CN113444130B - Method for separating sugar ester in capsorubin extraction residues - Google Patents
Method for separating sugar ester in capsorubin extraction residues Download PDFInfo
- Publication number
- CN113444130B CN113444130B CN202110687786.9A CN202110687786A CN113444130B CN 113444130 B CN113444130 B CN 113444130B CN 202110687786 A CN202110687786 A CN 202110687786A CN 113444130 B CN113444130 B CN 113444130B
- Authority
- CN
- China
- Prior art keywords
- organic solvent
- capsorubin
- sugar ester
- extraction
- nanofiltration membrane
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/786—Separation; Purification; Stabilisation; Use of additives by membrane separation process, e.g. pervaporation, perstraction, reverse osmosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/573—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0096—Purification; Precipitation; Filtration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Abstract
The invention relates to the field of natural product extraction, in particular to a method for separating sugar ester in capsorubin extraction residues. The method comprises the steps of dissolving capsorubin extraction residues in an organic solvent, and separating sugar ester by an organic solvent-resistant nanofiltration membrane; the organic solvent is ethyl acetate, plant extraction solvent or acetone. The method can realize effective separation of sugar ester and impurity components in the capsanthin extraction residues, can realize effective purification of the sugar ester by one-step operation, has simple steps and low energy consumption, and is easy to realize industrial continuous production.
Description
Technical Field
The invention relates to the field of natural product extraction, in particular to a method for separating sugar ester in residual liquid of capsorubin extraction.
Background
The sugar ester is obtained by esterifying a fatty acid with a compound having a plurality of hydroxyl groups such as glucose or sucrose. Sugar esters can be classified into monoesters, diesters, and triesters, depending on the degree of esterification. Most sugar esters are non-toxic, non-irritating and odorless, but fatty acid esters with less than twelve carbon atoms have a bitter taste. Sugar ester is a kind of nonionic biosurfactant, widely used in food, medicine and cosmetic industries, and part of sugar ester and its derivatives also have antitumor and antibacterial activities.
Sugar ester-containing by-products are produced during the production of capsanthin. For example, in the process of producing capsanthin by hydration degumming, the residual colloid water contains a large amount of sugar ester and other water-soluble substances, so that the viscosity and the precipitate are high, the fluidity is poor, and the treatment is difficult. In the existing production process of capsanthin, the yield of byproducts accounts for about 10 percent of the total capsanthin yield. If the sugar ester in the capsorubin byproduct can be extracted and further utilized, the additional value of the production of the capsorubin can be improved, but the method for separating the sugar ester in the prior art is generally complex and cannot be applied on a large scale.
Disclosure of Invention
In view of the above problems in the prior art, the present invention provides a method for separating sugar ester in residual liquid of capsorubin extraction, which is simple in operation.
The method comprises the steps of dissolving capsorubin extraction residues in an organic solvent, and separating sugar ester by an organic solvent-resistant nanofiltration membrane;
the organic solvent is ethyl acetate, plant extraction solvent or acetone.
The invention discovers for the first time that sugar esters in capsorubin extraction residues can be effectively separated from other components by processing the sugar esters by the method.
Preferably, the organic solvent resistant nanofiltration membrane is a composite membrane and comprises a base membrane and a separation layer, wherein the base membrane is made of polyacrylonitrile, and the separation layer is an organic silicone coating coated on the surface of the base membrane. The organic solvent resistant nanofiltration membrane has a good separation effect on sugar ester and the impurity components.
Preferably, the content of sugar ester in the capsorubin extraction residues is 38-45%, the viscosity is 50-1000 Pa.s, and the color value is 80-160.
Preferably, the residue of the capsanthin extract is prepared by the following method:
1) extracting the capsicum particles by using an organic solvent to obtain an extracting solution, and removing the organic solvent in the extracting solution to obtain a capsorubin crude product;
2) purifying the capsorubin crude product by a hydration degumming method, and taking a water solution containing colloid;
3) and extracting the aqueous solution containing the colloid by using an organic solvent to obtain an extract, and removing the organic solvent in the extract to obtain the capsorubin extraction residue.
Preferably, the organic solvent in the step 1) is one or two of acetone or n-hexane;
preferably, the mass ratio of the capsorubin crude product to the water in the step 2) is 1: 2-4;
preferably, the organic solvent in step 3) is ethyl acetate
The sugar ester content in the extraction residues is about 38-45%, the viscosity is 1000 Pa.s, the color value is 80-160, after the extraction residues are treated by an organic solvent-resistant nanofiltration membrane, the sugar ester enters a permeate liquid along with the membrane, after the organic solvent is removed by a trapped liquid, the sugar ester content is less than or equal to 10%, the viscosity is less than or equal to 200 P.s, the color value is 190-230, the quality of the product is similar to that of the capsanthin pigment obtained in the hydration degumming step, and the capsanthin pigment can be directly sold as a capsanthin product.
Preferably, the temperature of the system is controlled to be 0-40 ℃ in the process of passing through the organic solvent resistant nanofiltration membrane.
Further preferably, the temperature of the system is controlled to be 30-35 ℃.
Preferably, the operating pressure in the organic solvent resistant nanofiltration membrane treatment process is 1.3-2.8 MPa.
Further preferably, the temperature of the system is controlled to be 1.6-2.0 MPa.
Preferably, the mass percentage of the sugar ester mixture to be purified in the organic solvent is 3-30%. When the sugar ester content is low, the separation efficiency is low and the cost is high; when the sugar ester content is more than 30%, the viscosity of the feed liquid is high, the feed liquid is not easy to dissolve, the operation difficulty is increased, and the separation effect is poor.
The invention has the following beneficial effects:
1) the method can realize effective separation of sugar ester and impurity components in the capsanthin extraction residues, realizes effective purification of the sugar ester, has simple steps and low energy consumption, and is easy to realize industrial continuous production.
2) The invention has ideal purification effect on sugar ester, and the purity of the purified sugar ester can reach about 90 percent.
3) The method has the advantages that the purity and the concentration of the capsorubin in the residual liquid after the organic solvent resistant nanofiltration membrane is used are high, and the capsorubin can be directly sold as a product after the organic solvent is removed.
Detailed Description
The process of the invention is described below by means of specific embodiments. In addition, the embodiments should be considered illustrative, and not restrictive, of the scope of the invention, which is defined solely by the claims.
The capsorubin extraction residues referred to in the examples were prepared by the following method:
1) extracting the capsicum particles by using acetone to obtain an extracting solution, and evaporating to remove the acetone in the extracting solution to obtain a capsorubin crude product;
2) adding the capsorubin crude product into a mixture of 1: 3, adding water into the solid-to-liquid ratio to carry out hydration treatment, standing the mixed solution, and taking a water solution containing colloid after layering;
3) and (3) extracting the aqueous solution containing the colloid by using ethyl acetate through liquid-liquid extraction, standing and layering to obtain an organic phase, and concentrating to remove the ethyl acetate to obtain the capsorubin extraction residue.
Example 1
The embodiment relates to a method for separating sugar ester in capsorubin extraction residues, which comprises the following steps:
dissolving the capsorubin extraction residue 700g (color value 145.2, viscosity 685 Pa.s, sugar ester content 43.7%) in 10L ethyl acetate, and filtering to remove solid insoluble substance; putting the feed liquid into a feed liquid tank of an organic solvent-resistant nanofiltration membrane device, starting a power supply, operating the device, keeping the temperature of the feed liquid at 30-35 ℃ and the operating pressure at 1.6-2.1MPa in the separation process, circulating the feed liquid at the upstream side of the membrane, collecting primary permeate at the downstream side, and closing the device when the collection amount of the primary permeate is 7L; adding 6L of ethyl acetate into the feed liquid tank, performing secondary separation, starting the device, keeping the temperature at 30-35 ℃, operating pressure at 1.6-2.1MPa, collecting secondary permeate at the downstream, and closing the equipment when the collection amount of the secondary permeate is 6L; adding 6L of ethyl acetate into the feed liquid tank, performing three-time separation, starting the device, keeping the temperature at 30-35 ℃, operating pressure at 1.6-2.1MPa, collecting three-time permeate at the downstream, and closing the device and discharging trapped fluid when the collection amount of the three-time permeate is 6L.
Respectively concentrating the three permeate solutions and the trapped solution to obtain a final material, wherein the first permeate solution is 123.5g (color value is 23.4, sugar ester purity is 98.3%, and the final material is solidified after standing); 102.3g of secondary permeate (color value is 18.7, sugar ester purity is 97.4%, and solidification is carried out after standing); 62.3g of the third permeate (color value 9.3, sugar ester purity 96.2%, viscosity 1052pa · s), and the total yield of the sugar ester after the third purification is 91.85% by calculation.
411.9g of trapped fluid (color value 233.7, sugar ester content 6.1%, viscosity 185Pa s), which can be sold directly as capsorubin finished product after organic solvent is removed.
Example 2
The embodiment relates to a method for separating sugar ester in capsorubin extraction residues, which comprises the following steps:
dissolving 2100g of capsorubin extraction residue (color value 145.2, viscosity 685Pa · s, sugar ester content 43.7%) in 30L of ethyl acetate, and filtering to remove solid insoluble substances; putting the feed liquid into a feed liquid tank of an organic solvent-resistant nanofiltration membrane device, starting a power supply, operating the device, keeping the temperature of the feed liquid at 30-35 ℃ and the operating pressure at 1.6-2.1MPa in the separation process, circulating the feed liquid at the upstream side of the membrane, collecting primary permeate at the downstream side, and closing the device when the collection amount of the primary permeate is 21L; adding 18L of ethyl acetate into the feed liquid tank, performing secondary separation, starting the device, keeping the temperature at 30-35 ℃, operating pressure at 1.6-2.1MPa, collecting secondary permeate at the downstream, and closing the equipment when the collection amount of the secondary permeate is 18L; adding 18L of ethyl acetate into the feed liquid tank, performing three-time separation, starting the device, keeping the temperature at 30-35 ℃, operating pressure at 1.6-2.1MPa, collecting three-time permeate at the downstream, and closing the equipment when the collection amount of the three-time permeate is 18L; adding 18L of ethyl acetate into the feed liquid tank, separating for four times, starting the device, maintaining the temperature at 30-35 deg.C and the operating pressure at 1.6-2.1MPa, collecting the four times of permeate at downstream, and closing the device and discharging the trapped liquid when the collected amount of the four times of permeate is 18L.
Concentrating the four-time permeate and the trapped fluid respectively to obtain final material, wherein the first permeate is 370.5g (color value is 50.3, and sugar ester content is 98.2%, and then solidifying is carried out after standing); 306.9g of secondary permeating liquid (color value is 46.8, sugar ester content is 97.6 percent, and solidification is carried out after standing); 153.2g of third-time permeation liquid (color value 43.5, sugar ester content 96.8%, viscosity 1052Pa · s), 53.0g of fourth-time permeation liquid (color value 41.2, sugar ester content 95.2%, viscosity 602.3Pa · s); the total yield of sugar esters after four purifications was 93.94%.
1216.4g of trapped fluid (color value 216.5, sugar ester content 4.6%, viscosity 185Pa s). The trapped fluid can be directly sold as a capsorubin finished product after the organic solvent is removed.
Example 3
The embodiment relates to a method for separating sugar ester in capsorubin extraction residues, which comprises the following steps:
dissolving 700g (color value 145.2, viscosity 685 Pa.s and sugar ester content 43.7%) of capsorubin extraction residue in 10L of plant extraction solvent, and filtering to remove solid insoluble substance; putting the feed liquid into a feed liquid tank of an organic solvent-resistant nanofiltration membrane device, starting a power supply, operating the device, keeping the temperature of the feed liquid at 30-35 ℃ and the operating pressure at 1.6-2.1MPa in the separation process, circulating the feed liquid at the upstream side of the membrane, collecting primary permeate at the downstream side, and closing the device when the collection amount of the primary permeate is 7L; adding 6L of ethyl acetate into the feed liquid tank, performing secondary separation, starting the device, keeping the temperature at 30-35 ℃, operating pressure at 1.6-2.1MPa, collecting secondary permeate at the downstream, and closing the equipment when the collection amount of the secondary permeate is 6L; adding 6L of ethyl acetate into the feed liquid tank, performing three-time separation, starting the device, keeping the temperature at 30-35 ℃, operating pressure at 1.6-2.1MPa, collecting three-time permeate at the downstream, and closing the device and discharging trapped fluid when the collection amount of the three-time permeate is 6L.
Respectively concentrating the three permeate solutions and the trapped solution to obtain a final material, wherein the first permeate solution is 121.3g (color value is 24.5, sugar ester purity is 97.5%, and the final material is solidified after standing); 99.5g of secondary permeate (color value of 20.3, sugar ester purity of 96.5%, solidification after standing); 62.3g of the third permeate (color value 10.5, sugar ester purity 95.3%, viscosity 1052pa · s), and the total yield of the sugar ester after the third purification is 89.46% by calculation.
416.9g of trapped fluid (color value 232.5, sugar ester content 7.8%, viscosity 185Pa s), which can be sold directly as capsorubin finished product after organic solvent is removed.
Comparative example 1
Compared with example 1, the capsorubin extraction residue was dissolved using other organic solvents, and methanol solvent was used.
The result shows that the methanol has poor dissolving effect on the material to be separated, the solubility of the material to be separated is less than 1 percent, and the effective separation of residual sugar ester in capsorubin extraction residues cannot be realized through an organic solvent resistant nanofiltration membrane.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that modifications and improvements can be made thereto without departing from the scope of the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (3)
1. A method for separating sugar esters in capsorubin extraction residues is characterized by comprising the operation of dissolving the capsorubin extraction residues in an organic solvent and then separating the sugar esters through an organic solvent-resistant nanofiltration membrane;
the organic solvent is ethyl acetate, a plant extraction solvent or acetone;
the content of sugar ester in the capsorubin extraction residues is 38-45%, the viscosity is 500-1000Pa s, and the color value is 80-160;
the mass percentage of the sugar ester mixture to be purified in the organic solvent is 3-30%;
the organic solvent resistant nanofiltration membrane is a composite membrane and comprises a base membrane and a separation layer, wherein the base membrane is made of polyacrylonitrile, and the separation layer is an organic silicone coating coated on the surface of the base membrane;
the temperature of the system is controlled to be 0-40 ℃ in the process of passing through the organic solvent resistant nanofiltration membrane;
the operating pressure in the organic solvent resistant nanofiltration membrane treatment process is 1.3-2.8 Mpa;
the capsorubin extraction residue is prepared by the following method:
1) extracting the capsicum particles by using an organic solvent to obtain an extracting solution, and removing the organic solvent in the extracting solution to obtain a capsorubin crude product;
2) purifying the capsorubin crude product by a hydration degumming method, and taking a water solution containing colloid;
3) and extracting the aqueous solution containing the colloid by using an organic solvent to obtain an extract, and removing the organic solvent in the extract to obtain the capsorubin extraction residue.
2. The method as claimed in claim 1, wherein the temperature of the system is controlled to be 30-35 ℃ in the process of passing through the organic solvent-resistant nanofiltration membrane.
3. The method as claimed in claim 1 or 2, wherein the operating pressure in the organic solvent-resistant nanofiltration membrane treatment process is 1.6-2.0 MPa.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110687786.9A CN113444130B (en) | 2021-06-21 | 2021-06-21 | Method for separating sugar ester in capsorubin extraction residues |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110687786.9A CN113444130B (en) | 2021-06-21 | 2021-06-21 | Method for separating sugar ester in capsorubin extraction residues |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN113444130A CN113444130A (en) | 2021-09-28 |
| CN113444130B true CN113444130B (en) | 2022-07-12 |
Family
ID=77812060
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110687786.9A Active CN113444130B (en) | 2021-06-21 | 2021-06-21 | Method for separating sugar ester in capsorubin extraction residues |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113444130B (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105199009A (en) * | 2015-06-04 | 2015-12-30 | 石河子大学 | Method for preparing high-purity pectin by utilizing capsanthin colloidal waste |
| CN106726875A (en) * | 2016-11-24 | 2017-05-31 | 晨光生物科技集团股份有限公司 | A kind of preparation method of the extract of the material of class containing glycosyl sphingolipid |
| CN110713733A (en) * | 2019-10-29 | 2020-01-21 | 四川常青调正食品有限责任公司 | Process for separating capsanthin from hot pepper |
-
2021
- 2021-06-21 CN CN202110687786.9A patent/CN113444130B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105199009A (en) * | 2015-06-04 | 2015-12-30 | 石河子大学 | Method for preparing high-purity pectin by utilizing capsanthin colloidal waste |
| CN106726875A (en) * | 2016-11-24 | 2017-05-31 | 晨光生物科技集团股份有限公司 | A kind of preparation method of the extract of the material of class containing glycosyl sphingolipid |
| CN110713733A (en) * | 2019-10-29 | 2020-01-21 | 四川常青调正食品有限责任公司 | Process for separating capsanthin from hot pepper |
Also Published As
| Publication number | Publication date |
|---|---|
| CN113444130A (en) | 2021-09-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102161689B (en) | Method for extracting tea saponin from oil-tea-cake | |
| CN1951888A (en) | Process for purifying solanesol from tobacco leaf extract | |
| CN102001947A (en) | Method for preparing honeysuckle chlorogenic acid | |
| CN102181320A (en) | Extraction method of DHA (docosahexaenoic acid) algae oil by biological fermentation | |
| CN113648834B (en) | Ceramic membrane and preparation method and application thereof | |
| CN109320400B (en) | Method for extracting natural mannitol from waste liquid of mogroside production | |
| JP2013537888A (en) | Method for preparing Centella asiatica extract | |
| CN102617693B (en) | Method utilizing subcritical water extraction technology to extract and prepare ursolic acid from loquat leaves | |
| CN102267906B (en) | Extraction method for chlorogenic acid | |
| JP2018522065A (en) | Method for purifying ferulic acid and / or salt thereof | |
| CN113444130B (en) | Method for separating sugar ester in capsorubin extraction residues | |
| AU774470B2 (en) | Method for preparing aloin by extraction | |
| CN104788515B (en) | Method for preparing high-purity water-soluble oleuropein by reduced pressure ultrasonic-assisted extraction | |
| CN109053517B (en) | Method for extracting lutein from marigold | |
| CN103012512A (en) | Separation and purification method of salidroside in natural rhodiola sachalinensis | |
| CN110917240A (en) | Continuous method for separating multiple effective components from cyclocarya paliurus | |
| RU2524778C1 (en) | Method of producing betulin | |
| CN103571633B (en) | Esterification-ultra-high voltage Crystallization Separation the method for one vegetable oil overhead product | |
| CN114853593A (en) | Method for extracting high-purity nervonic acid from acer truncatum buge oil | |
| CN100509757C (en) | Purification method of *N-L-arginine | |
| CN108210554B (en) | Method for separating and purifying alcohol-soluble total flavonoids from liquorice | |
| CN103012535A (en) | Method for preparing refined cholesterol by separating cholesterol from egg oil | |
| US2557916A (en) | Preparation of a cardio-active glycoside | |
| CN105420293A (en) | Method for separating and purifying resveratrol from traditional Chinese medicine polygonum cuspidatum extraction solution | |
| CN111138433A (en) | Method for extracting and purifying matrine from sophora moorcroftianain |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |