CN110229135A - The method of chromatography production high-purity tetrahydrocannabinol - Google Patents
The method of chromatography production high-purity tetrahydrocannabinol Download PDFInfo
- Publication number
- CN110229135A CN110229135A CN201910619293.4A CN201910619293A CN110229135A CN 110229135 A CN110229135 A CN 110229135A CN 201910619293 A CN201910619293 A CN 201910619293A CN 110229135 A CN110229135 A CN 110229135A
- Authority
- CN
- China
- Prior art keywords
- tetrahydrocannabinol
- purity
- hemp
- solvent
- ethyl acetate
- 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.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
Abstract
The invention discloses a kind of methods of chromatography production high-purity tetrahydrocannabinol.Described method includes following steps: 1) using solvent extraction hemp, obtain extract liquor, then carry out liquid chromatogram separation；The efflux of the 4th~7 times of column volume is collected, as containing the solution of tetrahydrocannabinol；2) efflux successively arrives the tetrahydrocannabinol of high-purity through solvent removal.The present invention is a kind of method of the tetrahydrocannabinol purity using the floral leaf stem of hemp as raw material, extracted greater than 98%, and the method achieve the large-scale industrial productions of high-purity tetrahydrocannabinol, effectively solves demand of the market to high-purity tetrahydrocannabinol product.
Description
Technical field
The present invention relates to a kind of methods of chromatography production high-purity tetrahydrocannabinol.
Background technique
Hemp originates in India, Iran, the Himalayas to a Siberia generation and China.It is used to cure in a variety of manners
Medicine, religion, ceremony and existing thousands of years of the history of amusement.By medicine using for many years, it is used as hypnosis sedative and controls hemp
Treat hysteria, paranoea, epilepsy, nerve insomnia, migraines, the diseases such as pain and dysmenorrhea.In history, many doctors think
Hemp is unique.The use of hemp is continued until the twentieth century middle period.As most of traditional drugs, hemp is very
Long following period of time be completely it is legal is even encouraged or even is forced plant.Purposes of largely lying fallow at that time, which facilitates, to be forbidden making
With the legislation of hemp.Currently, as that studies hemp component gos deep into, it is more and more clear to the clinical effectiveness of hemp, reasonable
Use condition under, fully demonstrated hemp to some diseases treatment and the important function that is played of health, these researchs
Achievement also causes some countries and regions to gradually relax control the control to hemp and products thereof, it is allowed to be used as medicine, health care product, joy
Happy product use.
Cannboid ingredient present in hemp is tetrahydro-cannabinolic acid (tetrahydrocannabinolic acid
THCA), tetrahydrocannabinol (tetrahydrocannabinol, THC), cannboid (cannabinol, CBN), cannabidiol
(caimabidiol, CBD), cannabigerol (caimabigerol, CBG), cannabichromene (cannabichromene, CBC),
Cannabigerol ester (CBGM) and THCV etc..Mainly there are 3 kinds, CBN, CBD, THC, especially THC, including 9- in cannabinoids
Trans- THC, 8-THC are trans- etc..Recent studies suggest that different cannabinoid 1 activity ingredients has different effects, different diseases is treated
Disease.And THC is the main active in hemp floral leaf, there is very high medical value.Currently, having no in the world high-purity
The production report of THC is spent, also the not no THC product supply market of high-purity, to limit the development and utilization of the product.
Summary of the invention
The object of the present invention is to provide a kind of method of chromatography production high-purity tetrahydrocannabinol (THC), prepared THC is produced
The purity of product can carry out industrialized production up to 98% or more.
The method of chromatography production high-purity tetrahydrocannabinol provided by the present invention, includes the following steps:
1) solvent extraction hemp is used, extract liquor is obtained, then carries out liquid chromatogram separation；Collect the 4th~7 times of column volume
Efflux, as containing the solution of tetrahydrocannabinol；
2) efflux successively arrives the tetrahydrocannabinol of high-purity through solvent removal.
In above-mentioned method, using the floral leaf stem of hemp as raw material, moisture content is crushed less than 8% as granularity
Less than carrying out the extraction after 0.1mm.
In above-mentioned method, in step 1), the solvent can be methanol, ethyl alcohol, ethylene glycol, acetone, ethyl acetate, penta
It is any in alkane, n-hexane, heptane and petroleum ether, preferred alcohol, pentane or heptane；
The dosage of the solvent are as follows: hemp described in 6~8L/kg.
In above-mentioned method, in step 1), the condition of the liquid chromatogram separation is as follows:
Filler be solid phase chromatography filler that styrene diethylene benzene copoly mer is material (its granularity is 150~200 mesh,
Aperture is 0.1~0.15nm) or C18；
Chromatographic column can be the stainless steel column of ratio of height to diameter 8:1, and volume can be 400L；
Mobile phase is mixed liquor or heptane and acetic acid at least two kinds of in water, methanol, ethyl alcohol, acetone, ethyl acetate and acetonitrile
The mixed liquor of ethyl ester；
Isocratic elution；
Flowing velocity is 2~3 times of column volume.
In above-mentioned method, in step 2), the solvent removal in single-action concentration tank, Multi-effect concentration tank and film machine at least
It is carried out in one kind, the combination of preferably described film machine and the single-effect concentrator, obtains high-purity THC after removing solvent.
The present invention is a kind of using industrial hemp or the floral leaf stem of other hemps as raw material, and the tetrahydrocannabinol extracted is pure
Degree is greater than 98% method, and the method achieve the large-scale industrial productions of high-purity tetrahydrocannabinol, effectively solution market
Demand to high-purity tetrahydrocannabinol product.
Detailed description of the invention
Fig. 1 is the flow chart that chromatography of the present invention produces high-purity tetrahydrocannabinol method.
Specific embodiment
Experimental method used in following embodiments is conventional method unless otherwise specified.
The materials, reagents and the like used in the following examples is commercially available unless otherwise specified.
The condition of chromatographic isolation is as follows in following embodiments:
Filler is the solid phase chromatography filler that styrene diethylene benzene copoly mer is material, and granularity is 150-200 mesh,
Aperture is 0.1-0.15nm.
Chromatographic column is the stainless steel column of ratio of height to diameter 8:1, volume 400L；
Temperature is 15~25 DEG C.
The purity of THC measures by the following method in following embodiments:
Agilent high pressure liquid chromatograph, model 1220；
Chromatographic column: EXTEND-C-18 4.6*250mm 5um；
Mobile phase: acetonitrile: phosphate aqueous solution=70:30；
Detection wavelength: 220nm；
Flow velocity: 1.1ml/min；
Column temperature: 35 DEG C.
Embodiment 1,
Flow chart is as shown in Figure 1.
Step 1: use pulverizer that raw material is crushed to 0.1 millimeter hereinafter, using cannabis base of leaf as raw material, water content
Less than 8%.
Step 2: in 200 kilograms of raw material primary loading solvent extraction equipments of crushing, with 8 times of bulking values (L/kg)
90% ethanol water extracted, collect the second containing tetrahydrocannabinol and other cannabinoids that flows out out of extraction equipment
Alcohol extract liquor.
Step 3: alcohol extraction liquid is deployed into water aqueous 30% solution, it is filtered to remove insoluble matter, clear liquid is beaten with pump
Enter in chromatographic system, eluted using the solution (volume content) of 80% ethanol water as mobile phase, Fractional Collections from point
From the mobile phase flowed out in system, the efflux of preceding 3 times of column volumes is impurity, and the 4th~7 times is the solution containing tetrahydrocannabinol.
Step 4: recycling ethyl alcohol, the second of recycling containing tetrahydrocannabinol ethanol water film machine what third step obtained
Alcohol is reused；Remove the concentrate obtained after 90% or more ethyl alcohol by film machine to enter in single-effect concentrator, removing is surplus
Remaining solvent obtains tetrahydrocannabinol oil product.
The purity of tetrahydrocannabinol is 95% in tetrahydrocannabinol oil product obtained by the present embodiment.
Embodiment 2,
Flow chart is as shown in Figure 1.
Step 1: use pulverizer that raw material is crushed to 0.1 millimeter hereinafter, using cannabis base of leaf as raw material, water content
Less than 8%.
Step 2: in 200 kilograms of raw material primary loading solvent extraction equipments of crushing, with 8 times of bulking values (L/kg)
Heptane extracted, collect flowed out out of extraction equipment containing the ethyl alcohol of tetrahydrocannabinol and other cannabinoids extract
Liquid.
Step 3: heptane extraxtion liquid pump is squeezed into chromatographic system, using ethyl acetate: heptane=1:10 (volume) is molten
Liquid is eluted as mobile phase, the mobile phase that Fractional Collections are flowed out out of separation system, and the efflux of preceding 3 times of column volumes is miscellaneous
Matter, the 4th~7 times is the solution containing tetrahydrocannabinol.
Step 4: the solution containing tetrahydrocannabinol that third step is obtained is concentrated, the oil of tetrahydrocannabinol is obtained
Product.
The purity of tetrahydrocannabinol is 95% in tetrahydrocannabinol oil product obtained by the present embodiment.
Claims (5)
1. a kind of method of chromatography production high-purity tetrahydrocannabinol, includes the following steps:
1) solvent extraction hemp is used, extract liquor is obtained, then carries out liquid chromatogram separation；Collect the stream of the 4th~7 times of column volume
Liquid out, as containing the solution of tetrahydrocannabinol；
2) efflux successively arrives the tetrahydrocannabinol of high-purity through solvent removal.
2. according to the method described in claim 1, it is characterized by: using the floral leaf stem of hemp as raw material, moisture content
Less than 8%, is crushed and carry out the extraction after being less than 0.1mm for granularity.
3. method according to claim 1 or 2, it is characterised in that: in step 1), the solvent is methanol, ethyl alcohol, second two
It is any in alcohol, acetone, ethyl acetate, pentane, n-hexane, heptane and petroleum ether；
The dosage of the solvent are as follows: hemp described in 6~8L/kg.
4. any one of -3 the method according to claim 1, it is characterised in that: in step 1), the liquid chromatogram separation
Condition is as follows:
Filler is the solid phase chromatography filler or C18 that styrene diethylene benzene copoly mer is material；
Mobile phase is the mixing of at least two kinds of or heptane and ethyl acetate in water, methanol, ethyl alcohol, acetone, ethyl acetate and acetonitrile
Liquid.
5. any one of -4 the method according to claim 1, it is characterised in that: in step 2), the solvent removal is in single-action
It is carried out at least one of concentration tank, Multi-effect concentration tank and film machine.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910619293.4A CN110229135A (en) | 2019-07-10 | 2019-07-10 | The method of chromatography production high-purity tetrahydrocannabinol |
| CN201910837374.1A CN110922376A (en) | 2019-07-10 | 2019-09-05 | Method for producing high-purity tetrahydrocannabinol by chromatography |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910619293.4A CN110229135A (en) | 2019-07-10 | 2019-07-10 | The method of chromatography production high-purity tetrahydrocannabinol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN110229135A true CN110229135A (en) | 2019-09-13 |
Family
ID=67854967
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910619293.4A Withdrawn CN110229135A (en) | 2019-07-10 | 2019-07-10 | The method of chromatography production high-purity tetrahydrocannabinol |
| CN201910837374.1A Pending CN110922376A (en) | 2019-07-10 | 2019-09-05 | Method for producing high-purity tetrahydrocannabinol by chromatography |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910837374.1A Pending CN110922376A (en) | 2019-07-10 | 2019-09-05 | Method for producing high-purity tetrahydrocannabinol by chromatography |
Country Status (1)
| Country | Link |
|---|---|
| CN (2) | CN110229135A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110668923A (en) * | 2019-11-13 | 2020-01-10 | 贵州航天乌江机电设备有限责任公司 | Extraction and separation method of high-purity cannabidiol |
| CN110746275A (en) * | 2019-11-08 | 2020-02-04 | 河南汉麻生物科技有限公司 | Method for separating cannabidiol by using continuous chromatographic system |
| CN113009049A (en) * | 2019-12-20 | 2021-06-22 | 浙江华谱新创科技有限公司 | Process for removing THC in full-spectrum hemp extract oil |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113828015A (en) * | 2020-06-24 | 2021-12-24 | 北京创新通恒科技有限公司 | Multi-column continuous separation equipment and process method for removing THC in hemp extract |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10051427C1 (en) * | 2000-10-17 | 2002-06-13 | Adam Mueller | Process for the production of an extract containing tetrahydrocannabinol and cannabidiol from cannabis plant material and cannabis extracts |
| EP1773801A1 (en) * | 2004-07-19 | 2007-04-18 | Cilag Ltd. | Method for obtaining pure tetrahydrocannabinol |
| CN206244694U (en) * | 2016-10-26 | 2017-06-13 | 谢爽 | The production equipment of high-purity cannabidiol |
| CN109568389B (en) * | 2017-09-29 | 2022-02-08 | 汉义生物科技（北京）有限公司 | Preparation method of high-purity cannabinol extract |
-
2019
- 2019-07-10 CN CN201910619293.4A patent/CN110229135A/en not_active Withdrawn
- 2019-09-05 CN CN201910837374.1A patent/CN110922376A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110746275A (en) * | 2019-11-08 | 2020-02-04 | 河南汉麻生物科技有限公司 | Method for separating cannabidiol by using continuous chromatographic system |
| CN110668923A (en) * | 2019-11-13 | 2020-01-10 | 贵州航天乌江机电设备有限责任公司 | Extraction and separation method of high-purity cannabidiol |
| CN113009049A (en) * | 2019-12-20 | 2021-06-22 | 浙江华谱新创科技有限公司 | Process for removing THC in full-spectrum hemp extract oil |
Also Published As
| Publication number | Publication date |
|---|---|
| CN110922376A (en) | 2020-03-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110229135A (en) | The method of chromatography production high-purity tetrahydrocannabinol | |
| US10662137B2 (en) | Method for preparing high-purity cannabidiol | |
| AU2002218242B2 (en) | Method for producing an extract from cannabis plant matter, containing a tetrahydrocannabinol and a cannabidiol and cannabis extracts | |
| CN110642679B (en) | Method for preparing cannabidiol and coproducing cannabis full spectrum oil | |
| US20190010106A1 (en) | Process for purification and separation of cannabinoids, from dried hemp and cannabis leaves | |
| CN106860492A (en) | A kind of preparation method of cannabinol compounds | |
| CN110330409A (en) | A kind of preparation method of industrial hemp extract | |
| CN109646992A (en) | The method of cannabidiol enriched substance is extracted from industrial hemp | |
| CN112010738B (en) | Industrial method for producing cannabinoid compound by utilizing chromatographic separation | |
| CN110304993A (en) | The method of chromatography production high-purity cannabidiol | |
| CN101254220A (en) | Production process of water soluble ginkgo leaf extractive | |
| CN111960930A (en) | Method for separating and purifying cannabidiol from industrial cannabis sativa leaves | |
| CN110467521A (en) | It is a kind of using industrial hemp as cannabidiol (CBD) isolation and purification method of raw material | |
| CN101982471B (en) | Technological process for extracting aucubin from fruits of eucommia ulmoides oliver | |
| CN104592324A (en) | Gastrodin extraction and purification method | |
| CN109851480A (en) | A method of high-purity cannabidiol is prepared using dynamic axial compression column | |
| CN110724589B (en) | Method for preparing cannabidiol and coproducing cannabis full spectrum oil | |
| CN103169788B (en) | Chinese date leaf extractive and application thereof in preparation of medicament or health food for preventing and treating liver injury | |
| CN104910112B (en) | A kind of preparation method, pharmaceutical preparation and the clinical practice of salviamiltiorrhizabung active ingredient tanshin polyphenolic acid B | |
| CN110143853A (en) | A kind of industrial production process of cannabidiol | |
| CN104000935B (en) | A kind of method that anti-oxidant phenolic acid is extracted in the slag from jacket | |
| CN101704729A (en) | Method for extracting resveratrol and polydatin in grape seeds | |
| CN103936816A (en) | Method for purifying tanshinone IIA in salvia miltiorrhiza crude extract through simulated moving bed chromatography | |
| CN112939742A (en) | Method for extracting and purifying cannabinoid | |
| CN111039760A (en) | Method for preparing phenolic compound |
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 | ||
| WW01 | Invention patent application withdrawn after publication | ||
| WW01 | Invention patent application withdrawn after publication |
Application publication date: 20190913 |