas chromatography to form the linolenic acid methyl ester product, and the content of methyl linolenate in the product is 97.03%. The yield of methyl linolenate was 75.18% by calculation of the formula (1).
Wherein M isP、MFRespectively representing the quality of the product and the raw material phase; xP、XFRepresenting the content of methyl linolenate in the product and feed phases, respectively.
Example 2 (AgBF)4Single-stage extraction with propylene glycol solution, 50mg/mL methyl ester petroleum ether solution as the starting phase)
The operation method is the same as that of example 1However, unlike example 1, 20g of AgBF was added to 50mL of 1, 3-propanediol4And intensively stirring under the condition of keeping out of the sun to obtain transparent and uniform AgBF4Propylene glycol solution as extractant, 50mL of fatty acid methyl ester petroleum ether solution with concentration of 50mg/mL as raw material phase, and stirring speed of 400 rpm.
After extraction, standing in dark for 30 min. Measuring after 30min to obtain the volume of the upper extraction raffinate phase of 39.68mL and the volume of the lower extraction phase of 52.29 mL; the content of linolenic acid methyl ester in the lower extraction phase is 68.46%; the extraction rate of the methyl linolenate is 82.64 percent.
Example 3 (AgBF)4Single-stage extraction with pentanediol solution, 50mg/mL methyl ester petroleum ether solution as the starting phase)
The procedure is as in example 1, but differs from example 1 in that 20g of AgBF are added to 50mL of 1, 5-pentanediol4And intensively stirring under the condition of keeping out of the sun to obtain transparent and uniform AgBF4Pentanediol solution is used as an extracting agent, 50mL of fatty acid methyl ester petroleum ether solution with the concentration of 50mg/mL is used as a raw material phase, and the stirring speed is 500 rpm.
After extraction, standing in dark for 30 min. Measuring after 30min to obtain 38.82mL of upper extraction raffinate phase and 52.88mL of lower extraction extract phase; the content of linolenic acid methyl ester in the lower extraction phase is 61.00%; the extraction rate of the methyl linolenate is 94.27%.
Example 4 (AgBF)4Single-stage extraction of butanediol solution, 50mg/mL methyl ester petroleum ether solution as a starting phase, and comparison (starting phase: extract phase) = 5: 1)
the procedure is as in example 1, but differs from example 1 in that 10g of AgBF are added to 25mL of 1, 4-butanediol4And intensively stirring under the condition of keeping out of the sun to obtain transparent and uniform AgBF4The butanediol solution is used as an extracting agent, 125mL of fatty acid methyl ester petroleum ether solution with the concentration of 50mg/mL is used as a raw material phase, and the stirring speed is 300 rpm.
After extraction, standing in dark for 30 min. Measuring after 30min to obtain 115.91mL of upper extraction raffinate phase and 26.65mL of lower extraction extract phase; the content of linolenic acid methyl ester in the lower extraction phase is 74.77%; the extraction rate of the methyl linolenate is 48.33%.
Example 5 (Single-stage extraction of butanediol solution, 50mg/mL methyl ester Petroleum ether solution as starting phase)
The procedure is as in example 1, but differs from example 1 in that no AgBF was added to 50mL of 1, 4-butanediol450mL of a fatty acid methyl ester petroleum ether solution having a concentration of 50mg/mL was used as a raw material phase, and the stirring speed was 300 rpm.
After extraction, standing in dark for 30 min. Measuring after 30min to obtain 37.65mL of upper extraction raffinate phase and 53.98mL of lower extraction extract phase; the content of linolenic acid methyl ester in the lower extraction phase is 40.13%; the extraction rate of the methyl linolenate is 12.72 percent.
Example 6 (butanediol-AgBF)4Solution single-stage extraction recycling use)
Adding 50mL of fatty acid methyl ester petroleum ether solution with the concentration of 400mg/mL into butanediol-silver tetrafluoroborate extract phase solution subjected to washing and back extraction for 3 times in example 1; stirring at room temperature in dark place for 30min, and performing second extraction separation.
② after extraction, standing for 30min in dark. Analyzing the content of the methyl linolenate in the upper extraction raffinate phase after extraction by using gas chromatography after 30 min; the content of linolenic acid methyl ester in the lower extraction phase is 61.15%; the extraction rate of the methyl linolenate is 84.30 percent.
③ the lower extraction phase in the second step is added with 50mL of fatty acid methyl ester petroleum ether solution with the concentration of 400mg/mL after 2 times of washing and 3 times of back extraction under the same operation conditions of the embodiment 1; stirring at room temperature in dark place for 30min, and performing third extraction separation.
Fourthly, standing for 30min in dark after the extraction is finished. Analyzing the content of the methyl linolenate in the upper extraction raffinate phase after extraction by using gas chromatography after 30 min; the content of linolenic acid methyl ester in the lower extraction phase is 65.69%; the extraction rate of the methyl linolenate is 78.57%.
Claims (13)
1. Ag+-a method for separating methyl linolenate by coupling extraction of short-chain polyol, characterized by comprising the steps of:
1) performing methyl esterification reaction on vegetable oil containing linolenic acid and methanol to obtain mixed fatty acid methyl ester;
2) short-chain polyol and silver salt coupling extraction separation of methyl linolenate:
2.1) adding silver salt into short-chain polyol, dissolving, and stirring and mixing uniformly under the condition of keeping out of the sun to form Ag+-short-chain polyol solution of Ag+-short-chain polyol solution as extractant, wherein the short-chain polyol is any one of propylene glycol, butanediol, pentanediol or glycerol, the silver salt is silver tetrafluoroborate, and the Ag is+-the silver salt concentration of the short-chain polyol solution is 0.1-0.6 g/mL;
2.2) diluting the mixed fatty acid methyl ester obtained in the step 1) by using a diluent to obtain a mixed fatty acid methyl ester solution;
2.3) Ag obtained in the step 2.1)+-mixing the short-chain polyol solution with the mixed fatty acid methyl ester solution obtained in step 2.2), and stirring and extracting under the condition of keeping out of the sun;
2.4) standing for layering after stirring is finished, taking a lower-layer extract phase, and washing for 1-3 times by using a detergent with the same volume;
2.5) back-extracting the washed extract phase for 1-3 times by using a back-extracting agent with the same volume;
2.6) standing and layering after the back extraction is finished, taking an upper layer of back extraction phase, combining, and then distilling under reduced pressure to remove the solvent to obtain a methyl linolenate product; taking the lower layer, distilling under reduced pressure to remove the solvent, and taking the solvent as an extracting agent to be circularly used in the step 2.3) to enter the next extraction and separation process of the methyl linolenate;
2.7) taking the washing phase obtained in the step 2.4), and removing the solvent by reduced pressure distillation to obtain a byproduct rich in methyl oleate and methyl linoleate.
2. Ag according to claim 1+-a method for separating methyl linolenate by coupling extraction of a short-chain polyol, characterized in that in step 2.1) the short-chain polyol is butanediol.
3. A according to claim 1g+-short-chain polyol coupling extraction method for separating methyl linolenate, characterized in that Ag in step 2.1)+-the silver salt concentration of the short-chain polyol solution is 0.5 g/mL.
4. Ag according to claim 1+-a process for the coupled extraction separation of methyl linolenate by short-chain polyols, characterized in that in step 2.2) the diluent is a low polar/non-polar organic solvent; the detergent in step 2.4) is a low-polarity/non-polar organic solvent without double bonds.
5. Ag according to claim 1+The method for separating the methyl linolenate by coupling extraction of the short-chain polyol is characterized in that the back-extracting agent in the step 2.5) is a low-polarity/non-polar organic solvent containing double bonds/triple bonds or a mixed solvent of the low-polarity/non-polar organic solvent containing double bonds/triple bonds and a non-polar organic solvent I, and the non-polar organic solvent I is petroleum ether or n-heptane.
6. Ag according to claim 1+-a method for separating methyl linolenate by coupling extraction of short-chain polyol, characterized in that in step 2.2) the diluent is petroleum ether; in the step 2.4), the detergent is petroleum ether, n-hexane or n-heptane.
7. Ag according to claim 1+-short-chain polyol coupling extraction separation method of methyl linolenate, characterized in that the stripping agent in step 2.5) is 1-hexene.
8. Ag according to claim 1+The method for separating the methyl linolenate by coupling extraction of the short-chain polyol is characterized in that the vegetable oil containing the linolenic acid in the step 1) is linseed oil or Chinese tallow kernel oil.
9. Ag according to claim 1+Separation of linolenic acid A by coupling extraction of short-chain polyolMethod for esterification, characterized in that Ag is mentioned in step 2.3)+The ratio of the short-chain polyol solution to the mixed fatty acid methyl ester solution is 1:1, the extraction temperature is 20-50 ℃, and the extraction stirring time is 10-180 min.
10. Ag according to claim 1+The method for separating the linolenic acid methyl ester by coupling extraction of the short-chain polyol is characterized in that the back extraction temperature in the step 2.5) is 30-35 ℃, and the back extraction stirring time is 30 min.
11. Ag according to claim 1+The method for extracting and separating the linolenic acid methyl ester by coupling short-chain polyol is characterized in that the extraction temperature in the step 2.3) is 20-25 ℃, and the extraction stirring time is 30 min.
12. Ag according to claim 1+The method for separating the methyl linolenate by coupling extraction of the short-chain polyol is characterized in that the stirring speed in the step 2.1) is 300-500 rpm.
13. Ag according to claim 1+-short-chain polyol coupling extraction separation method of methyl linolenate, characterized in that the extractant is recycled for 1-5 times.
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| CN108069858A (en) * | 2017-11-10 | 2018-05-25 | 浙江工业大学 | A kind of method of fatty acid soaps and silver nitrate coupling extract and separate methyl linolenate |
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