CN110467521A - It is a kind of using industrial hemp as cannabidiol (CBD) isolation and purification method of raw material - Google Patents

It is a kind of using industrial hemp as cannabidiol (CBD) isolation and purification method of raw material Download PDF

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Publication number
CN110467521A
CN110467521A CN201910780051.3A CN201910780051A CN110467521A CN 110467521 A CN110467521 A CN 110467521A CN 201910780051 A CN201910780051 A CN 201910780051A CN 110467521 A CN110467521 A CN 110467521A
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cbd
concentrated
concentrate
cannabidiol
industrial hemp
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王振宇
张华�
张胜宇
李�杰
辛超
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Harbin Institute of Technology
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Harbin Institute of Technology
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/685Processes comprising at least two steps in series
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/70Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
    • C07C37/82Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by solid-liquid treatment; by chemisorption
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Abstract

The present invention relates to a kind of using industrial hemp as the isolation and purification method of the cannabidiol (CBD) of raw material.The isolation and purification method of the cannabidiol includes: using industrial hemp plant upper end 1/3 using blade as raw material, tunnel type ultrasonic wave and heating combination extraction obtain extracting solution, it is concentrated in economic benefits and social benefits tribe Cimicifugeae tank, the sedimentation removal supernatant in agitator tank, precipitated liquid crosses the level-one of macroreticular resin LSA -12 chromatography, excessively symmetrical spherical silica gel second level chromatography after concentration, by preparative efficient liquid phase after concentration, after eluent concentration, crystallization, the CBD that purity is 90~99.9% can get.Compared with prior art, CBD purity is high prepared by the present invention, yield is high, and simple process and low cost, is easy to industrialization.

Description

It is a kind of using industrial hemp as cannabidiol (CBD) isolation and purification method of raw material
Technical field
The invention belongs to field of medicine and chemical technology, and in particular to a kind of using industrial hemp as the cannabidiol (CBD) of raw material Isolation and purification method.
Background technique
Hemp (Cannabis sativa L.) is the annual herb plant of Cannabaceae Cannabis, is had all over the world point Cloth.Cannabis seeds are rich in good protein and unsaturated fatty acid, can be used as food, health care product and feed, the work in flower, leaf Property substance be widely used in medicine and cosmetic field.Cannboid is distinctive time containing alkyl and monoterpene group in hemp plant Raw metabolin.Isolated hemp is known as more than 70 kinds in cannabis plants, mainly includes THC (tetrahydrocannabinol), CBD (cannabidiol), CBC (cannabichromene), CBN (cannabinol), CBG (cannabigerol) and its propyl homologue etc., wherein THC and CBD isomer each other, content highest.CBD is in the protection of antitumor, nervous system, immunological regulation and anti-inflammatory anti- Oxidation etc. has medical value.
2018, CBD product E pidiolex was included in subordinate list V and (it is relatively low to abuse risk by United States drug Surveillance Authority Drug), Epidiolex is by food and drug administration (FDA) approval for treating the drug resistance epilepsy of two kinds of forms (Lennox Gastaut and Dravet syndrome).Cannabidiol is most isolated from hemp earlier than 1940, is in hemp Non- spiritual constituents, no hallucinogenic action.Preclinical laboratory shows that CBD has apparent anti-epileptic and anti-convulsant activity, and Adverse reaction is less than existing antiepileptic.But phenols component is complicated in cannabis plant, easily extracts polarity similar component, influences Product Safety.
Present invention improves over the extraction processes of cannabidiol in the prior art, after CBD crude extract is concentrated, carry out I and II chromatography and preparative liquid phase separation, optimize medium, path length ratio, the conditions such as eluent and applied sample amount greatly improved The purity of CBD, simple process and low cost are easy to industrialization.
Summary of the invention
The present invention is as follows as the isolation and purification method of the cannabidiol (CBD) of raw material using industrial hemp:
1. extraction: taking industrial hemp plant upper end 1/3 with blade, be put into tunnel type counter current ultrasonic wave and set with heating combination extraction It is standby, solvent is made with dehydrated alcohol, methanol, solid-liquid ratio 1:4~1:6,3000~5000W of ultrasonic power, 80~95 DEG C of extraction temperature, Extraction time 2~3 hours, obtain industrial hemp CBD extracting solution.
2. concentration: extract liquor is put into economic benefits and social benefits tribe Cimicifugeae tank, is concentrated, vacuum degree 0.075MaP, temperature 90~ 95 DEG C, it is concentrated into 1st/16th~20 of extract liquor volume, obtains CBD concentrate.
3. sedimentation: add CBD concentrate to be put into agitator tank, adds 30~60 times of water, be stirred, 30~40 points of mixing time Clock, stirring slurry revolving speed, 30~40 revs/min.Static 20~24 hours, supernatant is removed, obtains CBD precipitated liquid.
4. level-one chromatographs: chromatographic column path length ratio is 1:6~1:10, and chromatography media is macroreticular resin LSA -12.CBD is sunk After shallow lake liquid adds 5~8 times of methanol stirring and dissolvings, additional amount is the 15~30% of column volume.With 30~70% ethanol elution, eluent 2~4 column volumes of dosage.It is eluted again with dehydrated alcohol and methyl alcohol mixed liquor, collects chromatographic solution containing CBD.
5. concentration: CBD chromatographic solution is put into economic benefits and social benefits tribe Cimicifugeae tank, is concentrated, vacuum degree 0.075MaP, temperature 90 ~95 DEG C, it is concentrated into 1st/10th~15 of extract liquor volume, obtains CBD chromatography concentrate.
6. second level chromatographs: chromatographic column path length ratio is 1:6~1:10, and chromatography media is symmetrical spherical silica gel, and silica gel granularity is 200~400 mesh.After CBD chromatography concentrate is added 4~6 times of methanol stirring and dissolvings, chromatographic column is added, additional amount is column volume 15~30%.It is eluted with methylene chloride and n-hexane, collects the chromatographic solution of second level containing CBD.
7. concentration: CBD second level chromatographic solution is put into economic benefits and social benefits tribe Cimicifugeae tank, is concentrated, vacuum degree 0.075 ~ 0.09MaP, is concentrated into 1st/6th~10 of extract liquor volume by 90~95 DEG C of temperature, obtains high-purity C BD concentrate, and purity is reachable 60~80%.
8. preparative efficient liquid phase separates: splitter path length ratio 1:2~1:4, separating medium are symmetrical spherical silica gel and C18 Mixture, granular size are 200~400 mesh.High-pressure column is added after the high-purity concentrate of CBD is added 3~6 times of methanol stirrings, uses first Alcohol and n-butanol elute, and pressure is 10 ~ 30 megapascal, collect CBD efficient liquid phase eluent, after concentration, crystallization, available purity is 90~99.9% CBD.
Specific embodiment
Below with reference to specific implementation example, the present invention is further explained.
Embodiment 1
1. extraction: it takes industrial hemp plant upper end 1/3 with blade, is put into tunnel type ultrasonic wave and heating combination extraction equipment, Solvent is made with dehydrated alcohol, solid-liquid ratio 1:4, ultrasonic power 5000W, extraction time 3 hours, are obtained industrial big by 80 DEG C of extraction temperature Numb CBD extracting solution.
2. concentration: extract liquor is put into economic benefits and social benefits tribe Cimicifugeae tank, is concentrated, vacuum degree 0.075MaP, 95 DEG C of temperature, It is concentrated into the 1/20 of extract liquor volume, obtains CBD concentrate.
3. sedimentation: add CBD concentrate to be put into agitator tank, adds 30 times of water, be stirred, mixing time 40 minutes, stirring Slurry revolving speed, 30 revs/min.Static 24 hours, supernatant is removed, obtains CBD precipitated liquid.
4. level-one chromatographs: chromatographic column path length ratio is 1:6, and chromatography media is macroreticular resin LSA -12.CBD precipitated liquid is added 8 After times methanol stirring and dissolving, additional amount is the 15% of column volume.With 30~70% ethanol elution, 4 column volumes of eluent dosage. It is eluted again with dehydrated alcohol and methyl alcohol mixed liquor, collects chromatographic solution containing CBD.
5. concentration: CBD chromatographic solution is put into economic benefits and social benefits tribe Cimicifugeae tank, is concentrated, vacuum degree 0.075MaP, temperature 90 DEG C, it is concentrated into the 1/10 of extract liquor volume, obtains CBD chromatography concentrate.
6. second level chromatograph: chromatographic column path length ratio be 1:6, chromatography media be symmetrical spherical silica gel, silica gel granularity be 200~ 400 mesh.After CBD chromatography concentrate is added 4~6 times of methanol stirring and dissolvings, chromatographic column is added, additional amount is the 15% of column volume.With Methylene chloride and n-hexane elution, collect the chromatographic solution of second level containing CBD.
7. concentration: CBD second level chromatographic solution is put into economic benefits and social benefits tribe Cimicifugeae tank, is concentrated, vacuum degree 0.075 ~ 0.09MaP, is concentrated into the 1/10 of extract liquor volume by 90 DEG C of temperature, obtains high-purity C BD concentrate, purity is up to 60~80%.
8. preparative efficient liquid phase separates: splitter path length ratio 1:2, separating medium are that symmetrical spherical silica gel is mixed with C18 Object, granular size are 200~400 mesh.High-pressure column is added after the high-purity concentrate of CBD is added 3 times of methanol stirrings, with methanol and positive fourth Alcohol elution, pressure be 10 ~ 30 megapascal, collect CBD efficient liquid phase eluent, concentration, crystallization after, can get purity be 90~ 99.9% CBD.
Embodiment 2
1. extraction: it takes industrial hemp plant upper end 1/3 with blade, is put into tunnel type ultrasonic wave and heating combination extraction equipment, Solvent is made with methanol, solid-liquid ratio 1:5, ultrasonic power 3000W, extraction time 2 hours, obtain industrial hemp CBD by 95 DEG C of extraction temperature Extracting solution.
2. concentration: extract liquor is put into economic benefits and social benefits tribe Cimicifugeae tank, is concentrated, vacuum degree 0.075MaP, 95 DEG C of temperature, It is concentrated into 1/the 1/16 of extract liquor volume, obtains CBD concentrate.
3. sedimentation: add CBD concentrate to be put into agitator tank, adds 60 times of water, be stirred, mixing time 30 minutes, stirring 40 revs/min of revolving speed of slurry.Static 24 hours, supernatant is removed, obtains CBD precipitated liquid.
4. level-one chromatographs: chromatographic column path length ratio is 1:8, and chromatography media is macroreticular resin LSA -12.CBD precipitated liquid is added 5 After times methanol stirring and dissolving, additional amount is the 30% of column volume.With 30~70% ethanol elution, 3 column volumes of eluent dosage. It is eluted again with dehydrated alcohol and methyl alcohol mixed liquor, collects chromatographic solution containing CBD.
5. concentration: CBD chromatographic solution is put into economic benefits and social benefits tribe Cimicifugeae tank, is concentrated, vacuum degree 0.075MaP, temperature 90 ~95 DEG C, it is concentrated into the 1/15 of extract liquor volume, obtains CBD chromatography concentrate.
6. second level chromatograph: chromatographic column path length ratio be 1:10, chromatography media be symmetrical spherical silica gel, silica gel granularity be 200~ 400 mesh.After CBD chromatography concentrate is added 6 times of methanol stirring and dissolvings, chromatographic column is added, additional amount is the 30% of column volume.With two Chloromethanes and n-hexane elution, collect the chromatographic solution of second level containing CBD.
7. concentration: CBD second level chromatographic solution is put into economic benefits and social benefits tribe Cimicifugeae tank, is concentrated, vacuum degree 0.075 ~ 0.09MaP, is concentrated into the 1/8 of extract liquor volume by 90 DEG C of temperature, obtains high-purity C BD concentrate, purity is up to 60~80%.
8. preparative efficient liquid phase separates: splitter path length ratio 1:4, separating medium are that symmetrical spherical silica gel is mixed with C18 Object, granular size are 200~400 mesh.High-pressure column is added after the high-purity concentrate of CBD is added 6 times of methanol stirrings, with methanol and positive fourth Alcohol elution, pressure be 10 ~ 30 megapascal, collect CBD efficient liquid phase eluent, concentration, crystallization after, can get purity be 90~ 99.9% CBD.
Embodiment 3
1. extraction: it takes industrial hemp plant upper end 1/3 with blade, is put into tunnel type ultrasonic wave and heating combination extraction equipment, Solvent is made with dehydrated alcohol and methanol, solid-liquid ratio 1:6, ultrasonic power 4000W, extraction time 3 hours, are obtained by 90 DEG C of extraction temperature Industrial hemp CBD extracting solution.
2. concentration: extract liquor is put into economic benefits and social benefits tribe Cimicifugeae tank, is concentrated, vacuum degree 0.075MaP, 95 DEG C of temperature, It is concentrated into the 1/20 of extract liquor volume, obtains CBD concentrate.
3. sedimentation: add CBD concentrate to be put into agitator tank, adds 50 times of water, be stirred, mixing time 40 minutes, stirring Slurry revolving speed, 30 revs/min.Static 20 hours, supernatant is removed, obtains CBD precipitated liquid.
4. level-one chromatographs: chromatographic column path length ratio is 1:10, and chromatography media is macroreticular resin LSA -12.CBD precipitated liquid is added After 6 times of methanol stirring and dissolvings, additional amount is the 25% of column volume.With 30~70% ethanol elution, 2 cylinders of eluent dosage Product.It is eluted again with dehydrated alcohol and methyl alcohol mixed liquor, collects chromatographic solution containing CBD.
5. concentration: CBD chromatographic solution is put into economic benefits and social benefits tribe Cimicifugeae tank, is concentrated, vacuum degree 0.075MaP, temperature 90 ~95 DEG C, it is concentrated into the 1/12 of extract liquor volume, obtains CBD chromatography concentrate.
6. second level chromatograph: chromatographic column path length ratio be 1:8, chromatography media be symmetrical spherical silica gel, silica gel granularity be 200~ 400 mesh.By CBD chromatography concentrate add 4~6 times of methanol stirring and dissolvings after, be added chromatographic column, additional amount be column volume 15~ 30%.It is eluted with methylene chloride and n-hexane, collects the chromatographic solution of second level containing CBD.
7. concentration: CBD second level chromatographic solution is put into economic benefits and social benefits tribe Cimicifugeae tank, is concentrated, vacuum degree 0.075 ~ 0.09MaP, is concentrated into the 1/8 of extract liquor volume by 95 DEG C of temperature, obtains high-purity C BD concentrate, purity is up to 60~80%.
8. preparative efficient liquid phase separates: splitter path length ratio 1:3, separating medium are that symmetrical spherical silica gel is mixed with C18 Object, granular size are 200~400 mesh.High-pressure column is added after the high-purity concentrate of CBD is added 5 times of methanol stirrings, with methanol and positive fourth Alcohol elution, pressure be 10 ~ 30 megapascal, collect CBD efficient liquid phase eluent, concentration, crystallization after, can get purity be 90~ 99.9% CBD.
The above is the preferable embodiment of the present invention, and only demonstration is used, the substantive skill being not intended to limit the present invention Art context.It is said in text identical as meaning known to those skilled in the art with technical term.Any those skilled in the art The description of formula according to the present invention and its preferred embodiment, the various products made belong to equivalent and change or replace.

Claims (4)

1. a kind of using industrial hemp as the isolation and purification method of the cannabidiol (CBD) of raw material, comprising the following steps:
(1) it extracts: taking industrial hemp plant upper end 1/3 with blade, be put into tunnel type counter current ultrasonic wave and heating combination extraction Equipment does solvent, solid-liquid ratio 1:4~1:6,3000~5000W of ultrasonic power, extraction temperature 80~95 with dehydrated alcohol, methanol DEG C, extraction time 2~3 hours, industrial hemp CBD extracting solution is obtained,
(2) it is concentrated: extract liquor being put into economic benefits and social benefits tribe Cimicifugeae tank, is concentrated, vacuum degree 0.075MaP, temperature 90~95 DEG C, it is concentrated into 1st/16th~20 of extract liquor volume, obtains CBD concentrate,
(3) it settles: adding CBD concentrate to be put into agitator tank, add 30~60 times of water, be stirred, mixing time 30~40 minutes, Stirring slurry revolving speed, static 20~24 hours, supernatant is removed, obtains CBD precipitated liquid by 30~40 revs/min,
(4) level-one chromatographs: chromatographic column path length ratio is that 1:6~1:10 adds after CBD precipitated liquid is added 5~8 times of methanol stirring and dissolvings Enter 15~30% that amount is column volume;With 30~70% ethanol elution, 2~4 column volumes of eluent dosage, then use dehydrated alcohol It is eluted with methyl alcohol mixed liquor, collects chromatographic solution containing CBD,
(5) it is concentrated: CBD chromatographic solution being put into economic benefits and social benefits tribe Cimicifugeae tank, is concentrated, vacuum degree 0.075MaP, temperature 90~ 95 DEG C, it is concentrated into 1st/10th~15 of extract liquor volume, obtains CBD chromatography concentrate,
(6) second level chromatographs: chromatographic column path length ratio is 1:6~1:10, and chromatography media is symmetrical spherical silica gel, and silica gel granularity is 200 ~400 mesh, by CBD chromatography concentrate add 4~6 times of methanol stirring and dissolvings after, be added chromatographic column, additional amount be column volume 15~ 30%, the chromatographic solution of second level containing CBD is collected in elution,
(7) it is concentrated: CBD second level chromatographic solution being put into economic benefits and social benefits tribe Cimicifugeae tank, is concentrated, 0.075 ~ 0.09MaP of vacuum degree, 90~95 DEG C of temperature, be concentrated into 1st/6th~10 of extract liquor volume, obtain high-purity C BD concentrate, purity up to 60~80%,
(8) preparative efficient liquid phase separates: splitter path length ratio 1:2~1:4, and separating medium is that symmetrical spherical silica gel and C18 are mixed Object is closed, granular size is 200~400 mesh, and high-pressure column is added after the high-purity concentrate of CBD is added 3~6 times of methanol stirrings, uses methanol It is eluted with n-butanol, pressure is 10 ~ 30 megapascal, and collecting CBD efficient liquid phase eluent can get CBD after concentration, crystallization.
2. special according to a kind of using industrial hemp as the isolation and purification method of the cannabidiol (CBD) of raw material described in claim 1 Sign is cannabidiol concentrate purity up to 90~99.9%.
3. special according to a kind of using industrial hemp as the isolation and purification method of the cannabidiol (CBD) of raw material described in claim 1 Sign is that level-one chromatography media is macroreticular resin LSA -12.
4. special according to a kind of using industrial hemp as the isolation and purification method of the cannabidiol (CBD) of raw material described in claim 1 Sign is that second level chromatography uses methylene chloride and n-hexane as eluent.
CN201910780051.3A 2019-08-22 2019-08-22 It is a kind of using industrial hemp as cannabidiol (CBD) isolation and purification method of raw material Pending CN110467521A (en)

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CN113004125A (en) * 2019-12-20 2021-06-22 浙江华谱新创科技有限公司 Purification preparation method of high-purity CBD cannabidiol
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