Method of continuously producing cannabinol from cannabis plant and uses thereof

Patent metadata

Field	Value
Publication number	US-11717474-B2
Application number	US-202017138312-A
Country	US
Kind code	B2
Filing date	Dec 30, 2020
Priority date	Dec 31, 2019
Publication date	Aug 8, 2023
Grant date	Aug 8, 2023

Abstract

Provided are: a method of preparing a cannabis processed product having an increased CBN content in an efficient and economic manner, through cyclization of CBD and aromatization of THC by continuous microwave irradiation of a cannabis extract; and use of a processed product having an increased CBN content prepared by the method, a fraction thereof, and a single ingredient of CBN, in foods, drugs, and cosmetics.

First claim

What is claimed is:

1. A method of producing cannabinoids, the method comprising irradiating microwaves to a reaction mixture comprising a Cannabis sp. plant or an extract thereof, an acid, and a solvent in a reaction vessel,
wherein the microwave irradiation is carried out while flowing the reaction mixture from an inlet of the reaction vessel and out through an outlet of the reaction vessel,
wherein the Cannabis sp. plant or the extract thereof comprises one or more of CBD and THC, and the cannabinoid is one or more of THC and CBN,
wherein the reaction vessel is connected to a temperature control chamber for controlling the temperature inside the reaction vessel,
wherein the reaction vessel is contained in the temperature control chamber filled with a liquid to control a temperature of the reaction mixture,
wherein the temperature control chamber comprises a microwave-transparent material, and
wherein the acid is methanesulfonic acid (MSA), benzenesulfonic acid, naphthalenesulfonic acid, toluenesulfonic acid, para-toluenesulfonic acid (p-toluensulfonic acid, PTSA), camphor-10-sulfonic acid (CSA), or a mixture thereof.

2. The method of claim 1 , further comprising isolating cannabinoids from the microwave-irradiated reaction mixture.

3. The method of claim 1 , wherein the extract is obtained by a method comprising contacting the Cannabis sp. plant with one or more of water, a protonic solvent, an aprotonic solvent, and a mixture thereof.

4. The method of claim 1 , wherein the Cannabis sp. plant comprises leaves, flower buds, seeds, nuts, trichomes, flower bracts, stems, or any part comprising cannabinoids.

5. The method of claim 1 , wherein the content of one or more of CBD and THC in the extract is 1% by weight or more, based on the total weight of the extract.

6. The method of claim 1 , wherein the microwave irradiation is carried out at 60° C. to 150° C.

7. The method of claim 1 , wherein the microwave irradiation is carried out for a time sufficient to convert one or more of CBD and THC into one or more of THC and CBN.

8. The method of claim 1 , wherein the microwave irradiation is carried out for about 5 minutes to about 180 minutes in a continuous reactor.

9. The method of claim 1 , wherein the microwave irradiation is carried out under pressure.

10. The method of claim 1 , wherein the microwave irradiation is carried out at a pressure of 2 atm to 100 atm.

11. The method of claim 1 , wherein the microwave irradiation is carried out at a frequency of 300 MHz to 300 GHz.

12. The method of claim 1 , wherein the microwave irradiation is carried out at a power of 3 W to 6 kW.

13. The method of claim 1 , wherein, in the microwave irradiation, the solvent is water, C1-C12 alcohol, or an aqueous solution thereof.

14. The method of claim 1 , wherein the solvent is ethanol, isopropanol, butanol, or a 50% to 99% ethanol aqueous solution.

15. The method of claim 2 , wherein the isolated cannabinoids comprise 5% by weight to 100% by weight of CBN, based on the total weight of the isolate.

16. The method of claim 1 , wherein the reaction vessel comprises a tube between the inlet of the vessel and the outlet of the vessel.

17. The method of claim 1 , wherein the reaction vessel is made of a microwave-transparent material.

Assignees

• Korea Inst Sci & Tech

Inventors

• Ham Jungyeob
• Kim Taejung
• Chung Bong Chul
• Ha Sungdo
• Lee Seok
• Kim Jin-Chul
• Choi Pilju
• Song Bong Geun

Classifications

• A61K8/498 Primary

  having 6-membered rings or their condensed derivatives, e.g. coumarin · CPC title

• A23L5/34

  using microwaves · CPC title

• A23L33/105

  Plant extracts, their artificial duplicates or their derivatives · CPC title

• C07D311/80 Primary

  Dibenzopyrans; Hydrogenated dibenzopyrans · CPC title

• A23V2002/00

  Food compositions, function of food ingredients or processes for food or foodstuffs · CPC title