CN101575282B - Method for using molecular distillation to extract nervonic acid from acer truncatum buge oil - Google Patents
Method for using molecular distillation to extract nervonic acid from acer truncatum buge oil Download PDFInfo
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- CN101575282B CN101575282B CN2009100747911A CN200910074791A CN101575282B CN 101575282 B CN101575282 B CN 101575282B CN 2009100747911 A CN2009100747911 A CN 2009100747911A CN 200910074791 A CN200910074791 A CN 200910074791A CN 101575282 B CN101575282 B CN 101575282B
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Abstract
The invention relates to a method for using molecular distillation to extract nervonic acid from acer truncatum buge oil, which obtains the acer truncatum buge oil with acer truncatum buge seeds as raw materials by extracting and pressing; absolute ethyl alcohol or methanol and the acer truncatum buge oil are mixed, then the catalyst is added for reaction, unreacted ethyl alcohol or methanol is removed, glycerine is separated, and fatty acid ester of the acer truncatum buge oil is obtained by rinsing; five-grade molecular distillation is carried out to the fatty acid ester of the acer truncatum buge oil under the condition of different vacuum degrees and temperature so as to obtain the fatty acid ester with the content of nervonic acid ester of more than 80 wt percent; the fatty acid esteris saponated, acid is added to adjust pH value to be 2 to 3, rinsing is carried out so as to lead the fatty acid ester to be neutral, petroleum ether is used for extracting the fatty acid, the petrol eum ether is then removed and the product with the content of nervonic acid of more than 80 wt percent is obtained. The invention has the advantages of low operating temperature, simple technique and high content of nervonic acid.
Description
Affiliated field
The invention belongs to a kind of method of extracting Selacholeic acid, be specifically related to a kind of method of utilizing molecular distillation technique from Acertruncatum Bunge oil, to extract Selacholeic acid.
Background technology
Selacholeic acid has another name called shark acid, and formal name used at school is suitable-15-tetracosenoic acid; Be found in mammiferous nervous tissue the earliest; So the called after Selacholeic acid, Selacholeic acid content in nervous tissue and cerebral tissue is higher, is the core natural component of cerebral nerve fiber and neurocyte.Selacholeic acid not only has the function of enlivening brain cell, treatment health immunodeficiency property disease, cardiovascular disorder to a certain extent; But also be the raw material of synthetic musk ketone, ring ten five-carbon ketones, 15 carbon lactones, sex pheromone of Ostrinia furnacalis, housefly sex pheromone etc., therefore separating the purification Selacholeic acid has high practical value.The Selacholeic acid suitability for industrialized production that still is unrealized so far mainly obtains Selacholeic acid through dual mode at present, and the one, the chemosynthesis Selacholeic acid, but operational path is complicated, and productive rate is low, is difficult to realize industriallization; The 2nd, from shark oil shai and shark brain, extract, receive resource limit, also can't mass production.
Both at home and abroad scientist begins one's study and from plant, extracts Selacholeic acid, has 10 kinds, herbage to have 5 kinds through the Selacholeic acid content of discovering to China's oil plant lipid acid greater than 2% xylophyta.Wherein, acer truncatum is the endemic tree that China contains the Selacholeic acid xylophyta, plants the benevolence oil length near 50%, and unsaturated fatty acid content reaches 92% in the Acertruncatum Bunge oil, wherein contains 5.52% Selacholeic acid.Though Selacholeic acid content is low than malania oleifera, the solid amount of acer truncatum seeds is big, and acer truncatum has bigger exploitation to be worth as food, medicine and industrial chemicals.But owing to except Selacholeic acid, also contain various lipid acid such as a large amount of oleic acid, eicosenoic acid, erucic acid in the raw oil, their structures are close, and similar performance is not easy to separate.
The firm grade in Korean proposes a kind of method (number of patent application: 200510096369.8) that from Acertruncatum Bunge oil, extracts Selacholeic acid; Its operational path comprises saponification and the weak adsorption and purification process of urea low temperature embedding process, normal temperature vacuum distillation process, freezing fractional crystallization process, methyl esterification of fatty acid and sepn process selectivity, and route is complicated.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).Luo Yongzhu etc. propose a kind of method (number of patent application: 200710018195.2), adopt six grades of short-path distillations, collect the fatty acids products of different degree of saturation that from Acertruncatum Bunge oil, extracts the Selacholeic acid ethyl ester with molecular distillation technique.But exist distillation temperature high, the Selacholeic acid purity that repeated experiments makes has only problem such as 55%.
Summary of the invention
The object of the present invention is to provide a kind of Selacholeic acid purity high, preparation technology simply extracts the method for Selacholeic acid from Acertruncatum Bunge oil with molecular distillation technique.
In order to achieve the above object, the present invention a kind ofly extracts the method for Selacholeic acid with molecular distillation technique from Acertruncatum Bunge oil, comprise the steps:
(1) being raw material with the acer truncatum seed obtains Acertruncatum Bunge oil through supercritical extraction, No. six solvent oil extractions, petroleum ether extraction or through squeezing;
(2) absolute ethyl alcohol or methyl alcohol are mixed the catalyzer that the back adds Acertruncatum Bunge oil 1～5wt% with Acertruncatum Bunge oil with volume ratio 1: 1～10; Reaction is 1～5 hour when temperature is 50～80 ℃; Product removes unreacted ethanol or methyl alcohol, separation of glycerin, and washing obtains the Acertruncatum Bunge oil fatty ester;
(3) the Acertruncatum Bunge oil fatty ester that makes is carried out the Pyatyi short-path distillation under different vacuum tightnesss and temperature condition, the first step removes sterol and vitamin E, separates to obtain C
14～C
24Fatty ester; With C
14～C
24Fatty ester is that raw material carries out the second stage and removes C
14, C
16And portion C
18, separate obtaining C
18～C
24Fatty ester; With C
18～C
24Fatty ester is that raw material carries out the third stage and removes C
18And portion C
20, separate obtaining C
20～C
24Fatty ester; With C
20～C
24Fatty ester is that raw material carries out the fourth stage and removes C
20And portion C
22, separate obtaining C
22～C
24Fatty ester; With C
22～C
24Fatty ester is that raw material carries out level V and removes C
22And portion C
24, separate obtaining the fatty ester of Selacholeic acid ester content more than 80wt%; The 1-4 level removes part as by product;
(4) the fatty ester saponification that the level V short-path distillation is obtained, add hydrochloric acid or sulphur acid for adjusting pH value to 2～3, washing is used petroleum ether extraction lipid acid to neutral, removes sherwood oil, obtains the product of Selacholeic acid content greater than 80wt%.
31～60 ℃ of supercritical extraction temperature described in the above-mentioned steps (1), pressure 7～30MPa, 30～60 ℃ of separation temperatures, pressure 7～30MPa;
Catalyzer described in the above-mentioned steps (2) is sodium ethylate, sodium hydroxide or Pottasium Hydroxide.
In the above-mentioned steps (3), under different vacuum conditions and temperature, carry out the Pyatyi short-path distillation, concrete parameter is:
| Progression | Vacuum tightness (pa) | Temperature (℃) | Remove part | Collect part |
| The first step | 0.1～0.9 | 140～145 | Sterol, vitamin E | C 14～C 24Fatty ester |
| The second stage | 2.5～9 | 115～120 | C 14、C 16And portion C 18 | C 18～C 24Fatty ester |
| The third stage | 1.5～2.5 | 120～125 | C 18And portion C 20 | C 20～C 24Fatty ester |
| The fourth stage | 1～1.5 | 125～135 | C 20And portion C 22 | C 22～C 24Fatty ester |
| Level V | 0.9～1 | 135～140 | C 22And portion C 24 | The fatty ester of Selacholeic acid ester content more than 80% |
In the above-mentioned steps (4), the saponification process is with fatty ester and excessive NaOH or KOH aqueous solution, reflux 0.5～3 hour.
Compared with prior art, advantage of the present invention is following:
1, service temperature is low, helps avoiding the destruction of biologically active substance, and technology is simple;
2, the Selacholeic acid content that obtains is high;
3, be product with lipid acid rather than fatty ester, be beneficial to body and absorb.
Embodiment
Embodiment 1:
(1) acer truncatum seed 1000 grams is pulverized the extractor of packing into, obtain 120 gram Acertruncatum Bunge oils, 60 ℃ of extraction temperature, pressure 7MPa, 30 ℃ of separation temperatures, pressure 7MPa through supercritical carbon dioxide extraction;
(2) 30 milliliters of absolute ethyl alcohols are mixed the back with 100 milliliters of Acertruncatum Bunge oils and add 1.2 gram NaOH, reaction is 3.5 hours when temperature is 60 ℃, and the product distillation removes unreacted ethanol, and separation of glycerin after washing denitrating catalyst obtains 75 milliliters of Acertruncatum Bunge oil ethyl esters;
(3) separation of Selacholeic acid ethyl ester: the Acertruncatum Bunge oil ethyl ester to making carries out short-path distillation under different vacuum tightnesss and temperature condition, operational condition is:
| Progression | Vacuum tightness (pa) | Temperature (℃) | Remove part | Collect part |
| The first step | 0.1 | 140 | Sterol, vitamin E | C 14～C 24Fatty-acid ethyl ester |
| The second stage | 2.5 | 115 | C 14、C 16And portion C 18 | C 18～C 24Fatty-acid ethyl ester |
| The third stage | 1.5 | 120 | C 18And portion C 20 | C 20～C 24Fatty-acid ethyl ester |
| The fourth stage | 1 | 125 | C 20And portion C 22 | C 22～C 24Fatty-acid ethyl ester |
| Level V | 0.9 | 135 | C 22And portion C 24 | The fatty-acid ethyl ester of Selacholeic acid ethyl ester content 80.3% |
(4) fatty-acid ethyl ester and the excessive NaOH aqueous solution that the Pyatyi short-path distillation are obtained, reflux saponification in 1.5 hours is with salt acid for adjusting pH value to 2; Washing is to neutral; Use petroleum ether extraction lipid acid, remove sherwood oil, obtain the product of Selacholeic acid content 80.3%.
Embodiment 2:
(1) acer truncatum seed 1000 grams is pulverized the extractor of packing into, obtain 120 gram Acertruncatum Bunge oils, 60 ℃ of extraction temperature, pressure 30MPa, 60 ℃ of separation temperatures, pressure 7MPa through supercritical carbon dioxide extraction;
(2) 25 milliliters of absolute ethyl alcohols are mixed the back with 100 milliliters of Acertruncatum Bunge oils and add 2 gram NaOH, reaction is 2.5 hours when temperature is 65 ℃, and the product distillation removes unreacted ethanol, and separation of glycerin after washing denitrating catalyst obtains 75 milliliters of Acertruncatum Bunge oil ethyl esters;
(3) separation of Selacholeic acid ethyl ester: the Acertruncatum Bunge oil ethyl ester to making carries out short-path distillation under different vacuum tightnesss and temperature condition, operational condition is:
| Progression | Vacuum tightness (pa) | Temperature (℃) | Remove part | Collect part |
| The first step | 0.2 | 141 | Sterol, vitamin E | C 14～C 24Fatty-acid ethyl ester |
| The second stage | 3 | 115 | C 14、C 16And portion C 18 | C 18～C 24Fatty-acid ethyl ester |
| The third stage | 1.7 | 121 | C 18And portion C 20 | C 20～C 24Fatty-acid ethyl ester |
| The fourth stage | 1 | 127 | C 20And portion C 22 | C 22～C 24Fatty-acid ethyl ester |
| Level V | 0.9 | 136 | C 22And portion C 24 | The fatty-acid ethyl ester of Selacholeic acid ethyl ester content 80.4% |
(4) fatty-acid ethyl ester and the excessive NaOH aqueous solution that the Pyatyi short-path distillation are obtained, reflux saponification in 1.5 hours is with salt acid for adjusting pH value to 2; Washing is to neutral; Use petroleum ether extraction lipid acid, remove sherwood oil, obtain the product of Selacholeic acid content 80.4%.
Embodiment 3:
(1) the 500 gram pulverizing of acer truncatum seed is obtained 70 gram Acertruncatum Bunge oils with No. six solvent oils extractions;
(2) 70 milliliters of absolute ethyl alcohols are mixed the back with 70 milliliters of Acertruncatum Bunge oils and add 55 milliliters of sodium ethylates, reaction is 5 hours when temperature is 50 ℃, and the product distillation removes unreacted ethanol, and separation of glycerin after washing denitrating catalyst obtains 55 milliliters of Acertruncatum Bunge oil ethyl esters;
(3) separation of Selacholeic acid ethyl ester: the Acertruncatum Bunge oil ethyl ester to making carries out short-path distillation under different vacuum tightnesss and temperature condition, operational condition is:
| Progression | Vacuum tightness (pa) | Temperature (℃) | Remove part | Collect part |
| The first step | 0.3 | 142 | Sterol, vitamin E | C 14～C 24Fatty-acid ethyl ester |
| The second stage | 4 | 116 | C 14、C 16And portion C 18 | C 18～C 24Fatty-acid ethyl ester |
| The third stage | 1.8 | 122 | C 18And portion C 20 | C 20～C 24Fatty-acid ethyl ester |
| The fourth stage | 1.1 | 128 | C 20And portion C 22 | C 22～C 24Fatty-acid ethyl ester |
| Level V | 0.9 | 137 | C 22And portion C 24 | The fatty-acid ethyl ester of Selacholeic acid ethyl ester content 80.7% |
(4) the Selacholeic acid ethyl ester and the excessive KOH aqueous solution that the Pyatyi short-path distillation are obtained, reflux saponification in 2 hours, with salt acid for adjusting pH value to 2, washing is used petroleum ether extraction lipid acid to neutral, removes sherwood oil, obtains the product of Selacholeic acid content 80.7%.
Embodiment 4:
(1) the 1500 gram pulverizing of acer truncatum seed is obtained 210 gram Acertruncatum Bunge oils with petroleum ether extraction;
(2) 20 milliliters of absolute ethyl alcohols are mixed the back with 200 milliliters of Acertruncatum Bunge oils and add 10 gram NaOH, reaction is 1.5 hours when temperature is 75 ℃, and the product distillation removes unreacted ethanol, and separation of glycerin after washing denitrating catalyst 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 to making carries out short-path distillation under different vacuum tightnesss and temperature condition, collect separated products at different levels.
(3) separation of Selacholeic acid ethyl ester: the Acertruncatum Bunge oil ethyl ester to making carries out short-path distillation under different vacuum tightnesss and temperature condition, operational condition is:
| Progression | Vacuum tightness (pa) | Temperature (℃) | Remove part | Collect part |
| The first step | 0.5 | 143 | Sterol, vitamin E | C 14～C 24Fatty-acid ethyl ester |
| The second stage | 5 | 117 | C 14、C 16And portion C 18 | C 18～C 24Fatty-acid ethyl ester |
| The third stage | 2 | 123 | C 18And portion C 20 | C 20～C 24Fatty-acid ethyl ester |
| The fourth stage | 1.2 | 130 | C 20And portion C 22 | C 22～C 24Fatty-acid ethyl ester |
| Level V | 1 | 138 | C 22And portion C 24 | The fatty-acid ethyl ester of Selacholeic acid ethyl ester content 80.5% |
(4) the Selacholeic acid ethyl ester and the excessive NaOH aqueous solution that the Pyatyi short-path distillation are obtained, reflux saponification in 3 hours, with salt acid for adjusting pH value to 2, washing is used petroleum ether extraction lipid acid to neutral, removes sherwood oil, obtains the product of Selacholeic acid content 80.5%.
Embodiment 5:
(1) acer truncatum seed 500 grams is pulverized the extractor of packing into, obtain 60 gram Acertruncatum Bunge oils, 31 ℃ of extraction temperature, pressure 30MPa, 30 ℃ of separation temperatures, pressure 7MPa through supercritical carbon dioxide extraction;
(2) 20 milliliters of anhydrous methanols are mixed the back with 40 milliliters of Acertruncatum Bunge oils and add 2 gram NaOH, reaction is 2 hours when temperature is 70 ℃, and the product distillation removes unreacted methanol, and separation of glycerin after washing denitrating catalyst obtains 30 milliliters of Acertruncatum Bunge oil methyl esters;
(3) separation of Selacholeic acid methyl esters: the Acertruncatum Bunge oil methyl esters to making carries out short-path distillation under different vacuum tightnesss and temperature condition, operational condition is:
| Progression | Vacuum tightness (pa) | Temperature (℃) | Remove part | Collect part |
| The first step | 0.7 | 144 | Sterol, vitamin E | C 14～C 24Fatty acid methyl ester |
| The second stage | 7 | 118 | C 14、C 16And portion C 18 | C 18～C 24Fatty acid methyl ester |
| The third stage | 2.3 | 124 | C 18And portion C 20 | C 20～C 24Fatty acid methyl ester |
| The fourth stage | 1.3 | 133 | C 20And portion C 22 | C 22～C 24Fatty acid methyl ester |
| Level V | 1 | 139 | C 22And portion C 24 | The fatty acid methyl ester of Selacholeic acid methyl esters content 80.2% |
(4) the Selacholeic acid methyl esters and the excessive NaOH aqueous solution that the Pyatyi short-path distillation are obtained, reflux saponification in 0.5 hour is with salt acid for adjusting pH value to 3; Washing is to neutral; Use petroleum ether extraction lipid acid, remove sherwood oil, obtain the product of Selacholeic acid content 80.2%.
Embodiment 6:
(1) the 1000 gram pulverizing of acer truncatum seed is obtained 120 gram Acertruncatum Bunge oils through the machine squeezing;
(2) 20 milliliters of absolute ethyl alcohols are mixed the back with 120 milliliters of Acertruncatum Bunge oils and add 5 gram KOH, reaction is 1 hour when temperature is 80 ℃, and the product distillation removes unreacted ethanol, and separation of glycerin after washing denitrating catalyst obtains 92 milliliters of Acertruncatum Bunge oil ethyl esters;
(3) separation of Selacholeic acid ethyl ester: the Acertruncatum Bunge oil ethyl ester to making carries out short-path distillation under different vacuum tightnesss and temperature condition, operational condition is:
| Progression | Vacuum tightness (pa) | Temperature (℃) | Remove part | Collect part |
| The first step | 0.9 | 145 | Sterol, vitamin E | C 14～C 24Fatty-acid ethyl ester |
| The second stage | 9 | 120 | C 14、C 16And portion C 18 | C 18～C 24Fatty-acid ethyl ester |
| The third stage | 2.5 | 125 | C 18And portion C 20 | C 20～C 24Fatty-acid ethyl ester |
| The fourth stage | 1.5 | 135 | C 20And portion C 22 | C 22～C 24Fatty-acid ethyl ester |
| Level V | 1 | 140 | C 22And portion C 24 | The fatty-acid ethyl ester of Selacholeic acid ethyl ester content 80% |
(4) the Selacholeic acid ethyl ester and the excessive KOH aqueous solution that the Pyatyi short-path distillation are obtained, reflux saponification in 1 hour adds sulphur acid for adjusting pH value to 2, and washing is used petroleum ether extraction lipid acid to neutral, removes sherwood oil, obtains the product of Selacholeic acid content 80%.
Claims (4)
1. a method of utilizing short-path distillation from Acertruncatum Bunge oil, to extract Selacholeic acid is characterized in that comprising the steps:
(1) being raw material with the acer truncatum seed obtains Acertruncatum Bunge oil through supercritical extraction, No. six solvent oil extractions, petroleum ether extraction or through squeezing;
(2) absolute ethyl alcohol or methyl alcohol are mixed the catalyzer that the back adds Acertruncatum Bunge oil 1～5wt% with Acertruncatum Bunge oil with volume ratio 1: 1～10; Reaction is 1～5 hour when temperature is 50～80 ℃; Product removes unreacted ethanol or methyl alcohol, separation of glycerin, and washing obtains the Acertruncatum Bunge oil fatty ester;
(3) the Acertruncatum Bunge oil fatty ester that makes is carried out the Pyatyi short-path distillation under different vacuum tightnesss and temperature condition, the first step removes sterol and vitamin E, separates to obtain C
14～C
24Fatty ester; With C
14～C
24Fatty ester is that raw material carries out the second stage and removes C
14, C
16And portion C
18, separate obtaining C
18～C
24Fatty ester; With C
18～C
24Fatty ester is that raw material carries out the third stage and removes C
18And portion C
20, separate obtaining C
20～C
24Fatty ester; With C
20～C
24Fatty ester is that raw material carries out the fourth stage and removes C
20And portion C
22, separate obtaining C
22～C
24Fatty ester; With C
22～C
24Fatty ester is that raw material carries out level V and removes C
22And portion C
24, separate obtaining the fatty ester of Selacholeic acid ester content more than 80wt%; The 1-4 level removes part as by product;
(4) the fatty ester saponification that the level V short-path distillation is obtained, add hydrochloric acid or sulphur acid for adjusting pH value to 2～3, washing is used petroleum ether extraction lipid acid to neutral, removes sherwood oil, obtains the product of Selacholeic acid content greater than 80wt%;
Vacuum condition and temperature in the said step (3) are following:
2. a kind of method of utilizing short-path distillation from Acertruncatum Bunge oil, to extract Selacholeic acid as claimed in claim 1 is characterized in that 31～60 ℃ of the supercritical extraction temperature described in the step (1), pressure 7～30MPa, 30～60 ℃ of separation temperatures, pressure 7～30MPa.
3. a kind of method of utilizing short-path distillation from Acertruncatum Bunge oil, to extract Selacholeic acid as claimed in claim 1 is characterized in that the catalyzer described in the step (2) is sodium ethylate, sodium hydroxide or Pottasium Hydroxide.
4. a kind of method of utilizing short-path distillation from Acertruncatum Bunge oil, to extract Selacholeic acid as claimed in claim 1 is characterized in that saponification is with fatty ester and excessive NaOH or KOH aqueous solution, reflux 0.5～3 hour in the step (4).
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| CN103315302B (en) * | 2013-05-07 | 2014-06-04 | 江苏丹枫神源生物科技有限公司 | Mono maple nervonic acid soft capsules and preparation process thereof |
| 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 |
| CN105503580B (en) * | 2015-12-09 | 2017-07-21 | 江西青春康源制药有限公司 | A kind of extraction separation method of nervonic acid |
| 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 |
| CN107445826A (en) * | 2017-07-25 | 2017-12-08 | 天津泽达天健科技有限公司 | A kind of preparation method of neural acid esters |
| 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 |
| CN108863764A (en) * | 2018-07-20 | 2018-11-23 | 李明龙 | A kind of improvement memory improves the nervonic acid piece preparation method of sleep quality |
| CN111072469B (en) * | 2019-12-16 | 2022-12-09 | 西安尚诚生物科技有限公司 | Method for extracting natural nervonic acid |
| CN112299986A (en) * | 2020-11-25 | 2021-02-02 | 宝鸡文理学院 | Separation and purification process of nervonic acid in acer truncatum seed oil |
| CN113173847A (en) * | 2021-05-06 | 2021-07-27 | 中国科学院大学 | Method for separating nervonic acid based on simulated moving bed |
| CN114468299B (en) * | 2022-01-14 | 2023-12-01 | 安徽省纽斯康生物工程有限公司 | Nervonic acid-rich dietary supplement for promoting brain functions and preparation method and application thereof |
| CN114853593B (en) * | 2022-05-12 | 2023-08-29 | 北京化工大学 | Method for extracting high-purity nervonic acid from acer truncatum oil |
| CN116210677A (en) * | 2022-09-07 | 2023-06-06 | 蚌埠医学院 | Method for manufacturing whole body nerve specimen of rabbit |
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| 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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