Chiral separation of Δ8-THC, Δ9-THC, and related enantiomers using CO2-based chromatography

A method of separating an isomer of THC selected from (+)trans-Δ8-THC, (−)trans-Δ8-THC, (+)trans-Δ9-THC, and (−)trans-Δ9-THC using CO2-based chromatography, comprising

• injecting a sample comprising the isomer of THC into a CO2-based mobile phase;
• flowing the CO2-based mobile phase and sample into a CO2-based chromatography system having a 150 mm length and 3 mm internal diameter column including a stationary phase disposed within the column, the stationary phase comprising modified polysaccharide-coated silica-based particles with a particle size of 2.5 μm at a rate of 2 mL/min;
• and
• eluting the isomer of THC from the chromatography column using a mobile phase comprising CO2 and ethanol, wherein the retention time of the isomer of THC, or the first isomer of THC when multiple isomers are present, is greater than 1.5 minutes, and the total elution period of the isomer of THC, or the total elution period for the last eluted isomer of THC when multiple isomers are present, is 6 minutes or less, wherein a resolution of each pair of isomers is greater than about 2.