CN110511119A - A kind of extracting method of cannabidiol - Google Patents
A kind of extracting method of cannabidiol Download PDFInfo
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- CN110511119A CN110511119A CN201910746327.6A CN201910746327A CN110511119A CN 110511119 A CN110511119 A CN 110511119A CN 201910746327 A CN201910746327 A CN 201910746327A CN 110511119 A CN110511119 A CN 110511119A
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- cannabidiol
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/004—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from plant material or from animal material
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/82—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by solid-liquid treatment; by chemisorption
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/84—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by crystallisation
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- 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
Abstract
The present invention provides the extracting method of cannabidiol CBD a kind of, including repeatedly -100-196 DEG C of freezing 1-4h, heating are thawed to 40-60 DEG C；Subcritical Water Extraction；Chromatographic column elution, concentration；After ethyl alcohol is dissolved to supersaturation, crystal is precipitated, washing, drying crystallization are to get cannabidiol CBD product.The present invention can both extract dry work material, can also extract to fresh material, material wide adaptability, can continuous production.It is handled particularly by ultralow temperature breaking-wall cell, make fresh or dry material that fracture and broken wall can occur under the action of thermal stress, to efficiently extract effective component therein, avoid traditional enzymolysis process is unstable, enzymatic hydrolysis is insufficient from leading to broken wall low efficiency.Production process of the present invention is simple, and sporoderm-broken rate is high, it is entirely avoided the problem of effective component is lost in extraction process.
Description
Technical field
The present invention relates to a kind of extracting methods of cannabidiol, belong to field of biotechnology.
Background technique
Cannabidiol CBD is a kind of extract of industrial hemp, research shows that cannabidiol (CBD) have it is important medicinal
Value, shows well in fields such as epilepsy therapy, neuroprotection, multiple sclerosis, rheumatic arthritis, oncotherapies
Pharmacological activity, there is extraordinary application prospect, and do not have additive, CBD has a extensive future, but cannabidiol
There is many problems for extraction, and many extracting method recovery rates are high, but obtained cannabidiol purity is not high, it is difficult to reach extraction
Furthermore high, the with high purity cannabidiol of rate is mostly batch production in existing most production technology, it is more difficult to realize continuous metaplasia
It produces.
Since cannabidiol (Cannabidiol, CBD) has excellent natural activity and medical value, therefore from work
Cannabidiol (CBD) is extracted in sparetime university fiber crops to have a vast market foreground.Have in public information much about cannabidiol at present
(CBD) report of extracting method, most commonly used is solvent extraction method, and the dissolution added is cannabidiol dissolution mostly
High organic solvent, such as hexamethylene, methanol, methylene chloride, chloroform, petroleum ether are spent, although the recovery rate of cannabidiol is
It improves, but the use of organic solvent can not only endanger environment, and dissolvent residual is not divisible in finished product, Product Safety obtains
Less than guarantee；Except this supercritical carbon dioxide extraction technology is also introduced into recent years in cannabidiol extraction process, although having extraction
The advantages such as ability is strong, recovery rate is high, selectivity is strong, superior product quality, but there is also at high cost, energy consumption is high, is difficult to realize industry
The disadvantages of changing amplification production.Although its Subcritical butane abstraction technique overcomes one existing for supercritical carbon dioxide extraction technology
A little problems, but still use the stronger organic reagent of toxicity, and the reaction time is longer, however it remains at high cost, low efficiency, peace
The problem of full property etc..Therefore, it is necessary to be improved the prior art.
Summary of the invention
Technical assignment of the invention is to solve the deficiencies in the prior art, provides that a kind of recovery rate is high, purity is high, and material adapts to
The extracting method of the wide cannabidiol CBD of property.
The present invention pass through following technical proposal realize: a kind of extracting method of cannabidiol CBD, it is characterised in that including with
Lower step:
Step (1) selects the flower of fresh Chinese fiber crops and/or leaf to be sheared, or selection moisture lower than 5% drying Chinese fiber crops flower with/
Or leaf is crushed to 5-10 mesh, obtains particle；
Step (2), after the particle of step (1) is mixed with pure water by 1: 5-20 mass ratio, in -196 DEG C of freezing 1- of -100-
4h, heating is thawed to after 40-60 DEG C, then at -196 DEG C of freezing 1-4h of -100-, then is heated up and is thawed to 40-60 DEG C, repeatedly
2-5 times, obtain frozen materials；
Step (3) is mixed the frozen materials of step (2) with water by 1:5-10 mass ratio, in 100-375 DEG C of temperature, 10-
Under 15MPa pressure, three times with Subcritical Water Extraction, each 10-30min filters to take filtrate every time, and filter residue continues to extract, and merges
Filtrate three times is filtered with the hyperfiltration film of molecular cut off 80-120KD, is concentrated, obtains cannabidiol medicinal extract；
Step (4), by the medicinal extract of step (3) with ethyl alcohol be diluted to solid contents be 2~4%, carry out gradient with chromatographic column and wash
It is de-, eluate is collected, is concentrated at 40-60 DEG C, is obtained hemp two and divide concentrate；
Step (5), in the cannabidiol concentrate of step (4), be added mass concentration be 90% ethyl alcohol be dissolved to supersaturation
Afterwards, crystal is precipitated, after pure water crystal, drying crystallization is to get cannabidiol CBD product.
The Chinese fiber crops refer to the industrial hemp that tetrahydrocannabinol THC content is lower than 0.3%.
Further, cold source used in -196 DEG C of -100- freezing 1-4h of the step (2) is low temperature liquid nitrogen, with ultralow
The method that temperature destroys cell wall solves the insufficient technical problem of traditional handicraft lysed cells wall.
Further, in step (3), during the subcritical abstraction, batch type is taken, it may be assumed that stirring 5 minutes,
Stop 5 minutes, be stirred for 5 minutes, then stop 5 minutes, such alternate cycles 10-30min, mixing speed 20-40r/min, with
Formula of having a rest stirring solves to extract insufficient technical problem in conjunction with extraction.
Further, in step (4), the chromatography column packing is silica gel, and partial size 5-100um, mobile phase is that quality is dense
Degree is the ethyl alcohol of 60-80%.
The present invention is rapidly frozen by the ultralow temperature of -196 DEG C of -100- freezing 1-4h, to destroy the cell wall of raw material, then
By subcritical abstraction, the cannabidiol CBD product that recovery rate is high, with high purity is obtained.
Generated beneficial effect is the present invention compared with prior art:
The present invention can both extract dry work material, can also extract to fresh material, can thus solve
Dried material problem under feeding caused by process is tedious directly extracts fresh material and does not also just have to worry to expand kind
After plant, can there is that storage is a large amount of, material is to be baked leads to material deterioration a floral leaf collecting period, realize continuous production.Especially
It is handled by ultralow temperature breaking-wall cell, makes fresh or dry material that can occur to be broken and break under the action of thermal stress
Wall avoids traditional enzymolysis process is unstable, enzymatic hydrolysis is insufficient broken wall is caused to be imitated to efficiently extract effective component therein
The problems such as rate is low.Production process of the present invention is simple, and sporoderm-broken rate is high, it is entirely avoided what effective component was lost in extraction process asks
Topic.
Specific embodiment
Below by embodiment, the present invention will be further described.
Embodiment 1
A kind of extracting method of cannabidiol CBD, comprising the following steps:
Step (1) selects the flower of fresh process hemp of the tetrahydrocannabinol THC content lower than 0.3% and leaf to be sheared, and obtains broken
Material；
Step (2) after mixing the particle of step (1) by 1: 5 mass ratio with pure water, freezes 4h in -100 DEG C of liquid nitrogen,
Heating is thawed to after 40 DEG C, and 4h is freezed in -100 DEG C of liquid nitrogen, then the defrosting that heats up 5 times repeatedly, obtains cold to 40 DEG C
Freeze material；
Step (3) is mixed the frozen materials of step (2) with water by 1:5 mass ratio, under 100 DEG C of temperature, 10MPa pressure, is used
Subcritical Water Extraction three times, takes batch type every time, it may be assumed that stirring 5 minutes stops 5 minutes, is stirred for 5 minutes, then stop 5 points
Clock, such alternate cycles 20min, mixing speed 20r/min take filtrate after filtering every time, and filter residue continues to extract, and merges three times
Filtrate is filtered with the hyperfiltration film of molecular cut off 80-120KD, is concentrated, obtains cannabidiol medicinal extract；
Step (4), by the medicinal extract of step (3) with ethyl alcohol be diluted to solid contents be 2%, carry out gradient elution with chromatographic column,
Eluate is collected, is concentrated at 40 DEG C, is obtained hemp two and divide concentrate；Chromatography column packing is silica gel, partial size 5um, mobile phase
The ethyl alcohol for being 60% for mass concentration；
Step (5), in the cannabidiol concentrate of step (4), be added mass concentration be 90% ethyl alcohol be dissolved to supersaturation
Afterwards, crystal is precipitated, after pure water crystal, drying crystallization is to get cannabidiol CBD product.
Embodiment 2
A kind of extracting method of cannabidiol CBD, comprising the following steps:
The industrial hemp of the drying of step (1), selection moisture lower than 5%, tetrahydrocannabinol THC content lower than 0.3% is crushed to 5
Mesh obtains particle；
Step (2) after mixing the particle of step (1) by 1: 10 mass ratio with pure water, freezes 1h in -196 DEG C of liquid nitrogen,
Heating is thawed to after 60 DEG C, and 1h is freezed in -196 DEG C of liquid nitrogen, then the defrosting that heats up 2 times repeatedly, obtains cold to 60 DEG C
Freeze material；
Step (3) is mixed the frozen materials of step (2) with water by 1:10 mass ratio, under 375 DEG C of temperature, 10MPa pressure,
Three times with Subcritical Water Extraction, batch type is taken every time, it may be assumed that stirring 5 minutes stops 5 minutes, is stirred for 5 minutes, then stop 5
Minute, such alternate cycles 30min, mixing speed 40r/min take filtrate after filtering every time, and filter residue continues to extract, and merges three
Secondary filtrate is filtered with the hyperfiltration film of molecular cut off 80-120KD, is concentrated, obtains cannabidiol medicinal extract；
Step (4), by the medicinal extract of step (3) with ethyl alcohol be diluted to solid contents be 4%, carry out gradient elution with chromatographic column,
Eluate is collected, is concentrated at 60 DEG C, is obtained hemp two and divide concentrate；Chromatography column packing is silica gel, partial size 100um, flowing
It is mutually the ethyl alcohol that mass concentration is 80%；
Step (5), in the cannabidiol concentrate of step (4), be added mass concentration be 90% ethyl alcohol be dissolved to supersaturation
Afterwards, crystal is precipitated, after pure water crystal, drying crystallization is to get cannabidiol CBD product.
Embodiment 3
A kind of extracting method of cannabidiol CBD, comprising the following steps:
Step (1) selects the flower of fresh process hemp of the tetrahydrocannabinol THC content lower than 0.3% and leaf to be sheared, and obtains broken
Material；
Step (2) after mixing the particle of step (1) by 1: 8 mass ratio with pure water, freezes 2h in -150 DEG C of liquid nitrogen,
Heating is thawed to after 50 DEG C, and 2h is freezed in -150 DEG C of liquid nitrogen, then the defrosting that heats up 3 times repeatedly, obtains cold to 50 DEG C
Freeze material；
Step (3) is mixed the frozen materials of step (2) with water by 1:8 mass ratio, under 200 DEG C of temperature, 12MPa pressure, is used
Subcritical Water Extraction three times, takes batch type every time, it may be assumed that stirring 5 minutes stops 5 minutes, is stirred for 5 minutes, then stop 5 points
Clock, such alternate cycles 30min, mixing speed 30r/min take filtrate after filtering every time, and filter residue continues to extract, and merges three times
Filtrate is filtered with the hyperfiltration film of molecular cut off 80-120KD, is concentrated, obtains cannabidiol medicinal extract；
Step (4), by the medicinal extract of step (3) with ethyl alcohol be diluted to solid contents be 3%, carry out gradient elution with chromatographic column,
Eluate is collected, is concentrated at 50 DEG C, is obtained hemp two and divide concentrate；Chromatography column packing is silica gel, partial size 80um, mobile phase
The ethyl alcohol for being 70% for mass concentration；
Step (5), in the cannabidiol concentrate of step (4), be added mass concentration be 90% ethyl alcohol be dissolved to supersaturation
Afterwards, crystal is precipitated, after pure water crystal, drying crystallization is to get cannabidiol CBD product.
Embodiment 4
A kind of extracting method of cannabidiol CBD, comprising the following steps:
The industrial hemp of the drying of step (1), selection moisture lower than 5%, tetrahydrocannabinol THC content lower than 0.3% is crushed to 8
Mesh obtains particle；
Step (2) after mixing the particle of step (1) by 1: 15 mass ratio with pure water, freezes 2h in -170 DEG C of liquid nitrogen,
Heating is thawed to after 50 DEG C, and 2h is freezed in -170 DEG C of liquid nitrogen, then the defrosting that heats up 4 times repeatedly, obtains cold to 50 DEG C
Freeze material；
Step (3) is mixed the frozen materials of step (2) with water by 1:7 mass ratio, under 300 DEG C of temperature, 11MPa pressure, is used
Subcritical Water Extraction three times, takes batch type every time, it may be assumed that stirring 5 minutes stops 5 minutes, mixing speed 40r/min, often
Filtrate is taken after secondary filtering, filter residue continues to extract, and merges filtrate three times, is carried out with the hyperfiltration film of molecular cut off 80-120KD
Filtering, concentration, obtain cannabidiol medicinal extract；
Step (4), by the medicinal extract of step (3) with ethyl alcohol be diluted to solid contents be 4%, carry out gradient elution with chromatographic column,
Eluate is collected, is concentrated at 60 DEG C, is obtained hemp two and divide concentrate；Chromatography column packing is silica gel, partial size 50um, mobile phase
The ethyl alcohol for being 60% for mass concentration；
Step (5), in the cannabidiol concentrate of step (4), be added mass concentration be 90% ethyl alcohol be dissolved to supersaturation
Afterwards, crystal is precipitated, after pure water crystal, drying crystallization is to get cannabidiol CBD product.
Embodiment 5
A kind of extracting method of cannabidiol CBD, comprising the following steps:
The industrial hemp of the drying of step (1), selection moisture lower than 5%, tetrahydrocannabinol THC content lower than 0.3% is crushed to 8
Mesh obtains particle；
Step (2) after mixing the particle of step (1) by 1: 17 mass ratio with pure water, freezes 2h in -180 DEG C of liquid nitrogen,
Heating is thawed to after 50 DEG C, and 2h is freezed in -180 DEG C of liquid nitrogen, then the defrosting that heats up 4 times repeatedly, obtains cold to 50 DEG C
Freeze material；
Step (3) is mixed the frozen materials of step (2) with water by 1:6 mass ratio, under 300 DEG C of temperature, 11MPa pressure, is used
Subcritical Water Extraction three times, takes batch type every time, it may be assumed that stirring 5 minutes stops 5 minutes, mixing speed 40r/min, often
Filtrate is taken after secondary filtering, filter residue continues to extract, and merges filtrate three times, is carried out with the hyperfiltration film of molecular cut off 80-120KD
Filtering, concentration, obtain cannabidiol medicinal extract；
Step (4), by the medicinal extract of step (3) with ethyl alcohol be diluted to solid contents be 4%, carry out gradient elution with chromatographic column,
Eluate is collected, is concentrated at 60 DEG C, is obtained hemp two and divide concentrate；Chromatography column packing is silica gel, partial size 50um, mobile phase
The ethyl alcohol for being 60% for mass concentration；
Step (5), in the cannabidiol concentrate of step (4), be added mass concentration be 90% ethyl alcohol be dissolved to supersaturation
Afterwards, crystal is precipitated, after pure water crystal, drying crystallization is to get cannabidiol CBD product.
Embodiment 6
A kind of extracting method of cannabidiol CBD, comprising the following steps:
Step (1) selects the flower of fresh process hemp of the tetrahydrocannabinol THC content lower than 0.3% and leaf to be sheared, and obtains broken
Material；
Step (2) after mixing the particle of step (1) by 1: 7 mass ratio with pure water, freezes 2h in -120 DEG C of liquid nitrogen,
Heating is thawed to after 50 DEG C, and 2h is freezed in -120 DEG C of liquid nitrogen, then the defrosting that heats up 3 times repeatedly, obtains cold to 50 DEG C
Freeze material；
Step (3) is mixed the frozen materials of step (2) with water by 1:6 mass ratio, under 300 DEG C of temperature, 12MPa pressure, is used
Subcritical Water Extraction three times, takes batch type every time, it may be assumed that stirring 5 minutes stops 5 minutes, is stirred for 5 minutes, then stop 5 points
Clock, such alternate cycles 30min, mixing speed 35r/min take filtrate after filtering every time, and filter residue continues to extract, and merges three times
Filtrate is filtered with the hyperfiltration film of molecular cut off 80-120KD, is concentrated, obtains cannabidiol medicinal extract；
Step (4), by the medicinal extract of step (3) with ethyl alcohol be diluted to solid contents be 3%, carry out gradient elution with chromatographic column,
Eluate is collected, is concentrated at 55 DEG C, is obtained hemp two and divide concentrate；Chromatography column packing is silica gel, partial size 80um, mobile phase
The ethyl alcohol for being 70% for mass concentration；
Step (5), in the cannabidiol concentrate of step (4), be added mass concentration be 90% ethyl alcohol be dissolved to supersaturation
Afterwards, crystal is precipitated, after pure water crystal, drying crystallization is to get cannabidiol CBD product.
Reference examples 1
Flower, the leaf of drying industrial hemp by the tetrahydrocannabinol THC content filtered out lower than 0.3%, moisture lower than 5% are crushed to
10 mesh are mixed with the ratio of 1:10 with pure water, then are obtained by extraction with Subcritical Water Extraction 30min, mixing speed 40r/min
Extract liquor be filtered with the hyperfiltration film of molecular cut off 80-120KD, filtrate is concentrated at 60 DEG C removes extra water
Point, obtain the concentrate of cannabidiol；Cannabidiol concentrate is diluted, the cannabidiol after dilution is concentrated by chromatographic column
Liquid carries out gradient elution, collects target eluent；Target eluent is concentrated, crystallization obtains cannabidiol product.
Reference examples 2
After fresh process cannabis of the tetrahydrocannabinol THC content filtered out lower than 0.3%, leaf are shredded, with the quality of 1:10
Ratio is mixed with pure water, then with Subcritical Water Extraction 30min, mixing speed 40r/min, the extract liquor retention being obtained by extraction
The hyperfiltration film of molecular weight 80-120KD is filtered, and filtrate is concentrated at 60 DEG C removes extra moisture, obtains hemp two
The concentrate of phenol；Cannabidiol concentrate is diluted, gradient is carried out to the cannabidiol concentrate after dilution by chromatographic column and is washed
It is de-, collect target eluent；Target eluent is concentrated, crystallization obtains cannabidiol product.
Compare above embodiments recovery rate and cannabidiol CBD purity:
。
Claims (4)
1. a kind of extracting method of cannabidiol CBD, it is characterised in that the following steps are included:
Step (1) selects the flower of fresh Chinese fiber crops and/or leaf to be sheared, or selection moisture lower than 5% drying Chinese fiber crops flower with/
Or leaf is crushed to 5-10 mesh, obtains particle；
Step (2), after the particle of step (1) is mixed with pure water by 1: 5-20 mass ratio, in -196 DEG C of freezing 1- of -100-
4h, heating is thawed to after 40-60 DEG C, then at -196 DEG C of freezing 1-4h of -100-, then is heated up and is thawed to 40-60 DEG C, repeatedly
2-5 times, obtain frozen materials；
Step (3) is mixed the frozen materials of step (2) with water by 1:5-10 mass ratio, in 100-375 DEG C of temperature, 10-
Under 15MPa pressure, three times with Subcritical Water Extraction, each 10-30min filters to take filtrate every time, and filter residue continues to extract, and merges
Filtrate three times is filtered with the hyperfiltration film of molecular cut off 80-120KD, is concentrated, obtains cannabidiol medicinal extract；
Step (4), by the medicinal extract of step (3) with ethyl alcohol be diluted to solid contents be 2~4%, eluted with chromatographic column, receive
Collect eluate, is concentrated at 40-60 DEG C, obtains hemp two and divide concentrate；
Step (5), in the cannabidiol concentrate of step (4), be added mass concentration be 90% ethyl alcohol be dissolved to supersaturation
Afterwards, crystal is precipitated, after pure water crystal, drying crystallization is to get cannabidiol CBD product.
2. the extracting method of cannabidiol CBD as described in claim 1, it is characterised in that-the 100--of the step (2)
Cold source used in 196 DEG C of freezing 1-4h is low temperature liquid nitrogen.
3. the extracting method of cannabidiol CBD as described in claim 1, it is characterised in that in the step (3), subcritical water
In extraction process, batch type is taken, it may be assumed that stirring 5 minutes stops 5 minutes, is stirred for 5 minutes, then stops 5 minutes, so alternately
Recycle 10-30min, mixing speed 20-40r/min.
4. the extracting method of cannabidiol CBD as described in claim 1, it is characterised in that in the step (4), chromatographic column is filled out
Material is silica gel, and partial size 5-100um, mobile phase is the ethyl alcohol that mass concentration is 60-80%.
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| CN111574332A (en) * | 2020-04-14 | 2020-08-25 | 周宇平 | Crystallization process for purifying cannabidiol |
| CN112062658A (en) * | 2020-08-21 | 2020-12-11 | 滇麻生物科技(曲靖)有限公司 | Method for simultaneously preparing CBG, CBDV, CBD and THCV from industrial hemp |
| CN114651880A (en) * | 2022-04-11 | 2022-06-24 | 郑小春 | Ultralow-temperature processing technology of tea |
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