CN108069858B - Method for extracting and separating methyl linolenate by coupling fatty acid soap and silver nitrate - Google Patents
Method for extracting and separating methyl linolenate by coupling fatty acid soap and silver nitrate Download PDFInfo
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- CN108069858B CN108069858B CN201711104923.1A CN201711104923A CN108069858B CN 108069858 B CN108069858 B CN 108069858B CN 201711104923 A CN201711104923 A CN 201711104923A CN 108069858 B CN108069858 B CN 108069858B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0492—Applications, solvents used
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
Abstract
The invention provides a method for extracting and separating methyl linolenate by coupling fatty acid soap and silver nitrate, which is characterized in that high-purity methyl linolenate products are obtained by carrying out methyl esterification, extraction, back extraction and solvent removal under reduced pressure on vegetable oil rich in linolenic acid. The innovation of the invention is that the extractant used in the extraction process is a mixed solution of silver nitrate, fatty acid soap and water, which is different from the extractant of silver nitrate, methanol and water used in the existing silver ion complexing extraction. The fatty acid soap is used for replacing methanol, and has the advantages that: 1) the solubility of the methyl linolenate in an extraction phase is increased, and the yield of the methyl linolenate is improved; 2) the extraction selectivity of the methyl linolenate is increased, and the purity of the methyl linolenate in the product is improved; 3) the residual quantity of silver ions in the product is reduced; 4) reduces the loss of silver ions of the extraction phase and is beneficial to the recycling of the extractant.
Description
Technical Field
The invention relates to the technical field of oil separation and purification, in particular to an extraction method for extracting and separating polyunsaturated fatty acid from vegetable oil, and specifically relates to a method for extracting and separating methyl linolenate by coupling fatty acid soap and silver nitrate.
Background
Linolenic acid has important physiological function for human body, and can be used in medicine, cosmetic and health product industries. The physiological activity of the linolenic acid is closely related to the purity of the linolenic acid, and the extraction and purification of the linolenic acid from the vegetable oil and fat have important significance. The fatty acid composition in the vegetable oil is complex, the molecular structures of the fatty acid are similar, and the separation of linolenic acid is difficult. The existing extraction and separation methods mainly comprise a urea inclusion method, a molecular distillation method, a supercritical extraction method, a freezing crystallization method, a lipase concentration method, a membrane separation method, a silver ion complexation method and the like. These methods have been used to some extent in the separation of polyunsaturated fatty acids, but have had their own problems. The silver ion complexation method has high selectivity, but silver nitrate is easily soluble in water, methanol and other organic solvents, when linolenic acid (ester) is extracted and separated by using a silver nitrate aqueous solution, linolenic acid (ester) with low polarity is hardly soluble in a silver nitrate aqueous solution with high polarity, the extraction rate is extremely low, and methanol must be added into the silver nitrate aqueous solution to adjust the polarity of the linolenic acid (ester) so as to increase the solubility of methyl linolenate in an extraction phase. The addition of methanol has four adverse effects on the separation: 1) the solubility of silver nitrate in an extraction phase is reduced; 2) the solubility of linolenic acid (ester) in the extract phase is increased, and the solubility of other fatty acid (ester) in the extract phase is also increased, so that the separation selectivity and the purity of the linolenic acid (ester) in the product are reduced; 3) the intersolubility of the extract phase and the raw material phase (oil phase) is increased, so that the residual quantity of silver nitrate in the oil phase is increased, and the loss of the silver nitrate is caused; 4) the density of the extraction phase and the raw material phase is reduced, and the time for the two phases to separate in a layered mode is prolonged. Aiming at the problems in the implementation process of the existing silver ion complexing method, the invention provides a method for extracting fatty acid soap and silver nitrate in a coupling manner, wherein the fatty acid soap is used for replacing methanol, so that the problems caused by the methanol are solved.
Disclosure of Invention
Aiming at the defects of the prior technical scheme for separating unsaturated fatty acid (ester) by silver ion complexing extraction, the invention aims to provide a method for separating methyl linolenate by coupling extraction of fatty acid soap and silver nitrate, which adopts a novel method for separating polyunsaturated fatty acid (ester) by coupling extraction of fatty acid soap and silver nitrate, can improve the yield and purity of methyl linolenate, reduce silver nitrate residue in an oil phase, simultaneously reduce silver nitrate loss and facilitate the recycling of an extract phase.
The method for extracting and separating the methyl linolenate by coupling the fatty acid soap and the silver nitrate is characterized by comprising the following steps of:
1) converting vegetable oil rich in linolenic acid and methanol into mixed fatty acid methyl ester through methyl esterification reaction;
2) preparing fatty acid soap by saponifying fatty acid;
3) extraction separation of methyl linolenate by coupling fatty acid soap and silver nitrate
3.1) weighing silver nitrate, dissolving the silver nitrate with water, and preparing a silver nitrate water solution;
3.2) adding the fatty acid soap obtained in the step 2) into a silver nitrate aqueous solution, and intensively stirring and uniformly mixing under the condition of keeping out of the sun to form a silver nitrate-fatty acid soap-water mixture serving as an extracting agent;
3.3) mixing the silver nitrate-fatty acid soap-water mixed solution in the step 3.1) with the mixed fatty acid methyl ester in the step 1), and stirring and extracting under the condition of keeping out of the sun;
3.4) standing and layering after stirring, taking a lower-layer extract phase, and back-extracting for 2-4 times by using petroleum ether with the same volume;
3.5) standing and layering after the back extraction is finished, taking the upper petroleum ether phase, combining the petroleum ether phases obtained by the back extraction, and removing the petroleum ether by reduced pressure evaporation to obtain an oily substance, namely a methyl linolenate product.
The method for extracting and separating the methyl linolenate by coupling the fatty acid soap and the silver nitrate is characterized in that the vegetable oil rich in the linolenic acid in the step 1) is linseed oil or Chinese tallow kernel oil, only two kinds of oil are selected as examples in the invention, and other vegetable oil rich in the linolenic acid can be separated by the method defined by the invention.
The method for extracting and separating the methyl linolenate by coupling the fatty acid soap and the silver nitrate is characterized in that the fatty acid in the step 2) is a saturated fatty acid, preferably lauric acid, myristic acid, palmitic acid or stearic acid.
The method for separating the methyl linolenate by coupling extraction of the fatty acid soap and the silver nitrate is characterized in that the concentration of the silver nitrate in the step 3.1) is 0.1-10 mol/L.
The method for extracting and separating the methyl linolenate by coupling the fatty acid soap and the silver nitrate is characterized in that the stirring speed of the intensive stirring in the step 3.2) is 300-500 rpm.
The method for extracting and separating the methyl linolenate by coupling the fatty acid soap and the silver nitrate is characterized in that the back-extraction temperature in the step 3.4) is 55-65 ℃, preferably 60 ℃, and the back-extraction stirring time is 25-35min, preferably 30min.
The method for extracting and separating the methyl linolenate by coupling the fatty acid soap and the silver nitrate is characterized in that the mass of the fatty acid soap is 0.1-10% of that of the vegetable oil.
The method for extracting and separating methyl linolenate by coupling fatty acid soap and silver nitrate is characterized in that the ratio of a silver nitrate-fatty acid soap-water mixture extracting agent to mixed fatty acid methyl ester is 0.1-10: 1, and the extraction temperature is-10-35 ℃.
The method for extracting and separating methyl linolenate by coupling fatty acid soap and silver nitrate is characterized in that the ratio of a silver nitrate-fatty acid soap-water mixture extracting agent to mixed fatty acid methyl ester is 1:1, and the extraction temperature is 25 ℃.
By adopting the technology, compared with the prior art, the method has the advantages that the yield and purity of the methyl linolenate can be improved, the silver nitrate residue in the oil phase can be reduced, the silver nitrate loss is reduced, and the separation of the polyunsaturated fatty acid (ester) which is recycled by the extraction phase is facilitated by adopting the fatty acid soap and the silver nitrate coupling extraction.
Detailed Description
The invention is further illustrated by the following examples:
example 1 (silver nitrate (1 mol/L) -palmitic acid soap (1 wt%) -water extraction)
1) Preparation of Chinese tallow kernel oil methyl ester
The Chinese tallow kernel oil methyl esterification adopts a known method: weighing 20g of methanol and 1g of KOH, mixing and dissolving, adding into 100g of Chinese tallow kernel oil, stirring and refluxing at 60 ℃ for 1 hour, standing for layering, taking an upper oil layer, washing with water to be neutral, and removing water in vacuum to obtain the Chinese tallow kernel oil methyl ester (mixed fatty acid methyl ester).
2) Preparation of palmitic acid soap
The method for preparing the palmitic acid soap by saponifying the palmitic acid adopts the known method: 5g KOH was weighed and dissolved in 100ml water to prepare 5% KOH aqueous solution. Weighing 20g of palmitic acid, adding 100ml of 5% KOH aqueous solution, stirring at normal temperature for 30min, filtering, washing the solid with water to be neutral, and drying to remove water to obtain the white palmitic acid soap.
3) Extraction of methyl linolenate by coupling palmitic acid soap and silver nitrate
Preparing 1mol/L silver nitrate aqueous solution;
adding 1g of palmitic acid soap into 10mL of 1mol/L silver nitrate aqueous solution, and strongly stirring in a dark place to uniformly disperse the palmitic acid soap in the silver nitrate aqueous solution;
③ weighing 10g Chinese tallow kernel oil methyl ester, adding 10mL of the silver nitrate-palmitic acid soap-water solution, stirring at normal temperature in dark for 30min, and extracting and separating; after extraction, standing for layering, taking the lower extraction phase, adding 10mL of petroleum ether, stirring at 60 ℃ in a dark place for 30min, and carrying out back extraction; after the back extraction, the stirring is stopped, the mixture is kept stand for 60min, and the back extraction process is repeated for 2 times by using 10mL of petroleum ether for the lower silver nitrate-palmitic acid soap-water solution phase. And (3) combining the petroleum ether phases obtained by the back extraction for 3 times, and removing the petroleum ether by reduced pressure evaporation to obtain a product, wherein the mass of the product is 1.080g, and the product is analyzed by gas chromatography, and the content of the methyl linolenate in the product is 89.68%. The yield of methyl linolenate was 23.2% by calculation of the formula (1).
In the formula (1), mF、mpRespectively the quality of the raw material and the product, xF、xpThe contents of the raw material and the product are respectively the methyl linolenate content.
Fourthly, the residual quantity of Ag ions in the products of the extract phase and the raffinate phase is measured according to the known method (the Morel method): respectively distilling the extract phase and the raffinate phase under reduced pressure to remove the solvent to obtain an oily product; dissolving 0.5001g product in 10mL ethanol, adding 10mL water, dissolving with vortex oscillator to obtain sample, adding into brown burette, and recording total volume (V)0mL); taking 2mL of 0.01mol/L standard NaCl aqueous solution, placing the solution in a conical flask, adding 34 drops of 5% K2CrO4And (3) taking the aqueous solution as an indicator, titrating the sample to be detected until brick red precipitates are generated, and recording the volume of the sample to be detected consumed. The residual Ag ion amount was calculated by the formula (2), and the residual Ag ion amount was not detected in both the raffinate phase and the extract phase by the known Mohr method.
In the formula (2), 107.87-Ag ion molar mass, CNaClConcentration of NaCl Standard solution 0.01mol/L, VNaClVolume mL, V of NaCl Standard solutionsConsumed sample volume mL, m0Sample masses g, V0Sample volume mL.
Example 2 (silver nitrate (1 mol/L) -palmitic acid soap (0.5 wt%) -water extraction)
1) Chinese tallow kernel oil methyl ester and palmitic acid soap were prepared separately according to known methods, see example 1.
2) Extraction of methyl linolenate by coupling palmitic acid soap and silver nitrate
Taking 10mL of 1mol/L silver nitrate aqueous solution, adding 0.5g of palmitic acid soap into the 1mol/L silver nitrate aqueous solution, and intensively stirring the mixture in a dark place to uniformly disperse the palmitic acid soap in the silver nitrate aqueous solution;
② weighing 10g Chinese tallow kernel oil methyl ester, adding 10mL above silver nitrate-palmitic acid soap-water solution, stirring at normal temperature in dark place for 1h, extracting and separating; after extraction, standing for layering, taking the lower extraction phase, adding 10mL of petroleum ether, stirring at 60 ℃ in a dark place for 30min, and carrying out back extraction; after the back extraction, the stirring is stopped, the mixture is kept stand for 60min, and the back extraction process is repeated for 2 times by using 10mL of petroleum ether for the lower silver nitrate-palmitic acid soap-water solution phase. And (3) combining the petroleum ether phases obtained by the back extraction for 3 times, and removing the petroleum ether by reduced pressure evaporation to obtain a product, wherein the mass of the product is 0.601g, and the composition is analyzed by gas chromatography, and the content of the methyl linoleate in the product is 93.2%. The yield of methyl linolenate was 13.4% by calculation of the formula (1).
③ the residual amount of Ag ions in the extract and raffinate products was determined by a known method (Morel method), see example 1. According to the known Mohr method, the residual silver ion amount is not detected in both the raffinate phase and the extract phase.
Example 3 (silver nitrate (1 mol/L) -stearic acid soap (1.0 wt%) -Water extraction)
1) Preparation of Chinese tallow kernel oil methyl ester
Methyl esterification of Chinese tallow kernel oil is carried out by a known method, as shown in example 1.
2) Preparation of stearic acid soap
The method for preparing the stearic acid soap by saponifying stearic acid adopts the known method: 5g KOH was weighed and dissolved in 100ml water to prepare 5% KOH aqueous solution. Weighing 20g of stearic acid, adding 100ml of 5% KOH aqueous solution, stirring at normal temperature for 30min, carrying out suction filtration, washing the solid to be neutral by water, and drying to remove water to obtain the white stearic acid soap.
3) Extraction of methyl linolenate by coupling stearic acid soap and silver nitrate
Preparing 1mol/L silver nitrate aqueous solution;
secondly, 10mL of 1mol/L silver nitrate aqueous solution is taken, 1g of stearic acid soap is added into the silver nitrate aqueous solution, and the mixture is strongly stirred in a dark place, so that the stearic acid soap is uniformly dispersed in the silver nitrate aqueous solution;
③ weighing 10g Chinese tallow kernel oil methyl ester, adding 10mL of the silver nitrate-stearic acid soap-water solution, stirring at normal temperature in dark for 1h, and extracting and separating; after extraction, standing for layering, taking the lower extraction phase, adding 10mL of petroleum ether, stirring at 65 ℃ in a dark place for 30min, and carrying out back extraction; after the back extraction, the stirring is stopped, the mixture is kept stand for 60min, and the back extraction process is repeated for 2 times by using 10mL of petroleum ether as a lower silver nitrate-stearic acid soap-water solution phase. And (3) combining the petroleum ether phases obtained by the back extraction for 3 times, and removing the petroleum ether by reduced pressure evaporation to obtain a product, wherein the mass of the product is 1.04g, and the product is analyzed by gas chromatography, and the content of the methyl linoleate in the product is 90.59%. The yield of methyl linolenate was 22.5% by calculation of the formula (1).
The residual amount of Ag ions in the extract and raffinate products was determined by known methods (Moire method), see example 1. According to the known Mohr method, the residual silver ion amount is not detected in both the raffinate phase and the extract phase.
Example 4 (silver nitrate (1 mol/L) -palmitic acid soap (1.0 wt%) -water extraction recycle)
Weighing 10g Chinese tallow kernel oil methyl ester, adding 10ml extracting agent (silver nitrate-palmitic acid soap-water solution) used in example 1, stirring at room temperature in dark place for 30min, and extracting and separating; after extraction, standing for layering, taking the lower extraction phase, adding 10mL of petroleum ether, stirring at 60 ℃ in a dark place for 30min, and carrying out back extraction; after the back extraction, the stirring is stopped, the mixture is kept stand for 60min, and the back extraction process is repeated for 2 times by using 10mL of petroleum ether for the lower silver nitrate-palmitic acid soap-water solution phase. And (3) combining the petroleum ether phases obtained by the back extraction for 3 times, and removing the petroleum ether by reduced pressure evaporation to obtain a product, wherein the mass of the product is 1.071g, and the product is analyzed by gas chromatography, and the content of the methyl linolenate in the product is 90.15%. The yield of methyl linolenate was 23.1% by calculation of the formula (1). The residual amounts of Ag ions in the extract and raffinate products were determined in a manner known per se (Mohr's method), see example 1. According to the known Mohr method, the residual silver ion amount is not detected in both the raffinate phase and the extract phase.
Comparative example 1: (silver nitrate-methanol-water extraction)
60mL of methanol and 40mL of water are respectively taken by using a measuring cylinder, and mixed to prepare a methanol aqueous solution with the methanol concentration of 60%.
17.01g of silver nitrate is weighed, dissolved by methanol aqueous solution (the concentration of methanol is 60 percent) and the volume is determined to be 100mL, so as to prepare 1.0mol/L silver nitrate-methanol-aqueous solution.
Weighing 20g of methyl tallowseed oil methyl ester after methyl esterification by a known method, adding 20mL of 1.0mol/L silver nitrate-methanol-water solution (methanol content is 60%), stirring at 10 deg.C in dark for 30min, extracting and separating, and stirring at 200 rpm. After extraction, stirring was stopped and the mixture was allowed to stand for 60 min. The lower extract phase (silver nitrate-methanol-water solution phase) was taken, 20mL of petroleum ether was added, and back extraction was performed by stirring at 50 ℃ for 30min in the dark. After the back extraction is finished, the stirring is stopped, the mixture is kept stand for 60min, and the back extraction process is repeated for 2 times by using 20mL of petroleum ether at the lower layer. And (3) combining petroleum ether phases obtained by the back extraction for 3 times, and removing the petroleum ether by reduced pressure evaporation to obtain a product, wherein the mass of the product is 1.5770g, and the composition of the product is analyzed by gas chromatography, and the content of the methyl linoleate in the product is 72.61%. The yield of methyl linolenate was 13.7% by calculation of the formula (1).
The solvent is removed from the raffinate phase and the extract phase obtained by extracting and separating the Chinese tallow kernel oil by vacuum distillation respectively, and the residual quantity of Ag ions in the extract phase and the raffinate phase products is determined by a known method (Mohr method), see example 1.
Comparative example 2: (silver nitrate-methanol-water recycle)
20g of Chinese tallow kernel oil methyl ester is weighed, 20ml of the extracting agent (silver nitrate-methanol-water solution) used once in the comparison example 1 is added, and the mixture is stirred for 30min in the dark at the temperature of 10 ℃ for extraction and separation, and the stirring speed is 200 rpm. After extraction, stirring was stopped and the mixture was allowed to stand for 60 min. The lower extract phase (silver nitrate-methanol-water solution phase) was taken, 20mL of petroleum ether was added, and back extraction was performed by stirring at 50 ℃ for 30min in the dark. After the back extraction is finished, the stirring is stopped, the mixture is kept stand for 60min, and the back extraction process is repeated for 2 times by using 20mL of petroleum ether at the lower layer. And (3) combining petroleum ether phases obtained by the back extraction for 3 times, and removing the petroleum ether by reduced pressure evaporation to obtain a product, wherein the weight of the product is 1.325g, and the composition of the product is analyzed by gas chromatography, and the content of the methyl linoleate in the product is 69.02%. The yield of methyl linolenate was 10.9% by calculation of the formula (1). The residual silver ion content in the raffinate phase and extract phase products was 5.38 and 2.21mg/g, respectively, as determined by the Morel method.
Claims (11)
1. A method for extracting and separating methyl linolenate by coupling fatty acid soap and silver nitrate is characterized by comprising the following steps:
1) converting vegetable oil rich in linolenic acid and methanol into mixed fatty acid methyl ester through methyl esterification reaction;
2) preparing fatty acid soap by saponifying fatty acid;
3) extraction separation of methyl linolenate by coupling fatty acid soap and silver nitrate
3.1) weighing silver nitrate, dissolving the silver nitrate with water, and preparing a silver nitrate water solution;
3.2) adding the fatty acid soap obtained in the step 2) into a silver nitrate aqueous solution, and intensively stirring and uniformly mixing under the condition of keeping out of the sun to form a silver nitrate-fatty acid soap-water mixture serving as an extracting agent;
3.3) mixing the silver nitrate-fatty acid soap-water mixed solution in the step 3.1) with the mixed fatty acid methyl ester in the step 1), and stirring and extracting under the condition of keeping out of the sun;
3.4) standing and layering after stirring, taking a lower-layer extract phase, and back-extracting for 2-4 times by using petroleum ether with the same volume;
3.5) standing and layering after the back extraction is finished, taking the upper petroleum ether phase, combining the petroleum ether phases obtained by the back extraction, and removing the petroleum ether by reduced pressure evaporation to obtain an oily substance, namely a methyl linolenate product.
2. The method for extracting and separating methyl linolenate by coupling fatty acid soap and silver nitrate according to claim 1, wherein the linolenic acid-rich vegetable oil in step 1) is linseed oil or Chinese tallow kernel oil.
3. The method for separating methyl linolenate by coupling extraction of fatty acid soap and silver nitrate according to claim 1, wherein the fatty acid in step 2) is a saturated fatty acid.
4. The method for separating the methyl linolenate by coupling extraction of the fatty acid soap and the silver nitrate according to claim 1, wherein the concentration of the silver nitrate in the step 3.1) is 0.1-10 mol/L.
5. The method for extracting and separating methyl linolenate from fatty acid soap and silver nitrate in a coupling manner as claimed in claim 1, wherein the stirring speed of the intensive stirring in step 3.2) is 300-500 rpm.
6. The method for extracting and separating the methyl linolenate by coupling the fatty acid soap with the silver nitrate according to claim 1, wherein the back-extraction temperature in the step 3.4) is 55-65 ℃, and the back-extraction stirring time is 25-35 min.
7. The method for extracting and separating methyl linolenate by coupling fatty acid soap and silver nitrate according to claim 1, wherein the mass of the fatty acid soap is 0.1-10% of the mass of the vegetable oil.
8. The method for extracting and separating methyl linolenate by coupling fatty acid soap and silver nitrate according to claim 1, wherein the ratio of the silver nitrate-fatty acid soap-water mixture extracting agent to the mixed fatty acid methyl ester is 0.1-10: 1, and the extraction temperature is-10-35 ℃.
9. The method for extracting and separating methyl linolenate by coupling fatty acid soap and silver nitrate according to claim 1, wherein the ratio of the silver nitrate-fatty acid soap-water mixture extracting agent to the mixed fatty acid methyl ester is 1:1, and the extraction temperature is 25 ℃.
10. The method for extracting and separating methyl linolenate by coupling fatty acid soap with silver nitrate according to claim 3, wherein the fatty acid in step 2) is lauric acid, myristic acid, palmitic acid or stearic acid.
11. The method for extracting and separating the methyl linolenate by coupling the fatty acid soap with the silver nitrate according to claim 6, wherein the back-extraction temperature in the step 3.4) is 60 ℃, and the back-extraction stirring time is 30min.
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| Improvement of saponification extraction method for fatty acids separation from geological samples;Jiang Chang et al.;《Acta Geochim》;20160323;第35卷(第2期);148-155 * |
| 多不饱和脂肪酸甲酯的分离;黄晨蕾;《万方数据库》;20160330;15-27 * |
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