Patent US10647691

Method for purifying cannabinoid compounds
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US10647691

1. A method for purifying a cannabinoid compound obtained by enantiopure synthesis, wherein the cannabinoid compound is cannabidiol, trans-(−)-delta-9-tetrahydrocannabinol, cannabidivarin, trans-(−)-delta-9-tetrahydrocannabivarin, or cannabigerol, the method comprising: (4) (2)

i) providing a mixture comprising the cannabinoid compound obtained by enantiopure synthesis and one or more of its isomers and optionally one or more further organic compounds, and

ii) simultaneously, a) continuously feeding the mixture of step i) through a feed port into a simulated moving bed chromatographic apparatus comprising at least four columns connected in series and containing a stationary phase, and

b) continuously feeding eluant into the apparatus through an eluant port, and

c) continuously withdrawing the extract through an extract port, and

d) continuously withdrawing the raffinate through a raffinate port, wherein the extract and/or the raffinate respectively comprises the purified cannabinoid compound and less than 100 ppm in total of any isomer(s) of the purified cannabinoid compound present in step i).

2. The method according to claim 1, additionally comprising: (1) (1)

3. The method according to claim 1, wherein the cannabinoid compound is trans-(−)-delta-9-tetrahydrocannabinol or trans-(−)-delta-9-tetrahydrocannabivarin. (0)

4. The method according to claim 1, wherein step i) includes conversion of menthadienol with an olivetolic acid ester to a cannabidiolic acid ester of formula (IX) (3) (1)

wherein Y is an organic residue.

5. The method according to claim 4, wherein step i) comprises the conversion of a cannabidiolic acid ester of formula (IX), wherein Y is an organic residue, with an alcohol of the formula HO-X, wherein X is an aliphatic residue with one, two, three or more than three hydroxyl groups and the total number of C-atoms in the aliphatic residue X is not greater than 15, wherein Y is different from X and selected such that the alcohol of formula HO-Y, which is generated during the conversion, boils at a lower temperature at 1013 hPa than the alcohol of formula HO-X. (1) (0)

8. The method according to claim 4, wherein the mixture comprising the cannabinoid compound in step i) comprises the one or more further organic compound(s), and the one or more further organic compound(s) comprises olivetol. (1) (0)

15. The method of claim 4, wherein the conversion is carried out in a continuous process. (0)

10. The method according to claim 1, wherein step i) comprises the conversion of menthadienol of formula (I) with a divarinic acid ester of formula (IV), to an ester of formula (V), (2) (0)

20. A method for purifying a cannabinoid compound obtained by enantiopure synthesis, wherein the cannabinoid compound is trans-(−)-delta-9-tetrahydrocannabinol or trans-(−)-delta-9-tetrahydrocannabivarin, the method comprising: (0) (3)

i) providing a mixture comprising the cannabinoid compound obtained by enantiopure synthesis, one or more of its isomers, and one or more further organic compounds, and

b) continuously feeding eluant into the apparatus through an eluant port, and

c) continuously withdrawing the extract through an extract port, and

d) continuously withdrawing the raffinate through a raffinate port, and

iii) subjecting the extract and/or the raffinate comprising the purified cannabinoid compound to one, two, or more further extraction step(s), wherein the extract and/or the raffinate respectively comprises the purified cannabinoid compound, less than 100 ppm in total of any isomer(s) of the purified cannabinoid compound present in step i), and less than 100 ppm in total of olivetol.

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Patent US10647691

Method for purifying cannabinoid compounds

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