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US-12616728-B2 - Processes and systems for converting cannabinoids into cannabinoid derivatives and isolating the same

US12616728B2US 12616728 B2US12616728 B2US 12616728B2US-12616728-B2

Abstract

Some variations provide a process of converting a cannabinoid into a purified cannabinoid derivative, comprising: providing a starting composition comprising a cannabinoid; providing a C 9 -C 11 non-aromatic hydrocarbon solvent; introducing the starting composition and the solvent to a conversion reactor; chemically converting some, but not all, of the cannabinoid to a cannabinoid derivative, generating a reaction mixture containing unreacted cannabinoid; conveying the reaction mixture to a crystallization unit; cooling the reaction mixture to precipitate unreacted cannabinoid out of the reaction mixture, thereby generating a mother liquor containing the cannabinoid derivative; and isolating and recovering the cannabinoid derivative from the mother liquor. Systems configured to carry out the disclosed processes are also provided. This invention offers a large-scale solution to economically convert CBD to D9-THC, among many other example. The principles of the invention may be applied to the conversion of various cannabinoids and terpenes into derivative products.

Inventors

  • Armand J. Noel

Assignees

  • Armand J. Noel

Dates

Publication Date
20260505
Application Date
20231121

Claims (16)

  1. 1 . A method of preparing a cannabinoid derivative product, wherein the method comprises: (a) providing a starting composition comprising a cannabinoid; (b) providing a solvent comprising n-decane; (c) introducing said starting composition and said solvent to a conversion reactor; (d) operating said conversion reactor at effective reaction conditions to chemically convert said cannabinoid to a cannabinoid derivative at a cannabinoid conversion selected from about 10% to about 90%, thereby generating a reaction mixture containing unreacted cannabinoid; (e) conveying said reaction mixture to a crystallization unit; (f) within said crystallization unit, cooling said reaction mixture from a first temperature to a second temperature that is lower than said first temperature, to precipitate at least about 50% of said unreacted cannabinoid out of said reaction mixture, thereby generating a mother liquor containing said cannabinoid derivative; and (g) isolating and recovering said cannabinoid derivative from said mother liquor.
  2. 2 . The method of preparing the cannabinoid derivative product of claim 1 , wherein said cannabinoid is selected from the group consisting of cannabidiol, cannabidiolic acid, cannabigerol, cannabigerolic acid, cannabinol, cannabichromene, cannabichromenic acid, cannabicyclol, cannabivarin, cannabidivarin, cannabichromevarin, cannabigerovarin, cannabigerol monomethyl ether, cannabielsoin, cannabicitran, tetrahydrocannabinol, tetrahydrocannabinolic acid, tetrahydrocannabiorcol, tetrahydrocannabivarin, tetrahydrocannabiphorol, and combinations thereof.
  3. 3 . The method of preparing the cannabinoid derivative product of claim 1 , wherein said cannabinoid derivative is selected from the group consisting of CBD, CBDa, CBG, CBGa, D6-THC, D6-THCa, D8-THC, D8-THCa, D8-iso-THC, D9-THC, D9-THCa, D10-THC, D10-THCa, Exo-THC, Exo-THCa, CBN, CBNa, CBT (Tran), CBTa (Tran), CBT (Triol), CBTa (Triol), CBC, CBCa, CBL, CBLa, CBDV, CBDva, D6-THCV, D6-THCVa, D8-THCV, D8-THCVa, D9-THCV, D9-THCVa, D10-THCV, D10-THCVa, Exo-THCV, Exo-THCVa, CBGV, CBGVa, CBNV, CBNVa, CBTv (Tran), CBTva (Tran), CBTv (Triol), CBTva (Triol), CBCv, CBCva, CBLv, CBLva, CBDp, CBDpa, D6-THCp, D6-THCpa, D8-THCp, D8-THCpa, D9-THCp, D9-THCpa, D10-THCp, D10-THCpa, Exo-THCp, Exo-THCpa, CBGp, CBGpa, CBNp, CBNpa, CBTp (Tran), CBTpa (Tran), CBTp (Triol), CBTpa (Triol), CBCp, CBCpa, CBLp, CBLpa, CBDo, CBDoa, D6-THCo, D6-THCoa, D8-THCo, D8-THCoa, D9-THCo, D9-THCoa, D10-THCo, D10-THCoa, Exo-THCo, Exo-THCoa, CBGo, CBGoa, CBNo, CBNoa, CBTo (Tran), CBToa (Tran), CBTo (Triol), CBToa (Triol), CBCo, CBCoa, CBLo, CBLoa, CBDb, CBDba, D6-THCb, D6-THCba, D8-THCb, D8-THCba, D9-THCb, D9-THCba, D10-THCb, D10-THCba, Exo-THCb, Exo-THCba, CBGb, CBGba, CBNb, CBNba, CBTb (Tran), CBTba (Tran), CBTb (Triol), CBTba (Triol), CBCb, CBCba, CBLb, CBLba, hydrogenated variants thereof, acetylated variants thereof, and combinations of the foregoing.
  4. 4 . The method of preparing the cannabinoid derivative product of claim 1 , wherein said cannabinoid derivative is a mixture of at least two compounds selected from the group consisting of CBD, CBDa, CBG, CBGa, D6-THC, D6-THCa, D8-THC, D8-THCa, D8-iso-THC, D9-THC, D9-THCa, D10-THC, D10-THCa, Exo-THC, Exo-THCa, CBN, CBNa, CBT (Tran), CBTa (Tran), CBT (Triol), CBTa (Triol), CBC, CBCa, CBL, CBLa, CBDV, CBDva, D6-THCV, D6-THCVa, D8-THCV, D8-THCVa, D9-THCV, D9-THCVa, D10-THCV, D10-THCVa, Exo-THCV, Exo-THCVa, CBGV, CBGVa, CBNV, CBNVa, CBTv (Tran), CBTva (Tran), CBTv (Triol), CBTva (Triol), CBCv, CBCva, CBLv, CBLva, CBDp, CBDpa, D6-THCp, D6-THCpa, D8-THCp, D8-THCpa, D9-THCp, D9-THCpa, D10-THCp, D10-THCpa, Exo-THCp, Exo-THCpa, CBGp, CBGpa, CBNp, CBNpa, CBTp (Tran), CBTpa (Tran), CBTp (Triol), CBTpa (Triol), CBCp, CBCpa, CBLp, CBLpa, CBDo, CBDoa, D6-THCo, D6-THCoa, D8-THCo, D8-THCoa, D9-THCo, D9-THCoa, D10-THCo, D10-THCoa, Exo-THCo, Exo-THCoa, CBGo, CBGoa, CBNo, CBNoa, CBTo (Tran), CBToa (Tran), CBTo (Triol), CBToa (Triol), CBCo, CBCoa, CBLo, CBLoa, CBDb, CBDba, D6-THCb, D6-THCba, D8-THCb, D8-THCba, D9-THCb, D9-THCba, D10-THCb, D10-THCba, Exo-THCb, Exo-THCba, CBGb, CBGba, CBNb, CBNba, CBTb (Tran), CBTba (Tran), CBTb (Triol), CBTba (Triol), CBCb, CBCba, CBLb, CBLba, hydrogenated variants thereof, and acetylated variants thereof.
  5. 5 . The method of preparing the cannabinoid derivative product of claim 1 , wherein said cannabinoid derivative product consists essentially of D9-THC, substantially free of side products or catalyst contamination.
  6. 6 . The method of preparing the cannabinoid derivative product of claim 1 , wherein said cannabinoid derivative product consists essentially of D9-THC and CBD, substantially free of side products or catalyst contamination.
  7. 7 . The method of preparing the cannabinoid derivative product of claim 1 , wherein said cannabinoid derivative is an isomer of said cannabinoid.
  8. 8 . The method of preparing the cannabinoid derivative product of claim 1 , wherein said effective reaction conditions include hydrogenation with hydrogen in the presence of a hydrogenation catalyst, and wherein said hydrogenation converts said cannabinoid derivative into a hydrogenated cannabinoid derivative.
  9. 9 . The method of preparing the cannabinoid derivative product of claim 8 , wherein said hydrogenated cannabinoid derivative is HHC.
  10. 10 . The method of preparing the cannabinoid derivative product of claim 9 , wherein said HHC is a racemic mixture of 9R-HHC and 9S-HHC.
  11. 11 . The method of preparing the cannabinoid derivative product of claim 1 , wherein said cannabinoid derivative product further comprises residual n-decane solvent.
  12. 12 . The method of preparing the cannabinoid derivative product of claim 1 , and further comprising precipitating out at least about 90% of said unreacted cannabinoid of said reaction mixture.
  13. 13 . The method of preparing the cannabinoid derivative product of claim 1 , and further comprising washing said unreacted cannabinoid that is precipitated in step (f) to remove residual cannabinoid derivative.
  14. 14 . The method of preparing the cannabinoid derivative product of claim 1 , wherein said cannabinoid derivative product is in solid form.
  15. 15 . The method of preparing the cannabinoid derivative product of claim 1 , wherein said cannabinoid derivative product is in liquid form.
  16. 16 . The method of preparing the cannabinoid derivative product of claim of claim 1 , wherein said cannabinoid derivative product further contains an edible oil.

Description

PRIORITY DATA This U.S. continuation patent application claims priority to U.S. Provisional Patent App. No. 63/227,542, filed on Jul. 30, 2021, to U.S. Provisional Patent App. No. 63/227,875, filed on Jul. 30, 2021, and U.S. Nonprovisional patent application Ser. No. 17/813,716 filed Jul. 20, 2022 each of which is hereby incorporated by reference herein. FIELD OF THE INVENTION The present invention generally relates to processes and systems for converting cannabinoids into purified cannabinoid derivatives, and for converting terpenes into purified terpene derivatives. BACKGROUND OF THE INVENTION Compound isolation is an important process during the clean-up or production of certain compounds. Many chemical-engineering unit operations are configured for compound isolation. These processes include crystallization, distillation, chromatography, filtration, and many other. Crystallization is a proven technique to produce high-purity compound mixtures and for this reason crystallization is the foundation for many pharmaceutical processes. Crystallization is generally the process by which a solid forms, where the atoms or molecules are highly organized into a structure known as a crystal. Some of the ways by which crystals form are precipitating from a solution, freezing, or more rarely deposition directly from a gas. Compound crystallization via precipitation from solution is dependent on the solubility of the compound in a certain solvent over a broad temperature range. The goal is to choose a solvent for which the compound (the solute) is soluble at high temperatures, but insoluble or at least less soluble at lower temperatures. Initially, the compound is dissolved into the solvent at a high temperature. As the temperature of the solution decreases, the solute becomes oversaturated (higher than equilibrium concentration) and begins to precipitate out of the solution as a solid crystal. Biomass extracts have been used as a source of medicine throughout history and continue to serve as the basis for many pharmaceuticals, cosmeceuticals, and nutraceuticals today. Valuable biomass extracts include, but are by no means limited to, hemp, hops, chamomile, dandelion, Echinacea, marigold, lavender, and many other therapeutic plants and herbs. Cannabinoids are compounds found in the Cannabis plant. The Cannabis plant has been used for both medical and recreational purposes since prehistoric times, and is finding increasing scientific interest and acceptance for applications in modern medicine. Cannabis sativa and Cannabis indica are the species most often utilized. The Cannabis plant contains hundreds of individual compounds, including over 100 cannabinoids. Notable cannabinoids include tetrahydrocannabinol (THC) and cannabidiol (CBD) which are commonly extracted from the Cannabis plant on a commercial basis. THC is believed to be involved in a plant's evolutionary adaptation, putatively against insect predation, ultraviolet light, and environmental stress. The chemical formula for THC (C21H30O2) includes multiple isomers. A commercially desirable isomer is (−)-trans-Δ9-tetrahydrocannabinol, which is known as the delta-9-THC isomer, Δ9-THC, or D9-THC. D9-THC, as well as other cannabinoids that contain a phenol group, possess mild antioxidant activity sufficient to protect neurons against oxidative stress, such as that produced by glutamate-induced excitotoxicity. D9-THC is the principal psychoactive constituent of the Cannabis plant. D9-THC has been typically grown and extracted from marijuana. However, as consumer demand increases including for pharmaceutical uses, the production of D9-THC concentrates is proving much harder to scale than the high sales demand. D9-THC grown indoors has proven to be the highest-quality material on the market, but the cost to perform this operation has caused strain on the largest D9-THC producers in the world. In the effort to reduce cost, researchers have gone down the path of chemically converting hemp-derived CBD into D9-THC. The conversion of cannabinoids is known in the pharmaceutical industry. For example, dronabinol is a well-known pharmaceutical drug that utilizes the conversion of CBD into D9-THC. There is a need for a large-scale solution to convert CBD to D9-THC, in order to solve several problems today. First, conventional approaches of extracting D9-THC from marijuana are expensive and tedious to maintain due to crop failure. These factors make it incredibly expensive to create D9-THC in a safe and effective manner. Second, greenhouses are expensive to build and maintain. Typical greenhouses cost up to $20 million dollars and only have the capability to produce tens of kilograms of D9-THC a month or season. Traditional methods of converting D9-THC from CBD are plagued by the inability to efficiently produce a high-concentration distillate from pure conversion alone. On top of the concentration limitations, typical conversion problems still apply: racemic mixtures, side prod