Patent US10610805

Methods to separate cannabidiol and tetrahydrocannabinol
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US10610805

1. A method to separate cannabidiol and tetrahydrocannabinol, comprising: (8) (41)

the starting composition comprises an alcohol phase;

the alcohol phase is a liquid;

the alcohol phase comprises (a) at least 90 percent of the ethanol of the starting composition, (b) at least 50 percent of the cannabidiol of the starting composition, and (c) at least some of the tetrahydrocannabinol of the starting composition;

the ethanol of the alcohol phase is a solvent;

the cannabidiol of the alcohol phase is a solute that is dissolved in the ethanol of the alcohol phase;

the tetrahydrocannabinol of the alcohol phase is a solute that is dissolved in the ethanol of the alcohol phase;

the ethanol of the alcohol phase is present in the alcohol phase at a concentration of at least 35 percent and no greater than 99 percent by mass;

the starting composition comprises the cannabidiol at a concentration of at least 0.65 percent and no greater than 65 percent by mass;

the starting composition comprises the tetrahydrocannabinol at a concentration of at least 0.065 percent and no greater than 6.5 percent by mass;

the starting composition comprises the cannabidiol and the tetrahydrocannabinol at a cannabidiol-to-tetrahydrocannabinol ratio of at least 10:1 and less than 350:1 by mass;

the cannabidiol of the starting composition has a solubility in the alcohol phase that is greater than 10 grams per liter; and

the tetrahydrocannabinol of the starting composition has a solubility in the alcohol phase that is greater than 10 grams per liter;

the solubility-regulating composition comprises water;

the solubility-regulating composition comprises the water at a concentration by mass that is greater than the concentration by mass of any water that is present in the alcohol phase of the starting composition such that the combination of the alcohol phase and the solubility-regulating composition has a greater concentration of water than the alcohol phase of the starting composition;

the heterogeneous composition comprises each of (a) the ethanol of the starting composition, (b) the cannabidiol of the starting composition, (c) the tetrahydrocannabinol of the starting composition, and (d) the water of the solubility-regulating composition;

the heterogeneous composition comprises an aqueous phase and a tetrahydrocannabinol-enriched lipid phase;

the aqueous phase is a liquid;

the aqueous phase comprises greater than 50 percent of the cannabidiol of the heterogeneous composition;

the aqueous phase comprises greater than 50 percent of the ethanol of the heterogeneous composition;

the aqueous phase comprises at least 95 percent of the water of the heterogeneous composition;

either (a) the ethanol of the aqueous phase is a solvent, and the water of the aqueous phase is a solute that is dissolved in the ethanol of the aqueous phase, or (b) the water of the aqueous phase is a solvent, and the ethanol of the aqueous phase is a cosolvent;

the cannabidiol of the heterogeneous composition has a solubility in the aqueous phase that is greater than 10 grams per liter;

the cannabidiol of the aqueous phase is a solute that is dissolved in the solvent of the aqueous phase;

the tetrahydrocannabinol of the heterogeneous composition has a solubility in the aqueous phase that is less than 10 grams per liter;

the aqueous phase comprises the cannabidiol of the aqueous phase and any tetrahydrocannabinol that is dissolved in the solvent of the aqueous phase at a cannabidiol-to-tetrahydrocannabinol ratio that is greater than 350:1 by mass; and

the tetrahydrocannabinol-enriched lipid phase comprises greater than 50 percent of the tetrahydrocannabinol of the heterogeneous composition;

the fractionated heterogeneous composition comprises a fractionated aqueous phase and a fractionated tetrahydrocannabinol-enriched lipid phase;

the fractionated aqueous phase consists of either a fraction or all of the aqueous phase of the heterogeneous composition;

the fractionated aqueous phase comprises either a fraction or all of the cannabidiol of the aqueous phase;

the fractionated aqueous phase comprises either a fraction or all of the ethanol of the aqueous phase;

the fractionated aqueous phase comprises either a fraction or all of the water of the aqueous phase;

the fractionated tetrahydrocannabinol-enriched lipid phase consists of either a fraction or all of the tetrahydrocannabinol-enriched lipid phase of the heterogeneous composition; and

the fractionated tetrahydrocannabinol-enriched lipid phase comprises either a fraction or all of the tetrahydrocannabinol of the tetrahydrocannabinol-enriched lipid phase of the heterogeneous composition;

the second fractionated aqueous phase comprises either a fraction or all of the cannabidiol of the fractionated aqueous phase;

the second fractionated aqueous phase comprises either a fraction or all of the ethanol of the fractionated aqueous phase; and

the second fractionated aqueous phase comprises either a fraction or all of the water of the fractionated aqueous phase;

the product comprises cannabidiol;

the product lacks tetrahydrocannabinol at a concentration greater than 0.3 percent by mass;

the product comprises cannabidiol and any tetrahydrocannabinol at a cannabidiol-to-tetrahydrocannabinol ratio that is greater that 350:1 by mass;

the product lacks ethanol at a concentration greater than 5 percent by mass; and

the product lacks water at a concentration greater than 5 percent by mass.

2. The method of claim 1, in which: (0) (48)

the starting composition comprises ethanol at a concentration of 35 percent to 90 percent by mass;

the starting composition comprises cannabidiol at a concentration of 5 percent to 60 percent by mass;

the starting composition comprises tetrahydrocannabinol at a concentration of to 0.1 percent to 5 percent by mass;

the starting composition comprises cannabichromene at a concentration of 0.1 percent to 5 percent by mass;

the starting composition comprises cannabigerol at a concentration of 0.05 percent to 3 percent by mass;

the starting composition comprises beta-caryophyllene at a concentration of 0.1 percent to 5 percent by mass;

the alcohol phase comprises (a) at least some of the cannabichromene of the starting composition, (b) at least some of the cannabigerol of the starting composition, and (c) at least some of the beta-caryophyllene of the starting composition;

the cannabichromene of the alcohol phase is a solute that is dissolved in the ethanol of the alcohol phase;

the cannabigerol of the alcohol phase is a solute that is dissolved in the ethanol of the alcohol phase;

the beta-caryophyllene of the alcohol phase is a solute that is dissolved in the ethanol of the alcohol phase;

the heterogeneous composition comprises each of (a) the cannabichromene of the starting composition, (b) the cannabigerol of the starting composition, and (c) the beta-caryophyllene of the starting composition;

the cannabichromene of the starting composition has a solubility in the alcohol phase that is greater than 10 grams per liter;

the cannabichromene of the heterogeneous composition has a solubility in the aqueous phase that is less than 10 grams per liter;

the combining of the alcohol phase and the solubility-regulating composition drives a portion of the cannabichromene of the alcohol phase out of the alcohol phase;

the beta-caryophyllene of the starting composition has a solubility in the alcohol phase that is greater than 5 grams per liter;

the beta-caryophyllene of the heterogeneous composition has a solubility in the aqueous phase that is less than 5 grams per liter;

the combining of the alcohol phase and the solubility-regulating composition drives a portion of the beta-caryophyllene of the alcohol phase out of the alcohol phase;

the cannabigerol of the starting composition has a solubility in the alcohol phase that is greater than 10 grams per liter;

the cannabigerol of the heterogeneous composition has a solubility in the aqueous phase that is greater than 10 grams per liter;

the aqueous phase comprises greater than 65 percent of the cannabigerol of the heterogeneous composition;

the cannabigerol of the aqueous phase is a solute that is dissolved in the solvent of the aqueous phase;

the aqueous phase comprises greater than 65 percent of the cannabidiol of the heterogeneous composition;

the tetrahydrocannabinol-enriched lipid phase comprises greater than 65 percent of the tetrahydrocannabinol of the heterogeneous composition;

the tetrahydrocannabinol-enriched lipid phase comprises greater than 65 percent of the cannabichromene of the heterogeneous composition;

the tetrahydrocannabinol-enriched lipid phase comprises greater than 65 percent of the beta-caryophyllene of the heterogeneous composition;

the mechanical separation of the fractionated aqueous phase of the fractionated heterogeneous composition from the fractionated tetrahydrocannabinol-enriched lipid phase of the fractionated heterogeneous composition comprises centrifuging the fractionated heterogeneous composition;

the separation of (a) the majority of the ethanol of the second fractionated aqueous phase and the majority of the water of the second fractionated aqueous phase from (b) the majority of the cannabidiol of the second fractionated aqueous phase comprises combining the second fractionated aqueous phase and a second solubility-regulating composition to (i) drive a portion of the cannabidiol of the second fractionated aqueous phase out of the second fractionated aqueous phase, (ii) drive a portion of the cannabigerol of the second fractionated aqueous phase out of the second fractionated aqueous phase, and (iii) produce a second heterogeneous composition;

the second solubility-regulating composition comprises water at a concentration by mass that is greater than the concentration by mass of the water that is present in the second fractionated aqueous phase such that the combination of the second fractionated aqueous phase and the second solubility-regulating composition has a greater concentration of water than the second fractionated aqueous phase;

the second heterogeneous composition comprises (a) substantially all of the ethanol of the second fractionated aqueous phase, (b) substantially all of the cannabidiol of the second fractionated aqueous phase, (c) substantially all of the cannabigerol of the second fractionated aqueous phase, (d) substantially all of the water of the second fractionated aqueous phase, and (e) the water of the second solubility-regulating composition;

the second heterogeneous composition comprises a residual aqueous phase and a cannabidiol-enriched lipid phase;

the residual aqueous phase is a liquid;

the residual aqueous phase comprises greater than 50 percent of the ethanol of the second heterogeneous composition;

the residual aqueous phase comprises greater than 95 percent of the water of the second heterogeneous composition;

the cannabidiol of the second heterogeneous composition has a solubility in the residual aqueous phase that is less than 10 grams per liter;

the cannabidiol-enriched lipid phase comprises greater than 80 percent of the cannabidiol of the second heterogeneous composition;

the cannabigerol of the second heterogeneous composition has a solubility in the residual aqueous phase that is less than 10 grams per liter;

the cannabidiol-enriched lipid phase comprises greater than 80 percent of the cannabigerol of the second heterogeneous composition;

the cannabidiol-enriched lipid phase comprises the cannabidiol of the cannabidiol-enriched lipid phase and any tetrahydrocannabinol that is present in the cannabidiol-enriched lipid phase at a cannabidiol-to-tetrahydrocannabinol ratio that is greater than 350:1 by mass;

the mechanical separation of the residual aqueous phase of the second heterogeneous composition from the cannabidiol-enriched lipid phase of the second heterogeneous composition comprises centrifuging the second heterogeneous composition to produce (a) an aqueous liquid, which comprises the majority of the ethanol of the second fractionated aqueous phase and the majority of the water of the second fractionated aqueous phase, and (b) an oil and any precipitate, which comprises the majority of the cannabidiol of the second fractionated aqueous phase;

the product consists essentially of the oil and any precipitate;

the product comprises cannabidiol at a concentration of at least 75 percent by mass;

the product comprises cannabigerol at a concentration of at least 0.05 percent and no greater than 5 percent by mass;

the product lacks cannabichromene at a concentration greater than 5 percent by mass;

the product lacks beta-caryophyllene at a concentration greater than 5 percent by mass;

the product is obtained at a temperature of at least 20 degrees Celsius and no greater than 65 degrees Celsius;

the oil is a supercooled liquid; and

the temperature of the product is below the freezing point of the oil.

3. The method of claim 1, in which the starting composition comprises: (1) (3)

ethanol at a concentration of 35 percent to 90 percent by mass;

cannabidiol at a concentration of 5 percent to 60 percent by mass; and

tetrahydrocannabinol at a concentration of to 0.1 percent to 5 percent by mass.

4. The method of claim 3, in which: (4) (17)

the starting composition comprises cannabichromene, cannabigerol, and beta-caryophyllene;