CN101429112B - Method for distillation separation of mixture of nervonic acid and erucic acid from acer truncatum oil - Google Patents
Method for distillation separation of mixture of nervonic acid and erucic acid from acer truncatum oil Download PDFInfo
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- CN101429112B CN101429112B CN2008100801184A CN200810080118A CN101429112B CN 101429112 B CN101429112 B CN 101429112B CN 2008100801184 A CN2008100801184 A CN 2008100801184A CN 200810080118 A CN200810080118 A CN 200810080118A CN 101429112 B CN101429112 B CN 101429112B
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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
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
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Abstract
The invention relates to a method for distilling and separating a mixture of nervonic acid and erucidic acid from acer truncatum oil molecules. The method comprises the following steps: acer truncatum seeds are subjected to supercritical carbon dioxide extraction method, a leaching method, or a squeezing method to obtain acer truncatum oil; a mixture of anhydrous ethanol and the acer truncatum oil is added with a catalyst and reacts for 1 to 5 hours at a temperature of between 50 and 80 DEG C; a product is separated to obtain glycerol and remove unreacted ethanol to obtain acer truncatum oil ethyl ester; the acer truncatum oil ethyl ester is subjected to molecular distillation under the conditions of controlling vacuum degree and temperature to obtain mixed fatty acid ethyl ester rich in the erucidic acid and the nervonic acid; and the mixed fatty acid ethyl rich in the erucidic acid and the nervonic acid is saponified and is added with acid to adjust the PH value to be neutral, is washed, is subjected to fatty acid extraction through an organic solvent and the organic solvent removal to obtain a product. The method has the advantages of low operation temperature and high utilization rate of resource.
Description
Affiliated field
The present invention relates to a kind of method of from Acertruncatum Bunge oil, separating Selacholeic acid and erucic acid with molecular distillation technique.
Technical background
Selacholeic acid is suitable-15-tetracosenoic acid, is the long-chain monounsaturated fatty acids.Selacholeic acid is a biomembranous important composition composition in the nervous tissue, is the significant composition of medullary substance in the brain glucoside.The essential high-grade nutrient element that Selacholeic acid is particularly brain cell, optic cell, peripheral nerve growth of neurocyte, grow and keep again is the treasure of nutrition brain.Selacholeic acid not only is suitable for the nutritive health-care of the daily brain of healthy people, 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 has obvious blood fat reducing, reduces blood viscosity, suppresses hematoblastic cohesive force and inflammatory factor, high density lipoprotein increasing.Selacholeic acid has special efficacy to treating some tetter.Along with to the continuous development of Selacholeic acid 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.
Erucic acid is suitable-13-Decosahedaenoic acid, also is the long-chain monounsaturated fatty acids.In human body, can be converted into Selacholeic acid [Hou Jingde etc., Selacholeic acid and brain health, China Science Tech Publishing House, 2007].Last century end was once once having the scholar to think that erucic acid is nondigestible, harmful, so the rapeseed oil that content of erucic acid is very high is not suitable for human edible [Beare-Rogers I.L.et al., Can.Inst.Food Technol.J., 1971,4,120-124], for this reason China older generation oil chemistry expert professor Tang Feng specially write articles point out rapeseed oil digestibility up to 99% (being as good as) with other edible oil, people can be relieved edible by custom, the non-digestible saying of erucic acid has been negated that [Chen Wenlin, rape oil are wronged and rehabilitate, and science and technology of grain and oil is with economical by the human trial result also, 1997 (2), 67], as China Yangtze valley, India and European resident always eat rapeseed oil, dissect corpse and also do not find myocarditis and the sedimentary trace of erucic acid.Nineteen fifty-three, Canada scholar K.K.Carroll finds that Selacholeic acid and erucic acid have good effect [K.K.Carroll to the disease that treatment suprarenal gland cholesterol causes, J.Biol.Chem., 1953,200,287-92], also there is research to point out that erucic acid and Selacholeic acid cause demyelinating disease that positive therapeutic effect [Coupland Keith etc., US patent 5194448,1993 are arranged to suprarenal gland white corpuscle malnutrition, 5331009,1994].
Acer truncatum mainly is distributed in middle and lower reaches each province, the Yellow River and THE SOUTH OF NORTHEAST CHINA, Jiangsu, Anhui etc.Shaanxi in recent years, Shanxi, Sichuan, Chongqing, Jiangsu, Beijing, Henan, Shandong, Anhui, Yunnan, Gansu, provinces and cities such as Ningxia greatly develop or introduce, and it is more and more wider to distribute.Its solid amount is big, plant the benevolence oil length near 50%, contain 12～18% erucic acid and 5～6% Selacholeic acid in the Acertruncatum Bunge oil, but because various fatty acid structures are close, character is close, separate purification difficult, from stock oil, extract, separate high Selacholeic acid or the erucic acid health-care medical product of content, become the technical bottleneck of restriction Selacholeic acid product application.
At present, domestic from plant 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, it is raw material with the high grease of Selacholeic acid content that metal salt precipitate method, emulsification partition method, solvent crystallization are separated Selacholeic acid many, as the malania oleifera wet goods.Selacholeic acid content is relatively low in the acer truncatum grease, directly adopts metal salt precipitate method, emulsification partition method and solvent crystallization infeasible.The firm grade in Korean discloses a kind of method of extracting Selacholeic acid from Acertruncatum Bunge oil, its operational path comprises saponification and urea low temperature embedding process, the normal temperature vacuum distillation process, cryogenic 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, exist route complicated, wash problems such as easy emulsification [number of patent application: 200510096369.8], Luo Yongzhu etc. disclose the method [number of patent application: 200710018195.2] of extracting the Selacholeic acid ethyl ester with molecular distillation technique from Acertruncatum Bunge oil, but exist molecular distillation progression many, problems such as distillation temperature height, and be target only to separate Selacholeic acid, problem such as the level of resources utilization is low.
Summary of the invention:
The object of the present invention is to provide a kind of method of from Acertruncatum Bunge oil, separating Selacholeic acid and presoma (erucic acid) thereof, to overcome the problem that prior art molecular distillation progression is many, distillation temperature is high, resource utilization is low with molecular distillation technique.
In order to achieve the above object, the present invention is a kind of method of separating Selacholeic acid and erucic acid with molecular distillation technique from Acertruncatum Bunge oil, comprises the steps:
(1) the preparation Acertruncatum Bunge oil is that raw material obtains Acertruncatum Bunge oil by supercritical carbon dioxide extraction method, lixiviation process or milling process with the acer truncatum seed;
(2) preparation Acertruncatum Bunge oil ethyl ester: dehydrated alcohol is mixed with volume ratio 1: 1～10 with Acertruncatum Bunge oil, and 1～10% catalyzer of adding Acertruncatum Bunge oil weight, reaction is 1～5 hour when temperature is 50～80 ℃, and the product separation of glycerin removes unreacted ethanol and obtains the Acertruncatum Bunge oil ethyl ester;
(3) separating of erucic acid and Selacholeic acid ethyl ester: the Acertruncatum Bunge oil ethyl ester that makes is carried out molecular distillation under control vacuum tightness and temperature condition, obtain being rich in the heavy component of the mixing-in fat acetoacetic ester of erucic acid and Selacholeic acid;
(4) will be rich in erucic acid and Selacholeic acid the saponification of mixing-in fat acetoacetic ester, add acid for adjusting pH value to neutral, washing, organic solvent extraction lipid acid, desolventizing obtains product.
The overcritical collection processing condition of carbon dioxide process described in the above-mentioned steps (1) are: extraction temperature 35-60 ℃, and extracting pressure 24-32MPa, separation temperature 50-70 ℃, separating pressure 6-9MPa.
Lixiviation process described in the above-mentioned steps (1) can adopt hexane, No. six solvent oils, ethyl acetate, acetone and other organic solvent to extract, and desolventizing obtains Acertruncatum Bunge oil.
Milling process described in the above-mentioned steps (1) is directly grease to be pushed from oil plant by mechanical pressure.
Catalyzer described in the above-mentioned steps (2) is sodium ethylate, sodium hydroxide or potassium hydroxide.
Carry out the two-stage molecular distillation under control vacuum tightness described in the above-mentioned steps (3) and the temperature condition, actual conditions is: the Acertruncatum Bunge oil ethyl ester carries out first step molecular distillation, vacuum tightness 0.1～1Pa, 135～145 ℃ of temperature, the light component that obtains carries out second stage molecular distillation, vacuum tightness 5～9Pa, 120～130 ℃ of temperature obtain the heavy component of second stage molecular distillation.
In the above-mentioned steps (4), described saponification is with fatty-acid ethyl ester and excessive NaOH or KOH aqueous solution, reflux 0.5～3 hour.
Compared with prior art, advantage of the present invention is as follows:
1, service temperature is low, helps avoiding the destruction of biologically active substance;
2, molecular distillation progression is few, separates obtaining Selacholeic acid and the erucic acid total content surpasses 90% product by secondary.Reduce running cost, be convenient to industrialization;
3, with Selacholeic acid and presoma erucic acid thereof as target product, improved efficiency of resource.
4, be product with lipid acid rather than fatty-acid ethyl ester, be more conducive to body and absorb.
Embodiment
Embodiment 1:
(1) acer truncatum seed 500 grams are pulverized the extractor of packing into, 45 ℃ of supercritical carbon dioxide extraction temperature, pressure 30MPa, 60 ℃ of separation temperatures, pressure 8MPa obtains 60 gram Acertruncatum Bunge oils;
(2) 20 milliliters of dehydrated alcohols are mixed the back with 40 milliliters of Acertruncatum Bunge oils and add 2 gram NaOH, reaction is 2 hours when temperature is 70 ℃, product separation of glycerin after washing denitrating catalyst, and distillation removes unreacted ethanol, obtains 30 milliliters of Acertruncatum Bunge oil ethyl esters;
(3) separating of erucic acid and Selacholeic acid ethyl ester: the Acertruncatum Bunge oil ethyl ester that makes is carried out the two-stage molecular distillation under different vacuum tightnesss and temperature condition, the first step, vacuum tightness 0.2Pa, 136 ℃ of temperature, light component enters second stage molecular distillation, vacuum tightness 6Pa, 122 ℃ of temperature, collect the heavy component of second stage molecular distillation, gas chromatographic analysis Selacholeic acid ethyl ester content 46%, ethyl erucate content 45%.
(4) fatty-acid ethyl ester that is rich in erucic acid and Selacholeic acid that (3) are obtained and excessive NaOH aqueous solution, reflux saponification in 0.5 hour to neutral, obtains Selacholeic acid and erucic acid mixture with the salt acid for adjusting pH value.
Embodiment 2:
(1) the 5000 gram pulverizing of acer truncatum seed is obtained 480 gram Acertruncatum Bunge oils by squeezing;
(2) 20 milliliters of dehydrated alcohols are mixed the back with 120 milliliters of Acertruncatum Bunge oils and add 8 gram KOH, reaction is 1 hour when temperature is 76 ℃, product separation of glycerin after washing denitrating catalyst, and distillation removes unreacted ethanol, obtains 92 milliliters of Acertruncatum Bunge oil ethyl esters;
(3) separating of erucic acid and Selacholeic acid ethyl ester: the Acertruncatum Bunge oil ethyl ester that makes is carried out the two-stage molecular distillation under different vacuum tightnesss and temperature condition, the first step, vacuum tightness 0.8Pa, 143 ℃ of temperature, light component enters second stage molecular distillation, vacuum tightness 8Pa, 125 ℃ of temperature, collect the heavy component of second stage molecular distillation, gas chromatographic analysis Selacholeic acid ethyl ester content 36%, ethyl erucate content 55%.
(4) fatty-acid ethyl ester that is rich in erucic acid and Selacholeic acid that (3) are obtained and excessive KOH aqueous solution, reflux saponification in 1 hour to neutral, obtains Selacholeic acid and erucic acid mixture with the salt acid for adjusting pH value.
Embodiment 3:
(1) acer truncatum seed 500 gram is pulverized extracted to such an extent that 70 restrain Acertruncatum Bunge oils with No. six solvent oils;
(2) 20 milliliters of dehydrated alcohols that contain 2% sodium ethylate are mixed with 20 milliliters of Acertruncatum Bunge oils, reaction is 5 hours when temperature is 50 ℃, product separation of glycerin after washing denitrating catalyst, and distillation removes unreacted ethanol, obtains 15 milliliters of Acertruncatum Bunge oil ethyl esters;
(3) separating of erucic acid and Selacholeic acid ethyl ester: the Acertruncatum Bunge oil ethyl ester that makes is carried out the two-stage molecular distillation under different vacuum tightnesss and temperature condition, the first step, vacuum tightness 0.5Pa, 140 ℃ of temperature, light component enters second stage molecular distillation, vacuum tightness 6Pa, 128 ℃ of temperature, collect the heavy component of second stage molecular distillation, gas chromatographic analysis Selacholeic acid ethyl ester content 41%, ethyl erucate content 51%.
(4) fatty-acid ethyl ester that is rich in erucic acid and Selacholeic acid that (3) are obtained and excessive KOH aqueous solution, reflux saponification in 2 hours to neutral, obtains Selacholeic acid and erucic acid mixture with the salt acid for adjusting pH value.
Embodiment 4:
(1) 3000 gram acer truncatum seeds is pulverized petroleum ether extraction and obtain 330 gram Acertruncatum Bunge oils;
(2) 20 milliliters of dehydrated alcohols are mixed the back with 200 milliliters of Acertruncatum Bunge oils and add 5 gram NaOH, reaction is 1.5 hours when temperature is 75 ℃, product separation of glycerin after washing denitrating catalyst, and distillation removes unreacted ethanol, obtains 156 milliliters of Acertruncatum Bunge oil ethyl esters;
(3) separating of erucic acid and Selacholeic acid ethyl ester: the Acertruncatum Bunge oil ethyl ester that makes is carried out the two-stage molecular distillation under different vacuum tightnesss and temperature condition, the first step, vacuum tightness 0.3Pa, 138 ℃ of temperature, light component enters second stage molecular distillation, vacuum tightness 9Pa, 133 ℃ of temperature, collect the heavy component of second stage molecular distillation, gas chromatographic analysis Selacholeic acid ethyl ester content 37%, ethyl erucate content 54%.
(4) fatty-acid ethyl ester that is rich in erucic acid and Selacholeic acid that (3) are obtained and excessive NaOH aqueous solution, reflux saponification in 3 hours to neutral, obtains Selacholeic acid and erucic acid mixture with the salt acid for adjusting pH value.
Embodiment 5:
(1) acer truncatum seed 1000 grams are pulverized the extractor of packing into, 55 ℃ of supercritical carbon dioxide extraction temperature, pressure 28MPa, 65 ℃ of separation temperatures, pressure 7MPa obtains 110 gram Acertruncatum Bunge oils;
(2) 20 milliliters of dehydrated alcohols are mixed the back with 80 milliliters of Acertruncatum Bunge oils and add 1 gram NaOH, reaction is 3.5 hours when temperature is 60 ℃, product separation of glycerin after washing denitrating catalyst, and distillation removes unreacted ethanol, obtains 60 milliliters of Acertruncatum Bunge oil ethyl esters;
(3) separating of erucic acid and Selacholeic acid ethyl ester: the Acertruncatum Bunge oil ethyl ester that makes is carried out the two-stage molecular distillation under different vacuum tightnesss and temperature condition, the first step, vacuum tightness 0.9Pa, 145 ℃ of temperature, light component enters second stage molecular distillation, vacuum tightness 5Pa, 135 ℃ of temperature, collect the heavy component of second stage molecular distillation, gas chromatographic analysis Selacholeic acid ethyl ester content 48%, ethyl erucate content 43%.
(4) fatty-acid ethyl ester that is rich in erucic acid and Selacholeic acid that (3) are obtained and excessive NaOH aqueous solution, reflux saponification in 1.5 hours to neutral, obtains Selacholeic acid and erucic acid mixture with the salt acid for adjusting pH value.
Claims (6)
1. isolate the method for Selacholeic acid and erucic acid mixture from the Acertruncatum Bunge oil molecular distillation for one kind, it is characterized in that comprising the steps:
(1) the preparation Acertruncatum Bunge oil is that raw material obtains Acertruncatum Bunge oil by supercritical carbon dioxide extraction method, lixiviation process or milling process with the acer truncatum seed;
(2) preparation Acertruncatum Bunge oil ethyl ester: with dehydrated alcohol and Acertruncatum Bunge oil with volume ratio 1: 1-10 mixes, and the 1-10% catalyzer of adding Acertruncatum Bunge oil weight, reaction is 1-5 hour when temperature is 50-80 ℃, and the product separation of glycerin removes unreacted ethanol and obtains the Acertruncatum Bunge oil ethyl ester;
(3) separating of erucic acid and Selacholeic acid ethyl ester: the Acertruncatum Bunge oil ethyl ester that makes is carried out molecular distillation under control vacuum tightness and temperature condition, obtain being rich in the heavy component of the mixing-in fat acetoacetic ester of erucic acid and Selacholeic acid;
(4) will be rich in the mixing-in fat acetoacetic ester saponification of erucic acid and Selacholeic acid, add acid for adjusting pH value to neutral, washing, organic solvent extraction lipid acid, desolventizing obtains product;
Carry out molecular distillation under control vacuum tightness described in the step (3) and the temperature condition, actual conditions is: the Acertruncatum Bunge oil ethyl ester carries out first step molecular distillation, vacuum tightness 0.1-1Pa, temperature 135-145 ℃, the light component that obtains carries out second stage molecular distillation, vacuum tightness 5-9Pa, obtains the heavy component of second stage molecular distillation by temperature 120-130 ℃.
2. a kind of method of isolating Selacholeic acid and erucic acid mixture from the Acertruncatum Bunge oil molecular distillation as claimed in claim 1, the carbon dioxide extraction method supercritical extraction process condition described in the step (1) that it is characterized in that is: extraction temperature 35-60 ℃, extracting pressure 24-31MPa, separation temperature 50-70 ℃, separating pressure 6-9MPa.
3. a kind of method of isolating Selacholeic acid and erucic acid mixture from the Acertruncatum Bunge oil molecular distillation as claimed in claim 1, it is characterized in that the lixiviation process described in the step (1) adopts hexane, No. six solvent oils, ethyl acetate or acetone organic solvents to extract, desolventizing obtains Acertruncatum Bunge oil.
4. as claimed in claim 1ly a kind ofly isolate the method for Selacholeic acid and erucic acid mixture from the Acertruncatum Bunge oil molecular distillation, it is characterized in that described in the step (1) milling process be directly grease to be pushed from oil plant by mechanical pressure.
5. as claimed in claim 1ly a kind ofly isolate the method for Selacholeic acid and erucic acid mixture, it is characterized in that the catalyzer described in the step (2) is sodium ethylate, sodium hydroxide or potassium hydroxide from the Acertruncatum Bunge oil molecular distillation.
6. a kind of method of isolating Selacholeic acid and erucic acid mixture from the Acertruncatum Bunge oil molecular distillation as claimed in claim 1, it is characterized in that the saponification described in the step (4) is with fatty-acid ethyl ester and excess NaOH or KOH aqueous solution, reflux 0.5-3 hour.
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Families Citing this family (7)
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| CN101575282B (en) * | 2009-06-15 | 2012-11-14 | 中国科学院山西煤炭化学研究所 | Method for using molecular distillation to extract nervonic acid from acer truncatum buge oil |
| CN103184105A (en) * | 2013-03-21 | 2013-07-03 | 长春工业大学 | Method for extracting schisandra volatile oil with 9, 12-octadecadienoic acid serving as principal component through low temperature evaporation |
| CN104629899A (en) * | 2014-12-30 | 2015-05-20 | 广州白云山汉方现代药业有限公司 | Method for extracting malania oleifera oil by virtue of supercritical CO2 fluid |
| CN105994691A (en) * | 2016-05-20 | 2016-10-12 | 洛阳泽达慧康医药科技有限公司 | Method for manufacturing blend oil with peony seed oil and acer truncatum oil |
| CN106496026A (en) * | 2016-10-21 | 2017-03-15 | 武汉藤欣生物工程有限公司 | In the method that acer truncatum buge oil prepares neural acetoacetic ester as raw material |
| CN107822136B (en) * | 2017-10-30 | 2020-09-11 | 北京利科德科技有限公司 | Food material containing high-content nervonic acid and extraction method thereof |
| CN111763560A (en) * | 2019-04-02 | 2020-10-13 | 深圳市金枫生物医药科技有限公司 | Acer truncatum oil extraction method |
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| CN100341839C (en) * | 2005-11-22 | 2007-10-10 | 陕西宝枫科技股份有限公司 | Method for extracting nervonic acid from acer truncatum buge oil |
| CN101092344A (en) * | 2007-07-06 | 2007-12-26 | 杨凌七彩生物科技有限公司 | Method for extracting nervonic acid from oil of Mono Maple by using technique of molecular distillation |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN100341839C (en) * | 2005-11-22 | 2007-10-10 | 陕西宝枫科技股份有限公司 | Method for extracting nervonic acid from acer truncatum buge oil |
| CN101092344A (en) * | 2007-07-06 | 2007-12-26 | 杨凌七彩生物科技有限公司 | Method for extracting nervonic acid from oil of Mono Maple by using technique of molecular distillation |
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