CN109705127B - Anti-emulsification preparation method of plant-derived sodium copper chlorophyllin - Google Patents
Anti-emulsification preparation method of plant-derived sodium copper chlorophyllin Download PDFInfo
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Abstract
The invention discloses an anti-emulsification preparation method of plant source sodium copper chlorophyllin, which takes ginkgo leaves as raw materials, ethanol is extracted to obtain black extractum, ethanol solvent and petroleum ether solvent with different concentrations are used for forward and backward extraction, the emulsification and layering phenomena are greatly reduced, the ginkgolic acid content in the obtained sodium copper chlorophyllin is less than 1ppm, and the absorbance of E405nm is more than or equal to 600.
Description
Technical Field
The invention relates to the field of plant extraction and chemistry, in particular to an anti-emulsification preparation method of plant-derived sodium copper chlorophyllin.
Background
Sodium copper chlorophyllin is a pigment product derived from natural sources, including animal sources (such as silkworm excrement) and plant sources (such as leaves of plants including alfalfa, bamboo, and ginkgo), and is produced by saponifying chlorophyll to convert into chlorophyllin, acidifying copper to obtain copper chlorophyllin acid, and neutralizing copper chlorophyllin acid with sodium hydroxide to obtain water-soluble sodium copper chlorophyllin. GB 26406 & ltone & gt 2011 discloses a standard of sodium copper chlorophyllin obtained by extracting silkworm excrement by using an organic solvent, saponifying and substituting copper as a food additive, wherein the content of free copper is required to be strictly controlled during production, and the absorbance E405nm is more than or equal to 568. With the gradual improvement of the cognition of people on sodium copper chlorophyllin, more and more people select a plant extraction mode to obtain sodium copper chlorophyllin, and the requirement on a preparation process is very high.
The Ginkgo Biloba Extract (GBE) is a product which is obtained by taking the leaves of Ginkgo Biloba Ginko Biloba L, extracting by a solvent, enriching and purifying by column chromatography, and the content of active ingredients of the Ginkgo Biloba Extract is not less than 24 wt% of Ginkgo flavone and not less than 26 wt% of ginkgolide. The ginkgo leaf extract has the effects of expanding blood vessels, improving microcirculation, dissolving thrombus and the like, can be prepared into various preparations by taking the ginkgo leaf extract as a raw material, is used for treating various cardiovascular and cerebrovascular diseases, and is widely applied to the fields of medicines, health-care products, food additives, functional beverages, cosmetics and the like. The content of free copper is controlled by utilizing the sodium copper chlorophyllin prepared from folium ginkgo, and ginkgolic acid in the folium ginkgo extract is a main harmful impurity in the product, so that the separation is not easy, and the preparation and purification of the product are greatly influenced.
Chinese patent CN 108451988A discloses a method for preparing sodium copper chlorophyllin by hydrolyzing ginkgo leaf with enzyme, which requires a large amount of protease and cellulase, and can not effectively reduce ginkgolic acid content in the product, so that the product has excessive impurities and is turbid after being dissolved in water.
Chinese patent CN 104725387a discloses a method for extracting sodium copper chlorophyllin from ginkgo biloba leaf extract by mixing ethanol, isopropanol and solvent oil No. 6, the method uses a large amount of solvent oil No. 6, the system contains a plurality of alcohol phases, the post-treatment step is added, an emulsion layer with a certain thickness can be obtained after saponification reaction in the step, the content of impurities in the product is high, and precipitates are formed after the product is dissolved in water. And the method can not effectively reduce ginkgolic acid (20-50 ppm) in the system.
Disclosure of Invention
The purpose of the invention is as follows: the invention aims to provide a preparation method of plant-derived sodium copper chlorophyllin, which is used for obtaining high-yield sodium copper chlorophyllin with transparent aqueous solution by optimizing a purification process and eliminating an emulsifying layer so as to greatly reduce the content of ginkgolic acid.
The technical scheme is as follows: in order to achieve the above object, the present invention provides an anti-emulsification method for preparing plant-derived sodium copper chlorophyllin, comprising the following steps:
(1) pulverizing folium Ginkgo, extracting with alcohol solution, filtering, and concentrating the filtrate to obtain black extract;
(2) adding the black extract into an alcohol solution of petroleum ether, stirring, standing and layering; separating out petroleum ether phase, adding a first alcohol solvent, stirring, washing with alcohol, standing and layering;
(3) adding a second alcohol solvent and dilute alkali into the petroleum ether solution finally obtained in the previous step, and separating out a transparent petroleum ether phase;
(4) adding an alcoholic solution of strong base into the transparent petroleum ether phase for saponification reaction, and standing for layering; separating out alcohol phase, adding petroleum ether, stirring and extracting;
(5) adding sulfuric acid into the alcohol phase solution finally obtained in the previous step for acidification, and then adding petroleum ether for stirring and extraction;
(6) adding copper sulfate into the alcohol phase obtained by the previous extraction step, heating and refluxing until the color turns green, cooling, concentrating until no alcohol exists, washing with water, concentrating, and drying to obtain copper chlorophyllin acid;
(7) redissolving the chlorophyll keto acid, adding equivalent sodium hydroxide for neutralization, and drying to obtain the water-soluble sodium copper chlorophyllin.
The method of the invention comprises the following steps: and (2) carrying out multiple separation and purification on the black ginkgo leaf extract obtained by leaching by using alcohol and petroleum ether, firstly, extracting and separating impurities in a petroleum ether phase by using an alcohol solvent, after saponification reaction, transferring active ingredients from the petroleum ether phase to the alcohol phase, then, extracting and separating the impurities in the alcohol phase by using the petroleum ether, and then, carrying out acidification, petroleum ether extraction and copper substitution reaction. Because the emulsification phenomenon before saponification can directly influence the saponification reaction and the product purity, the main problem solved by the invention is how to select a proper extraction reagent and how to separate, thereby minimizing an emulsion layer. The problem of the emulsifying layer is effectively solved, so that the purity of the sodium copper chlorophyllin is improved, the product chromaticity and the transparency are excellent, and the content of ginkgolic acid in the system is further reduced.
The method can prepare sodium copper chlorophyllin by using black waste stickum generated in the extraction process as raw material while producing folium Ginkgo extract, thereby realizing comprehensive utilization of folium Ginkgo, reducing production cost, and simultaneously reducing environmental pollution.
In the step (1), 85-95% (V/V) ethanol solution is added into the crushed ginkgo leaves for reflux extraction, the water bath temperature is 85-90 ℃, and the filtrate is combined after extraction and filtration. Preferably, the steps of reflux extraction and filtration of the crushed ginkgo leaves in the step (1) are repeated for 1 to 2 times. More preferably, the step (1) is carried out by refluxing and leaching with 90% (V/V) ethanol solution, and the refluxing time is not more than 3 hours each time.
In the step (2), the first alcohol solvent is 60-95% (V/V) ethanol solution, alcohol washing is carried out for 2-3 times, and petroleum ether phases are combined. Preferably, the ethanol solution of 65 percent to 80 percent (V/V) is used, and more preferably, the ethanol solution of 70 percent (V/V) is used as the first alcohol solvent. In the step (3), the second alcohol solvent is 45-85% (V/V) ethanol solution, and the step is carried out for 1-3 times. Preferably, the second alcohol solvent is 50-65% (V/V) ethanol solution.
It is noted that in the chemical field, conventional emulsion breaking treatments for emulsification phenomena generally promote stratification by adding heat, methanol, acetone, inorganic salts, acids, and the like. However, in the present invention, since two organic phases are used for extraction, the addition of a plurality of organic solvents affects the extraction effect and is not favorable for increasing the recovery difficulty of the solvent during production, and the addition of inorganic salts and acids cannot completely break the emulsification. In the step (2) and the step (3), the concentration of the ethanol solvent is distinguished for sequential treatment, the thickness of an emulsion layer is obviously reduced under the condition of not adding an additional solvent or a demulsifier, the concentration of the alcohol solvent needs to be particularly noticed during extraction, and if the concentration is too high, the layering is not obvious; the concentration is too low, the emulsification is serious, and the impurity removal effect is poor. In the step (3), the dilute alkali is added, and the concentration of the ethanol is controlled, so that an unexpected complete demulsification effect is obtained.
The dilute alkali in the step (3) is any one of ammonia water, sodium hydroxide, potassium hydroxide and sodium carbonate solution. Preferably sodium hydroxide solution.
Further, the diluted base is added in an amount of 0.05 to 5% (m/V), preferably 0.05 to 1% (m/V), more preferably 0.1 to 0.2% (m/V) of the second alcohol solvent.
The strong base in the step (4) is any one of NaOH and KOH, and is preferably potassium hydroxide. Adding alcohol solution of strong base, and saponifying for 3-5 hr. Adding strong base 1.0-5.0% (m/V) of alcohol solution, adding petroleum ether, and extracting at room temperature for 1-3 times.
Adding sulfuric acid in the step (5), adjusting the pH value to 1-4, preferably 1.5-2.5, and then adding petroleum ether to extract for 1-3 times at normal temperature.
And (3) in the copper substitution reaction in the step (6), adding a copper sulfate solution, heating to 40-60 ℃, refluxing for 10 minutes until the solution gradually turns green, stopping refluxing after 1 hour, and cooling. In the step (6), the water washing is performed by using any one of methyl acetate, ethyl acetate and propyl acetate, preferably ethyl acetate. Adding water during extraction, discarding the lower water phase, and washing with water for 1-2 times.
According to the invention, when ethanol and petroleum ether are used for mutual extraction, the ethanol and the petroleum ether are mixed according to the volume ratio of 1: 3-1: 5, preferably the volume ratio is 1:4, for example, 100ml of ethanol and 400ml of petroleum ether are used for extraction of 100g of ginkgo biloba extract.
Has the advantages that: the invention only uses two solvents of ethanol and petroleum ether for extraction and purification, thereby avoiding the influence of various organic solvents in the system on extraction and delamination; the ginkgo leaf crushing and leaching adopts a mode of refluxing for a plurality of times in a short time and combining leaching liquor, so that the product yield is improved; the method comprises the steps of removing impurities in a petroleum ether phase and an alcohol phase in sequence, remarkably reducing emulsification layering before and after saponification by controlling the concentration of a solvent, ensuring the yield and purity of a product, and effectively removing more than 90% of ginkgoic acid, wherein the absorbance of the sodium copper chlorophyllin E405nm obtained by the method is more than or equal to 600, the absorbance ratio is 3.1-3.58, the copper complex is more than or equal to 6.2%, the content of ginkgoic acid is less than 1.0ppm, and the product yield is as high as 0.4%.
Detailed Description
As further illustrated in the following specific examples of the present invention, the alcohol solvent is expressed in volume percent (V/V) without additional description.
Example 1
1）Preparation of ginkgo leaf extract
Crushing 100g of ginkgo leaves, performing primary leaching and reflux leaching for 3 hours by using 90% ethanol, controlling the temperature of a water bath to be 90 ℃, and filtering by using gauze; then leaching for 3 hours again, filtering by gauze, combining the filtrates, heating and stirring uniformly, cooling to room temperature, and filtering for later use. Concentrating under reduced pressure to obtain extract, dissolving in water, and centrifuging to obtain black viscous substance.
2）Extraction of petroleum ether phase to remove impurities
Adding 100ml of 95% ethanol and 400ml of petroleum ether into the extract, stirring for 0.5-1.5 hours, filtering under reduced pressure, transferring into a separating funnel, standing to obtain an obvious boundary layer, and discarding the lower alcohol phase. Then adding 70% ethanol, stirring, washing with alcohol for 30 min, standing for layering, and removing the lower alcohol phase. The alcohol wash was performed 2 times in total.
Adding 62% ethanol and 0.15% (m/V) sodium hydroxide into the petroleum ether phase after the alcohol washing, stirring for 30 minutes, discarding the lower alcohol phase, wherein the pH of the alcohol phase is 9-10, then adding 62% ethanol and 0.15% (m/V) sodium hydroxide again, stirring again, standing for layering, and the pH of the alcohol phase is 11-12. A clear petroleum ether phase was obtained.
3）Saponification
Adding 95% alcoholic solution with sodium hydroxide concentration of 4.0% (m/V) into the transparent petroleum ether phase, hydrolyzing at room temperature for 4 hr, standing to separate lower layer alcohol phase.
4）Removing impurities by alcohol phase extraction
And adding petroleum ether into the alcohol phase after the saponification reaction to extract and remove impurities, and repeating twice. Adding 50ml of petroleum ether into the mixture for extraction, stirring the mixture for 10 minutes, and standing the mixture for layering.
5）Acidification
Adding 9M sulfuric acid into the alcohol phase solution finally obtained in the previous step for acidification, adjusting the pH value to 2-3, stirring for 10 minutes, adding petroleum ether into the filtrate for extraction for three times, and keeping the alcohol phase.
6）Copper substitution reaction
Adding 20% (m/V) copper sulfate solution into the alcohol phase obtained by the previous step, refluxing at 55 deg.C for 60 min, gradually turning the alcohol phase to green, cooling after the reaction is completed, and concentrating until no alcohol is present.
7）Preparation of finished product
After concentration, the mixture was washed with ethyl acetate three times, and the lower aqueous phase was discarded. Concentrating ethyl acetate phase, adding 95% ethanol, evaporating water and ethanol in water bath, oven drying to obtain dry product 0.41 g.
The yield of sodium copper chlorophyllin obtained by the method is 0.41%, the absorbance of E405nm is 600, the absorbance of E630nm is 191, the absorbance ratio is 3.14, and the content of ginkgolic acid is less than 1 ppm.
Example 2
1）Ginkgo leaf extractPreparation of
Crushing 100g of ginkgo leaves, performing primary leaching and reflux leaching for 3 hours by using 90% ethanol, controlling the temperature of a water bath to be 90 ℃, and filtering by using gauze; then leaching for 3 hours again, filtering by gauze, combining the filtrates, heating and stirring uniformly, cooling to room temperature, and filtering for later use. Concentrating under reduced pressure to obtain extract, dissolving in water, and centrifuging to obtain black viscous substance.
2）Extraction of petroleum ether phase to remove impurities
Adding 100ml of 95% ethanol and 400ml of petroleum ether into the extract, stirring for 0.5-1.5 hours, filtering under reduced pressure, transferring into a separating funnel, standing to obtain an obvious boundary layer, and discarding the lower alcohol phase. Then adding 60% ethanol, stirring, washing with alcohol for 30 min, standing for layering, and discarding the lower alcohol phase. The alcohol wash was performed 2 times in total.
Then adding 60% ethanol and 0.10% (m/V) sodium hydroxide into the petroleum ether phase after the alcohol washing, stirring for 30 minutes, discarding the lower alcohol phase, wherein the pH of the petroleum ether phase is 12-13, then adding 60% ethanol and 0.10% (m/V) sodium hydroxide again, stirring again, standing and layering. A clear petroleum ether phase was obtained.
3）Saponification
Adding 95% alcoholic solution with sodium hydroxide concentration of 3.0% (m/V) into the transparent petroleum ether phase, hydrolyzing at room temperature for 5 hr, standing to separate lower layer alcohol phase.
4）Removing impurities by alcohol phase extraction
And adding petroleum ether into the alcohol phase after the saponification reaction for extraction and impurity removal, adding 50ml of petroleum ether for extraction, stirring for 10 minutes, and standing for layering.
5）Acidification
Adding 9M sulfuric acid into the alcohol phase solution finally obtained in the previous step for acidification, adjusting the pH value to 2-3, stirring for 10 minutes, performing suction filtration, adding petroleum ether into the filtrate for extraction for three times, and keeping the alcohol phase.
6）Copper substitution reaction
Adding 20% (m/V) copper sulfate solution into the alcohol phase obtained by the previous step, refluxing at 55 deg.C for 60 min, gradually turning the alcohol phase to green, cooling after the reaction is completed, and concentrating until no alcohol is present.
7）Preparation of finished product
After concentration, the mixture was washed with ethyl acetate three times, and the lower aqueous phase was discarded. Concentrating ethyl acetate phase, adding ethanol, evaporating water and ethanol in water bath, oven drying to obtain dried product 0.39 g.
The yield of sodium copper chlorophyllin obtained by the method is 0.39%, the absorbance of E405nm is 630, and the absorbance of E630nm is 190; the absorbance ratio is 3.31, and the ginkgolic acid content is less than 1 ppm.
Example 3
1）Preparation of ginkgo leaf extract
Crushing 100g of ginkgo leaves, performing primary leaching and reflux leaching for 3 hours by using 90% ethanol, controlling the temperature of a water bath to be 90 ℃, and filtering by using gauze; then leaching for 3 hours again, filtering by gauze, combining the filtrates, heating and stirring uniformly, cooling to room temperature, and filtering for later use. Concentrating under reduced pressure to obtain extract, dissolving in water, and centrifuging to obtain black viscous substance.
2）Extraction of petroleum ether phase to remove impurities
Adding 100ml of 95% ethanol and 300ml of petroleum ether into the extract, stirring for 0.5-1.5 hours, filtering under reduced pressure, transferring into a separating funnel, standing to obtain an obvious boundary layer, and discarding the lower alcohol phase. Then adding 95% ethanol, stirring, washing with alcohol for 30 min, standing for layering, and discarding the lower alcohol phase. The alcohol wash was performed 2 times in total.
3）Saponification
Adding 95% alcoholic solution with sodium hydroxide concentration of 4.0% (m/V) into the transparent petroleum ether phase, hydrolyzing at room temperature for 4 hr, standing to separate lower layer alcohol phase.
4）Removing impurities by alcohol phase extraction
And adding petroleum ether into the alcohol phase after the saponification reaction to extract and remove impurities, and repeating twice. Adding 50ml of petroleum ether into the mixture for extraction, stirring the mixture for 10 minutes, and standing the mixture for layering.
5）Acidification
Adding 9M sulfuric acid into the alcohol phase solution finally obtained in the previous step for acidification, adjusting the pH value to 2-3, stirring for 10 minutes, performing suction filtration, adding petroleum ether into the filtrate for extraction for three times, and keeping the alcohol phase.
6）Copper substitution reaction
Adding 20% (m/V) copper sulfate solution into the alcohol phase obtained by the previous step, refluxing at 55 deg.C for 60 min, gradually turning the alcohol phase to green, cooling after the reaction is completed, and concentrating until no alcohol is present.
7）Preparation of finished product
After concentration, the mixture was washed with ethyl acetate three times, and the lower aqueous phase was discarded. Concentrating ethyl acetate phase, adding ethanol, evaporating water and ethanol in water bath, oven drying to obtain dried product 2.0 g.
The yield of sodium copper chlorophyllin obtained by the method is 2.0%, the absorbance of E405nm is 150, the absorbance of E630nm is 89, the absorbance ratio is 1.68, and the content of ginkgolic acid is more than 10000 ppm. Although the product obtained by the method has high yield, the product has more impurities, can not be dried and is sticky, and a large amount of precipitate is generated when the product is added into water.
As can be seen from the above examples, the technical effects of the present invention as in example 1 were not achieved by using conventional concentrations of alcohol and extraction methods for purification.
Claims (10)
1. An anti-emulsification preparation method of plant source sodium copper chlorophyllin is characterized by comprising the following steps:
(1) pulverizing folium Ginkgo, extracting with alcohol solution, filtering, and concentrating the filtrate to obtain black extract;
(2) adding the black extract into an alcohol solution of petroleum ether, stirring, standing and layering; separating out a petroleum ether phase, adding a first alcohol solvent, stirring, washing with alcohol, standing and layering, wherein the first alcohol solvent is 60-95% (V/V) ethanol solution;
(3) adding a second alcohol solvent and dilute alkali into the petroleum ether solution finally obtained in the previous step, and separating out a transparent petroleum ether phase;
(4) adding an alcoholic solution of strong base into the transparent petroleum ether phase for saponification reaction, and standing for layering; separating out alcohol phase, adding petroleum ether, stirring and extracting;
(5) adding sulfuric acid into the alcohol phase solution finally obtained in the previous step for acidification, and then adding petroleum ether for stirring and extraction;
(6) adding copper sulfate into the alcohol phase obtained by the previous extraction step, heating and refluxing until the color turns green, cooling, concentrating until no alcohol exists, washing with water, concentrating, and drying to obtain copper chlorophyllin acid;
(7) redissolving the chlorophyll keto acid, adding equivalent sodium hydroxide for neutralization, and drying to obtain the water-soluble sodium copper chlorophyllin.
2. The method for preparing plant-derived sodium copper chlorophyllin according to claim 1, wherein: in the step (1), 85-95% (V/V) ethanol solution is added into the crushed ginkgo leaves for reflux extraction, the water bath temperature is 85-90 ℃, and the filtrate is combined after extraction and filtration.
3. The method for preparing plant-derived sodium copper chlorophyllin according to claim 1, wherein: the alcohol washing in the step (2) is carried out for 2-3 times.
4. The method for preparing plant-derived sodium copper chlorophyllin according to claim 1, wherein: the second alcohol solvent is 45-85% (V/V) ethanol solution, and the step (3) is carried out for 1-3 times.
5. The method for preparing plant-derived sodium copper chlorophyllin according to claim 4, wherein: the dilute alkali in the step (3) is any one of ammonia water, sodium hydroxide, potassium hydroxide and sodium carbonate.
6. The method for preparing plant-derived sodium copper chlorophyllin according to claim 5, wherein: the addition amount of the dilute alkali is 0.05-5% (m/V) of the second alcohol solvent.
7. The method for preparing plant-derived sodium copper chlorophyllin according to claim 1, wherein: and (3) adding an alcoholic solution of strong base into the strong base in the step (4) to perform saponification reaction for 3-5 hours, wherein the strong base in the step (4) is any one of NaOH and KOH.
8. The method according to claim 7, wherein the plant-derived sodium copper chlorophyllin is prepared by the following steps: in the step (4), the adding amount of the strong alkali is 1.0-5.0% (m/V) of the alcoholic solution, and petroleum ether is added for normal-temperature extraction for 1-3 times.
9. The method for preparing plant-derived sodium copper chlorophyllin according to claim 1, wherein: and (5) adding sulfuric acid, adjusting the pH value to 1-4, and then adding petroleum ether to extract for 1-3 times at normal temperature.
10. The method for preparing plant-derived sodium copper chlorophyllin according to claim 1, wherein: and (4) extracting any one of methyl acetate, ethyl acetate and propyl acetate for water washing in the step (6), adding water, discarding the lower water phase, and repeating the water washing for 1-2 times.
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| CN110200021A (en) * | 2019-07-23 | 2019-09-06 | 江苏贝斯康药业有限公司 | A kind of preparation method of ginkgo biloba leaf total organic salt |
| CN112010863A (en) * | 2020-09-09 | 2020-12-01 | 江西丹霞生物科技股份有限公司 | Preparation process for preparing sodium copper chlorophyllin from algae of cyanophyta |
| CN114948811A (en) * | 2022-05-12 | 2022-08-30 | 南京斯拜科生物科技股份有限公司 | Natural hair dye with ginkgo polyphenol as raw material and preparation method thereof |
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Address after: 210000 building C, Shilin Industrial Park, No. 10, Wanshou Road, Jiangbei new area, Nanjing, Jiangsu Patentee after: Nanjing sbaike Biotechnology Co.,Ltd. Address before: 210000 floor 5, building C, Shilin Industrial Park, No. 10, Wanshou Road, Pukou District, Nanjing, Jiangsu Province Patentee before: SPEC-CHEM INDUSTRY Inc. |
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| PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A Method for Preparing Plant Derived Sodium Copper Chlorophyll Salt for Anti emulsification Effective date of registration: 20230419 Granted publication date: 20200414 Pledgee: Nanjing Branch of Jiangsu Bank Co.,Ltd. Pledgor: Nanjing sbaike Biotechnology Co.,Ltd. Registration number: Y2023980038503 |