CN111960923B - 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
- CN111960923B CN111960923B CN201911401594.6A CN201911401594A CN111960923B CN 111960923 B CN111960923 B CN 111960923B CN 201911401594 A CN201911401594 A CN 201911401594A CN 111960923 B CN111960923 B CN 111960923B
- Authority
- CN
- China
- Prior art keywords
- extraction process
- recycling
- process waste
- cannabidiol
- waste
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
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
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 sativa is one of the main toxic components of Cannabis sativa plants and products thereof, which cause addiction of abusers and personal injury, and can cause adverse reactions such as hallucinations, convulsion, emesis, and multiple sclerosis recurrence. THC is a lipophilic, hydrophobic, viscous oil with a volatility, pKa =10.6, is usually present in cannabis plants as a mixture of monocarboxylic acids, and is easily decomposed 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 process of extracting the cannabinoids, the cannabinoids are extracted along with other substances, and in order to prevent the cannabinoids from being taken as drugs or circulating in other illegal ways, the cannabinoids need to be thoroughly destroyed after being 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 and pharmaceutical effects of anticonvulsant, antibacterial, anti-inflammatory, anti-anesthetic and nervous system protection; 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, the control of the flow direction of THC and the control of the impurity content of CBD are one of the difficulties of the current extraction process of industrial hemp, and no better treatment method exists at present, so if the THC in the industrial hemp extraction waste can be converted into the 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 recycling 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) And (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 in the range can be selected, which are 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, said 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 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 in the range can be selected, which are 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 reduces the rate of reaction or renders the reaction impossible.
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, which are not described in detail herein.
The temperature of the reaction is specifically selected in the range of 20-60 ℃ because exceeding this temperature increases the reaction by-products, and below this temperature the reaction rate decreases.
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 by hydrochloric acid solution until the pH value of the water phase is 5-7, so that the residue of alkali is reduced and impurities are removed. For example, pH =5, pH =5.5, pH =6, pH =6.5, pH =7, or the like.
Preferably, the crystallization of step (2) is a crystallization 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 20-60 ℃ for reaction for 5-8h, extracting with dichloromethane, washing the organic phase with a hydrochloric acid solution until the pH value of the water phase is 5-7, and adding n-heptane for crystallization to obtain a white solid.
On the other hand, the invention provides the application of the recycling method of the cannabidiol extraction process waste in the post-treatment of the waste generated in 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 waste to react with the acidic solution and the alkaline solution in sequence, so that the content of the adverse component tetrahydrocannabinol (THC for short) in the waste is greatly reduced, and the content of the beneficial component cannabidiol (CBD for short) 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.
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 waste products 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; the detection wavelength was 210nm.
Preparation of control solutions: accurately weighing cannabidiol CBD reference substance, adding ethanol (1); the tetrahydrocannabinol THC control was weighed precisely, and added with methanol (1).
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), carrying out ultrasonic treatment for 10min, adding acetonitrile-water (1) for diluting to a scale, shaking, filtering with a microporous filter membrane (0.45 pm), and taking a subsequent filtrate to obtain the product.
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 with ethyl acetate at 25 ℃, washing the organic phase with sodium bicarbonate until the pH value of the aqueous 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 by HPLC that the reaction is complete, cooling to 25 ℃, concentrating and distilling off 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, the THC content in the waste before treatment is 56.8%, and the CBD content is 2.5% by calculation by adopting a peak area normalization method; the THC content of the treated product is 3.6%, the CBD content is 82.8%, and the liquid chromatogram is shown in figures 1-3 (figure 1 is the chromatogram of cannabidiol CBD reference substance; figure 2 is the high performance liquid chromatogram of the sample before treatment, figure 3 is the high performance liquid chromatogram of the sample after treatment; the peak emergence time of THC is about 14.9min, and the peak emergence time of CBD 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 completion by TLC, extracting with ethyl acetate at 20 ℃, washing the organic phase with sodium bicarbonate until the pH value of the aqueous phase is 7, and concentrating the organic phase to obtain oil;
(2) Mixing the oily substance 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 distilling off 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 7, and adding N-heptane for crystallization to obtain white solid.
Through high performance liquid chromatography detection, the THC content in the waste before treatment is 56.8%, and the CBD content is 2.5% by calculation by adopting a peak area normalization method; the THC content of the treated product is 4.1%, and the CBD content is 80.6%.
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 reaction for 8h, detecting by HPLC that the reaction is complete, 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 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 reaction for 8h, monitoring by TLC to complete the reaction, 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 7h, detecting complete reaction by HPLC, cooling to 25 ℃, concentrating and distilling off 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 3.7%, and the CBD content is 81.6%.
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 a recycling method of cannabidiol extraction process waste and its application, but the present invention is not limited to the above examples, which does not mean that the present invention must be implemented by the above examples. 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, in the above embodiments, the various features described in the above embodiments may be combined in any suitable manner, and in order to avoid unnecessary repetition, the present invention does not separately describe various possible combinations.
Claims (25)
1. A recycling method of cannabidiol extraction process waste is characterized by comprising the following steps:
(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.
2. The method for recycling cannabidiol extraction process waste of claim 1, wherein the acidic solution of step (1) comprises any one of or a combination of at least two of aqueous hydrobromic acid, aqueous hydrochloric acid, aqueous perchloric acid, aqueous hydroiodic acid, and trichloroacetic acid.
3. The method of recycling cannabidiol extraction process waste of claim 2, wherein the aqueous hydrobromic acid solution has a mass concentration of 30-50%.
4. The method of recycling cannabidiol extraction process waste as claimed in claim 2, wherein the aqueous hydrochloric acid solution has a mass concentration of 30-38%.
5. The method for recycling cannabidiol extraction process waste as claimed in claim 2, wherein the perchloric acid aqueous solution has a mass concentration of 30-72%.
6. The method of recycling cannabidiol extraction process waste as claimed in claim 2, wherein the hydriodic acid aqueous solution has a mass concentration of 30-57%.
7. The method for recycling cannabidiol extraction process waste as claimed in claim 1, wherein the temperature of the reaction in step (1) is 20-80 ℃.
8. The method for recycling cannabidiol extraction process waste as claimed in claim 1, wherein the reaction time of step (1) is 3-10h.
9. The method for recycling cannabidiol extraction process waste of claim 1, wherein the organic solvent of step (1) comprises ethyl acetate, isopropyl acetate or dichloromethane.
10. The method for recycling cannabidiol extraction process waste as claimed in claim 1, wherein the temperature of the extraction in step (1) is 20-30 ℃.
11. The method of recycling cannabidiol extraction process waste of claim 1, wherein the washing organic phase of step (1) is: the organic phase is washed with sodium bicarbonate to a pH of 6-7 for the aqueous phase.
12. The method of recycling cannabidiol extraction process waste of claim 1, 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.
13. The method of recycling cannabidiol extraction process waste of claim 12, wherein the sodium hydroxide has a mass concentration of 5-40%.
14. The method of recycling cannabidiol extraction process waste of claim 12, wherein the potassium hydroxide is present in a mass concentration of 5-50%.
15. The method of recycling cannabidiol extraction process waste of claim 12, wherein the mass concentration of the sodium tert-butoxide is 5-21%.
16. The method of recycling cannabidiol extraction process waste of claim 12, wherein the mass concentration of potassium tert-butoxide is 5-21%.
17. The method of recycling cannabidiol extraction process waste of claim 12, wherein the mass concentration of sodium ethoxide is 5-21%.
18. The recycling method of cannabidiol extraction process waste as claimed in claim 1, wherein the reaction temperature in step (2) is 20-60 ℃.
19. The method for recycling cannabidiol extraction process waste as claimed in claim 1, wherein the reaction time of step (2) is 5-8h.
20. The method for recycling cannabidiol extraction process waste as claimed in claim 1, wherein the ethanol is removed by concentration and evaporation after the reaction in step (2) is completed.
21. The method of recycling cannabidiol extraction process waste of claim 1, wherein the organic reagent of step (2) comprises dichloromethane, chloroform, methyl tert-butyl ether or isopropyl acetate.
22. The method of recycling cannabidiol extraction process waste of claim 1, wherein the washing organic phase of step (2) is: the organic phase is washed with a hydrochloric acid solution to a pH of 5-7 of the aqueous phase.
23. The method for recycling cannabidiol extraction process waste of claim 1, wherein the crystallization in step (2) is performed using n-heptane, n-hexane, cyclohexane, or petroleum ether.
24. 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 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.
25. Use of a method of recycling cannabidiol extraction process waste as claimed in any of claims 1 to 24 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 CN111960923A (en) | 2020-11-20 |
| CN111960923B true 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 (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7399872B2 (en) * | 2001-03-07 | 2008-07-15 | Webster G R Barrie | Conversion of CBD to Δ8-THC and Δ9-THC |
| CA3083622A1 (en) * | 2017-11-27 | 2019-05-31 | Beleave Inc. | Extraction and purification of cannabinoid compounds |
-
2019
- 2019-12-30 CN CN201911401594.6A patent/CN111960923B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111960923A (en) | 2020-11-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7524881B2 (en) | Production of Δ 9 tetrahydrocannabinol | |
| CN105294801A (en) | Method for synthesizing, separating and determining obeticholic acid (OCA) isomer | |
| CN102228499B (en) | Method for separating naphthoquinone active ingredients from sinkiang arnebia root | |
| Wei et al. | Rapid and sensitive determination of multiple endocrine‐disrupting chemicals by ultrasound‐assisted in situ derivatization dispersive liquid–liquid microextraction coupled with ultra‐high‐performance liquid chromatography/tandem mass spectrometry | |
| CN104880523A (en) | Method for determining nitrofuran metabolites in bee wax through high performance liquid chromatography tandem mass spectrometry | |
| CN104458925B (en) | The detection method of 2,3,4,7,8-PeCDF in incinerator flying dust and flue gas | |
| CN101402577B (en) | Method for extracting and separating levorotation-synephrine from green tangerine orange peel | |
| CN111960923B (en) | Recycling method of cannabidiol extraction process waste and application thereof | |
| CN106226426B (en) | A kind of method that high performance liquid chromatography splits canagliflozin five-membered ring impurity enantiomer | |
| CN101832992A (en) | Method for measuring residual erythromycin in environment by using hydrophilic ionic-liquid aqueous two-phase system | |
| CN104880522A (en) | Method for determining residual quantity of chloramphenicol in bee wax by n-hexane pre-treatment-high performance liquid chromatography-tandem mass spectrometry | |
| CN105738506B (en) | A kind of measure the method for degradation impurity in orlistat capsule | |
| CN106706769B (en) | Separation and determination method of empagliflozin and optical isomer thereof | |
| CN105738533B (en) | method for separating and measuring 1, 2-propylene glycol enantiomer by gas chromatography | |
| CN103207245A (en) | Method of separating and determining dutasteride intermediate and optical isomers thereof by using liquid chromatography | |
| CN113185527B (en) | Method for separating tetrandrine and tetrandrine | |
| CN1990483A (en) | Preparing process for Isolation of a plurality of isoflavones components in astragalus root | |
| CN103389356A (en) | Method for detecting polyether antibiotics in feed | |
| CN102659573A (en) | Preparation method for 7-carbonyl group-8, 15-isopimaric acid | |
| CN107976506A (en) | A kind of detection method of Austria's shellfish cholic acid in relation to material | |
| CN112209882A (en) | Levoornidazole impurity C and preparation method and application thereof | |
| CN107941937A (en) | A kind of method for separating and analyzing of oat alkaloid D and dihydro avenine D | |
| CN107216338B (en) | A method of isolating and purifying moxidectin | |
| CN1182126C (en) | Process for preparing high purity taxol by column bromating method | |
| CN102464635B (en) | Separation and purification method of arctigenin |
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 |