# US 11,078,145 B2 · Process for separating a constituent/cannabinoid using a chromatographic resin > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,078,145 B2 - Document ID: US11078145B2 - Status: Granted - Kind: B2 - Application number: 17/011,780 - Filed: 2020-09-03 - Published: 2020-12-24 - Granted: 2021-08-03 - Earliest claimed: 2017-07-07 - Assignees: Orochem Technologies Inc. - Applicants: Orochem Technologies Inc. - Inventors: Anil Rajaram Oroskar; David W. House; Praneeth Dayanthe Edirisinghe; Asha Anil Oroskar; Faridedin Adel; Xinjie Chen; Gautham Anil Oroskar; Kunal Gulati - Web page: https://patentgrep.com/patent/US11078145B2 ## CPC - B01D 15/1821: {Simulated moving beds} - C07C 37/685: {Processes comprising at least two steps in series} - A61K 31/658: {o-phenolic cannabinoids, e.g. cannabidiol, cannabigerolic acid, cannabichromene or tetrahydrocannabinol} - B01D 9/0013: {by indirect heat exchange} - B01D 11/0288: {Applications, solvents} - B01D 15/185: {characterised by the components to be separated} - B01D 15/1871: {placed in series} - B01D 15/265: {Adsorption chromatography} - B01D 15/267: {using neutral sorbents, e.g. activated carbon or diatomaceous earth} - B01D 15/327: {with hydrophobic interaction} - C07C 37/82: by solid-liquid treatment; by chemisorption - C07C 37/84: by crystallisation - C07C 51/42: Separation; Purification; Stabilisation; Use of additives - C07C 51/47: by solid-liquid treatment; by chemisorption - C07D 311/80: Dibenzopyrans; Hydrogenated dibenzopyrans - B01D 15/325: {Reversed phase} - B01D 2257/70: Organic compounds not provided for in groups B01D2257/00 - B01D2257/602 - C07C 39/23: polycyclic, containing six-membered aromatic rings and other rings, with unsaturation outside the aromatic rings - C07C 65/19: having unsaturation outside the aromatic ring - C07C 2601/16: the ring being unsaturated - B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28) - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) ## Abstract A method for purification and separation of cannabinoids, such as cannabidiol and tetrahydrocannabinol, e.g., from dried hemp and cannabis leaves can use a continuous simulated moving bed process, a batch column chromatography method, or a single column, and a combination of one or more of a sequence of purification steps including: filtration, decolorization, activation or decarboxylation, dewaxing, polishing, and crystallization to separate a cannabinoid from the cannabis plant and to provide various cannabinoid products. The cannabinoid products can be used in various pharmaceutical and nutraceutical applications. ## Claims ### Claim 1 A method of separating a cannabinoid of a cannabis plant using simulated moving bed (SMB) chromatography, the cannabis plant including the cannabinoid and at least one impurity, the method comprising: preparing a feedstock stream from the cannabis plant, the feedstock stream including the cannabinoid, at least one impurity, and a solvent, and passing the feedstock stream through a chromatographic resin arranged in a simulated moving bed (SMB) chromatography configuration to provide a primary raffinate stream, wherein the primary raffinate stream has a higher purity of the cannabinoid than in the feedstock stream as measured by weight percentage of the solid content, and wherein the chromatographic resin comprises a hydrophobic polystyrene-divinylbenzene adsorbent. ### Claim 2 (depends on 1) The method of claim 1, wherein the cannabinoid is CBD, CBDA, or a mixture thereof. ### Claim 3 (depends on 1) The method of claim 1, wherein said at least one impurity comprises at least one of waxes, lipids, pigments, and mixtures thereof. ### Claim 4 (depends on 1) The method of claim 1, wherein said at least one impurity comprises a second cannabinoid selected from cannabigerol (CBG), cannabinol (CBN), tetrahydrocannabinol (THC), tetrahydrocannabinolic acid (THCA), and combinations thereof. ### Claim 5 (depends on 1) The method of claim 1, wherein the feedstock stream comprises a hemp extract, a decolorized hemp extract, a decolorized and decarboxylated hemp extract, or any combination thereof. ### Claim 6 (depends on 1) The method of claim 1, wherein the solvent of the feedstock stream comprises water, ethanol, acetone, ethyl acetate, acetonitrile, pentanes, hexanes, heptanes, methanol, propanol, or a combination thereof. ### Claim 7 (depends on 6) The method of claim 6, wherein the solvent of the feedstock stream comprises ethanol. ### Claim 8 (depends on 1) The method of claim 1, wherein the hydrophobic polystyrene-divinylbenzene adsorbent has: (i) an average particle diameter of from about 25 microns to about 600 microns, (ii) an average bulk density of from about 0.4 g/mL to about 0.9 g/mL, (iii) an average water content of from about 55% to about 65%, (iv) an average surface area of from about 450 m2/g to about 550 m2/g, (v) an average pore volume of from about 0.7 mL/g to about 0.9 mL/g, (vi) from about 4% to about 8% crosslinking, or (vii) any combination thereof. ### Claim 9 (depends on 8) The method of claim 8, wherein the cannabinoid is CBD, CBDA, or a mixture thereof. ### Claim 10 (depends on 8) The method of claim 8, wherein said at least one impurity comprises at least one of waxes, lipids, pigments, and mixtures thereof. ### Claim 11 (depends on 8) The method of claim 8, wherein said at least one impurity comprises a second cannabinoid selected from cannabigerol (CBG), cannabinol (CBN), tetrahydrocannabinol (THC), tetrahydrocannabinolic acid (THCA), and combinations thereof. ### Claim 12 (depends on 8) The method of claim 8, wherein the feedstock stream comprises a hemp extract, a decolorized hemp extract, a decolorized and decarboxylated hemp extract, or any combination thereof. ### Claim 13 (depends on 8) The method of claim 8, wherein the solvent of the feedstock stream comprises water, ethanol, acetone, ethyl acetate, acetonitrile, pentanes, hexanes, heptanes, methanol, propanol, or a combination thereof. ### Claim 14 (depends on 13) The method of claim 13, wherein the solvent of the feedstock stream comprises ethanol. ### Claim 15 (depends on 1) The method of claim 1, wherein the hydrophobic polystyrene-divinylbenzene adsorbent has an average particle diameter of from about 25 microns to about 300 microns. ### Claim 16 (depends on 1) The method of claim 1, wherein the hydrophobic polystyrene-divinylbenzene adsorbent has an average particle diameter of from about 250 microns to about 600 microns. ### Claim 17 (depends on 1) The method of claim 1, wherein the hydrophobic polystyrene-divinylbenzene adsorbent has an average bulk density of from about 0.4 g/mL to about 0.6 g/mL. ### Claim 18 (depends on 1) The method of claim 1, wherein the hydrophobic polystyrene-divinylbenzene adsorbent has an average bulk density of from about 0.6 g/mL to about 0.9 g/mL. ### Claim 19 (depends on 1) The method of claim 1, wherein the hydrophobic polystyrene-divinylbenzene adsorbent has an average water content of from about 55% to about 65%. ### Claim 20 (depends on 1) The method of claim 1, wherein the hydrophobic polystyrene-divinylbenzene adsorbent has an average surface area of from about 450 m2/g to about 550 m2/g. ### Claim 21 (depends on 1) The method of claim 1, wherein the hydrophobic polystyrene-divinylbenzene adsorbent has an average pore volume of from about 0.7 mL/g to about 0.9 mL/g. ### Claim 22 (depends on 1) The method of claim 1, wherein the hydrophobic polystyrene-divinylbenzene adsorbent has from about 4% to about 8% crosslinking. ### Claim 23 (depends on 1) The method of claim 1, wherein the primary raffinate has less than 1 wt. % of tetrahydrocannabinol (THC) and tetrahydrocannabinolic acid (THCA) based on the amount of the cannabinoid. ### Claim 24 (depends on 1) The method of claim 1, wherein the primary raffinate has less than 0.3 wt. % of tetrahydrocannabinol (THC) and tetrahydrocannabinolic acid (THCA) based on the amount of the cannabinoid. ### Claim 25 A method of separating at least one desired cannabinoid of a cannabis plant using simulated moving bed (SMB) chromatography, the cannabis plant including the at least one desired cannabinoid and at least one impurity cannabinoid, the method comprising: preparing a feedstock stream from the cannabis plant, the feedstock stream including the at least one desired cannabinoid, at least one impurity cannabinoid, and a solvent, and passing the feedstock stream through a chromatographic resin arranged in a simulated moving bed (SMB) chromatography configuration to provide a primary raffinate stream, wherein the primary raffinate stream has a reduced amount of the at least one impurity cannabinoid relative to the feedstock stream as measured by weight percentage of the solid content, and wherein the chromatographic resin comprises a hydrophobic polystyrene-divinylbenzene adsorbent. ### Claim 26 (depends on 25) The method of claim 25, wherein the at least one desired cannabinoid is CBD, CBDA, or a mixture thereof. ### Claim 27 (depends on 25) The method of claim 25, wherein the at least one impurity cannabinoid is tetrahydrocannabinol (THC), tetrahydrocannabinolic acid (THCA), or a mixture thereof. ### Claim 28 (depends on 25) The method of claim 25, wherein the feedstock stream comprises a hemp extract, a decolorized hemp extract, a decolorized and decarboxylated hemp extract, or any combination thereof. ### Claim 29 (depends on 25) The method of claim 25, wherein the solvent of the feedstock stream comprises water, ethanol, acetone, ethyl acetate, acetonitrile, pentanes, hexanes, heptanes, methanol, propanol, or a combination thereof. ### Claim 30 (depends on 29) The method of claim 29, wherein the solvent of the feedstock stream comprises ethanol. ### Claim 31 (depends on 25) The method of claim 25, wherein the hydrophobic polystyrene-divinylbenzene adsorbent has: (i) an average particle diameter of from about 25 microns to about 600 microns, (ii) an average bulk density of from about 0.4 g/mL to about 0.9 g/mL, (iii) an average water content of from about 55% to about 65%, (iv) an average surface area of from about 450 m2/g to about 550 m2/g, (v) an average pore volume of from about 0.7 mL/g to about 0.9 mL/g, (vi) from about 4% to about 8% crosslinking, or (vii) any combination thereof. ### Claim 32 (depends on 31) The method of claim 31, wherein the at least one desired cannabinoid is CBD, CBDA, or a mixture thereof. ### Claim 33 (depends on 31) The method of claim 31, wherein the at least one impurity cannabinoid is tetrahydrocannabinol (THC), tetrahydrocannabinolic acid (THCA), or a mixture thereof. ### Claim 34 (depends on 31) The method of claim 31, wherein the feedstock stream comprises a hemp extract, a decolorized hemp extract, a decolorized and decarboxylated hemp extract, or any combination thereof. ### Claim 35 (depends on 31) The method of claim 31, wherein the solvent of the feedstock stream comprises water, ethanol, acetone, ethyl acetate, acetonitrile, pentanes, hexanes, heptanes, methanol, propanol, or a combination thereof. ### Claim 36 (depends on 35) The method of claim 35, wherein the solvent of the feedstock stream comprises ethanol. ### Claim 37 (depends on 31) The method of claim 31, wherein the hydrophobic polystyrene-divinylbenzene adsorbent has an average particle diameter of from about 25 microns to about 300 microns. ### Claim 38 (depends on 31) The method of claim 31, wherein the hydrophobic polystyrene-divinylbenzene adsorbent has an average particle diameter of from about 250 microns to about 600 microns. ### Claim 39 (depends on 31) The method of claim 31, wherein the hydrophobic polystyrene-divinylbenzene adsorbent has an average bulk density of from about 0.4 g/mL to about 0.6 g/mL. ### Claim 40 (depends on 31) The method of claim 31, wherein the hydrophobic polystyrene-divinylbenzene adsorbent has an average bulk density of from about 0.6 g/mL to about 0.9 g/mL. ### Claim 41 (depends on 31) The method of claim 31, wherein the hydrophobic polystyrene-divinylbenzene adsorbent has an average water content of from about 55% to about 65%. ### Claim 42 (depends on 31) The method of claim 31, wherein the hydrophobic polystyrene-divinylbenzene adsorbent has an average surface area of from about 450 m2/g to about 550 m2/g. ### Claim 43 (depends on 31) The method of claim 31, wherein the hydrophobic polystyrene-divinylbenzene adsorbent has an average pore volume of from about 0.7 mL/g to about 0.9 mL/g. ### Claim 44 (depends on 31) The method of claim 31, wherein the hydrophobic polystyrene-divinylbenzene adsorbent has from about 4% to about 8% crosslinking. ### Claim 45 (depends on 31) The method of claim 31, wherein the primary raffinate has less than 1 wt. % of tetrahydrocannabinol (THC) and tetrahydrocannabinolic acid (THCA) as measured by weight percentage of the solid content. ### Claim 46 (depends on 31) The method of claim 31, wherein the primary raffinate has less than 0.3 wt. % of tetrahydrocannabinol (THC) and tetrahydrocannabinolic acid (THCA) as measured by weight percentage of the solid content.