Disclosed are methods for separating, recovering, and purifying tetrahydrocannabinolic acid (THCA) salts from an organic solvent solution comprising a mixture of cannabinoids. The methods comprise solubilizing the mixture of cannabinoids in a selected C5-C7 hydrocarbon solvent, adding thereto a selected amine to thereby precipitate a THCA-amine salt therefrom, dissolving the recovered THCA-amine salt in a selected solvent and then adding thereto a selected antisolvent to thereby recrystallize a purified THCA-amine salt therefrom. The recrystallized THCA-amine salt may be decarboxylated to form a mixture of Δ9-tetrahydrocannabinol (Δ9-THC) and amine. The Δ9-THC amine mixture may be acidified to separate the amine from Δ9-THC. The recovered Δ9-THC may be concentrated to produce a highly purified Δ9-THC. Also disclosed are THCA-amine salts produced with amines selected from groups of diamines, amino alcohols, and tertiary amines.

Disclosed are methods for separating, recovering, and purifying tetrahydrocannabinolic acid (THCA) salts from an organic solvent solution comprising a mixture of cannabinoids. The methods comprise solubilizing the mixture of cannabinoids in a selected C5-C7 hydrocarbon solvent, adding thereto a selected amine to thereby precipitate a THCA-amine salt therefrom, dissolving the recovered THCA-amine salt in a selected solvent and then adding thereto a selected antisolvent to thereby recrystallize a purified THCA-amine salt therefrom. The recrystallized THCA-amine salt may be decarboxylated to form a mixture of Δ9-tetrahydrocannabinol (Δ9-THC) and amine. The Δ9-THC amine mixture may be acidified to separate the amine from Δ9-THC. The recovered Δ9-THC may be concentrated to produce a highly purified Δ9-THC. Also disclosed are THCA-amine salts produced with amines selected from groups of diamines, amino alcohols, and tertiary amines.

Δ.sup.9-Tetrahydrocannabinol (Δ.sup.9-THC or THC) and cannabidiol (CBD) are major constituents of the Cannabis plant that have pharmacological properties with potential therapeutic value. This invention is directed to processes for large scale isolation of these two and other cannabinoids from the Cannabis sativa plant. This is accomplished through the discovery that protected amino acid esters of the cannabinoids are easier to separate using normal phase silica column chromatography. Mild base hydrolysis of the esters regenerates the free cannabinoids in a purified form. The invention is also applicable to the isolation of other cannabinoids from Cannabis extracts.

Δ.sup.9-Tetrahydrocannabinol (Δ.sup.9-THC or THC) and cannabidiol (CBD) are major constituents of the Cannabis plant that have pharmacological properties with potential therapeutic value. This invention is directed to processes for large scale isolation of these two and other cannabinoids from the Cannabis sativa plant. This is accomplished through the discovery that protected amino acid esters of the cannabinoids are easier to separate using normal phase silica column chromatography. Mild base hydrolysis of the esters regenerates the free cannabinoids in a purified form. The invention is also applicable to the isolation of other cannabinoids from Cannabis extracts.

Δ.sup.9-Tetrahydrocannabinol (Δ.sup.9-THC or THC) and cannabidiol (CBD) are major constituents of the Cannabis plant that have pharmacological properties with potential therapeutic value. This invention is directed to processes for large scale isolation of these two and other cannabinoids from the Cannabis sativa plant. This is accomplished through the discovery that protected amino acid esters of the cannabinoids are easier to separate using normal phase silica column chromatography. Mild base hydrolysis of the esters regenerates the free cannabinoids in a purified form. The invention is also applicable to the isolation of other cannabinoids from Cannabis extracts.

The present invention relates to a method for purifying phenol, which comprises: contacting a phenol stream comprising hydroxyacetone, 2-methylbenzofuran, 3-methylbenzofuran and phenol with an acyl chloride in the presence of an organic sulfonic acid to convert one or more selected from the group consisting of hydroxyacetone, 2-methylbenzofuran and 3-methylbenzofuran into a high boiling point compound having a boiling point higher than that of the phenol; and recovering the high boiling point compound from the phenol stream.

The present invention relates to a method for purifying phenol, which comprises: contacting a phenol stream comprising hydroxyacetone, 2-methylbenzofuran, 3-methylbenzofuran and phenol with an acyl chloride in the presence of an organic sulfonic acid to convert one or more selected from the group consisting of hydroxyacetone, 2-methylbenzofuran and 3-methylbenzofuran into a high boiling point compound having a boiling point higher than that of the phenol; and recovering the high boiling point compound from the phenol stream.

The present invention relates to a method for purifying phenol, which comprises: contacting a phenol stream comprising hydroxyacetone, 2-methylbenzofuran, 3-methylbenzofuran and phenol with an acyl chloride in the presence of an organic sulfonic acid to convert one or more selected from the group consisting of hydroxyacetone, 2-methylbenzofuran and 3-methylbenzofuran into a high boiling point compound having a boiling point higher than that of the phenol; and recovering the high boiling point compound from the phenol stream.

A method for decomposing a phenolic by-product generated in a phenol preparation process, the method including: adding a phenolic by-product stream, a decomposition apparatus side discharge stream, and process water to a mixing apparatus and mixing the phenolic by-product stream, the decomposition apparatus side discharge stream, and the process water; adding a mixing apparatus discharge stream discharged from the mixing apparatus to a phase separation apparatus and phase-separating the mixing apparatus discharge stream into an oil phase and an aqueous phase; feeding an oil phase stream discharged from the phase-separation apparatus and discharged to a decomposition apparatus and decomposing the oil phase stream; and circulating the decomposition apparatus side discharge stream discharged from the decomposition apparatus to the mixing apparatus.

A method for decomposing a phenolic by-product generated in a phenol preparation process, the method including: adding a phenolic by-product stream, a decomposition apparatus side discharge stream, and process water to a mixing apparatus and mixing the phenolic by-product stream, the decomposition apparatus side discharge stream, and the process water; adding a mixing apparatus discharge stream discharged from the mixing apparatus to a phase separation apparatus and phase-separating the mixing apparatus discharge stream into an oil phase and an aqueous phase; feeding an oil phase stream discharged from the phase-separation apparatus and discharged to a decomposition apparatus and decomposing the oil phase stream; and circulating the decomposition apparatus side discharge stream discharged from the decomposition apparatus to the mixing apparatus.