CN107418737A - The preparation method of unrighted acid in a kind of Silybum Marianum Gaertn Seed Oil - Google Patents
The preparation method of unrighted acid in a kind of Silybum Marianum Gaertn Seed Oil Download PDFInfo
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- CN107418737A CN107418737A CN201710417924.5A CN201710417924A CN107418737A CN 107418737 A CN107418737 A CN 107418737A CN 201710417924 A CN201710417924 A CN 201710417924A CN 107418737 A CN107418737 A CN 107418737A
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- seed oil
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- marianum gaertn
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
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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
- C07C67/60—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
- C11C1/04—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
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Abstract
The invention discloses a kind of preparation method of unrighted acid in Silybum Marianum Gaertn Seed Oil, including：S1：Silybum Marianum Gaertn Seed Oil is added in NaOH alcoholic solution, backflow, take supernatant liquor；S2：The ethanol solution containing urea is added into supernatant liquor, heating stirring cools stirring again, progress urea clathrate；S3：S2 is obtained into thing decompression to filter, the gains after filtrate recycling ethanol solvent are dissolved in water, then add hydrochloric acid to be adjusted to faintly acid, then are washed to neutrality, centrifugal drying, obtain unsaturated fatty acid ester；S4：The filter cake that S3 is obtained adds ethanol solution, repeats S2 and S3 steps；S5：It will merge obtained by S3 and S4, add in the NaOH aqueous solution, heating stirring, after stopping reaction, add hydrochloric acid to be adjusted to acidity, stratification, take upper strata to be washed to neutrality, centrifugal drying, obtain unrighted acid.Method flow of the present invention is clear, method is simple, cost is low, and the product colour for purifying to obtain is good, yield is high, can extract unsaturated fatty acid ester and aliphatic acid to greatest extent.
Description
Technical field
The present invention relates to a kind of preparation method of unrighted acid, and in particular to unsaturated fat in a kind of Silybum Marianum Gaertn Seed Oil
The preparation method of acid, belongs to pharmaceutical chemistry technical field.
Background technology
Milk thistle is a kind of the medicinal plants of Compositae, originates in north African, and last century the seventies are introduced behind China as one kind
Liver protection medicinal plant is widely popularized plantation.Amount of literature data research shows, a large amount of flavonoids are contained in milk thistle seed
Representative compound-silymarin in compound, wherein flavone compound, there is Scavenger of ROS, confrontation lipid mistake
Oxidation, anti-hepatotoxin, promote the pharmacological activities such as liver cell reparation, antitumor, reducing blood lipid generally known by people.
Remove flavone compound, contain a large amount of unrighted acids in milk thistle seed, oil content due to region not
Together, content is more than 20% to 30%.The Main Ingredients and Appearance of Silybum Marianum Gaertn Seed Oil is unrighted acid, is fat needed by human
Acid, unrighted acid have linoleic acid, leukotrienes and oleic acid, and composition is wanted based on its Linoleic acid.Unrighted acid, particularly
Double bond unrighted acid is combined formed ester with cholesterol and easily transports, is metabolized and drains.Linoleic acid, leukotrienes category are more not
Saturated fatty acid, the oxidation of cholesterol in enteron aisle can be promoted, increase the discharge rate of excrement, and increase the elasticity of capilary, can pressed down
The formation of thrombus processed.Therefore Silybum Marianum Gaertn Seed Oil not only has preventive and therapeutic action to atherosclerosis, and to increasingly common
Fatty liver also have a good preventive and therapeutic effect, also with reducing plasma cholesterol and treat the effect of hypertension.
There is substantial amounts of Silybum Marianum Gaertn Seed Oil to sell on the market at present, but the research to its unrighted acid is prepared seldom, is
Milk thistle is set farthest to be used, the invention provides a kind of preparation side of unrighted acid in Silybum Marianum Gaertn Seed Oil
Method.
The content of the invention
To solve the deficiencies in the prior art, it is an object of the invention to provide a kind of method is simple, cost is low, final product
The preparation method of the high unrighted acid of content.
In order to realize above-mentioned target, the present invention adopts the following technical scheme that：
The preparation method of unrighted acid, comprises the following steps in a kind of Silybum Marianum Gaertn Seed Oil：
S1 ester exchanges：Silybum Marianum Gaertn Seed Oil is added in NaOH ethanol or methanol solution, and Silybum Marianum Gaertn Seed Oil, NaOH and ethanol or methanol
The mass ratio of solution is：1 ︰（0.01-0.04）︰（3-8）, flow back 4-8h under the conditions of 60-85 DEG C, reclaims ethanol or methanol, liquid
Body is layered, and takes supernatant liquor, lower floor is glycerine；
S2 urea clathrates：The ethanol solution that the concentration containing urea is 80-95% is added into supernatant liquor, 70-80 DEG C of heating is stirred
20-50min is mixed, is then cooled to 5-15 DEG C with 0.5 DEG C per minute of speed, stirs 2-8h at this temperature, carries out urea bag
Close, obtain urea clathrate liquid；
S3 prepares unsaturated fatty acid ester：The urea clathrate liquid of S2 steps is filtered in 10 DEG C of decompressions, filtrate recycling ethanol solvent,
Gains after recovery alcohol solvent add 40-60 DEG C of the water dissolving of 2-6 times of gained amount of substance, then add the hydrochloric acid that concentration is 10%
Tune pH value is 4-6, is then washed to neutrality again, centrifugal drying, obtains unsaturated fatty acid ester；
Bis- urea clathrates of S4：It is that 80-95% ethanol is molten that the filter cake obtained in S3 steps is added into 2-6 times of filter cake quality and concentration
Liquid, secondary urea clathrate is carried out, repeat the operation of S2 and S3 steps, obtain unsaturated fatty acid ester；
S5 is hydrolyzed：After unsaturated fatty acid ester resulting in S3 and S4 steps is merged, addition weight/mass percentage composition is 1-3%
The NaOH aqueous solution in, the heating stirring 4-8h under 60-80 DEG C of temperature conditionss, after stopping reaction, add the weight/mass percentage composition to be
It is 4-6 that 20% hydrochloric acid, which adjusts pH value, stratification, takes upper strata to be washed to neutrality, centrifugal drying, obtains unrighted acid.
Further, after S4 steps, in addition to the step of recovery urea, it is specially：The filter that will be finally given in S4 steps
Cake adds 40-60 DEG C of the water dissolving of 1-5 times of filter cake quality, layering, removes upper strata fluid, lower floor is heated to water and largely volatilized, cold
Static, urea is separated out, and obtained urea is reused.
And in the step of reclaiming urea, the quality for 40-60 DEG C of water of dissolving is preferably 1-3 times of filter cake.
And in S1 steps, when alcoholic solution is ethanol, the mass ratio of above-mentioned Silybum Marianum Gaertn Seed Oil, NaOH and ethanol is preferred
For：1 ︰（0.01-0.04）︰（5-8）, and the reaction temperature of ethanol is preferably 75-85 DEG C.
When alcoholic solution is methanol, the mass ratio of above-mentioned Silybum Marianum Gaertn Seed Oil, NaOH and methanol is preferably：1 ︰（0.01-
0.04）︰（3-6）, and the reaction temperature of methanol is preferably 60-75 DEG C.
And in S2 steps, above-mentioned supernatant liquor, urea, the mass ratio of ethanol solution are preferably：1 ︰（1-2.5）︰
（2.5-6）, and the preferred 3-6h of mixing time.
The present invention is advantageous in that：Method flow of the present invention is clear, method is simple, cost is low, purifies
The product colour that arrives is good, yield more than 50%, can extract unsaturated fatty acid ester and aliphatic acid to greatest extent.
Embodiment
Make specific introduce to the present invention below in conjunction with specific embodiment.
Embodiment 1
10kg Silybum Marianum Gaertn Seed Oils are added in NaOH ethanol solution, and the mass ratio of Silybum Marianum Gaertn Seed Oil, NaOH and ethanol solution is：1 ︰
0.01 ︰ 6, flow back 5h under the conditions of 75 DEG C, reclaims ethanol, liquid layered, takes supernatant liquor（Lower floor is glycerine）；To supernatant liquor
Middle to add the ethanol solution that the concentration containing urea is 95%, supernatant liquor, urea, the mass ratio of ethanol solution are：The ︰ 4,70 of 1 ︰ 2
DEG C heating stirring 30min, is then cooled to 10 ± 2 DEG C with 0.5 DEG C per minute of speed, stirs 4h at this temperature, urinated
Element inclusion, obtains urea clathrate liquid；Urea clathrate liquid is filtered in 10 ± 2 DEG C of decompressions afterwards, filtrate recycling ethanol solvent, reclaims second
Gains after alcoholic solvent add 50 DEG C of the water dissolving of 3 times of gained amount of substance, then it is 4-5 to add the hydrochloric acid that concentration is 10% to adjust pH value
（Faintly acid, the detection of PH test paper）, neutrality is then washed to again, centrifugal drying, obtains unsaturated fatty acid ester 6.5kg；Filter cake adds 3
Times filter cake quality and concentration is 95% ethanol solution, carries out secondary urea clathrate, repeats urea clathrate operation above, obtain insatiable hunger
With fatty acid ester 1.5kg；60 DEG C of the water that the filter cake obtained after secondary urea clathrate is added to 1 times of filter cake quality dissolves,
Layering, removes upper strata fluid, and lower floor is heated to water and largely volatilized, and cooling is static, and urea separates out, and obtained urea is reused.Institute
Obtained unsaturated fatty acid ester 8kg is added in the NaOH aqueous solution that 25L weight/mass percentage compositions are 1%, in 80 DEG C of temperature conditionss
Lower heating stirring 5h, after stopping reaction, it is 4-5 to add the hydrochloric acid that weight/mass percentage composition is 20% to adjust pH value（Acidity, the inspection of PH test paper
Survey）, stratification, take upper strata to be washed to neutrality, centrifugal drying, obtain unrighted acid 5.7kg.
Embodiment 2
10kg Silybum Marianum Gaertn Seed Oils are added in NaOH methanol solution, and the mass ratio of Silybum Marianum Gaertn Seed Oil, NaOH and methanol solution is：1 ︰
0.01 ︰ 4, flow back 5h under the conditions of 70 DEG C, reclaims methanol, liquid layered, takes supernatant liquor（Lower floor is glycerine）；To supernatant liquor
Middle to add the ethanol solution that the concentration containing urea is 95%, supernatant liquor, urea, the mass ratio of ethanol solution are：The ︰ 4 of 1 ︰ 1.5,
80 DEG C of heating stirring 30min, are then cooled to 10 ± 2 DEG C with 0.5 DEG C per minute of speed, stir 3h at this temperature, carry out
Urea clathrate, obtain urea clathrate liquid；Urea clathrate liquid is filtered in 8 ± 2 DEG C of decompressions afterwards, filtrate recycling ethanol solvent, recovery
Gains after alcohol solvent add 50 DEG C of the water dissolving of 4 times of gained amount of substance, then it is 5- to add the hydrochloric acid that concentration is 10% to adjust pH value
6（Faintly acid, the detection of PH test paper）, neutrality is then washed to again, centrifugal drying, obtains unsaturated fatty acid ester 7.0kg；Filter cake adds
3 times of filter cake qualities and concentration is 85% ethanol solution, secondary urea clathrate is carried out, repeat urea clathrate operation above, obtain insatiable hunger
With fatty acid ester 1.4kg；60 DEG C of the water that the filter cake obtained after secondary urea clathrate is added to 2 times of filter cake qualities dissolves,
Layering, removes upper strata fluid, and lower floor is heated to water and largely volatilized, and cooling is static, and urea separates out, and obtained urea is reused.Institute
Obtained unsaturated fatty acid ester 8.4kg is added in the NaOH aqueous solution that 28L weight/mass percentage compositions are 3%, in 70 DEG C of temperature strip
Heating stirring 4h under part, after stopping reaction, it is 5-6 to add the hydrochloric acid that weight/mass percentage composition is 20% to adjust pH value（Acidity, the inspection of PH test paper
Survey）, stratification, take upper strata to be washed to neutrality, centrifugal drying, obtain unrighted acid 5.8kg.
Embodiment 3
10kg Silybum Marianum Gaertn Seed Oils are added in NaOH ethanol solution, and the mass ratio of Silybum Marianum Gaertn Seed Oil, NaOH and ethanol solution is：1 ︰
0.02 ︰ 7, flow back 6h under the conditions of 80 DEG C, reclaims ethanol, liquid layered, takes supernatant liquor（Lower floor is glycerine）；To supernatant liquor
Middle to add the ethanol solution that the concentration containing urea is 95%, supernatant liquor, urea, the mass ratio of ethanol solution are：The ︰ 4 of 1 ︰ 2.5,
80 DEG C of heating stirring 40min, are then cooled to 10 ± 3 DEG C with 0.5 DEG C per minute of speed, stir 6h at this temperature, carry out
Urea clathrate, obtain urea clathrate liquid；Urea clathrate liquid is filtered in 12 ± 3 DEG C of decompressions afterwards, filtrate recycling ethanol solvent, recovery
Gains after alcohol solvent add 50 DEG C of the water dissolving of 3 times of gained amount of substance, then it is 5- to add the hydrochloric acid that concentration is 10% to adjust pH value
6（Faintly acid, the detection of PH test paper）, neutrality is then washed to again, centrifugal drying, obtains unsaturated fatty acid ester 6.5kg；Filter cake adds
4 times of filter cake qualities and concentration is 85% ethanol solution, secondary urea clathrate is carried out, repeat urea clathrate operation above, obtain insatiable hunger
With fatty acid ester 1.7kg；60 DEG C of the water that the filter cake obtained after secondary urea clathrate is added to 2 times of filter cake qualities dissolves,
Layering, removes upper strata fluid, and lower floor is heated to water and largely volatilized, and cooling is static, and urea separates out, and obtained urea is reused.Institute
Obtained unsaturated fatty acid ester 8.2kg is added in the NaOH aqueous solution that 25L weight/mass percentage compositions are 2%, in 70 DEG C of temperature strip
Heating stirring 8h under part, after stopping reaction, it is 5-6 to add the hydrochloric acid that weight/mass percentage composition is 20% to adjust pH value（Acidity, the inspection of PH test paper
Survey）, stratification, take upper strata to be washed to neutrality, centrifugal drying, obtain unrighted acid 5.9kg.
The basic principles, principal features and advantages of the present invention have been shown and described above.It should be understood by those skilled in the art that
The invention is not limited in any way for above-described embodiment, all technical sides obtained by the way of equivalent substitution or equivalent transformation
Case, all fall within protection scope of the present invention.
Claims (9)
1. the preparation method of unrighted acid in a kind of Silybum Marianum Gaertn Seed Oil, it is characterised in that comprise the following steps：
S1 ester exchanges：Silybum Marianum Gaertn Seed Oil is added in NaOH ethanol or methanol solution, and Silybum Marianum Gaertn Seed Oil, NaOH and ethanol or methanol
The mass ratio of solution is：1 ︰（0.01-0.04）︰（3-8）, flow back 4-8h under the conditions of 60-85 DEG C, reclaims ethanol or methanol, liquid
Body is layered, and takes supernatant liquor；
S2 urea clathrates：The ethanol solution that the concentration containing urea is 80-95%, 70-80 DEG C of heating are added into supernatant liquor
20-50min is stirred, is then cooled to 5-15 DEG C with 0.5 DEG C per minute of speed, stirs 2-8h at this temperature, carries out urea
Inclusion, obtains urea clathrate liquid；
S3 prepares unsaturated fatty acid ester：The urea clathrate liquid of S2 steps is filtered in 10 ± 5 DEG C of decompressions, filtrate recycling ethanol is molten
Agent, reclaim the gains after alcohol solvent and add 40-60 DEG C of the water dissolving of 2-6 times of gained amount of substance, then add the salt that concentration is 10%
It is 4-6 that acid, which adjusts pH value, is then washed to neutrality again, centrifugal drying, obtains unsaturated fatty acid ester；
Bis- urea clathrates of S4：It is that 80-95% ethanol is molten that the filter cake obtained in S3 steps is added into 2-6 times of filter cake quality and concentration
Liquid, secondary urea clathrate is carried out, repeat the operation of S2 and S3 steps, obtain unsaturated fatty acid ester；
S5 is hydrolyzed：After unsaturated fatty acid ester resulting in S3 and S4 steps is merged, addition weight/mass percentage composition is 1-3%
The NaOH aqueous solution in, the heating stirring 4-8h under 60-80 DEG C of temperature conditionss, after stopping reaction, add the weight/mass percentage composition to be
It is 4-6 that 20% hydrochloric acid, which adjusts pH value, stratification, takes upper strata to be washed to neutrality, centrifugal drying, obtains unrighted acid.
2. the preparation method of unrighted acid in a kind of Silybum Marianum Gaertn Seed Oil according to claim 1, it is characterised in that in S4
After step, in addition to the step of recovery urea, it is specially：The filter cake finally given in S4 steps is added into 1-5 times of filter cake quality
40-60 DEG C of water dissolving, layering, remove upper strata fluid, lower floor is heated to water and largely volatilized, cooling it is static, urea separate out, obtain
Urea reuse.
3. the preparation method of unrighted acid in a kind of Silybum Marianum Gaertn Seed Oil according to claim 2, it is characterised in that returning
In the step of receiving urea, the quality for 40-60 DEG C of water of dissolving is 1-3 times of filter cake.
4. the preparation method of unrighted acid in a kind of Silybum Marianum Gaertn Seed Oil according to claim 1, it is characterised in that in S1
In step, the mass ratio of described Silybum Marianum Gaertn Seed Oil, NaOH and ethanol is：1 ︰（0.01-0.04）︰（5-8）.
5. the preparation method of unrighted acid in a kind of Silybum Marianum Gaertn Seed Oil according to claim 1, it is characterised in that in S1
In step, the mass ratio of described Silybum Marianum Gaertn Seed Oil, NaOH and methanol is：1 ︰（0.01-0.04）︰（3-6）.
6. the preparation method of unrighted acid in a kind of Silybum Marianum Gaertn Seed Oil according to claim 1, it is characterised in that in S1
In step, the reaction temperature of described ethanol is 75-85 DEG C.
7. the preparation method of unrighted acid in a kind of Silybum Marianum Gaertn Seed Oil according to claim 1, it is characterised in that in S1
In step, the reaction temperature of described methanol is 60-75 DEG C.
8. the preparation method of unrighted acid in a kind of Silybum Marianum Gaertn Seed Oil according to claim 1, it is characterised in that in S2
In step, described supernatant liquor, urea, the mass ratio of ethanol solution are：1 ︰（1-2.5）︰（2.5-6）.
9. the preparation method of unrighted acid in a kind of Silybum Marianum Gaertn Seed Oil according to claim 1, it is characterised in that in S2
In step, described mixing time is 3-6h.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110872540A (en) * | 2019-12-25 | 2020-03-10 | 四川欣美加生物医药有限公司 | Method for extracting unsaturated fatty acid |
| CN112708508A (en) * | 2020-12-25 | 2021-04-27 | 江苏天晟药业股份有限公司 | Preparation method of unsaturated fatty acid in macadamia nut oil |
| CN113046186A (en) * | 2019-12-26 | 2021-06-29 | 江苏天晟药业股份有限公司 | Preparation method of unsaturated fatty acid in safflower seed oil |
| CN113599305A (en) * | 2021-07-26 | 2021-11-05 | 湖南中医药大学 | Walnut oil soap-based silicone oil-free shampoo and preparation method thereof |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113046186A (en) * | 2019-12-26 | 2021-06-29 | 江苏天晟药业股份有限公司 | Preparation method of unsaturated fatty acid in safflower seed oil |
| CN112708508A (en) * | 2020-12-25 | 2021-04-27 | 江苏天晟药业股份有限公司 | Preparation method of unsaturated fatty acid in macadamia nut oil |
| CN113599305A (en) * | 2021-07-26 | 2021-11-05 | 湖南中医药大学 | Walnut oil soap-based silicone oil-free shampoo and preparation method thereof |
| CN113599305B (en) * | 2021-07-26 | 2023-11-28 | 湖南中医药大学 | Walnut oil soap base silicone oil-free shampoo and preparation method thereof |
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