CN105949025A - Method for adsorbing and separating squalene from vegetable oil deodorized distillate - Google Patents
Method for adsorbing and separating squalene from vegetable oil deodorized distillate Download PDFInfo
- Publication number
- CN105949025A CN105949025A CN201610371973.5A CN201610371973A CN105949025A CN 105949025 A CN105949025 A CN 105949025A CN 201610371973 A CN201610371973 A CN 201610371973A CN 105949025 A CN105949025 A CN 105949025A
- Authority
- CN
- China
- Prior art keywords
- squalene
- adsorbent
- distillate
- adsorbing
- vegetable oil
- 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.)
- Pending
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
- C07C7/04—Purification; Separation; Use of additives by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/12—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
The invention discloses a method for adsorbing and separating squalene from vegetable oil deodorized distillate. According to the method for adsorbing and separating the squalene from the vegetable oil deodorized distillate provided by the invention, D101 type macroporous resin is used as an adsorbent. According to the method, an adsorbing material is directly thrown into a solution containing the squalene, and an efficient adsorption process can be completed at normal temperature. According to the method, organic solvents such as n-hexane are used for desorption, the desorption efficiency is extremely high, and the squalene can be efficiently purified. The adopted adsorbing materials do not dissolve in acid, alkali and the organic solvents, are excellent in mechanic strength, can be used repeatedly, is simple in regeneration technology, and low in reclamation cost. The adopted adsorbing materials statically and dynamically adsorb the squalene in the vegetable oil deodorized distillate at normal temperature, are excellent in preferential adsorption and desorption effects, and basically has no change in adsorbing capacity when being reused after desorption activation.
Description
Technical field
The invention belongs to the extractive technique field of Squalene, specifically, relate to that a kind of adsorbing separation is vegetable oil deodorized evaporates
Go out the method for Squalene in thing.
Background technology
Squalene has another name called zamene, squalene, squalene, entitled 2,6,10,15,19,23 hexamethyl 2,6 of chemistry,
10,14,18,22 tetracosa carbon six alkene, molecular formula C30H50, molecular weight 410.71, is the highly unsaturated hydrocarbon of one
Thing, is initially found in 1906 by by Japanese chemists Tsujimoto in black shark liver oil.Squalene is a kind of natural triterpene
Alkenes, polyunsaturated fat race hydrocarbon compound containing six unconjugated double bonds.Squalene has significant oxidation resistance,
Can generate by anticancer, can prevent cancerous cell from spreading to a certain extent and the leukopenia because of chemotherapy, to gastric cancer, esophagus
Cancer, pulmonary carcinoma have obvious curative effects；Squalene has allaying tiredness ability, can promote Superoxide dismutase and lactic dehydrogenase after entering human body
Enzyme significantly raises, and causes rapidly Oxidation, and promotes the secretion of bile, the effect of strengthening liver；Squalene has anti-painstaking effort
Pipe disease, can blood circulation promoting, it is possible to reduce the generation of low density lipoprotein, prevents and treat heart disease, hypertension, low
The disease such as blood pressure and apoplexy, current Squalene according to the difference of its purity oneself be widely used in health product, pharmaceuticals, food and
In cosmetics, highly purified Squalene pharmaceuticals especially and the first-selection of health product.
In recent years, in world wide, Squalene demand quickly increases.Squalene is primarily present in shark fish liver, and early
It is put into wild marine protection animal, has added low breeding potential and the environmental pollution destruction to fingerling of shark, more limit
The source of Squalene in shark hepatic.The demand growing in order to meet Squalene, the main manufacturer of world's Squalene one after another from
Animal livers extracts and transfers to the vegetable oil resource enriched extracts.Select plant oil deodorizing distillate carrying as Squalene
Take raw material, on the one hand, abundance, low production cost；On the other hand, also it is the resource reutilization to plant oil leftover,
There is extremely important society and economic implications.
The method relatively horn of plenty of Squalene is extracted at present, including supercritical CO from plant resources2Solvent extraction, solvent
Extraction method, esterification partition method, molecularly distilled, column chromatography etc..Deliver what some Squalenes purified the most successively
Paper, domestic patent not yet relates to.The research such as Southern Yangtze University Zhang Hongwu shows that ultrasonic assistant ether can extract from Rhizoma Paridis
To Squalene (northwest medicine magazine 2004 the fourth phase 161-162 page), but treating capacity is little, and purity is the highest.Cao its people etc. are with Fructus Canarii albi
Oil is raw material, utilizes silkworm silk immobilized enzyme hydrolysis, and result shows, under the catalytic action of immobilized enzyme, fatty acid has almost obtained
Full hydrolysis, separatory can obtain Squalene (biological engineering journal 1997 first phase 88-92 page) after standing, but this method purity is relatively
Low.Posada etc. utilize molecular distillation technique to extract Squalene from Petiolus Trachycarpi oil, and have investigated vapo(u)rizing temperature, charging rate etc.
On the impact of Squalene content in Petiolus Trachycarpi oil, result show Squalene just can enter under low temperature light phase in, content is
3.94%, to utilizing molecular distillation to extract Squalene, there is certain directive significance (Separation and Purification
Technology2007 second phase 220-229 page), though treating capacity is big, but energy consumption is excessive, high cost, and purity is relatively low.
The research such as Gunawan is by the silica gel column chromatography angle of departure zamene from soyabean deodorization distillate improved, with traditional silicagel column
Chromatography is compared, though having saving solvent, and feature (the Separation and Purification Reviews 2009 such as the shortest
Third phase 207-241 page in year), but this method cost intensive, operation complexity.Above-mentioned article is both for grinding of respective method expansion
Study carefully, be confined to again in respective deficiency, particularly in terms of the preparation of high-purity squalene, rarely have technology to reach, even if
Being that column chromatography chromatogram technology can not reach high-load (more than 95%), and treating capacity is little, purification efficiency is the highest.
Absorption method is wide in the application of natural active product extraction purification field, but to angle in plant oil deodorizing distillate
The research of zamene specific aim absorption rarely has report, and use absorption method have can be used repeatedly, easy and simple to handle, low cost
The features such as honest and clean, environmental friendliness, the recycling that can realize resource, therefore absorption method is applied to the extraction purification of Squalene and meets closely
The green that Nian Lai environmental project circle is advocated, efficient theme.
Summary of the invention
Present invention aim to overcome that the deficiencies in the prior art, it is provided that in a kind of adsorbing separation plant oil deodorizing distillate
The method of Squalene.
To achieve these goals, the present invention adopts the following technical scheme that
A kind of method of Squalene in adsorbing separation plant oil deodorizing distillate, selects D101 type macroporous adsorbent resin as absorption
Agent.
Concrete grammar comprises the steps:
(1) adsorbent is added in the plant oil deodorizing distillate containing Squalene, vibrate under room temperature or stir, filter and separate, angle
Zamene is adsorbed to be stayed in adsorbent；
(2) the D101 type macroporous adsorbent resin being adsorbed with Squalene is joined in desorbing agent, vibrate under room temperature or stir, mistake
Filter, makes Squalene be desorbed, and reclaims and obtains the desorbing agent solution containing Squalene and adsorbent；
(3) organic solvent is removed in distillation of being reduced pressure by the desorbing agent containing Squalene, obtains high-purity squalene；
(4) dry in the adsorbent of recovery is placed in 40 ~ 50 DEG C of vacuum drying ovens, be dried, store and reuse next time.
As preferably, in the above-mentioned methods, adsorbent is 5:1 with the Squalene mass ratio in plant oil deodorizing distillate
~8:1。
As preferably, in the above-mentioned methods, plant oil deodorizing distillate is olive oil deodorization distillate, soybean oil deodorize
Distillation or cottonseed oil deodorizer distillate etc..
As preferably, in the above-mentioned methods, described desorbing agent is normal hexane, ether or acetone.
In above-mentioned absorption Squalene, the obtained Squalene in eluent and eluant can by decompression distillation,
The methods such as decompression rotary evaporation separate.The eluant reclaimed can again be applied to be adsorbed with the resin of Squalene and carry out eluting.
Meanwhile, adsorbing material can reclaim and reuse, this to this application expanding production in the industry significant.
D101 macroporous adsorbent resin is the non-polar polymer adsorbent of a kind of synthetic, and specific surface area is very big, reaches
500~550 m2/ g, has porous and is similar to spongiosis, relies primarily on the Van der Waals force between resin matrix and adsorbate
The specific surface area huge with resin carries out physical absorption, such that it is able to reach to adsorb the nonpolar macromole of Squalene in the solution
Purpose.Use D101 type enriching and purifying macroporous resin effective components in plants such as soap two class, flavonoid, alkaloids, many
Phenols is not only greatly improved yield and purity, and has feature easy and simple to handle, pollution-free, reusable.
Compared with prior art, the method have the advantages that:
1, adsorbing material is directly put in the solution containing Squalene by the method for the present invention, can complete at normal temperatures efficiently
Adsorption process.
2, the method for the present invention uses the organic solvents such as normal hexane to be desorbed, and desorption rate is high, can efficiently purifying spiny dogfish
Alkene.
3, the adsorbing material that the method for the present invention is used is insoluble in acid, alkali and organic solvent, has good machinery strong
Degree, can be repeated several times use, and regeneration technology is simple, and cost recovery is cheap.
4, the adsorbing material that the method for the present invention is used, enters the Squalene in plant oil deodorizing distillate at normal temperatures
Row static state and dynamic adsorption, after having good selective absorption and desorption effect, and desorptive activation, reuse, adsorbance
Do not change.
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:
Weigh D101 type macroporous adsorbent resin 0.20 g, put into the Squalene olive oil deodorization distillate of 50 mL 2000 mg/L
In solution, it is placed at 20 DEG C, cultivates shaking table with the full wet bath of the speed oscillation of 200 rpm/min and vibrate 24 h, vibrate complete
After, take supernatant and use content (4.6 mm × 160 mm, 5 um, the XDB-of Squalene in high-performance liquid chromatogram determination solution
C18 chromatographic column, flowing is methanol mutually, flow velocity 1 ml/min, sample size 10 um, detects wavelength 210 nm, column temperature 30 DEG C), by tying
Fruit is learnt, the adsorbance of adsorbing material squalene is 165 mg/g.The adsorbing material being adsorbed with Squalene is joined just own
Alkane organic solvent is stirred under room temperature eluting, uses high performance liquid chromatography to record the content of Squalene in solution, by result
Understanding eluting rate is 96%.
Embodiment 2:
Weigh D101 type macroporous adsorbent resin 0.20 g, put into the Squalene soybean oil deodorizer distillate of 50 mL 1000 mg/L
In solution, it is placed at 20 DEG C, cultivates shaking table with the full wet bath of the speed oscillation of 200 rpm/min and vibrate 24 h, vibrate complete
After, take supernatant and use content (4.6 mm × 160 mm, 5 um, the XDB-of Squalene in high-performance liquid chromatogram determination solution
C18 chromatographic column, flowing is methanol mutually, flow velocity 1 ml/min, sample size 10 um, detects wavelength 210 nm, column temperature 30 DEG C), by tying
Fruit is learnt, the adsorbance of adsorbing material squalene is 149mg/g.The adsorbing material being adsorbed with Squalene is joined in ether
Be stirred eluting under room temperature, use high performance liquid chromatography to record the content of Squalene in solution, result understanding eluting rate is
98%。
Embodiment 3:
Weigh D101 type macroporous adsorbent resin 0.20 g, put into the Squalene cottonseed oil deodorizer distillate of 50 mL 1000 mg/L
In solution, it is placed at 40 DEG C, cultivates shaking table with the full wet bath of the speed oscillation of 200 rpm/min and vibrate 24 h, vibrate complete
After, take supernatant and use content (4.6 mm × 160 mm, 5 um, the XDB-of Squalene in high-performance liquid chromatogram determination solution
C18 chromatographic column, flowing is methanol mutually, flow velocity 1 ml/min, sample size 10 um, detects wavelength 210 nm, column temperature 30 DEG C), by tying
Fruit is learnt, the adsorbance of adsorbing material squalene is 118 mg/g.The adsorbing material being adsorbed with Squalene is joined acetone
It is stirred eluting under middle room temperature, uses high performance liquid chromatography to record the content of Squalene in solution, result understand eluting rate
It is 98%.
Embodiment 4:
Weigh D101 type macroporous adsorbent resin 0.20 g of reclaiming in absorption embodiment 1 and 2, put into 50 mL 2000 mg/
In the Squalene solution of L, it is placed at 20 DEG C, cultivates shaking table with the full wet bath of the speed oscillation of 200 rpm/min and vibrate 24 h,
After vibration, take supernatant use Squalene in high-performance liquid chromatogram determination solution content (4.6 mm × 160 mm, 5
Um, XDB-C18 chromatographic column, flowing is methanol mutually, flow velocity 1 ml/min, sample size 10 um, detects wavelength 210 nm, column temperature 30
DEG C), result to learn, the adsorbance of adsorbing material squalene is 163 mg/g.The adsorbing material being adsorbed with Squalene is added
Enter in normal hexane and under room temperature, be stirred eluting, use high performance liquid chromatography to record the content of Squalene in solution, by result
Understanding eluting rate is 97%.
Claims (5)
1. the method for Squalene in an adsorbing separation plant oil deodorizing distillate, it is characterised in that select D101 type macroporous absorption
Resin is as adsorbent.
Method the most according to claim 1, it is characterised in that comprise the steps:
(1) adsorbent is added in the plant oil deodorizing distillate containing Squalene, vibrate under room temperature or stir, filter and separate, angle
Zamene is adsorbed to be stayed in adsorbent；
(2) the D101 type macroporous adsorbent resin being adsorbed with Squalene is joined in desorbing agent, vibrate under room temperature or stir, mistake
Filter, makes Squalene be desorbed, and reclaims and obtains the desorbing agent solution containing Squalene and adsorbent；
(3) organic solvent is removed in distillation of being reduced pressure by the desorbing agent containing Squalene, obtains high-purity squalene；
(4) dry in the adsorbent of recovery is placed in 40 ~ 50 DEG C of vacuum drying ovens, be dried, store and reuse next time.
3. method as claimed in claim 1 or 2, it is characterised in that adsorbent and the Squalene in plant oil deodorizing distillate
Mass ratio is 5:1 ~ 8:1.
4. method as claimed in claim 1 or 2, it is characterised in that plant oil deodorizing distillate be olive oil deodorization distillate,
Soybean oil deodorizer distillate or cottonseed oil deodorizer distillate.
Method the most according to claim 2, it is characterised in that described desorbing agent is normal hexane, ether or acetone.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610371973.5A CN105949025A (en) | 2016-05-31 | 2016-05-31 | Method for adsorbing and separating squalene from vegetable oil deodorized distillate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610371973.5A CN105949025A (en) | 2016-05-31 | 2016-05-31 | Method for adsorbing and separating squalene from vegetable oil deodorized distillate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105949025A true CN105949025A (en) | 2016-09-21 |
Family
ID=56910986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610371973.5A Pending CN105949025A (en) | 2016-05-31 | 2016-05-31 | Method for adsorbing and separating squalene from vegetable oil deodorized distillate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105949025A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107287024A (en) * | 2017-08-01 | 2017-10-24 | 福建胜华农业科技发展有限公司 | A kind of preparation technology of aromatous camellia oil |
| CN107474936A (en) * | 2017-09-30 | 2017-12-15 | 福建师范大学 | A kind of pregnant woman's later stage of pregnancy edible oil and its processing technology |
| CN107502442A (en) * | 2017-09-30 | 2017-12-22 | 福建师范大学 | A kind of pregnant woman's nursing period edible oil and its processing technology |
| CN107494770A (en) * | 2017-09-30 | 2017-12-22 | 福建师范大学 | A kind of pregnant woman oil and its processing technology |
| CN107586596A (en) * | 2017-09-30 | 2018-01-16 | 福建胜华农业科技发展有限公司 | A kind of pregnant woman's pregnancy edible oil early stage and its processing technology |
| CN107778277A (en) * | 2016-08-24 | 2018-03-09 | 丰益(上海)生物技术研发中心有限公司 | The method for reclaiming squalene, vitamin E and/or sterol |
| CN112159300A (en) * | 2020-10-27 | 2021-01-01 | 中国科学院青岛生物能源与过程研究所 | Method for extracting squalene from plant deodorized distillate |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102146014A (en) * | 2011-01-22 | 2011-08-10 | 李文东 | Method for extracting squalene by using camellia oleosa seeds as raw materials and tea oil and squalene soft capsules |
| CN103708992A (en) * | 2013-12-27 | 2014-04-09 | 合肥工业大学 | Method for extracting squalene in vegetable oil deodorizer distillate through two-stage column chromatography |
| CN105016956A (en) * | 2014-04-23 | 2015-11-04 | 中粮营养健康研究院有限公司 | Squalene extracting method |
-
2016
- 2016-05-31 CN CN201610371973.5A patent/CN105949025A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102146014A (en) * | 2011-01-22 | 2011-08-10 | 李文东 | Method for extracting squalene by using camellia oleosa seeds as raw materials and tea oil and squalene soft capsules |
| CN103708992A (en) * | 2013-12-27 | 2014-04-09 | 合肥工业大学 | Method for extracting squalene in vegetable oil deodorizer distillate through two-stage column chromatography |
| CN105016956A (en) * | 2014-04-23 | 2015-11-04 | 中粮营养健康研究院有限公司 | Squalene extracting method |
Non-Patent Citations (1)
| Title |
|---|
| C. S. L. CHUA ET AL.: "Separation of squalene from palm fatty acid distillate using adsorption chromatography", 《EUR. J. LIPID SCI. TECHNOL.》 * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107778277A (en) * | 2016-08-24 | 2018-03-09 | 丰益(上海)生物技术研发中心有限公司 | The method for reclaiming squalene, vitamin E and/or sterol |
| CN107778277B (en) * | 2016-08-24 | 2022-09-16 | 丰益(上海)生物技术研发中心有限公司 | Process for the recovery of squalene, vitamin E and/or sterols |
| CN107287024A (en) * | 2017-08-01 | 2017-10-24 | 福建胜华农业科技发展有限公司 | A kind of preparation technology of aromatous camellia oil |
| CN107287024B (en) * | 2017-08-01 | 2021-03-23 | 福建胜华农业科技发展有限公司 | Preparation process of aromatic camellia oil |
| CN107474936A (en) * | 2017-09-30 | 2017-12-15 | 福建师范大学 | A kind of pregnant woman's later stage of pregnancy edible oil and its processing technology |
| CN107502442A (en) * | 2017-09-30 | 2017-12-22 | 福建师范大学 | A kind of pregnant woman's nursing period edible oil and its processing technology |
| CN107494770A (en) * | 2017-09-30 | 2017-12-22 | 福建师范大学 | A kind of pregnant woman oil and its processing technology |
| CN107586596A (en) * | 2017-09-30 | 2018-01-16 | 福建胜华农业科技发展有限公司 | A kind of pregnant woman's pregnancy edible oil early stage and its processing technology |
| CN112159300A (en) * | 2020-10-27 | 2021-01-01 | 中国科学院青岛生物能源与过程研究所 | Method for extracting squalene from plant deodorized distillate |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105949025A (en) | Method for adsorbing and separating squalene from vegetable oil deodorized distillate | |
| CN104651422B (en) | A kind of method that triglyceride type DHA and EPA are extracted from deep-sea fish | |
| Nguyen et al. | Extraction of oil from Moringa oleifera kernels using supercritical carbon dioxide with ethanol for pretreatment: Optimization of the extraction process | |
| Yuanfeng et al. | Kinetic and thermodynamic studies of sulforaphane adsorption on macroporous resin | |
| CN105016956B (en) | A kind of method for extracting squalene | |
| CN102559375A (en) | Method for extracting greasy from microalgae | |
| CN101700490B (en) | Deacidification adsorbent of grease and preparation method thereof | |
| Wang et al. | Separation and purification of amygdalin from thinned bayberry kernels by macroporous adsorption resins | |
| Tang et al. | Preparative separation and purification of rosmarinic acid from perilla seed meal via combined column chromatography | |
| JP2009530426A (en) | Process for producing highly enriched fractions of natural compounds from palm oil or palm oil derivatives | |
| CN106008253B (en) | A method of extracting high-purity ceramide from rice bran | |
| CN105848748B (en) | The chromatographic purification method of aliphatic acid | |
| Huang et al. | Production of anhydrous biobutanol using a biosorbent developed from oat hulls | |
| CN103933936A (en) | Preparation method and application of antibiotic composite adsorbent | |
| CN101597204A (en) | With the sweet oil is the method that raw material extracts high-purity squalene | |
| Li et al. | Preparation of activated carbon from herbal residues and kinetics of cephalosporin antibiotic adsorption in wastewater | |
| CN102630943B (en) | Spirulina gamma-linolenic acid extractive and preparation method thereof | |
| Liu et al. | Separation and purification of glabridin from a deep eutectic solvent extract of Glycyrrhiza glabra residue by macroporous resin and its mechanism | |
| TW201808277A (en) | Method for extracting and purifying conjugated triene linolenic acid comprising extracting, esterfying and purifying | |
| Chen et al. | Synthesis and application of novel silver magnetic amino silicone adhesive particles for preparation of high purity α-linolenic acid from tree peony seed oil under applied magnetic field | |
| CN101444720A (en) | High selective hydrogen bond absorption resin and separation and purification for effective components in folium ginkgo extract | |
| CN103641716A (en) | Method for extracting refined chicoric acid | |
| CN105085827A (en) | Preparation method of tanshinol surface molecularly-imprinted polymer | |
| CN103100371A (en) | Distillers' grains acid modified adsorption material and preparation process thereof | |
| CN107955706A (en) | In a kind of removing in backbone ester diglyceride method |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20160921 |
|
| RJ01 | Rejection of invention patent application after publication |