CN111960923A - Recycling method of cannabidiol extraction process waste and application thereof - Google Patents
Recycling method of cannabidiol extraction process waste and application thereof Download PDFInfo
- Publication number
- CN111960923A CN111960923A CN201911401594.6A CN201911401594A CN111960923A CN 111960923 A CN111960923 A CN 111960923A CN 201911401594 A CN201911401594 A CN 201911401594A CN 111960923 A CN111960923 A CN 111960923A
- Authority
- CN
- China
- Prior art keywords
- extraction process
- waste
- reaction
- cannabidiol
- solution
- 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.)
- Granted
Links
Images
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
- C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
- C07C37/002—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by transformation of a functional group, e.g. oxo, carboxyl
-
- 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
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
-
- 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
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Extraction Or Liquid Replacement (AREA)
Abstract
The invention relates to a recycling method of cannabidiol extraction process waste and application thereof, wherein the recycling method comprises the following steps: mixing the waste generated in the cannabidiol extraction process with an acidic solution for reaction, and mixing the product with an alkaline solution for reaction. The method has the advantages that the waste is sequentially reacted with the acid solution and the alkaline solution, so that the content of the unfavorable component tetrahydrocannabinol in the waste is greatly reduced, and the content of the favorable component cannabidiol is obviously improved. The method solves the problem of post-treatment of industrial waste generated by the CBD extraction and production process, converts harmful extraction waste into CBD which is safer and has high medicinal value by the method, provides a very valuable method for treating the waste generated by the industrial hemp extraction process, indirectly improves the yield of the CBD in the industrial hemp, changes waste into valuable, and effectively reduces environmental pollution.
Description
Technical Field
The invention belongs to the technical field of industrial extraction, and particularly relates to a recycling method of cannabidiol extraction process waste and application thereof.
Background
Tetrahydrocannabinol (THC) in cannabis is one of the main toxic components of cannabis plants and products thereof causing addiction to abusers and personal injury, and can cause adverse reactions such as hallucinations, convulsion, vomiting, multiple sclerosis recurrence and the like. THC is a lipophilic, hydrophobic, viscous oil, volatile with a pKa of 10.6, typically present in cannabis plants as a mixture of monocarboxylic acids, readily decomposable by exposure to air, light or heat; can be oxidized into cannabinol under acidic condition, and is stable in alkaline and organic solvents. During the extraction process of the cannabinoids, the cannabinoids are extracted along with other substances, and in order to prevent the cannabinoids from being used as drugs or circulating in other illegal ways, the cannabinoids need to be thoroughly destroyed after the cannabinoids are extracted.
Cannabidiol (CBD) is a non-toxic, non-addictive active substance of industrial cannabis, with high value, and is soluble in ethanol, methanol, ether, benzene, chloroform and petroleum ether. GW pharmaceutical company reported a CBD-containing oral liquid with a trade name Epidolex for the treatment of Dravet syndrome (a type of epilepsy) in 2014. CBD also has pharmacological effects of anticonvulsant, antibacterial, anti-inflammatory, anti-anesthetic and nervous system protective; meanwhile, the effect of tetrahydrocannabinol (THC for short) on the human nervous system can be effectively eliminated, and the compound is called as an antitoxic compound.
The industrial hemp extraction waste contains a small amount of THC, which is a main byproduct of industrial extraction of CBD and is one of main impurities in CBD. How to treat THC-containing waste in the industrial hemp extraction industry, controlling the flow direction of THC and controlling the impurity content of CBD is one of the difficulties of the prior industrial hemp extraction process, and no better treatment method exists at present, so that if the THC in the industrial hemp extraction waste can be converted into more valuable CBD, the method is a great innovation for the hemp extraction industry.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a recycling method of cannabidiol extraction process waste and application thereof.
In order to achieve the purpose, the invention adopts the following technical scheme:
in one aspect, the present invention provides a recycling method of cannabidiol extraction process waste, the recycling method comprising: mixing the waste generated in the cannabidiol extraction process with an acidic solution for reaction, and mixing the product with an alkaline solution for reaction.
The recycling method of the cannabidiol extraction process waste, which is related by the invention, enables the content of unfavorable component tetrahydrocannabinol (THC for short) in the waste to be greatly reduced and the content of favorable component cannabidiol (CBD for short) to be remarkably improved by sequentially reacting the waste with an acid solution and an alkaline solution, and supposes that the following reaction process can be generated, namely part of tetrahydrocannabinol is converted into cannabidiol:
THC and CBD are two main cannabinoids in industrial cannabis, wherein the THC content is about 2 per mill, the CBD content is 7-9 per mill, but THC is strictly regulated and controlled in China as a main addictive component in cannabis, and the treatment of THC is always a difficult point in the industrial cannabis industry. The traditional method mainly comprises incineration, but the incineration process pollutes the environment and can generate harmful substances which harm the health of staff. THC destruction has also been reported by chemical methods, but these methods have problems of environmental pollution and increase in cannabinoid extraction costs.
The method solves the problem of post-treatment of industrial waste generated by the CBD extraction and production process, converts harmful extraction waste into the CBD which is safer and has high medicinal value by the method, provides a very valuable method for treating the waste generated by the industrial hemp extraction process, indirectly improves the yield of the CBD in the industrial hemp, changes waste into valuable and effectively reduces environmental pollution.
Preferably, the reuse method includes the steps of:
(1) mixing the waste generated in the cannabidiol extraction process with an acidic solution for reaction, extracting with an organic solvent, washing an organic phase, and concentrating to obtain an oily intermediate;
(2) mixing the intermediate obtained in the step (1) with an alkaline solution for reaction, extracting with an organic solvent, washing an organic phase, and crystallizing to obtain a white solid.
Preferably, the acidic solution in step (1) comprises any one or a combination of at least two of aqueous hydrobromic acid solution, aqueous hydrochloric acid solution, aqueous perchloric acid solution, aqueous hydroiodic acid solution or trichloroacetic acid; the combination of the at least two types, for example, the combination of the hydrobromic acid aqueous solution and the hydrochloric acid aqueous solution, the combination of the hydrochloric acid aqueous solution and the perchloric acid aqueous solution, and the like, may be any combination, and thus, details are not repeated herein.
Preferably, the mass concentration of the hydrobromic acid aqueous solution is 30-50%, for example, 30%, 32%, 35%, 38%, 40%, 42%, 45%, 48%, or 50%, and specific values within the range can be selected, and are not described herein again.
Preferably, the mass concentration of the hydrochloric acid aqueous solution is 30-38%, for example, 30%, 32%, 33%, 34%, 35%, 36%, 37%, 38%, etc., and specific values within the range can be selected, which is not described herein again.
Preferably, the mass concentration of the perchloric acid aqueous solution is 30-72%, for example, 30%, 35%, 40%, 45%, 50%, 60%, 70% or 72%, and the like, and specific values within the range can be selected, which is not described in detail herein.
Preferably, the mass concentration of the hydriodic acid aqueous solution is 30-57%, for example, 30%, 35%, 38%, 40%, 45%, 48%, 50%, 55%, or 57%, and the like, and specific values within the range can be selected, and are not described in detail herein.
The concentration of the acidic solution according to the invention is chosen specifically within the above-mentioned range of concentrations, since a further reduction in concentration would affect the reaction rate or even render it non-reactive, since the concentration is the maximum concentration of the commercially available product.
Preferably, the reaction temperature in step (1) is 20-80 ℃, for example 20 ℃, 30 ℃, 40 ℃, 50 ℃, 60 ℃, 70 ℃ or 80 ℃, and the like, and specific values in the range can be selected, and are not repeated herein.
The temperature of the reaction is specifically chosen in the range of 20-80 ℃ because above this temperature more by-products are produced and below this temperature the reaction rate is greatly reduced.
Preferably, the reaction time in step (1) is 3-10h, for example, 3h, 4h, 5h, 6h, 7h, 8h, 9h or 10h, and the specific values in the range can be selected, and thus detailed description is omitted here.
Preferably, the organic solvent in step (1) comprises ethyl acetate, isopropyl acetate, dichloromethane and other water-immiscible organic solvents.
Preferably, the temperature of the extraction in step (1) is 20-30 ℃, for example, 20 ℃, 22 ℃, 24 ℃, 25 ℃, 26 ℃, 27 ℃, 28 ℃ or 30 ℃, and the like, and specific values in the range can be selected, which is not described in detail herein.
Preferably, the washing of the organic phase in step (1) means: the organic phase is washed with sodium bicarbonate to a pH of 6-7 in the aqueous phase in order to reduce the acid content of the intermediate. For example pH 6, pH 6.5 or pH 7.
Preferably, the solvent of the alkaline solution in the step (2) comprises ethanol, and the solute comprises any one or a combination of at least two of sodium hydroxide, potassium hydroxide, sodium tert-butoxide, potassium tert-butoxide or sodium ethoxide; the combination of at least two of the above-mentioned compounds, such as the combination of sodium hydroxide and potassium hydroxide, the combination of sodium tert-butoxide and potassium tert-butoxide, the combination of potassium tert-butoxide and sodium ethoxide, etc., can be selected in any combination manner, and will not be described herein again.
Preferably, the mass concentration of the sodium hydroxide is 5-40%, for example, 5%, 10%, 15%, 20%, 25%, 30%, 35%, or 40%, and specific values within the range can be selected, which is not described herein again.
Preferably, the mass concentration of the potassium hydroxide is 5-50%, for example, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or 50%, and specific values within the range can be selected, which is not described herein again.
Preferably, the mass concentration of the sodium tert-butoxide is 5-21%, for example 5%, 10%, 15%, 20% or 21%, and the specific values in the range can be selected, which is not described herein again.
Preferably, the mass concentration of the potassium tert-butoxide is 5-21%, for example 5%, 10%, 15%, 20% or 21%, and specific values within the range can be selected, which is not described herein again.
Preferably, the mass concentration of the sodium ethoxide is 5-21%, for example, 5%, 10%, 15%, 20%, or 21%, and specific values within the range can be selected, and are not described herein again.
The concentration of the alkaline solution related to the invention is specifically selected from the above concentration range because the further increase of the concentration causes poor system fluidity, reduced heat conduction rate and increased reaction byproducts; further reduction in concentration may reduce the reaction rate or render it unreactive.
Preferably, the reaction temperature in step (2) is 20-60 ℃, for example, 20 ℃, 25 ℃, 30 ℃, 40 ℃, 50 ℃ or 60 ℃, and the like, and specific values in the range can be selected, and are not described in detail herein.
The temperature of the reaction is specifically selected in the range of 20-60 ℃ because reaction by-products increase beyond this temperature and the reaction rate decreases below this temperature.
Preferably, the reaction time in step (2) is 5-8h, such as 5h, 6h, 7h or 8h, etc.
Preferably, after the reaction in the step (2) is finished, the ethanol is removed by concentration and evaporation, so that extraction and separation are facilitated.
Preferably, the organic reagent in step (2) comprises dichloromethane, chloroform, methyl tert-butyl ether or isopropyl acetate, etc.
Preferably, said washing of the organic phase in step (2) means: the organic phase is washed with hydrochloric acid solution to a pH value of 5-7 of the aqueous phase, so as to reduce the residue of alkali and remove impurities. For example, pH 5, pH 5.5, pH 6, pH 6.5, pH 7, or the like.
Preferably, the crystallization of step (2) is performed using n-heptane, n-hexane, cyclohexane or petroleum ether.
As a preferable technical scheme of the invention, the recycling method of the cannabidiol extraction process waste comprises the following steps:
(1) mixing the waste generated in the cannabidiol extraction process with an acidic solution at 20-80 ℃ for reaction for 3-10h, extracting with ethyl acetate at 20-30 ℃, washing the organic phase with sodium bicarbonate until the pH value of the aqueous phase is 6-7, and concentrating to obtain an oily intermediate;
(2) mixing the intermediate obtained in the step (1) with an alkaline solution at the temperature of 20-60 ℃ for reaction for 5-8h, extracting with dichloromethane, washing an organic phase with a hydrochloric acid solution until the pH value of a water phase is 5-7, and adding n-heptane for crystallization to obtain a white solid.
In another aspect, the present invention provides a method for recycling the waste from the cannabidiol extraction process, the method being applied to post-treatment of the waste from the cannabidiol extraction process.
Compared with the prior art, the invention has the following beneficial effects:
the recycling method of the cannabidiol extraction process waste enables the content of unfavorable component tetrahydrocannabinol (THC for short) in the waste to be greatly reduced and the content of favorable component cannabidiol (CBD for short) to be obviously improved by enabling the waste to react with the acidic solution and the alkaline solution in sequence. The method solves the problem of post-treatment of industrial waste generated by the CBD extraction and production process, converts harmful extraction waste into CBD which is safer and has high medicinal value by the method, provides a very valuable method for treating the waste generated by the industrial hemp extraction process, indirectly improves the yield of the CBD in the industrial hemp, changes waste into valuable, and effectively reduces environmental pollution.
Drawings
FIG. 1 is a high performance liquid chromatogram of a cannabidiol control;
FIG. 2 is a high performance liquid chromatogram of a sample before treatment in example 1;
FIG. 3 is a high performance liquid chromatogram of the treated sample of example 1.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
The raw materials of the following examples are all wastes generated in the cannabidiol extraction process.
In the following examples, the contents of Cannabidiol (CBD) and Tetrahydrocannabinol (THC) in the samples before and after treatment were determined by high performance liquid chromatography, and the specific operating method was as follows:
chromatographic conditions and system applicability test: octadecylsilane chemically bonded silica is used as a filling agent; taking acetonitrile as a mobile phase A, taking water as a mobile phase B, and carrying out isocratic elution according to the ratio of A (%): B (%) (70: 30); the detection wavelength was 210 nm.
Preparation of control solutions: precisely weighing cannabidiol CBD reference substance, adding ethanol (1:1) to make reference substance solution containing 0.1 mg/lmL; accurately weighing tetrahydrocannabinol THC reference substance, adding methanol (1:1) to obtain reference substance solution containing 0.01 mg/lmL.
Preparation of a test solution: taking 25mg of samples before and after treatment, precisely weighing, placing in a 25mL measuring flask, adding 20mL of acetonitrile-water (1:1), carrying out ultrasonic treatment for 10min, adding acetonitrile-water (1:1) to dilute to a scale, shaking, filtering with a microporous filter membrane (0.45pm), and taking a subsequent filtrate.
The determination method comprises the following steps: precisely sucking 10 μ L of each of the reference solution and the sample solution, injecting into liquid chromatograph, and measuring.
Example 1
The embodiment provides a recycling method of cannabidiol extraction process waste, which comprises the following steps:
(1) mixing the waste generated in the cannabidiol extraction process with 48% hydrobromic acid aqueous solution at 40 ℃ for 5h, monitoring the reaction completion by TLC, extracting at 25 ℃ by using ethyl acetate, washing an organic phase by using sodium bicarbonate until the pH value of a water phase is 6, and concentrating the organic phase to obtain an oily substance;
(2) mixing the oily matter obtained in the step (1) with 25% sodium hydroxide ethanol solution at 40 ℃ for 6h, detecting complete reaction by HPLC, cooling to 25 ℃, concentrating and distilling the ethanol, adding water and dichloromethane for extraction, separating liquid, extracting the water phase with dichloromethane again, combining the organic phases, washing the organic phases with 1N hydrochloric acid solution until the pH value of the water phase is 6, and adding N-heptane for crystallization to obtain white solid.
Through high performance liquid chromatography detection and calculation by adopting a peak area normalization method, the THC content in the waste before treatment is 56.8%, and the CBD content is 2.5%; the THC content of the treated product is 3.6%, the CBD content is 82.8%, and the liquid chromatogram is shown in fig. 1-3 (fig. 1 is chromatogram of CBD reference cannabidiol, fig. 2 is high performance liquid chromatogram of the sample before treatment, fig. 3 is high performance liquid chromatogram of the treated sample, THC peak-off time is about 14.9min, and CBD peak-off time is about 8.4 min).
Example 2
The embodiment provides a recycling method of cannabidiol extraction process waste, which comprises the following steps:
(1) mixing the waste generated in the cannabidiol extraction process with 50% hydriodic acid aqueous solution at 30 ℃ for 10h, monitoring the reaction by TLC to be complete, extracting at 20 ℃ by using ethyl acetate, washing an organic phase by using sodium bicarbonate until the pH value of a water phase is 7, and concentrating the organic phase to obtain an oily substance;
(2) mixing the oily matter obtained in the step (1) with 40% potassium hydroxide ethanol solution at 60 ℃ for reaction for 5h, detecting complete reaction by HPLC, cooling to 30 ℃, concentrating and steaming out ethanol, adding water and dichloromethane for extraction, separating liquid, extracting the water phase with dichloromethane again, combining the organic phases, washing the organic phases with 1N hydrochloric acid solution until the pH value of the water phase is 7, and adding N-heptane for crystallization to obtain white solid.
Through high performance liquid chromatography detection and calculation by adopting a peak area normalization method, the THC content in the waste before treatment is 56.8%, and the CBD content is 2.5%; the THC content of the treated product is 4.1 percent, and the CBD content is 80.6 percent.
Example 3
The embodiment provides a recycling method of cannabidiol extraction process waste, which comprises the following steps:
(1) mixing the waste generated in the cannabidiol extraction process with 30% perchloric acid aqueous solution at 50 ℃ for reaction for 3h, monitoring the reaction by TLC to be complete, extracting by using ethyl acetate at 30 ℃, washing an organic phase by using sodium bicarbonate until the pH value of a water phase is 7, and concentrating the organic phase to obtain an oily substance;
(2) mixing the oily matter obtained in the step (1) with a 20% sodium tert-butoxide ethanol solution at 50 ℃ for 8h, detecting complete reaction by HPLC, cooling to 20 ℃, concentrating and distilling off ethanol, adding water and dichloromethane for extraction, separating liquid, extracting the water phase with dichloromethane once again, combining the organic phases, washing the organic phases with a 1N hydrochloric acid solution until the pH value of the water phase is 6, and adding N-heptane for crystallization to obtain a white solid.
Through high performance liquid chromatography detection and calculation by adopting a peak area normalization method, the THC content in the waste before treatment is 56.8%, the CBD content is 2.5%, and the THC content in the product after the treatment is 3.1%, and the CBD content is 83.2%.
Example 4
The embodiment provides a recycling method of cannabidiol extraction process waste, which comprises the following steps:
(1) mixing the waste generated in the cannabidiol extraction process with 30% hydrochloric acid aqueous solution at 40 ℃ for 8h, monitoring the reaction by TLC to be complete, extracting by using ethyl acetate at 25 ℃, washing an organic phase by using sodium bicarbonate until the pH value of an aqueous phase is 7, and concentrating the organic phase to obtain an oily substance;
(2) mixing the oily matter obtained in the step (1) with 20% sodium ethoxide ethanol solution at 40 ℃ for reaction for 7h, detecting complete reaction by HPLC, cooling to 25 ℃, concentrating and steaming out ethanol, adding water and dichloromethane for extraction, separating liquid, extracting the water phase with dichloromethane again, combining organic phases, washing the organic phases with 1N hydrochloric acid solution until the pH value of the water phase is 6, and adding N-heptane for crystallization to obtain white solid.
Through high performance liquid chromatography detection and calculation by adopting a peak area normalization method, the THC content in the waste before treatment is 56.8%, and the CBD content is 2.5%; the THC content of the treated product is 3.7 percent, and the CBD content is 81.6 percent.
The above examples show that, after the waste is treated by the method of the present invention, the THC content in the sample is significantly reduced, and the CBD content is significantly increased, which indicates that the THC in the waste can be converted into CBD after the cannabidiol extraction process waste is treated by the method of the present invention, and the conversion rate is above 90%, the method solves the post-treatment problem of the industrial waste generated by the industrial extraction and production of CBD, converts the harmful component THC in the extracted waste into CBD which is safer and has great medicinal value by the method, provides a very valuable method for the waste treatment generated by the industrial cannabis extraction process, and indirectly increases the CBD yield in industrial cannabis, so to say, changes waste into valuables, and effectively reduces environmental pollution.
The applicant states that the present invention is illustrated by the above examples to provide a recycling method of cannabidiol extraction process waste and its application, but the present invention is not limited to the above examples, i.e. it is not meant to be dependent on the above examples to practice the present invention. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
The preferred embodiments of the present invention have been described in detail, however, the present invention is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solution of the present invention within the technical idea of the present invention, and these simple modifications are within the protective scope of the present invention.
It should be noted that the various technical features described in the above embodiments can be combined in any suitable manner without contradiction, and the invention is not described in any way for the possible combinations in order to avoid unnecessary repetition.
Claims (10)
1. A recycling method of cannabidiol extraction process waste is characterized by comprising the following steps: mixing the waste generated in the cannabidiol extraction process with an acidic solution for reaction, and mixing the product with an alkaline solution for reaction.
2. The recycling method of cannabidiol extraction process waste as claimed in claim 1, wherein the recycling method comprises the steps of:
(1) mixing the waste generated in the cannabidiol extraction process with an acidic solution for reaction, extracting with an organic solvent, washing an organic phase, and concentrating to obtain an oily intermediate;
(2) mixing the intermediate obtained in the step (1) with an alkaline solution for reaction, extracting with an organic solvent, washing an organic phase, and crystallizing to obtain a white solid.
3. The method for recycling cannabidiol extraction process waste as claimed in claim 1 or 2, wherein the acidic solution of step (1) comprises any one or a combination of at least two of aqueous hydrobromic acid, hydrochloric acid, perchloric acid, hydroiodic acid or trichloroacetic acid;
preferably, the mass concentration of the hydrobromic acid aqueous solution is 30-50%;
preferably, the mass concentration of the hydrochloric acid aqueous solution is 30-38%;
preferably, the mass concentration of the perchloric acid aqueous solution is 30-72%;
preferably, the mass concentration of the hydriodic acid aqueous solution is 30-57%.
4. The method for recycling cannabidiol extraction process waste as claimed in any one of claims 1 to 3, wherein the temperature of the reaction of step (1) is 20-80 ℃;
preferably, the reaction time of step (1) is 3-10 h.
5. The recycling method of cannabidiol extraction process waste as claimed in any of claims 1-4, wherein the organic solvent of step (1) comprises ethyl acetate, isopropyl acetate or dichloromethane;
preferably, the temperature of the extraction in the step (1) is 20-30 ℃;
preferably, the washing of the organic phase in step (1) means: the organic phase is washed with sodium bicarbonate to a pH of 6-7 for the aqueous phase.
6. The recycling method of cannabidiol extraction process waste as claimed in any of claims 1-5, wherein the solvent of the alkaline solution of step (2) comprises ethanol, and the solute comprises any one or a combination of at least two of sodium hydroxide, potassium hydroxide, sodium tert-butoxide, potassium tert-butoxide or sodium ethoxide;
preferably, the mass concentration of the sodium hydroxide is 5-40%;
preferably, the mass concentration of the potassium hydroxide is 5-50%;
preferably, the mass concentration of the sodium tert-butoxide is 5-21%;
preferably, the mass concentration of the potassium tert-butoxide is 5-21%;
preferably, the mass concentration of the sodium ethoxide is 5-21%.
7. The method for recycling cannabidiol extraction process waste as claimed in any one of claims 1 to 6, wherein the temperature of the reaction of step (2) is 20-60 ℃;
preferably, the reaction time of the step (2) is 5-8 h.
8. The recycling method of cannabidiol extraction process waste as claimed in any one of claims 1 to 7, wherein the ethanol is removed by concentration and evaporation after the reaction of step (2);
preferably, the organic reagent of step (2) comprises dichloromethane, chloroform, methyl tert-butyl ether or isopropyl acetate;
preferably, said washing of the organic phase in step (2) means: washing the organic phase with a hydrochloric acid solution to a pH of 5-7 in the aqueous phase;
preferably, the crystallization of step (2) is performed using n-heptane, n-hexane, cyclohexane or petroleum ether.
9. The recycling method of cannabidiol extraction process waste as claimed in any one of claims 1 to 8, wherein the recycling method comprises the steps of:
(1) mixing the waste generated in the cannabidiol extraction process with an acidic solution at 20-80 ℃ for reaction for 3-10h, extracting with ethyl acetate at 20-30 ℃, washing the organic phase with sodium bicarbonate until the pH value of the aqueous phase is 6-7, and concentrating to obtain an oily intermediate;
(2) mixing the intermediate obtained in the step (1) with an alkaline solution at the temperature of 20-60 ℃ for reaction for 5-8h, extracting with dichloromethane, washing an organic phase with a hydrochloric acid solution until the pH value of a water phase is 5-7, and adding n-heptane for crystallization to obtain a white solid.
10. Use of a method of recycling cannabidiol extraction process waste as claimed in any of claims 1 to 9 in the post-treatment of waste produced in a cannabidiol extraction process.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911401594.6A CN111960923B (en) | 2019-12-30 | 2019-12-30 | Recycling method of cannabidiol extraction process waste and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911401594.6A CN111960923B (en) | 2019-12-30 | 2019-12-30 | Recycling method of cannabidiol extraction process waste and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111960923A true CN111960923A (en) | 2020-11-20 |
| CN111960923B CN111960923B (en) | 2023-01-03 |
Family
ID=73358234
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911401594.6A Active CN111960923B (en) | 2019-12-30 | 2019-12-30 | Recycling method of cannabidiol extraction process waste and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111960923B (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040143126A1 (en) * | 2001-03-07 | 2004-07-22 | Webster G. R. Barrie | Conversion of cbd to delta8-thc and delta9-thc |
| CN109568389A (en) * | 2017-09-29 | 2019-04-05 | 汉义生物科技（北京）有限公司 | A kind of preparation method of high-purity cannabinoids extract |
| CN109796311A (en) * | 2019-03-25 | 2019-05-24 | 黑龙江阳光工业大麻研究院 | A method of purifying cannabidiol from abandoned reagents |
| US20190160393A1 (en) * | 2017-11-27 | 2019-05-30 | Beleave Inc. | Extraction and purification of cannabinoid compounds |
-
2019
- 2019-12-30 CN CN201911401594.6A patent/CN111960923B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040143126A1 (en) * | 2001-03-07 | 2004-07-22 | Webster G. R. Barrie | Conversion of cbd to delta8-thc and delta9-thc |
| CN109568389A (en) * | 2017-09-29 | 2019-04-05 | 汉义生物科技（北京）有限公司 | A kind of preparation method of high-purity cannabinoids extract |
| US20190160393A1 (en) * | 2017-11-27 | 2019-05-30 | Beleave Inc. | Extraction and purification of cannabinoid compounds |
| CN109796311A (en) * | 2019-03-25 | 2019-05-24 | 黑龙江阳光工业大麻研究院 | A method of purifying cannabidiol from abandoned reagents |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111960923B (en) | 2023-01-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2003205844B2 (en) | Production of Delta 9 tetrahydrocannabinol | |
| CN105294801A (en) | Method for synthesizing, separating and determining obeticholic acid (OCA) isomer | |
| CN107501045B (en) | Method for separating and purifying butanetriol from fermentation liquor by using macroporous adsorption resin | |
| CN106226426B (en) | A kind of method that high performance liquid chromatography splits canagliflozin five-membered ring impurity enantiomer | |
| CN111960923B (en) | Recycling method of cannabidiol extraction process waste and application thereof | |
| CN102558103B (en) | Method for separating and purifying Orlistat | |
| CN103012352A (en) | Separation and purification method for mixed tocopherols | |
| CN111153775B (en) | Preparation method of triclosan methyl ester | |
| JP2010169676A (en) | Quantitative determination method of polychlorinated biphenyl | |
| CN1171857C (en) | Process for enriching and purifying capsaicin with macroporous adsorption resin | |
| CN105738506A (en) | Method for measuring degraded impurities in orlistat capsules | |
| CN105738533B (en) | method for separating and measuring 1, 2-propylene glycol enantiomer by gas chromatography | |
| CN110734443B (en) | Preparation method of tadalafil-related substance I | |
| CN1990483A (en) | Preparing process for Isolation of a plurality of isoflavones components in astragalus root | |
| CN113185527A (en) | Method for separating tetrandrine and tetrandrine | |
| JP2022532685A (en) | How to break down cannabinoids | |
| CN106186147B (en) | Recovery treatment method of high-concentration organic acid wastewater | |
| CN107216338B (en) | A method of isolating and purifying moxidectin | |
| CN110066256B (en) | Purification method of 5-chloro-2-methyl-4-isothiazolin-3-one | |
| CN102464635B (en) | Separation and purification method of arctigenin | |
| CN1182126C (en) | Process for preparing high purity taxol by column bromating method | |
| CN110960577A (en) | Preparation method of tertiary amine alkali component in rhizoma corydalis | |
| CN109485616B (en) | Etodolac photodegradation impurity and preparation method thereof | |
| Grellepois et al. | Facile conversion of dithioesters into carboxylic acids or esters using alkaline hydrogen peroxide | |
| Triñanes Romero et al. | Matrix solid-phase dispersion followed by liquid chromatographytandem mass spectrometry for the determination of selectiveciclooxygenase-2 inhibitors in sewage sludge samples |
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 |