The present invention provides improved solvents, methods, and systems for isolating purified cannabinoids from various sources. It has been found that C.sub.9 to C.sub.11 non-aromatic hydrocarbon solvents, and especially n-decane, work surprisingly well for crystallization of cannabinoids such as cannabidiol. Some variations provide a method of isolating cannabinoids from a cannabinoid-containing solution, comprising contacting the solution with a C.sub.9-C.sub.11 non-aromatic hydrocarbon solvent (e.g., n-decane) at a first temperature, to generate a mixture; cooling the mixture to precipitate cannabinoids; and isolating the precipitated cannabinoids. Other variations provide a method of isolating cannabinoids from a cannabinoid-containing solution, comprising contacting the solution with a C.sub.9-C.sub.11 non-aromatic hydrocarbon solvent (e.g., n-decane) at a first temperature below the solvent boiling point, to generate a mixture; subjecting the mixture to a second temperature that causes vaporization of the solvent, to precipitate at least some of the cannabinoids; and isolating the precipitated cannabinoids.

This invention is for improving the manufacturing pharmaceutical grade CBD and other cannabinoids following current Good Manufacturing Practices (cGMP) of the US FDA for use in clinical trials for CNS and other indications by the NIH and other researchers. The major cannabinoids in marijuana (Cannabis) and hemp originate from Cannabigerolic Acid (CBGA) present in the biomass of the plant. Plant enzymes that are specific to different strains of biomass converts CBGA to different carboxylic acids of cannabinoids including Cannabidiolic Acid (CBDA) and Δ9-Tetrahydrocannabinolic Acid (Δ9-THCA). These are relatively stable in the growing and fresh-cut plants. These are converted by thermal decarboxylation to Cannabidiol (CBD) and Δ9-Tetrahydrocannabinol (Δ9-THC), carbon dioxide and water. Cannabinoids can be manufactured by first heating the Cannabis biomass to convert carboxylic acids prior to extraction and purification. Alternatively, and preferably because of manufacturing cost and product stability, the carboxylic acids can be first extracted and purified. They can be utilized in the carboxylic acid form or stored in a stable manner until converted to cannabinoids for use in medicine. This invention provides an efficient method for their conversion utilizing a high-pressure reactor under inert conditions.

This invention is for improving the manufacturing pharmaceutical grade CBD and other cannabinoids following current Good Manufacturing Practices (cGMP) of the US FDA for use in clinical trials for CNS and other indications by the NIH and other researchers. The major cannabinoids in marijuana (Cannabis) and hemp originate from Cannabigerolic Acid (CBGA) present in the biomass of the plant. Plant enzymes that are specific to different strains of biomass converts CBGA to different carboxylic acids of cannabinoids including Cannabidiolic Acid (CBDA) and Δ9-Tetrahydrocannabinolic Acid (Δ9-THCA). These are relatively stable in the growing and fresh-cut plants. These are converted by thermal decarboxylation to Cannabidiol (CBD) and Δ9-Tetrahydrocannabinol (Δ9-THC), carbon dioxide and water. Cannabinoids can be manufactured by first heating the Cannabis biomass to convert carboxylic acids prior to extraction and purification. Alternatively, and preferably because of manufacturing cost and product stability, the carboxylic acids can be first extracted and purified. They can be utilized in the carboxylic acid form or stored in a stable manner until converted to cannabinoids for use in medicine. This invention provides an efficient method for their conversion utilizing a high-pressure reactor under inert conditions.

The present disclosure relates to isolating one or more cannabinoids from an input mixture. There is disclosed an apparatus that comprises a mixing vessel, a volatizing unit, and a distillation unit. The mixing vessel combines a first input mixture and a high boiling-point carrier agent to generate a second input mixture. The volatizing unit volatilizes cannabinoids from the second input mixture for separating the mixture into a cannabinoid-containing vapor stream and a residue. The distillation unit receives the cannabinoid-containing vapor stream and separates a first cannabinoid from at least a second cannabinoid. There are also disclosed methods that comprise the steps of combining a first input mixture with a high boiling-point carrier agent to provide a second input mixture, volatilizing the second input mixture into a vapor stream containing one or more cannabinoids and a residue, and separating a first cannabinoid from a second in the distillation unit.

The present disclosure relates to isolating one or more cannabinoids from an input mixture. There is disclosed an apparatus that comprises a mixing vessel, a volatizing unit, and a distillation unit. The mixing vessel combines a first input mixture and a high boiling-point carrier agent to generate a second input mixture. The volatizing unit volatilizes cannabinoids from the second input mixture for separating the mixture into a cannabinoid-containing vapor stream and a residue. The distillation unit receives the cannabinoid-containing vapor stream and separates a first cannabinoid from at least a second cannabinoid. There are also disclosed methods that comprise the steps of combining a first input mixture with a high boiling-point carrier agent to provide a second input mixture, volatilizing the second input mixture into a vapor stream containing one or more cannabinoids and a residue, and separating a first cannabinoid from a second in the distillation unit.

The present invention describes a method which outlines a process for conversion of CBD to a Δ.sup.9-tetrahydrocannabinol (Δ.sup.9-THC) compound or derivative thereof involving treating a naturally produced CBD intermediate compound with an organoaluminum-based Lewis acid catalyst, under conditions effective to produce the Δ.sup.9-tetrahydrocannabinol compound or derivative thereof at a relatively high concentration. The source of the CBD is from industrial hemp having less than 0.3% Δ.sup.9-THC and extracting and purifying a CBD distillate or isolate or a combination thereof. This procedure will produce Δ.sup.9-THC that is essentially free from any other cannabinoids other than some trace amounts of the initial CBD starting material, or about 95% Δ.sup.9-THC and 2-4% CBD. Another aspect of the present invention relates to a process for further purification and enrichment of the Δ.sup.9-THC using distillation and collecting an essentially pure fraction of Δ.sup.9-THC using additional distillation or enrichment form of purification. Included are methods and processes to scale the reaction from the lab to large scale manufacturing. Included are methods for adding a molecule marker to authenticate high purity Δ.sup.9-THC products. Formulations and uses for pharmaceuticals, nutraceuticals, food products, and topicals are also provided.

The present invention describes a method which outlines a process for conversion of CBD to a Δ.sup.9-tetrahydrocannabinol (Δ.sup.9-THC) compound or derivative thereof involving treating a naturally produced CBD intermediate compound with an organoaluminum-based Lewis acid catalyst, under conditions effective to produce the Δ.sup.9-tetrahydrocannabinol compound or derivative thereof at a relatively high concentration. The source of the CBD is from industrial hemp having less than 0.3% Δ.sup.9-THC and extracting and purifying a CBD distillate or isolate or a combination thereof. This procedure will produce Δ.sup.9-THC that is essentially free from any other cannabinoids other than some trace amounts of the initial CBD starting material, or about 95% Δ.sup.9-THC and 2-4% CBD. Another aspect of the present invention relates to a process for further purification and enrichment of the Δ.sup.9-THC using distillation and collecting an essentially pure fraction of Δ.sup.9-THC using additional distillation or enrichment form of purification. Included are methods and processes to scale the reaction from the lab to large scale manufacturing. Included are methods for adding a molecule marker to authenticate high purity Δ.sup.9-THC products. Formulations and uses for pharmaceuticals, nutraceuticals, food products, and topicals are also provided.

A fluid catalytic cracking process for p-cresol dimer to produce valuable phenolic monomers, i.e., 2-methyl phenol, 4-methyl phenol, 2,3-xylenol, and phenol, uses an equilibrium catalyst (E-cat) generated in the petroleum fluid catalytic cracking (FCC) unit. The p-cresol dimer can be processed under relatively mild conditions, while maximizing desired and minimizing undesired products. The process may include charging an equilibrium fluid catalytic cracking catalyst; heating to a predetermined cracking temperature and pressure; (c) charging a p-cresol dimer feed; (d) contacting the p-cresol dimer with the equilibrium fluid catalytic cracking catalyst; (e) condensing resulting phenolic monomer vapors to obtain phenolic monomer liquid and fluidization gas; (f) separating the phenolic monomer liquid from the fluidization gas; (g) collecting the separated phenolic monomer liquid; (h) separating the collected phenolic monomer liquid individual phenolic monomers; and (i) recycling any unconverted p-cresol dimer into the fluidized bed reactor.

A fluid catalytic cracking process for p-cresol dimer to produce valuable phenolic monomers, i.e., 2-methyl phenol, 4-methyl phenol, 2,3-xylenol, and phenol, uses an equilibrium catalyst (E-cat) generated in the petroleum fluid catalytic cracking (FCC) unit. The p-cresol dimer can be processed under relatively mild conditions, while maximizing desired and minimizing undesired products. The process may include charging an equilibrium fluid catalytic cracking catalyst; heating to a predetermined cracking temperature and pressure; (c) charging a p-cresol dimer feed; (d) contacting the p-cresol dimer with the equilibrium fluid catalytic cracking catalyst; (e) condensing resulting phenolic monomer vapors to obtain phenolic monomer liquid and fluidization gas; (f) separating the phenolic monomer liquid from the fluidization gas; (g) collecting the separated phenolic monomer liquid; (h) separating the collected phenolic monomer liquid individual phenolic monomers; and (i) recycling any unconverted p-cresol dimer into the fluidized bed reactor.

The present disclosure relates to the preparation of halogenated dihydroxybenzene compounds with high yield, selectivity and purity. The compounds are useful, among other things, in the synthesis of cannabinoids and cannabinoid-type compounds.