CN1696261A - Method for gathering jpolyunsaturated fatty acid and esterified matters oil through inclusion method of urea - Google Patents
Method for gathering jpolyunsaturated fatty acid and esterified matters oil through inclusion method of urea Download PDFInfo
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- CN1696261A CN1696261A CN 200510081504 CN200510081504A CN1696261A CN 1696261 A CN1696261 A CN 1696261A CN 200510081504 CN200510081504 CN 200510081504 CN 200510081504 A CN200510081504 A CN 200510081504A CN 1696261 A CN1696261 A CN 1696261A
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Abstract
A process for enriching the polyunsaturated fatty acid contained in Heijialun seed and its esterified substance by urea encapsulation method includes mixing the mixed fatty acid an its esterified substance with solvent system while adding urea, stirring to form the encapsulated substance of urea, freezing, filtering or centrifugal separation to obtain solvent phase, distilling to remove solvent, and distilling to obtain the polyunsaturated fatty acid or its esterified substance.
Description
Technical field
The present invention relates to a kind of under solvent system, with the method for many saturated fatty acids and carboxylate thereof in the urea inclusion method enrichment seed of black currant oil.
Background technology
Black currant (Ribes negrum L.), formal name used at school black-current (black currant), the fruit for Saxifragaceae (Saxifvage) tea foot of a hill or mountain son genus (Ribes) plant belongs to perennial undershrub, is a kind of wild plant of spreading all over frigid zone and temperate zone.Seed of black currant is the vegetables oil that is rich in polyunsaturated fatty acid, oleaginousness 17% (this real estate), and wherein linolic acid is (18: 2
Δ 9.7.2) over half approximately, r-linolenic acid (18: 3
Δ 6.9.12) content is 11.71%, a-linolenic acid (18: 3
Δ 9.12.15) content is 14.75%, and a spot of 18 carbon, four diluted acids.Be the vegetables oil that is rich in polyunsaturated fatty acid, (Zhou Qingfeng, Chinese oil, 1996, (5): 20-22).
Its physiological function: a-linolenic acid:
1, be to keep the brain and the necessary factor of neural system, human body lacks the a-linolenic acid, and then unusual obstacle will take place neural system such as brain, retina, therefore, and the a-linolenic acid neural system indispensable fatty acid that is otherwise known as;
2, have antithrombotic and lipid-lowering effect;
3, can prevent canceration and inhibition tumour cancer metastasis;
4, suppress the pathosis illness;
5, long-term eating can prolong the lifetime.
The r-linolenic acid:
1, have and significantly fall blood ester, hypotensive activity, its reducing blood lipid is more remarkable than linolic acid;
2, anti-inflammatory antiinflammation can prevent and treat allergic dermatitis;
3, has the effect that significantly weakens peroxide injury;
4, prevention senile dementia;
5, be used for the dry-out phenomenon that makeup then can improve skin, produce lubricated comfortable effect;
6, the premenstrua syndromes there is certain curative effect.
Medically the r-linolenic acid is mainly used in treatment heart trouble, vascular disorder, hypertension, diabetes, obesity, premenstrua syndromes and optimum galactophore disease.(western science and technology of grain and oil, 25 (6), 2000).Polyunsaturated fatty acid (polyenoic acid) is an essential fatty acid, it can not synthesize in vivo, must be by food supply, health to human body plays crucial effect, polyenoic acid is meant the lipid acid that contains two or more unsaturated link(age)s in the molecular structure, two keys multi-section saturation ratio more are high more, also high more (the China's health care newspaper of nutritive value, 1995 (5): 52, Wang Mingli), most of vegetables oil all contain the acid of linolic acid and alpha-oil fiber crops, and the plant that contains γ-spunyarn acid seldom, and the medicinal and pharmacy aspect of γ-spunyarn acid is paid close attention to by people.(US?patent?4703060，1987；US?patent?4466926，1984)。One times of γ in the content of γ in the seed of black currant oil-spunyarn acid and the root of Redsepal Eveningprimrose-spunyarn acid content.To be raw material obtain the polyunsaturated fatty acid that content is 80%-95% with the method for urea inclusion through developing with the seed of black currant oil after a large amount of experimental study in the present invention.
Polyunsaturated fatty acid is paid attention to by people the physiological function of human body is just more and more in the natural fats and oils, as linolic acid is the lipid acid of needed by human, it is histiocytic moiety, the growth of synthetic, the human body cambium of phosphine fat, the synthetic of the reparation of damaged tissue, prostaglandin(PG) all must have linoleic existence.Alpha-linolenic acid and gamma-linolenic acid are two kinds of high unsaturated fatty acids that human body is had important physiological function, and especially the control to cardiovascular and cerebrovascular diseases has special curative effect.EPA (timnodonic acid) and DHA (docosahexenoic acid) have antithrombotic, anti-inflammatory, anticancer disease and promotion brain development, functions such as hypermnesis, and natural polyunsaturated fatty acid all is contained in the different animal-plant oil, as: linseed oil, all kinds of fish oil, Thistle oil, Oenothera oil, juniper berry oil, soybean oil, Trisun Oil R 80, Oleum Gossypii semen, perilla oil, seed of black currant oil, Oleum Hippophae, raisin seed oil, synourin oil, Chinese catalpa oil, paddy oil, peanut oil, Semen Maydis oil, mouse melon seeds oil, common seepweed seeds oil, horse fat etc., these greasy fatty acid components are complicated, it is the mixture of multiple lipid acid, and the existence of saturated fatty acid often influences tiring of polyunsaturated fatty acid physiological function, will have the alpha-linolenic acid of physiological function, gamma linolenic acid, linolic acid, EPA, it is an important technology that DHA enrichment from mixed fatty acid is come out.
At present, the technology of separation and purification polyunsaturated fatty acid mainly contains: 1, low temperature crystallization method of purification; 2, urea adduct method; 3, molecular distillation method; 4, adsorption method of separation; 5, supercritical fluid extraction; 6, utilize the specificity of lipase to carry out purifying.
Luthria etc. (US Patent 6395778) utilize the polyunsaturated fatty acid methyl esters in the urea inclusion method enrichment mixed methyl aliphatic ester: 50 gram fatty acid methyl esters are joined in the 500ml methanol solution, add 100 gram urea then, heat, be stirred to all urea dissolvings, cold crystallization, centrifugation, steaming desolventize methyl alcohol then, obtain the thick product of 23 grams.
People such as Lee (US Patent 6664405) join 1.5kg urea in the 4L methyl alcohol, heating, stirring, treat to dissolve fully the back and add the lipid acid 1Kg that contains linolic acid 75%, the freezing crystalline substance of forming an association, filtration or centrifugation obtain the methyl alcohol phase of polyunsaturated acid, desolventize through steaming again, obtain thick product.
People ([P] .CN1162009A, 1997) such as the Xia Zongjian of Beijing WanFuTe Trade Company, Guan Yong have studied the separation and Extraction of alpha-linolenic acid in the oleum lini.Just can make the total yield of polyvalent unsaturated fatty acid reach 60.4% with a urea adduct method, accumulation rate reaches more than 95%, and the content of alpha-linolenic acid brings up to 72.8% from 53.8%, and each composition after the separation also can fully utilize.
(Transactions of the Chinese Society of Agricultural Engineering such as Li Guowen, 1997,13 (1): 198-201) with the fish oil ethyl ester be raw material, itself and saturated urea-ethanolic soln are carried out inclusion, with the increase of urea and fish oil ethyl ester mol ratio or the reduction of Tc, EPA and DHA content have been obtained at the goods more than 70%.
The method that the present invention relates to is a urea adduct method.Urea adduct method is to be the axle center with a straight chain fatty compounds, can be between the urea molecule by powerful hydrogen bond force around this root axle with the right hand rising of spiraling, with this root axle always around the fatty acid group compound tightly inclusion live, thereby form six prisms, unit of six urea molecule formation promptly finishes and spirals in a week, urea molecule can form more stable crystal inclusion compound with saturated fatty acid or single unsaturated fatty acids and separate out in crystallisation process, and polyunsaturated fatty acid is because two key is more, the carbochain bending has certain sterie configuration.Be difficult for by urea clathration, adopt centrifugal method to remove the inclusion compound that saturated fatty acid and single unsaturated fatty acids and urea form, just can obtain the polyunsaturated fatty acid of higher degree.
To be raw material obtain the polyunsaturated fatty acid that content is 80%-95% with the method for urea inclusion through developing with the seed of black currant oil after a large amount of experimental study in the present invention.The present invention adopts the urea inclusion method under the solvent system, cold crystallization, and the solvent recuperation energy consumption reduces, and has improved production efficiency.Make that unsaturated fatty acid content reaches more than 80% in the Hei Jialun seed oil.Technology cleaning of the present invention, environmental friendliness, free from environmental pollution, implementation condition is simple, is convenient to carry out large-scale production.
Summary of the invention
The objective of the invention is method with urea inclusion method enriching polyunsaturated fatty acid and carboxylate thereof, this method is mixed mixed fatty acid or its carboxylate with solvent system, add urea simultaneously, the abundant contact of realization system, form the inclusion complex of urea mutually in short chain alcohol, through freezing, then whole system is obtained solvent phase through filtration or centrifugation, solvent phase is obtained by the polyunsaturated fatty acid of enrichment or its carboxylate through steaming to desolventize with distilled fatty acid or its carboxylate, the technology of whole enriching polyunsaturated fatty acid or its carboxylate has obtained very big simplification again.This method is free from environmental pollution, the technology cleaning, and environmental friendliness is convenient to large-scale production.
Method with polyunsaturated fatty acid and carboxylate thereof in the urea inclusion method enrichment seed of black currant oil of the present invention, be with mixed fatty acid in the seed of black currant oil or fatty acid esterification thing, join in the solvent system, add urea simultaneously, temperature is controlled at 20-80 ℃, stirred then 1-24 hour, then after filtration or centrifugation, obtain solvent phase, remove through distillation again and desolvate, distillation obtains by enriching polyunsaturated fatty acid or fatty acid esterification thing, and its content is 80%-95%, wherein mixed fatty acid or its carboxylate, urea, the weight ratio of solvent is: 100: 100-500: 500-1000.
Solvent is the short chain alcohol of methyl alcohol or ethanol or propyl alcohol or butanols.
The mixed fatty acid or its carboxylate of this method in being applicable to seed of black currant oil, also be applicable to linseed oil or all kinds of fish oil or Thistle oil or Oenothera oil or juniper berry oil or soybean oil or Trisun Oil R 80 or Oleum Gossypii semen or perilla oil or Oleum Hippophae or raisin seed oil or synourin oil or Chinese catalpa oil or paddy oil or peanut oil or Semen Maydis oil or mouse melon seeds oil or common seepweed seeds oil or horse fat deutero-mixed fatty acid or its carboxylate, its carboxylate is mainly fatty acid methyl ester, fatty-acid ethyl ester and lipid acid propyl ester.
Method with polyunsaturated fatty acid and carboxylate thereof in the urea inclusion method enrichment seed of black currant oil of the present invention, have following characteristics: urea inclusion method enrichment lipid acid or its carboxylate under (1) solvent system, urea fully is dissolved in the short-chain alcohols solvent, content of polyunsaturated fatty acid height in the seed of black currant oil that obtains, solvent recuperation can reduce production costs; (2) this law alr mode is that general alr mode is by mechanical stirring 1-24; Improve plant factor.(3) this method crystallization urea inclusion complex under freezing conditions.Tradition urea saturation method is a kind of free from environmental pollution, the technology cleaning, and environmental friendliness is convenient to the method for large-scale production.
Embodiment
The present invention will be further described below by embodiment.
Embodiment 1
Double centner seed of black currant oil ethyl ester, double centner urea, 500 kilograms of ethanol are added in the reactor and mix, in 20 ℃ of following mechanical stirring 2 hours, placed 12 hours for-10 ℃, take out material centrifugal (filtration) then, remove the urea inclusion that saturated fatty acid and monounsaturated fatty acids and urea form, steaming desolventizes, and promptly gets 52 kilograms of higher degree polyunsaturated fatty acids.
Embodiment 2
Double centner seed of black currant oil, 200 kilograms of part urea, 1000 kilograms of methyl alcohol are added in the reactor and mix, in 40 ℃ of mechanical stirring 10 hours, placed 10 hours for 1 ℃, take out material centrifugal (filtration) then, remove the urea inclusion that saturated fatty acid and monounsaturated fatty acids and urea form, collect solvent and separate in separator, steaming desolventizes, and promptly gets 49 kilograms of higher degree polyunsaturated fatty acids.
Embodiment 3
Double centner seed of black currant oil methyl esters, 300 kilograms of part urea, 700 kilograms of propyl alcohol are added in the reactor and mix, in 80 ℃ of following mechanical stirring 24 hours, placed 12 hours for-8 ℃, take out material centrifugal (filtration) then, remove the urea inclusion that saturated fatty acid and monounsaturated fatty acids and urea form, collect solvent and separate in separator, steaming desolventizes, and promptly gets 80 kilograms of higher degree polyunsaturated fatty acids.
Embodiment 4
Double centner seed of black currant oil ethyl ester, 500 kilograms of part urea, 800 kilograms of butanols are added in the reactor and mix, 60 ℃ were stirred 12 hours, cooled off then 12 hours, take out material centrifugal (filtration), remove the urea inclusion that saturated fatty acid and monounsaturated fatty acids and urea form, collect solvent and separate in separator, steaming desolventizes, and promptly gets 44 kilograms of higher degree polyunsaturated fatty acids.
Embodiment 5
Double centner linseed oil methyl esters, 200 kilograms of part urea, 550 kilograms of propyl alcohol are added in the reactor and mix, in 80 ℃ of following mechanical stirring 24 hours, placed 12 hours for-5 ℃, take out material centrifugal (filtration) then, remove the urea inclusion that saturated fatty acid and monounsaturated fatty acids and urea form, collect solvent and separate in separator, steaming desolventizes, and promptly gets 60 kilograms of higher degree polyunsaturated fatty acids.
Embodiment 6
Double centner Thistle oil ethyl ester, double centner part urea, 500 kilograms of ethanol are added in the reactor and mix, in 60 ℃ of following mechanical stirring 20 hours, placed 11 hours for-7 ℃, take out material centrifugal (filtration) then, remove the urea inclusion that saturated fatty acid and monounsaturated fatty acids and urea form, collect solvent and separate in separator, steaming desolventizes, and promptly gets 58 kilograms of higher degree polyunsaturated fatty acids.
Embodiment 7
Double centner synourin oil, 500 kilograms of part urea, 900 kilograms of methyl alcohol are added in the reactor and mix, in 50 ℃ of following mechanical stirring 15 hours, placed 10 hours for-4 ℃, take out material centrifugal (filtration) then, remove the urea inclusion that saturated fatty acid and monounsaturated fatty acids and urea form, collect solvent and separate in separator, steaming desolventizes, and promptly gets 70 kilograms of higher degree polyunsaturated fatty acids.
Embodiment 8
Double centner peanut oil methyl esters, 300 kilograms of part urea, 600 kilograms of propyl alcohol are added in the reactor and mix, in 40 ℃ of following mechanical stirring 10 hours, placed 12 hours for-9 ℃, take out material centrifugal (filtration) then, remove the urea inclusion that saturated fatty acid and monounsaturated fatty acids and urea form, collect solvent and separate in separator, steaming desolventizes, and promptly gets 65 kilograms of higher degree polyunsaturated fatty acids.
Embodiment 9
Double centner Oleum Hippophae propyl ester, 300 kilograms of part urea, 1000 kilograms of ethanol are added in the reactor and mix, in 80 ℃ of following mechanical stirring 24 hours, placed 11 hours for 1 ℃, take out material centrifugal (filtration) then, remove the urea inclusion that saturated fatty acid and monounsaturated fatty acids and urea form, collect solvent and separate in separator, steaming desolventizes, and promptly gets 80 kilograms of higher degree polyunsaturated fatty acids.
Embodiment 10
Double centner common seepweed seeds oil methyl esters, 200 kilograms of part urea, 500 kilograms of butanols are added in the reactor and mix, in 30 ℃ of following mechanical stirring 5 hours, placed 12 hours for-10 ℃, take out material centrifugal (filtration) then, remove the urea inclusion that saturated fatty acid and monounsaturated fatty acids and urea form, collect solvent and separate in separator, steaming desolventizes, and promptly gets 78 kilograms of higher degree polyunsaturated fatty acids.
Claims (3)
1, a kind of method with polyunsaturated fatty acid and carboxylate thereof in the urea inclusion method enrichment seed of black currant oil, it is characterized in that mixed fatty acid in the seed of black currant oil or fatty acid esterification thing, join in the solvent system, add urea simultaneously, temperature is controlled at 20-80 ℃, stirred then 1-24 hour, placed 10-12 hour for-10 ℃-1 ℃, then after filtration or centrifugation, remove urea inclusion, obtain solvent phase, remove through distillation again and desolvate, distillation obtains by enriching polyunsaturated fatty acid or fatty acid esterification thing, and its content is 80%-95%, wherein mixed fatty acid or its carboxylate, urea, the weight ratio of solvent is: 100: 100-500: 500-1000.
2, the method with polyunsaturated fatty acid and carboxylate thereof in the urea inclusion method enrichment seed of black currant oil according to claim 1 is characterized in that solvent is the short chain alcohol of methyl alcohol or ethanol or propyl alcohol or butanols.
3, a kind of method according to claim 1 with polyunsaturated fatty acid and carboxylate thereof in the urea inclusion enrichment seed of black currant oil, it is characterized in that the mixed fatty acid or its carboxylate of this method in being applicable to seed of black currant oil, also be applicable to linseed oil or all kinds of fish oil or Thistle oil or Oenothera oil or juniper berry oil or soybean oil or Trisun Oil R 80 or Oleum Gossypii semen or perilla oil or Oleum Hippophae or raisin seed oil or synourin oil or Chinese catalpa oil or paddy oil or peanut oil or Semen Maydis oil or mouse melon seeds oil or common seepweed seeds oil or horse fat deutero-mixed fatty acid or its carboxylate, its carboxylate is mainly fatty acid methyl ester, fatty-acid ethyl ester and lipid acid propyl ester.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101353612B (en) * | 2008-08-22 | 2010-11-17 | 中南林业科技大学 | Method for enriching polyunsaturated fatty acid from pine caterpillar |
| CN101942357A (en) * | 2010-09-10 | 2011-01-12 | 中国林业科学研究院林产化学工业研究所 | Method for isolating jatropha curcas oil polyunsaturated fatty acids |
| CN101658211B (en) * | 2009-09-15 | 2012-05-23 | 中国农业科学院油料作物研究所 | Extracting debitterizing method of edible linseed oil |
| CN101472483B (en) * | 2006-06-22 | 2013-01-30 | E.S.生物技术有限公司 | Edible plant oils from which saturated fatty acids were removed and manufacturing process thereof |
| CN108715577A (en) * | 2018-05-09 | 2018-10-30 | 珀莱雅化妆品股份有限公司 | A method of extracting high-purity isodextropimaric acid from pine-seed oil |
| CN109943414A (en) * | 2017-11-30 | 2019-06-28 | 株式会社伊迈克斯解决方案 | Use urea water dropping liquid crystallization method, the high-purity unsaturated fatty acid methyl ester that gives up using high-acid value grease resource manufacturing method |
-
2005
- 2005-06-25 CN CN 200510081504 patent/CN1696261A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101472483B (en) * | 2006-06-22 | 2013-01-30 | E.S.生物技术有限公司 | Edible plant oils from which saturated fatty acids were removed and manufacturing process thereof |
| CN101353612B (en) * | 2008-08-22 | 2010-11-17 | 中南林业科技大学 | Method for enriching polyunsaturated fatty acid from pine caterpillar |
| CN101658211B (en) * | 2009-09-15 | 2012-05-23 | 中国农业科学院油料作物研究所 | Extracting debitterizing method of edible linseed oil |
| CN101942357A (en) * | 2010-09-10 | 2011-01-12 | 中国林业科学研究院林产化学工业研究所 | Method for isolating jatropha curcas oil polyunsaturated fatty acids |
| CN101942357B (en) * | 2010-09-10 | 2013-08-14 | 中国林业科学研究院林产化学工业研究所 | Method for isolating jatropha curcas oil polyunsaturated fatty acids |
| CN109943414A (en) * | 2017-11-30 | 2019-06-28 | 株式会社伊迈克斯解决方案 | Use urea water dropping liquid crystallization method, the high-purity unsaturated fatty acid methyl ester that gives up using high-acid value grease resource manufacturing method |
| CN108715577A (en) * | 2018-05-09 | 2018-10-30 | 珀莱雅化妆品股份有限公司 | A method of extracting high-purity isodextropimaric acid from pine-seed oil |
| CN108715577B (en) * | 2018-05-09 | 2020-12-01 | 珀莱雅化妆品股份有限公司 | Method for extracting high-purity isopimaric acid from pine seed oil |
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