IP Library Granted Patent US 11,091,455
Granted Patent B2
US 11,091,455 · App. 16/774,959 · Granted Aug 17, 2021

Process to extract and purify delta-9-tetrahydrocannabinol

Inventors: Lekhram Changoer (Ridderkerk, NL); Cornelis Herman Michel Van Der Loo (Groningen, NL); Erik Keller (Adorp, NL)
Assignee: APIRx Pharmaceutical USA, LLC
C07D311/80B01D11/0288
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Quick Facts
Patent No.
US 11,091,455
App. No.
16/774,959
Granted
Aug 17, 2021
Kind
B2
Abstract

Δ 9 -THC carboxylic acid is extracted from cannabis flowers using a first organic solvent, then separated using a second aqueous solvent. Δ 9 -THC carboxylic acid is converted to Δ 9 -THC carboxylic salt before being extracted by a third organic solvent and converted back to Δ 9 -THC carboxylic acid. Using a solvent swap, Δ 9 -THC carboxylic acid is decarboxylated and extracted again with an organic solvent prior to purification to give Δ 9 -THC.

Claims (30)

1. A method of producing Δ 9 -THC consisting essentially of:

extracting Δ 9 -THC carboxylic acid from cannabis flowers using heptane to obtain a heptane extract;

filtering the heptane extract to remove solid plant matter;

separating the Δ 9 -THC carboxylic acid from the heptane extract by contacting the heptane extract with sodium chloride water adjusted to a pH range of 13.2 to 13.4 using an inorganic base to form a liquid mixture;

stirring the liquid mixture; and

leaving the liquid mixture to settle;

wherein the liquid mixture forms three layers consisting of a first organic layer, a second oily layer, and third aqueous layer; and

separating out the oily layer from the other two layers by a separatory funnel to yield Δ 9 -THC.

2. The method of claim 1 , further consisting essentially of suspending the oily layer in an aqueous solvent consisting essentially of sodium chloride and an inorganic base to adjust the aqueous solvent to a pH of 13.2 to 13.4 to convert Δ 9 -THC carboxylic acid to Δ 9 -THC carboxylic salt.

3. The method of claim 2 , further consisting essentially of extracting Δ 9 -THC carboxylic salt with an organic solvent.

4. The method of claim 3 , wherein the organic solvent is tert-butyl methyl ether.

5. The method of claim 3 , further consisting essentially of converting the Δ 9 -THC carboxylic acid salt in the organic solvent back to Δ 9 -THC carboxylic acid by adding an aqueous solvent consisting essentially of sodium chloride and an inorganic base to adjust the aqueous solvent to a pH of 13.2 to 13.4 and a strong inorganic acid into the Δ 9 -THC carboxylic salt in organic solvent mixture.

6. The method of claim 5 , further consisting essentially of:

washing the resulting mixture with a sodium chloride water solution to form an organic solvent layer and an aqueous layer; and

separating the organic solvent layer from the aqueous layer, wherein the organic solvent layer consists essentially of Δ 9 -THC carboxylic acid in water and organic solvent.

7. The method of claim 6 , further consisting essentially of:

removing water from the Δ 9 -THC carboxylic acid in water and organic solvent mixture using Na 2 SO 4 ;

removing the organic solvent using vacuum to give a crude solid consisting essentially of Δ 9 -THC carboxylic acid;

dissolving the solid in pentane;

treating the crude solid containing Δ 9 -THC carboxylic acid dissolved in pentane with active carbon to remove non-THC cannabinoids;

removing the pentane using vacuum; and

filtering to obtain a Δ 9 -THC carboxylic acid solid.

8. The method of claim 7 , further consisting essentially of:

dissolving the Δ 9 -THC carboxylic acid solid with an alcohol and adding the mixture into boiling water;

heating the mixture to between 80° C. and 100° C. for at least 40 minutes; and

cooling the mixture to room temperature and adding a sodium chloride solution into the mixture;

wherein the Δ 9 -THC carboxylic acid is decarboxylated to convert Δ 9 -THC carboxylic acid to Δ 9 -THC.

9. The method of claim 8 , wherein the alcohol is ethanol, isopropyl alcohol, propyl alcohol, or butyl alcohol.

10. The method of claim 8 , further consisting essentially of extracting the Δ 9 -THC using n-pentane 1 to 3 times.

11. The method of claim 10 , further consisting essentially of purifying the Δ 9 -THC by removing water using Na 2 SO 4 and removing n-pentane by a vacuum.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 16, 2023
From: CHANGOER, LEKHRAM; KELLER, ERIK; VAN DER LOO, CORNELIS HERMAN MICHEL
To: AXIM BIOTECHNOLOGIES, INC
Reel/Frame 063694/0730 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 26, 2020
From: AXIM BIOTECHNOLOGIES, INC.
To: APIRX PHARMACEUTICAL USA, LLC
Reel/Frame 052752/0519 →
Continuity (5)
Continuation 16272817 · Feb 11, 2019
Continuation 16052150 · Aug 1, 2018
Continuation 15146668 · May 4, 2016
Provisional Application 62158075 · May 7, 2015
Related Publication 20200165219A1 · May 28, 2020