CN117486713B - Method for selectively extracting DHA from microalgae based on bisimidazole ionic liquid - Google Patents
Method for selectively extracting DHA from microalgae based on bisimidazole ionic liquid Download PDFInfo
- Publication number
- CN117486713B CN117486713B CN202311374575.5A CN202311374575A CN117486713B CN 117486713 B CN117486713 B CN 117486713B CN 202311374575 A CN202311374575 A CN 202311374575A CN 117486713 B CN117486713 B CN 117486713B
- Authority
- CN
- China
- Prior art keywords
- ionic liquid
- dha
- bisimidazole
- microalgae
- extracting
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 title claims abstract description 27
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 21
- AZUHIVLOSAPWDM-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-1h-imidazole Chemical compound C1=CNC(C=2NC=CN=2)=N1 AZUHIVLOSAPWDM-UHFFFAOYSA-N 0.000 title claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 27
- 241000195493 Cryptophyta Species 0.000 claims abstract description 14
- 239000008367 deionised water Substances 0.000 claims abstract description 11
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000001035 drying Methods 0.000 claims abstract description 10
- 238000010438 heat treatment Methods 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 239000002994 raw material Substances 0.000 claims abstract description 4
- 238000010992 reflux Methods 0.000 claims abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
- 239000010779 crude oil Substances 0.000 claims description 15
- 239000003921 oil Substances 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 241000003595 Aurantiochytrium limacinum Species 0.000 claims description 8
- 239000003208 petroleum Substances 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims 2
- 239000002585 base Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000000605 extraction Methods 0.000 abstract description 16
- 238000009776 industrial production Methods 0.000 abstract description 4
- 239000004519 grease Substances 0.000 abstract description 2
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 72
- 229940090949 docosahexaenoic acid Drugs 0.000 description 36
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 36
- 238000004817 gas chromatography Methods 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 241001474374 Blennius Species 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- GRONZTPUWOOUFQ-UHFFFAOYSA-M sodium;methanol;hydroxide Chemical compound [OH-].[Na+].OC GRONZTPUWOOUFQ-UHFFFAOYSA-M 0.000 description 5
- 230000009286 beneficial effect Effects 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 235000021323 fish oil Nutrition 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- -1 1-butyl-3 methylimidazole tetrafluoroborate Chemical compound 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 241001052560 Thallis Species 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 210000004102 animal cell Anatomy 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000036996 cardiovascular health Effects 0.000 description 1
- 238000004332 deodorization Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- OVYTZAASVAZITK-UHFFFAOYSA-M sodium;ethanol;hydroxide Chemical compound [OH-].[Na+].CCO OVYTZAASVAZITK-UHFFFAOYSA-M 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000000194 supercritical-fluid extraction Methods 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
Abstract
The invention discloses a method for selectively extracting DHA from microalgae based on biimidazole ionic liquid, which takes microalgae grease as a raw material, adds an alkaline alcohol solution, and carries out heating reflux; adding deionized water and bisimidazole ionic liquid, standing and layering; and taking the lower layer solution, adding acid to adjust the pH value, extracting by using an organic solvent, drying, and concentrating under reduced pressure to obtain a DHA algae oil finished product. The bisimidazole ionic liquid adopted by the invention can be used for selectively extracting DHA in microalgae, has high extraction rate and purity and good selectivity, and has good industrial production application prospect.
Description
Technical Field
The invention relates to the technical field of natural product extraction, in particular to a method for selectively extracting DHA from microalgae based on biimidazole ionic liquid.
Background
DHA (docosahexaenoic acid), commonly known as brain gold, is a polyunsaturated fatty acid very important for human body, and belongs to an important member of Omega-3 unsaturated fatty acid family. DHA has a plurality of important nutritional functions, is an important component for constituting higher animal cells, and can have special prevention and treatment effects on cardiovascular diseases, such as: (1) beneficial to brain and vision development in infants; (2) beneficial to cardiovascular health; (3) beneficial for the prevention and treatment of cancer; (4) to aid in the treatment of psychotic disorders. With the increasing demand of the fish oil, the fish oil is only used as a production source, which can not meet the demand, and has the problems of low yield, easy oxidation, heavy fishy smell and the like. The world seaweed resources are rich, the marine algae and DHA content in some plankton are rich. The coastline of China is long, the sea area is wide, seaweed resources are rich, but the seaweed creation value is low, the seaweed resources are developed and comprehensively utilized, and the economic value and the utilization value of the seaweed are improved.
CN10378764a discloses a method for extracting DHA from marine microalgae fermentation broth, which adopts the technological steps of enzymatic wall breaking treatment, centrifugal separation and extraction of crude oil, refining and purification, and the like to extract DHA. However, the process is complex, the refining and purification are needed, and the processes of degumming, deacidification, decoloration, deodorization and the like are not suitable for industrial production.
CN113480425B discloses a process for extracting DHA and EPA from microalgae, comprising the following steps: (1) microalgae cultivation; (2) crushing the raw materials; (3) enzymolysis; (4) sedimentation separation; (5) extraction; and (6) separating and purifying. However, the yield of the method is about 30%, the total content of DHA and EPA in the obtained product is about 80%, and the yield and purity are lower.
CN104388178a discloses a method for extracting DHA algae oil from algae cells, comprising the following steps: (1) Centrifuging and spray-drying an alga cell fermentation liquid to prepare alga cell dry powder, uniformly mixing the alga cell dry powder with absolute ethyl alcohol, and then carrying out high-pressure homogenizing wall breaking to prepare a wall-broken ethanol solution; (2) Evaporating the wall-broken ethanol solution at low temperature under vacuum, and removing ethanol to obtain wall-broken thallus; (3) Taking the wall-broken thalli, and carrying out CO2 supercritical extraction to obtain DHA algae oil. However, the supercritical gas extraction method has large equipment investment, high technical requirements and large energy consumption.
In conclusion, the prior art generally has the problems of low extraction rate and purity, complex process, high requirements on equipment and the like. Therefore, there is a need to provide a new method for extracting DHA, which has high extraction rate and high purity and is suitable for industrial production.
Disclosure of Invention
The invention aims to provide a method for extracting DHA from microalgae, which aims to solve the problems of low extraction rate and purity, complex process and the like in the prior art.
In order to solve the technical problems, the invention provides the following technical scheme:
The method for selectively extracting DHA from microalgae based on the biimidazole ionic liquid is characterized by comprising the following steps:
1) Taking microalgae grease as a raw material, adding an alkaline alcohol solution, and heating and refluxing; adding deionized water and bisimidazole ionic liquid, standing and layering;
2) And taking the lower layer solution, adding acid to adjust the pH value, extracting by using an organic solvent, drying, and concentrating under reduced pressure to obtain a DHA algae oil finished product.
In some embodiments, the structural general formula of the bisimidazole ionic liquid is as follows:
wherein X is Cl, br, I, BF 4、CF3SO3; Z1、Z2 independently selected from C1-C6 straight or branched alkyl, phenyl, benzyl.
In some embodiments, the Z 1、Z2 is independently selected from methyl, ethyl, propyl, phenyl, and benzyl, preferably the Z 1、Z2 is independently selected from methyl, ethyl, and benzyl.
In some embodiments, the bisimidazole-based ionic liquid is:
、/>
In some embodiments, the base of step 1) is NaOH, KOH, na 2CO3 or K 2CO3, preferably NaOH, KOH.
In some embodiments, the alcohol of step 1) is methanol or ethanol, preferably methanol.
In some embodiments, step 1) the microalgae lipid is preferably schizochytrium limacinum crude oil; the acid in the step 2) is dilute hydrochloric acid or dilute sulfuric acid, and the pH is 1-4.
In some embodiments, step 1) the heating temperature is 30-60 ℃, preferably 40-50 ℃; the heating time is 1 to 5 hours, preferably 1 to 3 hours.
In some embodiments, the alcohol solution of the base has a concentration of 0.5mol/L to 1.5mol/L; the volume ratio of deionized water to the bisimidazole ionic liquid is as follows: 1 to 5.
In some embodiments, the organic solvent of step 2) is selected from the group consisting of dichloromethane, chloroform, acetone, ethanol, and petroleum ether, preferably chloroform and petroleum ether.
The post-treatment operation of the present invention, such as drying, concentrating under reduced pressure, may employ an operation method conventional in the art.
The invention has the following beneficial effects:
1) The bisimidazole ionic liquid adopted by the invention can be used for selectively extracting DHA in microalgae, and has high extraction rate and purity and good selectivity.
2) The DHA algae oil finished product with high purity can be obtained by simple extraction, the purity can reach 90%, the cost is low, the safety is good, and the method has good industrial production application prospect.
Detailed Description
The technical solutions of the present invention will be clearly and completely described in connection with the embodiments, and it is apparent that the described embodiments are some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The invention is further illustrated with reference to specific embodiments.
Example 1
100G of schizochytrium limacinum crude oil (obtained by a squeezing method, purchased from Xiamen Huiyun biological Co., ltd., gas chromatography analysis, DHA content of the crude oil of 18.72%) is taken, placed in a flask, 100mL of 0.5mol/L NaOH-methanol solution is added, and heated and refluxed at 50℃for 2 hours. Then 50mL deionized water and 200mL ionic liquid were addedStanding for layering, and removing the upper unsaponifiable matter. And (3) taking the lower layer solution, adding dilute HCl to adjust the pH value to be 2.0, extracting with petroleum ether (500 ml x 3), combining ether layer organic phases, drying with anhydrous sodium sulfate, concentrating under reduced pressure to obtain a DHA algae oil finished product, and detecting by gas chromatography, wherein the DHA content in the product is 90.6%, and the extraction rate is 85.7%.
Example 2
100G of schizochytrium limacinum crude oil (obtained by a squeezing method, purchased from Xiamen Huiyun biological Co., ltd., gas chromatography analysis, DHA content of the crude oil of 18.72%) is taken, placed in a flask, 100ml of 1.0mol/L NaOH-methanol solution is added, and heated and refluxed at 40 ℃ for 1h. Then 50mL deionized water and 300mL ionic liquid were addedStanding for layering, and removing the upper unsaponifiable matter. And (3) taking the lower layer solution, adding dilute HCl to adjust the pH to be 2.5, extracting with petroleum ether (500 ml x 3), combining ether layer organic phases, drying with anhydrous sodium sulfate, concentrating under reduced pressure to obtain a DHA algae oil finished product, and detecting by gas chromatography, wherein the DHA content in the product is 91.3%, and the extraction rate is 85.2%.
Example 3
100G of schizochytrium limacinum crude oil (obtained by a squeezing method, purchased from Xiamen Huiyun biological Co., ltd., gas chromatography analysis, wherein DHA content in the crude oil is 18.72%) is put into a 1.0L flask, 50mL of 0.5mol/L NaOH-methanol solution is added, and the mixture is heated and refluxed at 45 ℃ for 3 hours. Then 50mL deionized water and 400mL ionic liquid were addedStanding for layering, and removing the upper unsaponifiable matter. And (3) taking the lower layer solution, adding dilute HCl to adjust the pH to be 3.0, extracting with petroleum ether (500 ml x 3), combining ether layer organic phases, drying with anhydrous sodium sulfate, concentrating under reduced pressure to obtain a DHA algae oil finished product, and detecting by gas chromatography, wherein the DHA content in the product is 90.8%, and the extraction rate is 87.6%.
Example 4
100G of schizochytrium limacinum crude oil (obtained by a squeezing method, purchased from Xiamen Huiyun biological Co., ltd., content of DHA in the crude oil being 18.72%) is taken, placed in a 1.0L flask, 100mL of 0.5mol/L NaOH-ethanol solution is added, and heated and refluxed at 40℃for 2 hours. Then 50mL deionized water and 350 mL ionic liquid are addedStanding for layering, and removing the upper unsaponifiable matter. And (3) taking the lower layer solution, adding dilute HCl to adjust the pH to be 3.0, extracting with chloroform (500 mL 3), combining chloroform organic phases, drying with anhydrous sodium sulfate, concentrating under reduced pressure to obtain a DHA algae oil finished product, and detecting by gas chromatography, wherein the DHA content in the product is 90.5%, and the extraction rate is 86.1%.
Comparative example 1
100G of schizochytrium limacinum crude oil (obtained by a squeezing method, purchased from Xiamen Huiyun biological Co., ltd., gas chromatography analysis, DHA content of the crude oil of 18.72%) is taken, placed in a flask, 100mL of 0.5 mL NaOH-methanol solution is added, and heated and refluxed at 50℃for 2 hours. 200mL of deionized water was then added, and the layer was allowed to stand to remove the upper unsaponifiable material. And (3) taking the lower layer solution, adding dilute HCl to adjust the pH value to be 2.0, extracting with petroleum ether (500 ml x 3), combining ether layer organic phases, drying with anhydrous sodium sulfate, concentrating under reduced pressure to obtain a DHA algae oil finished product, and detecting by gas chromatography, wherein the DHA content in the product is 38.4%, and the extraction rate is 35.1%.
Comparative example 2
100G of schizochytrium limacinum crude oil (obtained by a squeezing method, purchased from Xiamen Huiyun biological Co., ltd., gas chromatography analysis, DHA content of the crude oil of 18.72%) is taken, placed in a flask, 100mL of 0.5 mL NaOH-methanol solution is added, and heated and refluxed at 50℃for 2 hours. Then 50mL of deionized water and 200mL of the ionic liquid 1-butyl-3 methylimidazole tetrafluoroborate were addedStanding for layering, and removing the upper unsaponifiable matter. And (3) taking the lower layer solution, adding dilute HCl to adjust the pH value to be 2.0, extracting with petroleum ether (500 ml x 3), combining ether layer organic phases, drying with anhydrous sodium sulfate, concentrating under reduced pressure to obtain a DHA algae oil finished product, and detecting by gas chromatography, wherein the DHA content in the product is 55.1%, and the extraction rate is 65.3%.
The above examples are presented for clarity of illustration only and are not limiting of the embodiments. Other variations or modifications of the above teachings will be apparent to those of ordinary skill in the art. It is not necessary here nor is it exhaustive of all embodiments. And thus obvious variations or modifications to the disclosure are within the scope of the invention.
Claims (4)
1. The method for selectively extracting DHA from microalgae based on the biimidazole ionic liquid is characterized by comprising the following steps:
1) Adding an alcohol solution of alkali into schizochytrium limacinum crude oil serving as a raw material, and heating and refluxing; adding deionized water and bisimidazole ionic liquid, standing and layering;
2) Taking the lower layer solution, adding acid to adjust the pH value, extracting by using an organic solvent, drying, and concentrating under reduced pressure to obtain a DHA algae oil finished product;
the structure of the bisimidazole ionic liquid is one of the following compounds:
、/>
；
the base is NaOH, KOH, na 2CO3 or K 2CO3; the alcohol is methanol or ethanol;
the organic solvent in step 2) is selected from dichloromethane, chloroform, acetone, ethanol and petroleum ether.
2. The method according to claim 1, characterized in that:
The acid in the step 2) is dilute HCl or dilute sulfuric acid, and the pH value is 1-4.
3. The method according to claim 1, characterized in that:
The heating temperature of the step 1) is 30-60 ℃, and the heating time is 1-5 h.
4. The method according to claim 1, characterized in that:
The concentration of the alcohol solution of the alkali is 0.5 mol/L-1.5 mol/L; the volume ratio of deionized water to the bisimidazole ionic liquid is as follows: 1 to 5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311374575.5A CN117486713B (en) | 2023-10-23 | Method for selectively extracting DHA from microalgae based on bisimidazole ionic liquid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311374575.5A CN117486713B (en) | 2023-10-23 | Method for selectively extracting DHA from microalgae based on bisimidazole ionic liquid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN117486713A CN117486713A (en) | 2024-02-02 |
| CN117486713B true CN117486713B (en) | 2024-06-25 |
Family
ID=
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103396303A (en) * | 2013-07-25 | 2013-11-20 | 浙江大学 | Method for separating and purifying eicosapentaenoic acid and docosahexaenoic acid from micro-algal oil or fish oil |
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103396303A (en) * | 2013-07-25 | 2013-11-20 | 浙江大学 | Method for separating and purifying eicosapentaenoic acid and docosahexaenoic acid from micro-algal oil or fish oil |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105482890B (en) | A kind of method of microwave-ultrasonic auxiliary extracting linseed oil by water-enzyme process | |
| KR102148333B1 (en) | Method for continuously enriching an oil produced by microalgae with ethyl esters of dha | |
| CN104651422B (en) | A kind of method that triglyceride type DHA and EPA are extracted from deep-sea fish | |
| CN101092344B (en) | Method for extracting nervonic acid from oil of Mono Maple by using technique of molecular distillation | |
| CN112592268B (en) | Method for separating EPA (eicosapentaenoic acid) in fish oil by using continuous chromatographic system | |
| CN111406110A (en) | Preparation of algae polyunsaturated fatty acids | |
| CN101481297A (en) | Method for refining biodiesel by-product glycerol | |
| CN111848341A (en) | Method for separating and purifying nervonic acid in acer truncatum buge oil by combining molecular distillation with urea inclusion method | |
| CN102320953B (en) | Method for preparing natural alpha-linolenic acid from crude oil of idesia polycarpa var.vestita diels | |
| CN106966902A (en) | A kind of preparation method of alpha linolenic acid ethyl ester | |
| CN105132189B (en) | A kind of fine separation method of C18 series and C20~C22 series fatty acid methyl esters | |
| CN108084020B (en) | Method for preparing omega-7 fatty acid ester by using grease as raw material | |
| CN103396303B (en) | Method for separating and purifying eicosapentaenoic acid and docosahexaenoic acid from micro-algal oil or fish oil | |
| CN103013653B (en) | Preparation method of refined egg oil | |
| CN105779140A (en) | Preparation method of ethyl ester type fish oil with high EPA content | |
| CN117486713B (en) | Method for selectively extracting DHA from microalgae based on bisimidazole ionic liquid | |
| CN111635308B (en) | Method for co-producing and preparing linoleic acid and alpha-linolenic acid from idesia polycarpa seed oil | |
| CN102887821A (en) | Method for extracting DHA (docosahexaenoic acid) through extraction and separation of marine microalgae fermentation liquid | |
| CN106590939A (en) | Method for purification preparation of high content linoleic acid by using vegetable oil as raw material | |
| CN111690462A (en) | Method for demulsifying and extracting oil from oil-containing algae or fungus cell wall-broken liquid | |
| CN117486713A (en) | Method for selectively extracting DHA from microalgae based on bisimidazole ionic liquid | |
| CN103865642B (en) | A kind of preparation method of non-solvent high purity DHA algal oil | |
| CN103864614B (en) | The method of separation and purification DHA-EE from the DHA grease of fermentable | |
| CN111205179A (en) | Method for comprehensively extracting EPA and fucoxanthin from Phaeodactylum tricornutum | |
| CN107162910B (en) | Method for preparing high-purity EPA-EE from fish oil |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant |