CN108715577A - A method of extracting high-purity isodextropimaric acid from pine-seed oil - Google Patents
A method of extracting high-purity isodextropimaric acid from pine-seed oil Download PDFInfo
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- C07C51/42—Separation; Purification; Stabilisation; Use of additives
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Abstract
The present invention relates to a kind of methods for extracting high-purity isodextropimaric acid from five leaf pine-seed oils, using following steps:A, five leaf pine-seed oils are mixed by volume with potassium hydroxide-ethanol solution, carries out saponification, takes clear filtrate to add HCl, take upper layer fluid, mixture A is made;B, urea is mixed with methanol, mixture A is added dropwise, stirring filters, removal inclusion compound;It by filtrate methanol removed by evaporation, is diluted with water, then adds HCl;With n-hexane extraction, mixture B is obtained;C, mixture B is dissolved in acetone, isobutyl hydramine is added, stood, filter, washing, obtaining isodextropimaric acid ammonium salt crude product;Then ethyl alcohol purification is used, the isodextropimaric acid ammonium salt crystal of purifying is put into ether, HCl/water solution is added and disappears to crystallizing, it takes ether layer to be washed with water, ether is evaporated off, residue is dissolved in acetone, it adds water to crystallization not to be further added by, then filters, is dried in vacuo to get isodextropimaric acid.The present invention has the advantages that gained isodextropimaric acid purity is high, at low cost, yield is high.
Description
Technical field
The invention belongs to plant extracts field, more particularly to a kind of side extracting high-purity isodextropimaric acid from pine-seed oil
Method.
Technical background
Pimaric type acid refer on C-13 tertiary carbon atoms while gathering around there are one methyl and a vinyl, and point
Sub- internal double bond is a kind of diterpenoid resin acid (C of non-conjugated independent double bond19H29COOH general name) includes mainly pimaric acid, different sea
Several isomers such as loose acid, sandaracopimaric acid.Wherein, isodextropimaric acid is widely present in the resin of nearly all pine genus plant
(That is rosin), in the rosin in especially various sources, meanwhile, in the plants such as Japan cypress, Phoenicia Chinese juniper, false ground maple, arrowhead, Chinese torreya
Also acquisition isodextropimaric acid can be extracted.Isodextropimaric acid has the biologies such as antibacterial, anti-inflammatory, antimicrobial, desinsection, norcholesterol, anticancer
Activity has extensive use in pesticide and field of medicaments.
In domestic and international existing literature and patent report, most of is that separation prepares isodextropimaric acid from rosin.It is currently known
Isodextropimaric acid separation and method of purification include alkali metal salt method, the direct ammonium salt precipitation method, Malaysia derivatization method, benzoquinones derive
Change method and rectification method.Due in the rosin of most of types, the content higher of abietic type acid, and exist simultaneously mountain and reach Korean pine
Isomers such as acid, pimaric acid, therefore prepare isodextropimaric acid using rosin as source separation, generally existing recovery rate is low, product
The low deficiency of purity, and above method flow is complicated, cost is higher, seriously polluted, it is more difficult to realize industrialization large-scale production.
Pine tree is resourceful in China, is distributed mainly on the Northeast.Pine-seed oil is the oil that the fruit SEMEN PINI KORAIENSIS of pine tree is produced
Fat, Related product are mainly used in food, medicine and field of health care products.It is at home, less about the research of the report of pine-seed oil,
Most of researchs are also concentrated mainly in the measurement of the extraction process of pine-seed oil, physical and chemical index and aliphatic acid composition, about from pine
Extraction obtains the research of isodextropimaric acid and has not been reported in seed oil.Due to also having more isodextropimaric acid in pine-seed oil, if energy
It extracts to obtain high-purity isodextropimaric acid using resourceful pine-seed oil as raw material, the raw material that can not only expand isodextropimaric acid comes
Source, moreover it is possible to the added value of effective exploitation pine-seed oil.
Separation obtains the difference of isodextropimaric acid and essentially consists in from different material, and the impurity composition in raw material is different.It prepares
The overriding concern of rosin source isodextropimaric acid is the abietic type acid of high-content in removing rosin, and using pine-seed oil as source,
Technical essential is then to detach isodextropimaric acid and oleic acid, linoleic acid and pinolenic acid etc..In other words, separation is extracted from rosin
The technique of isodextropimaric acid is not particularly suited for the extraction of pine nut oil sources isodextropimaric acid.Therefore, a kind of high-purity, high yield pulp1, height are explored
Efficiency and economically viable pine nut oil sources isodextropimaric acid preparation method are conducive to accelerate isodextropimaric acid in medicine, biology and agricultural
The application in field.
Invention content
The technical problem to be solved by the present invention is to, a kind of method for extracting isodextropimaric acid from five leaf pine-seed oils is provided, it should
Method extraction isodextropimaric acid purity higher and have the advantages that production cost is low, extraction yield is high.
In order to solve the above technical problems, the present invention uses following technical scheme:One kind is extracted high-purity from five leaf pine-seed oils
The method of isodextropimaric acid, it is characterised in that use following steps:
A, by the potassium hydroxide-ethanol solution of five leaf pine-seed oils and a concentration of 0.5 ~ 1.0 mol/L according to 1:3 ~ 7 volume ratio is mixed
It closes, 65 ~ 75oUnder C counterflow conditions, maintains stirring to oil droplet to disappear, obtain saponification liquor;The saponification liquor is cooled to room temperature, is taken out
It filters off and removes unsaponifiable matter, take clear filtrate to be concentrated, obtain concentrate, the HCl/water solution of a concentration of 6mol/L is added, adjust
The pH to 2-4 of the concentrate;The upper layer fluid of the concentrate, evaporative removal residual solvent is taken to obtain mixture A;
B, in mass ratio 1:3~8:6 ~ 12 weigh mixture A, urea and methanol obtained by step A respectively, by the urea and methanol
Mixing, 65oIt is stirred at reflux to clear under C, the mixture A is added dropwise, stirring is to being uniformly mixed, 65oIt is kept the temperature back under C
Flow 30 ~ 60min;It is subsequently cooled to -5 ~ 10o10 ~ 18h is placed in C, heat preservation, then rapid to filter, and removes inclusion compound;Filtrate is revolved
Turn methanol removed by evaporation, the water isometric with filtrate is then added and is diluted, adds the HCl/water solution of a concentration of 3mol/L
It is acidified to system pH 2 ~ 4;With n-hexane extraction, water layer is discarded, rotary evaporation removes n-hexane, obtains mixture B;
C, mixture B obtained by step B is dissolved in acetone, the acetone quality is 2 ~ 8 times of mixture B mass, is slowly added
Enter isobutyl hydramine, the addition of isobutyl hydramine is the 10 ~ 45% of mixture B mass, stirs 1 ~ 3h, quiet after complete formation to be precipitated
It sets, filters, it is dry after washing 3 times with the ethyl alcohol of volume fraction 50%, obtain isodextropimaric acid ammonium salt crude product;Isodextropimaric acid ammonium salt is thick
The ethanol water that product are 95% with volume fraction carries out 3 ~ 6 recrystallization purifications using compound recrystallization method, obtains isodextropimaric acid
Ammonium salt crystal;The isodextropimaric acid ammonium salt crystal of purifying is put into appropriate ether, the HCl/water that a concentration of 3mol/L is then added is molten
Liquid takes ether layer to be washed with water to neutrality, ether is evaporated off, residue is dissolved in proper amount of acetone, be slowly added dropwise to disappearance is crystallized
Then water filters until crystallization is not further added by, gained is crystallized vacuum drying to get isodextropimaric acid.
The purity of gained isodextropimaric acid of the invention is higher than patent document CN 200810123831.2 up to 97.8% or more《It is different
The preparation method of pimaric acid》The isodextropimaric acid purity that disclosed preparation method is realized is up to 95%.The present invention is with five leaf pine-seed oils
Raw material extracts, and relative to isodextropimaric acid is extracted from rosin, has product purity high, technological process is simple, at low cost
Advantage.
The principle of extracting method of the present invention is as follows:
The saponification of step A makes aliphatic acid, resin acid and corresponding esters be converted to salt, on the one hand can reduce by five leaves pine
The solubility in seed oil with certain water-soluble glucide, is allowed to be precipitated;On the other hand, it can be achieved that with unsaponifiable matter such as egg
The separation of white matter.After step A separation, main group of mixture A becomes:Saturated fatty acid(Palmitic acid, stearic acid), single insatiable hunger
With fatty aliphatic acid(Oleic acid), polyunsaturated fatty acid(Linoleic acid, pinolenic acid)And resin acid.
Step B uses urea adduct method, and initial gross separation is carried out to mixture A obtained by step A.Urea molecule is in crystallization process
It is middle can be with the saturated fatty acid in mixture A(Palmitic acid, stearic acid), monounsaturated fatty acids(Oleic acid)With part multivalence insatiable hunger
And aliphatic acid(Linoleic acid)Relatively stable crystal inclusion compound is formed to be precipitated, and pinolenic acid and resin acid are due to certain space
Configuration is not easy by urea clathrate.Resin acid and saturated fatty acid, oleic acid, part linoleic acid can be carried out using the method for filtering
It efficiently separates.After step B separation, the impurity in mixture B is mainly a small amount of linoleic acid and the less pinolenic acid of content.
Step C using isobutyl hydramine to the selective precipitation of isodextropimaric acid, the isodextropimaric acid in separation and Extraction mixture B,
Realization isodextropimaric acid is efficiently separated with other resin acids.
The present invention provides a kind of method for extracting high-purity isodextropimaric acid from five leaf pine-seed oils, has the advantages that:
1. the technique being combined using saponification method, urea adduct method and the ammonium salt precipitation method, is removed successively in five leaf pine-seed oils
The unsaponifiable matter such as carbohydrate, protein, aliphatic acid and other types resin acid, can effectively improve the pure of target product isodextropimaric acid
Degree finally obtains the isodextropimaric acid sterling that purity is higher than 97.8%.
2. the present invention provides a kind of preparation methods of five leaves pine nut oil sources isodextropimaric acid product, compared to from rosin
Isodextropimaric acid is extracted, has technological process simple, production cost is low, the high advantage of product purity.
Specific implementation mode:
It is described further below by embodiment, the range of but do not limit the invention in any way.
Embodiment 1:A method of extracting high-purity isodextropimaric acid from five leaf pine-seed oils, it is characterised in that use following step
Suddenly:
A, by the potassium hydroxide-ethanol solution of five leaf pine-seed oils and a concentration of 0.5 mol/L according to 1:7 volume ratio mixing,
65oUnder C counterflow conditions, maintains stirring to oil droplet to disappear, obtain saponification liquor;The saponification liquor is cooled to room temperature, filters removal not
It is saponified, it takes clear filtrate to be concentrated, obtains concentrate, the HCl/water solution of a concentration of 6mol/L is added, adjusts the concentration
The pH to 2 of liquid;The upper layer fluid of the concentrate, evaporative removal residual solvent is taken to obtain mixture A;
B, in mass ratio 1:3:6 weigh mixture A, urea and methanol obtained by step A respectively, and the urea is mixed with methanol,
65oIt is stirred at reflux to clear under C, the mixture A is added dropwise, stirring is to being uniformly mixed, 65oReflux is kept the temperature under C
30min;It is subsequently cooled to 0o12h is placed in C, heat preservation, then rapid to filter, and removes inclusion compound;Filtrate rotary evaporation is removed into first
Then alcohol is added the water isometric with filtrate and is diluted, adds 3mol/L HCl/water solution and be acidified to system pH 2;With just
Hexane extracts, and discards water layer, and rotary evaporation removes n-hexane, obtains mixture B;
C, mixture B obtained by step B is dissolved in acetone, the acetone quality is 4 times of mixture B mass, is slowly added to
Isobutyl hydramine, the addition of isobutyl hydramine are the 20% of mixture B mass, stir 1h, after complete formation to be precipitated, stand, take out
Filter, it is dry after washing 3 times with the ethyl alcohol of volume fraction 50%, obtain isodextropimaric acid ammonium salt crude product;By isodextropimaric acid ammonium salt crude product body
The ethanol water that fraction is 95% carries out 4 recrystallization purifications using compound recrystallization method, and it is brilliant to obtain isodextropimaric acid ammonium salt
Body;Will purifying isodextropimaric acid ammonium salt crystal input ether in, then be added 3mol/L HCl/waters solution to crystallize disappear, take second
Ether layer is washed with water to neutrality, and ether is evaporated off, and residue is dissolved in acetone, slowly drop add water to crystallization be not further added by until,
Then it filters, gained is crystallized into vacuum drying to get isodextropimaric acid, purity 97.8%.
Embodiment 2:A method of extracting high-purity isodextropimaric acid from five leaf pine-seed oils, it is characterised in that use following step
Suddenly:
A, by the potassium hydroxide-ethanol solution of five leaf pine-seed oils and a concentration of 0.7 mol/L according to 1:4 volume ratio mixing,
70oUnder C counterflow conditions, maintains stirring to oil droplet to disappear, obtain saponification liquor;The saponification liquor is cooled to room temperature, filters removal not
It is saponified, it takes clear filtrate to be concentrated, obtains concentrate, the HCl/water solution of a concentration of 6mol/L is added, adjusts the concentration
The pH to 2.6 of liquid;The upper layer fluid of the concentrate, evaporative removal residual solvent is taken to obtain mixture A;
B, in mass ratio 1:5:8 weigh mixture A, urea and methanol obtained by step A respectively, and the urea is mixed with methanol,
65oIt is stirred at reflux to clear under C, the mixture A is added dropwise, stirring is to being uniformly mixed, 65oReflux is kept the temperature under C
40min;It is subsequently cooled to -5o10h is placed in C, heat preservation, then rapid to filter, and removes inclusion compound;Filtrate rotary evaporation is removed into first
Then alcohol is added the water isometric with filtrate and is diluted, adds 3mol/L HCl/water solution and be acidified to system pH 2.6;With
N-hexane extraction, discards water layer, and rotary evaporation removes n-hexane, obtains mixture B;
C, mixture B obtained by step B is dissolved in acetone, the acetone quality is 2 times of mixture B mass, is slowly added to
Isobutyl hydramine, the addition of isobutyl hydramine are the 10% of mixture B mass, stir 2h, after complete formation to be precipitated, stand, take out
Filter, it is dry after washing 3 times with the ethyl alcohol of volume fraction 50%, obtain isodextropimaric acid ammonium salt crude product;By isodextropimaric acid ammonium salt crude product body
The ethanol water that fraction is 95% carries out 5 recrystallization purifications using compound recrystallization method, and it is brilliant to obtain isodextropimaric acid ammonium salt
Body;Will purifying isodextropimaric acid ammonium salt crystal input ether in, then be added 3mol/L HCl/waters solution to crystallize disappear, take second
Ether layer is washed with water to neutrality, and ether is evaporated off, and residue is dissolved in acetone, slowly drop add water to crystallization be not further added by until,
Then it filters, gained is crystallized into vacuum drying to get isodextropimaric acid, purity 98.8%.
Embodiment 3:A method of extracting high-purity isodextropimaric acid from five leaf pine-seed oils, it is characterised in that use following step
Suddenly:
A, by the potassium hydroxide-ethanol solution of five leaf pine-seed oils and a concentration of 0.9 mol/L according to 1:6 volume ratio mixing,
75oUnder C counterflow conditions, maintains stirring to oil droplet to disappear, obtain saponification liquor;The saponification liquor is cooled to room temperature, filters removal not
It is saponified, it takes clear filtrate to be concentrated, obtains concentrate, the HCl/water solution of a concentration of 6mol/L is added, adjusts the concentration
The pH to 3.4 of liquid;The upper layer fluid of the concentrate, evaporative removal residual solvent is taken to obtain mixture A;
B, in mass ratio 1:8:12 weigh mixture A, urea and methanol obtained by step A respectively, and the urea is mixed with methanol,
65oIt is stirred at reflux to clear under C, the mixture A is added dropwise, stirring is to being uniformly mixed, 65oReflux is kept the temperature under C
50min;It is subsequently cooled to 5o16h is placed in C, heat preservation, then rapid to filter, and removes inclusion compound;Filtrate rotary evaporation is removed into first
Then alcohol is added the water isometric with filtrate and is diluted, adds 3mol/L HCl/water solution and be acidified to system pH 3.4;With
N-hexane extraction, discards water layer, and rotary evaporation removes n-hexane, obtains mixture B;
C, mixture B obtained by step B is dissolved in acetone, the acetone quality is 6 times of mixture B mass, is slowly added to
Isobutyl hydramine, the addition of isobutyl hydramine are the 30% of mixture B mass, stir 2.5h, after complete formation to be precipitated, stand, take out
Filter, it is dry after washing 3 times with the ethyl alcohol of volume fraction 50%, obtain isodextropimaric acid ammonium salt crude product;By isodextropimaric acid ammonium salt crude product body
The ethanol water that fraction is 95% carries out 3 recrystallization purifications using compound recrystallization method, and it is brilliant to obtain isodextropimaric acid ammonium salt
Body;Will purifying isodextropimaric acid ammonium salt crystal input ether in, then be added 3mol/L HCl/waters solution to crystallize disappear, take second
Ether layer is washed with water to neutrality, and ether is evaporated off, and residue is dissolved in acetone, slowly drop add water to crystallization be not further added by until,
Then it filters, gained is crystallized into vacuum drying to get isodextropimaric acid, purity 98.5%.
Embodiment 4:A method of extracting high-purity isodextropimaric acid from five leaf pine-seed oils, it is characterised in that use following step
Suddenly:
A, by the potassium hydroxide-ethanol solution of five leaf pine-seed oils and a concentration of 1.0 mol/L according to 1:3 volume ratio mixing,
68oUnder C counterflow conditions, maintains stirring to oil droplet to disappear, obtain saponification liquor;The saponification liquor is cooled to room temperature, filters removal not
It is saponified, it takes clear filtrate to be concentrated, obtains concentrate, the HCl/water solution of a concentration of 6mol/L is added, adjusts the concentration
The pH to 4.0 of liquid;The upper layer fluid of the concentrate, evaporative removal residual solvent is taken to obtain mixture A;
B, in mass ratio 1:6:10 weigh mixture A, urea and methanol obtained by step A respectively, and the urea is mixed with methanol,
65oIt is stirred at reflux to clear under C, the mixture A is added dropwise, stirring is to being uniformly mixed, 65oReflux is kept the temperature under C
60min;It is subsequently cooled to 10o18h is placed in C, heat preservation, then rapid to filter, and removes inclusion compound;Filtrate rotary evaporation is removed into first
Then alcohol is added the water isometric with filtrate and is diluted, adds 3mol/L HCl/water solution and be acidified to system pH 4.0;With
N-hexane extraction, discards water layer, and rotary evaporation removes n-hexane, obtains mixture B;
C, mixture B obtained by step B is dissolved in acetone, the acetone quality is 8 times of mixture B mass, is slowly added to
Isobutyl hydramine, the addition of isobutyl hydramine are the 45% of mixture B mass, stir 3.0h, after complete formation to be precipitated, stand, take out
Filter, it is dry after washing 3 times with the ethyl alcohol of volume fraction 50%, obtain isodextropimaric acid ammonium salt crude product;By isodextropimaric acid ammonium salt crude product body
The ethanol water that fraction is 95% carries out 6 recrystallization purifications using compound recrystallization method, and it is brilliant to obtain isodextropimaric acid ammonium salt
Body;Will purifying isodextropimaric acid ammonium salt crystal input ether in, then be added 3mol/L HCl/waters solution to crystallize disappear, take second
Ether layer is washed with water to neutrality, and ether is evaporated off, and residue is dissolved in acetone, slowly drop add water to crystallization be not further added by until,
Then it filters, gained is crystallized into vacuum drying to get isodextropimaric acid, purity 98.3%.
Claims (1)
1. a kind of method for extracting high-purity isodextropimaric acid from five leaf pine-seed oils, it is characterised in that use following steps:
A, by the potassium hydroxide-ethanol solution of five leaf pine-seed oils and a concentration of 0.5 ~ 1.0 mol/L according to 1:3 ~ 7 volume ratio is mixed
It closes, 65 ~ 75oUnder C counterflow conditions, maintains stirring to oil droplet to disappear, obtain saponification liquor;The saponification liquor is cooled to room temperature, is taken out
It filters off and removes unsaponifiable matter, take clear filtrate to be concentrated, obtain concentrate, the HCl/water solution of a concentration of 6mol/L is added, adjust
The pH to 2-4 of the concentrate;The upper layer fluid of the concentrate, evaporative removal residual solvent is taken to obtain mixture A;
B, in mass ratio 1:3~8:6 ~ 12 weigh mixture A, urea and methanol obtained by step A respectively, by the urea and methanol
Mixing, 65oIt is stirred at reflux to clear under C, the mixture A is added dropwise, stirring is to being uniformly mixed, 65oIt is kept the temperature back under C
Flow 30 ~ 60min;It is subsequently cooled to -5 ~ 10o10 ~ 18h is placed in C, heat preservation, then rapid to filter, and removes inclusion compound;Filtrate is revolved
Turn methanol removed by evaporation, the water isometric with filtrate is then added and is diluted, the HCl/water for adding a concentration of 3mol/L is molten
Liquid is acidified to system pH 2 ~ 4;With n-hexane extraction, water layer is discarded, rotary evaporation removes n-hexane, obtains mixture B;
C, mixture B obtained by step B is dissolved in acetone, the acetone quality is 2 ~ 8 times of mixture B mass, is slowly added
Enter isobutyl hydramine, the addition of isobutyl hydramine is the 10 ~ 45% of mixture B mass, stirs 1 ~ 3h, quiet after complete formation to be precipitated
It sets, filters, it is dry after washing 3 times with the ethyl alcohol of volume fraction 50%, obtain isodextropimaric acid ammonium salt crude product;Isodextropimaric acid ammonium salt is thick
The ethanol water that product are 95% with volume fraction carries out 3 ~ 6 recrystallization purifications using compound recrystallization method, obtains isodextropimaric acid
Ammonium salt crystal;The isodextropimaric acid ammonium salt crystal of purifying is put into appropriate ether, the HCl/water of a concentration of 3mol/L is then added
Solution takes ether layer to be washed with water to neutrality, ether is evaporated off, residue is dissolved in proper amount of acetone, slowly drip to disappearance is crystallized
Add water to crystallization be not further added by until, then filter, by gained crystallize vacuum drying to get isodextropimaric acid.
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CN1696261A (en) * | 2005-06-25 | 2005-11-16 | 中国科学院新疆理化技术研究所 | Method for gathering jpolyunsaturated fatty acid and esterified matters oil through inclusion method of urea |
CN101302151A (en) * | 2008-06-06 | 2008-11-12 | 中国林业科学研究院林产化学工业研究所 | Preparation of isopimaric acid |
CN105175243A (en) * | 2015-07-15 | 2015-12-23 | 长春万成生物电子工程有限公司 | Method for purifying pinolenic acid from pine seed oil |
CN105925363A (en) * | 2016-04-17 | 2016-09-07 | 吉林派诺生物技术股份有限公司 | Extracting method of pine seed oil with low acid value and pinolenic acid |
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CN1696261A (en) * | 2005-06-25 | 2005-11-16 | 中国科学院新疆理化技术研究所 | Method for gathering jpolyunsaturated fatty acid and esterified matters oil through inclusion method of urea |
CN101302151A (en) * | 2008-06-06 | 2008-11-12 | 中国林业科学研究院林产化学工业研究所 | Preparation of isopimaric acid |
CN105175243A (en) * | 2015-07-15 | 2015-12-23 | 长春万成生物电子工程有限公司 | Method for purifying pinolenic acid from pine seed oil |
CN105925363A (en) * | 2016-04-17 | 2016-09-07 | 吉林派诺生物技术股份有限公司 | Extracting method of pine seed oil with low acid value and pinolenic acid |
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