IP Library › Granted Patent US 11,851,415
Granted Patent B2
US 11,851,415 · App. 16/840,247 · Granted Dec 26, 2023

Continuous isolation of cannabidiol and cannabinoids and conversion of cannabidiol to delta 8-tetrahydrocannabinol and delta 9-tetrahydrocannabinol

Inventors: Mark G. Tegen (Seattle, WA); Joon Cho (Wilsonville, OR)
Assignee: Cleen Technology Inc.
C07D301/32C07D311/86
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Quick Facts
Patent No.
US 11,851,415
App. No.
16/840,247
Granted
Dec 26, 2023
Kind
B2
Abstract

In alternative embodiments, provided are processes for obtaining or purifying a substantially pure Δ 8 tetrahydrocannabinol (Δ 8 THC) and/or Δ 9 tetrahydrocannabinol (Δ 9 THC) and optionally a plurality of cannabinoids or terpenes from a natural or a synthetic source, wherein the natural or the synthetic source comprises a cannabidiol (CBD) and optionally a plurality of cannabinoids or terpenes. Also provided are processes comprising the continuous isolation and purification of cannabinoids or terpenes, and further isomerization of the purified cannabidiol to Δ 8 tetrahydrocannabinol (Δ 8 THC) and Δ 9 tetrahydrocannabinol (Δ 9 THC). In alternative embodiments, provided are processes for converting Δ8-THC into Δ 9 -THC. In alternative embodiments, provided are processes for the industrial scale continuous isolation and purification of cannabinoids and further isomerization of the purified cannabidiol to Δ 9 -THC.

Claims (30)

1. A method or process for obtaining or purifying a composition comprising a substantially pure Δ 8 -THC and a substantially pure Δ 9 -THC from a natural or a synthetic source, wherein the natural or the synthetic source comprises Δ 8 -THC and Δ 9 -THC,

the method comprising:

(a) obtaining or being provided a first extract, aliquot or sample of the natural or synthetic source, wherein the first extract, aliquot or sample comprises a cannabidiol (CBD) from the natural or the synthetic source;

(b) dissolving the first extract, aliquot or sample in a first reaction solvent;

(c) adding a catalyst to the first extract, aliquot or sample and the first reaction solvent to generate a first reaction mixture, wherein the catalyst includes p-toluenesulfonic acid and the catalyst is free of boron trifluoride and free of boron trifluoride diethyl etherate;

(d) reacting the first extract, aliquot or sample, with the catalyst and the first reaction solvent, under reaction conditions at a temperature of about 5° C. for between about 1 to 30 hours;

(e) adding a neutralizing agent to the first reaction mixture;

(f) removing or substantially removing most or all of the catalyst and the neutralizing agent from the first reaction mixture to generate a first reaction product;

(g) dissolving the first reaction product in a second solvent;

(h) loading the dissolved first reaction product onto a first chromatography column, wherein the Δ 8 -THC and Δ 9 -THC are reversibly bound to the first chromatography column; and

(i) eluting the dissolved first reaction product from the first column with an or at least one elution solution,

thereby obtaining or purifying the composition comprising the substantially pure Δ 9 -THC and the substantially pure Δ 8 -THC.

2. The method or process of claim 1 , further comprising dissolving ormixing in or adding the composition in a solvent to make a mixture of solvent and Δ 9 THC and Δ 8 THC, and loading the mixture onto a second chromatography column, and

eluting the dissolved composition from the second column with an elution solution,

thereby obtaining or purifying a substantially pure Δ 9 THC and Δ 8 THC.

3. The method or process of claim 2 , wherein the second chromatography column is the same column or the same type of column as the first chromatography column.

4. The method or process of claim 1 , wherein the natural source comprises a plant, algal, yeast, lichen or a microbial material, or a material derived from a plant source or plant, algal, yeast, lichen or microbial material.

5. The method or process of claim 1 , wherein the catalyst is added before, simultaneous with, or after addition of the first reaction solvent to the first extract, aliquot, or sample.

6. The method or process of claim 1 , wherein the reaction conditions comprise about 4to 24 hours.

7. The method or process of claim 1 , wherein the reaction conditions comprise about 6 to 15 hours.

8. The method or process of claim 1 , wherein the reacting converts the CBD to a mixture comprising (unreacted) CBD, Δ 8 -THC, and Δ 9 -THC.

9. The method or process of claim 1 , further comprising removing all or substantially most of the first reaction solvent, thereby leaving a first reaction product comprising (unreacted) CBD, Δ 8 -THC, and Δ 9 -THC.

10. The method or process of claim 1 , wherein the second solvent is the same as the first reaction solvent.

11. The method or process of claim 1 , wherein the first chromatography column is a normal phase chromatography column or a reverse phase chromatography column.

12. The method or process of claim 1 , wherein the eluting comprises use of a gradient elution process and the substantially pure Δ 9 -THC and the substantially pure Δ 8 -THC are separately collected in different or separate gradient elution fractions.

13. The method or process of claim 1 , wherein the eluting comprises use of an isocratic simulated moving bed (SMB) elution process and the substantially pure Δ 9 -THC and the substantially pure Δ 8 -THC are separately collected in different or separate elution fractions.

14. The method or process of claim 1 , wherein the natural or the synthetic source further comprises at least one terpene.

15. The method or process of claim 14 , wherein the CBD is reversibly bound to the first chromatography column in (h).

16. The method or process of claim 15 , wherein the CBD is eluted before the Δ 8 -THC and Δ 9 -THC.

17. The method or process of claim 1 , further comprising removing the first reaction solvent after (f) and before (g).

Assignments (7)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 7, 2025
From: CLEEN TECHNOLOGY INC.
To: SALADINO, PETER
Reel/Frame 069771/0831 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 7, 2025
From: SALADINO, PETER
To: ATLAS INVESTMENTS SEATTLE LLC
Reel/Frame 069772/0349 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 7, 2025
From: ATLAS INVESTMENTS SEATTLE LLC
To: MOLO TECHNOLOGIES LLC
Reel/Frame 069774/0041 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 20, 2023
From: SOCATI TECHNOLOGIES - OREGON, LLC
To: CLEEN TECHNOLOGY INC.
Reel/Frame 064323/0294 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 4, 2020
From: TEGEN, MARK G.; CHO, JOON
To: SOCATI TECHNOLOGIES LLC
Reel/Frame 052565/0596 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 4, 2020
From: SOCATI TECHNOLOGIES LLC
To: SOCATI TECHNOLOGIES - OREGON, LLC
Reel/Frame 052565/0634 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 2, 2020
From: SOCATI TECHNOLOGIES LLC
To: SOCATI TECHNOLOGIES - OREGON, LLC
Reel/Frame 052556/0252 →
Continuity (9)
Continuation In Part 16672047 · Nov 1, 2019
Division 16388182 · Apr 18, 2019
Continuation PCTUS2019021138 · Mar 7, 2019
Provisional Application 62715545 · Aug 7, 2018
Provisional Application 62697920 · Jul 13, 2018
Provisional Application 62697923 · Jul 13, 2018
Provisional Application 62697926 · Jul 13, 2018
Provisional Application 62639608 · Mar 7, 2018
Related Publication 20200255389A1 · Aug 13, 2020