CN101486647B - Method for extracting nervonate from nervonate and eruciate mixer - Google Patents
Method for extracting nervonate from nervonate and eruciate mixer Download PDFInfo
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- CN101486647B CN101486647B CN2009100737750A CN200910073775A CN101486647B CN 101486647 B CN101486647 B CN 101486647B CN 2009100737750 A CN2009100737750 A CN 2009100737750A CN 200910073775 A CN200910073775 A CN 200910073775A CN 101486647 B CN101486647 B CN 101486647B
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Abstract
The invention relates to a method for extracting pure nervonic acid ester from a mixture of nervonic acid ester and erucate, the method comprises the steps that: in the mixture rich in nervonic acid methyl ester and erucic acid methyl ester or the mixture rich in nervonic acid ethyl ester and erucic acid ethyl ester, low-carbon alcohols are added to the mixture according to the proportion of the mixture and the low-carbon alcohols between 1g to 50ml and 20g to 50ml; urea is added according to the mass ratio of the mixture and the urea between 1 to 7 and 3 to 7; stirring is carried out at temperature between 60 DEG C and 80 DEG C until the solution gets transparent; clathration is carried out for 5h to 24h at temperature of 20 DEG C to 50 DEG C, thus obtaining urea clathrate which goes through sucking filtration or separation by filtering; the crystal of the urea clathrate is taken and dissolved in distilled water, goes through extraction with petroleum ether and stands for layering; the organic phase at the upper layer is taken and goes through decompressing evaporation at temperature of 40 DEG C to 60 DEG C; the petroleum ether is recycled by the condensation of the gas phase;and the liquid phase obtained is the product. The method has the advantages of low cost, simple technique, being suitable for operation and producing the nervonic acid with high purity.
Description
Technical field
The invention belongs to the purification of fatty ester, be specifically related to a kind of method of the neural acid esters of from neural acid esters and eruciate mixer, purifying.
Technical background
Selacholeic acid has another name called shark acid, is suitable-15-tetracosenoic acid, and pure article are the white needles solid at normal temperatures, is a kind of n-9 type long-chain monoenoic fatty acid, is found in mammiferous nervous tissue the earliest, so the called after Selacholeic acid.Selacholeic acid is a biomembranous important composition composition in the nervous tissue; It is the significant composition of medullary substance in the brain glucoside; Be the core natural component of cerebral nerve fiber and neurocyte, be particularly brain cell, optic cell, peripheral nerve growth of neurocyte, again grow and the essential high-grade nutrient kept plain.Selacholeic acid not only is suitable for the nutritive health-care of the daily brain of healthy subjects, is particularly suitable for pregnant woman, infant, old man, mental worker, cerebral disorders and brain damage, optic nerve nutrition, the sight protectio crowd takes.In addition, Selacholeic acid can be repaired, reduce to wear out and undermined hardened cardiovascular and cerebrovascular wall, upgrades vascular wall tissue; Recover the blood vessel elasticity vigor; Have obvious reduce fat, reduce blood viscosity, suppress hematoblastic cohesive force and inflammatory factor; High density lipoprotein increasing, and special efficacy is arranged to treating some tetter.Selacholeic acid also is a kind of crucial fine chemical material simultaneously, but be raw material synthetic musk ketone, encircles ten five-carbon ketones, 15 carbon lactones, sex pheromone of Ostrinia furnacalis, housefly sex pheromone etc. with it.Along with to the continuous development of Selacholeic acid medical mechanism, functional study and the raising of suitability for industrialized production level, Selacholeic acid is widely used in medicine, healthcare products, functional food and makeup, and therefore separating the purification Selacholeic acid has high practical value.
Horse Berlin etc. contains the Selacholeic acid plant to China and has carried out system retrieves, and finding has 31 kinds of plants that contain Selacholeic acid, defines utility value, Selacholeic acid massfraction 10 kinds of the xylophytas more than 2%; Herbage 5 kinds of [horse Berlin etc., northwest Botany Gazette, 2004; 24 (12), 2362].Though China contains the Selacholeic acid floristics seldom, development potentiality is very big, and malania oleifera is the hat that contains the Selacholeic acid plant, and scute Macaranga and Acer etc. contains the woody seeds of Selacholeic acid, and the artificial afforestation area increases comparatively fast in recent years, and the cultivation of follow-up resource development rapidly.The Acer that with the acer truncatum is representative contains the Selacholeic acid seeds, though Selacholeic acid content is low than malania oleifera, the solid amount of Acer seeds is big, plants the benevolence oil length near 50%.5 kinds of herbage stock numbers that contain Selacholeic acid are big, remain to be developed.Pan Jianguo etc. have found Selacholeic acid first in several kinds of pollen, its massfraction is [Pan Jianguo etc., analytical test journal, 2003,22 (1), 74] about 3%.Internationally recognized Selacholeic acid will be the most promising encephalopathic sanitary prods of 21 century, undoubtedly, contain the Selacholeic acid plant acquisition is developed rapidly.
But owing to except Selacholeic acid, also contain various lipid acid such as a large amount of oleic acid, eicosenoic acid, erucic acid in these plant material oil, their structures are close, and similar performance is not easy to separate.Especially erucic acid is suitable-13-Decosahedaenoic acid, also is n-9 type long-chain monoenoic fatty acid, therefore from raw oil, extracts the high Selacholeic acid health-care medical product of content, has become the technical bottleneck of restriction Selacholeic acid product application.
At present, domestic from vegetables oil the method for extraction separation Selacholeic acid metal salt precipitate method, emulsification partition method, soap column chromatography, solvent crystallization and molecular distillation method etc. are arranged.Wherein, the metal salt precipitate method is the separation [Hou Jingde etc., the metal salt precipitate method is separated Selacholeic acid, biotechnology, 1996,6 (1), 39] that the raw material more than 70% carries out to Selacholeic acid content; The emulsification partition method is a raw material with oil fruit oil; In thick Selacholeic acid, add emulsifying agent X 2073, ionogen sal epsom or sodium-chlor, water; Controlled temperature is 45～50 ℃, high speed centrifugation separation then, crystallization, the dry Selacholeic acid product that gets, and this method also has higher requirements to raw material Selacholeic acid content; Operations such as spinning are difficult under 45～50 ℃ all realizing that emulsifying agent and ionogen reclaim relatively difficulty [number of patent application: 02136802.3]; Solvent crystallization is that about 50% malania oleifera oil separates to Selacholeic acid content, and Tc is-10～-8 ℃, this method raw material Selacholeic acid content height and the higher [Huang Pinxian etc. of low ternperature separation process cost; Organic solvent extraction separates the research of malania oleifera oil, Guangxi chemical industry, 1998; 27 (3), 1]; Xu Wenhui has carried out initial gross separation with urea adduct method to the Acertruncatum Bunge oil fatty acid methyl ester, and Selacholeic acid content has reached 17% from 5% behind twice inclusion, and the inclusion temperature is-10 ℃ of [Xu Wenhui etc.; The initial gross separation of Selacholeic acid in the Acertruncatum Bunge oil, Chinese oil, 2007; 32 (11), 49].The firm grade in Korean discloses a kind of method of from Acertruncatum Bunge oil, extracting Selacholeic acid; Its operational path comprises saponification and urea low temperature embedding process, normal temperature vacuum distillation process, freezing fractional crystallization process, methyl esterification of fatty acid and sepn process, the weak adsorption and purification process of selectivity; Adopt the column chromatography elution step more; Solvent-oil ratio is big, has problems [number of patent application: 200510096369.8] such as route is complicated, the easy emulsification of washing; Luo Yongzhu etc. disclose the method [number of patent application: 200710018195.2] of from Acertruncatum Bunge oil, extracting the Selacholeic acid ethyl ester with molecular distillation technique, but exist short-path distillation progression many, and distillation temperature is high, and the Selacholeic acid purity that makes has only problem such as 50%.
Summary of the invention:
The object of the present invention is to provide a kind of method of the neural acid esters of from neural acid esters and eruciate mixer, purifying, the cost of this method is low, and technology is simple, suitable operation, and product Selacholeic acid purity is high.
In order to achieve the above object, method of purification of the present invention comprises the steps:
(1) be rich in Selacholeic acid methyl esters and methyl erucate mixture or be rich in the Selacholeic acid ethyl ester and the ethyl erucate mixture in; Ratio in mixture and low-carbon alcohol is that 1g: 20～50ml adds low-carbon alcohol; Mass ratio by mixture and urea is 1: 3～7 adding urea again; 60～80 ℃ be stirred to the solution clear after, at 20～50 ℃ of inclusion 5～24h, obtain urea inclusion;
(2) gained urea inclusion suction filtration or filtering separation get urea inclusion crystallising part and filtrating part;
(3) get the urea inclusion crystallising part, be dissolved in zero(ppm) water, use petroleum ether extraction, standing demix is got upper organic phase, reduction vaporization under 40～60 ℃ of temperature, and vapor condensation reclaims sherwood oil, and liquid phase promptly gets the sample of purifying;
(4) the purification sample is repeated above-mentioned (1)～(3) step, obtain Selacholeic acid methyl esters or Selacholeic acid ethyl ester.Be rich in that the mol ratio of Selacholeic acid methyl esters and methyl erucate is 1: 0.5～5 in Selacholeic acid methyl esters and the methyl erucate mixture described in the above-mentioned steps (1).
Be rich in that the mol ratio of Selacholeic acid ethyl ester and ethyl erucate is 1: 0.5～5 in Selacholeic acid ethyl ester and the ethyl erucate mixture described in the above-mentioned steps (1).
Low-carbon alcohol described in the above-mentioned steps (1) is methyl alcohol, ethanol or propyl alcohol.
Compared with prior art, advantage of the present invention is following:
1, adaptability to raw material is wide;
2, service temperature is moderate, and method is simple, has reduced running cost, is convenient to industrialization;
3, separation can obtain Selacholeic acid methyl esters or Selacholeic acid ethyl ester content Different products; Selacholeic acid methyl esters or Selacholeic acid ethyl ester highest purity can reach 90%; Can reclaiming of low Selacholeic acid methyl esters or Selacholeic acid ethyl ester content separates purification again; Also can improve efficiency of resource to different purposes as production marketing;
4, the solvent and the urea of urea adduct method use all can be recycled, and both can reduce cost, and also reduce environmental pollution.
Specific embodiment 1:
(1) gets the mixture of 1g Selacholeic acid ethyl ester and ethyl erucate; Wherein Selacholeic acid content is 46%, and Selacholeic acid ethyl ester and ethyl erucate mol ratio are 1: 1, adds 20ml methyl alcohol and 3g urea; After being stirred to the solution clear in 80 ℃ of water-baths, at 20 ℃ of following inclusion 5h.
(2) gained urea inclusion crystallization suction filtration separates, and gets urea inclusion crystallising part and filtrating part;
(3) get the urea inclusion crystallising part, be dissolved in zero(ppm) water, use petroleum ether extraction, standing demix is got upper organic phase, reduction vaporization in 40 ℃ of water-baths, and vapor condensation reclaims sherwood oil, and liquid phase promptly gets the sample of purifying;
(4) the purification sample is repeated 5 above-mentioned steps (1)～(3), obtain Selacholeic acid ethyl ester content and be 91% product.
Specific embodiment 2:
(1) gets the mixture of 1g Selacholeic acid ethyl ester and ethyl erucate; Wherein Selacholeic acid content is 40%, and Selacholeic acid ethyl ester and ethyl erucate mol ratio are 1: 1.3, adds 25ml ethanol and 4g urea; After being stirred to the solution clear in 70 ℃ of water-baths, at 30 ℃ of following inclusion 8h.
(2) gained urea inclusion crystallization filtering separation gets urea inclusion crystallising part and filtrating part;
(3) get the urea inclusion crystallising part, be dissolved in zero(ppm) water, use petroleum ether extraction, standing demix is got upper organic phase, reduction vaporization in 50 ℃ of water-baths, and vapor condensation reclaims sherwood oil, and liquid phase promptly gets the sample of purifying;
(4) the purification sample is repeated 5 above-mentioned steps (1)～(3), obtain Selacholeic acid ethyl ester content and be 91% product.
Specific embodiment 3:
(1) gets the mixture of 1g Selacholeic acid ethyl ester and ethyl erucate; Wherein Selacholeic acid content is 45%, and Selacholeic acid ethyl ester and ethyl erucate mol ratio are 1: 1, adds 28ml methyl alcohol and 5g urea; After being stirred to the solution clear in 70 ℃ of water-baths, at 35 ℃ of following inclusion 12h.
(2) gained urea inclusion crystallization suction filtration separates, and gets urea inclusion crystallising part and filtrating part;
(3) get the urea inclusion crystallising part, be dissolved in zero(ppm) water, use petroleum ether extraction, standing demix is got upper organic phase, reduction vaporization in 50 ℃ of water-baths, and vapor condensation reclaims sherwood oil, and liquid phase promptly gets the sample of purifying;
(4) the purification sample is repeated 4 above-mentioned steps (1)～(3), obtain Selacholeic acid ethyl ester content and be 90.5% product.
Specific embodiment 4:
(1) gets the mixture of 1g Selacholeic acid ethyl ester and ethyl erucate; Wherein Selacholeic acid content is 36.5%, and Selacholeic acid ethyl ester and ethyl erucate mol ratio are 1: 1.5, adds 40ml methyl alcohol and 6g urea; After being stirred to the solution clear in 70 ℃ of water-baths, at 40 ℃ of following inclusion 18h.
(2) gained urea inclusion crystallization filtering separation gets urea inclusion crystallising part and filtrating part;
(3) get the urea inclusion crystallising part, be dissolved in zero(ppm) water, use petroleum ether extraction, standing demix is got upper organic phase, reduction vaporization in 50 ℃ of water-baths, and vapor condensation reclaims sherwood oil, and liquid phase promptly gets the sample of purifying;
(4) the purification sample is repeated 4 above-mentioned steps (1)～(3), obtain Selacholeic acid ethyl ester content and be 90% product.
Specific embodiment 5:
(1) gets the mixture of 1g Selacholeic acid methyl esters and methyl erucate; Wherein Selacholeic acid content is 38%, and Selacholeic acid methyl esters and methyl erucate mol ratio are 1: 1.4, adds 50ml propyl alcohol and 7g urea; After being stirred to the solution clear in 60 ℃ of water-baths, at 50 ℃ of following inclusion 24h.
(2) gained urea inclusion crystallization filtering separation gets urea inclusion crystallising part and filtrating part;
(3) get the urea inclusion crystallising part, be dissolved in zero(ppm) water, use petroleum ether extraction, standing demix is got upper organic phase, reduction vaporization in 60 ℃ of water-baths, and vapor condensation reclaims sherwood oil, and liquid phase promptly gets the sample of purifying;
(4) the purification sample is repeated 6 above-mentioned steps (1)～(3), obtain Selacholeic acid methyl esters content and be 93% product.
Claims (4)
1. the method for neural acid esters of from neural acid esters and eruciate mixer, purifying is characterized in that comprising the steps:
(1) be rich in Selacholeic acid methyl esters and methyl erucate mixture or be rich in the Selacholeic acid ethyl ester and the ethyl erucate mixture in; Ratio in mixture and low-carbon alcohol is that 1g: 20～50ml adds low-carbon alcohol; Mass ratio by mixture and urea is 1: 3～7 adding urea again; 60～80 ℃ be stirred to the solution clear after, at 20～50 ℃ of inclusion 5～24h, obtain urea inclusion;
(2) gained urea inclusion suction filtration or filtering separation get urea inclusion crystallising part and filtrating part;
(3) get the urea inclusion crystallising part, be dissolved in zero(ppm) water, use petroleum ether extraction, standing demix is got upper organic phase, reduction vaporization under 40～60 ℃ of temperature, and vapor condensation reclaims sherwood oil, and liquid phase promptly gets the sample of purifying;
(4) the purification sample is repeated above-mentioned (1)～(3) step, obtain Selacholeic acid methyl esters or Selacholeic acid ethyl ester.
2. the method for a kind of neural acid esters of from neural acid esters and eruciate mixer, purifying as claimed in claim 1 is characterized in that being rich in that the mol ratio of Selacholeic acid methyl esters and methyl erucate is 1: 0.5～5 in Selacholeic acid methyl esters and the methyl erucate mixture described in the step (1).
3. the method for a kind of neural acid esters of from neural acid esters and eruciate mixer, purifying as claimed in claim 1 is characterized in that being rich in that the mol ratio of Selacholeic acid ethyl ester and ethyl erucate is 1: 0.5～5 in Selacholeic acid ethyl ester and the ethyl erucate mixture described in the step (1).
4. the method for a kind of neural acid esters of from neural acid esters and eruciate mixer, purifying as claimed in claim 1 is characterized in that the low-carbon alcohol described in the step (1) is methyl alcohol, ethanol or propyl alcohol.
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| CN2009100737750A CN101486647B (en) | 2009-02-11 | 2009-02-11 | Method for extracting nervonate from nervonate and eruciate mixer |
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| CN2009100737750A CN101486647B (en) | 2009-02-11 | 2009-02-11 | Method for extracting nervonate from nervonate and eruciate mixer |
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| CN101486647B true CN101486647B (en) | 2012-05-30 |
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| CN114933529B (en) * | 2022-05-16 | 2023-12-15 | 北京化工大学 | Method for separating and preparing high-purity ethyl nervonate from acer truncatum kernel |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1160037A (en) * | 1996-10-28 | 1997-09-24 | 浙江大学 | Method for separation and preparation of nervonic acid |
| CN1609090A (en) * | 2003-10-23 | 2005-04-27 | 杨凌元宝枫生物制品有限公司 | Technological process of extracting nervonic acid from Acertruncatum Bunge oil |
| CN1775732A (en) * | 2005-11-22 | 2006-05-24 | 陕西宝枫科技股份有限公司 | Method for extracting nervonic acid from acer truncatum buge oil |
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- 2009-02-11 CN CN2009100737750A patent/CN101486647B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1160037A (en) * | 1996-10-28 | 1997-09-24 | 浙江大学 | Method for separation and preparation of nervonic acid |
| CN1609090A (en) * | 2003-10-23 | 2005-04-27 | 杨凌元宝枫生物制品有限公司 | Technological process of extracting nervonic acid from Acertruncatum Bunge oil |
| CN1775732A (en) * | 2005-11-22 | 2006-05-24 | 陕西宝枫科技股份有限公司 | Method for extracting nervonic acid from acer truncatum buge oil |
Non-Patent Citations (1)
| Title |
|---|
| 徐文晖.元宝枫油中神经酸的初步分离.《中国油脂》.2007,第32卷(第11期),49-51. * |
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