Methods to chemically modify cannabinoids

Patent metadata

Field	Value
Publication number	US-10669248-B2
Application number	US-201916271782-A
Country	US
Kind code	B2
Filing date	Feb 9, 2019
Priority date	Aug 10, 2018
Publication date	Jun 2, 2020
Grant date	Jun 2, 2020

Abstract

Various aspects of this disclosure relate to methods to lower the activation energy of the cannabinoid decarboxylation reaction by performing the decarboxylation reaction in the gas phase.

First claim

What is claimed is:

1. A method to chemically modify a cannabinoid molecule, comprising:
providing a composition comprising cannabinoids, in which the cannabinoids comprise a native cannabinoid molecule, the native cannabinoid molecule comprises a carboxyl group, and the native cannabinoid molecule is in a liquid phase or a solid phase;
contacting the composition with sufficient energy to convert the native cannabinoid molecule into (i) a carbon dioxide molecule and (ii) a modified cannabinoid molecule in a gas phase;
contacting the modified cannabinoid molecule with a heat sink to condense the modified cannabinoid molecule into a condensed cannabinoid molecule in a liquid distillate, in which at least 95% of the native cannabinoid molecule is converted into the condensed cannabinoid molecule per mole; and
collecting the liquid distillate.

2. A method to chemically modify a cannabinoid molecule, comprising:
providing a composition comprising cannabinoids, in which the cannabinoids comprise a native cannabinoid molecule, the native cannabinoid molecule comprises a carboxyl group, and the native cannabinoid molecule is in a liquid phase or a solid phase;
contacting the composition with sufficient energy to convert the native cannabinoid molecule into (i) a carbon dioxide molecule and (ii) a modified cannabinoid molecule in a gas phase;
contacting the modified cannabinoid molecule with a heat sink to condense the modified cannabinoid molecule into a condensed cannabinoid molecule in a liquid distillate; and
collecting the liquid distillate, in which the liquid distillate comprises the condensed cannabinoid molecule and cannabinol at a molar ratio greater than 100:1.

3. A method to chemically modify a cannabinoid molecule, comprising:
providing a composition comprising cannabinoids, in which the cannabinoids comprise a native cannabinoid molecule, the native cannabinoid molecule comprises a carboxyl group, and the native cannabinoid molecule is in a liquid phase or a solid phase;
contacting the composition with sufficient energy to convert the native cannabinoid molecule into (i) a carbon dioxide molecule and (ii) a modified cannabinoid molecule in a gas phase;
contacting the modified cannabinoid molecule with a heat sink to condense the modified cannabinoid molecule into a condensed cannabinoid molecule in a liquid distillate;
collecting the liquid distillate, in which the liquid distillate comprises ethanol; and
evaporating the ethanol to produce a product from the liquid distillate, in which the product comprises the condensed cannabinoid molecule at a concentration of at least 55% by weight.

4. A method to chemically modify a cannabinoid molecule, comprising:
providing a composition comprising cannabinoids, in which the cannabinoids comprise a native cannabinoid molecule, the native cannabinoid molecule comprises a carboxyl group, and the native cannabinoid molecule is in a liquid phase or a solid phase;
contacting the composition with 2 kilojoules to 50 kilojoules of energy per gram of the composition thereby converting the native cannabinoid molecule into (i) a carbon dioxide molecule and (ii) a modified cannabinoid molecule in a gas phase;
contacting the modified cannabinoid molecule with a heat sink to condense the modified cannabinoid molecule into a condensed cannabinoid molecule in a liquid distillate; and
collecting the liquid distillate.

5. A method to chemically modify a cannabinoid molecule, comprising:
providing a composition comprising cannabinoids, in which the cannabinoids comprise a native cannabinoid molecule, the native cannabinoid molecule comprises a carboxyl group, and the native cannabinoid molecule is in a liquid phase or a solid phase;
contacting the composition with sufficient energy to convert the native cannabinoid molecule into (i) a carbon dioxide molecule and (ii) a modified cannabinoid molecule in a gas phase;
contacting the modified cannabinoid molecule with a heat sink to condense the modified cannabinoid molecule into a condensed cannabinoid molecule in a liquid distillate; and
collecting the liquid distillate,
in which contacting the composition with sufficient energy to convert the native cannabinoid molecule into (i) the carbon dioxide molecule and (ii) the modified cannabinoid molecule in the gas phase comprises contacting the composition with energy at a rate of less than 100 kilowatts of power per gram of the composition for a duration of less than 60 seconds.

6. A method to chemically modify a cannabinoid molecule, comprising:
providing a composition comprising cannabinoids and cellulose, in which the cannabinoids comprise a native cannabinoid molecule, the native cannabinoid molecule comprises a carboxyl group, and the native cannabinoid molecule is in a liquid phase or a solid phase;
contacting the composition with sufficient energy to convert the native cannabinoid molecule into (i) a carbon dioxide molecule and (ii) a modified cannabinoid molecule in a gas phase;
separating the modified cannabinoid molecule in the gas phase from the cellulose;
collecting the cellulose;
contacting the modified cannabinoid molecule with a heat sink to condense the modified cannabinoid molecule into a condensed cannabinoid molecule in a liquid distillate; and
collecting the liquid distillate.

7. A method to chemically modify a cannabinoid molecule, comprising:
providing a composition comprising cannabinoids, in which the cannabinoids comprise a native cannabinoid molecule, the native cannabinoid molecule comprises a carboxyl group, and the native cannabinoid molecule is in a liquid phase or a solid phase;
suspending a particle or a droplet of the composition comprising cannabinoids in a gas phase, in which the particle or droplet comprises the native cannabinoid molecule;
contacting the composition with sufficient energy to convert the native cannabinoid molecule into (i) a carbon dioxide molecule and (ii) a modified cannabinoid molecule in a gas phase;
contacting the modified cannabinoid molecule with a heat sink to condense the modified cannabinoid molecule into a condensed cannabinoid molecule in a liquid distillate; and
collecting the liquid distillate.

8. A method to chemically modify a cannabinoid molecule, comprising:
providing a composition comprising cannabinoids, in which the cannabinoids comprise a native cannabinoid molecule, the native cannabinoid molecule comprises a carboxyl group, and the native cannabinoid molecule is in a liquid phase or a solid phase;
coating a heated surface with the composition at a surface-area-to-volume ratio of the composition that is greater than 500 per meter;
contacting the composition with sufficient energy to convert the native cannabinoid molecule into (i) a carbon dioxide molecule and (ii) a modified cannabinoid molecule in a gas phase;
contacting the modified cannabinoid molecule with a heat sink to condense the modified cannabinoid molecule into a condensed cannabinoid molecule in a liquid distillate; and
collecting the liquid distillate.

9. A method to chemically modify a cannabinoid molecule, comprising:
providing a composition comprising cannabinoids, in which the cannabinoids comprise a native cannabinoid molecule, the native cannabinoid molecule comprises a carboxyl group, and the native cannabinoid molecule is in a liquid phase or a solid phase;
contacting the composition with sufficient energy to convert the native cannabinoid molecule into (i) a carbon dioxide molecule and (ii) a modified cannabinoid molecule in a gas phase;
directing the composition along a heated path having a length of at least 4 meters, in which the composition is contacted with the sufficient energy in the heated path;
contacting the m

Assignees

• Natural Extraction Sys Llc

Inventors

• Thomas C Russell
• Depalo Matthew M

Classifications

• C07D311/78 Primary

  Ring systems having three or more relevant rings · CPC title

• C07C29/80

  by distillation · CPC title

• C07C67/08

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title

• B01D5/006

  with evaporation or distillation · CPC title

• C07D311/80

  Dibenzopyrans; Hydrogenated dibenzopyrans · CPC title