CN105130809B - Method of preparing dioctyl adipate from waste liquid through extraction of alkaloid from euphausia superba - Google Patents
Method of preparing dioctyl adipate from waste liquid through extraction of alkaloid from euphausia superba Download PDFInfo
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- CN105130809B CN105130809B CN201510439748.6A CN201510439748A CN105130809B CN 105130809 B CN105130809 B CN 105130809B CN 201510439748 A CN201510439748 A CN 201510439748A CN 105130809 B CN105130809 B CN 105130809B
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- waste liquid
- ethyl acetate
- krill
- alkaloid
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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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- 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
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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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
- C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
Abstract
The invention discloses a method of preparing dioctyl adipate from a waste liquid through extraction of alkaloid from euphausia superb, wherein the method comprises following steps: (1) adding ethyl acetate to the waste liquid from extraction of alkaloid by euphausia superb for performing extraction, wherein the volume ratio of each addition amount of the ethyl acetate to the waste liquid is (1-2):4; (2) adding n-butyl alcohol to lower water solution for carrying extraction, separating an n-butyl alcohol layer, evaporate-drying the n-butyl alcohol layer to obtain a paste substance, wherein each addition amount of the n-butyl alcohol to the lower water solution is (1-2):4; (3) adding a petroleum ether-ethyl acetate mixed solution, stirring the mixture uniformly and packing a column, loading the paste substance as a sample, and eluting the sample respectively with the petroleum ether-ethyl acetate mixed solutions being (3-1):1 in volume ratio, and collecting eluants; and (4) collecting the eluant being 1:1 in ratio, and concentrating and drying the eluant to obtain the dioctyl adipate. In the invention, the dioctyl adipate is prepared from the waste liquid through extraction of alkaloid from the euphausia superb for the first time, thereby fully utilizing the waste liquid from extraction.
Description
Technical field
The present invention relates to a kind of utilization krill extracts the method that the waste liquid of alkaloid prepares dioctyl adipate, belong to
Food and chemical technology field.
Background technology
Krill (scientific name Euphausia superba Dana), is a kind of krill for living in Antarctic Continent waters, body
Likeness in form shrimp,, using small phytoplankton as food, about 6 centimetres of height weighs about 2 grams, and MaLS was up to 6 years for they.
Krill is the main food source of the Antarctic organisms such as marine mammal, birds and fish, is the pass of Antarctic ecosystems
Key species.Krill contains abundant lipid, and contained fatty acid species are more, and mostly unrighted acid etc.;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..
Dioctyl adipate (DOA) is a kind of cold-resistant plasticizer of polyvinyl chloride, and DOA also has certain heat-resisting, resistance to
Light and resistance to water, toxicity are very low, and the stimulation to skin and eyes is little, can be used for daily-use chemical industry such as manufactureization shape product.Can be used to make
The packing film of refrigeration jelly food, cold-resistant agricultural film;In addition DOA is usually used in plastics and rubber processing and synthetic resin
Plasticizer, is important chemical intermediate.
The extraction of applicant of the present invention's long campaigns krill active material, finds in research process, South Pole phosphorus
Remaining waste liquid after shrimp alkaloid is extracted also has plurality of active ingredients.If can make full use of to these compositions, do not only have
Beneficial to environmental protection, but also product chain can be extended, improve value-added content of product.
Not yet it is related to from krill extract the report that dioctyl adipate is prepared in the waste liquid of alkaloid at present, because
This, develops a kind of method of the waste liquid recycling that alkaloid is extracted to krill, for the exploitation of krill resource
Tool is of great significance.
The content of the invention
For above-mentioned prior art, it is an object of the invention to provide a kind of utilization krill extracts the waste liquid system of alkaloid
The method of standby dioctyl adipate.
For achieving the above object, the present invention adopts following technical proposals:
A kind of utilization krill extracts the method that the waste liquid of alkaloid prepares dioctyl adipate, and step is as follows:
(1) add ethyl acetate to extract in the waste liquid that alkaloid is extracted to krill, mix, layering obtains upper strata acetic acid
Methacrylate layer and lower aqueous solution, each addition of ethyl acetate are (1-2) with the volume ratio of waste liquid:4;
(2) extracting n-butyl alcohol being added in lower aqueous solution, being mixed, stratification is isolated n-butanol layer, is evaporated, obtains
Paste, each addition of n-butanol are (1-2) with the volume ratio of lower aqueous solution:4;
(3) the addition petroleum ether-ethyl acetate mixed liquor (3 in the silica gel after activation:1, V:V), mix thoroughly, fill post, will step
Suddenly the paste of (2) is used as sample loading, 20-35 times for the sample quality of loading of silica gel consumption, is (3- with volume ratio respectively
1):1 petroleum ether-ethyl acetate mixed liquor is eluted as eluent, and the flow velocity of eluent is 1-2ml/min, and collection is washed
De- liquid;
(4) by petroleum ether-ethyl acetate volume ratio be 1:1 eluent is collected, and concentrate drying obtains final product adipic acid two pungent
Ester.
Specifically, in step (1), the krill extracts the preparation method of the waste liquid of alkaloid and is:
(1) in krill add containing 0.3-0.8% (volume fraction) acetic acid ethanol solution extract, krill with
The ratio of the ethanol solution addition of acetic acid is 1g:(5-10) ml, filters, filtrate concentration, obtains paste;
(2) aqueous sulfuric acid being added in the paste of step (1), mixing, add petroleum ether, mixed, layering is obtained
Layer petroleum ether layer and lower aqueous solution, the volume and the mass ratio of paste that aqueous sulfuric acid, petroleum ether are added every time is 15ml:
5ml:(2-4)g;
(3) ammoniacal liquor being added in the lower aqueous solution of step (2), mixing, add chloroform, mixed, layering obtains lower floor's chlorine
The volume ratio of the lower aqueous solution of imitative liquid and the upper strata aqueous solution, each addition of ammoniacal liquor, chloroform and step (2) is (1-2):
(1-2):3, the upper strata aqueous solution is the waste liquid that krill extracts alkaloid.
Preferably, in step (1), add ethyl acetate extract number of times be 2-4 time, each addition of ethyl acetate and
The volume ratio of waste liquid is 1:4.The extraction time of ethyl acetate is elected as 2-4 time, not only effectively removes the target component in waste liquid
Outer impurity, moreover it is possible to reduce the energy waste brought by the increase of extraction time as far as possible.
Preferably, in step (2), the number of times for adding extracting n-butyl alcohol is 4-6 time, each addition of n-butanol and lower floor
The volume ratio of the aqueous solution is 1:4.Add the n-butanol of the volume ratio effectively can extract the hexanedioic acid dioctyl ester in waste liquid
Come.
Preferably, in step (3), the method that the activation of silica gel is adopted is that silica gel is activated under the conditions of 110-120 DEG C 8-
12h.The present invention effectively increases the absorption property of silica gel using the silica gel after activation.
Preferably, in step (3), the mesh number of the silica gel is 200-300 mesh.Particle size (the i.e. mesh of silica gel of silica gel
Number) separated performance is closely related.The silica gel mesh number that the present invention is selected is 200-300 mesh, and separating effect is preferable, elution speed
It is moderate.
Preferably, in step (3), the ratio of the silica gel addition after the petroleum ether-ethyl acetate mixed liquor and activation is
1g:(1-2)ml.The present invention adopts wet method dress post, and first by the silica gel after activation, with appropriate solvent, (petroleum ether-ethyl acetate mixes
Solution) mix thoroughly after, be further filled with pillar.
Preferably, in step (3), elute the eluent for adopting and be respectively:
Volume ratio is 3:1 petroleum ether-ethyl acetate mixed solution, the ratio of the consumption of eluent and the sample quality of loading
For 0.5L:(2-3)g;
Volume ratio is 1:1 petroleum ether-ethyl acetate mixed solution, the ratio of the consumption of eluent and the sample quality of loading
For 0.5L:(2-3)g.
Eluent and elution requirement select to be very crucial, single solvent conduct for the separating effect of column chromatography
Eluent, tends not to reach good separating effect.For the principle that the selection of eluent does not have directiveness at present can not abided by
Follow, need constantly to test, convert the composition of eluent to reach optimal separating effect.The present invention adopts petroleum ether-acetic acid
Dioctyl adipate effectively can be isolated and purified out by ethyl ester as eluent.
Beneficial effects of the present invention:
The waste liquid that the present invention is extracted using krill alkaloid first has prepared hexanedioic acid dioctyl ester, and it is right to realize
Krill alkaloid extracts making full use of for waste liquid, and not only beneficial to environmental protection, and the hexanedioic acid dioctyl ester for preparing has preferably
Using value, extend the product chain of krill product, increased value-added content of product.
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 dry shrimp of 200g krills is weighed, 95% ethanol of 1400ml 4-10 DEG C of (wherein acetic acid containing 7ml) cold soaking 4 days is added,
Coarse filtration.Filter residue repeats above procedure cold soaking once.After filtrate merges twice, refined filtration obtains filtrate, and Jing rotates to obtain paste 58g (50
DEG C the relative density of paste is surveyed for 1.3).
300ml pH=3.5H are added in paste2SO4The aqueous solution, mixes, and moves into separatory funnel, adds 100ml stones
Oily ether, mixing are static, separate upper strata petroleum ether solution, lower aqueous solution, then repeat above procedure with same amount (V) petroleum ether and extract
Once, 300ml lower aqueous solutions are about obtained.
Lower aqueous solution enters separatory funnel, is added thereto to the mixing of 100ml ammoniacal liquor, adds 100ml chloroforms, mixes, quiet
(upper strata yellow, lower floor are faint yellow) is layered only.This point of liquid process is repeated 2 times with chloroform again.The chloroform solution for obtaining lower floor is used to extract
Alkaloid, and the upper strata aqueous solution (yellow thick) about 400ml is obtained, as krill extracts the waste liquid of alkaloid.
To in the 400ml aqueous solution of upper strata, add ethyl acetate about 100ml to mix, static layering obtain upper strata ethyl acetate layer and
Lower aqueous solution, then repeat point liquid extraction 2 times with same amount ethyl acetate, totally 3 times, obtain lower aqueous solution about 400ml.
N-butanol 100ml is added in lower aqueous solution, is mixed, static layering, obtain upper n-butanol layer and lower floor respectively
The aqueous solution.Repeat above extraction process 4 times with same amount n-butanol, totally 5 times, n-butanol layer is merged, about 600ml, rotate, obtain cream
Shape thing 25g.
The silica gel of 200~300 mesh of 66g is taken, after 120 DEG C of activation 8h, appropriate petroleum ether-ethyl acetate (3 is added:1) mix
Liquid 100ml, mixes thoroughly.Add it to, in the silicagel column of 3cm × 30cm, after the completion of wet method dress post, be loaded 2g, with petroleum ether-acetic acid
Ethyl ester=3:1 (0.5L), 1:1 (0.5L) is used as elution, flow velocity 2ml/min.An eluent is collected per 200ml.Will
Petroleum ether-ethyl acetate=1:1 eluent collects revolving, obtains yellow stiff paste form 0.48mg.
Testing conditions are as follows to be detected to material composition using GC-MS methods to yellow paste:
Detecting instrument:Agilent 7890GC-5975MS;
GC-MS conditions:DB-1 chromatographic columns (30m × 0.25mm × 0.25 μ L), helium stream, flow velocity:1mL/min, solvent prolong
Slow 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 DEG C with 30 DEG C/min,
Keep 8min.
After testing, yellow paste is dioctyl adipate
Embodiment 2:
The dry shrimp of 200g krills is weighed, 95% ethanol of 1000ml 4-10 DEG C of (wherein acetic acid containing 5ml) cold soaking 4 days is added,
Coarse filtration.Filter residue repeats above procedure cold soaking once.After filtrate merges twice, refined filtration obtains filtrate, and Jing rotates to obtain paste 52g (50
DEG C the relative density of paste is surveyed for 1.3).
300ml pH=3.5H are added in paste2SO4The aqueous solution, mixes, and moves into separatory funnel, adds 100ml stones
Oily ether, mixing are static, separate upper strata petroleum ether solution, lower aqueous solution, then repeat above procedure with same amount (V) petroleum ether and extract
Once, 300ml lower aqueous solutions are about obtained.
Lower aqueous solution enters separatory funnel, is added thereto to the mixing of 100ml ammoniacal liquor, adds 100ml chloroforms, mixes, quiet
(upper strata yellow, lower floor are faint yellow) is layered only.This point of liquid process is repeated 2 times with chloroform again.The chloroform solution for obtaining lower floor is used to extract
Alkaloid, and the upper strata aqueous solution (yellow thick) about 400ml is obtained, as krill extracts the waste liquid of alkaloid.
To in the 400ml aqueous solution of upper strata, add ethyl acetate about 100ml to mix, static layering obtain upper strata ethyl acetate layer and
Lower aqueous solution, then repeat point liquid extraction 2 times with same amount ethyl acetate, totally 3 times, obtain lower aqueous solution about 400ml.
N-butanol 100ml is added in lower aqueous solution, is mixed, static layering, obtain upper n-butanol layer and lower floor respectively
The aqueous solution.Repeat above extraction process 4 times with same amount n-butanol, totally 5 times, n-butanol layer is merged, about 600ml, rotate, obtain cream
Shape thing 25g.
The silica gel of 200~300 mesh of 66g is taken, after 120 DEG C of activation 8h, appropriate petroleum ether-ethyl acetate (3 is added:1) mix
Liquid 100ml, mixes thoroughly.Add it to, in the silicagel column of 3cm × 30cm, after the completion of wet method dress post, be loaded 2g, with petroleum ether-acetic acid
Ethyl ester=3:1 (0.5L), 1:1 (0.5L) is used as elution, flow velocity 2ml/min.An eluent is collected per 200ml.Will
Petroleum ether-ethyl acetate=1:1 eluent collects revolving, obtains yellow stiff paste form 0.45mg.
Yellow paste is detected to material composition using GC-MS methods, detection method is with embodiment 1, after testing, yellow
Color paste is dioctyl adipate.
Embodiment 3:
The dry shrimp of 200g krills is weighed, 95% ethanol of 1600ml 4-10 DEG C of (wherein acetic acid containing 8ml) cold soaking 4 days is added,
Coarse filtration.Filter residue repeats above procedure cold soaking once.After filtrate merges twice, refined filtration obtains filtrate, and Jing rotates to obtain paste 52g (50
DEG C the relative density of paste is surveyed for 1.3).
300ml pH=3.5H are added in paste2SO4The aqueous solution, mixes, and moves into separatory funnel, adds 100ml stones
Oily ether, mixing are static, separate upper strata petroleum ether solution, lower aqueous solution, then repeat above procedure with same amount (V) petroleum ether and extract
Once, 300ml lower aqueous solutions are about obtained.
Lower aqueous solution enters separatory funnel, is added thereto to the mixing of 100ml ammoniacal liquor, adds 100ml chloroforms, mixes, quiet
(upper strata yellow, lower floor are faint yellow) is layered only.This point of liquid process is repeated 2 times with chloroform again.The chloroform solution for obtaining lower floor is used to extract
Alkaloid, and the upper strata aqueous solution (yellow thick) about 400ml is obtained, as krill extracts the waste liquid of alkaloid.
To in the 400ml aqueous solution of upper strata, add ethyl acetate about 200ml to mix, static layering obtain upper strata ethyl acetate layer and
Lower aqueous solution, then repeat point liquid extraction 2 times with same amount ethyl acetate, totally 3 times, obtain lower aqueous solution about 400ml.
N-butanol 200ml is added in lower aqueous solution, is mixed, static layering, obtain upper n-butanol layer and lower floor respectively
The aqueous solution.Repeat above extraction process 4 times with same amount n-butanol, totally 5 times, n-butanol layer is merged, about 600ml, rotate, obtain cream
Shape thing 25g.
The silica gel of 200~300 mesh of 66g is taken, after 120 DEG C of activation 8h, appropriate petroleum ether-ethyl acetate (3 is added:1) mix
Liquid 100ml, mixes thoroughly.Add it to, in the silicagel column of 3cm × 30cm, after the completion of wet method dress post, be loaded 2g, with petroleum ether-acetic acid
Ethyl ester=3:1 (0.5L), 1:1 (0.5L) is used as elution, flow velocity 2ml/min.An eluent is collected per 200ml.Will
Petroleum ether-ethyl acetate=1:1 eluent collects revolving, obtains yellow stiff paste form 0.51mg.
Yellow paste is detected to material composition using GC-MS methods, detection method is with embodiment 1, after testing, yellow
Color paste is dioctyl adipate.
Above-described embodiment is the present invention preferably embodiment, but embodiments of the present invention not by above-described embodiment
Limit, other any Spirit Essences without departing from the present invention and the change, modification, replacement 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 utilization krill extracts the method that the waste liquid of alkaloid prepares dioctyl adipate, it is characterised in that step
It is as follows:
(1) add ethyl acetate to extract in the waste liquid that alkaloid is extracted to krill, mix, layering obtains upper strata ethyl acetate
Layer and lower aqueous solution, each addition of ethyl acetate are (1-2) with the volume ratio of waste liquid:4;
(2) extracting n-butyl alcohol being added in lower aqueous solution, being mixed, stratification is isolated n-butanol layer, is evaporated, and obtains paste
Thing, each addition of n-butanol are (1-2) with the volume ratio of lower aqueous solution:4;
(3) petroleum ether-ethyl acetate mixed liquor is added in the silica gel after activation, mixed thoroughly, fill post, by the paste of step (2)
Used as sample loading, 20-35 times for the sample quality of loading of silica gel consumption is (3-1) with volume ratio respectively:1 petroleum ether-
Ethyl acetate mixtures are eluted as eluent, and the flow velocity of eluent is 1-2ml/min, collects eluent;
(4) by petroleum ether-ethyl acetate volume ratio be 1:1 eluent is collected, and concentrate drying obtains final product dioctyl adipate;
The preparation method that the krill extracts the waste liquid of alkaloid is as follows:
(1) add containing the ethanol solution extraction that volume fraction is 0.3-0.8% acetic acid, krill and acetic acid in krill
Ethanol solution addition ratio be 1g:(5-10) ml, filters, filtrate concentration, obtains paste;
(2) aqueous sulfuric acid being added in the paste of step (1), mixing, add petroleum ether, mixed, layering obtains upper strata stone
Oily ether layer and lower aqueous solution, the volume and the mass ratio of paste that aqueous sulfuric acid, petroleum ether are added every time is 15ml:5ml:
(2-4)g;
(3) ammoniacal liquor being added in the lower aqueous solution of step (2), mixing, add chloroform, mixed, layering obtains lower floor's chloroform solution
Volume ratio with the lower aqueous solution of the upper strata aqueous solution, each addition of ammoniacal liquor, chloroform and step (2) is (1-2):(1-2):
3, the gained upper strata aqueous solution is the waste liquid that krill extracts alkaloid.
2. the method that the waste liquid for extracting alkaloid using krill as claimed in claim 1 prepares dioctyl adipate, its
It is characterised by, in step (1), adds the number of times that ethyl acetate is extracted to be 2-4 time, each addition of ethyl acetate and waste liquid
Volume ratio is 1:4.
3. the method that the waste liquid for extracting alkaloid using krill as claimed in claim 1 prepares dioctyl adipate, its
It is characterised by, in step (2), the number of times for adding extracting n-butyl alcohol is 4-6 time, each addition of n-butanol and lower aqueous solution
Volume ratio be 1:4.
4. the method that the waste liquid for extracting alkaloid using krill as claimed in claim 1 prepares dioctyl adipate, its
It is characterised by, in step (3), the method that the activation of silica gel is adopted is that silica gel is activated under the conditions of 110-120 DEG C 8-12h.
5. the method that the waste liquid for extracting alkaloid using krill as claimed in claim 1 prepares dioctyl adipate, its
It is characterised by, in step (3), the mesh number of the silica gel is 200-300 mesh.
6. the method that the waste liquid for extracting alkaloid using krill as claimed in claim 1 prepares dioctyl adipate, its
It is characterised by, in step (3), in adding petroleum ether-ethyl acetate mixed liquor in the silica gel to after activation, petroleum ether and second
The volume ratio of acetoacetic ester is 3:1.
7. the method that the waste liquid for extracting alkaloid using krill as claimed in claim 6 prepares dioctyl adipate, its
It is characterised by, in step (3), the ratio of the silica gel addition after the petroleum ether-ethyl acetate mixed liquor and activation is 1g:(1-
2)ml。
8. the method that the waste liquid for extracting alkaloid using krill as claimed in claim 1 prepares dioctyl adipate, its
It is characterised by, in step (3), elutes the eluent for adopting and be respectively:
Volume ratio is 3:1 petroleum ether-ethyl acetate mixed solution, the consumption of eluent with the ratio of the sample quality of loading is
0.5L:(2-3)g;
Volume ratio is 1:1 petroleum ether-ethyl acetate mixed solution, the consumption of eluent with the ratio of the sample quality of loading is
0.5L:(2-3)g。
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CN106279180B (en) * | 2016-07-19 | 2018-03-23 | 山东师范大学 | The diketone of pyrrolo- [1,2 a] pyrazine 1,4, the extraction purification and detection method of hexahydro 3 (2 methyl-propyl) in a kind of krill |
CN106279181B (en) * | 2016-07-19 | 2018-03-23 | 山东师范大学 | A kind of extraction purification and detection method of the non-phenol alkalescent alkaloid of krill |
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