PROCESS FOR REMOVING THC FROM CANNABINOIDS
A method of removing THC and THCA from a non-decarboxylated hemp extract, the non-decarboxylated hemp extract including THC and THCA and at least one cannabinoid is provided. The method comprises passing a first feedstock stream through a first chromatographic resin arranged in a simulated moving bed (SMB) chromatography configuration to provide a primary raffinate stream, preparing a second feedstock stream, the second feedstock stream comprising the primary raffinate stream or a concentrated primary raffinate stream, and passing the second feedstock stream through a second chromatographic resin to provide an eluate stream, the eluate stream having less than 0.1 wt % THC on a solvent free basis. The cannabinoid products can be used in various pharmaceutical and nutraceutical applications.
1 . A method of removing THC and THCA from a non-decarboxylated hemp extract, the non-decarboxylated hemp extract including THC and THCA and at least one cannabinoid, the method comprising:
preparing a first feedstock stream from the non-decarboxylated hemp extract, the first feedstock stream comprising THC and THCA, at least one cannabinoid, and a first solvent;
passing the first feedstock stream through a first chromatographic resin arranged in a simulated moving bed (SMB) chromatography configuration to provide a primary raffinate stream and an SMB extract stream, the primary raffinate stream having less than 0.5 wt % THC on a solvent free basis and optionally a higher weight percentage of at least one cannabinoid than in the first feedstock stream on a solvent free basis;
optionally removing at least a portion of the first solvent from the primary raffinate stream to produce a concentrated primary raffinate stream;
preparing a second feedstock stream, the second feedstock stream comprising the primary raffinate stream or the concentrated primary raffinate stream and a second solvent and the second feedstock stream having less than 0.5 wt % THC on a solvent free basis; and
passing the second feedstock stream through a second chromatographic resin to provide an eluate stream, the eluate stream having less than 0.1 wt % THC on a solvent free basis and optionally a higher weight percentage of at least one cannabinoid than in the second feedstock stream on a solvent free basis.
2 . The method of claim 1 , wherein the at least one cannabinoid is cannabidiol (CBD), cannabidiolic acid (CBDA), or a mixture thereof.
3 . The method of claim 1 , wherein the non-decarboxylated hemp extract is decolorized.
4 . The method of claim 1 , wherein the primary raffinate stream and the second feedstock stream each have less than 0.4 wt % THC on a solvent free basis.
5 . The method of claim 1 , wherein the primary raffinate stream and the second feedstock stream each have less than 0.3 wt % THC on a solvent free basis.
6 . The method of claim 1 , wherein the first chromatographic resin and the second chromatographic resin are each independently selected from:
(i) an activated carbon adsorbent,
(ii) a silica adsorbent,
(iii) a hydrophobic divinylbenzene-based adsorbent,
(iv) an activated alumina adsorbent,
(v) a reverse phase carbon-based adsorbent, and
(vi) a combination thereof.
7 . The method of claim 1 , wherein the first chromatographic resin is a hydrophobic divinylbenzene-based adsorbent.
8 . The method of claim 7 , wherein the hydrophobic divinylbenzene-based adsorbent has:
(i) an average particle diameter of 20 microns to 600 microns,
(ii) an average surface area of 450 m 2 /g to 900 m 2 /g,
(iii) an average pore size of 75 Å to 550 Å,
(iv) an average water content of 35% to 80%,
(v) an average bulk density of 0.45 g/mL to 0.9 g/mL, or
(vi) any combination thereof.
9 . The method of claim 7 , wherein the hydrophobic divinylbenzene-based adsorbent is a polystyrene-divinylbenzene adsorbent.
10 . The method of claim 1 , wherein the second chromatographic resin is an activated carbon adsorbent.
11 . The method of claim 10 , wherein the activated carbon adsorbent has:
(i) an average particle diameter of 40 microns to 1700 microns,
(ii) an iodine number of 900 mg/g or more, or
(iii) a combination thereof.
12 . The method of claim 1 , wherein the second chromatographic resin is disposed in a single column or more than one column in series.
13 . The method of claim 1 , wherein the second chromatographic resin is arranged in a simulated moving bed (SMB) chromatography configuration.
14 . The method of claim 1 , the eluate stream having less than 0.05 wt % THC on a solvent free basis.
15 . The method of claim 1 , the eluate stream having less than 0.01 wt % THC on a solvent free basis.
16 . A method of removing THC and THCA from a non-decarboxylated hemp extract, the non-decarboxylated hemp extract including THC and THCA and at least one cannabinoid, the method comprising:
preparing a first feedstock stream from the non-decarboxylated hemp extract, the first feedstock stream comprising THC and THCA, at least one cannabinoid, and a first solvent;
passing the first feedstock stream through a first chromatographic resin arranged in a simulated moving bed (SMB) chromatography configuration to provide a primary raffinate stream and an SMB extract stream, wherein passing the first feedstock stream through the first chromatographic resin arranged in a simulated moving bed (SMB) chromatography configuration removes greater than 75 wt % of the THC from the non-decarboxylated hemp extract as measured by the mass of THC in the primary raffinate compared to the mass of THC in the non-decarboxylated hemp extract;
optionally removing at least a portion of the first solvent from the primary raffinate stream to produce a concentrated primary raffinate stream;
preparing a second feedstock stream, the second feedstock stream comprising the primary raffinate stream or the concentrated primary raffinate stream and a second solvent; and
passing the second feedstock stream through a second chromatographic resin to provide an eluate stream, wherein passing the second feedstock stream through the second chromatographic resin removes up to 25 wt % of the THC from the non-decarboxylated hemp extract as measured by the mass of THC in the eluate stream compared to the mass of THC in the non-decarboxylated hemp extract.
17 . The method of claim 16 , wherein the at least one cannabinoid is cannabidiol (CBD), cannabidiolic acid (CBDA), or a mixture thereof.
18 . The method of claim 16 , wherein the non-decarboxylated hemp extract is decolorized.
19 . The method of claim 16 , wherein passing the first feedstock stream through the first chromatographic resin arranged in a simulated moving bed (SMB) chromatography configuration removes greater than 80 wt % of the THC from the non-decarboxylated hemp extract as measured by the mass of THC in the primary raffinate compared to the mass of THC in the non-decarboxylated hemp extract, and wherein passing the second feedstock stream through the second chromatographic resin removes up to 20 wt % of the THC from the non-decarboxylated hemp extract as measured by the mass of THC in the eluate stream compared to the mass of THC in the non-decarboxylated hemp extract.
20 . The method of claim 16 , wherein passing the first feedstock stream through the first chromatographic resin arranged in a simulated moving bed (SMB) chromatography configuration removes greater than 90 wt % of the THC from the non-decarboxylated hemp extract as measured by the mass of THC in the primary raffinate compared to the mass of THC in the non-decarboxylated hemp extract, and wherein passing the second feedstock stream through the second chromatographic resin removes up to 10 wt % of the THC from the non-decarboxylated hemp extract as measured by the mass of THC in the eluate stream compared to the mass of THC in the non-decarboxylated hemp extract.
21 . The method of claim 16 , wherein the first chromatographic resin and the second chromatographic resin are each independently selected from:
(i) an activated carbon adsorbent,
(ii) a silica adsorbent,
(iii) a hydrophobic divinylbenzene-based adsorbent,
(iv) an activated alumina adsorbent,
(v) a reverse phase carbon-based adsorbent, and
(vi) a combination thereof.
22 . The method of claim 16 , wherein the first chromatographic resin is a hydrophobic divinylbenzene-based adsorbent.
23 . The method of claim 22 , wherein the hydrophobic divinylbenzene-based adsorbent has:
(i) an average particle diameter of 20 microns to 600 microns,
(ii) an average surface area of 450 m 2 /g to 900 m 2 /g,
(iii) an average pore size of 75 Å to 550 Å,
(iv) an average water content of 35% to 80%,
(v) an average bulk density of 0.45 g/mL to 0.9 g/mL, or
(vi) any combination thereof.
24 . The method of claim 22 , wherein the hydrophobic divinylbenzene-based adsorbent is a polystyrene-divinylbenzene adsorbent.
25 . The method of claim 16 , wherein the second chromatographic resin is an activated carbon adsorbent.
26 . The method of claim 25 , wherein the activated carbon adsorbent has:
(i) an average particle diameter of 40 microns to 1700 microns,
(ii) an iodine number of 900 mg/g or more, or
(iii) a combination thereof.
27 . The method of claim 16 , wherein the second chromatographic resin is disposed in a single column or more than one column in series.
28 . The method of claim 16 , wherein the second chromatographic resin is arranged in a simulated moving bed (SMB) chromatography configuration.
29 . The method of claim 16 , the eluate stream having less than 0.1 wt % THC on a solvent free basis.
30 . The method of claim 16 , the eluate stream having less than 0.05 wt % THC on a solvent free basis.