CN101880601A - Method for preparing linoleic acid from idesia polycarpa Maxium. Var. vestita Diels oil - Google Patents
Method for preparing linoleic acid from idesia polycarpa Maxium. Var. vestita Diels oil Download PDFInfo
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- CN101880601A CN101880601A CN 201010209465 CN201010209465A CN101880601A CN 101880601 A CN101880601 A CN 101880601A CN 201010209465 CN201010209465 CN 201010209465 CN 201010209465 A CN201010209465 A CN 201010209465A CN 101880601 A CN101880601 A CN 101880601A
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Abstract
The invention discloses a method for preparing linoleic acid from idesia polycarpa Maxium. Var. vestita Diels oil, which belongs to the fields of medicaments, food and feed. A technique comprises degumming of crude oil by an acid method, preparation of mixed fatty acid and extraction of the linoleic acid. The method is characterized in that: degummed oil is obtained by an acidic degumming method, so phospholipid is removed completely; direct soap treatment is adopted to reserve the free linoleic acid and avoid the yield loss and the process is optimized to avoid the utilization of a toxic reagent, so the linoleic acid with high quality and high conversion rate is obtained at last; at the same time, the process has a simple process and low requirement on equipment and the solvent can be effectively reclaimed, so the cost is obviously reduced; and therefore, the method has a wide application prospect in the production of the high-quality linoleic acid.
Description
Technical field
The invention belongs to that to relate to a kind of be the linoleic method of raw material production with Idesia polycarpa oil.
Background technology
China has 4,000,000,000 mu in low quality, barren hill, beach etc. at present approximately, if make full use of, plant some high yields, cash crop that economic worth is high, not only can improve the ecological environment, increase economic benefit, can also alleviate the nervous relatively situation of China's cultivated land resource to a certain extent.Idesia polycarpa is the distinctive woody oleiferous plants plant variety of China, have widely distributed, less demanding to soil, weather etc., the characteristics that adaptability is stronger.Can be used for replacing good farmland crop production high value added product, not account for cultivated area, can really accomplish " do not strive grain, do not strive ground, do not strive profit, enlarge new resources " with traditional industries with grain with the people.Its product linolic acid, as staple commodities, added value of industry height has very big using value potentiality to be exploited.
Present linoleic research all concentrates on Thistle oil, Semen Maydis oil, cotton oil, soya-bean oil and sunflower wet goods vegetable oil.Will obtain these starting material in a large number, need take a large amount of valuable arable lands, production cost is also than higher.Therefore, select which kind of is suitable, vegetable oil resource comes develop actively and produces linolic acid cheaply, is one of key that needs to be resolved hurrily at present.Existing studies show that, Idesia polycarpa reaches four, 50 years the period of growth of the crop, and fruit oil length height, individual plant produce oil five, 60 jin, especially its oil is rich in linolic acid, up to 68～80%, be more than the twice of soya-bean oil content, can match in excellence or beauty with Thistle oil, but comprehensive cost be well below Thistle oil, be a kind of ideal oil crops, especially be fit to be used for the linolic acid of production high added value.
Studies show that in a large number linolic acid mainly shows the effect of human body: softening cardiovascular and cerebrovascular, blood fat-reducing blood pressure-decreasing promotes the new city metabolism, endocrine regulation.Linolic acid also has synthetic ARA, antitumor, anti-oxidant, reducing cholesterol, triglyceride level, low-density lipoprotein, atherosclerosis, raising immunizing power, improves skeleton density, increases effects such as muscle.Along with to the going deep into of linolic acid understanding, its demand is also increased year by year, the exploitation high purity, linolic acid has great importance cheaply.
It is to be raw material at Idesia polycarpa oil that this linolic acid prepares patent, explore a kind of efficiently, cheaply linolic acid extract, the novel process of purifying.
Summary of the invention
The objective of the invention is to utilize the linoleic method of Idesia polycarpa oil preparation.This method is utilized Idesia polycarpa oil preparation linolic acid, has higher linolic acid yield and sample purity, and low for equipment requirements, technology can be operated by force, and is with low cost, is fit to large-scale production.
The present invention is realized by following technical proposals.This scheme mainly comprises degumming raw oil, mixed fatty acid acid preparation, linolic acid separation and Extraction.It is characterized in that:
1. utilize the phosphatide in the sour method for degumming removal crude oil, contain some nonhydratable phosphatide in the crude oil, under strong acid condition, can be dissociated into hydrated phospholipid, change aqueous phase over to, thereby it is removed from crude oil;
2. under nitrogen protection, with degummed oil, an amount of alkali and the aqueous solution of low-boiling point alcohol, high temperature reflux, with the unsaponified glycerin fatty acid ester of organic solvent extraction, obtain fully saponified mixing-in fat hydrochlorate, handle with an amount of dilute acid soln subsequently, organic solvent extraction obtains mixed fatty acid behind the desolventizing;
3. mixed fatty acid is extracted linolic acid by urea adduct method, mix at a certain temperature with an amount of urea with the low-boiling point alcohol aqueous solution, add quantitative mixed fatty acid, high temperature reflux is after for some time, crystallisation by cooling, filtration, acidifying, and use organic solvent extraction, reclaim organic solvent and inorganic pure and mild urea in mutually then respectively, obtain high-purity linolic acid;
The used siccative of above-mentioned drying treatment can be molecular sieve, anhydrous sodium sulphate, anhydrous magnesium sulfate;
The used organic solvent of above-mentioned extraction treatment can be sherwood oil, normal heptane, normal hexane, ether, acetone;
Used low-boiling point alcohol can be methyl alcohol, ethanol, propyl alcohol in the above-mentioned treating processes; Alkali can be sodium hydroxide, potassium hydroxide; Acid comprises sulfuric acid, hydrochloric acid, phosphoric acid, citric acid etc.
Above-mentioned suitable condition is: treating processes nitrogen whole process protection; Sour add-on is that oil weighs 0.25% in the degumming raw oil, and treatment temp is 70 ℃, and alkali concn is 0.2mol/L, and usually time is 50 minutes; The temperature of mixed fatty acid preparation is controlled in 60～90 ℃ of scopes, and in 2～7 hours reaction times, the mole proportioning of grease and alkali is 1: 3～1: 4, and the volume ratio of alcohol solution and lipid acid is between 1～4 times; Urea clathration extracts in the linolic acid process, the mass ratio of mixed fatty acid, urea, alcohol and water is 1: (0.5～5): (2-10): (0.1～0.5), inclusion temperature are 50～90 ℃, and return time is 20～60 minutes, after inclusion is finished, preserved 5～36 hours down at low temperature (5～25 ℃).
Linolic acid preparation method provided by the invention has following remarkable advantage: utilize Idesia polycarpa oil can obtain high-quality linolic acid for raw material, cost is low, and the easy economy of preparation process is workable, and is not high to equipment requirements; Solvent for use is nontoxic, and the product of producing is suitable for application such as medicine, healthcare products, and major part can recycling, economic environmental protection; Preparation is the result show, linolic acid yield and purity height, and the enterprise that is fit to different scales produces, and has the good application and the market requirement.
Below to the detailed description of the invention:
Gordian technique of the present invention have following some: the one, in the process of coming unstuck, the addition of diluted alkaline not too much, excess base forms soap, can cause the neutral oil loss; The 2nd, in the treating processes, acid solutions is not too high, handles and wants gentle, otherwise can lose some active more intense linolic acid; The 3rd, mixed fatty acid preparation, linolic acid extract and finish, and after the oily water separation for the first time, water continues acidifying with the higher acid of concentration, and organic solvent extraction is avoided the linolic acid loss as far as possible.
Embodiment
Following example will give further instruction to method provided by the invention.
Embodiment 1
One, Idesia polycarpa degumming of oil
Under the nitrogen protection; 100 gram crude oils are preheating to 70 ℃, add the phosphoric acid of 0.25 gram, after fully stirring; add diluted alkaline to system pH less than 7; continue to stir 30 minutes, leave standstill insulation 20 minutes, reduce to room temperature then; 4500 rev/mins of high speed centrifugations of whizzer 15 minutes; divide to fall water layer, after measured, obtain the degummed oil that phosphorus content is lower than 0.4ppm.
Two, mixed fatty acid preparation
With the 100g degummed oil; 20 gram potassium hydroxide; 90 milliliters of ethanol and 25 ml waters mix; under the nitrogen protection; be stirred and heated to 60 ℃; refluxed 7 hours, after grease is fully saponified, cooling; fall unreacted grease with 20 milliliters of petroleum ether extractions; saponification resultant is acidified to system pH less than 2 with dilute sulphuric acid, separates oil reservoir, and water layer continues to use the sulphuric acid soln acidifying; add 50 milliliters of petroleum ether extractions; extraction liquid and oil reservoir merge, and are washed till neutrality with distilled water, behind the separation precipitation; add the anhydrous sodium sulphate dried overnight; filter, obtain mixed fatty acid, the degummed oil percent hydrolysis reaches 98.2% after testing.Rotary Evaporators reclaims the ethanol of aqueous phase and the sherwood oil in the oil phase respectively.
Three, linolic acid extracts
Get 300 gram urea, 600 milliliters of ethanol and 40 ml distilled waters and mix, be stirred and heated to 50 ℃ of backflows, treat that urea no longer dissolves after, add 100 gram mixed fatty acids, continued stirring and refluxing 60 minutes, cooling.Preserved 5 hours down at-5 ℃ then.After the taking-up, the explosive decompression suction filtration, reclaim urea, suction filtration liquid changes in the separating funnel, add dilute hydrochloric acid, till system pH is 2, add 100 milliliters of petroleum ether extractions, the dilute sulphuric acid acidifying of water after the separation, add 50 milliliters of petroleum ether extractions, the oil phase after the extraction merges with the oil phase of initial extraction, shows neutral with distilled water wash until solution, separating funnel separates, sherwood oil and ethanol reclaim by Rotary Evaporators, and oil phase anhydrous sodium sulphate dried overnight is filtered, get yield 89.5%, the linolic acid of purity 95.1%.
Embodiment 2
One, the Idesia polycarpa degumming of oil is identical with step 1 among the embodiment 1.
Two, the preparation of mixing acid
Get 100g degummed oil, 25 gram potassium hydroxide, 200 milliliters of ethanol and 10 ml distilled waters and mix, under the nitrogen protection, be stirred and heated to 90 ℃, refluxed 2 hours, after grease is fully saponified, cool off.The treating processes and the solvent recuperation that are prepared mixing acid by saponification resultant are identical with step 2 among the embodiment 1.The percent hydrolysis of degummed oil reaches 99.5% after testing.
Three, linolic acid extracts identical with step 3 among the embodiment 1.
After testing, the linolic acid yield is 90.4%, purity 94.5%.
Embodiment 3
One, the Idesia polycarpa degumming of oil is identical with step 1 among the embodiment 1.
Two, the preparation of mixing acid
Get 100g degummed oil, 25 gram potassium hydroxide, 200 milliliters of ethanol and 10 ml distilled waters and mix, under the nitrogen protection, be stirred and heated to 80 ℃, refluxed 4 hours, after grease is fully saponified, cool off.The treating processes and the solvent recuperation that are prepared mixing acid by saponification resultant are identical with step 2 among the embodiment 1.The percent hydrolysis of degummed oil reaches 98.7% after testing.
Three, linolic acid extracts identical with step 3 among the embodiment 1.
After testing, the linolic acid yield is 90.6%, purity 95.0%.
Embodiment 4
One, the Idesia polycarpa degumming of oil is identical with step 1 among the embodiment 1.
Two, the preparation of mixing acid
Get 100g degummed oil, 30 gram potassium hydroxide, 400 milliliters of ethanol mixing, under the nitrogen protection, be stirred and heated to 60 ℃, refluxed 7 hours, after grease is fully saponified, cooling.The treating processes and the solvent recuperation that are prepared mixing acid by saponification resultant are identical with step 2 among the embodiment 1.The percent hydrolysis of degummed oil reaches 97.9% after testing.
Three, linolic acid extracts identical with step 3 among the embodiment 1.
After testing, the linolic acid yield is 88.9%, purity 95.2%.
Embodiment 5
One, the Idesia polycarpa degumming of oil is identical with step 1 among the embodiment 1.
Two, the preparation of mixing acid
Get 100g degummed oil, 20 gram potassium hydroxide, 400 milliliters of ethanol mixing, under the nitrogen protection, be stirred and heated to 60 ℃, refluxed 7 hours, after grease is fully saponified, cooling.The treating processes and the solvent recuperation that are prepared mixing acid by saponification resultant are identical with step 2 among the embodiment 1.The percent hydrolysis of degummed oil reaches 97.2% after testing.
Three, linolic acid extracts identical with step 3 among the embodiment 1.
After testing, the linolic acid yield is 90.1%, purity 94.9%.
Embodiment 6
One, the Idesia polycarpa degumming of oil is identical with step 1 among the embodiment 1.
Two, the mixed fatty acid preparation is identical with step 2 among the embodiment 1.
After testing, the degummed oil percent hydrolysis is 97.8%.
Three, linolic acid extracts
Get 300 gram urea, 1500 milliliters of ethanol mix, and are stirred and heated to 90 ℃ of backflows, treat that urea no longer dissolves after, add 100 gram mixed fatty acids, continued stirring and refluxing 20 minutes, cooling.Preserved 36 hours down at 25 ℃ then.Remaining operation is identical with step 3 among the embodiment 1, gets yield 98.8%, the linolic acid of purity 90.0% at last.
Embodiment 7
One, the Idesia polycarpa degumming of oil is identical with step 1 among the embodiment 1.
Two, the mixed fatty acid preparation is identical with step 2 among the embodiment 1.
After testing, the degummed oil percent hydrolysis is 98.6%.
Three, linolic acid extracts
Get 300 gram urea, 1500 milliliters of ethanol mix, and are stirred and heated to 90 ℃ of backflows, treat that urea no longer dissolves after, add 100 gram mixed fatty acids, continued stirring and refluxing 20 minutes, cooling.Preserved 24 hours down at 15 ℃ then.Remaining operation is identical with step 3 among the embodiment 1, gets yield 98.1%, the linolic acid of purity 90.5% at last.
Embodiment 8
One, the Idesia polycarpa degumming of oil is identical with step 1 among the embodiment 1.
Two, the mixed fatty acid preparation is identical with step 2 among the embodiment 1.
After testing, the degummed oil percent hydrolysis is 98.9%.
Three, linolic acid extracts
Get 300 gram urea, 1500 milliliters of ethanol mix, and are stirred and heated to 90 ℃ of backflows, treat that urea no longer dissolves after, add 100 gram mixed fatty acids, continued stirring and refluxing 20 minutes, cooling.Preserved 10 hours down at 5 ℃ then.Remaining operation is identical with step 3 among the embodiment 1, gets yield 97.5%, the linolic acid of purity 91.5% at last.
Embodiment 9
One, the Idesia polycarpa degumming of oil is identical with step 1 among the embodiment 1.
Two, the mixed fatty acid preparation is identical with step 2 among the embodiment 1.
After testing, the degummed oil percent hydrolysis is 98.5%.
Three, linolic acid extracts
Get 300 gram urea, 1500 milliliters of ethanol mix, and are stirred and heated to 90 ℃ of backflows, treat that urea no longer dissolves after, add 100 gram mixed fatty acids, continued stirring and refluxing 20 minutes, cooling.Remaining operation is identical with step 3 among the embodiment 1, gets yield 96.9%, the linolic acid of purity 92.8% at last.
Embodiment 10
One, the Idesia polycarpa degumming of oil is identical with step 1 among the embodiment 1.
Two, the mixed fatty acid preparation is identical with step 2 among the embodiment 1.
After testing, the degummed oil percent hydrolysis is 98.3%.
Three, linolic acid extracts
Get 300 gram urea, 1500 milliliters of ethanol mix, and are stirred and heated to 70 ℃ of backflows, treat that urea no longer dissolves after, add 100 gram mixed fatty acids, continued stirring and refluxing 40 minutes, cooling.Remaining operation is identical with step 3 among the embodiment 1, gets yield 96.2%, the linolic acid of purity 92.1% at last.
Embodiment 11
One, the Idesia polycarpa degumming of oil is identical with step 1 among the embodiment 1.
Two, the mixed fatty acid preparation is identical with step 2 among the embodiment 1.
After testing, the degummed oil percent hydrolysis is 97.8%.
Three, linolic acid extracts
Get 300 gram urea, 2500 milliliters of ethanol mix, and are stirred and heated to 50 ℃ of backflows, treat that urea no longer dissolves after, add 100 gram mixed fatty acids, continued stirring and refluxing 60 minutes, cooling.Remaining operation is identical with step 3 among the embodiment 1, gets yield 95.3%, the linolic acid of purity 93.7% at last.
Embodiment 12
One, the Idesia polycarpa degumming of oil is identical with step 1 among the embodiment 1.
Two, the mixed fatty acid preparation is identical with step 2 among the embodiment 1.
After testing, the degummed oil percent hydrolysis is 99.7%.
Three, linolic acid extracts
Get 300 gram urea, 1500 milliliters of ethanol and 10 ml waters and mix, be stirred and heated to 50 ℃ of backflows,
After treating that urea no longer dissolves, add 100 gram mixed fatty acids, continued stirring and refluxing 60 minutes, cooling.
Remaining operation is identical with step 3 among the embodiment 1, gets yield 93.5%, the linolic acid of purity 94.9% at last.
Embodiment 13
One, the Idesia polycarpa degumming of oil is identical with step 1 among the embodiment 1.
Two, the mixed fatty acid preparation is identical with step 2 among the embodiment 1.
After testing, the degummed oil percent hydrolysis is 98.4%.
Three, linolic acid extracts identical with step 3 among the embodiment 1.
After testing, the linolic acid yield is 92.4%, purity 95.5%.
Embodiment 14
One, the Idesia polycarpa degumming of oil is identical with step 1 among the embodiment 1.
Two, the mixed fatty acid preparation is identical with step 2 among the embodiment 1.
After testing, the degummed oil percent hydrolysis is 98.1%.
Three, linolic acid extracts identical with step 3 among the embodiment 1.
After testing, the linolic acid yield is 91.8%, purity 96.7%.
Embodiment 15
One, the Idesia polycarpa degumming of oil is identical with step 1 among the embodiment 1.
Two, the mixed fatty acid preparation is identical with step 2 among the embodiment 1.
After testing, the degummed oil percent hydrolysis is 97.6%.
Three, linolic acid extracts identical with step 3 among the embodiment 1.
After testing, the linolic acid yield is 92.3%, purity 96.5%.
Embodiment 16
One, the Idesia polycarpa degumming of oil is identical with step 1 among the embodiment 1.
Two, the mixed fatty acid preparation is identical with step 2 among the embodiment 1.
After testing, the degummed oil percent hydrolysis is 96.9%.
Three, linolic acid extracts identical with step 3 among the embodiment 1.
After testing, the linolic acid yield is 93.3%, purity 96.1%.
Embodiment 17
One, the Idesia polycarpa degumming of oil is identical with step 1 among the embodiment 1.
Two, the mixed fatty acid preparation is identical with step 2 among the embodiment 1.
After testing, the degummed oil percent hydrolysis is 97.5%.
Three, linolic acid extracts identical with step 3 among the embodiment 1.
After testing, the linolic acid yield is 92.1%, purity 96.5%.
Embodiment 18
One, the Idesia polycarpa degumming of oil is identical with step 1 among the embodiment 1.
Two, the mixed fatty acid preparation is identical with step 2 among the embodiment 1.
After testing, the degummed oil percent hydrolysis is 97.9%.
Three, linolic acid extracts identical with step 3 among the embodiment 1.
After testing, the linolic acid yield is 93.2%, purity 97.4%.
Claims (4)
1. a linoleic preparation method is characterized in that utilizing Idesia polycarpa oil to prepare linolic acid for basic raw material, and preparation process comprises:
(1) crude oil comes unstuck by acid system, obtains sloughing the degummed oil of phosphatide;
(2) under the nitrogen protection,, obtain mixed fatty acid with degummed oil saponification, acidification;
(3) mixed fatty acid is extracted linolic acid by the urea saturation method.
2. according to the method for degumming raw oil described in claim 1 step (1), it is characterized in that, utilize acid system to come unstuck, under 70 ℃ of temperature, sour addition is that oil is heavy by 0.25%, and with the diluted alkaline neutralization, high speed centrifugation obtains degummed oil subsequently.
3. according to mixing acid preparation method in claim 1 step (2); it is characterized in that; under the nitrogen protection; degummed oil is directly mixed with the alcohol of 1～4 times of grease volume with the doubly normal alkali of 3-4; add suitable quantity of water alkali is dissolved in the alcoholic solution fully, in 60～90 ℃ of scopes, refluxed 2～7 hours; add strong acid in the solution subsequently; make system pH reduce to 2, separate oil reservoir, water layer continues acidifying; use an amount of organic solvent extraction; extraction liquid merges with the reservation oil reservoir, is washed with distilled water to neutrality, collects oil phase; precipitation obtains mixed fatty acid.
4. according to linolic acid extracting method in claim 1 step (3), it is characterized in that, with mixed fatty acid in being dissolved with the alcohol solution of saturated urea, in 50～90 ℃ of scopes, refluxed 20～60 minutes, preserved 5～36 hours down at-5～25 ℃ subsequently, filtering separation, according to the acidification of claim 3, the siccative dried overnight obtains linolic acid.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102229593A (en) * | 2011-07-25 | 2011-11-02 | 四川省毛叶山桐子科技股份有限公司 | Method for preparing natural vitamin E from crude oil of Maoyeshan tung tree seed |
| CN104177246A (en) * | 2014-08-06 | 2014-12-03 | 陈存武 | Method for preparing conjugated linoleic acid by using rhus chinensis oil |
| RU2572788C1 (en) * | 2015-02-17 | 2016-01-20 | Федеральное государственное бюджетное учреждение "Российский кардиологический научно-производственный комплекс" Министерства здравоохранения Российской Федерации (ФГБУ "РКНПК" Минздрава России) | Method for obtaining linoleic acid |
| CN105273848A (en) * | 2014-07-04 | 2016-01-27 | 漳州开发区欧中农业技术研发有限公司 | Method for extracting linoleic acid in citrus seed |
| CN105837430A (en) * | 2016-05-04 | 2016-08-10 | 罗江县德金种植协会 | Method for extracting linoleic acid from idesia polycarpa crude oil |
| CN106497675A (en) * | 2016-11-16 | 2017-03-15 | 四川省林业科学研究院 | A kind of Degumming method of idesia oil |
| CN112646663A (en) * | 2020-12-15 | 2021-04-13 | 武汉轻工大学 | Method for enriching, separating and purifying linoleic acid in sunflower seed oil |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102229593A (en) * | 2011-07-25 | 2011-11-02 | 四川省毛叶山桐子科技股份有限公司 | Method for preparing natural vitamin E from crude oil of Maoyeshan tung tree seed |
| CN105273848A (en) * | 2014-07-04 | 2016-01-27 | 漳州开发区欧中农业技术研发有限公司 | Method for extracting linoleic acid in citrus seed |
| CN104177246A (en) * | 2014-08-06 | 2014-12-03 | 陈存武 | Method for preparing conjugated linoleic acid by using rhus chinensis oil |
| RU2572788C1 (en) * | 2015-02-17 | 2016-01-20 | Федеральное государственное бюджетное учреждение "Российский кардиологический научно-производственный комплекс" Министерства здравоохранения Российской Федерации (ФГБУ "РКНПК" Минздрава России) | Method for obtaining linoleic acid |
| CN105837430A (en) * | 2016-05-04 | 2016-08-10 | 罗江县德金种植协会 | Method for extracting linoleic acid from idesia polycarpa crude oil |
| CN106497675A (en) * | 2016-11-16 | 2017-03-15 | 四川省林业科学研究院 | A kind of Degumming method of idesia oil |
| CN112646663A (en) * | 2020-12-15 | 2021-04-13 | 武汉轻工大学 | Method for enriching, separating and purifying linoleic acid in sunflower seed oil |
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Application publication date: 20101110 |