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

The disclosure provides a process for preparing solid tri(C.sub.1-C.sub.4 alkyl)ammonium dihydrogen phosphates such as triethylammonium dihydrogen phosphate, in high yield, and in a free-flowing particulate form. The solid product advantageously possesses less than about 1500 ppm of aprotic organic solvents, less than about 1500 ppm of C.sub.1-C.sub.5 alkanols, and less than about 500 ppm of water, as determined by Karl Fischer titration.

The disclosure provides a process for preparing solid tri(C.sub.1-C.sub.4 alkyl)ammonium dihydrogen phosphates such as triethylammonium dihydrogen phosphate, in high yield, and in a free-flowing particulate form. The solid product advantageously possesses less than about 1500 ppm of aprotic organic solvents, less than about 1500 ppm of C.sub.1-C.sub.5 alkanols, and less than about 500 ppm of water, as determined by Karl Fischer titration.

The present disclosure provides certain processes of making 3-fluoro-5-(((1S,2aR)-1,3,3,4,4-pentafluoro-2a-hydroxy-2,2a,3,4-tetrahydro-1H-cyclopenta[cd]inden-7-yl)oxy)-benzonitrile (Compound 1) and certain polymorphs thereof. Also provided are pharmaceutical compositions comprising a crystalline polymorph form of Compound 1 and processes for preparing such polymorph forms.

The present invention relates to highly concentrated, anhydrous amine salts of hydrocarbon polyalkoxy sulfates, wherein the salts are selected from the group of substituted amines, preferably alkanolamines. The products obtained are of low viscosity and pumpable at room temperature. Due to the absence of water, the salts are highly resistant to hydrolysis, even at high temperatures. The invention further relates to the use of the compositions according to the invention in an aqueous dilution for use in oil reservoirs with the aim of achieving enhanced oil production, or for the recovery of hydrocarbons from tar sands or other surfaces or materials provided with hydrocarbon.

The present invention relates to highly concentrated, anhydrous amine salts of hydrocarbon polyalkoxy sulfates, wherein the salts are selected from the group of substituted amines, preferably alkanolamines. The products obtained are of low viscosity and pumpable at room temperature. Due to the absence of water, the salts are highly resistant to hydrolysis, even at high temperatures. The invention further relates to the use of the compositions according to the invention in an aqueous dilution for use in oil reservoirs with the aim of achieving enhanced oil production, or for the recovery of hydrocarbons from tar sands or other surfaces or materials provided with hydrocarbon.

A process for the manufacture of ethyleneamines and ethanolamines, comprising the steps of (i) converting a glycolaldehyde derivative of formula (II), in which R.sup.2, R.sup.3 are—the same or different—hydrogen, alkyl, such as C.sub.1-6-alkyl, or cycloalkyl such as Cs-e-cycloalkyl; and an animating agent of formula (III); in which R1 is hydrogen (H), alkyl, such as C.sub.1-6-alkyl, or cycloalkyl such as C.sub.3-6-cycloalkyl, in the gas or liquid phase; (ii) feeding the reaction products obtained in step (i) into a hydrogenation reactor, where the reaction products are converted with hydrogen in the presence of a hydrogenation catalyst.

##STR00001##

A process for the manufacture of ethyleneamines and ethanolamines, comprising the steps of (i) converting a glycolaldehyde derivative of formula (II), in which R.sup.2, R.sup.3 are—the same or different—hydrogen, alkyl, such as C.sub.1-6-alkyl, or cycloalkyl such as Cs-e-cycloalkyl; and an animating agent of formula (III); in which R1 is hydrogen (H), alkyl, such as C.sub.1-6-alkyl, or cycloalkyl such as C.sub.3-6-cycloalkyl, in the gas or liquid phase; (ii) feeding the reaction products obtained in step (i) into a hydrogenation reactor, where the reaction products are converted with hydrogen in the presence of a hydrogenation catalyst.

##STR00001##

Described are compositions and methods for inhibiting polymerization of a monomer (e.g., styrene) composition a quinone methide polymerization retarder and an ammonium salt. In a mixture, the ammonium salt improves the efficacy of the quinone methide polymerization retarder and provides greater antipolymerant activity. In turn, the mixture reduces or prevents apparatus fouling and improves the purity of monomer streams.

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.