CN115466161A - Method for separating and purifying linolenic acid from cornus wilsoniana fruit oil - Google Patents

Method for separating and purifying linolenic acid from cornus wilsoniana fruit oil Download PDF

Info

Publication number
CN115466161A
CN115466161A CN202211319210.8A CN202211319210A CN115466161A CN 115466161 A CN115466161 A CN 115466161A CN 202211319210 A CN202211319210 A CN 202211319210A CN 115466161 A CN115466161 A CN 115466161A
Authority
CN
China
Prior art keywords
linolenic acid
purifying
separating
fruit oil
silica gel
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN202211319210.8A
Other languages
Chinese (zh)
Inventor
李昌珠
刘思思
刘汝宽
肖志红
涂佳
肖静晶
吉悦娜
李力
王昊
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hunan Academy of Forestry
Original Assignee
Hunan Academy of Forestry
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hunan Academy of Forestry filed Critical Hunan Academy of Forestry
Priority to CN202211319210.8A priority Critical patent/CN115466161A/en
Publication of CN115466161A publication Critical patent/CN115466161A/en
Pending legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41Preparation of salts of carboxylic acids
    • C07C51/412Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/02Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42Separation; Purification; Stabilisation; Use of additives
    • C07C51/43Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
    • C07C51/44Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42Separation; Purification; Stabilisation; Use of additives
    • C07C51/47Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42Separation; Purification; Stabilisation; Use of additives
    • C07C51/48Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/54Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

Abstract

The invention discloses a method for separating and purifying linolenic acid from cornus wilsoniana fruit oil, which relates to the technical field of separation and purification, and comprises the following steps of S1: ultrasonic coarse extraction; s2: saponification; s3: extracting and separating to obtain mixed fatty acid; s4: distilling under reduced pressure to obtain linolenic acid; s5: purifying linolenic acid with silica gel chromatographic column; compared with the separation and purification method in the prior art, the method for separating and purifying linolenic acid from cornus wilsoniana fruit oil provided by the application reduces the solvent consumption, consumes less and has high recovery rate; the high requirements on equipment are reduced, and the separation and purification cost is reduced; compared with the separation and purification method in the prior art, the separation and purification method has the advantage of low temperature, and the loss of linolenic acid caused by high temperature is avoided by adopting the separation and purification condition of low temperature change; the linolenic acid obtained by the separation and purification method provided by the application has high purity.

Description

Method for separating and purifying linolenic acid from cornus wilsoniana fruit oil
Technical Field
The invention relates to the technical field of separation and purification, in particular to a method for separating and purifying linolenic acid from cornus wilsoniana fruit oil.
Background
Linolenic acid is known to be one of effective health-care foods for human, can degrade harmful pathological substances of human bodies such as low-density lipoprotein cholesterol, high triglyceride and the like, increases the content of high-density lipoprotein components, effectively prevents and treats hyperlipidemia, fatty liver, myocardial infarction and hypertension, inhibits thrombosis, dissolves thrombus, repairs thrombus scars, ensures blood oxygen required by blood vessels, recovers the elasticity of the blood vessels, and achieves the aim of softening the blood vessels; the current purification method of linolenic acid generally comprises the following steps: urea inclusion method, low-temperature crystallization method, supercritical fluid extraction method and the like, but the existing purification methods all have various defects: the urea inclusion method and the low-temperature crystallization method require a large amount of solvent, and have high consumption and low yield; the supercritical extraction needs to be operated under quite high pressure, the equipment requirement is high, and the processing cost is high; other separation and purification methods have high temperature and high loss of linolenic acid; the cornus wilsoniana is an important woody oil plant in the family of dogwood in dogwood, the oil content of the whole fruit is 30-36%, and because the content of linolenic acid in the cornus wilsoniana fruit oil is not high, reports on the separation and purification of the linolenic acid from the cornus wilsoniana fruit oil are few. Therefore, in order to realize high-value utilization of cornus wilsoniana and increase the added value of cornus wilsoniana fruit oil, it is urgently required to develop a method for separating and purifying linolenic acid from cornus wilsoniana fruit oil so as to meet the requirement of practical use.
Disclosure of Invention
In view of the above, the present invention provides a method for separating and purifying linolenic acid from cornus wilsoniana fruit oil, which avoids the loss of linolenic acid due to high temperature by using the separation and purification conditions of low temperature change; the linolenic acid obtained by the separation and purification method provided by the application has high purity.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method for separating and purifying linolenic acid from cornus wilsoniana fruit oil comprises the following steps:
s1: ultrasonic coarse extraction: putting the cornus wilsoniana fruit oil into ultrasonic waves to perform ultrasonic extraction for 40-50 minutes, wherein the ultrasonic temperature is 30-50 ℃, and the ultrasonic pressure is normal pressure, and performing ultrasonic extraction to obtain a crude extract;
s2: saponification: carrying out saponification reaction on the crude extract obtained in the step S1 to obtain a saponification reaction product; adding alkali and ethanol or methanol into the crude extract obtained in the step S1, wherein the weight ratio of the crude extract to the ethanol or the methanol is 1:10-1:15, the addition amount of alkali is 0.5 to 3 times of the weight of the crude extract, the saponification reaction temperature is 45 to 50 ℃, and the reaction time is 1 to 2 hours; adding hydrochloric acid into the saponification reactant to adjust the pH to 4-5;
s3: extracting and separating to obtain mixed fatty acid: and (3) adding an aqueous phase and an organic phase into the saponification reactant obtained in the step (S2) for extraction, wherein the aqueous phase is saturated saline solution, and the organic phase is ethyl acetate and acetone, and the feed-liquid ratio of the saponification reactant to the organic phase is 1:4-1:2, the volume ratio of the ethyl acetate to the acetone is 7:1-9:1, the extraction temperature is 70-90 ℃, the extraction time is 30-50 min, extracted organic phases are obtained, and the organic phases are combined and concentrated to obtain mixed fatty acid;
s4: and (3) carrying out reduced pressure rectification separation to obtain linolenic acid: performing reduced pressure rectification on the mixed fatty acid obtained in the step S3, wherein the pressure of the reduced pressure rectification is 60-80 Pa, the temperature is 80-90 ℃, and the rectification is repeated twice to obtain linolenic acid;
s5: purifying linolenic acid by using a silica gel chromatographic column: eluting the linolenic acid obtained in the S4 by adopting a silica gel chromatographic column, wherein the stationary phase of the silica gel chromatographic column is silica gel and an acrylate polymer, the mobile phase of the silica gel chromatographic column is ethanol with the mass fraction of 70-90%, and the elution temperature of the silica gel chromatographic column is 30-40 ℃.
As a preferred embodiment: and drying the combined organic phases in the S3 by using anhydrous sodium sulfate, and concentrating to obtain the mixed fatty acid.
As a preferred embodiment: the material-liquid ratio of the saponification reactant to the organic phase in S3 is 1:3, the volume ratio of ethyl acetate to acetone is 8:1, the extraction temperature is 80 ℃, and the extraction time is 40min.
As a preferred embodiment: the concentration of ethanol or methanol in the S2 is 98%.
As a preferred scheme: the addition amount of the alkali in the S2 is 2 times of the weight of the crude extract, and the saponification reaction temperature is 48 ℃.
As a preferred embodiment: and the pressure of the vacuum rectification in the S4 is 70Pa, and the temperature is 85 ℃.
As a preferred embodiment: the mass ratio of the silica gel to the acrylate polymer in the S5 is 10:1.
as a preferred embodiment: the flow rate of the S5 mobile phase was 0.85 ml/min.
As a preferred scheme: and the alkali in the S2 is NaOH solution or KOH solution.
As a preferred embodiment: the mass fraction of the NaOH solution or the KOH solution is 2 to 5 percent.
Compared with the prior art, the method has obvious advantages and beneficial effects, and concretely, according to the technical scheme, compared with the separation and purification method in the prior art, the method for separating and purifying linolenic acid from cornus wilsoniana fruit oil provided by the application has the advantages that the solvent consumption is reduced, the consumption is low, and the recovery rate is high; the high requirements on equipment are reduced, and the separation and purification cost is reduced; compared with the separation and purification method in the prior art, the separation and purification method provided by the application has the advantage of low temperature, and the loss of linolenic acid caused by high temperature is avoided by adopting the separation and purification condition of low temperature change; the linolenic acid obtained by the separation and purification method provided by the application has high purity.
Detailed Description
Example 1:
s1: ultrasonic coarse extraction: putting the cornus wilsoniana fruit oil into ultrasonic waves for ultrasonic extraction for 40 minutes, wherein the ultrasonic temperature is 30 ℃, and the ultrasonic pressure is normal pressure, and the crude extract is obtained by ultrasonic extraction;
s2: saponification: carrying out saponification reaction on the crude extract obtained in the step S1 to obtain a saponification reaction product; adding alkali and 98% ethanol into the crude extract obtained in the step S1, wherein the weight ratio of the crude extract to the ethanol is 1:10, adding 0.5 time of alkali in the weight of the crude extract, wherein the saponification reaction temperature is 45 ℃, and the reaction time is 1h; adding hydrochloric acid into the saponification reactant to adjust the pH to 4; adding alkali to obtain NaOH solution with the mass fraction of 2%;
s3: extracting and separating to obtain mixed fatty acid: and (3) adding an aqueous phase and an organic phase into the saponification reactant obtained in the step (S2) for extraction, wherein the aqueous phase is saturated saline water, and the organic phase is ethyl acetate and acetone, and the feed-liquid ratio of the saponification reactant to the organic phase is 1:4, the volume ratio of the ethyl acetate to the acetone is 7:1, the extraction temperature is 70 ℃, the extraction time is 30min, an extracted organic phase is obtained, and the organic phase is combined and dried and concentrated by using anhydrous sodium sulfate to obtain mixed fatty acid;
s4: and (3) carrying out reduced pressure rectification separation to obtain linolenic acid: performing reduced pressure rectification on the mixed fatty acid obtained in the step S3, wherein the pressure of the reduced pressure rectification is 60Pa, the temperature is 80 ℃, and performing rectification twice to obtain linolenic acid;
s5: purifying linolenic acid by using a silica gel chromatographic column: eluting the linolenic acid obtained in the step S4 by using a silica gel chromatographic column, wherein the stationary phase of the silica gel chromatographic column is silica gel and an acrylate polymer, the mobile phase of the silica gel chromatographic column is ethanol with the mass fraction of 70%, the elution temperature of the silica gel chromatographic column is 30 ℃, and the mass ratio of the silica gel to the acrylate polymer in the step S5 is 10:1, the flow rate of the mobile phase in S5 is 0.85 ml/min; purifying to obtain linolenic acid with the purity of 95.8 percent.
Example 2:
s1: ultrasonic coarse extraction: ultrasonically extracting cornus wilsoniana fruit oil in ultrasonic waves for 45 minutes at 40 ℃ and normal pressure to obtain a crude extract;
s2: saponification: carrying out saponification reaction on the crude extract obtained in the step S1 to obtain a saponification reaction product; adding alkali and 98% ethanol into the crude extract obtained in the step S1, wherein the weight ratio of the crude extract to the ethanol is 1:12, adding 1 time of alkali in the weight of the crude extract, wherein the saponification reaction temperature is 48 ℃, and the reaction time is 1.5h; adding hydrochloric acid into the saponification reaction product to adjust the pH value to 4.5; the alkali is NaOH solution, and the mass fraction of the NaOH solution is 3%;
s3: extracting and separating to obtain mixed fatty acid: and (3) adding an aqueous phase and an organic phase into the saponification reactant obtained in the step (S2) for extraction, wherein the aqueous phase is saturated saline solution, the organic phase is ethyl acetate and acetone, and the feed-liquid ratio of the saponification reactant to the organic phase is 1:3, the volume ratio of the ethyl acetate to the acetone is 8:1, the extraction temperature is 80 ℃, the extraction time is 40min, an extracted organic phase is obtained, and the organic phase is combined and dried and concentrated by using anhydrous sodium sulfate to obtain mixed fatty acid;
s4: and (3) carrying out reduced pressure rectification separation to obtain linolenic acid: performing reduced pressure rectification on the mixed fatty acid obtained in the step S3, wherein the pressure of the reduced pressure rectification is 70PaPa, the temperature is 85 ℃, and performing rectification twice to obtain linolenic acid;
s5: purifying linolenic acid by using a silica gel chromatographic column: eluting the linolenic acid obtained in the S4 by using a silica gel chromatographic column, wherein the stationary phase of the silica gel chromatographic column is silica gel and an acrylate polymer, the mobile phase of the silica gel chromatographic column is ethanol with the mass fraction of 70-90%, the elution temperature of the silica gel chromatographic column is 30-40 ℃, and the mass ratio of the silica gel to the acrylate polymer is 10:1, the flow rate of the mobile phase is 0.85 ml/min; purifying to obtain linolenic acid with the purity of 96.2 percent.
Example 3:
s1: ultrasonic coarse extraction: putting the cornus wilsoniana fruit oil into ultrasonic waves for ultrasonic extraction for 48 minutes, wherein the ultrasonic temperature is 48 ℃, and the ultrasonic pressure is normal pressure, and the crude extract is obtained by ultrasonic extraction;
s2: saponification: carrying out saponification reaction on the crude extract obtained in the step S1 to obtain a saponification reaction product; adding alkali and 98% ethanol into the crude extract obtained in the step S1, wherein the weight ratio of the crude extract to the ethanol is 1:14, adding 2 times of alkali in weight of the crude extract, wherein the saponification reaction temperature is 48 ℃, and the reaction time is 2 hours; adding hydrochloric acid into the saponification reactant to adjust the pH to 5; the added alkali is NaOH solution, and the mass fraction of the NaOH solution is 4%;
s3: extracting and separating to obtain mixed fatty acid: and (3) adding an aqueous phase and an organic phase into the saponification reactant obtained in the step (S2) for extraction, wherein the aqueous phase is saturated saline water, and the organic phase is ethyl acetate and acetone, and the feed-liquid ratio of the saponification reactant to the organic phase is 1:3, the volume ratio of the ethyl acetate to the acetone is 8:1, the extraction temperature is 80 ℃, the extraction time is 40min, an extracted organic phase is obtained, and the organic phase is combined, dried and concentrated by using anhydrous sodium sulfate to obtain mixed fatty acid;
s4: and (3) carrying out reduced pressure rectification separation to obtain linolenic acid: performing reduced pressure rectification on the mixed fatty acid obtained in the step S3, wherein the pressure of the reduced pressure rectification is 70Pa, the temperature is 85 ℃, and the rectification is repeated twice to obtain linolenic acid;
s5: purifying linolenic acid by using a silica gel chromatographic column: eluting the linolenic acid obtained in the S4 by using a silica gel chromatographic column, wherein the stationary phase of the silica gel chromatographic column is silica gel and an acrylate polymer, the mobile phase of the silica gel chromatographic column is ethanol with the mass fraction of 85%, the elution temperature of the silica gel chromatographic column is 35 ℃, and the mass ratio of the silica gel to the acrylate polymer is 10:1, the flow rate of the mobile phase is 0.85 ml/min; purifying to obtain linolenic acid with the purity of 96.8 percent.
Example 4:
s1: ultrasonic coarse extraction: putting the cornus wilsoniana fruit oil into ultrasonic waves for ultrasonic extraction for 50 minutes, wherein the ultrasonic temperature is 50 ℃, and the ultrasonic pressure is normal pressure, and the crude extract is obtained by ultrasonic extraction;
s2: saponification: carrying out saponification reaction on the crude extract obtained in the step S1 to obtain a saponification reaction product; adding alkali and methanol with the concentration of 98% into the crude extract obtained in the step S1, wherein the weight ratio of the crude extract to the methanol is 1:15, adding 3 times of alkali in weight of the crude extract, wherein the saponification reaction temperature is 50 ℃, and the reaction time is 12 hours; adding hydrochloric acid into the saponification reactant to adjust the pH to 5; the alkali is KOH solution, and the mass fraction of the KOH solution is 5 percent;
s3: extracting and separating to obtain mixed fatty acid: and (3) adding an aqueous phase and an organic phase into the saponification reactant obtained in the step (S2) for extraction, wherein the aqueous phase is saturated saline water, and the organic phase is ethyl acetate and acetone, and the feed-liquid ratio of the saponification reactant to the organic phase is 1:2, the volume ratio of ethyl acetate to acetone is 9:1, the extraction temperature is 90 ℃, the extraction time is 50min, an extracted organic phase is obtained, and the organic phase is combined and dried and concentrated by anhydrous sodium sulfate to obtain mixed fatty acid;
s4: and (3) carrying out reduced pressure rectification separation to obtain linolenic acid: performing reduced pressure rectification on the mixed fatty acid obtained in the step S3, wherein the pressure of the reduced pressure rectification is 70Pa, the temperature is 85 ℃, and performing rectification twice to obtain linolenic acid;
s5: purifying linolenic acid by using a silica gel chromatographic column: eluting the linolenic acid obtained in the S4 by using a silica gel chromatographic column, wherein the stationary phase of the silica gel chromatographic column is silica gel and an acrylate polymer, the mobile phase of the silica gel chromatographic column is ethanol with the mass fraction of 90%, the elution temperature of the silica gel chromatographic column is 40 ℃, and the mass ratio of the silica gel to the acrylate polymer is 10:1, flow rate of mobile phase is 0.85 ml/min; purifying to obtain linolenic acid with the purity of 97.2 percent.
Example 5:
s1: ultrasonic coarse extraction: putting the cornus wilsoniana fruit oil into ultrasonic waves for ultrasonic extraction for 50 minutes, wherein the ultrasonic temperature is 50 ℃, and the ultrasonic pressure is normal pressure, and the crude extract is obtained by ultrasonic extraction;
s2: saponification: performing saponification reaction on the crude extract obtained in the step S1 to obtain a saponification reaction product; adding alkali and methanol with the concentration of 98% into the crude extract obtained in the step S1, wherein the weight ratio of the crude extract to the methanol is 1:15, adding 3 times of alkali in weight of the crude extract, wherein the saponification reaction temperature is 48 ℃, and the reaction time is 1h; adding hydrochloric acid into the saponification reactant to adjust the pH to 4; the added alkali is KOH solution, and the mass fraction of the KOH solution is 4 percent;
s3: extracting and separating to obtain mixed fatty acid: and (3) adding an aqueous phase and an organic phase into the saponification reactant obtained in the step (S2) for extraction, wherein the aqueous phase is saturated saline water, and the organic phase is ethyl acetate and acetone, and the feed-liquid ratio of the saponification reactant to the organic phase is 1:3, the volume ratio of the ethyl acetate to the acetone is 8:1, the extraction temperature is 80 ℃, the extraction time is 40min, an extracted organic phase is obtained, and the organic phase is combined and concentrated to obtain mixed fatty acid;
s4: and (3) carrying out reduced pressure rectification separation to obtain linolenic acid: performing reduced pressure rectification on the mixed fatty acid obtained in the step S3, wherein the pressure of the reduced pressure rectification is 70Pa, the temperature is 85 ℃, and performing rectification twice to obtain linolenic acid;
s5: purifying linolenic acid by using a silica gel chromatographic column: eluting the linolenic acid obtained in the S4 by using a silica gel chromatographic column, wherein the stationary phase of the silica gel chromatographic column is silica gel and an acrylate polymer, the mobile phase of the silica gel chromatographic column is ethanol with the mass fraction of 85%, the elution temperature of the silica gel chromatographic column is 35 ℃, and the mass ratio of the silica gel to the acrylate polymer is 10:1, the flow rate of the mobile phase is 0.85 ml/min; purifying to obtain linolenic acid with the purity of 98.1 percent.
Example 6:
s1: ultrasonic coarse extraction: ultrasonically extracting cornus wilsoniana fruit oil in ultrasonic waves for 45 minutes at the ultrasonic temperature of 45 ℃ and under the ultrasonic pressure of normal pressure to obtain a crude extract;
s2: saponification: carrying out saponification reaction on the crude extract obtained in the step S1 to obtain a saponification reaction product; adding alkali and methanol with the concentration of 98% into the crude extract obtained in the step S1, wherein the weight ratio of the crude extract to the methanol is 1:15, adding 2 times of alkali in weight of the crude extract, wherein the saponification reaction temperature is 48 ℃, and the reaction time is 2 hours; adding hydrochloric acid into the saponification reactant to adjust the pH to 5; the added alkali is KOH solution, and the mass fraction of the KOH solution is 5 percent;
s3: extracting and separating to obtain mixed fatty acid: and (3) adding an aqueous phase and an organic phase into the saponification reactant obtained in the step (S2) for extraction, wherein the aqueous phase is saturated saline solution, the organic phase is ethyl acetate and acetone, and the feed-liquid ratio of the saponification reactant to the organic phase is 1:3, the volume ratio of the ethyl acetate to the acetone is 8:1, the extraction temperature is 80 ℃, the extraction time is 40min, an extracted organic phase is obtained, and the organic phase is combined and concentrated to obtain mixed fatty acid;
s4: and (3) carrying out reduced pressure rectification separation to obtain linolenic acid: performing reduced pressure rectification on the mixed fatty acid obtained in the step S3, wherein the pressure of the reduced pressure rectification is 70Pa, the temperature is 85 ℃, and performing rectification twice to obtain linolenic acid;
s5: purifying linolenic acid by using a silica gel chromatographic column: eluting the linolenic acid obtained in the S4 by using a silica gel chromatographic column, wherein the stationary phase of the silica gel chromatographic column is silica gel and an acrylate polymer, the mobile phase of the silica gel chromatographic column is ethanol with the mass fraction of 90%, the elution temperature of the silica gel chromatographic column is 40 ℃, and the mass ratio of the silica gel to the acrylate polymer is 10:1, the flow rate of the mobile phase is 0.85 ml/min; purifying to obtain linolenic acid with the purity of 98.5 percent.
The method has the key design points that compared with the separation and purification method in the prior art, the method for separating and purifying linolenic acid from cornus wilsoniana fruit oil provided by the invention reduces the solvent consumption, consumes less and has high recovery rate; the high requirements on equipment are reduced, and the separation and purification cost is reduced; compared with the separation and purification method in the prior art, the separation and purification method provided by the application has the advantage of low temperature, and the loss of linolenic acid caused by high temperature is avoided by adopting the separation and purification condition of low temperature change; the linolenic acid obtained by the separation and purification method provided by the application has high purity.
The above description is only a preferred embodiment of the present invention, and is not intended to limit the technical scope of the present invention, so that any minor modifications, equivalent changes and modifications made to the above embodiment according to the technical spirit of the present invention are within the technical scope of the present invention.

Claims (10)

1. A method for separating and purifying linolenic acid from cornus wilsoniana fruit oil is characterized in that; the method comprises the following steps:
s1: ultrasonic coarse extraction: putting the cornus wilsoniana fruit oil into ultrasonic waves to perform ultrasonic extraction for 40-50 minutes, wherein the ultrasonic temperature is 30-50 ℃, and the ultrasonic pressure is normal pressure, and performing ultrasonic extraction to obtain a crude extract;
s2: saponification: carrying out saponification reaction on the crude extract obtained in the step S1 to obtain a saponification reaction product; adding alkali and ethanol or methanol into the crude extract obtained in the step S1, wherein the weight ratio of the crude extract to the ethanol or the methanol is 1:10-1:15, the adding amount of alkali is 0.5 to 3 times of the weight of the crude extract, the saponification reaction temperature is 45 to 50 ℃, and the reaction time is 1 to 2 hours; adding hydrochloric acid into the saponification reactant to adjust the pH to 4-5;
s3: extracting and separating to obtain mixed fatty acid: and (3) adding an aqueous phase and an organic phase into the saponification reactant obtained in the step (S2) for extraction, wherein the aqueous phase is saturated saline solution, and the organic phase is ethyl acetate and acetone, and the feed-liquid ratio of the saponification reactant to the organic phase is 1:4-1:2, the volume ratio of the ethyl acetate to the acetone is 7:1-9:1, the extraction temperature is 70-90 ℃, the extraction time is 30-50 min, extracted organic phases are obtained, and the organic phases are combined and concentrated to obtain mixed fatty acid;
s4: and (3) carrying out reduced pressure rectification separation to obtain linolenic acid: performing reduced pressure rectification on the mixed fatty acid obtained in the step S3, wherein the pressure of the reduced pressure rectification is 60-80 Pa, the temperature is 80-90 ℃, and the rectification is repeated twice to obtain linolenic acid;
s5: purifying linolenic acid by using a silica gel chromatographic column: eluting the linolenic acid obtained in the S4 by adopting a silica gel chromatographic column, wherein the stationary phase of the silica gel chromatographic column is silica gel and an acrylate polymer, the mobile phase of the silica gel chromatographic column is ethanol with the mass fraction of 70-90%, and the elution temperature of the silica gel chromatographic column is 30-40 ℃.
2. The method for separating and purifying linolenic acid from cornus wilsoniana fruit oil according to claim 1, wherein; and drying the combined organic phases in the S3 by using anhydrous sodium sulfate, and concentrating to obtain the mixed fatty acid.
3. The method for separating and purifying linolenic acid from cornus wilsoniana fruit oil according to claim 1, wherein; the material-liquid ratio of the saponification reactant to the organic phase in S3 is 1:3, the volume ratio of ethyl acetate to acetone is 8:1, the extraction temperature is 80 ℃, and the extraction time is 40min.
4. The method for separating and purifying linolenic acid from cornus wilsoniana fruit oil according to claim 1, wherein; the concentration of ethanol or methanol in the S2 is 98%.
5. The method for separating and purifying linolenic acid from cornus wilsoniana fruit oil according to claim 1, wherein; the addition amount of the alkali in the S2 is 2 times of the weight of the crude extract, and the saponification reaction temperature is 48 ℃.
6. The method for separating and purifying linolenic acid from cornus wilsoniana fruit oil according to claim 1, wherein; and the pressure of the vacuum rectification in the S4 is 70Pa, and the temperature is 85 ℃.
7. The method for separating and purifying linolenic acid from cornus wilsoniana fruit oil according to claim 1, wherein; the mass ratio of the silica gel to the acrylate polymer in the S5 is 10:1.
8. the method for separating and purifying linolenic acid from cornus wilsoniana fruit oil according to claim 1, wherein; the flow rate of the S5 mobile phase was 0.85 ml/min.
9. The method for separating and purifying linolenic acid from cornus wilsoniana fruit oil according to claim 1, wherein; and the alkali in the S2 is NaOH solution or KOH solution.
10. The method for separating and purifying linolenic acid from cornus wilsoniana fruit oil according to claim 9, wherein; the mass fraction of the NaOH solution or the KOH solution is 2 to 5 percent.
CN202211319210.8A 2022-10-26 2022-10-26 Method for separating and purifying linolenic acid from cornus wilsoniana fruit oil Pending CN115466161A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202211319210.8A CN115466161A (en) 2022-10-26 2022-10-26 Method for separating and purifying linolenic acid from cornus wilsoniana fruit oil

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202211319210.8A CN115466161A (en) 2022-10-26 2022-10-26 Method for separating and purifying linolenic acid from cornus wilsoniana fruit oil

Publications (1)

Publication Number Publication Date
CN115466161A true CN115466161A (en) 2022-12-13

Family

ID=84336804

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202211319210.8A Pending CN115466161A (en) 2022-10-26 2022-10-26 Method for separating and purifying linolenic acid from cornus wilsoniana fruit oil

Country Status (1)

Country Link
CN (1) CN115466161A (en)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101402558A (en) * 2008-05-13 2009-04-08 山西中大科技有限公司右玉分公司 Method for separating and purifying alpha-linolenic acid from cold pressed flax seed oil
CN101892119A (en) * 2010-06-29 2010-11-24 陕西师范大学 Separation method of silkworm pupa oil polyunsaturated fatty acid by gradient freezing crystallization
CN102433217A (en) * 2011-10-25 2012-05-02 江西省粮油科学技术研究所 Method for extracting edible cornus wilsoniana seed oil from fresh cornus wilsoniana seed fruits at low temperature
CN103054018A (en) * 2012-12-25 2013-04-24 广东省农业科学院蚕业与农产品加工研究所 Preparation method for grains capable of assisting to improve memory function
CN105441183A (en) * 2015-12-28 2016-03-30 江苏经贸职业技术学院 Method for preparing edible oil by taking Cornus wilsoniana seeds as raw materials
CN105753689A (en) * 2016-03-15 2016-07-13 宁夏大学 Method of extracting purified Alpha-linolenic acid from linseed oil

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101402558A (en) * 2008-05-13 2009-04-08 山西中大科技有限公司右玉分公司 Method for separating and purifying alpha-linolenic acid from cold pressed flax seed oil
CN101892119A (en) * 2010-06-29 2010-11-24 陕西师范大学 Separation method of silkworm pupa oil polyunsaturated fatty acid by gradient freezing crystallization
CN102433217A (en) * 2011-10-25 2012-05-02 江西省粮油科学技术研究所 Method for extracting edible cornus wilsoniana seed oil from fresh cornus wilsoniana seed fruits at low temperature
CN103054018A (en) * 2012-12-25 2013-04-24 广东省农业科学院蚕业与农产品加工研究所 Preparation method for grains capable of assisting to improve memory function
CN105441183A (en) * 2015-12-28 2016-03-30 江苏经贸职业技术学院 Method for preparing edible oil by taking Cornus wilsoniana seeds as raw materials
CN105753689A (en) * 2016-03-15 2016-07-13 宁夏大学 Method of extracting purified Alpha-linolenic acid from linseed oil

Similar Documents

Publication Publication Date Title
CN106381319B (en) Efficient extraction and separation method for grape seed procyanidin oligomers
CN110386860B (en) Efficient extraction method of cannabidiol
CN102276665A (en) Method of extracting flax lignin from flax seed cake
CN102850219A (en) Method for extracting rosmarinic acid from folia perillae acutae
US20090209789A1 (en) Microwave-assisted extraction of solanesol from potato stems and/or leaves
CN106866381B (en) Method for preparing moso bamboo lignin monophenol compound
CN103610704A (en) Method for extracting brown algae polyphenols
CN102461898A (en) Technological process for extracting flavone from jujube fruits
CN115466161A (en) Method for separating and purifying linolenic acid from cornus wilsoniana fruit oil
CN107190028B (en) The extracting method of ferulic acid in a kind of rice bran meal
CN103524525B (en) The method extracting arteannuinic acid and derivative thereof waste is produced from Artemisinin
CN104974124A (en) Method for extracting procyanidine from dahurian larch barks
CN102432573B (en) Method for preparing lovastatin
CN114015732B (en) Industrial preparation method of andrographolide and dehydroandrographolide
CN110627843A (en) Method for extracting saponin from soapberry pericarp
CN102276570B (en) Method for purifying epigallo catechin gallate (EGCG)
CN107382943B (en) Method for subcritical water extraction of dihydroquercetin in sorghum bran
CN113501752B (en) Acid purification method of coenzyme Q10
CN115710294A (en) Method for extracting astragalus flavone by treating high-viscosity eutectic solvent through circulating pulse ultrasonic
CN111943827B (en) Method for purifying coenzyme Q10
CN105585551B (en) A kind of method for hydrolysis of astilbin
CN104529739A (en) Purification method of unsaturated fatty acid
CN112592765B (en) Preparation method of garlic essential oil
CN114773196B (en) Purification method of high-carbon methacrylate
CN102876753A (en) Separation and purification method for ferulic acid and xylo-oligosaccharide in spent grains

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination