CN110734359B - Extraction and purification method of cannabidiol - Google Patents
Extraction and purification method of cannabidiol Download PDFInfo
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- CN110734359B CN110734359B CN201910926970.7A CN201910926970A CN110734359B CN 110734359 B CN110734359 B CN 110734359B CN 201910926970 A CN201910926970 A CN 201910926970A CN 110734359 B CN110734359 B CN 110734359B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/82—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by solid-liquid treatment; by chemisorption
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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Abstract
The invention discloses a method for extracting and purifying cannabidiol, which comprises the steps of drying cannabis flowers, leaves or seed coats, crushing, extracting by a supercritical argon extraction method, performing primary separation by a molecular distillation method, and finally performing separation and purification by an argon supercritical fluid chromatographic separation method to obtain high-purity cannabidiol. The purification and extraction method of the invention greatly improves the extraction yield of cannabidiol, obviously improves the purity of the final product, the organic solvent residue and the pesticide residue compared with the existing product, and provides guarantee for the safety of the product applied to cosmetics, health-care food and medicines.
Description
Technical Field
The invention relates to a method for extracting and purifying cannabidiol, belonging to the technical field of extraction of medicinal components.
Background
Cannabis sativa L, also known as hemp, sisal, hemp etc., is an annual herb plant of the genus Cannabis of the family Moraceae. Because the Tetrahydrocannabinol (THC) has mental and physiological activity after being sucked or orally taken, the THC can excite, cause illusion and damage nervous systems of people and has certain addiction, therefore, the industrial hemp which is allowed to be planted in China is the industrial hemp, and the content of the chemical component of the THC is required to be lower than 0.3 percent; cannabidiol (CBD) is a non-psychoactive substance in marijuana, has good neuroprotective effect, anti-inflammatory, anti-oxidation effect, anti-tumor effect, anti-liver injury effect, immunoregulation effect and the like, is widely used in the fields of medicines, health products, functional beverages, cosmetics and the like, and the content of cannabidiol which is a main component in marijuana flowers and marijuana leaves is higher than 3 percent in industrial marijuana seeds selected by us.
At present, the extraction process of cannabidiol mainly adopts the modes of carbon dioxide supercritical extraction, nitrogen supercritical extraction, organic solvent extraction and the like for extraction, and combines the operations of heating or ultrasound and the like for mixed extraction. The extraction process in the prior art can not completely remove heavy metal residues, pesticide residues, impurities and the like, so that potential safety hazards exist in the final product, certain negative effects are caused on the purity of the product, the purity can only reach 98% at most, substances with higher purity and lower impurities cannot be obtained, chemical reactions between cannabidiol and other components in the extraction process are easily caused, the extraction yield is reduced, and the practical application field is greatly limited.
It can be seen that the prior art only takes the extraction cost and purity as the quality basis of the final product as the extraction purpose, and does not take the removal of heavy metal residues, pesticide residues, organic solvent residues, impurities introduced in the extraction process and the like as important components of the process, so that the purity of the final product is adversely affected, and unpredictable adverse reactions are generated on the safety of the application of the cannabidiol in the fields of medicines, health products, cosmetics and the like. The safety of the application in human body is put to the same position as the practicability in the modern society, and even higher, so that the development of a cannabidiol extraction and purification method with high safety, high purity and high yield is urgently needed.
Disclosure of Invention
In order to solve the defects in the prior art, the invention provides a method for extracting and purifying cannabidiol, which comprises the steps of drying cannabis flowers, leaves or seed coats, crushing, extracting by adopting a supercritical argon extraction method, performing primary separation by adopting a molecular distillation method, and finally performing separation and purification by adopting an argon supercritical fluid chromatographic separation method to obtain the high-purity cannabidiol. The purification and extraction method of the invention greatly improves the extraction yield of cannabidiol, obviously improves the purity of the final product, the organic solvent residue and the pesticide residue compared with the existing product, and provides guarantee for the safety of the product applied to cosmetics, health-care food and medicines.
Specifically, the invention provides a cannabidiol extraction and purification method, which comprises the following steps:
(1) drying cannabis sativa flowers, leaves or seed coats with a hot air circulating air box at 60-150 ℃ until the water content is not higher than 6%;
(2) crushing dried cannabis sativa flowers, leaves or seed coats to particles of 20-100 meshes;
(3) extracting crushed hemp flowers, leaves or seed coats by using a supercritical argon extraction method at the extraction temperature of-70-40 ℃, and using a staged pressure control mode to enable the argon pressure to reach a supercritical state of 5-50 MPa, wherein the extraction time is 0.5-5 hours, the resolution temperature is-70-20 ℃, and the resolution pressure is 1-20 MPa, so as to obtain a hemp extract;
(4) distilling the hemp extract obtained in the step (3) for 2-5 times by adopting a molecular distillation method, wherein the distillation temperature is 115-220 ℃, and the vacuum degree is 0.5-20 Pa, so as to obtain crude hemp oil;
(5) dissolving the crude hemp oil obtained in the step (4) with ethanol or methanol with the weight of 6-20 times, and separating and purifying by adopting an argon supercritical fluid chromatographic separation method, wherein the chromatographic conditions are as follows: the column temperature is-70-20 ℃, the pressure is 30-70 MPa, the flow rate is 10-50 ml/min, the chromatographic column filler is octadecylsilane chemically bonded silica, macroporous resin, polystyrene-divinylbenzene, polymethyl propionate, graphitized carbon or alumina, and supercritical argon is used as a mobile phase;
(6) and (5) collecting the cannabidiol stream section obtained in the step (5) to obtain a cannabidiol pure product.
Preferably, the drying temperature in the step (1) is 120 ℃.
Preferably, the pulverization degree in the step (2) is 100 meshes.
Preferably, in the step (3), the extraction temperature is 20 ℃, the argon pressure is 30MPa, the extraction time is 5 hours, the analysis temperature is 20 ℃, and the analysis pressure is 10 MPa.
Preferably, the number of distillations in the step (4) is 5.
Preferably, the distillation temperature in the step (4) is 180 ℃.
Preferably, the vacuum degree in the step (4) is 10 Pa.
Preferably, the solvent used for dissolution in step (5) is 12 times the weight of ethanol in the crude hemp oil.
Preferably, the chromatographic conditions in the step (5) are that the column temperature is 4 ℃, the pressure is 50MPa and the flow rate is 20 ml/min.
Preferably, the chromatography column packing in step (5) is alumina.
Compared with the prior art, the invention has the beneficial effects that:
1. the hot air circulation air box drying method and the drying conditions adopted by the invention have high drying speed, can ensure that the effective components in the hemp flowers, the hemp leaves or the hemp seed coats are not lost, and improve the product yield.
2. The supercritical argon extraction method and the extraction conditions adopted by the invention adopt argon for supercritical extraction for the first time, and have the advantages that: compared with the carbon dioxide supercritical fluid commonly used in the prior art, the argon supercritical fluid is easier to obtain and has no residue; compared with the carbon dioxide supercritical fluid commonly used in the prior art, the argon supercritical fluid has narrower dissolution spectrum, weaker dissolution capability on enzyme, fatty acid, pigment, colloidal substance and the like in the hemp, and weaker dissolution capability on pesticide residue and heavy metal residue, so that the argon supercritical fluid has higher selectivity on extracting a target object, is beneficial to later-stage purification, and can remove the heavy metal and the pesticide residue in the hemp; and argon belongs to inert gas, can protect each component in the extraction and purification process, can prevent cannabidiol from reacting with other substances in the extraction process, and improves the product yield.
3. The molecular distillation method adopted by the invention can purify the hemp oil due to the difference of molecular free paths of various components and impurity components in the hemp oil, can separate the hemp oil according to categories, has simple process operation and high efficiency, can remove most enzymes, fatty acid, chlorophyll, colloidal substances, heavy metal, pesticide residue and the like, and can reduce the viscosity, so that the purity of the obtained crude hemp oil (containing tetrahydrocannabinol) reaches more than 95 percent, and the content of cannabidiol reaches more than 80 percent.
4. The argon supercritical fluid chromatographic separation method adopted by the invention has high separation efficiency and high selectivity, the purity of the sample obtained by separation is high, the organic solvent removal efficiency is high, the purity of the obtained cannabidiol is more than 99.8 percent, the overall cannabidiol yield is more than 94.5 percent, and the standard is obviously higher than that of the product prepared by the prior art.
5. The method adopts a small amount of solvent ethanol or methanol when adopting an argon supercritical fluid chromatographic separation method, has the function of assisting removal in the argon volatilization process, and cannot cause solvent residue.
Detailed Description
The invention will be further described with reference to specific embodiments, and the advantages and features of the invention will become apparent as the description proceeds. These examples are illustrative only and do not limit the scope of the present invention in any way. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention, and that such changes and modifications may be made without departing from the spirit and scope of the invention.
Example 1
(1) Drying Cannabis sativa flower, leaf or seed coat with hot air circulation blower at 120 deg.C until water content is not higher than 6%;
(2) pulverizing dried flos Cannabis, leaf or seed coat into 100 mesh powder;
(3) extracting pulverized flos Cannabis, leaves or seed coats by supercritical argon extraction at 20 deg.C under 30MPa for 5 hr at 20 deg.C under 10MPa to obtain extract;
(4) distilling the hemp extract obtained in the step (3) for 5 times by adopting a molecular distillation method, wherein the distillation temperature is 180 ℃, and the vacuum degree is 10Pa, so as to obtain crude hemp oil;
(5) dissolving the crude hemp oil obtained in the step (4) by using 12 times of ethanol or methanol, and separating and purifying by adopting an argon supercritical fluid chromatographic separation method, wherein the chromatographic conditions are as follows: the column temperature is 4 ℃, the pressure is 50MPa, the flow rate is 20ml/min, the chromatographic column packing adopts alumina, and supercritical argon is used as a mobile phase;
(6) and (5) collecting the cannabidiol stream section obtained in the step (5) to obtain a cannabidiol pure product.
Example 2
(1) Drying Cannabis sativa flower, leaf or seed coat with hot air circulation blower at 60 deg.C until water content is not higher than 6%;
(2) pulverizing dried flos Cannabis, leaf or seed coat into 20 mesh powder;
(3) extracting pulverized flos Cannabis, leaves or seed coat by supercritical argon extraction at-70 deg.C for 0.5 hr under-70 deg.C and 1MPa under-70 deg.C by stage pressure control to obtain extract;
(4) distilling the hemp extract obtained in the step (3) for 2 times by adopting a molecular distillation method, wherein the distillation temperature is 115 ℃, and the vacuum degree is 0.5Pa, so as to obtain crude hemp oil;
(5) dissolving the crude hemp oil obtained in the step (4) by using ethanol or methanol with the weight being 6 times that of the crude hemp oil, and separating and purifying by adopting an argon supercritical fluid chromatographic separation method, wherein the chromatographic conditions are as follows: the column temperature is-70 ℃, the pressure is 30MPa, the flow rate is 10ml/min, the chromatographic column filler adopts graphitized carbon, and supercritical argon is used as a mobile phase;
(6) and (5) collecting the cannabidiol stream section obtained in the step (5) to obtain a cannabidiol pure product.
Example 3
(1) Drying cannabis flos, leaf or seed coat with hot air circulation bellows at 150 deg.C until water content is not higher than 6%;
(2) pulverizing dried flos Cannabis, leaf or seed coat into 100 mesh powder;
(3) extracting pulverized flos Cannabis, leaves or seed coat by supercritical argon extraction at 40 deg.C under 50MPa for 5 hr at 20 deg.C under 20MPa to obtain extract;
(4) distilling the hemp extract obtained in the step (3) for 5 times by adopting a molecular distillation method, wherein the distillation temperature is 220 ℃, and the vacuum degree is 20Pa, so as to obtain crude hemp oil;
(5) dissolving the crude hemp oil obtained in the step (4) with 20 times of ethanol or methanol, and separating and purifying by an argon supercritical fluid chromatography, wherein the chromatography conditions are as follows: the column temperature is 20 ℃, the pressure is 70MPa, the flow rate is 50ml/min, the chromatographic column filler adopts polystyrene-divinylbenzene, and supercritical argon is used as a mobile phase;
(6) and (5) collecting the cannabidiol stream section obtained in the step (5) to obtain a cannabidiol pure product.
Examples of the experiments
The organic solvent extraction method is simple to operate, but most of pesticides are easily soluble in organic solvents, the pesticide residue in the later period is higher, the safety of product application cannot be estimated, and unpredictable decarboxylation, salification with residual heavy metals, reaction with residual pesticides and generation of toxic substances and the like which are difficult to remove are easy to occur in the extraction process due to the fact that an inert substance environment does not exist.
Compared with the carbon dioxide supercritical extraction method, the argon supercritical fluid has narrower dissolution spectrum, weaker dissolving capacity on enzymes, fatty acids, pigments, colloidal substances and the like in the hemp, weaker dissolving capacity on pesticide residues and heavy metal residues, and easier acquisition than the carbon dioxide supercritical fluid.
Compared with a nitrogen supercritical extraction method, the argon has better inertia, the extraction conditions required by the argon supercritical extraction method are lower than that of the nitrogen supercritical extraction method, the argon supercritical extraction method is more suitable for industrial production, the dissolving capacity of the argon supercritical extraction method is weaker than that of a nitrogen supercritical fluid, the extraction amount of non-main components can be reduced in the first-step extraction process, the premise of higher quality is provided for the next separation and purification steps, and the premise is provided for improving the yield and the purity of the finally prepared product.
In addition, only a small amount of organic solvent ethanol or methanol is used before molecular distillation in the invention to facilitate molecular distillation operation, while in the prior art, besides the extraction step, a large amount of organic solvent is also needed, which causes drug residue treatment, solvent residue in later period and higher production cost.
Comparative experiments on products prepared by the present invention and several main extraction methods in the prior art are now as follows:
1. based on the steps (1) to (3) of example 1, the hemp extracts obtained by the different extraction methods were compared, and the extraction methods were different only in that the supercritical fluid or the organic solvent in step (3) was replaced, and the results are shown in table 1.
TABLE 1 comparison of the results of the different extraction processes for cannabis extracts
Through the comparison of the experiments, the following steps are shown: for important impurity components (such as fatty acids, colloidal substances, pesticide residues, heavy metal substances, pigments and the like) in the extract, all indexes of the organic solvent extraction method are obviously higher than those of the supercritical extraction method, and all indexes of the argon supercritical extraction method are obviously lower than those of the carbon dioxide supercritical extraction method and the nitrogen supercritical extraction method.
2. Based on the extraction and purification method of example 1, the cannabidiol products obtained by different extraction methods are compared, and the extraction methods are different only in that the supercritical fluid or the organic solvent in the step (3) is replaced. The results are shown in Table 2.
TABLE 2 comparison of cannabidiol obtained by different extraction methods
From the above experimental results, it can be seen that: the purity of the cannabidiol finally prepared by adopting the argon supercritical fluid extraction method combined with molecular distillation and argon supercritical fluid chromatography is obviously higher than that of the cannabidiol prepared by other extraction methods, ethanol residues cannot be detected, other pesticide residues cannot be detected, saturated fatty acid cannot be detected, and the yield is also obviously higher than that of other extraction methods. The final solvent residue of other extraction methods is high in variety and amount and more in impurities, and finally, in order to remove the impurities, the process steps are increased, so that the yield of the final product is reduced.
In conclusion, the argon supercritical fluid extraction method is combined with the molecular distillation method and the argon supercritical fluid chromatography to prepare the cannabidiol, the inspection conditions of impurities such as purity, organic solvent residue, pesticide residue, heavy metals and the like of the obtained product are obviously lower than those of other methods in the prior art, the yield is highest, the method is suitable for large-scale production, and the obtained product is safe to apply and can be used for production of cosmetics, health-care foods and medicines. The extraction and purification method of the invention improves the extraction and purification of cannabidiol to a new height, and is an epoch-making progress of the cannabis industry.
Claims (9)
1. The extraction and purification method of cannabidiol is characterized by comprising the following steps:
(1) drying cannabis sativa flowers, leaves or seed coats with a hot air circulating air box at 60-150 ℃ until the water content is not higher than 6%;
(2) crushing dried cannabis sativa flowers, leaves or seed coats to particles of 20-100 meshes;
(3) extracting pulverized flos Cannabis, leaves or seed coat by supercritical argon extraction at 20 deg.C under 30MPa for 5 hr, at 20 deg.C under 10MPa to obtain extract;
(4) distilling the hemp extract obtained in the step (3) for 2-5 times by adopting a molecular distillation method, wherein the distillation temperature is 115-220 ℃, and the vacuum degree is 0.5-20 Pa, so as to obtain crude hemp oil;
(5) dissolving the crude hemp oil obtained in the step (4) with ethanol or methanol with the weight of 6-20 times, and separating and purifying by adopting an argon supercritical fluid chromatographic separation method, wherein the chromatographic conditions are as follows: the column temperature is-70-20 ℃, the pressure is 30-70 MPa, the flow rate is 10-50 ml/min, the chromatographic column filler is octadecylsilane chemically bonded silica, macroporous resin, polystyrene-divinylbenzene, polymethyl propionate, graphitized carbon or alumina, and supercritical argon is used as a mobile phase;
(6) and (5) collecting the cannabidiol stream section obtained in the step (5) to obtain a cannabidiol pure product.
2. The process for the extraction and purification of cannabidiol as claimed in claim 1, wherein the drying temperature in step (1) is 120 ℃.
3. The method for extracting and purifying cannabidiol as claimed in claim 1, wherein the pulverization degree in the step (2) is 100 mesh.
4. The process for extracting and purifying cannabidiol as claimed in claim 1, wherein the number of distillation times in step (4) is 5.
5. The process for the extraction and purification of cannabidiol as claimed in claim 1, wherein the distillation temperature in step (4) is 180 ℃.
6. The method for extracting and purifying cannabidiol as claimed in claim 1, wherein the vacuum in step (4) is 10 Pa.
7. The method for extracting and purifying cannabidiol as claimed in claim 1, wherein the solvent used for dissolving in step (5) is 12 times the weight of ethanol in crude cannabis oil.
8. The method for extracting and purifying cannabidiol as claimed in claim 1, wherein the chromatographic conditions in step (5) are column temperature 4 ℃, pressure 50MPa, and flow rate 20 ml/min.
9. The process for extracting and purifying cannabidiol as claimed in claim 1, wherein the packing material of the chromatographic column in step (5) is alumina.
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| CN111099970A (en) * | 2019-12-23 | 2020-05-05 | 清馨(北京)科技有限公司 | Method for industrially extracting cannabidiol from industrial cannabis sativa |
| CN111253221B (en) * | 2020-02-21 | 2021-09-24 | 南京大学 | Method for separating and purifying cannabidiol |
| CN112939742B (en) * | 2021-04-14 | 2023-07-28 | 龙麻(上海)医药研发有限责任公司 | Extraction and purification method of cannabinoid |
| CN115490574A (en) * | 2021-06-17 | 2022-12-20 | 北京创新通恒科技有限公司 | Method for purifying high-purity cannabidiol from cannabis extract |
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