CN106083518A - A kind of Squalene and the separation method of vitamin E - Google Patents
A kind of Squalene and the separation method of vitamin E Download PDFInfo
- Publication number
- CN106083518A CN106083518A CN201610440848.5A CN201610440848A CN106083518A CN 106083518 A CN106083518 A CN 106083518A CN 201610440848 A CN201610440848 A CN 201610440848A CN 106083518 A CN106083518 A CN 106083518A
- Authority
- CN
- China
- Prior art keywords
- squalene
- vitamin
- separation method
- natural vitamin
- inclusion complex
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/005—Processes comprising at least two steps in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/152—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by forming adducts or complexes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
- C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses the separation method of a kind of Squalene and vitamin E.The method uses beta cyclodextrin inclusion to separate containing Squalene and natural Vitamin E mixture, utilize beta cyclodextrin and Squalene, the difference of natural Vitamin E different substrate weak interaction force, reached the purpose of purifies and separates under mild conditions by the Preferential adsorption of squalene.The Squalene of a small amount of ethanol dissolving and natural Vitamin E mixture, be added drop-wise in saturated beta cyclodextrin aqueous solution under constant temperature, and constant temperature stirs, cooling stands and separates out inclusion complex, filtering, vacuum drying, Squalene and natural Vitamin E dehydrated alcohol in inclusion complex extract.The present invention has that separation condition is gentle, technique simple, energy-conserving and environment-protective, the repeatable utilization of carrier of separating, also avoid material because having the features such as the be susceptible to oxidative phenomena of thermal sensitivity.
Description
Technical field
The invention belongs to isolated and purified field, specifically, relate to the separation method of a kind of Squalene and vitamin E.
Background technology
Natural Vitamin E has another name called tocopherol, is mainly derived from animal and plant fat, be used for treating sterile, habitual abortion and
Threatened abortion, belongs to again antioxidant, prevents the unsaturated bond of peroxidase to be combined on cell membrane, to incised wound, burns, always
Year speckle, pigmentation, xerosis cutis, prevent ultraviolet injury from having important effect.Squalene have another name called zamene, squalene,
Squalene, molecular formula C30H50, molecular weight 410.71, is a kind of height unsaturated hydrocarbons compounds, and Squalene also has the most anti-
Oxidability.Natural Vitamin E and Squalene are mainly used in health product and cosmetic industry at present, with carrying of quality of life
Rise, more and more higher to the prescription of natural Vitamin E and Squalene.
The most industrial natural Vitamin E and the Squalene prepared is mainly with plant oil deodorizing distillate as raw material, it
Main component also has free fatty, alcohol lipid, glyceride and other materials in addition to natural Vitamin E, Squalene.According to oil
The difference of material, natural Vitamin E proportion is between 1%-20%, and wherein soybean oil content is the highest, and Squalene is at olive
In olive oil, content is the highest.Natural Vitamin E and Squalene are high boiling point and boiling point easily aoxidizes close to active substance, both of which,
Industrial conventional extracting method is first raw material to be carried out pretreatment to be concentrated and purification again, in conjunction with multiple-grade molecular distillation,
But the product purity of isolated is low, and aoxidize because high temperature is as easy as rolling off a log in separation process.
Recent domestic has been delivered successively and has been related to the extraction of Squalene and natural Vitamin E in by-product of vegetable oil and divides
From paper and patent application.Hongtao Wan etc. utilizes the tocopherol in SCF-CO 2 separation soybean oil oil and spiny dogfish
Alkene, but extract operating process complexity, separating somewhat expensive, purity is the highest, relatively low (the Industrial & of the response rate
Engineering Chemistry Research 2004 volume 43 2753-2758 page).Qu Delin et al. proposes one
From the deodorization distillate that tocopherol content is relatively low, extract the process route of tocopherol, extremely change including first, wash, distill, secondary
The steps such as first is extremely changed, secondary washing, second distillation, methanol extraction, cooling remove impurity, strong-base anion-exchange resin process, produce
In product, tocopherol content is up to 50-60%, though this technique treating capacity is big, but complex process, the response rate is low, and purity does not reaches requirement
(application number CN 1034367).Posada etc. utilize molecular distillation technique to extract Squalene from Petiolus Trachycarpi oil, and have investigated distillation
Temperature, charging rate etc. are on the impact of Squalene content in Petiolus Trachycarpi oil, and result shows that Squalene just can enter gently under low temperature
Xiang Zhong, content is 3.94%, has certain directive significance (Separation and to utilizing molecular distillation to extract Squalene
Purification Technology2007 second phase 220-229 page), though treating capacity is big, but energy consumption is excessive, high cost,
Purity is relatively low.Additionally patent " technique of fractionally extracting natural VE by supercritical CO 2 fluid " (application number
02115535.6) and patent " method (application number 00103260.7) of supercritical extraction and concentrated natural vitamin E all has
There is complex operation, the shortcoming of high cost.Said extracted concentrated natural vitamin E and Squalene related work are both for
Each method launches research, there is significant limitation, particularly in high-purity squalene and the preparation side of natural Vitamin E
Face, is still difficult to reach.
Cyclodextrin is as the super molecular compound of a kind of " outer hydrophilic, interior hydrophobic ", it is possible to by intermolecular force and chi
Very little, different guest molecule forms different inclusion complexes, thus is carried out optionally by some composition in mixed system
Separating, wherein beta-schardinger dextrin-production cost is low, good stability, and molecular structure and physical property are more beneficial for dividing with some Organic substance
Son forms inclusion complex, has simple to operate, the feature of environmental protection, thus is widely used in isolation technics.
Summary of the invention
Present invention aim to overcome that the deficiencies in the prior art, it is provided that a kind of Squalene and the separation side of natural Vitamin E
Method.
To achieve these goals, the present invention adopts the following technical scheme that
A kind of Squalene and the separation method of vitamin E, it is characterised in that use beta-schardinger dextrin-inclusion angle of departure zamene and natural
Vitamin E, it is achieved Squalene and the separation of natural Vitamin E.
Above-mentioned separation method specifically includes following steps: the preparation of (1) inclusion complex: in the round-bottomed flask of 100 mL, will
Beta-schardinger dextrin-is added in deionized water, and in water-bath, saturated solution is prepared in stirring, Squalene and vitamin E/ethanol is mixed
Solution joins in the aqueous solution of beta-schardinger dextrin-, reacts under constant temperature；By reactant in 4 DEG C of condition cold preservation 24 h, vacuum filtration, add
Enter absolute ether washing inclusion complex three times, in order to remove remaining Squalene and vitamin E, the white filter cake cryogenic vacuum of gained
It is dried；
(2) separation of inclusion complex: inclusion complex is added solvent and extracts, is collected by filtration filtrate, and high-efficient liquid phase analysis measures it
Middle Squalene and the content of natural Vitamin E.
As preferably, in above-mentioned separation method, the temperature of water-bath is 35 DEG C, and duration of oscillation is 4 h.
As preferably, in above-mentioned separation method, in described Squalene and vitamin E/ethanol mixed solution, spiny dogfish
Alkene and vitamin E are equimolar.
As preferably, in above-mentioned separation method, described Squalene and vitamin E/ethanol mixed solution and beta-schardinger dextrin-
Mol ratio be 1:4-1:1.
As preferably, in above-mentioned separation method, described extractant is ethanol.
In above-mentioned separation method, can be by decompression distillation, decompression in filtrate obtained after inclusion complex extraction is filtered
The methods such as rotary evaporation separate and are concentrated to give natural Vitamin E and Squalene mixture, then are rejoined by mixture saturated
Cyclodextrin solution carries out the preparation of inclusion complex, repeats above-mentioned process several times, available high concentration Squalene.The extractant reclaimed
Can again be applied to extraction containing natural Vitamin E and the inclusion complex of Squalene；Meanwhile, utilize same method to cleaning mixture
In natural Vitamin E concentrating under reduced pressure, repeatedly inclusion separates available highly purified natural Vitamin E.
Under this technology weak interaction force based on cyclodextrin drives, utilize the molecular recognition mechanism of supramolecular chemistry, right
The difference of the molecular structure of natural Vitamin E and Squalene, equimolar is more subconditional than guest molecule vies each other down, host molecule
Beta-schardinger dextrin-is easier to tendency and forms stable inclusion complex, under cooling, with crystal form with guest molecule Squalene
Separating out, major part natural Vitamin E then stays in the solution, thus realizes efficiently separating of natural Vitamin E and Squalene.
Compared with prior art, the method have the advantages that:
1, the separation process conditions of the present invention is gentle, simple to operate, it is to avoid Conventional espresso causes high energy consumption, easily produces material
The problems such as high cost that high-temperature oxydation and supercritical extraction cause, operation are complicated.
2, the recyclable recycling of beta-schardinger dextrin-that the present invention uses, and repeat performance is stable, cost recovery price
Cheap.
3, the separating technology environmental protection of the present invention, uses beta-schardinger dextrin-as inclusion main body, and extractant is nontoxic nothing
The ethanol of evil.
4, products obtained therefrom purity of the present invention is high.The present invention is by the research mol ratio of material, heating-up temperature and repetition inclusion
The impact on inclusion separating resulting of the factors such as number of times, thus draw Optimum separation condition, repeat inclusion separating technology more than 2 times,
Available highly purified natural Vitamin E and Squalene.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is described further, but protection scope of the present invention is not limited thereto.
Embodiment 1:
1.135g β-CD (1mmol) is added to deionized water and makes in saturated solution, be placed in 35 DEG C of stirred in water bath, treat β-
After CD all dissolves, the mixture solution of 0.0822g Squalene and 0.0860g vitamin E is added dropwise to the water of β-CD
In the middle of solution.Rotating speed is to react 6h under conditions of 180 rpm, then by reactant in freezing 24 h of 4 DEG C of conditions, and vacuum filtration,
And wash filter cake, low-temperature vacuum drying with deionized water and normal hexane.Inclusion complex uses solvent extraction to extract, in room temperature
Under, inclusion complex is joined in 25ml dehydrated alcohol and extract, under magnetic agitation effect, stir 2 h, extracted by filtration liquid, then
The method distilled by decompression obtains the higher Squalene of purity and natural Vitamin E, analyzes through HPLC and can obtain purity respectively
Being 87% and 83%, separation factor is 4.001.
Embodiment 2:
1.135g β-CD (1mmol) is added to deionized water and makes in saturated solution, be placed in 45 DEG C of stirred in water bath, treat β-
After CD all dissolves, the mixture solution of 0.0822g Squalene and 0.0860g vitamin E is added dropwise to the water of β-CD
In the middle of solution.Rotating speed is to react 6h under conditions of 180 rpm, then by reactant in freezing 24 h of 4 DEG C of conditions, and vacuum filtration,
And wash filter cake, low-temperature vacuum drying with deionized water and normal hexane.Inclusion complex uses solvent extraction to extract, in room temperature
Under, inclusion complex is joined in 25ml dehydrated alcohol and extract, under magnetic agitation effect, stir 2 h, extracted by filtration liquid, then
The method distilled by decompression obtains the higher Squalene of purity and natural Vitamin E, and can obtain purity through HPLC analysis is 84%
With 79%, separation factor is 3.495.
Embodiment 3:
1.135g β-CD (1mmol) is added to deionized water and makes in saturated solution, be placed in 45 DEG C of stirred in water bath, treat β-
After CD all dissolves, the mixture solution of 0.1233g Squalene and 0.1290g vitamin E is added dropwise to the water of β-CD
In the middle of solution.Rotating speed is to react 6h under conditions of 180 rpm, then by reactant in freezing 24 h of 4 DEG C of conditions, and vacuum filtration,
And wash filter cake, low-temperature vacuum drying with deionized water and normal hexane.Inclusion complex uses solvent extraction to extract, in room temperature
Under, inclusion complex is joined in 25ml dehydrated alcohol and extract, under magnetic agitation effect, stir 2 h, extracted by filtration liquid, then
The method distilled by decompression obtains the higher Squalene of purity and natural Vitamin E, and can obtain purity through HPLC analysis is 81%
With 77%, separation factor is 3.415.
Embodiment 4:
1.135g β-CD (1mmol) is added to deionized water and makes in saturated solution, be placed in 35 DEG C of stirred in water bath, treat β-
After CD all dissolves, the mixture solution of 0.0822g Squalene and 0.0860g vitamin E is added dropwise to the water of β-CD
In the middle of solution.Rotating speed is to react 6h under conditions of 180 rpm, then by reactant in freezing 24 h of 4 DEG C of conditions, and vacuum filtration,
And wash filter cake, low-temperature vacuum drying with deionized water and normal hexane.Inclusion complex uses solvent extraction to extract, in room temperature
Under, inclusion complex is joined in 25ml dehydrated alcohol and extract, under magnetic agitation effect, stir 2 h, extracted by filtration liquid, then
The method distilled by decompression obtains the higher Squalene of purity and natural Vitamin E, the again spiny dogfish of inclusion isolated
Alkene and natural Vitamin E add saturated β-CD, repeat above inclusion technique 2 times, finally concentrate available high-purity Squalene and
Natural Vitamin E, can obtain purity through HPLC analysis is 93% and 91%.
Claims (6)
1. a Squalene and the separation method of vitamin E, it is characterised in that use beta-schardinger dextrin-inclusion angle of departure zamene and dimension
Raw element E, it is achieved Squalene and the separation of natural Vitamin E.
Separation method the most according to claim 1, it is characterised in that comprise the following steps: the preparation of (1) inclusion complex:
In the round-bottomed flask of 100 mL, being added in deionized water by beta-schardinger dextrin-, in water-bath, saturated solution is prepared in stirring, by angle
Zamene and vitamin E/ethanol mixed solution join in the aqueous solution of beta-schardinger dextrin-, react under constant temperature；By reactant in 4 DEG C of bars
Part cold preservation 24 h, vacuum filtration, add absolute ether washing inclusion complex three times, in order to remove remaining Squalene and vitamin E,
The white filter cake low-temperature vacuum drying of gained；
(2) separation of inclusion complex: inclusion complex is added solvent and extracts, is collected by filtration filtrate, and high-efficient liquid phase analysis measures it
Middle Squalene and the content of natural Vitamin E.
Separation method the most according to claim 2, it is characterised in that the temperature of water-bath is 35 DEG C, duration of oscillation is 4 h.
Separation method the most according to claim 2, it is characterised in that described Squalene and vitamin E/ethanol mixed solution
In, Squalene and vitamin E are equimolar.
Separation method the most according to claim 2, it is characterised in that described Squalene and vitamin E/ethanol mixed solution
It is 1:4-1:1 with the mol ratio of beta-schardinger dextrin-.
Separation method the most according to claim 2, it is characterised in that described extractant is ethanol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610440848.5A CN106083518B (en) | 2016-06-20 | 2016-06-20 | A kind of separation method of squalene and vitamin E |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610440848.5A CN106083518B (en) | 2016-06-20 | 2016-06-20 | A kind of separation method of squalene and vitamin E |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106083518A true CN106083518A (en) | 2016-11-09 |
| CN106083518B CN106083518B (en) | 2019-03-08 |
Family
ID=57236827
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610440848.5A Active CN106083518B (en) | 2016-06-20 | 2016-06-20 | A kind of separation method of squalene and vitamin E |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106083518B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106748615A (en) * | 2016-12-09 | 2017-05-31 | 广州白云山汉方现代药业有限公司 | A kind of method that squalene is extracted from grease |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100832796B1 (en) * | 2006-08-23 | 2008-05-27 | 주식회사 마크로케어 | Method for extraction of squalene or squalane using cyclodextrin and cosmetic composition containing squalene or squalane-cyclodextrin inclusion complex prepared thereby |
| CN101830770A (en) * | 2010-06-02 | 2010-09-15 | 天津大学 | Method for extracting squalene from vegetable oil deodorized distillate |
-
2016
- 2016-06-20 CN CN201610440848.5A patent/CN106083518B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100832796B1 (en) * | 2006-08-23 | 2008-05-27 | 주식회사 마크로케어 | Method for extraction of squalene or squalane using cyclodextrin and cosmetic composition containing squalene or squalane-cyclodextrin inclusion complex prepared thereby |
| CN101830770A (en) * | 2010-06-02 | 2010-09-15 | 天津大学 | Method for extracting squalene from vegetable oil deodorized distillate |
Non-Patent Citations (1)
| Title |
|---|
| 范晶等: "维生素E 、β-环糊精包合物的制备工艺研究", 《亚太传统医药》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106748615A (en) * | 2016-12-09 | 2017-05-31 | 广州白云山汉方现代药业有限公司 | A kind of method that squalene is extracted from grease |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106083518B (en) | 2019-03-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101830770B (en) | Method for extracting squalene from vegetable oil deodorized distillate | |
| TWI242438B (en) | Process for the selective extraction of furanic lipid compounds and polyhydroxylated fatty alcohols of avocado | |
| CN103708992B (en) | A kind of level chromatography method extracts the method for squalene in plant oil deodorizing distillate | |
| CN104710391B (en) | Method for extracting luteolin and beta-sitosterol from peanut shells | |
| CN102648271B (en) | Method for extracting unsaponifiables from renewable raw materials | |
| CN100355766C (en) | Method for preparing and purifying uperarin through membrane technology | |
| CN102001947A (en) | Method for preparing honeysuckle chlorogenic acid | |
| CN103450316B (en) | A kind of method simultaneously extracting tea saponin, tea seed flavonoid glycoside and tea polysaccharide | |
| CN102617693B (en) | Method utilizing subcritical water extraction technology to extract and prepare ursolic acid from loquat leaves | |
| CN101870637B (en) | Technology for extracting and preparing policosanol | |
| CN102031116B (en) | New method for preparing rosemary natural antioxidant | |
| CN100357358C (en) | Method for preparing licopin | |
| CN106083518A (en) | A kind of Squalene and the separation method of vitamin E | |
| Igarashi et al. | Dehydrative esterification of carboxylic acids with alcohols catalyzed by diarylammonium p-dodecylbenzenesulfonates in water | |
| CN101654398A (en) | Method for extracting high purity polyprenol from plant needle leaf raw material | |
| CN102229593A (en) | Method for preparing natural vitamin E from crude oil of Maoyeshan tung tree seed | |
| CN106748615A (en) | A kind of method that squalene is extracted from grease | |
| CN104311616B (en) | A kind of extraction high purity cortex fraxini and method of fraxin from Cortex Fraxini | |
| CN103432028B (en) | A kind of Paeonia ostii seed natural activity protective skin cream and preparation method thereof | |
| CN102399251A (en) | Method for preparing high-purity geniposide | |
| CN102198231A (en) | Method for extracting ceramide-rich lipid from byproducts of agriculture and forestry by supercritical extraction technology | |
| CN106543196B (en) | A method of extracting sesamin from sesame oil | |
| CN104710492A (en) | Method for extracting androstenedione in bi-liquid phases system | |
| CN108948074A (en) | A method of using poly ion liquid extraction separation purification phosphatidyl choline | |
| CN102600216A (en) | Method for extracting plant polyphenol from Chinese chestnut involucre |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |