Methods to chemically modify cannabinoids
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.
1. A method to chemically modify a cannabinoid molecule, comprising:
providing a composition comprising cannabinoids, wherein the composition comprises an extracted oil that was extracted from a plant material of the genus Cannabis , the extracted oil comprises the cannabinoids, the cannabinoids comprise a native cannabinoid molecule, and the native cannabinoid molecule comprises a carboxyl group;
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 from the heated surface 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,
wherein:
the method comprises converting less than 2 percent of the native cannabinoid molecule into cannabinol by mole;
the method is performed such that the liquid distillate comprises the condensed cannabinoid molecule and cannabinol at a molar ratio of greater than 100:1; and
the method is performed such that the liquid distillate comprises cannabinol at a concentration of less than 0.8 percent by weight.
2. A method to chemically modify a cannabinoid molecule, comprising:
providing a composition comprising cannabinoids, wherein the composition comprises an extracted oil that was extracted from a plant material of the genus Cannabis , the extracted oil comprises the cannabinoids, the cannabinoids comprise a native cannabinoid molecule, and the native cannabinoid molecule comprises a carboxyl group;
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 from the heated surface 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,
wherein the method is performed such that:
the liquid distillate comprises the condensed cannabinoid molecule and cannabinol at a molar ratio of greater than 100:1; and
the liquid distillate comprises the condensed cannabinoid molecule and delta-8-tetrahydrocannabinol at a molar ratio of greater than 300:1.
3. The method of claim 2 , wherein:
the native cannabinoid molecule is cannabidiolic acid;
the modified cannabinoid molecule is cannabidiol; and
the condensed cannabinoid molecule is cannabidiol.
4. The method of claim 2 , wherein:
the native cannabinoid molecule is tetrahydrocannabinolic acid;
the modified cannabinoid molecule is tetrahydrocannabinol; and
the condensed cannabinoid molecule is tetrahydrocannabinol.
5. The method of claim 4 , comprising producing a product comprising tetrahydrocannabinol at a concentration of at least 55 percent by weight from the liquid distillate.
6. The method of claim 4 , wherein the sufficient energy is at least 0.0004 kilowatt hours and no greater than 0.04 kilowatt hours of energy per gram of the composition.
7. The method of claim 4 , wherein the sufficient energy is at least 0.0004 kilowatt hours and no greater than 0.004 kilowatt hours of energy per gram of the composition.
8. A method to chemically modify a cannabinoid molecule, comprising:
providing a composition comprising cannabinoids, wherein the composition comprises an extracted oil that was extracted from a plant material of the genus Cannabis , the extracted oil comprises the cannabinoids, the cannabinoids comprise a native cannabinoid molecule, and the native cannabinoid molecule comprises a carboxyl group;
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 from the heated surface to convert the native cannabinoid molecule into (i) a carbon dioxide molecule and (ii) a modified cannabinoid molecule in a gas phase, wherein the gas phase comprises less than 5 percent by volume molecular oxygen;
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, wherein the composition comprises an extracted oil that was extracted from a plant material of the genus Cannabis , the extracted oil comprises the cannabinoids, the cannabinoids comprise a native cannabinoid molecule, and the native cannabinoid molecule comprises a carboxyl group;
coating a heated surface with the composition at a surface-area-to-volume ratio of the composition that is greater than 500 per meter, wherein the heated surface is a surface of a thin-film evaporator;
contacting the composition with sufficient energy from the heated surface 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.
10. A method to chemically modify a cannabinoid molecule, comprising:
providing a composition comprising cannabinoids, wherein the composition comprises an extracted oil that was extracted from a plant material of the genus Cannabis , the extracted oil comprises the cannabinoids, the cannabinoids comprise a native cannabinoid molecule, and the native cannabinoid molecule comprises a carboxyl group;
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 from the heated surface to convert the native cannabinoid molecule into (i) a carbon dioxide molecule and (ii) a modified cannabinoid molecule in a gas phase wherein the sufficient energy is at least 0.0004 kilowatt hours and no greater than 0.004 kilowatt hours of energy per gram of the composition;
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.
11. The method of claim 8 , wherein:
the native cannabinoid molecule is tetrahydrocannabinolic acid;
the modified cannabinoid molecule is tetrahydrocannabinol;
the condensed cannabinoid molecule is tetrahydrocannabinol; and
the sufficient energy is less than 0.004 kilowatt hours of energy per gram of the composition.
12. The method of claim 8 , wherein:
the native cannabinoid molecule is tetrahydrocannabinolic acid;
the modified cannabinoid molecule is tetrahydrocannabinol;
the condensed cannabinoid molecule is tetrahydrocannabinol; and
the sufficient energy is at least 0.0004 kilowatt hours and no greater than 0.004 kilowatt hours of energy per gram of the composition.
13. The method of claim 8 , wherein:
the native cannabinoid molecule is tetrahydrocannabinolic acid;
the modified cannabinoid molecule is tetrahydrocannabinol;
the condensed cannabinoid molecule is tetrahydrocannabinol; and
the method is performed such that the liquid distillate comprises the condensed cannabinoid molecule and cannabinol at a molar ratio of greater than 100:1.
14. The method of claim 8 , wherein:
the native cannabinoid molecule is tetrahydrocannabinolic acid;
the modified cannabinoid molecule is tetrahydrocannabinol;
the condensed cannabinoid molecule is tetrahydrocannabinol;
the method is performed such that the liquid distillate comprises the condensed cannabinoid molecule and cannabinol at a molar ratio of greater than 100:1; and
the sufficient energy is less than 0.004 kilowatt hours of energy per gram of the composition.
15. The method of claim 8 , wherein:
the native cannabinoid molecule is tetrahydrocannabinolic acid;
the modified cannabinoid molecule is tetrahydrocannabinol;
the condensed cannabinoid molecule is tetrahydrocannabinol; and
the method is performed such that the liquid distillate comprises the condensed cannabinoid molecule and delta-8-tetrahydrocannabinol at a molar ratio of greater than 300:1.
16. The method of claim 8 , wherein:
the native cannabinoid molecule is tetrahydrocannabinolic acid;
the modified cannabinoid molecule is tetrahydrocannabinol;
the condensed cannabinoid molecule is tetrahydrocannabinol;
the method is performed such that the liquid distillate comprises the condensed cannabinoid molecule and delta-8-tetrahydrocannabinol at a molar ratio of greater than 300:1; and
the sufficient energy is less than 0.004 kilowatt hours of energy per gram of the composition.
17. The method of claim 9 , wherein:
the native cannabinoid molecule is tetrahydrocannabinolic acid;
the modified cannabinoid molecule is tetrahydrocannabinol;
the condensed cannabinoid molecule is tetrahydrocannabinol; and
the sufficient energy is less than 0.004 kilowatt hours of energy per gram of the composition.
18. The method of claim 9 , wherein:
the native cannabinoid molecule is tetrahydrocannabinolic acid;
the modified cannabinoid molecule is tetrahydrocannabinol;
the condensed cannabinoid molecule is tetrahydrocannabinol; and
the sufficient energy is at least 0.0004 kilowatt hours and no greater than 0.004 kilowatt hours of energy per gram of the composition.
19. The method of claim 9 , wherein:
the native cannabinoid molecule is tetrahydrocannabinolic acid;
the modified cannabinoid molecule is tetrahydrocannabinol;
the condensed cannabinoid molecule is tetrahydrocannabinol; and
the method is performed such that the liquid distillate comprises the condensed cannabinoid molecule and cannabinol at a molar ratio of greater than 100:1.
20. The method of claim 9 , wherein:
the native cannabinoid molecule is tetrahydrocannabinolic acid;
the modified cannabinoid molecule is tetrahydrocannabinol;
the condensed cannabinoid molecule is tetrahydrocannabinol;
the method is performed such that the liquid distillate comprises the condensed cannabinoid molecule and cannabinol at a molar ratio of greater than 100:1; and
the sufficient energy is less than 0.004 kilowatt hours of energy per gram of the composition.
21. The method of claim 9 , wherein:
the native cannabinoid molecule is tetrahydrocannabinolic acid;
the modified cannabinoid molecule is tetrahydrocannabinol;
the condensed cannabinoid molecule is tetrahydrocannabinol; and
the method is performed such that the liquid distillate comprises the condensed cannabinoid molecule and delta-8-tetrahydrocannabinol at a molar ratio of greater than 300:1.
22. The method of claim 9 , wherein:
the native cannabinoid molecule is tetrahydrocannabinolic acid;
the modified cannabinoid molecule is tetrahydrocannabinol;
the condensed cannabinoid molecule is tetrahydrocannabinol;
the method is performed such that the liquid distillate comprises the condensed cannabinoid molecule and delta-8-tetrahydrocannabinol at a molar ratio of greater than 300:1; and
the sufficient energy is less than 0.004 kilowatt hours of energy per gram of the composition.
23. A method to chemically modify a cannabinoid molecule, comprising:
providing a composition comprising cannabinoids, wherein the composition comprises an extracted oil that was extracted from a plant material of the genus Cannabis , the extracted oil comprises the cannabinoids, the cannabinoids comprise a tetrahydrocannabinolic acid molecule, and the tetrahydrocannabinolic acid molecule comprises a carboxyl group;
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 from the heated surface to convert the tetrahydrocannabinolic acid molecule into (i) a carbon dioxide molecule and (ii) a tetrahydrocannabinol molecule in a gas phase, wherein the gas phase comprises less than 5 percent by volume molecular oxygen;
contacting the tetrahydrocannabinol molecule with a heat sink to condense the tetrahydrocannabinol molecule into a condensed tetrahydrocannabinol molecule in a liquid distillate that comprises the condensed tetrahydrocannabinol molecule and cannabinol at a molar ratio of greater than 100:1;
collecting the liquid distillate; and
producing a product comprising tetrahydrocannabinol at a concentration of at least 55 percent by weight from the liquid distillate.
24. A method to chemically modify a cannabinoid molecule, comprising:
providing a composition comprising cannabinoids, wherein the composition comprises an extracted oil that was extracted from a plant material of the genus Cannabis , the extracted oil comprises the cannabinoids, the cannabinoids comprise a tetrahydrocannabinolic acid molecule, and the tetrahydrocannabinolic acid molecule comprises a carboxyl group;
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 from the heated surface to convert the tetrahydrocannabinolic acid molecule into (i) a carbon dioxide molecule and (ii) a tetrahydrocannabinol molecule in a gas phase, wherein the sufficient energy is less than 0.004 kilowatt hours of energy per gram of the composition, and the gas phase comprises less than 5 percent by volume molecular oxygen;
contacting the tetrahydrocannabinol molecule with a heat sink to condense the tetrahydrocannabinol molecule into a condensed tetrahydrocannabinol molecule in a liquid distillate that comprises the condensed tetrahydrocannabinol molecule and cannabinol at a molar ratio of greater than 100:1;
collecting the liquid distillate; and
producing a product comprising tetrahydrocannabinol at a concentration of at least 55 percent by weight from the liquid distillate.
25. A method to chemically modify a cannabinoid molecule, comprising:
providing a composition comprising cannabinoids, wherein the composition comprises an extracted oil that was extracted from a plant material of the genus Cannabis , the extracted oil comprises the cannabinoids, the cannabinoids comprise a tetrahydrocannabinolic acid molecule, and the tetrahydrocannabinolic acid molecule comprises a carboxyl group;
coating a heated surface with the composition at a surface-area-to-volume ratio of the composition that is greater than 500 per meter, wherein the heated surface is a surface of a thin-film evaporator;
contacting the composition with sufficient energy from the heated surface to convert the tetrahydrocannabinolic acid molecule into (i) a carbon dioxide molecule and (ii) a tetrahydrocannabinol molecule in a gas phase;
contacting the tetrahydrocannabinol molecule with a heat sink to condense the tetrahydrocannabinol molecule into a condensed tetrahydrocannabinol molecule in a liquid distillate that comprises the condensed tetrahydrocannabinol molecule and cannabinol at a molar ratio of greater than 100:1;
collecting the liquid distillate; and
producing a product comprising tetrahydrocannabinol at a concentration of at least 55 percent by weight from the liquid distillate.
26. A method to chemically modify a cannabinoid molecule, comprising:
providing a composition comprising cannabinoids, wherein the composition comprises an extracted oil that was extracted from a plant material of the genus Cannabis , the extracted oil comprises the cannabinoids, the cannabinoids comprise a tetrahydrocannabinolic acid molecule, and the tetrahydrocannabinolic acid molecule comprises a carboxyl group;
coating a heated surface with the composition at a surface-area-to-volume ratio of the composition that is greater than 500 per meter, wherein the heated surface is a surface of a thin-film evaporator;
contacting the composition with sufficient energy from the heated surface to convert the tetrahydrocannabinolic acid molecule into (i) a carbon dioxide molecule and (ii) a tetrahydrocannabinol molecule in a gas phase, wherein the sufficient energy is less than 0.004 kilowatt hours of energy per gram of the composition;
contacting the tetrahydrocannabinol molecule with a heat sink to condense the tetrahydrocannabinol molecule into a condensed tetrahydrocannabinol molecule in a liquid distillate that comprises the condensed tetrahydrocannabinol molecule and cannabinol at a molar ratio of greater than 100:1;
collecting the liquid distillate; and
producing a product comprising tetrahydrocannabinol at a concentration of at least 55 percent by weight from the liquid distillate.