Methods to produce cannabinoid products from decarboxylated cannabinoid extracts

A method to produce cannabinoid crystals from a decarboxylated cannabinoid extract, comprising:

• (i) combining (a) a starting composition comprising a decarboxylated cannabinoid extract and (b) a solubility-regulating composition to produce a heterogeneous composition, in which:
• the starting composition comprises ethanol, a cannabinoid molecule, and a second molecule;
• the cannabinoid molecule is cannabidiol, cannabidivarin, cannabigerol, or cannabigerovarin;
• the second molecule is tetrahydrocannabinol, tetrahydrocannabivarin, or beta caryophyllene;
• the ethanol is a solvent of the starting composition;
• the cannabinoid molecule is a solute that is dissolved in the ethanol of the starting composition;
• the second molecule is a solute that is dissolved in the ethanol of the starting composition;
• the solubility-regulating composition comprises water;
• the heterogeneous composition comprises an aqueous phase and a lipid phase;
• the aqueous phase of the heterogeneous composition comprises at least 95 percent of the water of the heterogeneous composition;
• the aqueous phase of the heterogeneous composition comprises at least 95 percent of the ethanol of the heterogeneous composition;
• the second molecule has a solubility in the aqueous phase that is less than 10 grams per liter;
• the lipid phase comprises greater than 65 percent of the second molecule of the heterogeneous composition;
• the cannabinoid molecule has a solubility in the aqueous phase that is greater than 10 grams per liter;
• and
• the aqueous phase comprises greater than 65 percent of the cannabinoid molecule of the heterogeneous composition;
• (ii) separating the aqueous phase and the lipid phase to separate the cannabinoid molecule and the second molecule;
• and
• (iii) separating the cannabinoid molecule from both (a) at least 95 percent of the water of the aqueous phase and (b) at least 95 percent of the ethanol of the aqueous phase to produce a product, in which:
• the product consists essentially of the molecules of the aqueous phase that are separated from (a) the at least 95 percent of the water of the aqueous phase and (b) the at least 95 percent of the ethanol of the aqueous phase;
• the product lacks the second molecule at a concentration greater than 0.3 percent by mass;
• the product comprises crystals;
• the crystals comprise greater than 50 percent of the cannabinoid molecule of the product;
• the crystals comprise the cannabinoid molecule at a concentration greater than 50 percent by mass;
• the crystals have a melting point;
• and
• the crystals lack a glass-transition temperature.

A method to produce a supercooled cannabinoid oil from a decarboxylated cannabinoid extract, comprising:

• (i) combining (a) a starting composition comprising a decarboxylated cannabinoid extract and (b) a solubility-regulating composition to produce a heterogeneous composition, in which:
• the starting composition comprises ethanol, a cannabinoid molecule, and a second molecule;
• the cannabinoid molecule is cannabidiol, cannabidivarin, cannabigerol, or cannabigerovarin;
• the second molecule is tetrahydrocannabinol, tetrahydrocannabivarin, or beta caryophyllene;
• the ethanol is a solvent of the starting composition;
• the cannabinoid molecule is a solute that is dissolved in the ethanol of the starting composition;
• the second molecule is a solute that is dissolved in the ethanol of the starting composition;
• the solubility-regulating composition comprises water;
• the heterogeneous composition comprises an aqueous phase and a lipid phase;
• the aqueous phase of the heterogeneous composition comprises at least 95 percent of the water of the heterogeneous composition;
• the aqueous phase of the heterogeneous composition comprises at least 95 percent of the ethanol of the heterogeneous composition;
• the second molecule has a solubility in the aqueous phase that is less than 10 grams per liter;
• the lipid phase comprises greater than 65 percent of the second molecule of the heterogeneous composition;
• the cannabinoid molecule has a solubility in the aqueous phase that is greater than 10 grams per liter;
• and
• the aqueous phase comprises greater than 65 percent of the cannabinoid molecule of the heterogeneous composition;
• (ii) separating the aqueous phase and the lipid phase to separate the cannabinoid molecule and the second molecule;
• and
• (iii) separating the cannabinoid molecule from both (a) at least 95 percent of the water of the aqueous phase and (b) at least 95 percent of the ethanol of the aqueous phase to produce a product, in which:
• the product consists essentially of the molecules of the aqueous phase that are separated from (a) the at least 95 percent of the water of the aqueous phase and (b) the at least 95 percent of the ethanol of the aqueous phase;
• the product lacks the second molecule at a concentration greater than 0.3 percent by mass;
• the product comprises an oil;
• the oil comprises greater than 50 percent of the cannabinoid molecule of the product;
• the oil comprises the cannabinoid molecule at a concentration greater than 50 percent by mass;
• the oil is a supercooled liquid;
• the oil has a freezing point;
• and
• the oil lacks a glass-transition temperature.

A method to separate cannabidiol and tetrahydrocannabinol, comprising:

• (i) providing a starting composition comprising ethanol, cannabidiol, and tetrahydrocannabinol, in which:
• 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 by mass;
• the starting composition comprises the cannabidiol and the tetrahydrocannabinol at a cannabidiol-to-tetrahydrocannabinol ratio of 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;
• (ii) decreasing the solubility of the tetrahydrocannabinol in the alcohol phase of the starting composition by combining the alcohol phase and a solubility-regulating composition to (a) drive a portion of the tetrahydrocannabinol of the alcohol phase out of the alcohol phase and (b) produce a heterogeneous composition, in which:
• 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;
• (iii) selecting either a fraction or all of the heterogeneous composition for further processing to produce a fractionated heterogeneous composition, in which:
• 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;
• (iv) mechanically separating the fractionated aqueous phase of the fractionated heterogeneous composition from the fractionated tetrahydrocannabinol-enriched lipid phase of the fractionated heterogeneous composition to mechanically separate the cannabidiol of the fractionated aqueous phase from the tetrahydrocannabinol of the fractionated tetrahydrocannabinol-enriched lipid phase;
• (v) selecting either a fraction or all of the fractionated aqueous phase for further processing to produce a second fractionated aqueous phase, in which:
• 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;
• (vi) separating (a) a majority of the ethanol of the second fractionated aqueous phase and a majority of the water of the second fractionated aqueous phase from (b) a majority of the cannabidiol of the second fractionated aqueous phase to produce a product, in which:
• 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.