CN112210442A - Extraction method of hemp volatile oil and cannabidiol - Google Patents
Extraction method of hemp volatile oil and cannabidiol Download PDFInfo
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- CN112210442A CN112210442A CN202011147805.0A CN202011147805A CN112210442A CN 112210442 A CN112210442 A CN 112210442A CN 202011147805 A CN202011147805 A CN 202011147805A CN 112210442 A CN112210442 A CN 112210442A
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/02—Recovery or refining of essential oils from raw materials
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/02—Recovery or refining of essential oils from raw materials
- C11B9/027—Recovery of volatiles by distillation or stripping
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a method for extracting cannabis volatile oil and cannabidiol, belonging to the technical field of extraction of plant active ingredients. The extraction method provided by the invention comprises the following steps: drying and crushing the hemp flowers and leaves in sequence to obtain hemp flower and leaf powder; the drying temperature is 40-150 ℃, and the drying time is 2-24 hours; performing steam distillation on the hemp flower and leaf powder to obtain hemp volatile oil and herb residue; sequentially carrying out alcohol extraction, membrane separation, first concentration, column chromatography and second concentration on the medicine residues to obtain a cannabidiol crude product; and sequentially dissolving, recrystallizing and drying the cannabidiol crude product to obtain the cannabidiol. The preparation method provided by the invention can obtain the hemp volatile oil while extracting the cannabidiol, thereby greatly improving the utilization efficiency of the hemp flowers and leaves.
Description
Technical Field
The invention relates to the technical field of extraction of effective plant ingredients, in particular to a method for extracting cannabis volatile oil and cannabidiol.
Background
Cannabis sativa (Cannabis sativaL.) is an annual herbaceous plant, and is known for its pharmacological effects and social impact. In 1988, the united nations issued the convention of banning illegal transport of narcotics and psychopharmaceuticals in the united nations, and the use and planting of cannabis in the convention had a clear regulation, and when the Tetrahydrocannabinol (THC) content in cannabis plants was below 0.3%, the variety of cannabis judged to be useful for industrial use was industrial cannabis, which allowed large-scale mass planting and industrial utilization, i.e., industrial cannabis with a tetrahydrocannabinol content of below 0.3%.
Cannabidiol (CBD) is from a flower and leaf dry matter extract of industrial cannabis sativa, and pharmacological activity studies show that the Cannabidiol has good inhibitory effect on acute pain, neuropathic pain, chronic pain, pain caused by HIV and the like, and has good treatment effect on epilepsy treatment, anticancer effect, anxiety resistance, emesis alleviation of chemotherapy of cancer patients, insomnia resistance and the like. Because of the natural activity and medicinal value of cannabidiol, CBD extracted from cannabis leaves has wide market prospect.
In the prior art, hemp leaves are generally directly thrown away or used as feed after cannabinoids such as CBD and the like are extracted, so that the hemp leaf raw material is wasted. Therefore, there is a need to develop a method for improving the utilization efficiency of hemp flowers and leaves in the process of extracting CBD.
Disclosure of Invention
In view of the above, the present invention aims to provide a method for extracting cannabis volatile oil and cannabidiol. The preparation method provided by the invention can extract CBD and obtain hemp volatile oil at the same time, thereby greatly improving the utilization efficiency of hemp flowers and leaves.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides a method for extracting cannabis volatile oil and cannabidiol, which comprises the following steps:
drying and crushing hemp flowers and leaves in sequence to obtain hemp flower and leaf powder, wherein the drying temperature is 40-150 ℃, and the drying time is 2-24 hours;
performing steam distillation on the hemp flower and leaf powder to obtain hemp volatile oil and herb residue;
sequentially carrying out alcohol extraction, membrane separation, first concentration, column chromatography and second concentration on the medicine residues to obtain a cannabidiol crude product;
and sequentially dissolving, recrystallizing and drying the cannabidiol crude product to obtain the cannabidiol.
Preferably, the drying is carried out until the mass content of water in the marihuana leaves is 8-13%.
Preferably, the flow rate of the steam for steam distillation is 20-40 m/s, and the time is 3-5 h.
Preferably, the ethanol extraction agent is an ethanol solution, and the volume concentration of the ethanol solution is 85-95%.
Preferably, the aperture of the separation membrane used for membrane separation is 1-200 nm.
Preferably, the first concentration is performed until the relative density of the obtained first concentrated solution is 1.05 to 1.15.
Preferably, the filler for column chromatography comprises macroporous resin and/or octadecylsilane bonded silica.
Preferably, the eluent for column chromatography is an ethanol solution, and the volume concentration of the ethanol solution is 30-95%.
Preferably, the second concentration is performed until the relative density of the obtained second concentrated solution is 1.10 to 1.25.
Preferably, the recrystallization process is to concentrate the dissolved cannabidiol crude product solution to a supersaturated state under reduced pressure and then cool and crystallize.
According to the method, the hemp flowers and leaves are dried under the conditions that the drying temperature is 40-150 ℃ and the drying time is 2-24 h, so that the cannabidiolic acid (CBDA) contained in the hemp flowers and leaves is converted into CBD through heating decarboxylation reaction, and the conversion efficiency of CBDA is improved; the method prepares the hemp volatile oil by steam distillation, and the prepared hemp volatile oil can be directly used for electronic cigarette oil and perfume flavoring agents, has better market, improves the economic benefit of industrial hemp, can remove water-soluble substances such as chlorophyll, pectin and the like in hemp flowers and leaves, and simplifies the extraction process of CBD. The extraction method provided by the invention can obtain the hemp volatile oil while extracting the CBD, thereby greatly improving the utilization efficiency of hemp flowers and leaves.
Drawings
FIG. 1 is a flow chart of the process for extracting cannabis volatile oil and CBD of the present invention;
FIG. 2 is an HPLC plot of CBD in example 1;
FIG. 3 is an HPLC plot of CBD in example 2;
FIG. 4 is an HPLC plot of CBD in example 3;
FIG. 5 is an HPLC plot of CBD in example 4;
FIG. 6 is an HPLC plot of CBD in example 5;
FIG. 7 is an HPLC chart of CBDA and CBD of hemp flower and leaf powder of example 1;
FIG. 8 is an HPLC chart of CBDA and CBD of hemp flower and leaf powder of example 2;
FIG. 9 is an HPLC chart of CBDA and CBD of hemp flower and leaf powder of example 3;
FIG. 10 is an HPLC chart of CBDA and CBD of hemp flower and leaf powder of example 4;
FIG. 11 is an HPLC chart of CBDA and CBD of hemp flower and leaf powder of example 5;
FIG. 12 is a gas chromatogram of cannabis volatile oil obtained in example 5.
Detailed Description
The invention provides a method for extracting cannabis volatile oil and cannabidiol, which comprises the following steps:
drying and crushing hemp flowers and leaves in sequence to obtain hemp flower and leaf powder, wherein the drying temperature is 40-150 ℃, and the drying time is 2-24 hours;
performing steam distillation on the hemp flower and leaf powder to obtain hemp volatile oil and herb residue;
sequentially carrying out alcohol extraction, membrane separation, first concentration, column chromatography and second concentration on the medicine residues to obtain a cannabidiol crude product;
and sequentially dissolving, recrystallizing and drying the cannabidiol crude product to obtain the cannabidiol.
The source of the hemp flowers and leaves is not particularly specified in the invention, and the hemp flowers and leaves are prepared by adopting the conventional commercial products in the field.
The hemp flower and leaf powder is obtained after the hemp flower and leaf is dried and crushed in sequence. In the invention, the drying temperature is 40-150 ℃, preferably 120-140 ℃, and further preferably 125-130 ℃; the drying time is 2-24 hours, preferably 10-20 hours. The drying equipment is not particularly limited, and the equipment well known in the field can be selected. The drying is preferably carried out until the mass content of the water in the hemp flowers and leaves is 8-13%, and more preferably 9-11%. According to the invention, through controlling the drying temperature and time, the cannabidiolic acid (CBDA) contained in the cannabis leaves is converted into CBD through heating decarboxylation reaction, so that the conversion efficiency of CBDA is improved.
In the present invention, the hemp flower and leaf powder preferably has a particle size of 50 mesh or more. The invention has no special limitation on the crushing process, and can meet the requirement of the particle size.
After obtaining the hemp flower and leaf powder, the invention carries out steam distillation on the hemp flower and leaf powder to obtain hemp volatile oil and dregs.
In the present invention, the steam distillation is preferably performed in a multi-purpose extraction tank, which preferably comprises a reflux condenser, a reflux cooler and a decanter, and the present invention is not particularly limited to the multi-purpose extraction tank, and any multi-purpose extraction tank known in the art may be used; in the embodiment of the invention, a JY-LN type multifunctional extraction, concentration and recovery unit of Shanghai moment source automation technology limited company is adopted. In the invention, the flow velocity of the steam for steam distillation is preferably 20-40 m/s, and more preferably 25-35 m/s; the steam distillation time is preferably 3-5 h, and more preferably 3.5-4.5 h. In the steam distillation process, hemp volatile oil is distilled off with the steam. The method ensures the purity of the hemp volatile oil by controlling the flow rate of the water vapor, reduces the increase of the water content in the hemp volatile oil and reduces impurities.
After the steam distillation is finished, the liquid phase is sequentially cooled and subjected to water-oil separation to obtain the hemp volatile oil. The cooling and water-oil separation processes are not particularly limited in the present invention and may be performed according to processes well known in the art. In the invention, the hemp volatile oil obtained by steam distillation does not need to be purified, can be directly used for electronic cigarette oil and perfume flavoring agent, has better market, and improves the economic benefit of industrial hemp.
And after the steam distillation is finished, obtaining a solid phase which is medicine residue, and after the medicine residue is obtained, sequentially carrying out alcohol extraction, membrane separation, first concentration, column chromatography and second concentration on the medicine residue to obtain a cannabidiol crude product.
In the invention, the ethanol extraction extractant is preferably an ethanol solution, and the volume concentration of the ethanol solution is preferably 85-95%, and more preferably 90-95%. In the invention, the mass ratio of the ethanol solution to the medicine residue is preferably (7.9-10): 1. in the invention, the alcohol extraction is preferably carried out under the reflux condition, and the total time of the alcohol extraction is preferably 6-12 h, more preferably 8-10 h; the number of times of alcohol extraction is preferably 3-4, and the time of alcohol extraction for each time is preferably 2-3 h.
After the alcohol extraction is completed, the obtained alcohol extract is subjected to membrane separation. In the invention, the membrane separation mode is preferably three-stage membrane separation, and the three-stage membrane separation is preferably a first-stage ceramic membrane, a second-stage ultrafiltration membrane and a third-stage nanofiltration membrane; the aperture of the separation membrane used for membrane separation is preferably 1-200 nm; the ceramic membrane is preferably an alumina ceramic membrane, and the aperture of the primary ceramic membrane is preferably 20-50 nm; the alumina ceramic membrane is not particularly limited in the present invention, and any commercially available alumina ceramic membrane known in the art may be used; the aperture of the secondary ultrafiltration membrane is preferably 1-20 nm; the aperture of the three-stage nanofiltration membrane is preferably 1-2 nm. The process of the three-stage membrane separation is not particularly limited in the present invention, and the three-stage membrane separation may be performed using the separation membrane having the above particle size according to a process well known in the art. The invention removes impurities (polysaccharide, flavone, chlorophyll and pectin) by membrane separation.
After the membrane separation is completed, the present invention performs a first concentration on the filtrate obtained by the membrane separation. In the present invention, the first concentration mode is preferably concentration under reduced pressure, and the vacuum degree of the concentration under reduced pressure is preferably-0.01 MPa. The first concentration is preferably carried out until the relative density of the obtained first concentrate is 1.05-1.15. The invention recovers ethanol by first concentration.
After the first concentration is finished, the invention carries out column chromatography separation on the obtained extract. In the present invention, the column chromatography is preferably performed by gradient elution of the column adsorbing the first concentrate with an elution solvent. In the invention, the elution solvent is preferably ethanol water solution with the volume concentration of 30-95%. In the invention, in the process of gradient elution, the volume ratio of water to ethanol is 70: 30. 30: 70 and 5: 95. the present invention preferably performs Thin Layer Chromatography (TLC) follow-up detection simultaneously with gradient elution. The process of TLC follow-up detection is not particularly limited in the present invention and may be performed according to the procedures well known in the art. The invention removes Tetrahydrocannabinol (THC) in the first concentrated product through TLC tracking detection, and improves the purity of CBD.
In the present invention, the filler of the chromatographic column for column chromatography preferably comprises macroporous resin and/or octadecylsilane chemically bonded silica, and when the filler is preferably macroporous resin and octadecylsilane chemically bonded silica, the ratio of the two is not particularly limited in the present invention, and any ratio may be used. Macroporous resins are preferred in embodiments of the invention. In the invention, when the filler of the chromatographic column for column chromatography is preferably macroporous resin, the particle size of the macroporous resin is preferably 16-60 meshes. The octadecylsilane-bonded silica gel of the present invention is not particularly limited, and is commercially available as is well known in the art.
After the column chromatography is completed, the obtained eluent is subjected to second concentration to obtain a cannabidiol crude product. The present invention preferably collects and combines the eluents obtained from each elution stage of the column chromatography according to the same Rf value, and performs the second concentration on the combined eluents with the same Rf value to obtain the crude cannabidiol product. In the present invention, the second concentration mode is preferably concentration under reduced pressure. In the present invention, the second concentration is preferably performed until the relative density of the second concentrated solution is 1.1 to 1.25. In the present invention, the conditions for the second concentration are not particularly limited, and the above relative density may be achieved.
After the cannabidiol crude product is obtained, the cannabidiol crude product is sequentially dissolved, recrystallized and dried to obtain the cannabidiol.
In the invention, the dissolving is preferably carried out in absolute ethyl alcohol, and the mass ratio of the absolute ethyl alcohol to the cannabidiol crude product is preferably (3-6): 1. in the invention, the recrystallization process is preferably to concentrate the dissolved cannabidiol crude product solution to a supersaturated state under reduced pressure and then cool and crystallize. The cooling method of the present invention is not particularly limited, and a cooling method known to those skilled in the art may be used. In the invention, the drying temperature is preferably 40-45 ℃, the drying mode is preferably vacuum drying, and the vacuum degree of the drying is preferably-0.01 MPa.
FIG. 1 is a process flow diagram of the extraction of cannabis volatile oil and CBD of the present invention. The hemp flower and leaf powder is obtained after the hemp flower and leaf is dried and crushed in sequence; performing steam distillation on the hemp flower and leaf powder to obtain hemp volatile oil and dregs; sequentially carrying out alcohol extraction, membrane separation, first concentration, column chromatography and second concentration on the medicine residues to obtain a CBD crude product; and sequentially dissolving, recrystallizing and drying the crude CBD product to obtain the CBD.
The following examples are provided to illustrate the extraction method of cannabis volatile oil and cannabidiol of the present invention in detail, but they should not be construed as limiting the scope of the present invention.
In the following examples, the multifunctional extraction tank used was JY-LN type multifunctional extraction concentration recovery unit from Shanghai Tokyo Automation technology Co.
Example 1
(1) 2760g of fresh hemp flowers and leaves are placed in a tray, placed in a drying oven, dried at 140 ℃ for 2 hours (the mass content of water in the obtained hemp flowers and leaves is 11.2%), crushed and sieved to obtain hemp flower and leaf powder with the particle size of 50 meshes;
(2) placing the hemp flower and leaf powder in a JY-LN type multifunctional extraction concentration recovery unit, introducing water vapor at the flow rate of 20m/s, after 3 hours, sequentially cooling and separating water and oil from the obtained liquid phase to obtain hemp volatile oil, wherein the yield of the obtained hemp volatile oil is 0.8%; the obtained solid phase is 2235g of residue;
(3) adding 95 vol% ethanol solution (22.61L, 17840g, mass ratio of ethanol solution to the residue of 7.98: 1) into multifunctional extraction, concentration and recovery unit, and reflux-extracting the residue for 3 times (2 hr each time) to obtain ethanol extractive solution;
(4) carrying out membrane separation on the alcohol extract in an inorganic ceramic membrane device, removing impurities from a first-grade alumina ceramic membrane (with the aperture of 200nm), a second-grade ultrafiltration membrane (with the aperture of 1-20 nm) and a third-grade nanofiltration membrane (with the aperture of 1-2 nm), carrying out first concentration (reduced pressure concentration, the vacuum degree of-0.01 MPa) on the obtained filtrate through a reduced pressure concentration device until the relative density of the obtained first concentrate is 1.05, and recovering ethanol to obtain an extract;
(5) and (2) passing the extract through an octadecylsilane chemically bonded silica chromatographic column, and performing gradient elution, wherein in the process of gradient elution, an elution solvent is an ethanol water solution (the volume concentration is 30-95%), and the volume ratio of water to ethanol is 70: 30. 30: 70 and 5: 95, carrying out thin-layer chromatography tracking detection while carrying out gradient elution, collecting and combining eluates at each stage of the gradient elution according to the condition of the same Rf value, and carrying out second concentration on the combined eluates with the same Rf value until the relative density of the obtained second concentrated solution is 1.1, so as to obtain a crude product of the CBD;
(6) and dissolving the crude CBD product in absolute ethyl alcohol with the mass of 3 times, concentrating the obtained crude CBD product solution under reduced pressure to a supersaturated state, cooling and crystallizing, and carrying out vacuum drying at 45 ℃ under the condition that the vacuum degree is-0.01 MPa to obtain the CBD.
The purity of the obtained CBD is determined by high performance liquid chromatography (as shown in figure 2), and the purity of the CBD can reach 99.3% by detection.
According to the calculation of the EU calculation method, the calculated CBD yield is 65%, and the calculation formula is shown as the formula 1:
the theoretical content of CBD is ═ (CBD content + CBDA content x 0.877) ÷ cannabis leaves raw material mass x 100% formula 1
Example 2
(1) Putting 3500g of fresh hemp flower and leaf in a tray, putting in a drying oven, drying at 140 ℃ for 4h (the mass content of water in the hemp flower and leaf is 11%), crushing, and sieving to obtain hemp flower and leaf powder with the particle size of 50 meshes;
(2) placing the hemp flower and leaf powder in a JY-LN type multifunctional extraction concentration recovery unit, introducing water vapor at the flow rate of 20m/s, after 3 hours, sequentially cooling and separating water and oil from the obtained liquid phase to obtain hemp volatile oil, wherein the yield of the obtained hemp volatile oil is 0.5%; the obtained solid phase is 2780g of decoction dregs;
(3) adding 95 vol% ethanol solution (22960 g; 29.1L, the mass ratio of ethanol solution to the residue is 8.26:1) into a multifunctional extraction, concentration and recovery unit, and extracting the residue under reflux for 3 times (each time for 3 hr) to obtain ethanol extractive solution;
(4) carrying out three-stage membrane separation on the alcohol extract, removing impurities by using a first-stage alumina ceramic membrane (with the aperture of 200nm), a second-stage ultrafiltration membrane (with the aperture of 1-20 nm) and a third-stage nanofiltration membrane (with the aperture of 1-2 nm), carrying out first concentration (reduced pressure concentration, the vacuum degree of-0.01 MPa) on the obtained filtrate by using reduced pressure concentration equipment until the relative density of the obtained first concentrate is 1.05, and recovering ethanol to obtain an extract;
(5) and (2) passing the extract through an octadecylsilane chemically bonded silica chromatographic column, and performing gradient elution, wherein in the process of gradient elution, an elution solvent is an ethanol water solution (the volume concentration is 30-95%), and the volume ratio of water to ethanol is 70: 30. 30: 70 and 5: 95, carrying out thin-layer chromatography tracking detection while carrying out gradient elution, collecting and combining eluates at each stage of the gradient elution according to the condition of the same Rf value, and carrying out second concentration on the combined eluates with the same Rf value until the relative density of the obtained second concentrated solution is 1.1, so as to obtain a crude product of the CBD;
(6) and dissolving the crude CBD product in absolute ethyl alcohol with the mass of 3 times, concentrating the obtained crude CBD product solution under reduced pressure to a supersaturated state, cooling and crystallizing, and carrying out vacuum drying at 45 ℃ under the condition that the vacuum degree is-0.01 MPa to obtain the CBD.
The purity of the obtained CBD is determined by high performance liquid chromatography (as shown in figure 3), and the purity of the CBD can reach 99.5% by detection.
The CBD yield was calculated to be 62% in the same manner as in example 1.
Example 3
(1) Putting 4500g of fresh hemp flower and leaf in a tray, putting into a drying oven, drying at 70 ℃ for 2h (the mass content of water in the obtained hemp flower and leaf is 10.8%), crushing, and sieving to obtain hemp flower and leaf powder with the particle size of 50 meshes;
(2) placing the hemp flower and leaf powder in a JY-LN type multifunctional extraction concentration recovery unit, introducing water vapor at the flow rate of 40m/s, after 3 hours, sequentially cooling and separating water and oil from the obtained liquid phase to obtain hemp volatile oil, wherein the yield of the obtained hemp volatile oil is 1.2%; the obtained solid phase is 3612g of decoction dregs;
(3) adding 95 vol% ethanol solution (28800g, 36.5L, mass ratio of ethanol solution to the residue is 7.97:1) into multifunctional extraction concentration recovery unit, and reflux-extracting the residue for 3 times (each for 3 hr) to obtain ethanol extractive solution;
(4) carrying out three-stage membrane separation on the alcohol extract, removing impurities by using a first-stage alumina ceramic membrane (with the aperture of 200nm), a second-stage ultrafiltration membrane (with the aperture of 1-20 nm) and a third-stage nanofiltration membrane (with the aperture of 1-2 nm), carrying out first concentration (reduced pressure concentration, the vacuum degree of-0.01 MPa) on the obtained filtrate by using reduced pressure concentration equipment until the relative density of the obtained first concentrate is 1.05, and recovering ethanol to obtain an extract;
(5) and (2) passing the extract through an octadecylsilane chemically bonded silica chromatographic column, and performing gradient elution, wherein in the process of gradient elution, an elution solvent is an ethanol water solution (the volume concentration is 30-95%), and the volume ratio of water to ethanol is 70: 30. 30: 70 and 5: 95, carrying out thin-layer chromatography tracking detection while carrying out gradient elution, collecting and combining eluates at each stage of the gradient elution according to the condition of the same Rf value, and carrying out second concentration on the combined eluates with the same Rf value until the relative density of the obtained second concentrated solution is 1.1, so as to obtain a crude product of the CBD;
(6) and dissolving the crude CBD product in absolute ethyl alcohol with the mass of 6 times, concentrating the obtained crude CBD product solution under reduced pressure to a supersaturated state, cooling and crystallizing, and carrying out vacuum drying at 45 ℃ under the condition that the vacuum degree is-0.01 MPa to obtain the CBD.
The purity of the obtained CBD is determined by high performance liquid chromatography (as shown in figure 4), and the purity of the CBD can reach 99.2% by detection.
The CBD yield was calculated to be 35% in the same manner as in example 1.
Example 4
(1) 2800g of fresh hemp flower and leaf are placed in a tray, the tray is placed in a drying oven, after being dried for 12 hours at 40 ℃ (the mass content of the moisture of the hemp flower and leaf is 11.2%), the powder is crushed and sieved, and hemp flower and leaf powder with the grain size of 50 meshes is obtained;
(2) placing the hemp flower and leaf powder in a JY-LN type multifunctional extraction concentration recovery unit, introducing water vapor at the flow rate of 20m/s, after 3 hours, sequentially cooling and separating water and oil from the obtained liquid phase to obtain hemp volatile oil, wherein the yield of the obtained hemp volatile oil is 1.5%; the obtained solid phase is 2296g of medicinal residue;
(3) adding 95 vol% ethanol solution (19516g, 24.7L, and the mass ratio of ethanol solution to the residue is 8.5:1) into multifunctional extraction, concentration and recovery unit, and reflux-extracting the residue for 3 times (2 hr each time) to obtain ethanol extractive solution;
(4) carrying out three-stage membrane separation on the alcohol extract, removing impurities by using a first-stage alumina ceramic membrane (with the aperture of 200nm), a second-stage ultrafiltration membrane (with the aperture of 1-20 nm) and a third-stage nanofiltration membrane (with the aperture of 1-2 nm), carrying out first concentration (reduced pressure concentration, the vacuum degree of-0.01 MPa) on the obtained filtrate by using reduced pressure concentration equipment until the relative density of the obtained first concentrate is 1.05, and recovering ethanol to obtain an extract;
(5) and (2) passing the extract through an octadecylsilane chemically bonded silica chromatographic column, and performing gradient elution, wherein in the process of gradient elution, an elution solvent is an ethanol water solution (the volume concentration is 30-95%), and the volume ratio of water to ethanol is 70: 30. 30: 70 and 5: 95, carrying out thin-layer chromatography tracking detection while carrying out gradient elution, collecting and combining eluates at each stage of the gradient elution according to the condition of the same Rf value, and carrying out second concentration on the combined eluates with the same Rf value until the relative density of the obtained second concentrated solution is 1.1, so as to obtain a crude product of the CBD;
(6) and dissolving the crude CBD product in absolute ethyl alcohol with the mass of 3 times, concentrating the obtained crude CBD product solution under reduced pressure to a supersaturated state, cooling and crystallizing, and carrying out vacuum drying at 45 ℃ under the condition that the vacuum degree is-0.01 MPa to obtain the CBD.
The purity of the obtained CBD is determined by high performance liquid chromatography (as shown in figure 5), and the purity of the CBD can reach 99% 5 by detection.
The CBD yield was calculated to be 21% in the same manner as in example 1.
Example 5
(1) Putting 3000g of fresh hemp flower and leaf in a tray, putting the tray in a drying box, drying for 24 hours at 40 ℃ (the mass content of water in the hemp flower and leaf is 10.8%), crushing and sieving to obtain hemp flower and leaf powder with the particle size of 50 meshes;
(2) placing the hemp flower and leaf powder in a JY-LN type multifunctional extraction concentration recovery unit, introducing water vapor at the flow rate of 20m/s, after 3 hours, sequentially cooling and separating water and oil from the obtained liquid phase to obtain hemp volatile oil, wherein the yield of the obtained hemp volatile oil is 1.5%; the obtained solid phase is 2430g of decoction dregs;
(3) adding 95 vol% ethanol solution (20655g, 26.18L, the mass ratio of ethanol solution to the residue is 8.5:1) into multifunctional extraction, concentration and recovery unit, and reflux-extracting the residue for 3 times (each time for 3 hr) to obtain ethanol extractive solution;
(4) carrying out three-stage membrane separation on the alcohol extract, removing impurities by using a first-stage alumina ceramic membrane (with the aperture of 200nm), a second-stage ultrafiltration membrane (with the aperture of 1-20 nm) and a third-stage nanofiltration membrane (with the aperture of 1-2 nm), carrying out first concentration (reduced pressure concentration, the vacuum degree of-0.01 MPa) on the obtained filtrate by using reduced pressure concentration equipment until the relative density of the obtained first concentrate is 1.05, and recovering ethanol to obtain an extract;
(5) and (2) passing the extract through an octadecylsilane chemically bonded silica chromatographic column, and performing gradient elution, wherein in the process of gradient elution, an elution solvent is an ethanol water solution (the volume concentration is 30-95%), and the volume ratio of water to ethanol is 70: 30. 30: 70 and 5: 95, carrying out thin-layer chromatography tracking detection while carrying out gradient elution, collecting and combining eluates at each stage of the gradient elution according to the condition of the same Rf value, and carrying out second concentration on the combined eluates with the same Rf value until the relative density of the obtained second concentrated solution is 1.1, so as to obtain a crude product of the CBD;
(6) and dissolving the crude CBD product in absolute ethyl alcohol with the mass of 3 times, concentrating the obtained crude CBD product solution under reduced pressure to a supersaturated state, cooling and crystallizing, and carrying out vacuum drying at 45 ℃ under the condition that the vacuum degree is-0.01 MPa to obtain the CBD.
The purity of the obtained CBD is determined by high performance liquid chromatography (as shown in figure 6), and the purity of the CBD can reach 99.6% by detection.
The CBD yield was calculated to be 21% in the same manner as in example 1.
Comparative example 1
The content analysis of cannabidiol in different varieties of industrial cannabis sativa (Wangdan, etc., school report of Qizihal university, Nature science edition), 2019, 35(4):49-54) in the prior art is used as a comparative example, the content analysis of different varieties of industrial cannabis sativa is carried out, and a shade drying method (naturally airing at room temperature and in dark place) is adopted for the pretreatment of hemp flowers and leaves, so that the maximum CBD yield in the industrial cannabis sativa obtained by the method is only 4.13%.
Performance detection
Respectively recording the extracts prepared in the step (4) of the embodiments 1-5 as A1, A2, A3, A4 and A5, precisely weighing 0.200g of the A1-A5 samples, and parallelly sampling each sample for 3 times;
putting the samples into conical flasks respectively, and adding 10mL of ethanol solution with volume concentration of 95% for ultrasonic extraction for 30min (3 times in total);
after filtering, merging the filtrates obtained by 3 parallel samples and evaporating to dryness; then adding methanol into the obtained filtrate to reach a constant volume of 10 mL; and (3) carrying out ultrasonic full dissolution, filtering the solution through a microporous filter membrane (0.22mm), and measuring CBDA and CBD in the hemp according to a standard curve by high performance liquid chromatography, wherein the linear regression equation is 2106.1x +185.78 and Y5153.3 x +222.6, so as to obtain an HPLC (high performance liquid chromatography) diagram of CBDA and CBD, as shown in figures 7-11.
Fig. 7 to 11 are HPLC charts of CBDA and CBD measured on the cannabis sativa flower and leaf powder prepared in examples 1 to 5, respectively, and it can be seen from the peak area values of fig. 7 to 11 that the CBDA content in the sample decreases and the corresponding CBD content increases with the increase of the drying temperature according to the linear regression equation of CBDA and CBD, mainly because the CBDA in the cannabis sativa flower and leaf is converted into CBD by drying the cannabis sativa flower and leaf, the utilization rate and economic value of the cannabis sativa flower and leaf are improved.
FIG. 12 is a gas chromatogram of the cannabis volatile oil obtained in example 5. Compared with gas chromatography library, the hemp volatile oil mainly contains beta-linalool, beta-cis-ocimene, camphor, borneol, menthol, yak-yakene D, alpha-apiene, beta-caryophyllene, caryophyllene oxide, delta-guaiene, alpha-caryophyllene and the like.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (10)
1. A method for extracting cannabis volatile oil and cannabidiol comprises the following steps:
drying and crushing hemp flowers and leaves in sequence to obtain hemp flower and leaf powder, wherein the drying temperature is 40-150 ℃, and the drying time is 2-24 hours;
performing steam distillation on the hemp flower and leaf powder to obtain hemp volatile oil and herb residue;
sequentially carrying out alcohol extraction, membrane separation, first concentration, column chromatography and second concentration on the medicine residues to obtain a cannabidiol crude product;
and sequentially dissolving, recrystallizing and drying the cannabidiol crude product to obtain the cannabidiol.
2. The extraction method according to claim 1, wherein the drying is performed until the moisture content in the cannabis sativa leaves is 8-13% by mass.
3. The extraction method according to claim 1, wherein the flow rate of the steam for steam distillation is 20 to 40m/s, and the time is 3 to 5 hours.
4. The extraction method according to claim 1, wherein the alcohol extraction extractant is an ethanol solution, and the volume concentration of the ethanol solution is 85-95%.
5. The extraction method according to claim 1, wherein the pore diameter of the separation membrane used for membrane separation is 1 to 200 nm.
6. The extraction method according to claim 1, wherein the first concentration is performed so that a relative density of the obtained first concentrated solution is 1.05 to 1.15.
7. The extraction method according to claim 1, wherein the filler for column chromatography comprises macroporous resin and/or octadecylsilane bonded silica.
8. The extraction method according to claim 1 or 7, wherein the eluent for column chromatography is an ethanol solution, and the volume concentration of the ethanol solution is 30-95%.
9. The extraction method according to claim 1, wherein the second concentration is performed so that a relative density of the obtained second concentrated solution is 1.10 to 1.25.
10. The extraction method as claimed in claim 1, wherein the recrystallization step comprises concentrating the dissolved cannabidiol crude solution under reduced pressure to supersaturation, and cooling for crystallization.
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