CN105067735B - Method for extracting and detecting dioctyl adipate from Euphausia superba - Google Patents
Method for extracting and detecting dioctyl adipate from Euphausia superba Download PDFInfo
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- CN105067735B CN105067735B CN201510439198.8A CN201510439198A CN105067735B CN 105067735 B CN105067735 B CN 105067735B CN 201510439198 A CN201510439198 A CN 201510439198A CN 105067735 B CN105067735 B CN 105067735B
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Abstract
The present invention discloses a method for extracting and detecting dioctyl adipate from Euphausia superba. The method comprises: (1) adopting Euphausia superba as a raw material, adopting ethanol as a solvent, carrying out ultrasonic extraction, and filtering the extraction solution to obtain the filtrate; (2) evaporating the filtrate to obtain a crude extract of the dioctyl adipate; (3) refining the crude extract of the dioctyl adipate by using column chromatography; (4) carrying out primary detection to obtain a dioctyl adipate sample; and (5) detecting the dioctyl adipate content by using gas chromatography-mass spectrometry. According to the present invention, the operations of the method is simple, accurate and reliable, the complete method is provided for the extraction and the detection of the dioctyl adipate from the Euphausia superba; and with the method, the utilization value of the Euphausia superba is further developed, and the direction is provided for the clean renewable energy sources.
Description
Technical field
The present invention relates to a kind of method extracted from krill and detect dioctyl adipate.
Background technology
Dioctyl adipate (DOA) is a kind of cold-resistant plasticizer of polyvinyl chloride, and its good cold-resistant function causes south
Pole krill is adapted to the cold weather in the South Pole；DOA has certain heat-resisting, fast light and resistance to water, and outstanding other toxicity are very low,
Stimulation to skin and eyes is little, can be used to manufacture the packing film of frozen food, cold-resistant agricultural film；In addition DOA is usually used in
The plasticizer of plastics and rubber processing and synthetic resin, is important chemical intermediate.
At present, two octanoic acid of usual adipic acid is to carry out synthesizing by chemical synthesis process being obtained, such as pungent by adipic acid and just
Alcohol direct esterification under acid catalysis is obtained, and many with the concentrated sulfuric acid and p-methyl benzenesulfonic acid as catalyst at present, these are chemically synthesized
The following defect of two sad method generally existing of adipic acid：Poor product quality, side reaction serious to equipment corrosion are more, post processing is multiple
The problems such as miscellaneous, environmental pollution serious (producing various waste water, waste residue).
Therefore, need a kind of method for exploring that cleaning extracts dioctyl adipate for problem above badly.
Krill (scientific name Euphausia superba), is a kind of krill for living in Antarctic Continent waters, and the bodily form is like little
Shrimp,, 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.
Krill contains rich in protein；Fatty acid species contained by krill lipid are more, and mostly unrighted acid；South Pole phosphorus
Shrimp is also containing abundant mineral matter element, including calcium, phosphorus, iron, zinc, selenium etc..In addition, krill also contains various active thing
Matter, such as enzyme, astaxanthin etc..According to statistics, the quantity for living in the krill in the Antarctic Continent waters of Antarctic Ocean can reach 2 × 109
Ton, possible quantity of the catch are estimated 5 × 106To 7 × 106Ton.The life-span of krill is generally 5-7, i.e. ripe after 2 ages,
Body length maximum can reach more than 60nm.Krill has the habit of knot group, and Jing often forms intensive in the shoaling layer of 200m or so
Colony.As krill has the features such as biomass is big, distribution is wide, increasing researcher begins to focus on the exploitation of krill
Value.
The relevant report of dioctyl adipate is not extracted at present from krill, it is more no to carry from krill
The method for taking and detecting dioctyl adipate.
The content of the invention
It is an object of the invention to provide a kind of simple to operate, accurate, extraction of reliable krill dioctyl adipate
And detection method.
The present invention is achieved by the following technical solutions：
. a kind of method that dioctyl adipate is extracted from krill, comprise the following steps：
(1) with krill as raw material, adopt ethanol for solvent, 20～40 DEG C, 300～400W, 20～40Hz bar
Ultrasonic extraction under part, filters extract, obtains filtrate；
(2) filtrate is evaporated, obtains the crude extract of dioctyl adipate；
(3) crude extract of adipic acid dibutyl ester is refined using column chromatography；
1. prepare silica gel column chromatography；
2. the crude extract of adipic acid dibutyl ester is added on silica gel bed；
3. elute：Eluant, eluent is the mixed solution of dichloromethane and methyl alcohol, controls elution volume, collects 900～1500mL
Eluent, and eluent is carried out concentrating, is dried, obtain adipic acid dibutyl ester.
A kind of method that dioctyl adipate is detected from krill, comprises the following steps：
(1) with krill as raw material, adopt ethanol for solvent, 20～40 DEG C, 300～400W, 20～40Hz conditions
Lower ultrasonic extraction, filters extract, obtains filtrate；
(2) filtrate is evaporated, obtains the crude extract of dioctyl adipate；
(3) crude extract of adipic acid dibutyl ester is refined using column chromatography；
1. prepare silica gel column chromatography；
2. the crude extract of adipic acid dibutyl ester is added on silica gel bed；
3. elute：Eluant, eluent is the mixed solution of dichloromethane and methyl alcohol, controls elution volume, Fractional Collections eluent,
Collect several times, and eluent is carried out concentrating, is dried, obtain several pieces sample liquid；
(4) Preliminary detection adipic acid dibutyl ester：
Taking several pieces sample liquid carries out TLC Preliminary detections, by several pieces sample liquid point on High Performance Thin silica gel plate, with body
Product is than being dichloromethane：Methyl alcohol=3～4：1 is solvent, launches, open up away from for 8～10cm (preferably 9cm), open up in exhibition cylinder
Panel is dried after complete, anisaldehyde staining reagent is used, is toasted 6-10 minutes at being subsequently placed in 100-105 DEG C, according to color, selected
Color change is hepatic sample liquid, as adipic acid dibutyl ester；
(5) examined using gas chromatography-mass spectrum and further detect adipic acid dibutyl ester：
Gas chromatography-mass spectrum testing conditions：
1. gas-chromatography column type number:DB-1, length:30m, internal diameter:0.25mm, film thickness:0.25 μm, carrier gas:He, stream
Speed：1mL/min；
2. sample introduction：Intake air temperature:250 DEG C, pattern：Shunting, split ratio：50:1, injection system：Manually；
3. heating schedule：50 DEG C of initial temperature, rises to 60 DEG C with 2 DEG C/min, then rises to 250 DEG C with 30 DEG C/min, keeps
8min；
4. sample size：0.2 μ L, solvent:EA；
5. ionize mode：Electron bombardment ionization source (EI), 150 DEG C of level Four bar temperature, 200 DEG C of ion source temperature；Monitoring mode：Entirely
Surface sweeping (40-400amu units)；Select ion scan pattern (SIM)；Ionizing energy：70eV；Solvent delay：2.06min；
Sample mass spectrum is obtained, is determined that hepatic sample liquid is dioctyl adipate, and is calculated dioctyl adipate
Content.
In step (1), the krill water content is 7～8%, and the addition ratio of krill and ethanol is：1g:
(5～10) mL.Through substantial amounts of it is demonstrated experimentally that when krill is 1g with the mass volume ratio of ethanol：During (5～10) mL, oneself
The extraction effect of adipate sample is best.
In step (1), the ethanol is the ethanol solution that mass fraction is 95%.
In step (2), specific operating procedure is：Filtrate in step (1) is placed in revolving instrument, in order to prevent oneself two
Sour dibutyl ester hydrolysis, is evaporated under the conditions of 20 DEG C, obtains the crude extract of dioctyl adipate.
Step (3) 1. in, the concrete grammar for preparing silica gel column chromatography is：
Take 60-70g, 200-300 mesh silica gel and 8-10 hours are activated at 100-110 DEG C, be cooled to room temperature；Add 2-3 times
Volumes methylene chloride is stirred, and makes silica gel suspend into pasty state homogenate；Chromatographic column cock is opened, by silica-dichloromethane mixture
Gently pour in chromatographic column along glass bar, chromatography vial wall is gently tapped with ear washing bulb and drive bubble, be added dropwise two when tapping
Chloromethanes is until silicagel column is settled completely；When dichloromethane liquid level reaches silica gel bed surface just, cut-out tap.
Step (3) 2. in, concrete grammar is：Will be adipic acid dibutyl ester crude extract slow along chromatography vial wall with glue head dropper
It is added dropwise on silica gel bed surface, notes reducing the disturbance to bed surface.Cock is opened, makes sample slowly enter top surface, then with 1-2mL bis-
Chloromethanes washs top post jamb.
Step (3) 3. in, the dichloromethane and methyl alcohol volume ratio are 8:1.Using the eluent efficiency of this ratio
Height, elution time are short.
Control elution volume, collects an eluent per 250～300mL, collects several times, and collection frequence is more than 5 times, and
Eluent is carried out concentrating, is dried, several pieces sample liquid is obtained.Adopt this method, make the collection and follow-up inspection of eluent
Survey efficiency to be all improved.
A kind of preferably elution process is：When sample liquid level reaches silica gel bed top surface just, eluant, eluent is added to start
Wash-out；It is dichloromethane with volume ratio：Methyl alcohol=8:1 eluent is eluted, and controls elution volume, and one is collected per 300mL
Secondary eluent, collects 5 times, numbering 1-5, and eluent is carried out concentrating, is dried.
In step (4), model GF of the High Performance Thin silica gel plate254, the High Performance Thin silica gel plate of different model is entered
Row is investigated, and obtains model GF254High Performance Thin silica gel plate separating effect it is best.
The invention has the beneficial effects as follows：
The method of the present invention is simple to operate, accurate, reliability and environmental protection, is that krill is extracted and detects adipic acid dibutyl ester
There is provided complete method.
The present invention extracts and detects adipic acid dibutyl ester from krill, further developed the exploitation value of krill
Value, while also the renewable energy utilization for cleaning provides direction.
Description of the drawings
Fig. 1：A is the gas chromatography retention time image of sample in embodiment 1；Gas phase colors of the B for 1 Plays product of embodiment
Spectrum retention time image.
Fig. 2：A is the mass spectrogram of sample in embodiment 1；Mass spectrograms of the B for 1 Plays product of embodiment.
Fig. 3：A is the gas chromatography retention time image of sample in embodiment 2；Gas phase colors of the B for 2 Plays product of embodiment
Spectrum retention time image.
Fig. 4：A is the mass spectrogram of sample in embodiment 2；Mass spectrograms of the B for 2 Plays product of embodiment.
Fig. 5：A is the gas chromatography retention time image of sample in embodiment 3；Gas phase colors of the B for 3 Plays product of embodiment
Spectrum retention time image.
Fig. 6：A is the mass spectrogram of sample in embodiment 3；Mass spectrograms of the B for 3 Plays product of embodiment.
Specific embodiment
The present invention is further described with reference to the accompanying drawings and examples.
Embodiment 1
Take and be dried krill 2g, be placed in 200mL, the beaker of a diameter of 6cm, addition mass fraction is 95% ethanol
10mL, in room temperature, 350w, 40kHz ultrasonic extraction, extracts 10 minutes, filters extract, and filtrate is placed in 20 DEG C of steamings in revolving instrument
It is dry, obtain the crude extract of dioctyl adipate.
Take 60g, 200-300 mesh silica gel to activate 10 hours at 100 DEG C, be cooled to room temperature；Add 2 times of volumes methylene chlorides
Stirring, makes silica gel suspend into pasty state homogenate；By chromatographic column cock open, by silica-dichloromethane mixture along glass bar slowly
Pour in chromatographic column, gently tap chromatography vial wall with ear washing bulb and drive bubble, dichloromethane is added dropwise when tapping up to silicon
Glue post is settled completely；When dichloromethane liquid level reaches silica gel bed surface just, cut-out tap.With glue head dropper along chromatography vial wall
Adipic acid dibutyl ester crude extract is slowly added dropwise on silica gel bed surface, notes reducing the disturbance to bed surface.Cock is opened, sample is made
Top surface slowly being entered, then top post jamb being washed with 1mL dichloromethane, when liquid level reaches silica gel bed top surface just, addition is washed
De- agent starts wash-out；Use dichloromethane：Methyl alcohol 8:1 (volume ratio) is eluted, and controls elution volume, is collected once per 300mL
Eluent, collects 5 times, numbering 1-5, and eluent is carried out concentrating, is dried；Merge 4-5 eluents, by 4, No. 5 sample liquids
5ul points are in GF254On High Performance Thin silica gel plate, with volume ratio as dichloromethane：Methyl alcohol=3:1 is solvent, is opened up in exhibition cylinder
Open, open up away from for 9cm, panel is dried after having opened up, anisaldehyde staining reagent is used, be subsequently placed in baking 10 minutes at 100 DEG C, carry out
Preliminary detection；Adipic acid dibutyl ester content, gas chromatography-mass spectrum testing conditions are detected using gas chromatography-mass spectrum：1st, gas phase color
Spectrum column type number:DB-1, length:30m, internal diameter:0.25mm, film thickness:0.25 μm, carrier gas:He, flow velocity：1mL/min；2nd, sample introduction：
Intake air temperature:250 DEG C, pattern：Shunting, split ratio：50:1, injection system：Manually；3rd, heating schedule：50 DEG C of initial temperature, with
2 DEG C/min rises to 60 DEG C, then rises to 250 DEG C with 30 DEG C/min, keeps 8min；4th, sample size：0.2 μ L, solvent:EA；5th, ionize
Mode：Electron bombardment ionization source (EI), 150 DEG C of level Four bar temperature, 200 DEG C of ion source temperature；Monitoring mode：Full surface sweeping (40-400amu
Unit)；Select ion scan pattern (SIM)；Ionizing energy：70eV；Solvent delay：2.06min.
Detected according to above detection method, obtained detection figure, such as Fig. 1 and 2.After testing and calculate in krill oneself
Adipate content is 0.061mg/g.
Embodiment 2
Dry krill 2g is taken, is placed in 200mL, the beaker of a diameter of 6cm, addition mass fraction is 95% ethanol
15mL, in room temperature, 350w, 20kHz ultrasonic extraction, extracts 15 minutes, filters extract, and filtrate is placed in 20 DEG C of steamings in revolving instrument
It is dry, obtain the crude extract of dioctyl adipate.
Take 65g, 200-300 mesh silica gel to activate 8 hours at 110 DEG C, be cooled to room temperature；Add 2 times of volumes methylene chlorides
Stirring, makes silica gel suspend into pasty state homogenate；By chromatographic column cock open, by silica-dichloromethane mixture along glass bar slowly
Pour in chromatographic column, gently tap chromatography vial wall with ear washing bulb and drive bubble, dichloromethane is added dropwise when tapping up to silicon
Glue post is settled completely；When dichloromethane liquid level reaches silica gel bed surface just, cut-out tap.With glue head dropper along chromatography vial wall
Adipic acid dibutyl ester crude extract is slowly added dropwise on silica gel bed surface, notes reducing the disturbance to bed surface.Cock is opened, sample is made
Top surface slowly being entered, then top post jamb being washed with 1mL dichloromethane, when liquid level reaches silica gel bed top surface just, addition is washed
De- agent starts wash-out；Use dichloromethane：Methyl alcohol 8:1 (volume ratio) is eluted, and controls elution volume, is collected once per 300mL
Eluent, collects 5 times, numbering 1-5, and eluent is carried out concentrating, is dried；Merge 4-5 eluents, by 4, No. 5 sample liquids
5ul points on GF254 High Performance Thin silica gel plates, with volume ratio as dichloromethane：Methyl alcohol=4：1 is solvent, is opened up in exhibition cylinder
Open, open up away from for 9cm, panel is dried after having opened up, anisaldehyde staining reagent is used, be subsequently placed in baking 6 minutes at 105 DEG C, carry out
Preliminary detection；Detected according to the gas chromatography-mass spectrum detection method in embodiment 1, obtained detection figure, such as Fig. 3 and 4.Jing is examined
In surveying and calculating krill, dioctyl adipate content is 0.06mg/g.
Embodiment 3
Dry krill 2g is taken, is placed in 200mL, the beaker of a diameter of 6cm, addition mass fraction is 95% ethanol
20mL, in room temperature, 350w, 28kHz ultrasonic extraction, extracts 15 minutes, filters extract, and filtrate is placed in 20 DEG C of steamings in revolving instrument
It is dry, obtain the crude extract of dioctyl adipate.
Take 70g, 200-300 mesh silica gel to activate 10 hours at 105 DEG C, be cooled to room temperature；Add 2 times of volumes methylene chlorides
Stirring, makes silica gel suspend into pasty state homogenate；By chromatographic column cock open, by silica-dichloromethane mixture along glass bar slowly
Pour in chromatographic column, gently tap chromatography vial wall with ear washing bulb and drive bubble, dichloromethane is added dropwise when tapping up to silicon
Glue post is settled completely；When dichloromethane liquid level reaches silica gel bed surface just, cut-out tap.With glue head dropper along chromatography vial wall
Adipic acid dibutyl ester crude extract is slowly added dropwise on silica gel bed surface, notes reducing the disturbance to bed surface.Cock is opened, sample is made
Top surface slowly being entered, then top post jamb being washed with 1mL dichloromethane, when liquid level reaches silica gel bed top surface just, addition is washed
De- agent starts wash-out；Use dichloromethane：Methyl alcohol 8:1 (volume ratio) is eluted, and controls elution volume, is collected once per 300mL
Eluent, collects 5 times, numbering 1-5, and eluent is carried out concentrating, is dried；Merge 4-5 eluents, by 4, No. 5 sample liquids
5ul points are in GF254On High Performance Thin silica gel plate, with volume ratio as dichloromethane：Methyl alcohol=4：1 is solvent, is opened up in exhibition cylinder
Open, open up away from for 9cm, panel is dried after having opened up, anisaldehyde staining reagent is used, be subsequently placed in baking 8 minutes at 105 DEG C, carry out
Preliminary detection；Detected according to the gas chromatography-mass spectrum detection method in embodiment 1, obtained detection figure, such as Fig. 5 and 6.Jing is examined
In surveying and calculating krill, dioctyl adipate content is 0.061mg/g.
Although the above-mentioned accompanying drawing that combines is described to the specific embodiment of the present invention, not to present invention protection model
The restriction enclosed, one of ordinary skill in the art should be understood that on the basis of technical scheme those skilled in the art are not
The various modifications made by needing to pay creative work or deformation are still within protection scope of the present invention.
Claims (8)
1. a kind of method that dioctyl adipate is extracted from krill, is characterized in that, comprise the following steps：
(1) with krill as raw material, ethanol is adopted for solvent, under conditions of 20～40 DEG C, 300～400W, 20～40Hz
Ultrasonic extraction, filters extract, obtains filtrate；
(2) filtrate is evaporated, obtains the crude extract of dioctyl adipate；
(3) crude extract of dioctyl adipate is refined using column chromatography；1. prepare silica gel column chromatography；2. by adipic acid two
The crude extract of monooctyl ester is added on silica gel bed；3. elute：Eluant, eluent is dichloromethane and the mixed solution of methyl alcohol, the dichloromethane
Alkane and methyl alcohol volume ratio are 8:1, elution volume is controlled, the eluent of 900～1500mL is collected, and eluent is carried out concentrating,
It is dried, obtains dioctyl adipate.
2. the method for claim 1, is characterized in that：In step (1), the addition ratio of krill and ethanol is：
1g:(5～10) mL.
3. the method for claim 1, is characterized in that：In step (2), filtrate is evaporated under the conditions of 20 DEG C, obtains oneself
The crude extract of adipate.
4. a kind of method that dioctyl adipate is detected from krill, is characterized in that, comprise the following steps：
(1) with krill as raw material, ethanol is adopted for solvent, surpass under the conditions of 20～40 DEG C, 300～400W, 20～40Hz
Sound is extracted, and is filtered extract, is obtained filtrate；
(2) filtrate is evaporated, obtains the crude extract of dioctyl adipate；
(3) crude extract of dioctyl adipate is refined using column chromatography；1. prepare silica gel column chromatography；2. by adipic acid two
The crude extract of monooctyl ester is added on silica gel bed；3. elute：Eluant, eluent is dichloromethane and the mixed solution of methyl alcohol, the dichloromethane
Alkane and methyl alcohol volume ratio are 8:1, elution volume is controlled, Fractional Collections eluent is collected several times, and eluent is carried out dense
Contract, be dried, obtain several pieces sample liquid；
(4) Preliminary detection dioctyl adipate：Taking several pieces sample liquid carries out TLC Preliminary detections, by several pieces sample liquid point in
On High Performance Thin silica gel plate, with volume ratio as 3～4：1 dichloromethane：Methyl alcohol is solvent, launches, open up away from for 8 in exhibition cylinder
～10cm, dries panel after having opened up, use anisaldehyde staining reagent, and 6-10 minutes, color are toasted at being subsequently placed in 100-105 DEG C
Change turns to hepatic sample liquid, as dioctyl adipate.
5. method as claimed in claim 4, is characterized in that：In step (3), elution volume is controlled, collected per 250～300mL
Eluent, collection frequence are more than 5 times, and eluent is carried out concentrating, is dried, and obtain several pieces sample liquid.
6. method as claimed in claim 5, is characterized in that：Control elution volume, collects an eluent, collects 5 per 300mL
It is secondary, and eluent is carried out concentrating, is dried, obtain 5 parts of sample liquids.
7. method as claimed in claim 4, is characterized in that：Model GF254 of the High Performance Thin silica gel plate.
8. method as claimed in claim 4, is characterized in that：Also include further detecting adipic acid using gas chromatography-mass spectrum
Dioctyl ester, gas chromatography-mass spectrum testing conditions：1. gas-chromatography column type number：DB-1, length:30m, internal diameter:0.25mm, thickness
Degree:0.25 μm, carrier gas:He, flow velocity：1mL/min；2. sample introduction：Intake air temperature:250 DEG C, pattern：Shunting, split ratio：50:1, note
Penetrate mode：Manually；3. heating schedule：50 DEG C of initial temperature, rises to 60 DEG C with 2 DEG C/min, then rises to 250 DEG C with 30 DEG C/min,
Keep 8min；4. sample size：0.2 μ L, solvent:EA；5. ionize mode：Electron bombardment ionization source, 150 DEG C of level Four bar temperature, ion gun
200 DEG C of temperature；Monitoring mode：Full scan, 40-400amu units；Select ion scan pattern；Ionizing energy：70eV；Solvent prolongs
Late：2.06min；Sample mass spectrum is obtained, and it is dioctyl adipate color change to be determined for hepatic sample liquid, and calculates oneself
The content of adipate.
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| CN102731358A (en) * | 2012-07-18 | 2012-10-17 | 山东师范大学 | Method for extracting astaxanthin diester from antarctic krill |
| CN103820223A (en) * | 2014-03-03 | 2014-05-28 | 山东师范大学 | Method for separating saturated fatty acid and unsaturated fatty acid from astaxanthin of euphausia superba |
| CN104782626A (en) * | 2015-03-26 | 2015-07-22 | 天津农学院 | Allelochemical algistat and extraction and purification method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100210745A1 (en) * | 2002-09-09 | 2010-08-19 | Reactive Surfaces, Ltd. | Molecular Healing of Polymeric Materials, Coatings, Plastics, Elastomers, Composites, Laminates, Adhesives, and Sealants by Active Enzymes |
| US20070144054A1 (en) * | 2005-12-22 | 2007-06-28 | Warczok Daniel J | Plastic fishing lure having porous particles |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102731358A (en) * | 2012-07-18 | 2012-10-17 | 山东师范大学 | Method for extracting astaxanthin diester from antarctic krill |
| CN103820223A (en) * | 2014-03-03 | 2014-05-28 | 山东师范大学 | Method for separating saturated fatty acid and unsaturated fatty acid from astaxanthin of euphausia superba |
| CN104782626A (en) * | 2015-03-26 | 2015-07-22 | 天津农学院 | Allelochemical algistat and extraction and purification method thereof |
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| Title |
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| Bioavailability of fatty acids from krill oil,krill meal and fish oil in healthy subjects-a randomized,single-dose,cross-over trial;Anton Kohler等;《Lipids in health and disease》;20150430;第14卷;第19～28页 * |
| Horizontally transferred genes in the genome of Pacific white shrimp,Litopenaeus vannamei;Jian-Bo Yuan等;《BMC Evolutionary Biology》;20131231;第13卷;第165～170页 * |
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