CN114380666B - Industrial extraction method of cannabidiol - Google Patents
Industrial extraction method of cannabidiol Download PDFInfo
- Publication number
- CN114380666B CN114380666B CN202011117895.9A CN202011117895A CN114380666B CN 114380666 B CN114380666 B CN 114380666B CN 202011117895 A CN202011117895 A CN 202011117895A CN 114380666 B CN114380666 B CN 114380666B
- Authority
- CN
- China
- Prior art keywords
- extraction
- cannabidiol
- solvent
- liquid
- extracting
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 238000000605 extraction Methods 0.000 title claims abstract description 90
- QHMBSVQNZZTUGM-UHFFFAOYSA-N Trans-Cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-UHFFFAOYSA-N 0.000 title claims abstract description 76
- QHMBSVQNZZTUGM-ZWKOTPCHSA-N cannabidiol Chemical compound OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-ZWKOTPCHSA-N 0.000 title claims abstract description 76
- 229950011318 cannabidiol Drugs 0.000 title claims abstract description 76
- ZTGXAWYVTLUPDT-UHFFFAOYSA-N cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CC=C(C)C1 ZTGXAWYVTLUPDT-UHFFFAOYSA-N 0.000 title claims abstract description 76
- PCXRACLQFPRCBB-ZWKOTPCHSA-N dihydrocannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)C)CCC(C)=C1 PCXRACLQFPRCBB-ZWKOTPCHSA-N 0.000 title claims abstract description 75
- 239000002904 solvent Substances 0.000 claims abstract description 65
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 57
- 244000025254 Cannabis sativa Species 0.000 claims abstract description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 38
- 235000008697 Cannabis sativa Nutrition 0.000 claims abstract description 32
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 26
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000003208 petroleum Substances 0.000 claims abstract description 14
- 239000002994 raw material Substances 0.000 claims abstract description 14
- 235000015112 vegetable and seed oil Nutrition 0.000 claims abstract description 14
- 239000008158 vegetable oil Substances 0.000 claims abstract description 14
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 43
- 239000007788 liquid Substances 0.000 claims description 24
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 claims description 17
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 claims description 17
- 235000009120 camo Nutrition 0.000 claims description 17
- 235000005607 chanvre indien Nutrition 0.000 claims description 17
- 239000011487 hemp Substances 0.000 claims description 17
- 238000003756 stirring Methods 0.000 claims description 16
- 230000001877 deodorizing effect Effects 0.000 claims description 13
- 238000001035 drying Methods 0.000 claims description 13
- 239000002023 wood Substances 0.000 claims description 12
- 239000002674 ointment Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 3
- CYQFCXCEBYINGO-UHFFFAOYSA-N THC Natural products C1=C(C)CCC2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 CYQFCXCEBYINGO-UHFFFAOYSA-N 0.000 abstract description 19
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 abstract description 19
- 229960004242 dronabinol Drugs 0.000 abstract description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 15
- 238000000638 solvent extraction Methods 0.000 abstract description 15
- 238000000622 liquid--liquid extraction Methods 0.000 abstract description 14
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract description 13
- 238000000034 method Methods 0.000 abstract description 13
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 abstract description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract description 5
- 238000013375 chromatographic separation Methods 0.000 abstract description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 abstract description 5
- 238000005469 granulation Methods 0.000 abstract description 3
- 230000003179 granulation Effects 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 238000004042 decolorization Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 45
- 238000001914 filtration Methods 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000284 extract Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 238000007670 refining Methods 0.000 description 5
- 241000218236 Cannabis Species 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 238000010812 external standard method Methods 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000469 ethanolic extract Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000010829 isocratic elution Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Classifications
-
- 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
- C07C37/685—Processes comprising at least two steps in series
-
- 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
- C07C37/72—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
-
- 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
- C07C37/82—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a method for extracting cannabidiol from 40-60 mesh cannabis sativa leaves, which comprises the following steps of raw material pretreatment, granulation, extraction, liquid-liquid extraction, decolorization and concentration, and is characterized in that the raw material is crushed to 40-60 mesh in the raw material pretreatment stage, and the extraction solvent and the extracting agent of the liquid-liquid extraction are specifically selected, wherein the extraction solvent is selected from one or more than two of n-hexane, cyclohexane, n-heptane, petroleum ether, vegetable oil extraction solvent, ethyl acetate and butyl acetate, and the extracting agent of the liquid-liquid extraction is selected from one or more than two of methanol, ethanol, amyl alcohol, butanol and isopropanol. Compared with the prior art, the yield can be further improved by 7-8% by crushing the raw materials to 40-60 meshes in the raw material pretreatment stage and crushing the raw materials to 10-30 meshes. Through selection of an extraction solvent and an extraction agent, waxy components and cannabidiol are effectively separated by a liquid-liquid extraction process, meanwhile, the extraction rate of cannabidiol is improved, 40% of tetrahydrocannabinol in an extraction solution is removed, the pressure for further chromatographic separation of CBD and THC in the follow-up process can be greatly reduced, and convenience is provided for the follow-up production process.
Description
Technical Field
The invention relates to the technical field of cannabidiol preparation, in particular to an industrial extraction method of cannabidiol.
Background
Cannabidiol (CBD) is a main chemical component of medicinal plant cannabis sativa, is extracted from female cannabis sativa plant, is a non-addictive component of cannabis sativa, and has pharmacological effects of antispasmodic, anxiolytic, antiinflammatory, etc.
Tetrahydrocannabinol (THC for short) is the main active ingredient of cannabis drugs and has mental and medical activity after ingestion or oral administration. The health of the human body is seriously damaged by a large amount or long-term use.
Since tetrahydrocannabinol belongs to a forbidden component, it must be removed during the preparation of cannabidiol. If a large portion of tetrahydrocannabinol is removed prior to refining cannabidiol, the number of subsequent separation and refining steps can be reduced, and the cost of the separation and refining steps can be significantly reduced. At present, cannabidiol is extracted from plant cannabis by an extraction separation method, and in the primary extraction process, the extract is inevitably mixed with tetrahydrocannabinol and other impurities such as wax and the like. The existence of wax can influence the physicochemical properties of the extract, further influence the subsequent refining steps of cannabidiol, such as influencing the elution efficiency in the subsequent column chromatographic separation, reducing the yield of cannabidiol, and the like.
The current cannabidiol preparation process is low in industrialized application degree, cannot form large-scale production, and can not extract waxy components in raw materials by conventional solvent extraction, and the subsequent winterization treatment is carried out, so that partial waxy can be removed, but the removal effect is poor, and the cost is high.
Patent 201610087327.6 discloses a cannabis sativa extract rich in cannabidiol extracted from leaves of industrial cannabis sativa and a preparation method thereof, wherein the patent utilizes subcritical butane extraction technology to extract to obtain a crude extract, and then ethanol is used for dissolving the extract and carrying out low-temperature winterization treatment, and the wax is centrifugally removed.
The prior patent application CN110655453A, CN110256206a describes extracting cannabis with methanol or ethanol, concentrating the obtained ethanol extract, further adding n-hexane or petroleum ether for extraction to obtain an organic layer, and recovering the organic solvent to obtain a cannabis extract intermediate product. Compared with the process, the extraction process has the advantages that the extraction yield of cannabidiol is higher, the content of tetrahydrocannabinol in the extract is reduced, and a better technical effect is achieved.
The applicant discloses an industrialized extraction method of cannabidiol (application number 2020105461090), which utilizes a liquid-liquid extraction process to effectively separate waxy components from cannabidiol through selection of an extraction solvent and an extraction agent, improves the extraction rate of the cannabidiol and removes 40% of tetrahydrocannabinol in an extraction solution, can greatly reduce the pressure of further chromatographic separation of CBD and THC, and provides convenience for the subsequent production process.
Disclosure of Invention
In the prior application (application number 2020105461090), the inventor of the application further researches and discovers that when the cannabis sativa leaf raw material is crushed to 40-60 meshes, the extraction yield of cannabidiol can be improved by 7% -8% compared with the original 10-30 meshes.
The inventive contribution of the present application is therefore:
(1) When the raw materials are selected, the raw materials of the cannabis sativa leaves with 40-60 meshes are selected, so that the extraction yield of cannabidiol is improved by 7-8% compared with the original extraction yield of cannabidiol with 10-30 meshes;
(2) Through the selection of an extraction solvent and an extractant for liquid-liquid extraction, waxy components and cannabidiol are effectively separated by using a liquid-liquid extraction process, meanwhile, the extraction rate of cannabidiol is improved, 40% tetrahydrocannabinol in an extraction solution is removed, the pressure for further chromatographic separation of CBD and THC in the follow-up process can be greatly reduced, and convenience is provided for the follow-up production process. The extraction solvent is one or a mixture of more than two of n-hexane, cyclohexane, n-heptane, petroleum ether, vegetable oil extraction solvent, ethyl acetate and butyl acetate; the extraction solvent is one or more of methanol, ethanol, amyl alcohol, butanol and isopropanol.
The method for extracting cannabidiol by using the 40-60 mesh cannabis sativa leaves comprises the following specific steps:
step one, preparing materials, namely 40-60 meshes of hemp flowers;
step two, extracting the dried cannabis sativa leaves in the step one by a solvent, concentrating an extracting solution until a certain amount of extracting solvent remains, wherein the extracting solvent is one or a mixture of more than two of n-hexane, cyclohexane, n-heptane, petroleum ether, vegetable oil extracting solvent, ethyl acetate and butyl acetate;
step three, adding other solvents into the concentrated solution obtained in the step two for extraction, wherein the extraction solvent is one or a mixture of more than two of methanol, ethanol, amyl alcohol, butanol and isopropanol;
step four, separating out the lower layer liquid treated in the step three, and adding activated carbon to stir and decolor;
and fifthly, concentrating the decolorized solution obtained in the fourth step, and deodorizing to obtain the cannabidiol-enriched ointment.
In the step one of the industrialized extraction method of cannabidiol, the temperature is preferably 120-140 ℃ when heating or drying; further preferably 125-135 ℃; most preferably 130 ℃.
Preferably, the hemp leaves are crushed to 40-50 mesh, more preferably 40 mesh.
In the step two of the industrialized extraction method of cannabidiol, the cannabis sativa leaves are granulated and then extracted.
In the step two of the industrial extraction method of cannabidiol, the extraction solvent is organic solvents such as n-hexane, cyclohexane, n-heptane, petroleum ether, vegetable oil extraction solvent, ethyl acetate, butyl acetate and the like, and the mass/volume ratio (g/mL) of the cannabis sativa leaves to the extraction solvent is 1:4-8.
In the step two of the industrialized extraction method of cannabidiol, the extracting solution is concentrated to 1/15-1/5 of the volume of the original solvent; preferably 1/12 to 1/1/8; most preferably 1/10.
In the step two of the industrial extraction method of cannabidiol, the extraction solvent is preferably n-hexane, petroleum ether or vegetable oil extraction solvent.
In the step three of the industrialized extraction method of cannabidiol, the used extraction solvents are methanol, ethanol, amyl alcohol, butanol, isopropanol and the like, the volume ratio of the concentrated solution to the extraction solvents is 1:2-6, and the two-phase solvents are completely separated by stirring for 10-30 min and standing for 60-120 min after adding.
In the step three of the industrialized extraction method of cannabidiol, the extractant is preferably 60% -75% of methanol, ethanol, amyl alcohol, butanol and isopropanol; the extraction agent of the further step is preferably 60% -75% of methanol and ethanol.
In the step four of the industrialized extraction method of cannabidiol, the addition amount of the activated carbon is 0.1% -3% (g/ml) of the lower layer liquid.
In the fourth step of the industrialized extraction method of cannabidiol, the activated carbon is wood porous activated carbon, and the treatment time is 5-10 minutes.
The application also provides a preferred industrialized extraction method of cannabidiol, which is characterized by comprising the following steps:
crushing the hemp leaves to 40-60 meshes, and heating, stir-frying or drying at 120-140 ℃;
granulating the dried cannabis sativa leaves, and then extracting the granulated cannabis sativa leaves with organic solvents such as normal hexane, cyclohexane, normal heptane, petroleum ether, vegetable oil extraction solvents, ethyl acetate, butyl acetate and the like, and concentrating the extracting solution until the volume of the extracting solution is 1/15-1/5 of that of the original solvent;
step three, adding methanol, ethanol, amyl alcohol, butanol, isopropanol and the like into the concentrated solution obtained in the step two for extraction;
step four, separating out the lower layer liquid treated in the step three, and adding activated carbon to stir and decolor;
and fifthly, concentrating the decolorized solution obtained in the fourth step, and deodorizing to obtain the cannabidiol-enriched ointment.
The application also provides a preferred industrialized extraction method of cannabidiol, which is characterized by comprising the following steps:
crushing the hemp leaves to 40-50 meshes, and heating, stir-frying or drying at 125-135 ℃;
granulating the dried cannabis sativa leaves in the step one, and extracting the granulated cannabis sativa leaves with normal hexane, petroleum ether and vegetable oil extraction solvent in a solvent way, wherein the mass/volume ratio (g/mL) of the cannabis sativa leaves to the extraction solvent is 1:4-8; concentrating the extracting solution to 1/12-1/8 of the volume of the original solvent;
step three, adding 60% -75% of methanol, ethanol, amyl alcohol, butanol and isopropanol into the concentrated solution obtained in the step two for extraction, wherein the volume ratio of the concentrated solution to the extraction solvent is 1:2-6;
step four, separating out the lower layer liquid treated in the step three, and adding activated carbon to stir and decolor;
and fifthly, concentrating the decolorized solution obtained in the fourth step, and deodorizing to obtain the cannabidiol-enriched ointment.
The application also provides a preferred industrialized extraction method of cannabidiol, which is characterized by comprising the following steps:
crushing the hemp leaves to 40 meshes, and heating, stir-frying or drying the hemp leaves at 130 ℃;
granulating the dried cannabis sativa leaves in the step one, and extracting the granulated cannabis sativa leaves with normal hexane, petroleum ether and vegetable oil extraction solvent in a solvent way, wherein the mass/volume ratio (g/mL) of the cannabis sativa leaves to the extraction solvent is 1:4-8; concentrating the extracting solution to 1/10 of the volume of the original solvent;
step three, adding 60% -75% of methanol and ethanol into the concentrated solution obtained in the step two for extraction, wherein the volume ratio of the concentrated solution to the extraction solvent is 1:2-6, stirring for 10-30 min after adding, and standing for 60-120 min;
step four, separating out the lower layer liquid treated in the step three, and adding wood porous activated carbon for stirring and decoloring for 5-10 minutes;
and fifthly, concentrating the decolorized solution obtained in the fourth step, and deodorizing to obtain the cannabidiol-enriched ointment.
In the second step of the invention, a granulating technology is used, so that the solvent is fully contacted with the materials in the leaching process, the extraction yield is greatly improved, and the filtering speed of the feed liquid is improved. The granulation method uses a conventional granulation method. The vegetable oil extraction solvent in the extraction solvent is an aliphatic hydrocarbon solvent, mainly comprising hexane, pentane, butane, propane and mixtures thereof, especially a mixture of hexane; the vegetable oil extraction solvent refers to a vegetable oil solvent extractant which accords with the national current standard.
The extraction step of the second step of the invention can lead the waxy and tetrahydrocannabinol to be left in the original extracting solution, and the cannabidiol is back extracted into the extracting agent.
In the fourth step of the invention, the proportion of the added active carbon is 0.1% -3%, so that the impurity color can be removed, the purity of cannabidiol is improved, and the appearance of the product is improved; the activated carbon is preferably wood porous activated carbon, the effect can be achieved after decolorization treatment for 5-10 minutes, and impurities can be treated under the condition of removing the color, so that the purity of cannabidiol in the extract is improved.
Detailed Description
The invention is further illustrated, but is not limited in any way, by the following examples, and any alterations or substitutions based on the teachings of the invention are within the scope of the invention.
Test method
The method for measuring the content of cannabidiol and tetrahydrocannabinol comprises the following steps:
(1) Detecting the liquid to be detected by adopting a high performance liquid chromatograph, wherein the mobile phase of the high performance liquid chromatograph is water and acetonitrile, and the liquid is eluted at equal degree; the mobile phase acetonitrile is chromatographic pure, the water is deionized water, and the ratio of acetonitrile to water is 70%:30%, isocratic elution, flow rate of 1.2mL/min; the sample injection amount of the high performance liquid chromatograph is 10uL; the column temperature of the high performance liquid chromatograph is 40 ℃; the detection wavelength of the high performance liquid chromatograph is 220nm.
(2) Quantification was performed using an external standard method: preparing a series of reference substance solutions by using cannabidiol and tetrahydrocannabinol standard reference substances, and respectively detecting the content of cannabidiol and tetrahydrocannabinol in the products obtained by chromatographic separation by an external standard method.
The method for calculating the yield of cannabidiol comprises the following steps:
cannabidiol yield/% = cannabidiol oil paste weight in ointment/cannabidiol content in cannabidiol leaves weight in cannabidiol leaves.
Example 1
Crushing 230g of sun-dried cannabis sativa leaves to 40 meshes, and heating and drying in a baking oven at 130 ℃ for 1h;
step two, adding 200g of the hemp leaves in the step one into 1% water, granulating to form solid particles, extracting by using 1000ml of petroleum ether with the volume being 5 times of that of the hemp leaves in proportion, filtering the extracting solution, and concentrating the extracting solution to the residual 100ml;
step three, adding 300ml of 70% methanol solvent into the concentrated solution obtained by the treatment in the step two for liquid-liquid extraction;
step four, separating out the methanol layer obtained after the treatment in the step three, adding 3g of wood activated carbon, stirring for 10min, and filtering to obtain clear and transparent feed liquid;
and fifthly, concentrating and deodorizing the methanol decolorized solution obtained in the fourth step to obtain 17.5g of cannabidiol-rich oil paste.
Example 2
Step one, crushing 460g of cannabis sativa leaves to 50 meshes, and heating and drying in a baking oven at 130 ℃ for 1h;
step two, adding 400g of dried cannabis sativa leaves in the step one into 1.5% water, granulating to form solid particles, extracting by using 3200ml of vegetable oil extraction solvent, filtering the extraction liquid, and concentrating to the residual 320ml;
adding 1280ml of 75% ethanol solvent into the concentrated solution obtained by the treatment in the step two for liquid-liquid extraction;
step four, separating out the ethanol layer obtained after the treatment in the step three, adding 25.6g of wood activated carbon, stirring for 5min, and filtering to obtain clear and transparent feed liquid;
and fifthly, concentrating and deodorizing the ethanol decolorized solution obtained in the fourth step to obtain 32.8g of cannabidiol-enriched oil paste.
Example 3
Crushing 120g of sun-dried cannabis sativa leaves to 60 meshes, and heating and drying in a baking oven at 130 ℃ for 1h;
step two, 100g of the hemp leaves in the step one are added with 1% of water and then granulated to form solid particles, 500ml of solvent of 5 times of volume of normal hexane is used for extraction according to the proportion, and the extracting solution is filtered and concentrated to the residual 60ml;
step three, adding 240ml of 72% isopropanol solvent into the concentrated solution obtained by the treatment in the step two for liquid-liquid extraction;
step four, separating out the isopropanol layer obtained after the treatment in the step three, adding 3g of wood activated carbon, stirring for 10min, and filtering to obtain clear transparent feed liquid;
and fifthly, concentrating and deodorizing the isopropyl alcohol decolorized solution obtained in the fourth step to obtain 8.3g of cannabidiol-enriched oil paste.
Comparative example 1
Crushing 230g of sun-dried cannabis sativa leaves to 20 meshes, and heating and drying in a baking oven at 130 ℃ for 1h;
step two, adding 200g of the hemp leaves in the step one into 1% water, granulating to form solid particles, extracting by using 1000ml of petroleum ether with the volume being 5 times of that of the hemp leaves in proportion, filtering the extracting solution, and concentrating the extracting solution to the residual 100ml;
step three, adding 300ml of 70% methanol solvent into the concentrated solution obtained by the treatment in the step two for liquid-liquid extraction;
step four, separating out the methanol layer obtained after the treatment in the step three, adding 3g of wood activated carbon, stirring for 10min, and filtering to obtain clear and transparent feed liquid;
and fifthly, concentrating and deodorizing the methanol decolorized solution obtained in the fourth step to obtain 16g of cannabidiol-rich ointment.
Comparative example 2
Step one, crushing 460g of cannabis sativa leaves to 10 meshes, and heating and drying in a baking oven at 130 ℃ for 1h;
step two, adding 400g of dried cannabis sativa leaves in the step one into 1.5% water, granulating to form solid particles, extracting by using 3200ml of vegetable oil extraction solvent, filtering the extraction liquid, and concentrating to the residual 320ml;
adding 1280ml of 75% ethanol solvent into the concentrated solution obtained by the treatment in the step two for liquid-liquid extraction;
step four, separating out the ethanol layer obtained after the treatment in the step three, adding 25.6g of wood activated carbon, stirring for 5min, and filtering to obtain clear and transparent feed liquid;
and fifthly, concentrating and deodorizing the ethanol decolorized solution obtained in the fourth step to obtain 29.5g of cannabidiol-enriched oil paste.
Comparative example 3
Crushing 120g of sun-dried cannabis sativa leaves to 30 meshes, and heating and drying in a baking oven at 130 ℃ for 1h;
step two, 100g of the hemp leaves in the step one are added with 1% of water and then granulated to form solid particles, 500ml of solvent of 5 times of volume of normal hexane is used for extraction according to the proportion, and the extracting solution is filtered and concentrated to the residual 60ml;
step three, adding 240ml of 72% isopropanol solvent into the concentrated solution obtained by the treatment in the step two for liquid-liquid extraction;
step four, separating out the isopropanol layer obtained after the treatment in the step three, adding 3g of wood activated carbon, stirring for 10min, and filtering to obtain clear transparent feed liquid;
and fifthly, concentrating and deodorizing the isopropyl alcohol decolorized solution obtained in the fourth step to obtain 7.4g of cannabidiol-enriched oil paste.
Comparative example 4
Crushing 230g of sun-dried cannabis sativa leaves to 40 meshes, and heating and drying in a baking oven at 130 ℃ for 1h;
step two, adding 200g of the hemp leaves in the step one into 1% water, granulating to form solid particles, extracting by using 1000ml of 70% methanol with the volume being 5 times of that of the solid particles, filtering the extracting solution, and concentrating the extracting solution to the residual 100ml;
step three, adding 300ml of petroleum ether solvent into the concentrated solution obtained by the treatment in the step two for liquid-liquid extraction;
step four, separating out the petroleum ether layer obtained after the treatment in the step three, adding 3g of wood activated carbon, stirring for 10min, and filtering to obtain clear transparent feed liquid;
and fifthly, concentrating and deodorizing the decolorized solution obtained in the fourth step to obtain 21.5g of cannabidiol-enriched oil paste.
Comparative example 5
Crushing 120g of sun-dried cannabis sativa leaves to 50 meshes, and heating and drying in a baking oven at 130 ℃ for 1h;
step two, 100g of the hemp leaves in the step one are added with 1% of water and then granulated to form solid particles, 500ml of solvent of 5 times of volume of normal hexane is used for extraction according to the proportion, and the extracting solution is filtered and concentrated to the residual 60ml;
step three, adding 3g of wood activated carbon into the concentrated extract obtained in the step two, stirring for 10min, and filtering;
and step four, concentrating and deodorizing the decolorized solution obtained in the step three to obtain 15.0g of cannabidiol-enriched oil paste.
Influence of the extraction process on the cannabidiol content of the extracted product:
the cannabidiol oil pastes described in examples and comparative examples were subjected to content measurement, and the content data are shown in the following table.
TABLE 1 Experimental data for examples 1-3 and comparative examples 1-5
As can be seen from the above table, the cannabidiol ointment obtained in the examples has high cannabidiol content and low tetrahydrocannabinol content, while the cannabidiol ointment obtained in the comparative examples has low cannabidiol content and high tetrahydrocannabinol content, which means that impurities in the extract can be removed greatly by adjusting the extractant and the extractant of the present application, the cannabidiol content is improved, and part of tetrahydrocannabinol is removed at the same time, thereby providing a high quality raw material for further refining cannabidiol.
In addition, it can be seen that the yield of cannabidiol obtained by final extraction is higher by using 40-60 mesh cannabis sativa leaf raw material than 10-30 mesh cannabis sativa leaf raw material.
Claims (7)
1. An extraction method for extracting cannabidiol by using 40-60 mesh cannabis sativa leaves as raw materials is characterized by comprising the following steps:
step one, preparing materials, namely drying the hemp leaves with 40-60 meshes in an environment of 100-150 ℃;
step two, extracting the dried cannabis sativa leaves in the step one by a solvent, concentrating the extracting solution until a certain amount of extracting solvent remains, wherein the extracting solvent is one or a mixture of more than two of n-hexane, petroleum ether and vegetable oil extracting solvents;
step three, adding other solvents into the concentrated solution obtained in the step two for extraction, wherein the extraction solvent is one or more than two of 60-75% of methanol, ethanol, amyl alcohol, butanol and isopropanol;
step four, separating out the lower layer liquid treated in the step three, and adding activated carbon to stir and decolor;
and fifthly, concentrating the decolorized solution obtained in the fourth step, and deodorizing to obtain the cannabidiol-enriched ointment.
2. The extraction method according to claim 1, characterized in that: in the second step, the mass/volume ratio of the hemp flowers to the extraction solvent is 1g:4 mL-8 mL; concentrating the extractive solution to 1/5-1/15 of the original solvent volume.
3. The extraction method according to claim 2, characterized in that: in the third step, the volume ratio of the concentrated solution to the extraction solvent is 1:2-6, and after the concentrated solution and the extraction solvent are added, stirring is carried out for 10-30 min, and standing is carried out for 60-120 min, so that the two-phase solvent is completely separated.
4. The extraction method according to claim 3, characterized in that: the extraction agent used in the three steps is preferably 60% -75% of methanol and ethanol.
5. The extraction method according to claim 4, wherein: and in the fourth step, the added mass of the activated carbon is 0.1-3% g/ml of the volume of the lower layer liquid.
6. The extraction method according to claim 5, characterized in that: and step two, granulating the hemp leaves and then extracting.
7. The extraction method according to claim 6, characterized in that: and step four, the activated carbon is wood porous activated carbon, and the treatment time is 5-10 minutes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011117895.9A CN114380666B (en) | 2020-10-19 | 2020-10-19 | Industrial extraction method of cannabidiol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011117895.9A CN114380666B (en) | 2020-10-19 | 2020-10-19 | Industrial extraction method of cannabidiol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114380666A CN114380666A (en) | 2022-04-22 |
| CN114380666B true CN114380666B (en) | 2024-01-26 |
Family
ID=81193658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202011117895.9A Active CN114380666B (en) | 2020-10-19 | 2020-10-19 | Industrial extraction method of cannabidiol |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114380666B (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106831353A (en) * | 2016-08-16 | 2017-06-13 | 云南汉素生物科技有限公司 | A kind of method that cannabidiol is extracted from hemp |
| CN107898826A (en) * | 2017-11-01 | 2018-04-13 | 云南谷益美农业开发有限公司 | The preparation method of the numb medicinal extract of fire containing cannabidiol |
| CN109232191A (en) * | 2018-08-20 | 2019-01-18 | 润贝（安徽）饮料食品有限公司 | A method of extracting cannabidiol in industrial hemp leaf |
| CN110283048A (en) * | 2019-06-28 | 2019-09-27 | 云南翰谷生物科技有限公司 | The preparation method of cannabidiol crystal |
| CN110655453A (en) * | 2019-11-26 | 2020-01-07 | 云南绿新生物药业有限公司 | Extraction and separation method of hypocannabidiol |
| 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 |
-
2020
- 2020-10-19 CN CN202011117895.9A patent/CN114380666B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106831353A (en) * | 2016-08-16 | 2017-06-13 | 云南汉素生物科技有限公司 | A kind of method that cannabidiol is extracted from hemp |
| CN107898826A (en) * | 2017-11-01 | 2018-04-13 | 云南谷益美农业开发有限公司 | The preparation method of the numb medicinal extract of fire containing cannabidiol |
| CN109232191A (en) * | 2018-08-20 | 2019-01-18 | 润贝（安徽）饮料食品有限公司 | A method of extracting cannabidiol in industrial hemp leaf |
| CN110283048A (en) * | 2019-06-28 | 2019-09-27 | 云南翰谷生物科技有限公司 | The preparation method of cannabidiol crystal |
| CN110655453A (en) * | 2019-11-26 | 2020-01-07 | 云南绿新生物药业有限公司 | Extraction and separation method of hypocannabidiol |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN114380666A (en) | 2022-04-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102976909B (en) | Method for extracting and purifying 6-gingerol from ginger | |
| WO2020228786A1 (en) | Industrialized method for rapidly and efficiently extracting xanthophyll and quercetagetin | |
| CN111960930A (en) | Method for separating and purifying cannabidiol from industrial cannabis sativa leaves | |
| CN106349324B (en) | The method of extraction separation crataegolic acid from olive growing leaves | |
| CN112010738B (en) | Industrial method for producing cannabinoid compound by utilizing chromatographic separation | |
| CN108586306B (en) | Method for separating lutein and zeaxanthin by adopting ionic liquid enhanced extraction | |
| CN113754518A (en) | Method for efficiently purifying cannabidiol from industrial cannabis sativa leaves | |
| CN110613739A (en) | Method for separating flavonoid compounds in cotton rose based on high-speed countercurrent chromatography | |
| WO2022052394A1 (en) | Method for preparing delphinidin acylated anthocyanin | |
| CN113801003B (en) | Industrial extraction method of cannabidiol | |
| CN111171104B (en) | Method for preparing ursolic acid from rosemary oil paste by-product | |
| CN114380666B (en) | Industrial extraction method of cannabidiol | |
| CN115260005B (en) | Method for purifying and extracting cannabidiol and application thereof | |
| CN114989171B (en) | Efficient production process of tabersonine hydrochloride | |
| CN102199159B (en) | Method for separating and purifying ginkgolide C in ginkgo root bark | |
| CN108084241B (en) | The method that separation prepares fucosterol from sargassum fusifome | |
| CN111808066B (en) | Extraction method of schisandrin B extract | |
| CN109534979A (en) | A kind of isolation and purification method and production method of 6-gingerol | |
| CN105030891B (en) | preparation method and application of dracocephalum heterophyllum flavonoid component | |
| CN107098838A (en) | A kind of preparation method of garlic 4,5,9-trithiadodeca-1,6,11-triene 9-oxide reference substance | |
| CN115583983B (en) | Method for preparing high-purity crataegolic acid through separation | |
| CN115010690B (en) | Preparation method of high-purity cannabinol crystal | |
| CN1112410C (en) | Method for extracting solapurpurin | |
| CN109498686B (en) | Preparation method of triterpenic acid in jujube material | |
| CN1331859C (en) | Separation of taxinol from cephalotaxin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |