CN112094184B - Method for extracting shikimic acid from ginkgo leaf extract chromatographic wastewater - Google Patents
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- C07C51/42—Separation; Purification; Stabilisation; Use of additives
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
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- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Abstract
The invention discloses a method for extracting shikimic acid from ginkgo leaf extract chromatographic wastewater, which takes chromatographic wastewater generated in the production process of ginkgo leaf extract as a raw material, concentrates the wastewater into thick paste, adds a mixed solvent, stirs and extracts, and stands to separate insoluble substances to obtain a mixed solvent layer; after the solvent is recovered from the mixed solvent layer, adding a small amount of water for dissolving; extracting the obtained water solution to remove impurities, separating water layer, recovering solvent, and concentrating to obtain shikimic acid crystal; finally stirring and pulping shikimic acid crystal, filtering and drying to obtain shikimic acid, wherein the content of shikimic acid is more than 98 percent. The invention utilizes the special properties of the mixed solvent to change the distribution ratio of shikimic acid and impurities in two phases of a liquid-liquid extraction system, thereby achieving the selective enrichment of shikimic acid; acid and alkali are not used in the production process, the solvent can be recycled, the operation is simple, the method is suitable for industrial production, and the product purity is high.
Description
Technical Field
The invention relates to a method for extracting shikimic acid from ginkgo leaf extract chromatographic wastewater, belonging to the field of extraction and purification of plant active ingredients.
Background
At present, shikimic acid mainly comes from three ways of chemical synthesis, microbial fermentation and plant extraction. Wherein, the plant extraction method is the main way for producing shikimic acid, and the main raw material is derived from the star anise and has single resource. Studies show that folium Ginkgo contains around 4% shikimic acid, which is close to the content of shikimic acid in fructus Anisi Stellati. A method for extracting shikimic acid from folium Ginkgo has been reported, and mainly adopts activated carbon, silica gel, modified vermiculite adsorbent, anion exchange resin adsorption and the like for extraction. Experiments show that the shikimic acid adsorption amount is small due to the fact that organic acids in ginkgo leaves are more in types (including shikimic acid, protocatechuic acid, 6-hydroxykynurenic acid, p-hydroxybenzoic acid, gallic acid and the like), and the selective adsorption of the activated carbon and silica gel adsorbent to the shikimic acid is poor; because of the influence of competitive adsorption substances, the adsorption quantity of shikimic acid in the waste water in the ion exchange resin is reduced, the acid-base dosage is large during elution, the treatment volume of the feed liquid is large, and the production cost is high, so that the industrial production is difficult to realize.
Therefore, the invention provides a method for extracting shikimic acid from ginkgo biloba extract chromatographic wastewater based on the economic consideration of industrial production. The method has good selectivity and extraction rate of shikimic acid, simple operation, low equipment investment and high product purity, and is suitable for industrial production. Acid and alkali are not used in the production process, and the used solvent is recycled repeatedly, so that the environmental influence is small. The method has great significance for the deep development of the ginkgo leaf resource and is expected to have good economic benefit.
Disclosure of Invention
Aiming at the defect that industrial production is difficult to realize by extracting shikimic acid from ginkgo leaf extract chromatographic wastewater at present, the invention aims to provide a method which is simple to operate and is suitable for industrial production. If the ginkgo biloba extract chromatographic wastewater is directly concentrated to be dry, the dry matter content of shikimic acid is only 10-30%, and the direct crystallization has the defects of slow crystallization, difficult filtration, low purity, low yield and the like. Considering that shikimic acid is easy to dissolve in water, and has certain solubility in solvent A such as ethanol, isopropanol and acetone; but the solubility in solvents B such as ethyl acetate, methyl acetate, dichloromethane and diethyl ether is very low; likewise, other water-soluble impurities in the wastewater, such as sugars, tannins, proteins, etc., are less soluble than shikimic acid in solvent a, solvent B. Therefore, theoretically, a mixed solvent combination exists, so that the mixed solvent combination has certain solubility to shikimic acid, and therefore, the mixed solvent combination has certain extraction efficiency, and simultaneously, the impurity content in dry matters of the extract of the mixed solvent can be reduced. In an extraction system consisting of water and a mixed solvent, dry matters of two extraction phases are respectively analyzed, and the fact that although the distribution ratio of shikimic acid in the water phase is higher than that of shikimic acid in the mixed solvent phase is found, the content of shikimic acid in a coherent substance of the mixed solvent is far higher than that of shikimic acid in the dry matters of the water phase, the content of the shikimic acid in the mixed solvent phase can exceed 60 percent, and the dry matter content reaches 60 percent is a necessary condition for ensuring that the next crystallization is carried out efficiently.
The invention adopts mixed solvent extraction, utilizes the complementary advantages of the mixed solvent to increase the distribution ratio difference of shikimic acid and impurities in two phases of a liquid-liquid extraction system, further realizes the selective enrichment of shikimic acid, ensures that the shikimic acid content in the enriched feed liquid dry matter reaches or exceeds the minimum content requirement of smoothly crystallizing the shikimic acid, and then refines the shikimic acid by a crystallization method, and the obtained product has high purity.
In order to achieve the technical effects, the invention adopts the following technical scheme: a method for extracting shikimic acid from ginkgo leaf extract chromatography wastewater comprises the following steps:
step 1, taking macroporous adsorption resin chromatography wastewater under the item of extracting ginkgo leaf extract according to Chinese pharmacopoeia, and concentrating the wastewater until the water content is 15-25% to obtain thick paste;
step 2: adding a mixed solvent with the volume of one fourth to one half of that of the wastewater into the thick paste, stirring and extracting for 30 minutes at 25-50 ℃, standing and layering; the mixed solvent consists of a solvent A and a solvent B, wherein the solvent A is one of ethanol, isopropanol or acetone, the solvent B is one of ethyl acetate, methyl acetate, dichloromethane or diethyl ether, and the solvent proportion in the mixed solvent is as follows: solvent A and solvent B are 1: 1-1: 1.5 (V/V);
and step 3: taking a mixed solvent layer, recovering the solvent until the solvent is completely obtained, adding water with the mass of 3-9 times of that of the shikimic acid crude product to dissolve the shikimic acid crude product, adding a solvent B into the aqueous solution, wherein the adding amount of the solvent B is one third to one half of that of the aqueous solution, and extracting and removing impurities for 2-3 times;
and 4, step 4: separating a water layer, recovering the solvent, concentrating until the concentration of shikimic acid crystals is 0.4-0.6 g/ml, and then cooling and crystallizing at 10-25 ℃ for 24-96 hours;
and 5: adding a solvent A with the mass of 0.5-2 times of that of the shikimic acid crude product into the crystal, stirring, pulping, filtering, and washing a filter cake with the solvent A; drying the filter cake to obtain shikimic acid finished product with the content of more than 98 percent.
Preferably, the solvent a in the mixed solvent is acetone, and the solvent B is ethyl acetate.
In order to further improve the final extraction amount of shikimic acid in the chromatography wastewater, the step 2 and the step 3 of separating the mixed solvent layer can be repeatedly operated for a plurality of times, specifically, the mixed solvent is added into the thick paste for stirring and standing for layering for the first time, the mixed solvent layer is separated, then the mixed solvent is continuously added into the thick paste at the lower layer of the mixed solvent layer for stirring and standing for layering, the mixed solvent layer is separated, after the operation is repeatedly performed for a plurality of times, all the separated mixed solvent layers are combined, then the solvent is recycled to be complete shikimic acid crude products, and then the next related operation is performed. The operations of mixing and stirring, standing for layering and separating the mixed solvent layer are adopted for multiple times, so that shikimic acid in the thick paste can be dissolved in the mixed solvent to the maximum extent, and the final extraction amount of shikimic acid is improved.
Preferably, the step 3 of recovering the solvent to completely obtain the crude shikimic acid is to heat and evaporate the separated mixed solvent layer to completely obtain the crude shikimic acid under the conditions of less than-0.08 MPa and 60-70 ℃.
Preferably, the solvent is recovered in the step 4 and concentrated to ensure that the shikimic acid crystal concentration is 0.4-0.6 g/ml, namely the solvent is recovered by heating and evaporating the separated water layer under the conditions of less than-0.08 MPa and 60-70 ℃, and the solvent is continuously evaporated until the shikimic acid concentration is 0.4-0.6 g/ml.
Preferably, the drying of the filter cake in the step 5 refers to drying for 6-7h under the condition that the vacuum degree is less than-0.08 MPa and the temperature is 70-80 ℃.
Compared with the prior art, the method utilizes the special properties of the mixed solvent to change the distribution ratio of shikimic acid and impurities in two phases of a liquid-liquid extraction system, achieves the selective enrichment of shikimic acid, does not use acid or alkali in the production process, recycles the solvent, has simple operation, is suitable for industrial production and has high product purity. The method has great significance for the deep development of the ginkgo leaf resource and is expected to have good economic benefit.
Detailed Description
The technical solution in the implementation of the present invention is described in detail below with reference to embodiments, which are only a part of embodiments of the present invention, but not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments of the present invention without making any creative effort, shall fall within the protection scope of the present invention.
In the following examples, raw materials used for preparing shikimic acid are ginkgo leaf extract chromatography wastewater, which is an effluent of concentrated and clarified ginkgo leaf extract through macroporous adsorbent resin column chromatography, and is generated in the process of preparing ginkgo leaf extract according to the Chinese pharmacopoeia.
The dry matter mentioned in the examples refers to the residue of the solution after removal of the solvent, and the dry matter ratio refers to the percentage of the mass of the residue relative to the volume of the solution.
Example 1
Step 1: taking 2L of folium Ginkgo extract chromatography wastewater, wherein the content of shikimic acid in the wastewater is 0.012g/ml, the dry matter content is 0.07g/ml, and the shikimic acid content in the dry matter is 17.1%, and concentrating the wastewater under reduced pressure to 150ml in volume to obtain thick paste;
step 2.1: adding 500ml of acetone-ethyl acetate mixed solvent into the thick paste, wherein the ratio of acetone to ethyl acetate is 1:1, stirring and extracting in a water bath at 50 ℃ for 30 minutes, standing and layering (at this time, part of shikimic acid is dissolved in the mixed solvent and is positioned at the upper layer, and shikimic acid which is not dissolved in the mixed solvent temporarily and insoluble matters in the thick paste are positioned at the lower layer);
step 2.2: taking the mixed solvent layer, adding 500ml of the mixed solvent which is the same as the mixed solvent in the step 2.1 into the lower thick paste, stirring and extracting for 30 minutes in a water bath at 50 ℃, standing and layering;
and step 3: repeating the step 2.2 for 4 times, combining all the divided mixed solvent layers (the shikimic acid in the thick paste can be dissolved in the mixed solvent to the maximum extent by mixing, stirring and standing for layering for multiple times, so that the extraction amount of the shikimic acid is improved), recovering the solvent until the solvent is completely obtained to obtain 25.8g of crude shikimic acid, adding 100ml of water to dissolve the crude shikimic acid (namely adding water to the crude shikimic acid to dissolve the crude shikimic acid) to obtain 130ml of aqueous solution, adding 50ml of ethyl acetate to the aqueous solution to extract and remove impurities, and extracting for 2 times;
and 4, step 4: separating water layer, recovering solvent, and concentrating until shikimic acid concentration is 0.4 g/ml; then cooling and crystallizing for 24 hours at 10 ℃;
and 5: adding 20ml acetone into the crystal, stirring, pulping, filtering, and washing the filter cake (i.e. cake shikimic acid) with a small amount of acetone; finally, the filter cake is dried to obtain 10.7g shikimic acid finished product with the content of 99.6 percent.
Example 2
Step 1: taking 2L of folium Ginkgo extract chromatography wastewater, wherein the content of shikimic acid in the wastewater is 0.006g/ml, the dry matter content is 0.05g/ml, and the shikimic acid content in the dry matter is 12.2%, and concentrating the wastewater under reduced pressure to 110ml to obtain thick paste;
step 2.1: adding 500ml of acetone-methyl acetate mixed solvent into the thick paste, wherein the ratio of acetone to methyl acetate is 1:1.5, stirring and extracting in water bath at 25 ℃ for 30 minutes, standing and layering (at this time, part of shikimic acid is dissolved in the mixed solvent and is positioned at the upper layer, and shikimic acid which is not dissolved in the mixed solvent temporarily and insoluble matters in the thick paste are positioned at the lower layer);
step 2.2: taking the mixed solvent layer, adding 500ml of the mixed solvent which is the same as the mixed solvent in the step 2.1 into the lower thick paste, stirring and extracting for 30 minutes in a water bath at 25 ℃, standing and layering;
and step 3: repeating the operation of the step 2.2 for 5 times, combining all the divided mixed solvent layers (the shikimic acid in the thick paste can be dissolved in the mixed solvent to the maximum extent by mixing, stirring and standing for layering for multiple times, the extraction amount of the shikimic acid is improved), recovering the solvent until the solvent is completely obtained to obtain 11.3g of shikimic acid crude product, adding 100ml of water to dissolve residues to obtain 110ml of aqueous solution, adding 50ml of methyl acetate into the aqueous solution to extract and remove impurities, and extracting for 2 times;
and 4, step 4: separating water layer, recovering solvent, and concentrating until shikimic acid concentration is 0.5 g/ml; then cooling and crystallizing for 72 hours at the temperature of 20 ℃;
and 5: to the crystals, 20ml of acetone was added, stirred for beating, filtered, and the filter cake was washed with a small amount of acetone. Finally, the filter cake is dried to obtain 5.2g shikimic acid finished product with the content of 99.5 percent.
Example 3
Step 1: taking 2L of folium Ginkgo extract chromatography wastewater, wherein the content of shikimic acid in the wastewater is 0.035g/ml, the dry matter content is 0.12g/ml, and the shikimic acid content in the dry matter is 29.2%, and concentrating the wastewater under reduced pressure to 260ml to obtain thick paste;
step 2.1: adding 1000ml of ethanol-dichloromethane mixed solvent into the thick paste, wherein the ratio of isopropanol to ethyl acetate is 1:1, stirring and extracting for 30 minutes in a water bath at 25 ℃, standing and layering;
step 2.2, dividing a mixed solvent layer, adding 1000ml of the mixed solvent which is the same as the mixed solvent layer in the step 2.1 into the lower thick paste, stirring and extracting for 30 minutes in a water bath at 25 ℃, standing and layering;
and step 3: repeating the step 2.2 for 2 times, combining all the divided mixed solvent layers, recovering the solvent until the shikimic acid crude product is 57.3 completely, adding 200ml of water to dissolve the residue to obtain 290ml of aqueous solution, adding 100ml of dichloromethane into the aqueous solution, extracting and removing impurities for 3 times;
and 4, step 4: the aqueous layer was separated, the solvent was recovered and concentrated to give a shikimic acid concentration of 0.6 g/ml. Cooling and crystallizing at 25 deg.c for 96 hr;
and 5: to the crystals, 50ml of ethanol was added, stirred and slurried, filtered, and the filter cake was washed with a small amount of ethanol. The filter cake is dried to obtain the shikimic acid finished product 37.2g with the content of 98.6 percent.
Example 4
Step 1: taking 2L of ginkgo leaf extract chromatographic wastewater, wherein the content of shikimic acid in the wastewater is 0.015g/ml, the dry matter proportion is 0.11g/ml, and the content of shikimic acid in the dry matter is 13.6%, and concentrating the wastewater under reduced pressure until the volume is 110ml to obtain thick paste;
step 2.1: adding 1000ml of isopropanol-diethyl ether mixed solvent into the thick paste, wherein the ratio of isopropanol to diethyl ether is 1:1.5, stirring and extracting in a water bath at 30 ℃ for 30 minutes, standing and layering;
step 2.2, dividing a mixed solvent layer, adding 1000ml of the mixed solvent which is the same as the mixed solvent layer in the step 2.1 into the lower thick paste, stirring and extracting for 30 minutes in a water bath at the temperature of 30 ℃, standing and layering;
and step 3: repeating the step 2.2 for 3 times, combining all the divided mixed solvent layers, recovering the solvent until the shikimic acid crude product is completely obtained 34.2, adding 100ml of water to dissolve the residue to obtain 120ml of aqueous solution, adding 40ml of diethyl ether into the aqueous solution, extracting and removing impurities for 3 times;
and 4, step 4: the aqueous layer was separated, the solvent was recovered and concentrated to give a shikimic acid concentration of 0.6 g/ml. Cooling and crystallizing at 15 deg.c for 72 hr;
and 5: to the crystals, 20ml of isopropyl alcohol was added, and the mixture was stirred, slurried, filtered, and the filter cake was washed with a small amount of isopropyl alcohol. The filter cake is dried to obtain 16.3g shikimic acid finished product with the content of 98.5 percent.
Comparing several examples, it can be seen that when solvent A is acetone and solvent B is ethyl acetate, the purity of the product is the highest, reaching more than 99%.
The step 3 of recovering the solvent to completely obtain the crude shikimic acid in the above embodiments means heating and evaporating the separated mixed solvent layer to completely obtain the crude shikimic acid under the conditions of less than-0.08 MPa and 60-70 ℃. The solvent recovered at this time is a main component of the mixed solvent, and as the solvent recovered in example 1, acetone and ethyl acetate, acetone and methyl acetate, ethanol and dichloromethane, and isopropanol and diethyl ether were recovered in example 2, example 3, and example 4, the recovered solvent was reusable.
The solvent is recovered in the step 4 in each embodiment and concentrated to ensure that the shikimic acid crystal concentration is 0.4-0.6 g/ml, namely the solvent is recovered by heating and evaporating the separated water layer under the conditions of less than-0.08 MPa and 60-70 ℃, and the solvent is continuously evaporated until the shikimic acid concentration is 0.4-0.6 g/ml. The solvent recovered at this time is mainly the solvent B added in step 3 for extraction and impurity removal, and the recovered solvent can be reused as in example 1, in which ethyl acetate is mainly recovered, in example 2, methyl acetate is mainly recovered, in example 3, dichloromethane is mainly recovered, and in example 4, diethyl ether is mainly recovered.
The drying of the filter cake in the step 5 in each embodiment refers to the drying for 6 to 7 hours under the conditions that the vacuum degree is less than minus 0.08MPa and the temperature is between 70 and 80 ℃.
The invention utilizes that shikimic acid is easy to dissolve in water, has certain solubility in a solvent A such as ethanol, isopropanol or acetone, but has extremely low solubility in a solvent B such as ethyl acetate, methyl acetate, dichloromethane or diethyl ether; similarly, other water-soluble impurities in the wastewater, such as saccharides, tannins, proteins and the like, which have the characteristic of smaller solubility in the solvent A and the solvent B than shikimic acid, are extracted by using a mixed solvent consisting of the solvent A and the solvent B. The mixed solvent has certain solubility to shikimic acid, so that the mixed solvent has certain extraction efficiency, and simultaneously can reduce the impurity content in the dry matter of the extract of the mixed solvent. In addition, in the extraction system consisting of water and the mixed solvent, although the distribution ratio of shikimic acid in the water phase is higher than that of shikimic acid in the mixed solvent phase, the content of shikimic acid in the coherent substance of the mixed solvent is far higher than that of shikimic acid in the dry substance of the water phase, and the dry substance content of shikimic acid in the mixed solvent phase can exceed 60 percent, thereby ensuring that the next crystallization is carried out efficiently.
In conclusion, the invention adopts the mixed solvent for extraction, changes the distribution ratio of shikimic acid and impurities in the two phases of the liquid-liquid extraction system by utilizing the special properties of the mixed solvent, namely utilizes the complementary advantages of the mixed solvent to increase the distribution ratio difference of shikimic acid and impurities in the two phases of the liquid-liquid extraction system, further realizes the selective enrichment of shikimic acid, ensures that the shikimic acid content in the enriched feed liquid dry matter reaches or exceeds the minimum content requirement for the smooth crystallization of shikimic acid, and then carries out the refining by a crystallization method, thus obtaining the product with high purity. In addition, acid and alkali are not used in the production process, and the used solvent can be recycled repeatedly, so that the environmental impact is small.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
Furthermore, it should be understood that although the present description refers to embodiments, not every embodiment may contain only a single embodiment, and such description is for clarity only, and those skilled in the art should make the description as a whole, and the embodiments may be appropriately combined to form other embodiments understood by those skilled in the art.
Claims (1)
1. A method for extracting shikimic acid from ginkgo leaf extract chromatography wastewater is characterized by comprising the following steps:
step 1: taking macroporous adsorption resin chromatography wastewater under the item of extracting ginkgo leaf extract according to Chinese pharmacopoeia, and concentrating the wastewater until the water content is 15-25% to obtain thick paste;
step 2: adding a mixed solvent with the volume of one fourth to one half of that of the wastewater into the thick paste, stirring and extracting for 30 minutes at 25-50 ℃, standing and layering; the mixed solvent consists of a solvent A and a solvent B, wherein the solvent A is acetone, the solvent B is ethyl acetate, and the solvent ratio in the mixed solvent is as follows: the volume ratio of the solvent A to the solvent B is 1: 1-1: 1.5;
and step 3: taking a mixed solvent layer, recovering the solvent until the solvent is completely obtained, adding water with the mass of 3-9 times of that of the shikimic acid crude product to dissolve the shikimic acid crude product, adding a solvent B into the aqueous solution, wherein the adding amount of the solvent B is one third to one half of that of the aqueous solution, and extracting and removing impurities for 2-3 times;
and 4, step 4: separating a water layer, recovering the solvent, concentrating until the concentration of shikimic acid crystals is 0.4-0.6 g/ml, and then cooling and crystallizing at 10-25 ℃ for 24-96 hours;
and 5: adding a solvent A with the mass of 0.5-2 times of that of the shikimic acid crude product into the crystal, stirring, pulping, filtering, and washing a filter cake with the solvent A; drying the filter cake to obtain shikimic acid finished product, wherein the content of shikimic acid is more than 98%;
the step 3 of recovering the solvent until the crude shikimic acid is completely obtained refers to heating and evaporating the separated mixed solvent layer under the conditions of less than-0.08 MPa and 60-70 ℃ until the crude shikimic acid is completely obtained;
the step 4 of recovering the solvent and concentrating until the crystal concentration of shikimic acid is 0.4-0.6 g/ml means that the separated water layer is heated and evaporated under the conditions of less than-0.08 MPa and 60-70 ℃ to realize the recovery of the solvent, and the solvent is continuously evaporated until the concentration of shikimic acid is 0.4-0.6 g/ml;
the filter cake drying in the step 5 refers to drying for 6-7h under the conditions that the vacuum degree is less than-0.08 MPa and the temperature is 70-80 ℃.
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