CN105085258B - A kind of method for extracting dioctyl adipate from Antarctic krill - Google Patents
A kind of method for extracting dioctyl adipate from Antarctic krill Download PDFInfo
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- CN105085258B CN105085258B CN201510439767.9A CN201510439767A CN105085258B CN 105085258 B CN105085258 B CN 105085258B CN 201510439767 A CN201510439767 A CN 201510439767A CN 105085258 B CN105085258 B CN 105085258B
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- antarctic krill
- benzene
- dioctyl adipate
- extraction
- extracting
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
Abstract
The invention discloses a kind of method for extracting dioctyl adipate from Antarctic krill, step is as follows：(1) ether extraction is added in Antarctic krill, filter, obtain filtering residue；(2) in filtering residue, benzene, supersound extraction is added to filter, the filtering residue after ultrasound adds benzene, and stirring is extracted, and united extraction liquid is evaporated, obtains benzene extractiveses；(3) aqueous sulfuric acid dissolving being added to benzene extractiveses, being filtered, add chloroform extraction in filtrate, the addition of chloroform is (1 2) with the volume ratio of filtrate：1, stratification obtains sour water layer and chloroform layer A；(4) in chloroform layer A, sodium hydrate aqueous solution extraction, stratification is added to obtain aqueous alkali layer and chloroform layer B；(5) chloroform layer B is evaporated off solvent, obtains final product dioctyl adipate.The present invention is extracted from Antarctic krill first and has obtained dioctyl adipate, and adipic acid dioctyl ester purity is more than 94%.
Description
Technical field
The present invention relates to a kind of method for extracting dioctyl adipate from Antarctic krill, category food and chemical field.
Background technology
Antarctic krill (scientific name Euphausia superba Dana), is that a kind of carapace for living in Antarctic Continent waters is moved
Thing,, using small phytoplankton as food, about 6 centimetres of height weighs about 2 grams, and MaLS was up to 6 years for they.South Pole phosphorus
Shrimp is the main food source of the Antarctic organisms such as marine mammal, birds and Fish, is the key species of Antarctic ecosystems.
Antarctic krill contains abundant fatty acid species, mostly unsaturated fatty acid etc.；Antarctic krill is also containing abundant mineral unit
Element, including calcium, phosphorus, ferrum, zinc, selenium etc..In addition, Antarctic krill also contains various active material, such as enzyme, astaxanthin etc..
Dioctyl adipate (DOA) is a kind of cold-resistant plasticizer of polrvinyl chloride, and DOA has certain heat-resisting, fast light
And resistance to water, especially other toxicity are very low, and the stimulation to skin and eyes is little, can be used for daily-use chemical industry and such as manufactures cosmetics.?
Can be used to manufacture the packing film of frozen food, cold-resistant agricultural film；In addition DOA is usually used in plastics and rubber processing and closes
The plasticizer of resin, is important chemical intermediate.
The report that from Antarctic krill extract dioctyl adipate is not yet related at present.The present invention is first from Antarctic krill
Middle extraction obtains dioctyl adipate, for the exploitation tool of Antarctic krill resource is of great significance.
Content of the invention
For above-mentioned prior art, it is an object of the invention to provide a kind of extract dioctyl adipate from Antarctic krill
Method.
For achieving the above object, the present invention adopts following technical proposals：
A kind of method for extracting dioctyl adipate from Antarctic krill, step are as follows：
(1) ratio for adding ether extraction, Antarctic krill and ether addition in Antarctic krill is 1g:(6-10) mL, mistake
Filter, obtains filtering residue；
(2) ratio for adding benzene, supersound extraction, filtering residue and benzene addition in the filtering residue of step (1) is 1g:(4-6) mL, mistake
Filter, the filtering residue after ultrasound add benzene, and psychrolusia stirring is extracted, and the ratio of filtering residue and benzene addition after ultrasound is 1g:(4-6)
ML, united extraction liquid, is evaporated, and obtains benzene extractiveses；
(3) volume fraction is added for the aqueous sulfuric acid dissolving of 1-3%, benzene extractiveses and aqueous sulfuric acid to benzene extractiveses
The ratio of addition is 1g:(10-30) mL, filters, addition chloroform extraction in filtrate, and the addition of chloroform with the volume ratio of filtrate is
(1-3):1, stratification obtains sour water layer and chloroform layer A；
(4) in chloroform layer A, volume fraction is added to extract for the sodium hydrate aqueous solution of 1-3%, sodium hydrate aqueous solution
The volume ratio of addition and chloroform layer A be (1-3):1, stratification obtains aqueous alkali layer and chloroform layer B；
(5) chloroform layer B is evaporated off solvent, obtains final product dioctyl adipate.
Preferably, in step (1), Antarctic krill first passes through freeze-drying process before ether extraction is added.Due to the South Pole
Enzyme in krill body has very high activity, and after Antarctic krill is fished for, its internal endogenous digestive enzyme can highly active degraded
Protein, makes the tissue fast decoupled after death, accelerates the self-dissolving of Antarctic krill, corrupt and rotten；By to Antarctic krill
Lyophilization pretreatment is carried out, Antarctic krill self-dissolving is prevented from, the quality of Antarctic krill is effectively kept.
Preferably, in step (1), the number of times for adding ether extraction is 4-6 time, and the time of extraction is 1-2h every time.Ether
Extraction time elect as 4-6 time, not only efficiently separate out the dioctyl adipate in Antarctic krill, moreover it is possible to as far as possible reduce extract time
The energy waste brought by several increases.The purpose for adding ether is in order to remove small molecular weight impurity in advance, so as to improve extraction
The purity of thing.
Preferably, in step (2), the frequency of supersound extraction is 20-40KHz, ultrasonic 2s, is spaced 2s, ultrasonic 3-5 time, per
Secondary 30min.Supersound extraction mainly uses the cavitation of ultrasound wave to increase motion frequency and the speed of material molecule, so as to
Increase the penetration power of solvent, improve the dissolution rate for being extracted composition；The power of supersound extraction, extraction time and ultrasonic time are
The principal element of extraction efficiency is affected, the present invention is by the optimization to ultrasonic technique condition so as to ensureing high extraction ratio
Under the premise of, reduce energy consumption again.
Preferably, in step (2), stir extract condition be psychrolusia (4-6 DEG C), low temperature control avoid extract point
Solution.Alr mode is mechanical agitation or magnetic agitation.
Preferably, in step (3), the volume fraction of the aqueous sulfuric acid of addition is 2%；Select the sulphuric acid of the concentration water-soluble
Liquid both can guarantee that enough acidity prevented the too high oxidation Decomposition for causing purpose thing of sulfuric acid concentration to remove acid impurities, again.
Preferably, in step (4), the volume fraction of the sodium hydrate aqueous solution of addition is 2%；Select the hydrogen-oxygen of the concentration
Change sodium water solution to remove alkaline impurities.
The material composition that extraction is obtained is detected using GC-MS methods, GC-MS conditions：DB-1 chromatographic columns (30m ×
0.25mm×0.25μL)；Carrier gas：Helium；Flow velocity：1mL/min, solvent delay 2.06min；Heating schedule：Initial temperature is 50
DEG C, 60 DEG C are warmed up to 2 DEG C/min, then are raised to 250 DEG C with 30 DEG C/min, keep 8min.Ionization mode:EI, 70eV；Ion
Source temperature:250℃；Carrier gas:Helium；Column flow rate：1.0mL/min.
Beneficial effects of the present invention：
The present invention is extracted from Antarctic krill first and has obtained dioctyl adipate, and the adipic acid dioctyl ester purity of preparation exists
More than 94%.
Description of the drawings
Fig. 1 is schemed for the GC-MS of 1 sample of embodiment；
Fig. 2 is schemed for the GC-MS of 2 sample of embodiment；
Fig. 3 is schemed for the GC-MS of 3 sample of embodiment.
Specific embodiment
With reference to embodiment, the present invention is further illustrated, it should explanation, and the description below is merely to solution
The present invention is released, its content is not defined.
Embodiment 1：
The cryodesiccated Antarctic krill of 100g is weighed, adds ether 800ml, room temperature to extract 5 times, each 1h, to lixiviating solution
Colourless.Filter, after filter residue and drying, add 500ml benzene, ultrasonic power 20KHz, ultrasonic 2s are spaced 2s, ultrasonic 4 times, every time
30min.500mL benzene is added in the filtering residue after ultrasound, and psychrolusia (4-6) DEG C stirring is extracted, extraction time 24h.Merge institute
There are benzene extraction liquid, rotary evaporation to remove benzene, obtain benzene extract.
The H that 10mL volume fractions are 2% is added in benzene extract2SO4Aqueous solution, dissolving, filtration.Filtrate adds equal-volume
Chloroform, magnetic agitation extract 1h, after standing stand after upper strata：Sour water layer；Lower floor：Chloroform layer A.Add in chloroform layer A
Isopyknic volume fraction be 2%NaOH aqueous solutions, magnetic agitation extract 1h, after standing upper strata：Aqueous alkali layer；Lower floor：Chloroform
Layer B.After chloroform layer B is evaporated chloroform, sample quality is obtained for 2.28mg.
Testing conditions are as follows to be detected to material composition using GC-MS methods to sample：
Detecting instrument：Agilent 7890GC-5975MS；
GC-MS conditions：DB-1 chromatographic columns (30m × 0.25mm × 0.25 μ L)；Carrier gas：Helium；Flow velocity：1mL/min, solvent
Postpone 2.06min；Heating schedule：Initial temperature is 50 DEG C, is warmed up to 60 DEG C with 2 DEG C/min, then is raised to 250 with 30 DEG C/min
DEG C, keep 8min.Ionization mode:EI, 70eV；Ion source temperature:250℃；Carrier gas:Helium；Column flow rate：1.0mL/min；Enter
Sample loading mode:Shunting, ratio 50:1；Sampling volume:0.2μL.
After testing, as a result as shown in figure 1, the material composition 95.19% in sample is dioctyl adipate.
Embodiment 2：
The cryodesiccated Antarctic krill of 100g is weighed, adds ether 600mL, room temperature to extract 5 times, each 1h, to lixiviating solution
Colourless.Filter, after filter residue and drying, add 400mL benzene, ultrasound, power 28KHz, ultrasonic 2s are spaced 2s, ultrasonic 4 times, every time
30min.400mL benzene is added in the filtering residue after ultrasound, and psychrolusia (4-6) DEG C stirring is extracted, extraction time 24h.Merge institute
There are benzene extraction liquid, rotary evaporation to remove benzene, obtain benzene extract.
The H that 20mL volume fractions are 1% is added in benzene extract2SO4Aqueous solution, dissolving, filtration.Filtrate adds equal-volume
Chloroform, magnetic agitation extract 1h, after standing upper strata：Sour water layer；Lower floor：Chloroform layer A.Equal-volume is added in chloroform layer A
Volume fraction be 1%NaOH aqueous solutions, magnetic agitation extract 1h, after standing upper strata：Aqueous alkali layer；Lower floor：Chloroform layer B.Chlorine
After imitative layer B is evaporated chloroform, sample quality is obtained for 2.41mg.
Sample is detected to material composition using GC-MS methods, detection method after testing, is as a result such as schemed with embodiment 1
Shown in 2, the material composition 94.26% in sample is dioctyl adipate.
Embodiment 3：
The cryodesiccated Antarctic krill of 100g is weighed, adds ether 1000mL, room temperature to extract 5 times, each 1h, to lixiviating solution
Colourless.Filter, after filter residue and drying, add 600mL benzene, ultrasound, power 40KHz, ultrasonic 2s are spaced 2s, ultrasonic 4 times, every time
30min.600mL benzene is added in the filtering residue after ultrasound, and psychrolusia (4-6) DEG C stirring is extracted, extraction time 24h.Merge institute
There are benzene extraction liquid, rotary evaporation to remove benzene, obtain benzene extract.
The H that 30mL volume fractions are 3% is added in benzene extract2SO4Aqueous solution, dissolving, filtration.Filtrate adds equal-volume
Chloroform, magnetic agitation extract 1h, after standing upper strata：Sour water layer；Lower floor：Chloroform layer A.Equal-volume is added in chloroform layer A
Volume fraction be 3%NaOH aqueous solutions, magnetic agitation extract 1h, after standing upper strata：Aqueous alkali layer；Lower floor：Chloroform layer B.Chlorine
After imitative layer B is evaporated chloroform, sample quality is obtained for 2.37mg.
Sample is detected to material composition using GC-MS methods, detection method after testing, is as a result such as schemed with embodiment 1
Shown in 3, the material composition 96.85% in sample is dioctyl adipate.
Above-described embodiment is the present invention preferably embodiment, but embodiments of the present invention are not by above-described embodiment
Limit, other any spirit without departing from the present invention and the change, modification, replacement that is made under principle, combine, simplification,
Equivalent substitute mode is should be, is included within protection scope of the present invention.
Claims (8)
1. a kind of from Antarctic krill extract dioctyl adipate method, it is characterised in that step is as follows：
(1) ratio for adding ether extraction, Antarctic krill and ether addition in Antarctic krill is 1g：(6-10) mL, filters, obtains
Filtering residue；
(2) ratio for adding benzene, supersound extraction, filtering residue and benzene addition in the filtering residue of step (1) is 1g：(4-6) mL, filters,
Benzene is added to the filtering residue after ultrasound, stirring is extracted, the ratio of filtering residue and benzene addition after ultrasound is 1g：(4-6) ml, merging are carried
Liquid is taken, is evaporated, obtain benzene extractiveses；
(3) in benzene extractiveses, volume fraction is added to dissolve for the aqueous sulfuric acid of 1-3%, benzene extractiveses are added with aqueous sulfuric acid
The ratio for entering amount is 1g:(10-30) mL, filters, addition chloroform extraction in filtrate, and the addition of chloroform with the volume ratio of filtrate is
(1-3)：1, stratification obtains sour water layer and chloroform layer A；
(4) in chloroform layer A add volume fraction for 1-3% sodium hydrate aqueous solution extract, sodium hydrate aqueous solution plus
The volume ratio for entering amount with chloroform layer A is (1-3)：1, stratification obtains aqueous alkali layer and chloroform layer B；
(5) chloroform layer B is evaporated off solvent, obtains final product dioctyl adipate.
2. the method for extracting dioctyl adipate as claimed in claim 1 from Antarctic krill, it is characterised in that its feature exists
In, in step (1), Antarctic krill first passes through freeze-drying process before ether extraction is added.
3. the method for extracting dioctyl adipate as claimed in claim 1 from Antarctic krill, it is characterised in that step (1)
In, the number of times for adding ether extraction is 4-6 time, and the time of extraction is 1-2h every time.
4. the method for extracting dioctyl adipate as claimed in claim 1 from Antarctic krill, it is characterised in that step (2)
In, the power of supersound extraction is 20-40KHz, ultrasonic 2s, is spaced 2s, ultrasonic 3-5 time, each 30min.
5. the method for extracting dioctyl adipate as claimed in claim 1 from Antarctic krill, it is characterised in that step (2)
In, it is 4-6 DEG C of psychrolusia to stir the condition that extracts.
6. the method for extracting dioctyl adipate as claimed in claim 5 from Antarctic krill, it is characterised in that step (2)
In, it is mechanical agitation or magnetic agitation to stir the alr mode for extracting.
7. the method for extracting dioctyl adipate as claimed in claim 1 from Antarctic krill, it is characterised in that step (3)
In, the volume fraction of the aqueous sulfuric acid of addition is 2%.
8. the method for extracting dioctyl adipate as claimed in claim 1 from Antarctic krill, it is characterised in that step (4)
In, the volume fraction of the sodium hydrate aqueous solution of addition is 2%.
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| CN102731358B (en) * | 2012-07-18 | 2014-05-14 | 山东师范大学 | Method for extracting astaxanthin diester from antarctic krill |
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