Process for producing an extract containing tetrahydrocannabinol and cannabidiol from cannabis plant material, and cannabis extracts

Abstract

The invention relates to a method for producing an extract from cannabis plant matter, containing tetrahydrocannabinol, cannabidiol and optionally the carboxylic acids thereof. According to said method, the dried plant matter is ground and subjected to a CO2 extraction and the primary extract obtained is separated. The invention method permits Δ8 or Δ9 tetrahydrocannabinol to be selectively obtained both from industrial hemp and from drug-producing hemp, optionally after dissolving the primary extract in ethanol, separating undesirable waxes and removing the solvent under reduced pressure.

The invention claimed is: 
     
       1. A process for producing cannabidiol from a primary extract from industrial hemp plant material containing tetrahydrocannabinol and cannabidiol and optionally the carboxylic acids thereof, wherein said primary extract is obtained by a process comprising
 extracting dried comminuted industrial hemp plant material by means of CO 2      (a) under supercritical pressure and temperature conditions at a temperature in a range of approx. 31° C. to 80° C. and at a pressure in a range of approx 75 bar or 500 bar, or   (b) in liquefied form in the subcritical range at a temperature of approx. 20° C. to 30° C. and a supercritical pressure of approx. 100 bar to 350 bar; or   (c) in liquefied form under subcritical pressure and temperature conditions; and   separating the obtained primary extract out under subcritical conditions or under conditions subcritical in terms of pressure and supercritical in terms of temperature; and   wherein said primary extract contains reduced proportions of at least monoterpene and sesquiterpene hydrocarbons, alkaloids, flavonoids and chlorophylls; and   wherein process for producing cannabidiol from a primary extract comprises   decarboxylating cannabidiolic acid and tetrahydrocannabidiolic acid in said primary extract into cannabidiol and tetrahydrocannabinol through increase in temperature; and   dissolving the decarboxylated primary extract in the CO 2  extracting agent used, and in this condition treating by means of a high-pressure vessel charged with a catalyst for anellation of cannabidiol into tetrahydrocannabinol and a water-binding agent, wherein cannabidiol is reacted to give tetrahydrocannabinol; and   separating the product enriched in tetrahydrocannabinol at pressure and temperature conditions subcritical for CO 2 .   
     
     
       2. A process for producing cannabidiol from a primary extract from industrial hemp plant material containing tetrahydrocannabinol and cannabidiol
 and optionally the carboxylic acids thereof, wherein said primary extract is obtained by a process comprising
 extracting dried comminuted industrial hemp plant material by means of CO 2    
   (a) under supercritical pressure and temperature conditions at a temperature in a range of approx. 31° C. to 80° C. and at a pressure in a range of approx. 75 bar or 500 bar, or   (b) in the subcritical range at a temperature of approx. 20° C. to 30° C. and a supercritical pressure of approx. 100 bar to 350 bar; or   (c) under subcritical pressure and temperature conditions; and
 separating the obtained primary extract out under subcritical conditions or under conditions subcritical in terms of pressure and supercritical in terms of temperature; and 
 wherein said primary extract contains reduced proportions of at least monoterpene and sesquiterpene hydrocarbons, alkaloids, flavonoids and chlorophylls; and 
 wherein process for producing cannabidiol from a primary extract comprises 
 decarboxylating cannabidiolic acid and tetrahydrocannabidiolic acid in said primary extract into cannabidiol and tetrahydrocannabinol through increase in temperature; and 
 subsequently separating the cannabidiol through column chromatography on silica gel or preparative high-pressure liquid chromatography. 
   
     
     
       3. A process for producing an extract containing tetrahydrocannabinol, cannabidiol and optionally the carboxylic acids thereof from dried comminuted industrial hemp plant material, comprising
 (1) subjecting said plant material to a stream of CO 2  in liquefied form in the subcritical range at a temperature of approx. 20° C. to 30° C. and a supercritical pressure of approx. 100 bar to 350 bar, to form an extract-loaded CO 2 ;
 (1a) under supercritical pressure and temperature conditions at a temperature in a range of approx. 31° C. to 80° C. and at a pressure in a range of approx. 75 bar or 500 bar, or 
 (1b) in liquefied form in the subcritical range at a temperature of approx. 20° C. to 30° C. and a supercritical pressure of approx. 100 bar to 350 bar; or 
 (1c) in liquefied found under subcritical pressure and temperature conditions; to extract cannabinoid components; 
 
 (2) reducing the pressure and/or temperature of the extract loaded extract-loaded CO 2  in at least two steps, wherein
 (2a) in a first step pressure and/or temperature are reduced whereby monoterpenes and sesquiterpenes are separated from tetrahydrocannabinol and cannabidiol by differential solubility, and  
 (2b) in a subsequent step pressure is reduced to a pressure subcritical for CO 2 , whereby tetrahydrocannabinol and cannabidiol are separated from said CO 2 , and  
 
 (2c)(3) subjecting the CO 2  extracted from step ( 2 b) to increased pressure and temperature and recycling said CO 2  to step (1). 
 
     
     
       4. The process of  claim 3 , wherein step (2) further comprises exposure to adsorbent or absorbent to remove alkaloids, flavinoids, and chlorophylls. 
     
     
       5. A process for producing an extract containing tetrahydrocannabinol, cannabidiol and optionally the carboxylic acids thereof from dried comminuted industrial hemp plant material, comprising:
 (1) subjecting the dried comminuted industrial hemp to a stream of CO 2  under a supercritical pressure and temperature condition, wherein the CO 2  has a temperature of approximately 31° C. to 80° C. and a pressure of approximately 75 bar to 500 bar to form an extract-loaded CO 2 ;   (2) reducing the pressure of the extract-loaded CO 2  in at least two steps, comprising:
 (2a) first reducing the pressure to separate monoterpenes and sesquiterpenes from tetrahydrocannabinol and cannabidiol by differential solubility, and 
 (2b) subsequently reducing the pressure within the subcritical range for CO 2  to remove a remaining extract from the CO 2  to produce a substantially extract-free CO 2 ; and 
   (3) subjecting the extract-free CO 2  from step (2) to increased pressure and temperature and recycling said CO 2  to step (1).   
     
     
       6. The process of claim 5, wherein the CO 2  in step (1) has a temperature of approximately 45° C. to 65° C. and a pressure of approximately 100 bar to 350 bar. 
     
     
       7. The process of claim 5, further comprising:
 dissolving a first extract created during step (2) in a cold solution comprising a solvent to precipitate waxes;   separating the precipitated waxes by filtration; and   removing the solvent from the solution to form a second extract.   
     
     
       8. The process of claim 7, wherein the solvent is ethanol. 
     
     
       9. The process according to claim 5, further comprising a step of decarboxylating the carboxylic acids of tetrahydrocannabinol and cannabidiol. 
     
     
       10. The process according to claim 5, wherein an entraining agent is added to the stream of CO 2 . 
     
     
       11. The process according to claim 10, wherein the entraining agent is propane, butane, ethanol or water.  
     
     
       12. A process for producing an extract containing tetrahydrocannabinol, cannabidiol and optionally the carboxylic acids thereof from dried comminuted industrial hemp plant material, comprising:
 (1) subjecting the dried comminuted industrial hemp to a stream of CO 2  in a liquified form under a supercritical pressure and subcritical temperature condition, wherein the CO 2  has a temperature of approximately 20° C. to 30° C. and a pressure of approximately 100 bar to 350 bar to form an extract-loaded CO 2 ;   (2) reducing the pressure of the extract-loaded CO 2  in at least two steps, comprising:
 (2a) first reducing the pressure to separate monoterpenes and sesquiterpenes from tetrahydrocannabinol and cannabidiol by differential solubility, and 
 (2b) subsequently reducing the pressure within the subcritical range for CO 2  to remove a remaining extract from the CO 2  to produce a substantially extract-free CO 2 ; and 
   (3) subjecting the extract-free CO 2  from step (2) to increased pressure and temperature and recycling said CO 2  to step (1).   
     
     
       13. The process of claim 12, further comprising:
 dissolving a first extract created during step (2) in a cold solution comprising a solvent to precipitate waxes;   separating the precipitated waxes by filtration; and   removing the solvent from the solution to form a second extract.   
     
     
       14. The process of claim 13, wherein the solvent is ethanol. 
     
     
       15. The process according to claim 12, further comprising a step of decarboxylating the carboxylic acids of tetrahydrocannabinol and cannabidiol. 
     
     
       16. The process according to claim 12, wherein an entraining agent is added to the stream of CO 2 . 
     
     
       17. The process according to claim 16, wherein the entraining agent is propane, butane, ethanol or water. 
     
     
       18. A process for producing an extract containing tetrahydrocannabinol, cannabidiol and optionally the carboxylic acids thereof from dried comminuted industrial hemp plant material, comprising:
 (1) subjecting the dried comminuted industrial hemp to a stream of CO 2  in a liquefied form under a subcritical pressure and temperature condition to form an extract-loaded CO 2 ;   (2) reducing the pressure of the extract-loaded CO 2  in at least two steps, comprising:
 (2a) first reducing the pressure to separate monoterpenes and sesquiterpenes from tetrahydrocannabinol and cannabidiol by differential solubility, and 
 (2b) subsequently reducing the pressure within the subcritical range for CO 2  to remove a remaining extract from the CO 2  to produce a substantially extract-free CO 2 ; and 
   (3) subjecting the extract-free CO 2  from step (2) to increased pressure and temperature and recycling said CO 2  to step (1).   
     
     
       19. The process of claim 18, further comprising:
 dissolving a first extract created during step (2) in a cold solution comprising a solvent to precipitate waxes;   separating the precipitated waxes by filtration; and   removing the solvent from the solution to form a second extract.   
     
     
       20. The process of claim 19, wherein the solvent is ethanol. 
     
     
       21. The process according to claim 18, further comprising a step of decarboxylating the carboxylic acids of tetrahydrocannabinol and cannabidiol. 
     
     
       22. The process according to claim 18, wherein an entraining agent is added to the stream of CO 2 . 
     
     
       23. The process according to claim 22, wherein the entraining agent is propane, butane, ethanol or water. 
     
     
       24. A process for producing an extract containing tetrahydrocannabinol, cannabidiol and optionally the carboxylic acids thereof from dried comminuted industrial hemp plant material, comprising:
 (1) subjecting the dried comminuted industrial hemp to a stream of CO 2  in a liquified form under a supercritical pressure and subcritical temperature condition, wherein the CO 2  has a temperature of approximately 20° C. to 30° C. and a pressure of approximately 100 bar to 350 bar to form an extract-loaded CO 2 ;   (2) reducing the pressure and/or temperature of the extract-loaded CO 2  in at least two steps, comprising:
 (2a) first reducing the pressure and/or temperature to separate monoterpenes and sesquiterpenes from tetrahydrocannabinol and cannabidiol by differential solubility, and 
 (2b) subsequently reducing the pressure within the subcritical range for CO 2  to remove a remaining extract from the CO 2  to produce a substantially extract-free CO 2 ; and 
   (3) subjecting the extract-free CO 2  from step (2) to increased pressure and temperature and recycling said CO 2  to step (1).   
     
     
       25. A process for producing an extract containing tetrahydrocannabinol, cannabidiol and optionally the carboxylic acids thereof from dried comminuted industrial hemp plant material, comprising:
 (1) subjecting the dried comminuted industrial hemp to a stream of CO 2  in a liquified form under a supercritical pressure and subcritical temperature condition, wherein the CO 2  has a temperature of approximately 20° C. to 30° C. and a pressure of approximately 100 bar to 350 bar to form an extract-loaded CO 2 ;   (2) reducing the pressure of the extract-loaded CO 2  in at least two steps, comprising:
 (2a) first reducing the pressure to separate monoterpenes and sesquiterpenes from tetrahydrocannabinol and cannabidiol by differential solubility, and 
 (2b) subsequently reducing the pressure within the subcritical range for CO 2  to remove a remaining extract from the CO 2  to produce a substantially extract-free CO 2 ; 
   (3) subjecting the extract-free CO 2  from step (2) to increased pressure and temperature and recycling said CO 2  to step (1);   (4) dissolving a first extract created during step (2) in a cold solution comprising a solvent to precipitate waxes;   (5) separating the precipitated waxes by filtration; and   (6) removing the solvent from the solution to form a second extract; and   wherein the process further comprising a step of decarboxylating the carboxylic acids of tetrahydrocannabinol and cannabidiol.   
     
     
       26. The process of claim 3, further comprising:
 dissolving a first extract created during step (2) in a cold solution comprising a solvent to precipitate waxes;   separating the precipitated waxes by filtration; and   removing the solvent from the solution to form a second extract.   
     
     
       27. The process of claim 26, wherein the solvent is ethanol. 
     
     
       28. The process according to claim 3, further comprising a step of decarboxylating the carboxylic acids of tetrahydrocannabinol and cannabidiol.