CN101092344A - Method for extracting nervonic acid from oil of Mono Maple by using technique of molecular distillation - Google Patents
Method for extracting nervonic acid from oil of Mono Maple by using technique of molecular distillation Download PDFInfo
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- CN101092344A CN101092344A CN 200710018195 CN200710018195A CN101092344A CN 101092344 A CN101092344 A CN 101092344A CN 200710018195 CN200710018195 CN 200710018195 CN 200710018195 A CN200710018195 A CN 200710018195A CN 101092344 A CN101092344 A CN 101092344A
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Abstract
This invention relates to a method for extracting nervonic acid from Acer truncatum oil by molecular distillation. The method solves the problems of complex procedures, easy emulsification, high product acid value and low product purity faced by present technique. The method comprises: (1) preparing Acer truncatum oil; (2) performing deacidification treatment on Acer truncatum oil, removing oil foot, washing with water, and dehydrating; (3) mixing Acer truncatum oil, absolute ethanol and alkaline catalyst, esterifying, washing with water, and separating to obtain ethyl nervonate; (4) performing molecular distillation in different vacuum conditions and temperatures, and collecting the product.
Description
Affiliated technical field:
The present invention relates to lipid acid fabricating technology field, be specifically related to a kind of method of from Acertruncatum Bunge oil, extracting Selacholeic acid with molecular distillation technique.
Background technology:
Selacholeic acid has another name called shark acid, and chemistry suitable-15 tetracosenoic acids by name are a kind of long-chain unsaturated fatty acids, mainly are present in human brain protein with sphingoglycolipid and sphingophospholipid form, and retina is in sperm and the nervous tissue.A large amount of medical evidences, Selacholeic acid have the brain cell of recovery tip activity, promote nerve growth and grow function, and cardiovascular and cerebrovascular and AID disease are had certain curative effect.Therefore the extraction of Selacholeic acid and application have great importance and are worth.Seen relevant introduction at present comprises from seaweed plant, shark oil shai and shark brain and extracting, but because the raw material problem, its cost is too high, is difficult to form large-scale production.
In order to solve the raw material problem, also mentioned in the relevant document and from plant, extracted Selacholeic acid, for example extracted as raw material, the deciduous tree that acer truncatum belongs to for the Aceraceae maple with acer truncatum, " Chinese Plants will " is named to " acer truncatum ", has another name called acer monoes.In recent years, to chemical ingredients, prospect in medicine, the physiology characteristic of acer truncatum seed, a series of research has been carried out in aspects such as pharmacy characteristic, its kind benevolence oil length 48%, detect 12 kinds of lipid acid altogether through identifying, wherein the Selacholeic acid content that relates to of present technique is 5~6%.Such preparation method is disclosed in number of patent application is 200510096369.8 file, it by saponification and low temperature urea embedding process, normal temperature vacuum distillation process, cryogenic freezing fractional crystallization process, methyl esterification of fatty acid and sepn process and selectivity a little less than the adsorption and purification process form.The problem of its existence is: complex steps, wash easy emulsification, product acid value height and the lower problem of product purity.
Summary of the invention:
The object of the present invention is to provide and a kind ofly from Acertruncatum Bunge oil, extract the method for Selacholeic acid, to overcome complex steps that prior art exists, to wash easy emulsification, product acid value height and the lower problem of product purity with molecular distillation technique.
In order to achieve the above object, the technical solution used in the present invention is: a kind ofly from Acertruncatum Bunge oil, extract the method for Selacholeic acid, comprise the steps successively with molecular distillation technique,
(1) preparation Acertruncatum Bunge oil;
(2) producing of Selacholeic acid ethyl ester: (1) pre-treatment: Acertruncatum Bunge oil is carried out depickling handle, remove oil foot and wash, slough moisture then; (2) ethyl esterization:, wash then, separate with carrying out esterification after Acertruncatum Bunge oil, dehydrated alcohol and the basic catalyst mixing; (3) molecular distillation: carry out molecular distillation under different vacuum conditions and temperature, product is collected in classification.
In the above-mentioned steps (two):
(1) pre-treatment: the acer truncatum crude oil is removed by filter impurity, the sodium hydroxide solution that adds Acertruncatum Bunge oil weight 0.5~1% according to the acid value of Acertruncatum Bunge oil carries out depickling to be handled, the concentration of sodium hydroxide solution is 4~8%, and reaction conditions is 30~50 ℃, stirring velocity 30~60r/min, time is 30~60min, be rapidly heated 80 ℃ according to 1 ℃/speed at one hour rating after reaction is finished, insulation was left standstill 3~8 hours, and neat soap is separated fully, remove oil foot and carry out washed several times with water, slough moisture then.
(2) ethyl esterization: carry out esterification after the basic catalyst of the dehydrated alcohol of the Acertruncatum Bunge oil of 100 weight parts and 40~60 weight parts and 1.0~1.5 weight parts mixed, reacted under 75~80 ℃ temperature 2~3 hours, the reaction after washing for several times.
Above-mentioned basic catalyst is sodium hydroxide or potassium hydroxide.
In the above-mentioned steps (two) (3): under different vacuum conditions and temperature, carry out six grades of molecule distillations, collect the fatty acids products of different carbon chain lengths and different degree of saturation, concrete parameter:
Progression | Vacuum tightness (pa) | Temperature (℃) | Remarks |
The first step | 500--1000 | 100-120 | Remove moisture, the degassing |
The second stage | 80--100 | 145-155 | Remove c14, c16, c18 fatty acid ester |
The third stage | 10--20 | 150-155 | Remove c20 and part c22 |
The fourth stage | 0.1--2 | 155-160 | Remove sterol, vitamin-E |
Level V | 0.1-2 | 145-150 | Remove c22 and part c24:0 |
The 6th grade | 0.1-2 | 148-153 | Obtain the above neural acid esters of 50% content |
Compared with prior art, advantage of the present invention is as follows:
1. step is simple: by grease is carried out pre-treatment, one step of esterification is finished; On the isolation technique of fatty-acid ethyl ester, the entrapping method that prior art adopted is relatively poor because of the selectivity to Selacholeic acid, so the purity of product is lower, present technique adopts molecular distillation method to separate the Selacholeic acid ethyl ester, according to the difference of various fatty-acid ethyl esters boiling point under differing temps and vacuum tightness and with the Selacholeic acid ethyl ester separate, enrichment, obtain content and be the Selacholeic acid ethyl ester more than 50%.
2, technology rationally, be easy to large-scale production: this technology is not used solvent, uses the separation method of physics fully, and is little to the product sex change, no coupling product; Apparatus operation method is easy simultaneously, easy handling, and can obtain the purity height, the product that quality is good, production cost is low is convenient to applying of suitability for industrialized production.
3, domestic research and development to the Acertruncatum Bunge oil product at present still is in the junior stage, Acertruncatum Bunge oil product as high added value, can convert ester of low-carbon alcohol to by triglyceride level, becoming the finished product as the Selacholeic acid ethyl ester emerges, the Selacholeic acid ethyl ester has the advantage of following several respects: be easy to absorption of human body, have no side effect; Boiling point is low, easier distillation and fractionation; Equipment is cheap and energy consumption is lower; Be convenient to packing and transportation.
Embodiment:
The present invention is a raw material with the acer truncatum seed, peels off, squeezes, makes Acertruncatum Bunge oil, carries out esterification with excess ethanol through pretreated Acertruncatum Bunge oil under the basic catalyst effect, makes the triglyceride level in the raw material be transformed into fatty-acid ethyl ester.Dewater after removing byproduct of reaction, again the croude fatty acids ethyl ester is repeatedly distilled under certain vacuum pressure and temperature, to obtain the Selacholeic acid ethyl ester product.
Among the present invention:
The esterification principle is: neutral oil in the raw material and excess ethyl alcohol are carried out transesterification reaction under the condition that basic catalyst exists, make neutral oil (triglyceride level) be transformed into fatty-acid ethyl ester.
The alkali refining principle is: free fatty acids and sodium hydroxide reaction generate soda soap and water, remove after precipitation and washing.
RCOOCH+N
aOH→RCOON
a+H
2O
The transesterification reaction formula:
To be described in detail the present invention by specific embodiment below.
Embodiment 1:
(1) producing of Acertruncatum Bunge oil:
(1) peels off: acer truncatum seed control moisture content in the 8-12% scope, is entered the processing of peeling off of the special-purpose decorticator of acer truncatum seed, obtain acer truncatum benevolence after through selection by winnowing shell benevolence being separated after the processing.
(2) oil expression: the acer truncatum benevolence after will peeling off, separating is carried out the moisture adjusting, and moisture content is controlled in the 8-10% scope, extracts oil with 90 type crushers, and oily yield is more than 85%.
(2) producing of Selacholeic acid ethyl ester:
(1) pre-treatment: the acer truncatum crude oil is removed by filter impurity, to add concentration be 5% sodium hydroxide solution by the alkali number that adds of Acertruncatum Bunge oil weight 0.8%, temperature of reaction is 50 ℃, stirring velocity 40r/min, the time is 30min, is rapidly heated 80 ℃ according to 1 ℃/speed at one hour rating after reaction is finished, insulation was left standstill 5 hours, neat soap is separated fully, remove oil foot and wash 3 times, slough moisture then.
(2) ethyl esterization: carry out esterification after the basic catalyst potassium hydroxide of the dehydrated alcohol of the Acertruncatum Bunge oil of 100 weight parts and 40 weight parts and 1.0 weight parts mixed, reaction is 2 hours under 75 ℃ temperature, reacted after washing 3 times, deglycerizin, alkali, and excess ethanol.
(3) molecular distillation: carry out six grades of molecule distillations under different vacuum conditions and temperature, collect the fatty-acid ethyl ester product of different carbon chain lengths and different degree of saturation, control condition and result are
Progression | Vacuum tightness (pa) | Temperature (℃) | Remarks |
The first step | 700 | 110 | Remove moisture, the degassing |
The second stage | 100 | 152-155 | Remove c14, c16, c18 fatty acid ester |
The third stage | 20 | 150-155 | Remove c20 and part c22 |
The fourth stage | 2 | 155-160 | Remove sterol, vitamin-E |
Level V | 2 | 145-150 | Remove c22 and part c24:0 |
The 6th grade | 2 | 148-153 | Obtain the above Selacholeic acid ethyl ester of 50% content |
Embodiment 2:
(1) producing of Acertruncatum Bunge oil: with embodiment 1.
(2) producing of Selacholeic acid ethyl ester:
(1) pre-treatment: the acer truncatum crude oil is removed by filter impurity, to add concentration be 4% sodium hydroxide solution by the alkali number that adds of Acertruncatum Bunge oil weight 1.0%, temperature of reaction is 40 ℃, stirring velocity 30r/min, the time is 60min, is rapidly heated 80 ℃ according to 1 ℃/speed at one hour rating after reaction is finished, insulation was left standstill 6 hours, neat soap is separated fully, remove oil foot and wash 3 times, slough moisture then.
(2) ethyl esterization: carry out esterification after the basic catalyst potassium hydroxide of the dehydrated alcohol of the Acertruncatum Bunge oil of 100 weight parts and 50 weight parts and 1.2 weight parts mixed, reaction is 2 hours under 75 ℃ temperature, reacted after washing 3 times, deglycerizin, alkali, and excess ethanol.
(3) molecular distillation: under different vacuum conditions and temperature, carry out six grades of molecule distillations, collect the fatty-acid ethyl ester product of different carbon chain lengths and different degree of saturation.Control condition and result are
Progression | Vacuum tightness (pa) | Temperature (℃) | Remarks |
The first step | 500 | 100-105 | Remove moisture, the degassing |
The second stage | 100 | 152-155 | Remove c14, c16, c18 fatty acid ester |
The third stage | 10 | 150-155 | Remove c20 and part c22 |
The fourth stage | 1 | 155-160 | Remove sterol, vitamin-E |
Level V | 1 | 145-150 | Remove c22 and part c24:0 |
The 6th grade | 0.5 | 148-153 | Obtain the above Selacholeic acid ethyl ester of 50% content |
Embodiment 3:
(1) producing of Acertruncatum Bunge oil: with embodiment 1.
(2) producing of Selacholeic acid ethyl ester:
(1) pre-treatment: the acer truncatum crude oil is removed by filter impurity, to add concentration be 6% sodium hydroxide solution by the alkali number that adds of Acertruncatum Bunge oil weight 0.5%, temperature of reaction is 30 ℃, stirring velocity 60r/min, the time is 60min, is rapidly heated 80 ℃ according to 1 ℃/speed at one hour rating after reaction is finished, insulation was left standstill 8 hours, neat soap is separated fully, remove oil foot and wash 2 times, slough moisture then.
(2) ethyl esterization: carry out esterification after the basic catalyst potassium hydroxide of the dehydrated alcohol of the Acertruncatum Bunge oil of 100 weight parts and 60 weight parts and 1.5 weight parts mixed, reaction is 3 hours under 80 ℃ temperature, reacted after washing 2 times, deglycerizin, alkali, and excess ethanol.
(3) molecular distillation: under different vacuum conditions and temperature, carry out six grades of molecule distillations, collect the fatty-acid ethyl ester product of different carbon chain lengths and different degree of saturation.Control condition and result are
Progression | Vacuum tightness (pa) | Temperature (℃) | Remarks |
The first step | 500 | 102 | Remove moisture, the degassing |
The second stage | 50 | 145-150 | Remove c14, c16, c18 fatty acid ester |
The third stage | 10 | 150-155 | Remove c20 and part c22 |
The fourth stage | 2 | 158-160 | Remove sterol, vitamin-E |
Level V | 0.5 | 145-150 | Remove c22 and part c24:0 |
The 6th grade | 0.5 | 148-153 | Obtain the above Selacholeic acid ethyl ester of 50% content |
。
Claims (4)
1, a kind ofly from Acertruncatum Bunge oil, extract the method for Selacholeic acid, comprise the steps successively with molecular distillation technique,
(1) preparation Acertruncatum Bunge oil;
(2) producing of Selacholeic acid ethyl ester: (1) pre-treatment: Acertruncatum Bunge oil is carried out depickling handle, remove oil foot and wash, slough moisture then; (2) ethyl esterization:, wash then, separate with carrying out esterification after Acertruncatum Bunge oil, dehydrated alcohol and the basic catalyst mixing; (3) molecular distillation: carry out molecular distillation under different vacuum conditions and temperature, product is collected in classification.
2, as claimed in claim 1ly a kind ofly from Acertruncatum Bunge oil, extract the method for Selacholeic acid, it is characterized in that with molecular distillation technique: in the described step (two),
(1) pre-treatment: the acer truncatum crude oil is removed by filter impurity, the sodium hydroxide solution that adds Acertruncatum Bunge oil weight 0.5~1% according to the acid value of Acertruncatum Bunge oil carries out depickling to be handled, the concentration of sodium hydroxide solution is 4~8%, and reaction conditions is 30~50 ℃, stirring velocity 30~60r/min, time is 30~60min, be rapidly heated 80 ℃ according to 1 ℃/speed at one hour rating after reaction is finished, insulation was left standstill 3~8 hours, and neat soap is separated fully, remove oil foot and carry out washed several times with water, slough moisture then.
(2) ethyl esterization: carry out esterification after the basic catalyst of the dehydrated alcohol of the Acertruncatum Bunge oil of 100 weight parts and 40~60 weight parts and 1.0~1.5 weight parts mixed, reacted under 75~80 ℃ temperature 2~3 hours, the reaction after washing for several times.
3, as claimed in claim 1 or 2ly a kind ofly extract the method for Selacholeic acid with molecular distillation technique from Acertruncatum Bunge oil, it is characterized in that: described basic catalyst is sodium hydroxide or potassium hydroxide.
4, a kind of method of from Acertruncatum Bunge oil, extracting Selacholeic acid with molecular distillation technique as claimed in claim 3, it is characterized in that: in the described step (two) (3): under different vacuum conditions and temperature, carry out six grades of molecule distillations, collect the fatty acids products of different carbon chain lengths and different degree of saturation, concrete parameter:
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CN101285000B (en) * | 2008-05-30 | 2011-04-13 | 云南百瑞特生物开发有限公司 | Process for preparing biodiesel and nervonic acid by using purpleblow maple oil as raw material |
CN101429112B (en) * | 2008-12-12 | 2011-08-31 | 中国科学院山西煤炭化学研究所 | Method for distillation separation of mixture of nervonic acid and erucic acid from acer truncatum oil |
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 |
CN101429217B (en) * | 2008-11-27 | 2012-11-28 | 中国科学院山西煤炭化学研究所 | Phospholipid type nervonic acid and method for producing the same |
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CN111735888A (en) * | 2020-08-14 | 2020-10-02 | 宝枫生物科技(北京)有限公司 | Biomarker for diagnosing onset of nervonic acid in acer truncatum seed oil and application of biomarker |
CN111735888B (en) * | 2020-08-14 | 2020-11-20 | 宝枫生物科技(北京)有限公司 | Biomarker for diagnosing onset of nervonic acid in acer truncatum seed oil and application of biomarker |
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