CN114671754A - Method for purifying crude abscisic acid - Google Patents

Method for purifying crude abscisic acid Download PDF

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CN114671754A
CN114671754A CN202210461340.9A CN202210461340A CN114671754A CN 114671754 A CN114671754 A CN 114671754A CN 202210461340 A CN202210461340 A CN 202210461340A CN 114671754 A CN114671754 A CN 114671754A
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abscisic acid
crude
petroleum ether
purifying
filtrate
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CN114671754B (en
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肖江
周金龙
聂志奎
谌鹏飞
阙好新
聂波
廖海兵
宋志远
周圣骄
雷文
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Jiangxi New Reyphon Biochemical Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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  • Organic Chemistry (AREA)
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  • Oil, Petroleum & Natural Gas (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a method for purifying a crude abscisic acid product, which relates to the field of biochemical engineering, and is characterized in that after the crude abscisic acid product with the mass content of 70-85% is dissolved by ethyl acetate, activated carbon is added for decolorization and adsorption, and then filtration is carried out to obtain an abscisic acid solution subjected to decolorization and adsorption treatment. And slowly adding petroleum ether into the abscisic acid solution until the abscisic acid fine powder is not separated out, standing, filtering and drying. The solvent in the mother liquor can be recovered, and the recovered mother liquor can be used for preparing a preparation product. The method has the advantages of simple operation, no need of silica gel adsorption or chromatography, reduced pressure concentration, continuous application of the recovered solvent, short process flow, low cost, easy implementation and suitability for industrial production.

Description

Method for purifying crude abscisic acid
Technical Field
The invention relates to the field of biochemical engineering, in particular to a method for purifying a crude abscisic acid product.
Background
Abscisic acid is a plant growth regulator widely applied at home and abroad at present, can improve the drought resistance and salt tolerance of plants, and has extremely high value for developing and utilizing medium and low yield fields, planting forests, greening deserts and the like. Abscisic acid is an effective inhibitor for inhibiting seed germination, so that the abscisic acid can be used for seed storage and ensures the storage quality of seeds and fruits. In addition, the abscisic acid can also cause the air holes of the leaves to be quickly closed, can be used for the preservation of flowers, the adjustment of flowering phase, the promotion of rooting and the like, and has great application value in flower gardening. However, the traditional chemical synthesis method has complex steps and high cost, and due to the chiral carbon atoms in the molecular structure, the synthesized product is a mixture of natural (+) ABA and non-natural (-) ABA, and the activity of the synthesized product is low and the large-scale application in agricultural production is difficult to meet. At present, the abscisic acid is generally produced by a microbial fermentation method in industry. Therefore, the defect of a chemical synthesis method can be eliminated, and the obtained abscisic acid is (+) ABA and has the advantages of good activity, high purity and the like.
The abscisic acid which is commercially available in the market at present is obtained by microbial fermentation. However, a large amount of protein and organic impurities are generated in the microbial fermentation process, and meanwhile, the impurities are separated out together with abscisic acid along with the subsequent processing to form an abscisic acid crude product. The content of the crude abscisic acid is low (about 80 percent), the impurity content is high, the color is yellow, and the crude abscisic acid is difficult to meet the requirements of markets and farmers. The main process of the existing method for purifying the crude abscisic acid is that the crude abscisic acid is dissolved and then filtered, silica gel powder is added for adsorption or chromatography and adsorption are carried out on a chromatographic column filled with silica gel, then concentration is carried out, and finally petroleum ether is added for crystallization. The process not only needs to use a large amount of silica gel powder, but also needs to use chromatography operation, has complex operation, generates a large amount of waste materials and is not beneficial to environmental protection. Meanwhile, the poor processing capacity of chromatographic operation is not suitable for industrial mass production.
Disclosure of Invention
The invention aims to at least solve one of the technical problems in the prior art and provides a method for purifying a crude abscisic acid product.
The technical solution of the invention is as follows:
a simple and efficient method for purifying crude abscisic acid comprises the following steps:
(1): dissolving the crude abscisic acid: dissolving the abscisic acid crude product with the mass content of 70-85% by using ethyl acetate;
(2): decoloring and adsorbing: decoloring and adsorbing the dissolved solution by using activated carbon, filtering, and collecting filtrate;
(3): and (3) filtering: filtering the decolorized and adsorbed abscisic acid solution, and collecting filtrate;
(4): and (3) crystallization: adding petroleum ether into the collected filtrate, and standing until the filtrate is completely crystallized;
(5): filtering and drying: after the feed liquid is completely crystallized, filtering to obtain abscisic acid fine powder, drying, weighing, detecting and calculating the content of the abscisic acid fine powder;
(6): and (3) solvent recovery: and (4) recovering the solvent from the mother liquor filtered in the step (5), recording the volume of the recovered solvent, sampling and measuring the titer of the recovered solvent, calculating the total yield of the abscisic acid, measuring the proportion of ethyl acetate and petroleum ether of the recovered solvent, supplementing the petroleum ether according to the specified proportion, and continuing returning to the step (4) for use.
Ethyl acetate is used for dissolving in the step (1), and the dissolving proportion is that ethyl acetate and crude products (8-15) are 1 (volume to mass ratio, L/kg); the dissolving and stirring time is 5-10 min.
The active carbon is used for decolorization and adsorption in the step (2), and the mass usage of the active carbon accounts for 0.25-0.5% of the volume of the abscisic acid solution; and stirring the activated carbon when the abscisic acid solution is added, wherein the stirring time is 5-10 min, and standing the mixture after the stirring is finished, and the standing time is 20-30 min. The adding amount of the petroleum ether in the step (4) is 2-5: 1 in volume ratio to the filtrate; adding petroleum ether and stirring at the same time, wherein the stirring time is 10-30 min, and standing after stirring is finished, wherein the standing time is 30-60 min.
The drying equipment in the step (5) is a vacuum drying oven or a double-cone dryer;
and (5) controlling the solvent recovery temperature in the step (6) to be 40-50 ℃ and controlling the vacuum degree to be-0.07 to-0.10 MPa. The concentration device is a rotary evaporator or a vacuum concentration evaporator. Meanwhile, the method for calculating the total yield of the abscisic acid comprises the following steps:
yield ═ yield (crystal powder mass × content + residual mother liquor titer (μ g/ml) × mother liquor volume (ml) × 10-6) /(crude mass x content).
The invention has the beneficial effects that: the method has simple and convenient operation and easy implementation, only needs to use petroleum ether for crystallization, does not need to use a large amount of complicated operations such as silica gel adsorption or chromatography, has high treatment capacity, does not generate a large amount of waste, and is environment-friendly. The recovered solvent can be used continuously. The mother liquor after crystallization and separation can be made into preparation products. The method for purifying the crude abscisic acid has the advantages of simple process flow, high processing capacity and suitability for industrial production, the content of the obtained abscisic acid crystal powder reaches more than 90 percent, and the extraction yield reaches more than 80 percent.
Drawings
FIG. 1 is a process flow diagram of the present invention.
Detailed Description
The technical solution of the present invention is further explained by the following specific examples.
Example 1:
dissolution of crude abscisic acid
10.02g of crude abscisic acid with the mass content of 83.3 percent is dissolved in 120mL of ethyl acetate, the mixture is stirred for 5min, and the next operation is carried out after the crude product is completely dissolved.
2) Decolorization and adsorption
Adding 0.25% active carbon (0.30 g) into the dissolved solution, stirring for 5min, and standing for 20 min.
3) Filtration
And after the decoloring and adsorption processes are finished, carrying out suction filtration on the dissolved solution to obtain 110mL of clear and transparent filtrate with the titer of 70164 mu g/mL, carrying out environment-friendly treatment on filter residues, and carrying out next treatment on the filtrate.
4) Crystallization of
And slowly adding 330mL of petroleum ether with the volume ratio of 3:1 to the filtrate in the last step while stirring, slowly stirring for 10min after the petroleum ether is added, and standing for 30min until crystallization is complete.
5) Filtering and drying
And after the crystallization is completed, filtering, taking out the crystal powder after the filtration is completed, and drying in a vacuum drying oven at the drying temperature of 50 ℃ and the vacuum degree of-0.09 MPa. After the drying is finished, the crystal powder is weighed to obtain 6.78g of crystal powder with the content of 94.7 percent and 410mL of mother liquor with the titer of 2352 mu g/mL.
6) Solvent recovery
And concentrating 410mL of mother liquor in vacuum to recover the solvent, wherein the recovery temperature is 35 ℃, the vacuum degree is-0.095 MPa, and the titer of the mother liquor is 5724 mu g/mL after the mother liquor is concentrated to 122 mL. Meanwhile, 267mL of recovered solvent is obtained, and the proportion of the recovered solvent is detected as petroleum ether: ethyl acetate 4.2: 1. Thus, the yield was (6.78 × 94.7% +5724 × 122 × 10)-6)/(10.02×83.3％)＝85.29％。
Example 2:
dissolution of crude abscisic acid
Taking 10.14g of crude abscisic acid with the mass content of 77.35%, dissolving in 150mL of ethyl acetate, stirring for 8min, and carrying out the next operation after the crude abscisic acid is completely dissolved.
2) Decolorization and adsorption
Adding 0.35% active carbon (0.52 g) into the dissolved solution, stirring for 7min, and standing for 25 min.
3) Filtration
After the decoloring and adsorption processes are finished, carrying out suction filtration on the abscisic acid solution to obtain 140mL of clear and transparent filtrate with the titer of 55257 mu g/mL, carrying out environment-friendly treatment on filter residues, and carrying out next-step treatment on the filtrate.
4) Crystallization of
Slowly adding 560mL petroleum ether into the filtrate in the previous step, stirring while adding, slowly stirring for 15min after adding petroleum ether, standing for 40min, and crystallizing completely.
5) Filtering and drying
And after the crystallization is completed, filtering, taking out the crystal powder after the filtration is completed, and drying in a vacuum drying oven at the drying temperature of 55 ℃ and the vacuum degree of-0.08 MPa. After the drying is finished, the crystal powder is weighed to obtain crystal powder with the mass of 6.39g, the content of 93.8 percent, 635mL of mother liquor and the titer of 1630 mu g/mL.
6) Solvent recovery
And carrying out vacuum concentration on 635mL of mother liquor to recover the solvent, wherein the recovery temperature is 40 ℃, the vacuum degree is-0.085 MPa, and the mother liquor is 4916 mu g/mL after the mother liquor is concentrated to the volume of 156 mL. Meanwhile, 462mL of recovered solvent is obtained, and the proportion of the recovered solvent is detected as petroleum ether: ethyl acetate 6.7: 1. Thus, the yield was (6.39 × 93.8% +4916 × 156 × 10)-6)/(10.14×77.35％)＝86.20％。
Example 3:
dissolution of crude abscisic acid
Dissolving 10.28g of crude abscisic acid with the mass content of 70.89% in 90mL of ethyl acetate, stirring for 10min, and filtering after the crude abscisic acid is completely dissolved.
2) Decolorization and adsorption
Adding 0.5% active carbon (0.45 g) into the dissolved solution, stirring for 10min, and standing for 30 min.
3) Filtration
After the decoloring and adsorption processes are finished, carrying out suction filtration on the abscisic acid solution to obtain 82mL of clear and transparent filtrate with the titer of 87647 mu g/mL, carrying out environment-friendly treatment on filter residues, and carrying out next-step treatment on the filtrate.
4) Crystallization of
The recovered solvent in example 3, which is 410mL of the recovered solvent (petroleum ether: ethyl acetate 6.7:1) in a volume ratio to the filtrate of 5:1, was slowly added to the filtrate in the previous step while stirring, and after the addition of petroleum ether was completed, the mixture was slowly stirred for 30min, and then allowed to stand for 50min until crystallization was completed.
5) Filtering and drying
And filtering after the crystallization is completed, taking out the crystallized powder after the filtration is finished, and drying in a vacuum drying oven at the drying temperature of 60 ℃ and the vacuum degree of-0.075 MPa. After the completion of drying, the crystal powder was weighed to obtain 6.62g of crystal powder with a content of 93.1%, 424mL of mother liquor with a titer of 1230. mu.g/mL.
6) Solvent recovery and mother liquor concentration crystallization
Carrying out vacuum concentration on 424mL of mother liquor to recover the solvent, wherein the recovery temperature is 45 ℃, and after the vacuum degree is minus 0.080MPa, the concentration is carried out to reach the volume of 132mL, the titer of the mother liquor is 3450ug/mL, meanwhile, 276mL of the recovered solvent is obtained, and the detected proportion of the recovered solvent is petroleum ether: ethyl acetate 3.4: 1. Thus, the yield was (6.42 × 93.1% +3450 × 132 × 10)-6)/(10.28×70.89％)＝88.27％。
Example 4: example of industrialization
1) Dissolution of crude abscisic acid
100.42kg of crude abscisic acid product with the mass content of 72.37 percent is taken to be dissolved in 100L of ethyl acetate in a dissolving tank, the stirring is started for 10min, and the filtration is carried out after the crude product is completely dissolved.
2) Decolorization and adsorption
Adding 0.4% active carbon 400g into the dissolved solution, stirring for 10min, and standing for 30 min.
3) Filtration
After the decoloring and adsorption processes are finished, the abscisic acid solution is pressed into a crystallizing tank by using nitrogen, the abscisic acid solution can pass through a filter with a filter element to be filtered in the process, and finally, 96L of clear and transparent filtrate with the titer of 7343 mu g/mL is obtained, the filter residue is subjected to environment-friendly treatment, and the filtrate enters the next step of treatment.
4) Crystallization of
Opening a valve of a head tank of a petroleum ether storage tank, slowly adding 240L petroleum ether which is the petroleum ether with the volume ratio of 2.5:1 to the filtrate in the previous step, starting stirring while adding, slowly stirring for 30min after the petroleum ether is added, standing for 60min, and completely crystallizing.
5) Filtering and drying
And after the crystallization is completed, carrying out filtration operation, wherein the filtration is centrifugal filtration, and after the filtration is completed, taking out the crystal powder, and placing the crystal powder in a double-cone dryer for drying, wherein the drying temperature is 60 ℃, and the vacuum degree is-0.075 MPa. After the completion of drying, the crystal powder was weighed to obtain 64.7kg in mass, 92.4% in content, 317L in mother liquor, and 3256. mu.g/mL in titer.
6) Solvent recovery and mother liquor concentration crystallization:
putting 317L of mother liquor into a solvent recovery tank, recovering the solvent at 50 ℃ and under the vacuum degree of-0.075 MPa, and recovering to the volume of 113L to obtain the mother liquor with the titer of 5431 mu g/ml. The volume of the recovered solvent was 187L, and thus the yield was (64.7X 92.4% + 5431X 113X 10)-6)/(100.42×72.37%)＝83.11％。
Comparative example 1
1) Dissolution of crude abscisic acid
And (3) dissolving 10.45g of abscisic acid crude product with the mass content of 75.42% in 150mL of ethyl acetate, stirring for 10min, and carrying out the next operation after the crude product is completely dissolved.
2) Filtration
And (3) carrying out suction filtration on the abscisic acid solution to obtain 140mL of clear and transparent filtrate, wherein the titer is 53437 mu g/mL, carrying out environment-friendly treatment on filter residues, and carrying out next-step treatment on the filtrate.
3) Chromatographic column packing column
Silica gel powder is filled into the chromatographic column, the ratio of the mass of the silica gel powder to the volume of chromatographic feed liquid is 3:1(1L of feed liquid corresponds to 3kg of silica gel powder), and the silica gel powder is compacted for chromatographic operation.
4) Adding petroleum ether for chromatography
Adding petroleum ether into the filtrate obtained in the step 2) according to the volume ratio of 1:1, namely adding 140mL of petroleum ether, stirring for 5min, carrying out chromatography operation, collecting chromatography liquid, after the chromatography is finished, using a mixed solvent of ethyl acetate and petroleum ether, namely 28mL of washing column, wherein the volume fraction of the ethyl acetate and the petroleum ether is 20%, and the volume fraction of the ethyl acetate and the petroleum ether is 1:1, and collecting the chromatography liquid and the washing liquid. And (4) carrying out environment-friendly treatment on the waste silica gel.
5) Concentrating the chromatography liquid
And (3) concentrating the chromatographic solution in the last step in vacuum, wherein the volume of the concentrated solution is one fifth of that of the chromatographic solution and washing liquor (the titer is controlled to be 14 ten thousand mu g/mL), and thus obtaining 61mL of chromatographic concentrated solution.
6) Crystallization of chromatographic concentrated solution
And slowly adding petroleum ether into the filtrate in the last step, wherein the volume ratio of the petroleum ether to the chromatographic concentrated solution is 1:1, namely adding 61mL of petroleum ether while stirring, slowly stirring for 10min after the petroleum ether is added, and standing for 30min until crystallization is complete.
7) Filtering and drying
And after the crystallization is completed, filtering, taking out the crystallized powder after the filtration is completed, and drying in a vacuum drying oven at the drying temperature of 60 ℃ and the vacuum degree of-0.075 MPa. After the completion of drying, the crystal powder was weighed to obtain 5.39g of crystal powder with a content of 94.1% and 112mL of mother liquor with a titer of 7654. mu.g/mL.
Thus, the yield was (5.39 × 94.1% +7654 × 112 × 10)-6)/(10.45×75.42％)＝75.23％
Comparative analysis of examples with comparative example 1:
from the above, it can be seen that: the process of purifying abscisic acid in examples 1-4 is far less than that in comparative example 1, the content of abscisic acid refined powder obtained in the examples is 92.4-94.7%, the content of abscisic acid refined powder obtained in comparative example 1 is 94.1%, although the purity is not obvious, the yield of abscisic acid is far higher than that in comparative example 1, and the usage amount of decolorization and adsorption only by using activated carbon in comparative example 1 is only 0.25-0.50%. In contrast, in comparative example 1, silica gel chromatography and adsorption were used in a mass to volume ratio of 3:1, the use level is very large, a large amount of waste is generated, and the waste is required to be treated as hazardous waste. The simple and efficient method for purifying the crude abscisic acid disclosed by the invention is simple and reasonable in process and more environment-friendly.
From the above, it can be seen that: the solvents in the examples 1 to 4 can be recycled, while the petroleum ether and ethyl acetate in the solvent concentrated from the chromatographic solution in the comparative example need to be further separated for reuse, but the separation step is difficult, so the solvent in the comparative example 1 cannot be directly recycled, and the complicated operations such as chromatography, reduced pressure concentration and the like are not needed in the examples 1 to 4. The total yield of abscisic acid in the examples 1-4 is 83.11-88.27% (wherein the total yield of abscisic acid in the example 4 is an industrial example, which is not obviously different from other examples, and is higher than that in the comparative example 1, which shows that the invention has no amplification effect and is beneficial to industrial application), and the total yield of abscisic acid in the comparative example 1 is 75.23%. The overall yield in the examples is much higher than in comparative example 1. The simple and efficient method for purifying the crude abscisic acid disclosed by the invention has higher efficiency and can obviously reduce the cost.
The specific embodiments described herein are merely illustrative of the invention. Various modifications or additions may be made or substituted in a similar manner to the described embodiments by those skilled in the art without departing from the scope of the invention or exceeding the ambit as defined in the appending claims
The above additional technical features can be freely combined and used in superposition by those skilled in the art without conflict.
The above description is only a preferred embodiment of the present invention, and the technical solutions that achieve the objects of the present invention by substantially the same means are within the protection scope of the present invention.

Claims (7)

1. The method for purifying the crude abscisic acid is characterized by comprising the following steps of:
(1) dissolving the abscisic acid crude product by using ethyl acetate to obtain abscisic acid solution;
(2) decoloring the abscisic acid solution by using active carbon and removing impurities by adsorption;
(3) filtering the decolorized and adsorbed abscisic acid crude product, and collecting filtrate;
(4) adding petroleum ether into the collected filtrate, and standing until the filtrate is completely crystallized;
(5) after the filtrate is completely crystallized, filtering to obtain abscisic acid fine powder, and drying the abscisic acid fine powder;
(6) and (4) recovering the solvent from the mother liquor filtered in the step (5), measuring the proportion of ethyl acetate and petroleum ether of the recovered solvent, supplementing the petroleum ether according to a specified proportion, and continuing returning to the step (4) for use.
2. The method for purifying the crude abscisic acid as claimed in claim 1, wherein the volume-to-mass ratio of the ethyl acetate to the crude abscisic acid in the step (1) is 8-15: 1; the dissolving and stirring time is 5-10 min.
3. The method for purifying the crude abscisic acid as claimed in claim 1, wherein the mass usage of the activated carbon in the step (2) accounts for 0.25-0.5% of the volume of the abscisic acid solution; stirring the activated carbon when the abscisic acid solution is added, wherein the stirring time is 5-10 min, and standing the activated carbon after the stirring is finished for 20-30 min.
4. The method for purifying the crude abscisic acid as claimed in claim 1, wherein the titer of the filtrate in the step (3) is 50000-100000 μ g/mL.
5. The method for purifying the crude abscisic acid as claimed in claim 1, wherein in the crystallization process in the step (4), the volume ratio of the addition amount of petroleum ether to the filtrate is (2-5): 1; stirring while adding petroleum ether, wherein the stirring time is 10-30 min, and standing for 30-60 min after stirring.
6. The method for purifying the crude abscisic acid as claimed in claim 1, wherein the drying in step (5) is vacuum drying at 50-60 ℃ and vacuum degree of-0.07-0.10 MPa.
7. The method for purifying the crude abscisic acid as claimed in claim 1, wherein the solvent recovery in step (6) is performed by vacuum concentration at 30-50 ℃ under a vacuum degree of-0.07 to-0.10 MPa.
CN202210461340.9A 2022-04-28 2022-04-28 Method for purifying crude abscisic acid Active CN114671754B (en)

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CN116730831A (en) * 2023-07-03 2023-09-12 江西新瑞丰生化股份有限公司 Extraction method of abscisic acid mother liquor
CN116730831B (en) * 2023-07-03 2024-04-12 江西新瑞丰生化股份有限公司 Extraction method of abscisic acid mother liquor

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