CN103342820A - Method for extracting and separating polyehtylne glycol fatty acid monoester and diester - Google Patents
Method for extracting and separating polyehtylne glycol fatty acid monoester and diester Download PDFInfo
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Abstract
The invention discloses a method for extracting and separating polyehtylne glycol fatty acid monoester and diester. Monoester and diester are effectively separated from a mixture containing polyehtylne glycol fatty acid monoester and diester by taking a binary mixed solvent composed of water and hydrophilic ionic liquid or a binary mixed solvent composed of polarity organic solvent completely soluble in water and water as the extracting agent and taking ester or alcohol hydrophobic organic solvent with the water solubility less than or equal to 15 g per 100 g as the washing agent through a fractional distillation extraction method. The method disclosed by the invention has the advantages of being high in separation efficiency, low in solvent consumption, safe, environmentally-friendly, easy for industrial production and the like.
Description
Technical field
The present invention relates to chemical separation process, be specifically related to a kind of method of extracting and separating polyethylene glycol fatty acid list dibasic acid esters.
Background technology
Cithrol is a kind of nonionic surface active agent, and is nontoxic, tasteless, can be degraded fully by biology, is widely used in washing composition, makeup, weaving, agricultural, medicine and other fields.The synthetic method that cithrol is commonly used has two classes: the one, under alkaline condition, carry out ethoxylation with oxyethane and lipid acid, because oxyethane belongs to flammable and explosive substance, reaction needs to carry out in nitrogen protection and autoclave, and the control of the polymerization degree is difficult, and processing condition are comparatively harsh; The 2nd, carry out esterification or to carry out transesterification reaction synthetic with other fatty acid ester with polyoxyethylene glycol and lipid acid.The latter is safer, and the control of the polymerization degree is easier, so synthetic esterification or transesterification reactions of adopting of cithrol more.
Because two hydroxyl reactions of polyoxyethylene glycol are quite active, esterification or transesterification reaction can generate the mixture of polyethylene glycol fatty acid monoesters and dibasic acid esters.Even ethoxylation can generate the mixture of polyethylene glycol fatty acid list dibasic acid esters equally.In order to obtain the pure product of monoesters, can be by hydroxyl of selective protection during reaction, deprotection again after esterification finishes is as using hydroxyl of boric acid protection.This method is owing to long reaction time, and technology is loaded down with trivial details, less being used.Polyethylene glycol fatty acid monoesters on the market and the product of dibasic acid esters are mixture, be to obtain the relative higher a kind of ester of content as principal product by polyoxyethylene glycol in the conditioned reaction raw material and the ratio of lipid acid mostly, as add excessive acid and can generate the more relatively dibasic acid esters of content, add excessive polyoxyethylene glycol and can generate the higher relatively monoesters of content.
Because the monoesters of polyethylene glycol fatty acid is close with the dibasic acid esters textural property and all be to have the polymkeric substance that certain molecular weight distributes, separate and analysis has certain degree of difficulty.The product of existing polyethylene glycol fatty acid list dibasic acid esters on the market, wherein composition and content is not elaborated, and between the different manufacturers because raw material and production technique are not quite similar the relative content that causes single dibasic acid esters and molecular weight distribution different, so product confusion of polyethylene glycol fatty acid list dibasic acid esters on the market.The difference of single dibasic acid esters simultaneously is that the number of the hydrophobic substituent that links to each other with polyoxyethylene glycol is different, therefore surfactivity and the wetting ability of single dibasic acid esters have very big difference, the product that exists with form of mixtures is restricted in application facet, especially is restricted in the application to product composition and the content field of medicaments that there are strict requirements.Therefore adopting the method for separating to separate the pure product that obtain monoesters and dibasic acid esters from polyethylene glycol fatty acid list diester mixture has great importance to the foundation of single dibasic acid esters analytical procedure and follow-up application.
The report that optimization by reaction conditions increases monoester content as: it is catalyzer with the sodium methylate that international monopoly document WO 2007038025 has been announced a kind of, by the method for preheating polyvalent alcohol synthesis of high purity polyol monoesters before reacting; American documentation literature US3669848 has announced under 170 ℃～285 ℃, underpressure distillation, the method for highly selective synthesizing propanediol monoesters.More than the method that provides in two patent documentations at polyvalent alcohol, but it is inapplicable for the polyoxyethylene glycol that the polymerization degree is big slightly, because for the long polyoxyethylene glycol of chain length, behind the hydroxyl reaction of one end, hydroxyl to the other end does not almost have space steric effect, the hydroxyl that does not influence the other end carries out esterification, therefore is difficult to optionally only generate the polyethylene glycol fatty acid monoesters by the control reaction conditions.
American documentation literature US20090192329A1 has announced a kind of method of not using the catalyst to synthesize glycol fatty acid ester, wherein improves the method for single dibasic acid esters relative content for regulating ratio pure with sour in the raw material.
Because single dibasic acid esters similar, character approaches, the less separation problem of mentioning single dibasic acid esters in the document, and minority mentions that the method that single dibasic acid esters separates also mainly adopts chromatography or extraction process.Chromatography be a kind of in separation frequent adopted method, especially for the bigger system of separating difficulty.It is stationary phase with silica gel that Gerald J.Papariello (Journal of the American Oil Chemists ' Society, (1960), 37:396 – 399) etc. has reported a kind of, the method for gradient elution separation polyoxyethylene glycol oleic acid list dibasic acid esters.But chromatography exists the consumption of stationary phase and solvent big, the shortcoming that treatment capacity is limited.
Extraction process separate polyethylene glycol fatty acid list dibasic acid esters have equipment simple, easy to operate, be applicable to the characteristics of carrying out the continuity large-scale industrial production.Jia-heng Lei (Journal of Surfactants and Detergents, (2012), 15:117 – 121) etc. delivered a kind of method of using ethyl acetate/salt solution system extracting and separating polyoxyethylene glycol vinylformic acid list dibasic acid esters, but this method only is applicable to the separation of single dibasic acid esters that the carbon chain lengths of lipid acid is very short, does not have effect for the separation of the polyethyleneglycol dibasic acid esters of long chain fatty acid.
Summary of the invention
The invention provides a kind of method of extracting and separating polyethylene glycol fatty acid list dibasic acid esters, the binary mixed solvent that the binary mixed solvent that employing water, hydrophilic ionic-liquid, hydrophilic ionic-liquid and water are formed or water-soluble fully polar organic solvent and water are formed is extraction agent, environmental protection, be convenient to recycling, have broad application prospects; And this extracting process does not have particular requirement to the carbon chain lengths of lipid acid.
A kind of method of extracting and separating polyethylene glycol fatty acid list dibasic acid esters may further comprise the steps:
(1) be raw material with polyethylene glycol fatty acid list diester mixture, ester class or alcohols hydrophobic organic solvent with solubleness≤15g/100g in the water are made into stock liquid, the binary mixed solvent of forming with water, hydrophilic ionic-liquid, hydrophilic ionic-liquid and water or water-soluble fully polar organic solvent are extraction agent with the binary mixed solvent of water composition, used hydrophobic organic solvent is washing composition during with preparation raw material liquid, carries out fractionation extraction;
(2) the fractionation extraction device is divided into extraction section and washing section, extraction agent enters the fractionation extraction system from the extraction section first step, stock liquid enters the fractionation extraction system from the last step of extraction section, washing composition enters the fractionation extraction system from the first step of washing section, merge stock liquid at the washing section last step and enter extraction section together, extraction phase carries out counter current contact mutually with washing, flow out the extraction liquid that is rich in the polyethylene glycol fatty acid monoesters from the first step of washing section, flow out the raffinate of enrichment polyethylene glycol fatty acid dibasic acid esters from the first step of extraction section, collect extraction liquid and raffinate respectively;
(3) with extraction liquid through vacuum concentration, washing and drying, obtain polyethylene glycol fatty acid monoesters product, raffinate obtains polyethylene glycol fatty acid dibasic acid esters product through vacuum concentration, washing and drying.
The key of extraction and separation technology is selection of Extractant.
Because the textural difference of polyethylene glycol fatty acid list dibasic acid esters is two hydroxyls of polyoxyethylene glycol in the dibasic acid esters and all generates ester with fatty acid response, and the polyoxyethylene glycol in the monoesters has only a hydroxyl and fatty acid response to generate ester, the ratio of hydrophilic segment (polyoxyethylene glycol) and oleophilic moiety (lipid acid) in the contrast molecule, the surfactivity of monoesters and wetting ability all obviously are better than dibasic acid esters.As amphiphilic single dibasic acid esters bigger solubleness is arranged all in polar organic solvent, especially when the chain of lipid acid longer, during the large percentage of oleophilic moiety in molecule.When separating single dibasic acid esters with hydrophobic organic solvent with the water two-phase extraction, monoesters is lower at the partition ratio of aqueous phase, and adding ionic liquid or polar organic solvent can increase the distribution of monoesters in extraction phase, improves partition ratio and treatment capacity well.If be extraction agent with pure ionic liquid, having the ionic liquid that viscosity of il is big, consumption big even have is deficiencies such as solid at normal temperatures, therefore often needs to add the third solvent.The third solvent that adds should have good mutual solubility with ionic liquid, needs again to form two-phase system with the solvent of single dibasic acid esters.
As preferably, the ester class of solubleness≤15g/100g or alcohols hydrophobic organic solvent are methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butylacetate, pentyl acetate, hexyl acetate, heptyl acetate, octyl acetate, propyl carbinol, Pentyl alcohol, n-hexyl alcohol, n-Heptyl alcohol, n-Octanol, primary isoamyl alcohol, isooctyl alcohol, 2-hexanol, 2-enanthol or sec-n-octyl alcohol in the described water.
As preferably, described water-soluble polar organic solvent fully is methyl alcohol, ethanol, n-propyl alcohol, Virahol, dimethyl sulfoxide (DMSO), N, dinethylformamide or acetonitrile.
Polyethylene glycol fatty acid list dibasic acid esters favorable solubility in organic solvents such as methyl alcohol, ethanol, Virahol, propyl carbinol, n-Octanol, ethyl acetate, dimethyl sulfoxide (DMSO), but because the number difference of polyoxyethylene glycol two ends hydrophobic group in single dibasic acid esters, both wetting abilities have very big difference.Utilize both hydrophilic difference to make up binary mixed solvent that hydrophobic organic solvents and water, hydrophilic ionic-liquid, hydrophilic ionic-liquid and water forms or water-soluble fully polar organic solvent and carry out separating of single dibasic acid esters with the two-phase extraction system that binary mixed solvent that water is formed forms, have simple to operate, treatment capacity big, the characteristics of high efficiency separation.
Ionic liquid is by positively charged ion M
+And anion N
-Form, room temperature or near be liquid under the room temperature, at separation field as a class novel separating medium of green and noticeable.Adopt conventional organic solvents to compare with extraction agent, as extraction agent, have some unique character with ionic liquid:
1. You Yi thermostability and chemical stability almost do not have vapour pressure, and be non-volatile, not flammable, thereby help the safety and environmental protection of technology;
2. therefore ionic liquid internal cohesive energy height forms two-phase system easily;
3. ionic liquid also can and solute between produce multiple intermolecular interaction, as pi-pi bond, dipole-dipole interaction, hydrogen bond etc., therefore solute is had good solubility;
4. the zwitterion Adjustable structure of ionic liquid can be passed through the zwitterion structure of design ionic liquid to regulate the mode of action and the intensity of ionic liquid and solute, reaches specific separating effect.
As preferably, described ionic liquid is hydrophilic ionic-liquid, and is further preferred, positively charged ion M
+For having substituent imidazole type positively charged ion, have substituent pyridine type positively charged ion, have substituent quaternary phosphine type positively charged ion, have substituent piperidines type positively charged ion, have substituent quaternary ammonium cation or having a kind of in the substituent tetramethyleneimine type positively charged ion; Anion N
-A kind of in chlorion, bromide anion, iodide ion, tetrafluoroborate, trifluoroacetic acid root, trifluoromethanesulfonic acid root, ethylsulfonic acid root, dimethyl phosphate radical, diethyl phosphate radical, dihydrogen phosphate or the amino acid group.
As preferably, described substituting group is C
1～C
16Alkyl, in the hydroxyethyl one or both.
As preferably, described polyoxyethylene glycol molecular-weight average is between 200～20000.
As preferably, described lipid acid is saturated fatty acid (Saturated fatty acids, SFA), monounsaturated fatty acids (Monounsaturated fatty acids, MUFA) or polyunsaturated fatty acid (Polyunsaturated fatty acids, PUFA), described SFA is sad, capric acid, lauric acid, palmitinic acid or stearic acid; Described MUFA is Semen Myristicae oleic acid, Zoomeric acid or oleic acid; Described PUFA is timnodonic acid (EPA) or docosahexenoic acid (DHA).
As preferably, the total concn of single dibasic acid esters is 0.5 grams per liter～200 grams per liters in the described stock liquid.If the concentration of single dibasic acid esters is low excessively in the stock liquid, the raw material treatment capacity is little, and solvent loss is big, is unfavorable for the economy of technology; If the excessive concentration of single dibasic acid esters is unfavorable for effective separation of single dibasic acid esters in the stock liquid.
As preferably, the mass percent of the binary mixed extractant intermediate ion liquid that described hydrophilic ionic-liquid and water are formed is 1%～99%, and described water-soluble fully polar organic solvent is 1%～70% with the mass percent of the binary mixed extractant Semi-polarity organic solvent of water composition.The adding of ionic liquid or polar organic solvent can improve monoesters in the distribution of aqueous phase, makes it have suitable partition ratio, improves the selectivity to dibasic acid esters.
Described washing composition is solvent for use in the stock liquid, when polyethylene glycol fatty acid list dibasic acid esters is had better dissolving power, can form liquid-liquid two-phase system with extraction agent.
When carrying out fractionation extraction, take all factors into consideration factors such as quality product, production cost, as preferably, the volume flow ratio between extraction agent, washing composition, the stock liquid three is 2～15:1～5:1.
As preferably, the service temperature of described fractionation extraction is advisable with 10 ℃～70 ℃.If temperature is low excessively, the viscosity of extraction agent is bigger, and rate of mass transfer reduces, and is unfavorable for production operation; If temperature is too high, solvent evaporates is serious, then can reduce partition ratio and the selectivity of fractionation extraction.
Described fractionation extraction device comprises extraction section and washing section, and synoptic diagram as shown in Figure 1.Extraction agent enters the fractionation extraction system from the extraction section first step, stock liquid enters the fractionation extraction system from the last step of extraction section, washing composition enters the fractionation extraction system from the first step of washing section, merge stock liquid and enter extraction section together at the extraction section last step, extraction phase and washing counter current contact mutually flow out the raffinate of enrichment polyethylene glycol fatty acid dibasic acid esters from the first step of extraction section, collect raffinate, through after vacuum concentration-washing-drying, obtain polyethylene glycol fatty acid dibasic acid esters product.Flow out the extraction liquid of enrichment polyethylene glycol fatty acid monoesters from the first step of washing section, through after vacuum concentration-washing-drying, obtain polyethylene glycol fatty acid monoesters product.
Described fractionation extraction is multistage fractionation extraction, and as preferably, extraction section is two to eight grades, and washing section is two to eight grades.The progression of extraction section and washing section is more many, and the effect of fractionation extraction is more good, and the purity of the polyethylene glycol fatty acid list dibasic acid esters that obtains is more high, but too much progression can cause problems such as the production capacity decline, energy consumption increase, time lengthening of fractionation extraction again.
The content of the polyethylene glycol fatty acid monoesters that obtains through extraction separating method of the present invention is: purity 〉=98% relatively; The content of polyethylene glycol fatty acid dibasic acid esters is: relative purity 〉=98%.
The present invention adopts high performance liquid chromatography (HPLC) to analyze the content of polyethylene glycol fatty acid list dibasic acid esters, and HPLC concrete analysis condition is: the C30 post (4.6mm * 250mm, particle diameter 5 μ m,
Rpaqueous), 35 ℃ of column temperatures, moving phase is acetonitrile/water (9:1, v/v) (A), Virahol (B).When detector is UV-detector, gradient elution (100/0(A/B), 0～45min, 30/70(A/B), and 45～70min, v/v), flow velocity 0.8ml/min, wavelength are 205nm; When detector was the differential detector, twice gradient elution detected the content of single dibasic acid esters at twice respectively.
The method of calculation of yield and content are as follows among the present invention:
Monoester content in polyethylene glycol fatty acid monoesters yield %=(monoesters quality product * product)/(monoester content in raw materials quality * raw material) * 100%;
Dibasic acid esters content in polyethylene glycol fatty acid dibasic acid esters yield %=(dibasic acid esters quality product * product)/(dibasic acid esters content in raw materials quality * raw material) * 100%;
The content of monoesters or dibasic acid esters in the relative content %=(product)/(total content of single dibasic acid esters in the product) * 100%.
It is extraction agent that the present invention adopts binary mixed solvent that water, hydrophilic ionic-liquid, hydrophilic ionic-liquid and water forms or water-soluble fully polar organic solvent and the binary mixed solvent of water composition, polyethylene glycol fatty acid list dibasic acid esters is separated, the extraction agent that adopts not only is convenient to recycling, and than environmental protection, pollution to environment is few, has broad application prospects;
The present invention adopts the fractionation extraction technology, and the consumption of industrial chemicals less, production capacity height, cost be low;
Utilize method of the present invention, the single dibasic acid esters of extracting and separating from polyethylene glycol fatty acid list diester mixture, good separating effect, the relative content of gained list dibasic acid esters all reaches more than 98%, and the yield of single dibasic acid esters all reaches more than 90%.
Description of drawings
Fig. 1 is the fractionation extraction synoptic diagram.
Embodiment
Cetomacrogol 1000 oleic acid list diester mixture (wherein the quality percentage composition of monoesters, dibasic acid esters is respectively 31.5%, 65.3%) and ethyl acetate are made into the stock liquid of 15 grams per liters, with ethyl imidazol(e) a tetrafluoro borate ([EMIm] [BF
4])-water mixed solvent is extraction agent ([EMIm] [BF
4] mass percent is 40%), be washing composition with the ethyl acetate, extraction agent, washing composition, stock liquid three's volume flow ratio is 3:2.5:1, carries out fractionation extraction under 40 ℃ in the fractionation extraction device.Fractionation extraction is divided into extraction section and washing section, and extraction section is two-stage, and washing section is three grades.Extraction agent enters the fractionation extraction system from the extraction section first step, stock liquid enters the fractionation extraction system from the last step of extraction section, washing composition enters the fractionation extraction system from the first step of washing section, merge stock liquid at the washing section last step and enter extraction section together, extraction phase and washing counter current contact mutually, flow out the extraction liquid that is rich in the cetomacrogol 1000 oleic acid monoester from the first step of washing section, collect this extraction liquid; Flow out the raffinate of enrichment cetomacrogol 1000 Glycol Oleic Acid Ester from the first step of extraction section, collect this raffinate; Extraction liquid, raffinate are removed ethyl acetate through vacuum concentration, and again through washing deionizing liquid repeatedly, dewatering finally by drying obtains single dibasic acid esters respectively.
Analyze through HPLC, cetomacrogol 1000 oleic acid monoester relative content is 98.4% in the extraction liquid, and yield is 90.7%; Cetomacrogol 1000 Glycol Oleic Acid Ester relative content is 98.7% in the raffinate, and yield is 95.6%.
The single diester mixture of poly(oxyethylene glycol) 400 lauric acid (wherein the quality percentage composition of monoesters, dibasic acid esters is respectively 29.5%, 70.0%) and butylacetate are made into the stock liquid of 0.5 grams per liter, be extraction agent ([HPy] Br mass percent is 20%) with N-hexyl pyridinium tribromide salt ion liquid ([HPy] Br), be washing composition with the butylacetate, extraction agent, washing composition, stock liquid three's stream is than being 2:3.1:1, in the fractionation extraction device, carry out fractionation extraction under 10 ℃, fractionation extraction is divided into extraction section and washing section, extraction section is level Four, and washing section is three grades.Flow out the extraction liquid that is rich in poly(oxyethylene glycol) 400 lauric acid monoesters from the first step of washing section, flow out the raffinate of enrichment poly(oxyethylene glycol) 400 lauric acid dibasic acid esters from the first step of extraction section, collect extraction liquid and raffinate; Extraction liquid and raffinate are removed butylacetate through vacuum concentration, and again through washing deionizing liquid repeatedly, dewatering finally by drying obtains monoesters and dibasic acid esters respectively.
Analyze through HPLC, the relative content of poly(oxyethylene glycol) 400 lauric acid monoesters is 98.8% in the extraction liquid, and yield is 93.7%; The relative content of poly(oxyethylene glycol) 400 lauric acid dibasic acid esters is 98.9% in the raffinate, and yield is 98.6%.
Embodiment 3
Macrogol 2000 stearic acid list diester mixture (wherein the quality percentage composition of monoesters, dibasic acid esters is respectively 50.7%, 44.8%) and propyl carbinol are made into the stock liquid of 200 grams per liters, with tributyl ammonium villaumite ([HNBu
3] Cl)-water mixed solvent ([HNBu
3] the Cl mass percent is 99%) be extraction agent, be washing composition with the propyl carbinol, extraction agent, washing composition, stock liquid three's stream is than being 13:3.3:1, in the fractionation extraction device, carry out fractionation extraction under 50 ℃, fractionation extraction is divided into extraction section and washing section, and extraction section is Pyatyi, and washing section is two-stage.Flow out the extraction liquid that is rich in monoesters from the first step of washing section, flow out the raffinate of enrichment dibasic acid esters from the first step of extraction section, collect extraction liquid and raffinate; Extraction liquid and raffinate are removed propyl carbinol through vacuum concentration, and again through washing deionizing liquid repeatedly, dewatering finally by drying obtains monoesters and dibasic acid esters.
Analyze through HPLC, the relative content of Macrogol 2000 stearate monoesters is 99.4% in the extraction liquid, and yield is 91.7%; The relative content of Macrogol 2000 stearate is 98.7% in the raffinate, and yield is 96.0%.
Embodiment 4
Polyethylene Glycol-600 linolic acid list diester mixture (wherein the quality percentage composition of monoesters, dibasic acid esters is respectively 30.4%, 49.5%) and n-Octanol are made into the stock liquid of 60 grams per liters, with 1-butyl-2,3-methylimidazole fluoroform sulphonate ([BMMIm] [CF
3SO
3])-aqueous solution is extraction agent ([BMMIm] [CF
3SO
3] mass percent is 10%), be washing composition with the n-Octanol, extraction agent, washing composition, stock liquid three's stream is than being 15:5:1, in the fractionation extraction device, carry out fractionation extraction under 10 ℃, fractionation extraction is divided into extraction section and washing section, and extraction section is six grades, and washing section is eight grades.Flow out the extraction liquid that is rich in monoesters from the first step of washing section, flow out the raffinate of enrichment dibasic acid esters from the first step of extraction section, collect extraction liquid and raffinate; Extraction liquid, raffinate are removed n-Octanol through vacuum concentration, and again through washing deionizing liquid repeatedly, dewatering finally by drying obtains monoesters and dibasic acid esters.
Analyze through HPLC, the relative content of Polyethylene Glycol-600 linolic acid monoesters is 99.5% in the extraction liquid, and yield is 90.8%; The relative content of Polyethylene Glycol-600 linolic acid dibasic acid esters is 99.8% in the raffinate, and yield is 92.2%.
Embodiment 5
Polyoxyethylene glycol 1200 palmitinic acid list diester mixtures (wherein the quality percentage composition of monoesters, dibasic acid esters is respectively 48.7%, 50.1%) and methyl acetate are made into the stock liquid of 100 grams per liters, with 1-hydroxyethyl pyridine diethyl phosphate ([HOEtPy] [C
2H
5PO
4])-water mixed solvent ([HOEtPy] [C
2H
5PO
4] mass percent is 30%) be extraction agent, be washing composition with the methyl acetate, extraction agent, washing composition, stock liquid three's stream is than being 5.3:2:1, in the fractionation extraction device, carry out fractionation extraction under 50 ℃, fractionation extraction is divided into extraction section and washing section, and extraction section is two-stage, and washing section is level Four.Flow out the extraction liquid that is rich in monoesters from the first step of washing section, flow out the raffinate of enrichment dibasic acid esters from the first step of extraction section, collect extraction liquid and raffinate; Extraction liquid and raffinate are removed methyl acetate through vacuum concentration, and again through washing deionizing liquid repeatedly, dewatering finally by drying obtains monoesters and dibasic acid esters.
Analyze through HPLC, the relative content of polyoxyethylene glycol 1200 palmitinic acid monoesters is 98.7% in the extraction liquid, and yield is 93.8%; The relative content of polyoxyethylene glycol 1200 palmitinic acid dibasic acid esters is 99.3% in the raffinate, and yield is 96.8%.
Embodiment 6
Polyethylene Glycol-600 capric acid list diester mixture (wherein the quality percentage composition of monoesters, dibasic acid esters is respectively 22.8%, 63.6%) and n-Heptyl alcohol are made into the stock liquid of 2 grams per liters, with N, N, N-trimethylammonium-N-Bing Ji Phosphonium lysine salt ([P
3111] [Lys])-water mixed solvent ([P
3111] [Lys] mass percent is 55%) be extraction agent, be washing composition with the n-Heptyl alcohol, extraction agent, washing composition, stock liquid three's stream is than being 4:1.5:1, in the fractionation extraction device, carry out fractionation extraction under 35 ℃, fractionation extraction is divided into extraction section and washing section, extraction section is level Four, and washing section is two-stage.Flow out the extraction liquid that is rich in monoesters from the first step of washing section, flow out the raffinate of enrichment dibasic acid esters from the first step of extraction section, collect extraction liquid and raffinate; Extraction liquid, raffinate are removed n-Heptyl alcohol through vacuum concentration, and again through washing deionizing liquid repeatedly, dewatering finally by drying obtains monoesters and dibasic acid esters.
Analyze through HPLC, the relative content of Polyethylene Glycol-600 capric acid monoesters is 98.3% in the extraction liquid, and yield is 94.8%; The relative content of Polyethylene Glycol-600 capric acid dibasic acid esters is 99.6% in the raffinate, and yield is 91.4%.
Embodiment 7
The sad single diester mixture of cetomacrogol 1000 (wherein the quality percentage composition of monoesters, dibasic acid esters is respectively 80.1%, 13.5%) and n-hexyl alcohol are made into the stock liquid of 40 grams per liters, with tributyl ammonium trifluoroacetate ([HNBu
3] [CF
3CO
2])-water mixed solvent ([HNBu
3] [CF
3CO
2] mass percent is 15%) be extraction agent, be washing composition with the n-hexyl alcohol, extraction agent, washing composition, stock liquid three's stream is than being 11:5:1, in the fractionation extraction device, carry out fractionation extraction under 40 ℃, fractionation extraction is divided into extraction section and washing section, and extraction section is two-stage, and washing section is two-stage.Flow out the extraction liquid that is rich in monoesters from the first step of washing section, flow out the raffinate of enrichment dibasic acid esters from the first step of extraction section, collect extraction liquid and raffinate; Extraction liquid and raffinate are removed n-hexyl alcohol through vacuum concentration, and again through washing deionizing liquid repeatedly, dewatering finally by drying obtains monoesters and dibasic acid esters.
Analyze through HPLC, the relative content of the sad monoesters of cetomacrogol 1000 is 99.8% in the extraction liquid, and yield is 97.1%; The relative content of the sad dibasic acid esters of cetomacrogol 1000 is 98.4% in the raffinate, and yield is 94.5%.
Embodiment 8
Poly(oxyethylene glycol) 400 vinylformic acid list diester mixture (wherein the quality percentage composition of monoesters, dibasic acid esters is respectively 20.4%, 70.9%) and 2-hexanol are made into the stock liquid of 5 grams per liters, be extraction agent with 1-butyl-1-methyl piperidine iodine ([BMPi] I)-water mixed solvent (mass percent of [BMPi] I is 80%), be washing composition with the 2-hexanol, extraction agent, washing composition, stock liquid three's stream compares 7.3:1:1, in the fractionation extraction device, carry out fractionation extraction under 60 ℃, fractionation extraction is divided into extraction section and washing section, extraction section is three grades, and washing section is level Four.Flow out the extraction liquid that is rich in monoesters from the first step of washing section, flow out the raffinate of enrichment dibasic acid esters from the first step of extraction section, collect extraction liquid and raffinate; Extraction liquid and raffinate are removed the 2-hexanol through vacuum concentration, and again through washing deionizing liquid repeatedly, dewatering finally by drying obtains monoesters and dibasic acid esters.
Analyze through HPLC, the relative content of poly(oxyethylene glycol) 400 acrylic monoester is 98.6% in the extraction liquid, and yield is 97.8%; The relative content of poly(oxyethylene glycol) 400 diester acrylate is 98.9% in the raffinate, and yield is 97.5%.
Embodiment 9
Cetomacrogol 1000 caproic acid list diester mixture (wherein the quality percentage composition of monoesters, dibasic acid esters is respectively 10.4%, 80.5%) and octyl acetate are made into the stock liquid of 0.8 grams per liter, with 1-dodecyl-3-Methylimidazole bromine salt ([C
12MIm] Br)-water mixed solvent ([C
12MIm] the Br massfraction is 71%) be extraction agent, be washing composition with the octyl acetate, extraction agent, washing composition, stock liquid three's stream is than being 3:2.3:1, in the fractionation extraction device, carry out fractionation extraction under 70 ℃, fractionation extraction is divided into extraction section and washing section, extraction section is level Four, and washing section is seven grades.Flow out the extraction liquid that is rich in monoesters from the first step of washing section, flow out the raffinate of enrichment dibasic acid esters from the first step of extraction section, collect extraction liquid and raffinate; Extraction liquid and raffinate are removed octyl acetate through vacuum concentration, and again through washing deionizing liquid repeatedly, dewatering finally by drying obtains monoesters and dibasic acid esters.
Analyze through HPLC, the relative content of cetomacrogol 1000 caproic acid monoesters is 99.7% in the extraction liquid, and yield is 90.9%; The relative content of cetomacrogol 1000 caproic acid dibasic acid esters is 99.3% in the raffinate, and yield is 95.7%.
Embodiment 10
Polyethylene glycol 6000 timnodonic acid list diester mixture (wherein the quality percentage composition of monoesters, dibasic acid esters is respectively 25.7%, 30.1%) and hexyl acetate are made into the stock liquid of 45 grams per liters, be extraction agent with methanol-water mixed solvent (methanol quality percentage ratio is 40%), be washing composition with the hexyl acetate, extraction agent, washing composition, stock liquid three's stream is than being 8:3.3:1, in the fractionation extraction device, carry out fractionation extraction under 35 ℃, fractionation extraction is divided into extraction section and washing section, extraction section is Pyatyi, and washing section is three grades.Flow out the extraction liquid that is rich in monoesters from the first step of washing section, flow out the raffinate of enrichment dibasic acid esters from the first step of extraction section, collect extraction liquid, raffinate; Extraction liquid, raffinate are removed hexyl acetate, methyl alcohol, water through vacuum concentration, obtain monoesters and dibasic acid esters finally by drying.
Analyze through HPLC, the relative content of polyethylene glycol 6000 eicosa-pentaenoic acid monoester is 98.0% in the extraction liquid, and yield is 99.2%; The relative content of polyethylene glycol 6000 eicosa-pentaenoic acid diester is 98.8% in the raffinate, and yield is 90.3%.
Embodiment 11
Macrogol 2000 0 docosahexenoic acid list diester mixture (wherein the quality percentage composition of monoesters, dibasic acid esters is respectively 60.2%, 15.4%) and Pentyl alcohol are made into the stock liquid of 20 grams per liters, be extraction agent with dimethyl sulfoxide (DMSO)-water mixed solvent (the dimethyl sulfoxide (DMSO) weight fraction is 40%), be washing composition with the Pentyl alcohol, extraction agent, washing composition, stock liquid three's stream is than being 2.9:1:1, in the fractionation extraction device, carry out fractionation extraction under 15 ℃, fractionation extraction is divided into extraction section and washing section, extraction section is level Four, and washing section is level Four.Flow out the extraction liquid that is rich in monoesters from the first step of washing section, flow out the raffinate of enrichment dibasic acid esters from the first step of extraction section, collect extraction liquid and raffinate; Extraction liquid, raffinate are removed Pentyl alcohol, water, dimethyl sulfoxide (DMSO) through vacuum concentration, obtain monoesters and dibasic acid esters finally by drying.
Analyze through HPLC, the relative content of Macrogol 2000 0 docosahexenoic acid monoesters is 98.2% in the extraction liquid, and yield is 95.8%; The relative content of Macrogol 2000 0 docosahexenoic acid dibasic acid esters is 98.6% in the raffinate, and yield is 99.7%.
Embodiment 12
Polyoxyethylene glycol 1200 linolenic acid list diester mixtures (wherein the quality percentage composition of monoesters, dibasic acid esters is respectively 45.8%, 15.9%) and pentyl acetate are made into the stock liquid of 40 grams per liters, be extraction agent with ethanol-water mixed solvent (the ethanol weight fraction is 5%), be washing composition with the pentyl acetate, extraction agent, washing composition, stock liquid three's stream is than being 5:8:1, in the fractionation extraction device, carry out fractionation extraction under 20 ℃, fractionation extraction is divided into extraction section and washing section, extraction section is seven grades, and washing section is level Four.Flow out the extraction liquid that is rich in monoesters from the first step of washing section, flow out the raffinate of enrichment dibasic acid esters from the first step of extraction section, collect extraction liquid, raffinate; Extraction liquid, raffinate are removed pentyl acetate, ethanol, water through vacuum concentration, and drying obtains monoesters and dibasic acid esters.
Analyze through HPLC, the relative content of polyoxyethylene glycol 1200 linolenic acid monoesters is 98.1% in the extraction liquid, and yield is 98.2%; The relative content of polyoxyethylene glycol 1200 linolenic acid dibasic acid esters is 98.3% in the raffinate, and yield is 99.7%.
Embodiment 13
Macrogol 200 oleic acid list diester mixture (wherein the quality percentage composition of monoesters, dibasic acid esters is respectively 20.7%, 50.1%) and heptyl acetate are made into the stock liquid of 70 grams per liters, be extraction agent with n-propyl alcohol-water mixed solvent (the n-propyl alcohol weight fraction is 1%), be washing composition with the heptyl acetate, extraction agent, washing composition, stock liquid three's stream is than being 6:4:1, in the fractionation extraction device, carry out fractionation extraction under 35 ℃, fractionation extraction is divided into extraction section and washing section, extraction section is two-stage, and washing section is three grades.Flow out the extraction liquid that is rich in monoesters from the first step of washing section, flow out the raffinate of enrichment dibasic acid esters from the first step of extraction section, collect extraction liquid, raffinate; Extraction liquid, raffinate are removed heptyl acetate, n-propyl alcohol, water through vacuum concentration, and drying obtains monoesters and dibasic acid esters.
Analyze through HPLC, the relative content of Macrogol 200 oleic acid monoester is 98.3% in the extraction liquid, and yield is 97.2%; The relative content of Macrogol 200 Glycol Oleic Acid Ester is 99.0% in the raffinate, and yield is 98.7%.
Embodiment 14
Polyethylene glycol 6000 palmitinic acid list diester mixture (wherein the quality percentage composition of monoesters, dibasic acid esters is respectively 38.7%, 54.1%) and primary isoamyl alcohol are made into the stock liquid of 40 grams per liters, with tributyl ammonium trifluoroacetate ([HNBu
3] [CF
3CO
2])-water mixed solvent ([HNBu
3] [CF
3CO
2] mass percent is 1%) be extraction agent, be washing composition with the primary isoamyl alcohol, extraction agent, washing composition, stock liquid three's volume flow ratio is 8:5:1, carries out fractionation extraction under 40 ℃ in the fractionation extraction device.Fractionation extraction is divided into extraction section and washing section, and extraction section progression is two-stage, and washing section progression is three grades.Flow out the extraction liquid that is rich in monoesters from the first step of washing section, flow out the raffinate of enrichment dibasic acid esters from the first step of extraction section, collect extraction liquid and raffinate; Extraction liquid and raffinate are removed primary isoamyl alcohol through vacuum concentration, and again through washing deionizing liquid repeatedly, dewatering finally by drying obtains monoesters and dibasic acid esters.
Analyze through HPLC, the relative content of polyethylene glycol 6000 palmitinic acid monoesters is 98.3% in the extraction liquid, and yield is 98.3%; The relative content of polyethylene glycol 6000 palmitinic acid dibasic acid esters is 98.6% in the raffinate, and yield is 98.1%.
Embodiment 15
Macrogol 2000 oleic acid list diester mixture (wherein the quality percentage composition of monoesters, dibasic acid esters is respectively 40.7%, 50.1%) and propyl acetate are made into the stock liquid of 26 grams per liters, with ethyl imidazol(e) a tetrafluoro borate ([EMIm] [BF
4])-water mixed solvent ([EMIm] BF
4Mass percent is 50%) for extraction agent, be washing composition with the propyl acetate, extraction agent, washing composition, stock liquid three's volume flow ratio is 4:3.7:1, carries out fractionation extraction under 40 ℃ in the fractionation extraction device.Fractionation extraction is divided into extraction section and washing section, and extraction section progression is three grades, and washing section progression is three grades.Extraction agent enters the fractionation extraction system from the extraction section first step, stock liquid enters the fractionation extraction system from the last step of extraction section, washing composition enters the fractionation extraction system from the first step of washing section, merge stock liquid at the washing section last step and enter extraction section together, extraction phase carries out counter current contact mutually with washing, flow out the extraction liquid that is rich in monoesters from the first step of washing section, collect extraction liquid; Flow out the raffinate of enrichment dibasic acid esters from the first step of extraction section, collect raffinate; Extraction liquid, raffinate are removed propyl acetate through vacuum concentration, and again through washing deionizing liquid repeatedly, dewatering finally by drying obtains single dibasic acid esters respectively.
Analyze through HPLC, in the extraction liquid in the Macrogol 2000 oleic acid monoester product monoesters relative content be 98.7%, yield is 99.6%; In the raffinate in the Macrogol 2000 Glycol Oleic Acid Ester product dibasic acid esters relative content be 98.7%, yield is 96.7%.
Embodiment 16
Polyethylene Glycol-600 palmitinic acid list diester mixture (wherein the quality percentage composition of monoesters, dibasic acid esters is respectively 78.0%, 21.5%) and 2-enanthol are made into the stock liquid of 27 grams per liters, be extraction agent with n-propyl alcohol-water mixed solvent (the n-propyl alcohol mass percent is 15%), be washing composition with the 2-enanthol, extraction agent, washing composition, stock liquid three's volume flow ratio is 5:3.7:1, carries out fractionation extraction under 40 ℃ in the fractionation extraction device.Fractionation extraction is divided into extraction section and washing section, and extraction section progression is six grades, and washing section progression is seven grades.Extraction agent enters the fractionation extraction system from the extraction section first step, stock liquid enters the fractionation extraction system from the last step of extraction section, washing composition enters the fractionation extraction system from the first step of washing section, merge stock liquid at the washing section last step and enter extraction section together, extraction phase carries out counter current contact mutually with washing, flow out the extraction liquid that is rich in monoesters from the first step of washing section, collect extraction liquid; Flow out the raffinate of enrichment dibasic acid esters from the first step of extraction section, collect raffinate; Extraction liquid, raffinate are removed 2-enanthol etc. through vacuum concentration, and dewatering finally by drying obtains single dibasic acid esters respectively.
Analyze through HPLC, in the extraction liquid in the Polyethylene Glycol-600 palmitinic acid monoesters product monoesters relative content be 99.2%, yield is 99.3%; In the raffinate in the Polyethylene Glycol-600 palmitinic acid dibasic acid esters product dibasic acid esters relative content be 98.9%, yield is 97.7%.
Embodiment 17
The single diester mixtures of polyoxyethylene glycol 800 lauric acid (wherein the quality percentage composition of monoesters, dibasic acid esters is respectively 70.8%, 21.5%) and sec-n-octyl alcohol are made into the stock liquid of 30 grams per liters, be extraction agent with Virahol-water mixed solvent (the Virahol mass percent is 21%), be washing composition with the sec-n-octyl alcohol, extraction agent, washing composition, stock liquid three's volume flow ratio is 3.1:3.7:1, carries out fractionation extraction under 45 ℃ in the fractionation extraction device.Fractionation extraction is divided into extraction section and washing section, and extraction section progression is eight grades, and washing section progression is seven grades.Extraction agent enters the fractionation extraction system from the extraction section first step, stock liquid enters the fractionation extraction system from the last step of extraction section, washing composition enters the fractionation extraction system from the first step of washing section, merge stock liquid at the washing section last step and enter extraction section together, extraction phase carries out counter current contact mutually with washing, flow out the extraction liquid that is rich in monoesters from the first step of washing section, collect extraction liquid; Flow out the raffinate of enrichment dibasic acid esters from the first step of extraction section, collect raffinate; Extraction liquid, raffinate are removed sec-n-octyl alcohol etc. through vacuum concentration, and dewatering finally by drying obtains single dibasic acid esters respectively.
Analyze through HPLC, in the extraction liquid in the polyoxyethylene glycol 800 lauric acid monoesters products monoesters relative content be 99.1%, yield is 99.4%; In the raffinate in the polyoxyethylene glycol 800 lauric acid dibasic acid esters products dibasic acid esters relative content be 99.0%, yield is 97.8%.
Embodiment 18
Poly(oxyethylene glycol) 400 vinylformic acid list diester mixture (wherein the quality percentage composition of monoesters, dibasic acid esters is respectively 68.0%, 31.5%) and isopropyl acetate are made into the stock liquid of 20 grams per liters, with N, dinethylformamide-water mixed solvent (N, the dinethylformamide mass percent is 10%) be extraction agent, be washing composition with the isopropyl acetate, extraction agent, washing composition, stock liquid three's volume flow ratio is 3.5:3.9:1, carries out fractionation extraction under 30 ℃ in the fractionation extraction device.Fractionation extraction is divided into extraction section and washing section, and extraction section progression is level Four, and washing section progression is Pyatyi.Extraction agent enters the fractionation extraction system from the extraction section first step, stock liquid enters the fractionation extraction system from the last step of extraction section, washing composition enters the fractionation extraction system from the first step of washing section, merge stock liquid at the washing section last step and enter extraction section together, extraction phase carries out counter current contact mutually with washing, flow out the extraction liquid that is rich in monoesters from the first step of washing section, collect extraction liquid; Flow out the raffinate of enrichment dibasic acid esters from the first step of extraction section, collect raffinate; Extraction liquid, raffinate are removed isopropyl acetate etc. through vacuum concentration, and dewatering finally by drying obtains the single dibasic acid esters of TPGS respectively.
Analyze through HPLC, in the extraction liquid in the poly(oxyethylene glycol) 400 acrylic monoester product monoesters relative content be 98.5%, yield is 98.5%; In the raffinate in the poly(oxyethylene glycol) 400 diester acrylate product dibasic acid esters relative content be 99.1%, yield is 98.6%.
Embodiment 19
Macrogol 2000 linolic acid list diester mixture (wherein the quality percentage composition of monoesters, dibasic acid esters is respectively 73.0%, 24.5%) and isooctyl alcohol are made into the stock liquid of 35 grams per liters, be extraction agent with acetonitrile-water mixed solvent (the acetonitrile mass percent is 70%), be washing composition with the isooctyl alcohol, extraction agent, washing composition, stock liquid three's volume flow ratio is 5:3.7:1, carries out fractionation extraction under 40 ℃ in the fractionation extraction device.Fractionation extraction is divided into extraction section and washing section, and extraction section progression is Pyatyi, and washing section progression is Pyatyi.Extraction agent enters the fractionation extraction system from the extraction section first step, stock liquid enters the fractionation extraction system from the last step of extraction section, washing composition enters the fractionation extraction system from the first step of washing section, merge stock liquid at the washing section last step and enter extraction section together, extraction phase carries out counter current contact mutually with washing, flow out the extraction liquid that is rich in monoesters from the first step of washing section, collect extraction liquid; Flow out the raffinate of enrichment dibasic acid esters from the first step of extraction section, collect raffinate; Extraction liquid, raffinate are removed isooctyl alcohol etc. through vacuum concentration, and dewatering finally by drying obtains single dibasic acid esters respectively.
Analyze through HPLC, in the extraction liquid in the Macrogol 2000 linolic acid monoesters product monoesters relative content be 98.9%, yield is 98.8%; In the raffinate in the Macrogol 2000 linolic acid dibasic acid esters product dibasic acid esters relative content be 98.7%, yield is 98.1%.
Claims (9)
1. the method for an extracting and separating polyethylene glycol fatty acid list dibasic acid esters is characterized in that, may further comprise the steps:
(1) be raw material with polyethylene glycol fatty acid list diester mixture, ester class or alcohols hydrophobic organic solvent with solubleness≤15g/100g in the water are made into stock liquid, the binary mixed solvent of forming with water, hydrophilic ionic-liquid, hydrophilic ionic-liquid and water or water-soluble fully polar organic solvent are extraction agent with the binary mixed solvent of water composition, used hydrophobic organic solvent is washing composition during with preparation raw material liquid, carries out fractionation extraction;
(2) the fractionation extraction device is divided into extraction section and washing section, extraction agent enters the fractionation extraction system from the extraction section first step, stock liquid enters the fractionation extraction system from the last step of extraction section, washing composition enters the fractionation extraction system from the first step of washing section, merge stock liquid at the washing section last step and enter extraction section together, extraction phase carries out counter current contact mutually with washing, flow out the extraction liquid that is rich in the polyethylene glycol fatty acid monoesters from the first step of washing section, flow out the raffinate of enrichment polyethylene glycol fatty acid dibasic acid esters from the first step of extraction section, collect extraction liquid and raffinate respectively;
(3) with extraction liquid through vacuum concentration, washing and drying, obtain polyethylene glycol fatty acid monoesters product, raffinate obtains polyethylene glycol fatty acid dibasic acid esters product through vacuum concentration, washing and drying;
The ester class of solubleness≤15g/100g or alcohols hydrophobic organic solvent are methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butylacetate, pentyl acetate, hexyl acetate, heptyl acetate, octyl acetate, propyl carbinol, Pentyl alcohol, n-hexyl alcohol, n-Heptyl alcohol, n-Octanol, primary isoamyl alcohol, isooctyl alcohol, 2-hexanol, 2-enanthol or sec-n-octyl alcohol in the described water;
Described hydrophilic ionic-liquid is by positively charged ion M
+And anion N
-Two portions are formed; Positively charged ion M
+For having substituent imidazole type positively charged ion, have substituent pyridine type positively charged ion, have substituent quaternary phosphine type positively charged ion, have substituent piperidines type positively charged ion, have substituent quaternary ammonium cation or having a kind of in the substituent tetramethyleneimine type positively charged ion; Anion N
-A kind of in chlorion, bromide anion, iodide ion, tetrafluoroborate, trifluoroacetic acid root, trifluoromethanesulfonic acid root, ethylsulfonic acid root, dimethyl phosphate radical, diethyl phosphate radical, dihydrogen phosphate or the amino acid group; Described substituting group is C
1～C
16Alkyl, in the hydroxyethyl one or both;
Described water-soluble polar organic solvent fully is methyl alcohol, ethanol, n-propyl alcohol, Virahol, dimethyl sulfoxide (DMSO), N, dinethylformamide or acetonitrile.
2. the method for extracting and separating polyethylene glycol fatty acid list dibasic acid esters as claimed in claim 1 is characterized in that, described polyoxyethylene glycol molecular-weight average is between 200～20000.
3. the method for extracting and separating polyethylene glycol fatty acid list dibasic acid esters as claimed in claim 1, it is characterized in that, described lipid acid is saturated fatty acid, monounsaturated fatty acids or polyunsaturated fatty acid, and described saturated fatty acid is sad, capric acid, lauric acid, palmitinic acid or stearic acid; Described monounsaturated fatty acids is Semen Myristicae oleic acid, Zoomeric acid or oleic acid; Described polyunsaturated fatty acid is timnodonic acid or docosahexenoic acid.
4. the method for extracting and separating polyethylene glycol fatty acid list dibasic acid esters as claimed in claim 1 is characterized in that, the total concn of single dibasic acid esters is 0.5 grams per liter～200 grams per liters in the described stock liquid.
5. the method for extracting and separating polyethylene glycol fatty acid list dibasic acid esters as claimed in claim 1 is characterized in that, the mass percent of the binary mixed extractant intermediate ion liquid that described hydrophilic ionic-liquid and water are formed is 1%～99%.
6. the method for extracting and separating polyethylene glycol fatty acid list dibasic acid esters as claimed in claim 1 is characterized in that, described fully water-soluble polar organic solvent is 1%～70% with the mass percent of the binary mixed extractant Semi-polarity organic solvent of water composition.
7. the method for extracting and separating polyethylene glycol fatty acid list dibasic acid esters as claimed in claim 1 is characterized in that, the volume flow ratio between described extraction agent, washing composition, the stock liquid three is 2～15:1～5:1.
8. the method for extracting and separating polyethylene glycol fatty acid list dibasic acid esters as claimed in claim 1 is characterized in that, the service temperature of described fractionation extraction is 10 ℃～70 ℃.
9. the method for extracting and separating polyethylene glycol fatty acid list dibasic acid esters as claimed in claim 1 is characterized in that, the extraction section of described fractionation extraction is two to eight grades, and washing section is two to eight grades.
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| CN116102529A (en) * | 2022-12-13 | 2023-05-12 | 浙江省林业科学研究院 | Method for separating methyl ophiopogon root flavanone A and methyl ophiopogon root flavanone B |
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