CN113603733B - Preparation of glycolipid type ionic liquid and application of glycolipid type ionic liquid in glycolipid separation process - Google Patents
Preparation of glycolipid type ionic liquid and application of glycolipid type ionic liquid in glycolipid separation process Download PDFInfo
- Publication number
- CN113603733B CN113603733B CN202110908046.3A CN202110908046A CN113603733B CN 113603733 B CN113603733 B CN 113603733B CN 202110908046 A CN202110908046 A CN 202110908046A CN 113603733 B CN113603733 B CN 113603733B
- Authority
- CN
- China
- Prior art keywords
- rhamnolipid
- ionic liquid
- glycolipid
- hours
- acid
- 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
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/03—Monoamines
- C07C211/07—Monoamines containing one, two or three alkyl groups, each having the same number of carbon atoms in excess of three
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/35—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing only non-condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- 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
- 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
- C07C2601/14—The ring being saturated
-
- 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
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Abstract
The invention provides a glycolipid type ionic liquid prepared by using rhamnolipid fermentation liquor, and a preparation process and application thereof. The preparation process comprises the following steps: filtering the rhamnolipid fermentation liquor to obtain rhamnolipid sterile liquor; adding acid into the sterile liquid, and collecting precipitate to obtain solid rhamnolipid; mixing rhamnolipid with a dialkylamine compound, adding a solvent, standing for layering, and separating to obtain rhamnolipid ionic liquid. The ionic liquid disclosed by the invention is novel in structure, has the advantages of chemical inertness, high boiling point and good conductivity of the ionic liquid, particularly has high solubility and stability on glycolipid, is insoluble with water, and enables the separation of the glycolipid from fermentation liquor to be simpler, thereby greatly reducing the difficulty of separation and purification of the glycolipid.
Description
Technical Field
The invention belongs to the field of fermentation engineering, and particularly relates to preparation of a glycolipid type ionic liquid and application of the glycolipid type ionic liquid in a glycolipid separation process.
Background
The rhamnolipid is mainly generated by metabolism of pseudomonas aeruginosa in a certain environment, has good surface activity and interfacial activity, and can be widely applied to the fields of petrochemical industry, environment, medicine, food, agriculture and the like; the biological surfactant has the advantages of no toxicity and biodegradability, and is the biological surfactant with the longest research time, the best effect and the most mature application technology.
The rhamnolipid fermentation liquor, in particular to rhamnolipid fermentation liquor, contains fermentation thalli, protein, inorganic salt and other impurities besides rhamnolipid, generally obtains a rhamnolipid crude product through centrifugal sterilization and acid precipitation, and then obtains a rhamnolipid high-purity product through extraction, membrane separation, column chromatography and the like. The production cost is high and the wide application in the high-end field is limited to a great extent.
The ionic liquid is a material widely applied in the fields of organic synthesis, extraction separation, electrochemistry, catalysis discipline, nano material preparation, environmental science and the like, and has the characteristics of good chemical inertness, zero vapor pressure, wide liquid range, good ionic conductivity and thermal conductivity, high heat capacity and thermal energy storage density, high thermal stability and the like. The material is applied to the rhamnolipid separation process, reduces the rhamnolipid separation difficulty and separation cost, and has the significance of industrialized implementation.
Ionic liquids are of various types and suitable for fermentation systems, in particular for glycolipid separation systems, and are not yet seen in the market at present. Only the use of ionic liquids as extractants has been reported, the subsequent treatments are complicated and the process is not simplified.
In summary, a new process method suitable for separating the glycolipid fermentation broth needs to be developed at present, and the problems of high separation difficulty, complex process and high production cost are solved.
Disclosure of Invention
The invention aims to provide a glycolipid ionic liquid, which solves the problems of high production cost of rhamnolipid caused by the large separation difficulty of glycolipid fermentation liquor and complex separation process in the prior art.
The invention realizes the aim by the following technical scheme:
a rhamnolipid type ionic liquid, the ionic liquid having the structure:
wherein R is 1 And R is 2 Is one of n-butyl, n-amyl, n-hexyl, n-heptyl, n-octyl, cyclopentyl and cyclohexyl respectively, R 1 And R is 2 R, which may be identical or different, R 3 Is rhamnose monosaccharide di-fat base and/or rhamnose disaccharide di-fat base, and the structures are respectively as follows:
the invention further aims at providing a preparation method of the rhamnolipid type ionic liquid.
A method of preparing the rhamnolipid ion liquid, the method comprising the steps of:
s1: filtering the rhamnolipid fermentation liquor to obtain rhamnolipid sterile liquor;
s2: adding acid into the sterile liquid, and collecting precipitate to obtain solid rhamnolipid;
s3: mixing rhamnolipid with a dialkylamine compound, adding a solvent, standing for layering, and separating to obtain rhamnolipid ionic liquid.
In the invention, the S1 is filtered by a ceramic membrane; preferably, the ceramic membrane has a pore size of 20-500nm, preferably 50-200nm.
In the invention, 0.1 to 1 weight percent of acid is added into the S2, the mixture is stirred for 1 to 3 hours at room temperature, and the stirring is stopped after a large amount of precipitation occurs, and the mixture is kept stand for 1 to 2 hours; preferably, the acid is sulfuric acid.
In the invention, S2 uses a suction filtration or filter pressing mode to collect sediment; preferably, the pore diameter of the filter cloth used for suction filtration or pressure filtration is 20-50 μm; the filter cloth is made of one of nylon, polypropylene and dimethyl sulfoxide.
In the invention, the rhamnolipid in the S3 is mixed with the alkylamine compound in equal mass.
In the present invention, the S3 is heated to 50-80 ℃, preferably 55-60 ℃, kept for 1-2 hours and then cooled to room temperature.
In the invention, S3 is added with methylene dichloride of which the total mass is 1/5-1/3 of the mixture of rhamnolipid and alkylamine compound; after standing and layering, the upper layer is rhamnolipid secondary amine salt ionic liquid, and the lower layer is methylene dichloride solution containing rhamnolipid and dialkyl amine compound.
It is still another object of the present invention to provide a method for separating glycolipid compounds.
A method of separating a glycolipid compound using the rhamnolipid type ionic liquid, or a rhamnolipid type ionic liquid prepared using the preparation method, the separation method comprising the steps of:
SS1: adding rhamnolipid type ionic liquid into fermentation liquor to be separated containing glycolipid compounds;
SS2: adding acid into the mixture obtained in SS1, heating, cooling and layering;
SS3: separating out the ionic liquid containing glycolipid on the upper layer, cooling to crystallize and separate out the glycolipid, and filtering and collecting the crystal to obtain the high-purity glycolipid.
In the invention, the SS1 is added with 20-50 wt% of ionic liquid, preferably 20-30 wt% of ionic liquid, based on the mass of the fermentation broth.
In the present invention, the SS2 is added with 1wt% to 5wt% of an acid, preferably 2wt% to 3wt% of an acid, based on the mass of the mixture.
In the invention, the SS3 is heated to 30-40 ℃ and stirred for 1-2 hours; cooling to 0-20 ℃; preferably, the acid is hydrochloric acid.
In the invention, after the SS3 is layered, the upper layer is the ionic liquid containing glycolipid, and the lower layer is the high-salt fermentation liquid.
In the invention, the purity of the glycolipid obtained by the SS3 is more than 99 weight percent, and the yield is more than 90 weight percent; preferably, the glycolipid obtained from SS3 is a rhamnolipid.
In the invention, the SS3 is cooled to 0 ℃ to-20 ℃ and maintained for 4-20 hours, preferably 10-15 hours.
It is still another object of the present invention to provide a glycolipid compound.
A glycolipid compound obtained by separation treatment of the rhamnolipid type ionic liquid, or by separation treatment of the rhamnolipid type ionic liquid prepared by the preparation method, or by separation treatment of the separation glycolipid compound, preferably the glycolipid compound is a glycolipid compound prepared by a fermentation method, and more preferably the glycolipid compound is rhamnolipid prepared by a fermentation method.
Compared with the prior art, the technical scheme of the invention has the following advantages:
(1) The ionic liquid disclosed by the invention is novel in structure, has the advantages of chemical inertness, high boiling point and good conductivity of the ionic liquid, particularly has high solubility and stability on glycolipid, is insoluble with water, and enables the separation of the glycolipid from fermentation liquor to be simpler, thereby greatly reducing the difficulty of separation and purification of the glycolipid.
(2) The ionic liquid disclosed by the invention is simple in preparation process and environment-friendly in preparation process;
(3) The separation method is unique, the glycolipid is crystallized and separated in the ionic liquid, and the glycolipid is crystallized and separated out in the ionic liquid in a high-purity product form, so that the product yield is high, the purity is high, the process is simple, the process is green and environment-friendly, and the large-scale production can be realized.
Detailed Description
In the following examples and comparative examples of the present invention, the separation apparatus used was as follows: positive-pressure 1L filter, 20-500nm aperture of ceramic membrane of Jiugaozao, 0.5 square meter of effective filtering area, N-1100D-W of Japanese physicochemical rotary evaporator, 1-10L three-neck flask, shanghai refined macro water bath, and 1-5L separating funnel. Polypropylene filter cloth 20-50 μm, nylon filter cloth 20-50 μm and dimethyl sulfoxide filter cloth 20-50 μm.
The reagents, sources and purities used were as follows: dichloromethane, purchased from komiou, analytically pure; di-n-butylamine, analytically pure, purchased from chinese medicine, dicyclohexylamine, analytically pure, purchased from chinese medicine, di-n-octylamine, analytically pure, purchased from chinese medicine. Concentrated sulfuric acid with 98% content, analytically pure, 36.5% of concentrated hydrochloric acid and from Chinese medicine, wherein the rhamnolipid fermentation liquor is obtained by fermenting pseudomonas aeruginosa serving as engineering bacteria and glycerol and soybean oil serving as mixed carbon sources, and the sophorolipid fermentation liquor is obtained by fermenting glucose serving as a carbon source.
The detection method of rhamnolipid and sophorolipid content is sulfuric acid-anthrone method, and the specific operation method is as follows:
1) Preparing anthrone solution: 0.2g of anthrone is taken and dissolved in 100mL of sulfuric acid with the volume fraction of 80%, and the solution is protected from light for standby, is prepared at present and can not be stored.
2) Taking 0.5mL of sample to be measured in a 10-15mL test tube with a plug scale, placing the sample in an ice water bath for full cooling, keeping the ice water bath, adding 2mL of anthrone solution, quickly and uniformly mixing (reducing reaction as much as possible), then carrying out boiling water bath for 10min, taking out the sample to be measured, placing the sample into the ice water bath for cooling to room temperature, and measuring absorbance at 620 nm.
3) Murine Li Tangbiao curve: weighing 0.1g rhamnose to a 250mL volumetric flask, preparing 400mg/L of mouse Li Tangmu liquid, and then diluting in proportion to obtain standard samples with different concentrations, wherein the following table is provided:
| mother liquor (mL) | 0 | 0.2 | 0.4 | 0.6 | 0.8 | 1.0 |
| Pure water (mL) | 0.5 | 1.8 | 1.6 | 1.4 | 1.2 | 1 |
| Final concentration (mg/L) | 0 | 40 | 80 | 120 | 160 | 200 |
And measuring the absorbance value by an anthrone method, and drawing a standard curve.
y＝ax+b
Wherein y is rhamnose content, and x is absorbance.
The calculation formula of the final rhamnolipid content is as follows:
rhamnolipid content = content of rhamnose in reaction solution x dilution x 3.4.
4) Sophorolipid standard curve: the standard was changed to 99% pure glucose, and the other procedures were the same.
Example 1
The preparation process of the di-n-butylamine rhamnolipid ionic liquid comprises the following steps:
(1) 10kg of rhamnolipid fermentation broth is filtered and separated by using a 20nm ceramic membrane to obtain 7.5kg of degerming filtrate, 7.5g of concentrated sulfuric acid is added into the filtrate, and after stirring for 1 hour, precipitation is carried out, and the mixture is kept stand for 2 hours. The mixture was filtered through a 20 μm nylon filter cloth to collect 503g of solid.
(2) Mixing the obtained solid with the equal mass di-n-butylamine, transferring into a three-neck flask, heating to 50 ℃ under stirring for 1 hour, cooling to room temperature, adding 200g of dichloromethane, fully mixing, transferring into a separating funnel, standing for phase separation, and separating the upper layer, wherein the total amount of 857g is glycolipid type ionic liquid. The structure is as follows
Example 2
The preparation process of the di-n-octylamine glycolipid type ionic liquid comprises the following steps:
(1) 5kg of rhamnolipid fermentation broth is filtered and separated by using a 500nm ceramic membrane to obtain 4.5kg of degerming filtrate, 45g of concentrated sulfuric acid is added into the filtrate, and after stirring for 3 hours, precipitation is carried out, and the mixture is kept stand for 1.5 hours. A total of 305g of solids were collected by filtration through a 50 μm polypropylene filter cloth.
(2) Mixing the obtained solid with di-n-octylamine with equal mass, transferring into a three-neck flask, heating to 80 ℃ under stirring for 2 hours, cooling to room temperature, adding 203g of dichloromethane, fully mixing, transferring into a separating funnel, standing for phase separation, and separating the upper layer to 522g in total, thus obtaining the glycolipid type ionic liquid. The structure is as follows
Example 3
The preparation process of the dicyclohexylamine glycolipid type ionic liquid comprises the following steps:
(1) 3kg of rhamnolipid fermentation broth is filtered and separated by using a 200nm ceramic membrane to obtain 2.8kg of degerming filtrate, 14g of concentrated sulfuric acid is added into the filtrate, and after stirring for 2 hours, precipitation is carried out, and the mixture is kept stand for 1 hour. The mixture was filtered through 30 μm dimethyl sulfoxide filter cloth, and a total of 209g of solid was collected.
(2) Mixing the obtained solid with dicyclohexylamine with equal mass, transferring into a three-neck flask, heating to 60 ℃ under stirring for 1.5 hours, cooling to room temperature, adding 105g of dichloromethane, fully mixing, transferring into a separating funnel, standing for phase separation, separating the upper layer, and obtaining 389g in total of glycolipid type ionic liquid. The structure is as follows
Example 4
A process for separating rhamnolipid fermentation broth using the ionic liquid prepared in example 1, comprising the steps of:
1) 2kg of rhamnolipid fermentation liquor (containing 10.2% of rhamnolipid) is taken, 400g of the ionic liquid prepared in the example 1 is added, then 24g of concentrated hydrochloric acid is added, the temperature is raised to 30 ℃, stirring is carried out at 200rpm for 1 hour, then the temperature is reduced to 15 ℃, the mixture is transferred into a separating funnel to stand for 2 hours, separation is carried out, and 624g of upper layer liquid is collected.
2) The upper liquid was cooled to 0℃and kept for 4 hours, a large amount of crystals were crystallized out, and the solid was collected by filtration with a 20 μm-pore filter cloth to obtain 188g of solid, and the purity of rhamnolipid was 99.5% and the yield was 92% by content measurement.
Example 5
A process for separating rhamnolipid fermentation broth using the ionic liquid prepared in example 2, comprising the steps of:
1) 1.5kg of rhamnolipid fermentation broth (containing 9.12% of rhamnolipid) is taken, 750g of the ionic liquid prepared in the example 2 is added, then 75g of concentrated hydrochloric acid is added, the temperature is raised to 40 ℃, stirring is carried out at 500rpm for 2 hours, then the temperature is reduced to 20 ℃, the mixture is transferred into a separating funnel to stand for 2 hours, and the total of 887g of upper liquid is separated and collected.
2) The upper liquid was cooled to-20℃and kept for 20 hours, a large amount of crystals were crystallized out, and the solid was collected by filtration through a 20 μm-pore filter cloth to give 133g of solid, and the purity of rhamnolipid was 99.0% and the yield was 96.2% by content measurement.
Example 6
A process for separating rhamnolipid fermentation broth using the ionic liquid prepared in example 3, comprising the steps of:
1) 1kg of rhamnolipid fermentation liquor (containing 9.4% of rhamnolipid) is taken, 300g of the ionic liquid prepared in the example 3 is added, then 30g of concentrated hydrochloric acid is added, the temperature is raised to 35 ℃, stirring is carried out at 300rpm for 1.5 hours, then the temperature is reduced to 15 ℃, the mixture is transferred into a separating funnel to stand for 2 hours, and the total amount of the upper liquid is 389g after separation and collection.
2) The upper liquid was cooled to-5℃and kept for 10 hours, a large amount of crystals were crystallized out, and the solid was collected by filtration with a 50 μm-pore filter cloth to give 88g of a solid, and the purity of rhamnolipid was 99.6% and the yield was 93.2% by content measurement.
Example 7
A process for the separation of sophorolipid fermentation broth using the ionic liquid prepared in example 1, comprising the steps of:
1) 2kg of sophorolipid fermentation liquor (containing 35.7% of sophorolipid) is taken, 500g of the ionic liquid prepared in the example 1 is added, then 100g of concentrated sulfuric acid is added, the temperature is raised to 40 ℃, stirring is carried out at 300rpm for 2 hours, then the temperature is lowered to 20 ℃, the mixture is transferred into a separating funnel to stand for 2 hours, separation is carried out, and the total upper layer liquid is collected to be 1200g.
2) The upper liquid was cooled to-10℃and kept for 8 hours, a large amount of crystals were precipitated, and the solid was collected by filtration through a 50 μm-pore-size filter cloth to give 699g of a solid, whose purity was 99.0% and yield was 96.9% as determined by content.
Comparative example 1
The conventional separation process of rhamnolipid is as follows for comparison with separation yield and purity using ionic liquids.
5kg of rhamnolipid fermentation liquor, wherein the content of rhamnolipid is 9.5%, thalli and clear liquid are centrifugally separated, the centrifugal condition is a separation factor 8000, the retention time is 3 minutes, 4.2kg of supernatant is obtained, 98% sulfuric acid is added to adjust the pH value to 2.5, then the mixture is kept stand for 8 hours, solids are centrifugally separated, the centrifugal condition is a separation factor 3000, the retention time is 1 minute, and 658g of solids is obtained, and the rhamnolipid is a crude rhamnolipid product. 700g of ethyl acetate is added into the crude rhamnolipid product for extraction, an organic phase and a water phase are separated, the organic phase is evaporated to dryness to obtain 502g of purified rhamnolipid, the purity is 75%, and the whole separation yield is 79.3%.
It is apparent that the above examples are given by way 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. While still being apparent from variations or modifications that may be made by those skilled in the art are within the scope of the invention.
Claims (16)
1. A rhamnolipid type ionic liquid, which is characterized by comprising the following structure:
wherein R is 1 And R is 2 Is one of n-butyl, n-amyl, n-hexyl, n-heptyl, n-octyl, cyclopentyl and cyclohexyl respectively, R 1 And R is 2 R, which may be identical or different, R 3 Is rhamnose monosaccharide di-fat base and/or rhamnose disaccharide di-fat base, and the structures are respectively as follows:
2. a process for preparing the rhamnolipid type ionic liquid of claim 1, characterized in that the process comprises the steps of:
s1: filtering the rhamnolipid fermentation liquor to obtain rhamnolipid sterile liquor;
s2: adding acid into the sterile liquid, and collecting precipitate to obtain solid rhamnolipid;
s3: mixing rhamnolipid with a dialkylamine compound, adding a solvent, standing for layering, and separating to obtain rhamnolipid ionic liquid.
3. The method of claim 2, wherein S1 is filtered using a ceramic membrane.
4. A method of producing according to claim 3, wherein the ceramic membrane has a pore size of 20 to 500nm.
5. The method according to claim 4, wherein the pore diameter of the ceramic membrane is 50-200nm.
6. The preparation method according to claim 2, wherein the S2 is added with 0.1wt% to 1wt% of acid, stirred at room temperature for 1 to 3 hours, stopped after a large amount of precipitation occurs, and left to stand for 1 to 2 hours;
and/or S2, collecting the precipitate by using a suction filtration or pressure filtration mode.
7. The method of claim 6, wherein the S2 acid is sulfuric acid;
s2, the aperture of filter cloth used for suction filtration or pressure filtration is 20-50 mu m; the filter cloth is made of one of nylon, polypropylene and dimethyl sulfoxide.
8. The preparation method according to claim 2, wherein the rhamnolipid in S3 is mixed with a dialkylamine compound in equal mass;
and/or heating the S3 to 50-80 ℃, keeping for 1-2 hours, and then cooling to room temperature;
and/or, adding 1/5-1/3 of dichloromethane into the S3; after standing and layering, the upper layer is rhamnolipid secondary amine salt ionic liquid, and the lower layer is methylene dichloride solution containing rhamnolipid and dialkyl amine compound.
9. The method of claim 8, wherein S3 is heated to 55-60 ℃.
10. A method for separating glycolipid compounds using the rhamnolipid type ionic liquid of claim 1, or prepared using the preparation method of any one of claims 2-9, characterized in that the separation method comprises the steps of:
SS1: adding rhamnolipid type ionic liquid into fermentation liquor to be separated containing glycolipid compounds;
SS2: adding acid into the mixture obtained in SS1, heating, cooling and layering;
SS3: separating out the ionic liquid containing glycolipid on the upper layer, cooling to crystallize and separate out the glycolipid, and filtering and collecting the crystal to obtain the target glycolipid.
11. The separation method according to claim 10, wherein the SS1 is added with 20wt% to 50wt% of the ionic liquid based on the mass of the fermentation broth.
12. The separation method according to claim 11, wherein the SS1 is added with 20wt% to 30wt% of the ionic liquid based on the mass of the fermentation broth.
13. The separation method according to claim 10, wherein the SS2 is added with 1wt% to 5wt% of an acid based on the mass of the mixture;
and/or, the SS2 is heated to 30-40 ℃ and stirred for 1-2 hours; cooling to 0-20 ℃;
and/or after the SS3 is layered, the upper layer is an ionic liquid containing glycolipid, and the lower layer is fermentation liquor;
and/or, the purity of the glycolipid obtained by the SS3 is more than 99 weight percent, and the yield is more than 90 weight percent.
14. The separation method according to claim 13, wherein the SS2 is added with 2wt% to 3wt% of an acid based on the mass of the mixture;
the acid of SS2 is hydrochloric acid;
the glycolipid obtained by SS3 is rhamnolipid.
15. The separation method according to claim 10, wherein the SS3 is cooled to 0 ℃ to-20 ℃ for 4-20 hours.
16. The separation method of claim 15, wherein the SS3 is maintained for 10-15 hours after cooling.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110908046.3A CN113603733B (en) | 2021-08-09 | 2021-08-09 | Preparation of glycolipid type ionic liquid and application of glycolipid type ionic liquid in glycolipid separation process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110908046.3A CN113603733B (en) | 2021-08-09 | 2021-08-09 | Preparation of glycolipid type ionic liquid and application of glycolipid type ionic liquid in glycolipid separation process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN113603733A CN113603733A (en) | 2021-11-05 |
| CN113603733B true CN113603733B (en) | 2023-07-14 |
Family
ID=78340005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110908046.3A Active CN113603733B (en) | 2021-08-09 | 2021-08-09 | Preparation of glycolipid type ionic liquid and application of glycolipid type ionic liquid in glycolipid separation process |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113603733B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114213662B (en) * | 2021-12-16 | 2023-03-03 | 万华化学集团股份有限公司 | Rhamnolipid derivative and preparation method and application thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108949850B (en) * | 2018-08-01 | 2021-07-23 | 万华化学集团股份有限公司 | Online separation and purification method of rhamnolipid fermentation liquor |
-
2021
- 2021-08-09 CN CN202110908046.3A patent/CN113603733B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN113603733A (en) | 2021-11-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN113603733B (en) | Preparation of glycolipid type ionic liquid and application of glycolipid type ionic liquid in glycolipid separation process | |
| CN111349133B (en) | Acetylated mogrol and preparation method and application thereof | |
| CN107337593B (en) | Preparation method of coenzyme Q10 pure product | |
| CN111040050A (en) | Method for purifying sugammadex sodium | |
| CN113214210B (en) | Preparation method of dihydroquercetin | |
| CN105111253A (en) | Method for extracting and separating ganglioside | |
| CN105524129B (en) | A kind of preparation method of Etimicin Sulfate | |
| CN111423252A (en) | Comprehensive treatment method of rhamnolipid fermentation liquor | |
| CN102391259B (en) | Nifuratel compound and preparation method thereof | |
| CN109096129B (en) | Preparation method of L-carnitine tartrate | |
| CN109096347B (en) | Method for purifying high-purity 3,2 ', 6' -tri-N-acetyl gentamicin C1a alkali (P1) | |
| CN114031560B (en) | Preparation method of letermovir sodium salt | |
| CN111777650B (en) | Method for extracting and separating baicalin by using mixed micelle | |
| CN112457311B (en) | Preparation method of compound containing chloro-bromo-pyrrole-pyrimidone structure | |
| CN110606863B (en) | Preparation method of N-acetylneuraminic acid dihydrate | |
| CN109942643B (en) | Purification and separation method of sucrose fatty acid ester | |
| CN104163769B (en) | A kind of preparation method of chlorination propionyl-L-carnitine | |
| CN113214333A (en) | Preparation method of high-purity pleocidin | |
| CN108299538B (en) | Method for removing isoursodesoxycholic acid in duck bile | |
| CN106046020A (en) | Method of purifying nemadectin through crystallization | |
| CN117624267A (en) | Separation process of high-viscosity fermentation liquor under abnormal rhamnolipid working condition | |
| CN115466217B (en) | Method for recycling cyclic acid | |
| CN114957104A (en) | Novel crystal form of sodium picosulfate monohydrate and preparation method thereof | |
| CN113511967B (en) | Method for extracting quinic acid from ginkgo leaf extract chromatographic wastewater | |
| Wolfrom et al. | The 1, 5-Anhydride of 2, 3, 4, 6-Tetramethylglucose 1, 2-Enediol |
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 |