CN102452929A - Production process for preparing high-purity alpha-linolenic acid by taking perilla seeds as raw materials - Google Patents
Production process for preparing high-purity alpha-linolenic acid by taking perilla seeds as raw materials Download PDFInfo
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- CN102452929A CN102452929A CN2010105292050A CN201010529205A CN102452929A CN 102452929 A CN102452929 A CN 102452929A CN 2010105292050 A CN2010105292050 A CN 2010105292050A CN 201010529205 A CN201010529205 A CN 201010529205A CN 102452929 A CN102452929 A CN 102452929A
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Abstract
The invention relates to a production process for preparing high-purity alpha-linolenic acid by taking perilla seeds as raw materials. The production process is characterized in that: perilla oil is dissolved in an ethanol water solution to carry out saponification reaction so as to obtain mixed fatty acid, then the mixed fatty acid is subjected to urea inclusion, slow cooling treatment and evaporative concentration, and the concentrate is sequentially subjected to esterification and column chromatography separation. The process for preparing high-purity alpha-linolenic acid comprises preparation of mixed fatty acid, preparation of crude linolenic acid, preparation of alpha-methyl linolenate, purification of alpha-methyl linolenate, and preparation of alpha-linolenic acid. The production process comprises the following concrete steps of: mixing 9g alpha-methyl linolenate, 40ml of anhydrous ethanol and 1.4g of sodium hydroxide; stirring in nitrogen atmosphere for reacting for more than 10 hours; pouring into 100ml of water; extracting with petroleum ether; acidifying with hydrochloric acid in a ratio of 1:1; extracting again with petroleum ether for three times in nitrogen atmosphere; mixing petroleum ether extracts; washing with water; drying with anhydrous Na2SO4; evaporating for removing solvents to obtain 5.5g of flaxen alpha-linolenic acid of which the content is 99%; carrying out vacuum distillation by using a molecular distillation device; distilling out alpha-linolenic acid of which the content is 99% at 150-160 DEG C and 5mmHg to obtain alpha-linolenate of which the purity is more than 90%; and finally, carrying out saponification reaction and molecular distillation to obtain the colorless alpha-linolenic acid of which the purity is more than 95%. The production process provided by the invention has the advantages of high purity and low cost and is suitable for large-scale production.
Description
Technical field
The present invention relates to a kind of preparation method of industriallization unsaturated fatty acids, more specifically saying so a kind of is the production technique that raw material is produced high-purity alpha-linolenic acid with the perilla seed.
Background technology
Alpha-linolenic acid belongs to the serial unsaturated fatty acids of ω-3, is one of unsaturated fatty acids of needed by human, and human body self can not synthesize, and can only absorb from the external world.Alpha-linolenic acid can reduce hyperlipidemia and hypertension effectively, suppresses the formation of thromboxane, alleviates arteriosclerosis, prevents and treats cardiovascular disorder etc.; Can also suppress liver synthetic fatty acid and lipoprotein, change blood viscosity, vasodilation suppresses platelet aggregation; And have anticancer, anti-ageing, increase intelligence effect such as protection heart etc.In view of the importance of alpha-linolenic acid and the situation of human general insufficiency of intake, the special alpha-linolenic acid that replenishes of the World Health Organization and Food and Argriculture OrganizationFAO's suggestion.Alpha-linolenic acid acid land resources is very rare, and Purple Perilla Seed Oil is considered to be rich in the best raw material of alpha-linolenic acid, and its alpha-linolenic acid content is up to 50%～60%.The existence form of ethyl ester is stable than free acid, is convenient to scale operation and use.
Summary of the invention
The objective of the invention is to overcome the deficiency of prior art, improve, is the method for producing highly purified alpha-linolenic acid of raw material scale prodn with the perilla seed but provide a kind of.
Main technical schemes of the present invention: at first perilla oil is carried out saponification reaction, mixed fatty acid extracted, urea clathration again, concentrating and separating obtains the thick alpha-linolenic acid about 90%; It is the alpha-linolenic acid ester more than 95% that esterification then, column chromatography for separation, freezing and crystallizing obtain purity; At last linolenate is carried out saponification reaction, make alpha-linolenic acid, improve purity (reaching as high as 99%) through further short-path distillation again.
Preparing method of the present invention comprises following process:
1, oil expression and filtration: adopt mechanical cold pressing process to squeeze perilla oil perilla seed, the solid impurity in the perilla oil is leached.
2, saponification reaction: NaOH with 5～10% or KOH aqueous ethanolic solution and oleum lini mix, and 10～50 ℃ of saponification reactions 10～50 hours, saponification degree was not less than 85%.Thin up is acidified to acidity with dilute sulphuric acid again, isolates oil reservoir, and extraction agent extracts, and washing then, dry, filtration obtain mixed fatty acid.Described oleum lini and NaOH weight ratio are 1: 0.1～0.3, and the weight ratio of described ethanol and water is 100: 20～10: 80; Described extraction agent is organic extractant or inorganic extraction agent.
3. urea clathration: the mixed fatty acid of urea alcoholic solution with 10～30% and step (2) system dissolves until mixture under 50 ℃ fully; After dropping to 25 ℃, in 4～8 hours, make mixture slowly reduce to-10 ℃ again, separate out crystallization by 25 ℃; Filter then; Use the petroleum ether crystallization, evaporated filtrate reclaims solvent, gets the alpha-linolenic acid bullion.The weight ratio of described mixed fatty acid and urease solution is 1: 10～25; Described alcohol comprises methyl alcohol or ethanol, and alcohol is 1: 1.5～4 with the weight ratio of urea.
4. esterification treatment: pure and mild 0.5～0.2 weight part vitriol oil of 1 weight part alpha-linolenic acid bullion, 1～3 weight part is mixed; In 40～80 ℃ of esterifications 10～40 hours, after thin up, organic layer are washed twice with dilute NaOH solution again with twice of washing; Petroleum ether extraction then; Filter the back evaporation except that desolvating, underpressure distillation under 220～240t, 6mmHg obtains thick alpha-linolenic acid ester.Described alcohol comprises methyl alcohol or ethanol.
5. column chromatography for separation: the thick alpha-linolenic acid ester that step (4) is produced is dissolved in 60～80 ℃ of sherwood oils, with it through containing 6～20%AgNO
3The stainless steel pillar of silica gel (70～100 order), the length of pillar and diameter are respectively 30～50cm and 4～5cm, effluent is collected in the leacheate flushing, evaporation removes and desolvates, and obtains containing the α-flax field ester more than 99%.Separating the used leacheate of acid is sherwood oil and ETHYLE ACETATE mixed solution, and its volume ratio is 90: 10～50: 50, perhaps formic acid and water mixed liquid, and its volume ratio is 20: 80～70: 30; Dividing the used leacheate of high ester is sherwood oil, and column chromatography for separation is handled by ordinary method.
6. saponification is purified: alpha-linolenic acid ester 3 weight parts that step (5) is obtained and the ethanol of 0.2～0.3 weight part NaOH and 5～10 weight parts mix; Under the protection of inert gas; Stir saponification reaction adds 5～10 weight part sherwood oils and 20～30 weight parts after 5～24 hours water down in 30～75 ℃; Vibration, it is 4～5 that water layer uses Hydrogen chloride to be neutralized to PH under the inert gas protection, uses petroleum ether extraction again; Extraction liquid removes to desolvate through washing, drying, evaporation and obtains yellow solution, after short-path distillation promptly obtains water white alpha-linolenic acid.
Major advantage of the present invention: the present invention can increase to the purity of alpha-linolenic acid more than 95% by 90% owing to adopt alpha-linolenic acid bullion esterification pilot process; Because column chromatography is to adopt the higher mixed ester of alpha-linolenic acid ester content, adopts the silica filler post simultaneously again, can effectively alpha-linolenic acid ester and other separating substances be opened, and guarantees to obtain content at the alpha-linolenic acid fat more than 99%.Again through saponification reaction get final product highly purified alpha-linolenic acid; Crossing and going to chromatographic separation is that the laboratory obtains less pure chemical substance; And that method of the present invention has carried out improving to traditional column chromatography for separation technology is perfect, and efficient improves greatly, satisfies the suitability for industrialized production needs.In a word, the present invention has the advantage of purity height, low, the suitable large-scale production of cost.
Through embodiment the present invention is further specified below.
Embodiment
Instance 1:
This instance is produced highly purified alpha-linolenic acid, and to prepare process following:
(1) preparation of mixed fatty acid: in 10 liters of there-necked flasks, add perilla oil 1.25Kg, 185g sodium hydroxide and 5000ml absolute ethyl alcohol, mix, continue at stirring at room more than 6 hours.Be dissolved in reaction mixture in the 5 intensification water next day, under nitrogen protection, and with 1: 1 sulfuric acid acidation of 800ml, layering, organic layer is used hot water wash, gets mixed fatty acid with anhydrous sodium sulfate drying.
(2) preparation of hurds acid: in 10 liters of there-necked flasks; Add 95% ethanol 4500ml, urea 1250g and mixed fatty acid 500ml respectively; Mix to dissolving fully, the crystallization filtration is separated out in cooling step by step, uses the normal hexane wash crystallization; Evaporated filtrate removes and desolvates, and resistates is the linolenic acid bullion;
(3) preparation of alpha-linolenic acid methyl esters: in the 250ml there-necked flask, hurds acid 33g, methyl alcohol 5g and sulfuric acid 2ml are mixed, refluxing and stirring is reacted more than 6 hours; After reaction finishes; Add water towards rare, extract, washing, dry, filtration with sherwood oil (60～90 ℃); Evaporation removes and desolvates, and underpressure distillation gets weak yellow liquid.
(5) purifying process of alpha-linolenic acid methyl esters: the thick alpha-linolenic acid methyl esters of 12g is dissolved in a small amount of sherwood oil (30～60 ℃), contains Ag through a filling
+(70～100 order) silica gel pillar (50cm * 4m), collect the effluent evaporation remove desolvate 6g content at the alpha-linolenic acid methyl esters more than 99%, vacuum distilling gets colourless liquid, alpha-linolenic acid methyl esters content is more than 995%.
(6) preparation of alpha-linolenic acid: alpha-linolenic acid methyl esters 9g, absolute ethyl alcohol 40ml and sodium hydroxide 1.4g are mixed, and stirring reaction poured in the 100ml water more than 10 hours under nitrogen atmosphere; Use petroleum ether extraction, with 1: 1 hcl acidifying, under the nitrogen atmosphere; Use petroleum ether extraction again three times; Merge petroleum ether extraction liquid, clean to wash, use anhydrous Na
2SO
4Drying, evaporation removes and desolvates, and gets faint yellow alpha-linolenic acid 5.5g, and content is 99%.Utilize molecular distillation apparatus to carry out vacuum distilling, alpha-linolenic acid is steamed under 150～160 ℃, 5mmHg, and content reaches 99%.
Instance 2:
Get 0.1 liter of oleum lini, 95% ethanol 5000ml, water 500ml, NaOH 35g under 50 ℃-60 ℃, reacted 20 hours, pressed instance 1 treatment condition then, got mixed fatty acid 60ml.
Get 95% methyl alcohol 400ml, the mixed fatty acid 60ml of urea 120g and above-mentioned preparation, according to 1 of instance to same procedure handle 25ml alpha-linolenic acid bullion, content is 90%.
Alpha-linolenic acid bullion 25ml and ethanol 60g are mixed, add the dense H of 1.0ml
2SO
4, refluxing and stirring reaction 40 hours, reaction finishes.According to instance 1 method handle Alpha-ethyl linolenate 20ml, content 96.5%.
Above-mentioned Alpha-ethyl linolenate and NaOH ethanol 80ml (containing 2.8g NaOH) are mixed, according to instance 1 method handle alpha-linolenic acid 16ml, content 96.9%.
Instance 3:
Get by instance 1 prepared Alpha-ethyl linolenate and be used for following step:
With 20%AgNO
3Silica gel 300g (about 200 orders) is filled in 45cm * 3.5cm (id) stainless steel tube; Upper ends Alpha-ethyl linolenate 10g; With the petroleum acid is that leacheate is collected the 3rd component, and evaporation gets Alpha-ethyl linolenate 8g, content 99.5% after eliminating solvent; With its according to instance 1 final step handle alpha-linolenic acid 7g, content 99.5%.
Claims (5)
1. one kind is the production technique that raw material is produced high-purity alpha-linolenic acid with the perilla seed, and it is characterized in that: the preparation process may further comprise the steps:
(1) adopts mechanical cold pressing process to squeeze perilla oil perilla seed, the solid impurity in the perilla oil is leached.
(2) 5～10% NaOH or KOH aqueous ethanolic solution and oleum lini are mixed, 10～50 ℃ of saponification reactions 10～50 hours, saponification degree was not less than 85%.Thin up is acidified to acidity with dilute sulphuric acid again, isolates oil reservoir, and extraction agent extracts, and washing then, dry, filtration obtain mixed fatty acid.Described oleum lini and NaOH weight ratio are 1: 0.1～0.3, and the weight ratio of described ethanol and water is 100: 20～10: 80.
(3) mixed fatty acid with 10～30% urea alcoholic solution and step (2) system dissolves until mixture under 50 ℃ fully; After dropping to 25 ℃, in 4～8 hours, make mixture slowly reduce to-10 ℃ again, separate out crystallization by 25 ℃; Filter then; Use the petroleum ether crystallization, evaporated filtrate reclaims solvent, gets the alpha-linolenic acid bullion.The weight ratio of described mixed fatty acid and urease solution is 1: 10～25; Described alcohol comprises methyl alcohol or ethanol, and alcohol is 1: 1.5～4 with the weight ratio of urea.
(4) the 1 weight part alpha-linolenic acid bullion of step (3) being produced, pure and mild 0.5～0.2 weight part vitriol oil of 1～3 weight part mix; In 40～80 ℃ of esterifications 10～40 hours, after thin up, organic layer are washed twice with dilute NaOH solution again with twice of washing; Petroleum ether extraction then; Filter the back evaporation except that desolvating, underpressure distillation under 220～240t, 6mmHg obtains thick alpha-linolenic acid ester.Described alcohol comprises methyl alcohol or ethanol.
(5) the thick alpha-linolenic acid ester of step (4) being produced is dissolved in 60～80 ℃ of sherwood oils, with it through containing 6～20%AgNO
3The stainless steel pillar of silica gel (70～100 order), the length of pillar and diameter are respectively 30～50cm and 4～5cm, effluent is collected in the leacheate flushing, evaporation removes and desolvates, and obtains containing the α-flax field ester more than 99%.Separating the used leacheate of acid is sherwood oil and ETHYLE ACETATE mixed solution, and its volume ratio is 90: 10～50: 50, perhaps formic acid and water mixed liquid, and its volume ratio is 20: 80～70: 30; Dividing the used leacheate of high ester is sherwood oil, and column chromatography for separation is handled by ordinary method.
(6) alpha-linolenic acid ester 3 weight parts that step (5) obtained and the ethanol of 0.2～0.3 weight part NaOH and 5～10 weight parts mix; Under the protection of inert gas; Stir saponification reaction adds 5～10 weight part sherwood oils and 20～30 weight parts after 5～24 hours water down in 30～75 ℃; Vibration, it is 4～5 that water layer uses Hydrogen chloride to be neutralized to PH under the inert gas protection, uses petroleum ether extraction again; Extraction liquid removes to desolvate through washing, drying, evaporation and obtains yellow solution, after short-path distillation promptly obtains water white alpha-linolenic acid.
According to claim 1 described a kind of be the production technique that raw material is produced high-purity alpha-linolenic acid with the perilla seed, it is characterized in that: the described extraction agent of step (2): organic extractant comprises sherwood oil, inorganic extraction agent is the 5～15%NaOH or the KOH aqueous solution.
According to claim 1 described a kind of be the production technique that raw material is produced high-purity alpha-linolenic acid with the perilla seed, it is characterized in that: the described alcohol of step (3) comprises methyl alcohol, ethanol or Virahol, alcohol and the weight ratio of urea are for being 1: 1.5～4.
According to claim 1 described a kind of be the production technique that raw material is produced high-purity alpha-linolenic acid with the perilla seed, it is characterized in that: the described alcohol of step (4) comprises methyl alcohol, ethanol.
5. according to the described method of claim 1, it is characterized in that: (5 described leacheates: the leacheate that separates acid is that the volume ratio of sherwood oil and ETHYLE ACETATE is that the volume ratio of 90: 10～50: 50 mixed solution or first alcohol and water is 20: 80～70: 30 a mixed solution to step; Separating the used leacheate of ester is sherwood oil.
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102978009A (en) * | 2012-11-26 | 2013-03-20 | 安徽亿源生物工程有限公司 | Preparation method of linseed oil |
| CN103238845A (en) * | 2013-05-31 | 2013-08-14 | 烟台燕园科玛生物技术开发有限公司 | Health food for strengthening brain and improving intelligence |
| CN104046508A (en) * | 2014-06-17 | 2014-09-17 | 李传印 | Purification device and purification process for unsaturated fatty acids in peanuts |
| CN104418726A (en) * | 2013-08-20 | 2015-03-18 | 陕西中鼎华盛农业发展有限公司 | Extraction method of [alpha]-linolenic acid |
| CN104725216A (en) * | 2015-02-12 | 2015-06-24 | 湖北华龙生物制药有限公司 | Method for purifying and separating high-purity alpha-linolenic acid and linoleic acid from Chinese tallow kernel oil |
| CN105567435A (en) * | 2016-01-13 | 2016-05-11 | 安阳工学院 | Base catalysis perilla oil ethyl esterification reaction process |
| CN105753689A (en) * | 2016-03-15 | 2016-07-13 | 宁夏大学 | Method of extracting purified Alpha-linolenic acid from linseed oil |
| CN106496021A (en) * | 2016-10-24 | 2017-03-15 | 烟台燕园科玛健康产业有限公司 | A kind of high-purity alpha linolenic acid separating technology |
| CN107523424A (en) * | 2017-10-16 | 2017-12-29 | 西南林业大学 | A kind of method of amino-compound inclusion method separation unrighted acid |
| CN108325581A (en) * | 2018-02-07 | 2018-07-27 | 中国农业机械化科学研究院 | A kind of comprehensive utilization process of linseed |
| CN108611188A (en) * | 2016-12-09 | 2018-10-02 | 丰益(上海)生物技术研发中心有限公司 | A kind of grease processing technique |
| CN112159320A (en) * | 2020-09-25 | 2021-01-01 | 菏泽中禾健元生物科技有限公司 | Production method of high-purity linolenic acid |
| CN113413342A (en) * | 2021-06-25 | 2021-09-21 | 西南林业大学 | Method for extracting palmitoleic acid from macadamia nut and application of palmitoleic acid |
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2010
- 2010-11-03 CN CN2010105292050A patent/CN102452929A/en active Pending
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102978009A (en) * | 2012-11-26 | 2013-03-20 | 安徽亿源生物工程有限公司 | Preparation method of linseed oil |
| CN102978009B (en) * | 2012-11-26 | 2013-11-06 | 安徽亿源生物工程有限公司 | Preparation method of linseed oil |
| CN103238845A (en) * | 2013-05-31 | 2013-08-14 | 烟台燕园科玛生物技术开发有限公司 | Health food for strengthening brain and improving intelligence |
| CN104418726A (en) * | 2013-08-20 | 2015-03-18 | 陕西中鼎华盛农业发展有限公司 | Extraction method of [alpha]-linolenic acid |
| CN104046508A (en) * | 2014-06-17 | 2014-09-17 | 李传印 | Purification device and purification process for unsaturated fatty acids in peanuts |
| CN104725216A (en) * | 2015-02-12 | 2015-06-24 | 湖北华龙生物制药有限公司 | Method for purifying and separating high-purity alpha-linolenic acid and linoleic acid from Chinese tallow kernel oil |
| CN105567435A (en) * | 2016-01-13 | 2016-05-11 | 安阳工学院 | Base catalysis perilla oil ethyl esterification reaction process |
| CN105753689B (en) * | 2016-03-15 | 2020-02-07 | 宁夏大学 | Method for extracting and purifying α -linolenic acid from linseed oil |
| CN105753689A (en) * | 2016-03-15 | 2016-07-13 | 宁夏大学 | Method of extracting purified Alpha-linolenic acid from linseed oil |
| CN106496021A (en) * | 2016-10-24 | 2017-03-15 | 烟台燕园科玛健康产业有限公司 | A kind of high-purity alpha linolenic acid separating technology |
| CN108611188A (en) * | 2016-12-09 | 2018-10-02 | 丰益(上海)生物技术研发中心有限公司 | A kind of grease processing technique |
| CN107523424A (en) * | 2017-10-16 | 2017-12-29 | 西南林业大学 | A kind of method of amino-compound inclusion method separation unrighted acid |
| CN108325581A (en) * | 2018-02-07 | 2018-07-27 | 中国农业机械化科学研究院 | A kind of comprehensive utilization process of linseed |
| CN112159320A (en) * | 2020-09-25 | 2021-01-01 | 菏泽中禾健元生物科技有限公司 | Production method of high-purity linolenic acid |
| CN112159320B (en) * | 2020-09-25 | 2022-05-20 | 菏泽中禾健元生物科技有限公司 | Method for producing linolenic acid |
| CN113413342A (en) * | 2021-06-25 | 2021-09-21 | 西南林业大学 | Method for extracting palmitoleic acid from macadamia nut and application of palmitoleic acid |
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Application publication date: 20120516 |