CN101058776A - Method of removing erucic acid in grease obtained from descurainia sophia seed - Google Patents
Method of removing erucic acid in grease obtained from descurainia sophia seed Download PDFInfo
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- CN101058776A CN101058776A CN 200710109308 CN200710109308A CN101058776A CN 101058776 A CN101058776 A CN 101058776A CN 200710109308 CN200710109308 CN 200710109308 CN 200710109308 A CN200710109308 A CN 200710109308A CN 101058776 A CN101058776 A CN 101058776A
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Abstract
The invention discloses a removing method of erucic acid in the plant oil, which comprises the following steps: picking the seed of wormwood; removing impurity; dehydrating; squeezing; separating solid from liquid; obtaining the oil; adopting carbinol as solvent to do saponifying hydrolysis under alkaline condition; stewing; laminating; separating the composite fatty acid on the upper layer from the water layer on the lower layer; dissolving the composite fatty acid in the carbinol fitfully; placing the composition in the refrigerator until crystallizing and evolving; sucking in the vacuum; adding water in the filtrate to reextracte; obtaining the multiple unsaturated fatty acid with alpha-linolenic acid, linolic acid, arachidonic acid and less than 2% erucic acid.
Description
Technical field
The present invention relates to remove from vegetables oil the method for erucic acid, is from the plant descurainia sophia (l.) webb ex prantl exactly, particularly removes the method for erucic acid from the grease that descurainia sophia seed obtains.
Background technology
Descurainia sophia (l.) webb ex prantl is a Cruciferae Descurainia wild plant, and its formal name used at school is Descurainia Sophia (L.) Webb ex Prantl, in China loess plateau and Qinghai-Tibet Platean distribution is widely arranged, and its adaptability is very strong, and is cold-resistant, drought-enduring, and cattle and sheep do not eat.Chinese invention patent 99114958.0 is the greasy method of separating specific from the seed of descurainia sophia (l.) webb ex prantl plant openly.Its method is the descurainia sophia seed of gathering, obtain grease through solid-liquid separation process such as assorted clearly, dehydration, extruding or lixiviates, again grease is removed the gred, clarification and antioxidation treatment, promptly get and contain linolenic acid (N-3 series fatty acid) more than 40%, the grease of linolic acid (N-6 series fatty acid) more than 18%.This grease can directly offer the patient of urgent need, perhaps this grease is added in the relevant food, to replenish the deficiency of these endemic elements in people's meals.This patent has made full use of the high mountain wild plant resource, can provide high-quality health-nutrition product to the mankind simultaneously.
The oleaginousness of descurainia sophia seed and Semen Brassicae campestris, peanut are suitable, be about 35～44%, and based on unsaturated fatty acids, account for the 80%-90% of fatty acid total amount, wherein alpha-linolenic acid (α-Linolenic Acid, content C18:3) is the highest, can reach more than 30%, linolic acid (C18:2) is about 15%, but the content of erucic acid in the analysis revealed Semen Lepidii Semen Desurainiae oil is also higher relatively, is about 10～20%.
Erucic acid, its chemistry " suitable-13-22 carbon monoenoic acids " by name.Show that according to modern study erucic acid is relevant with the deposition of fat in the animal hearts tissue, easily causes vessel wall thickening, and then involves heart.Therefore, in edible oil product, the content of erucic acid is now added must be lower than 0.1% with restriction as developed country's edible vegetable oil standard-required content of erucic acid.It is contemplated that to have only and the content of erucic acid in the Semen Lepidii Semen Desurainiae oil is reduced or remove, descurainia sophia (l.) webb ex prantl just may become and obtains alpha-linolenic acid and linoleic plant resources.Main component is alpha-linolenic acid and linoleic polyunsaturated fatty acid in addition, its less stable, air effect with or uviolizing under oxidation can take place and go bad.
Summary of the invention
The invention provides and a kind ofly can overcome the prior art deficiency,, provide a kind of simultaneously and can make the oil product after removing erucic acid can stablize the method for storage to reduce the method for existing content of erucic acid in the Semen Lepidii Semen Desurainiae oil.
Method of the present invention is: the descurainia sophia seed of gathering, through clear assorted, dehydration, extruding and solid-liquid separation process obtain grease, then with grease under alkaline condition, with methyl alcohol is that solvent carries out the saponification hydrolysis, mixed fatty acid layer with the upper strata behind standing demix separates with the water layer of lower floor, mixed fatty acid is dissolved in (mixed fatty acid: methyl alcohol=1: 1～1: 3) in an amount of methyl alcohol, place refrigerator and cooled to freeze to there being crystallization to separate out, carry out vacuum filtration, gained filtrate adds the entry back extraction, obtains by alpha-linolenic acid, linolic acid, the polyunsaturated fatty acid of arachidonic acid and the erucic acid formation that is lower than total content 2%.
Handle in the product of gained through aforesaid method, add again and be dissolved with urea methanol, wherein urea quality is 1: 1～1: 2 with the ratio of methyl alcohol volume, the volume ratio of mixed fatty acid and urea methanol solution is 1: 5～1: 8, freezing after stirring, separate out until the adularescent crystal, filter out liquid, earlier the methyl alcohol in the filtrate is steamed, (filtrate: water=1: 1), with hydrochloric acid filtrate is adjusted to pH2-3, water and salt solution are washed till neutrality with filtrate to add less water again in filtrate, content of erucic acid will further reduce in the product that obtains like this, and actual detected shows that wherein the content of erucic acid will be lower than 0.5%.
To wrap up with beta-cyclodextrin with the resulting polyunsaturated fatty acid of preceding method and can improve its stability, both can be long time stored, also be more convenient for transportation and use.
Because the influence that the existence of erucic acid produces secondary face to direct use descurainia sophia (l.) webb ex prantl grease, thereby influence the deep development of descurainia sophia (l.) webb ex prantl, method of the present invention can effectively reduce, even remove fully and broadcast the erucic acid that exists in goddess's sagebrush oil fat, and other saturated fatty acid, particularly the present invention adopts solvent treatment and urea adduct method to remove erucic acid, erucic acid in the lipid acid of Semen Lepidii Semen Desurainiae oil can being formed is removed to and is lower than 0.5% level, therefore method of the present invention is paved the way for abundant linolenic and linoleic in the exploitation Semen Lepidii Semen Desurainiae oil, also can promote the exploitation of descurainia sophia (l.) webb ex prantl industry simultaneously.Because at drought mountain or high and cold deteriorate grassland; particularly at alpine steppe; because the influence of the soil erosion and livestock; after local thallophyta population was withered away gradually, becoming main dominant plant for it may will be descurainia sophia (l.) webb ex prantl, and the present invention can impel the plantation and the application of descurainia sophia (l.) webb ex prantl; form the descurainia sophia (l.) webb ex prantl industry; expection has positive meaning to developing western local economy, and person's character invention simultaneously can be played the desertification of containment soil, the effect of the ecotope of protection again indirectly.
Technological process of the present invention is all carried out under lesser temps and normal pressure, and whole process energy consumption is low, need not specific installation, and solvent for use methyl alcohol and inclusion agents urea is all recyclable recycles.The prepared polyunsaturated fatty acid of the present invention becomes micro-capsule through the beta-cyclodextrin parcel, has highly desirable stability and higher solubility property, can be used as the functional nutrient reinforcer, adds to easily in the numerous food, and its range of application is very wide.
Embodiment
Gather from the flixweed tansymustard seed (seed) of area, the sky and water, Gansu Province loess zone, get Semen Lepidii Semen Desurainiae oil by the mechanical expression legal system.The gained Semen Lepidii Semen Desurainiae oil is faint yellow, and density is 886kg/m
3Adopting the gas-chromatography tandem mass spectrum to analyze its greasy lipid acid forms.Used instrument is a gas chromatograph-mass spectrometer: U.S. Anjelen Sci. ﹠ Tech. Inc, 6890N-GC/5973N-MSD (this instrument is all used in following test among the present invention).Recording Semen Lepidii Semen Desurainiae oil lipid acid consists of:
Palmiticacid (5.57%), stearic acid (1.88%), linolic acid (14.63%), alpha-linolenic acid 42.75%), eicosanoic acid (2.14.%), arachidonic acid (15.05%), erucic acid (17.02.%) or the like.
Get descurainia sophia (l.) webb ex prantl grease 10ml, add methyl alcohol: 20ml and H
2Among the O:5ml, add NaOH (solid): 1.2g more therein.Agitation condition refluxes down, during temperature of reaction is controlled at 64-65 ℃, react and after 45 minutes reaction system be cooled to room temperature, reaction system is the gel homogeneous phase.Agitation condition adds 30% hydrochloric acid 10ml down, makes pH be about 1.Reaction system is placed the separating funnel standing demix, must arrive the upper strata and be the about 10ml of xanchromatic oil reservoir, lower floor is lurid water layer.Wash oil reservoir twice with water after separating oil reservoir, obtain mixed fatty acid.
Erucic acid is taken off in solvent treatment
The mixed fatty acid that aforementioned 10ml hydrolysis is made is dissolved in the 30ml methyl alcohol, places in-20 ℃ the refrigerator, has crystallization to separate out after the freezing night, vacuum filtration, and filtrate moves in the separating funnel, adds the entry back extraction and goes out mixed lipid acid.Sample is done the analysis of gas-chromatography tandem mass spectrum.Analytical results is:
Alpha-linolenic acid (69.12%), linolic acid (19.51%), arachidonic acid (8.46%), erucic acid is less than (1.17%).
Urea clathration takes off erucic acid
10g urea is joined in the 25ml methyl alcohol, be heated to 60 ℃ of dissolvings, dropwise add the mixed fatty acid of aforementioned 5ml after solvent treatment, be cooled to room temperature, forward-20 ℃ of refrigerator overnight to, the adularescent crystal is separated out.Filtrate moves to uses heating in water bath in the flask, steam methyl alcohol, steams to add 5ml water in the excess, is adjusted to pH2-3 with 10% hydrochloric acid, is transferred in the separating funnel, through hot water, have enough to eat and wear and salt solution is washed till neutrality, tells the about 4.5ml of fatty-acid layer.Product is done the analysis of gas-chromatography tandem mass spectrum.Analytical results is:
Alpha-linolenic acid (83.57%), linolic acid (16.43%), arachidonic acid: (0.00%), erucic acid: (0.00%), promptly except that alpha-linolenic acid and linolic acid, other saturated or monounsaturated fatty acids all is not detected.
The beta-cyclodextrin parcel
Get the 7g beta-cyclodextrin and be dissolved in 175mlH
2Among the O, stir and dropwise to add 1ml down and take off sample behind the erucic acid, under 50 ℃, control pH is 7-9, envelope 120min.Leave standstill 24h, vacuum filtration, filter cake slowly washs with dehydrated alcohol, then with filter cake after freezing 24h under-15--18 ℃, vacuum lyophilization gets final product.Gained beta-cyclodextrin micro-capsule is the light yellow solid powder, free from extraneous odour.Relevant infrared spectrum, and the absorbancy curve of oxidising process all can illustrate the generation of the Benexate Hydrochloride that takes off the erucic acid sample.
Product through the beta-cyclodextrin parcel can improve its stability, both can be long time stored, and also be more convenient for transportation and use can directly be added in relevant food.
Claims (3)
1, from descurainia sophia seed is grease obtained, remove the method for erucic acid, the descurainia sophia seed of gathering, through clear assorted, dehydration, extruding and solid-liquid separation process obtain grease, it is characterized in that grease under alkaline condition, with methyl alcohol is that solvent carries out the saponification hydrolysis, add an amount of acid neutralization, mixed fatty acid layer with the upper strata behind standing demix separates with the water layer of lower floor, mixed fatty acid is dissolved in the methyl alcohol, wherein the volume ratio of mixed fatty acid and methyl alcohol is 1: 1～1: 3, place refrigerator and cooled to freeze again to there being crystallization to separate out, carry out vacuum filtration, gained filtrate adds the entry back extraction, obtains by alpha-linolenic acid, linolic acid, the polyunsaturated fatty acid of arachidonic acid and the erucic acid formation that is lower than total content 2%.
2, the method for from descurainia sophia seed is grease obtained, removing erucic acid according to claim 1, it is characterized in that in resulting mixed fatty acid, adding and be dissolved with urea methanol, wherein urea quality is 1: 1～1: 2 with the ratio of methyl alcohol volume, and the volume ratio of mixed fatty acid and urea methanol solution is 1: 5～1: 8; Freezing after stirring, separate out until the adularescent crystal, filter out liquid, earlier the methyl alcohol in the filtrate is steamed, in filtrate, add isopyknic water again, filtrate is adjusted to pH2-3 with hydrochloric acid, water and salt solution are washed till neutrality with filtrate, and content of erucic acid is lower than 0.5% in the product that obtains.
3, the method for removing erucic acid from descurainia sophia seed is grease obtained according to claim 2 is characterized in that resulting mixed fatty acid is wrapped up with beta-cyclodextrin again.
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| Application Number | Priority Date | Filing Date | Title |
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| CN 200710109308 CN101058776B (en) | 2007-05-24 | 2007-05-24 | Method of removing erucic acid in grease obtained from descurainia sophia seed |
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| CN 200710109308 CN101058776B (en) | 2007-05-24 | 2007-05-24 | Method of removing erucic acid in grease obtained from descurainia sophia seed |
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| CN101058776A true CN101058776A (en) | 2007-10-24 |
| CN101058776B CN101058776B (en) | 2010-06-02 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105542968A (en) * | 2016-01-09 | 2016-05-04 | 北京化工大学 | Method for reducing content of erucic acid in radish seed oil |
| CN106947584A (en) * | 2017-04-21 | 2017-07-14 | 贵州省贵定县古镇香粮油有限公司 | A kind of processing method of rapeseed oil |
| CN112899063A (en) * | 2021-02-01 | 2021-06-04 | 太湖县野滋味食品商贸有限公司 | Processing method of rapeseed oil |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1013858B (en) * | 1988-03-26 | 1991-09-11 | 山东省海洋药物科学研究所 | Preparation of eicosapentaenoic acid (epa), docosahexenoic acid (dha) and their esters by separation |
| CN1091144C (en) * | 1999-06-25 | 2002-09-18 | 四川大学 | Method for separating specific oil from descurainia sophia seed |
| CN1095824C (en) * | 2000-04-13 | 2002-12-11 | 胡德甫 | Process for preparing high-purity alpha-linolenic acid |
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2007
- 2007-05-24 CN CN 200710109308 patent/CN101058776B/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105542968A (en) * | 2016-01-09 | 2016-05-04 | 北京化工大学 | Method for reducing content of erucic acid in radish seed oil |
| CN106947584A (en) * | 2017-04-21 | 2017-07-14 | 贵州省贵定县古镇香粮油有限公司 | A kind of processing method of rapeseed oil |
| CN112899063A (en) * | 2021-02-01 | 2021-06-04 | 太湖县野滋味食品商贸有限公司 | Processing method of rapeseed oil |
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| CN101058776B (en) | 2010-06-02 |
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Granted publication date: 20100602 Termination date: 20110524 |