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WO2025117755A1 - Procédé permettant d'isoler des terpènes à partir de trichomes - Google Patents

Procédé permettant d'isoler des terpènes à partir de trichomes Download PDF

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Publication number
WO2025117755A1
WO2025117755A1 PCT/US2024/057769 US2024057769W WO2025117755A1 WO 2025117755 A1 WO2025117755 A1 WO 2025117755A1 US 2024057769 W US2024057769 W US 2024057769W WO 2025117755 A1 WO2025117755 A1 WO 2025117755A1
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delta
trichomes
plant
aspects
acid
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Kenneth Michael MORROW
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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01H—NEW PLANTS OR NON-TRANSGENIC PROCESSES FOR OBTAINING THEM; PLANT REPRODUCTION BY TISSUE CULTURE TECHNIQUES
    • A01H6/00—Angiosperms, i.e. flowering plants, characterised by their botanic taxonomy
    • A01H6/28—Cannabaceae, e.g. cannabis
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/0211—Solvent extraction of solids in combination with an electric or magnetic field
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/0215—Solid material in other stationary receptacles
    • B01D11/0253—Fluidised bed of solid materials
    • B01D11/0257—Fluidised bed of solid materials using mixing mechanisms, e.g. stirrers, jets
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/0261—Solvent extraction of solids comprising vibrating mechanisms, e.g. mechanical, acoustical
    • B01D11/0265—Applying ultrasound
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/028—Flow sheets
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/0288—Applications, solvents
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/02—Recovery or refining of essential oils from raw materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B04—CENTRIFUGAL APPARATUS OR MACHINES FOR CARRYING-OUT PHYSICAL OR CHEMICAL PROCESSES
    • B04B—CENTRIFUGES
    • B04B5/00—Other centrifuges
    • B04B5/10—Centrifuges combined with other apparatus, e.g. electrostatic separators; Sets or systems of several centrifuges

Definitions

  • Cannabis and hops are two incredibly valuable plant commodities, though the plants themselves account for a small minority of consumer purchases.
  • Most cannabis and hops are sold as extracts of their most valuable components, such as, terpenes, terpene derivatives, cannabinoids, and flavonoids, found in the trichomes (e.g., resin glands in cannabis and lupulin glands in hops).
  • terpenes terpene derivatives
  • cannabinoids cannabinoids
  • flavonoids found in the trichomes
  • these components have a wide array of uses, ranging from taste and aroma to medicinal uses.
  • terpenes terpene derivatives
  • cannabinoids cannabinoids
  • flavonoids flavonoids
  • trichomes of a plant material e.g., cannabis or hops
  • these methods can maximize the amount of lightweight terpenes, terpene derivatives (e.g., terpenoids), cannabinoids, and/or flavonoids (as well as other lightweight molecules, such as, thiols or other sulfurous compounds) extracted and minimize the amount of heat and solvent used, in some aspects eliminating solvents from the extraction process altogether.
  • These methods can yield a higher-quality extract with fewer or no residual byproducts (e.g., solvents) while minimizing overall operating costs.
  • a method of plant extraction including: a) providing a plurality of trichomes from a plant; b) combining the trichomes with a fluid to form a mixture; c) inducing cavitation in the mixture to release at least one desired compound from the trichome into the fluid; and d) separating out the at least one desired compound from the mixture; wherein the at least one desired compound is a terpene, a terpene derivative (e.g., a terpenoid), a cannabinoid, or a flavonoid.
  • a method of plant extraction including: a) providing a plurality of trichomes from a plant at a first temperature below about 35°C; b) applying a negative pressure to the trichomes to volatize at least one desired compound from the trichomes to form a gaseous plant extract; and c) condensing the gaseous plant extract at a second temperature below about 25°C to form a liquid plant extract; wherein the at least one desired compound is a terpene, a terpene derivative (e.g., a terpenoid), a cannabinoid, or a flavonoid.
  • a method of plant extraction including a) providing a wet plant material including a plurality of trichomes; b) freezing the wet plant material to a first temperature below about 0°C; c) agitating the wet plant material to separate the trichomes from the wet plant material; d) warming the trichomes to a second temperature below about 35°C and applying a negative pressure to the trichomes to volatize at least a first desired compound from the trichomes to form a gaseous plant extract; f) condensing the gaseous plant extract at a third temperature below about 25 °C to form a first liquid plant extract; g) combining the trichomes with a fluid to form a mixture; h) inducing cavitation in the mixture to release at least a second desired compound from the trichome into the fluid; and i) separating out the second desired compound from the mixture; wherein each of the desired compounds is a ter
  • liquid plant extract prepared from any of the disclosed methods, including a greater quantity of at least one monoterpene (e.g., myrcene, pinene, limonene) than a control liquid plant extract prepared from a conventional method.
  • monoterpene e.g., myrcene, pinene, limonene
  • FIGURE 1 depicts an example method of producing cannabis extract including trichome harvest, vacuum extraction of trichomes, and cavitation extraction of trichomes.
  • FIGURE 2 depicts an example method of trichome harvest.
  • FIGURE 3 depicts an example method of vacuum extraction of trichomes.
  • FIGURE 4 depicts another example method of vacuum extraction of trichomes.
  • FIGURE 5 depicts an example method of cavitation extraction of trichomes.
  • terpenes are valuable plant commodities, however, only a small fraction of the plant itself is ultimately sold. Both plants are commercially sold as extracts of the assorted terpenes, terpene derivatives (e.g., terpenoids), cannabinoids, or flavonoids found in each plant’s trichomes, which can confer benefits ranging from taste and smell to pain and anxiety relief.
  • terpene derivatives e.g., terpenoids
  • cannabinoids cannabinoids
  • flavonoids found in each plant’s trichomes
  • a “trichome” can refer to either a “glandular trichome,” which produces metabolites like terpenoids, flavonoids, etc., or a “non-glandular trichome,” which serves as structural protection. Many plants, algae, lichens, and protists produce trichomes. As used herein, the term “trichome” most often refers to a glandular trichome from a plant (e.g., resin glands from cannabis and lupulin glands from hops) which contains terpene, a terpene derivative (e.g., a terpenoid), a cannabinoid, or a flavonoid that can be isolated.
  • a terpene derivative e.g., a terpenoid
  • cannabinoid e.g., a cannabinoid
  • terpene refers broadly to any organic hydrocarbon compound built from isoprene subunits, which are 5 carbon structures. Terpenes are most broadly classified by the number of isoprene units from which they were constructed: monoterpenes (two isoprene units), sesquiterpenes (three isoprene units), diterpenes (four isoprene units), sesterterpenes (five isoprene units), triterpenes (six isoprene units), sesquarterpenes (seven isoprene units), tetraterpenes (eight isoprene units), and polyterpenes (nine or more isoprene units).
  • a terpene can be subjected to further modifications and form a "terpene derivative", for example, via the addition or removal of carbon atoms, the addition of functional groups, ring formation, etc.
  • terpenoid or “isoprenoid” refers to a terpene that further includes oxygen-containing functional groups.
  • flavonoid refers to a terpene that generally has a 15- carbon skeleton, which includes two phenyl rings and a third heterocyclic ring (typically containing oxygen).
  • cannabinoid refers to a terpene which can interact with a cannabinoid receptor 1 (CBi) or a cannabinoid receptor 2 (CB2) in a human.
  • Cannabinoids include “Phyto cannabinoids,” which are produced by the cannabis plant, “endocannabinoids,” which are produced by mammals, and synthetic cannabinoids.
  • cannabinoid is primarily used herein to refer to Phyto cannabinoids.
  • an example method of plant extraction 100 which includes three primary stages: a trichome harvest stage 101, a vacuum extraction stage 103, and a cavitation extraction stage 105.
  • the trichome harvest stage 101 starts by providing a wet plant material 102 including a plurality of trichomes.
  • the wet plant material 102 is frozen 104 to a first temperature below about 0°C to minimize evaporation of desired compounds in the processing which follows.
  • the frozen wet plant material 102 is then agitated 106 to separate out the trichomes 108, which yields trichomes 108 and depleted wet plant material 110.
  • the depleted wet plant material 110 does not include a majority of the trichomes.
  • the trichomes 108 are warmed to a second temperature below about 35°C, and a negative pressure is applied 112 to the trichomes 108 to volatize at least a first desired compound from the trichomes to form a gaseous plant extract 114.
  • the negative pressure is below about 760 torr, or below about 500 torr, or below about 100 torr, or below about 1 torr, or below about 10' 2 torr, or below about 10' 6 torr, or below about 10' 10 torr.
  • the negative pressure may be applied to the trichomes 108 using a vacuum pump or a series of vacuum pumps coupled to a sealable chamber.
  • the gaseous plant extract 114 is condensed 116 at a third temperature below about 25 °C to form a first liquid plant extract 118.
  • the trichomes 108 are combined 120 with a fluid 122 to form a mixture 124. Cavitation is induced 126 in the mixture 124 to release at least a second desired compound 130 from the trichomes 108 into the fluid 122. Cavitation may be induced using a device, such as that disclosed in U.S. Patent Nos. 10,222,056 and 11,320,142, which are incorporated herein by reference in their entireties. Finally, the second desired compound 130 is separated out 128, which yields a depleted mixture 132 without a majority of the second desired compound 130.
  • the first liquid plant extract 118 may include a mixture of lightweight terpenes, terpene derivatives (e.g., a terpenoids), cannabinoids, or flavonoids, and the second desired compound 130 may be heavier weight hop oils or cannabinoids.
  • the example method of FIG. 1 produces two different distinct separate compositions, i.e., lightweight terpenes and heavier hops oils/cannabinoids, both of which may be re-combined or mixed into a final product (e.g., beer, liquor, tincture, or cartridge wax) to protect the integrity of both separates.
  • each composition may be applied together or separately to achieve a desired taste profile.
  • the two separate compositions can each be frozen and used for additional batches, each of which will retain the same flavor and fragrance profile that can be used whenever needed for many years.
  • each of the desired first and second compounds may be a terpene, a terpenoid, a cannabinoid, or a flavonoid.
  • the plant is cannabis and the trichomes are resin glands.
  • the plant is hops and the trichomes are lupulin glands.
  • the trichomes are from any other essence or essential oil producing plant or any organism that produces trichomes that contain a desirable compound.
  • the at least one desired compound is aristolene epoxide, cis-a-bisabolene, a- bisabolol, camphene, 5-3-carene, P-caryophyllene, caryophyllene oxide, p-cymene, eucalyptol, eudesma-3,7(l l)-diene, P-famesene, exo-fenchol, geraniol, guaiol, r-gurjunene, a-humulene (a-caryophyllene), iso-borneol, d-limonene, linalool, linalool oxide, P-myrcene, nerolidol, ocimene, phytol, trans-pinalol, a-pinene, P-pinene, iso-pulegol, a-selenene, a-terpinene, y-
  • liquid plant extract prepared from the disclosed method of plant extraction, including a greater quantity of at least one monoterpene (e.g., myrcene, pinene, limonene) than a control liquid plant extract prepared from an alternate (e.g., conventional) method.
  • the method produces multiple liquid plant extracts.
  • the multiple liquid plant extracts are combined.
  • a wet plant material 102 including a plurality of trichomes is provided.
  • the term “wet plant material” refers to a harvested plant material that has not been dried out or spoiled. Depending on the plant, the harvested plant material stays “wet” for only a short period of time and, as such, must be processed quickly after harvest.
  • the plant is cannabis and the trichomes are resin glands.
  • the plant is hops and the trichomes are lupulin glands.
  • the trichomes are from any other essence or essential oil producing plant or any organism that produces trichomes that contain a desirable compound.
  • the wet plant material 102 first undergoes a discarding step 202 where fan leaves (e.g., large mature leaves) and leaves without trichomes 204 are discarded.
  • the branches 210 are separated out 206 from the remainder of the wet plant material, which yields depleted wet plant material 208 without most of the branches 210.
  • the branches 210 are then bucked 212 to separate the buds 214 from the branches 216.
  • the bucking step 212 is performed manually.
  • the bucking step 212 is performed using a bucking machine.
  • the buds 214 then undergo the remainder of the trichome harvesting method.
  • any one of the discarding 202, separating 206, and bucking 212 steps can be omitted, and the wet plant material 102 undergoes the remainder of the trichome harvesting method.
  • the wet plant material 102 or the buds 214 can be milled or macerated.
  • the wet plant material 102 or the buds 214 can be dried.
  • the buds 214 are frozen 104 to a first temperature below about 0°C using a chilled fluid 218.
  • the chilled fluid 218 is water, glycerol, air, or another suitable refrigerant that could be identified by one of skill in the art.
  • the chilled fluid 218 is liquid nitrogen.
  • the first temperature is below about 0°C, or below about -10°C, or below about -20°C, or below about -30°C, or below about -40°C, or below about -50°C, or below about -60°C, or below about -70°C, or below about -80°C, or below about -90°C, or below about -100°C.
  • the buds 214 are immersed in the chilled fluid 218. In some aspects, the buds 214 are sprayed with the chilled fluid 218. In some aspects, the buds 214 are placed in or passed through a chamber that is cooled by the chilled fluid 218. In some aspects, the frozen buds 214 can be milled or macerated.
  • the frozen buds 214 are agitated 106 to separate out the trichomes 108, which yields depleted buds 220 without a majority of the trichomes 108.
  • the agitating step 106 is performed using a screened vibrating rack.
  • the agitating step 106 is performed using a screened tumbler or rotating drum.
  • the agitating step 106 further includes separating the trichomes 108 by size using a sieve or a series of sieves. [0038] In some aspects, further separation of the trichomes 108 from unwanted contaminants or debris is performed with a static electricity process.
  • a plasma static process can effectuate electrostatic separation and remove stalks, plant particles, and other contaminants from the trichome 108 heads.
  • Dry or fresh frozen plant material can be fed into a plasma static device, wherein compressed air can carry the plant material to a diffuser transforming the plant material into a falling stream of particles.
  • Two plasma-charged plates pull particles into each direction as they fall.
  • Trichome 108 heads collect on one plate of the device and stalks, dirt, pistils, and plant particles collect on the opposite side. Only compressed air and static electricity are used in the process.
  • An electrostatic separation process can provide low power consumption, semi-automated systems, and microclimate cabinets. It can work with dry or stable fresh frozen plant biomass. It can remove stalks from trichomes 108. It can remove immature trichomes 108. No chemicals are needed. And none of the biomass particle chemistry is altered.
  • the agitating step 106 is performed at a negative pressure. In some aspects, the agitating step 106 is performed at a temperature below about 0°C, or below about -10°C, or below about -20°C, or below about -30°C, or below about -40°C, or below about - 50°C, or below about -60°C, or below about -70°C, or below about -80°C, or below about - 90°C, or below about -100°C.
  • the freezing 104 and agitating 106 steps can be performed on any portion or component or all of the wet plant material 102 if any of the discarding 202, separating 206, and bucking 212 steps are omitted.
  • the method of harvesting trichomes yields more light molecular weight chemical compounds (terpenes, terpene derivatives (e.g., a terpenoids), cannabinoids, or flavonoids) in the trichomes than conventional harvesting methods that involve drying the wet plant material.
  • the method of harvesting trichomes confers lower shipping and storage costs than conventional harvesting methods that harvest the entire plant or entire buds.
  • the method of harvesting trichomes can be performed in conjunction with the method of a plant extraction via cavitation and/or the method of plant extraction via vacuum extraction.
  • the disclosed method can be performed in conjunction with conventional plant extraction methods (e.g., winterization).
  • a plurality of trichomes 108 from a plant are provided at a temperature below about 35°C. In some aspects, the temperature is below about 35°C, or below about 30°C, or below about 25°C, or below about 20°C.
  • a first negative pressure is applied 312a to the trichomes 108 to volatize at least a first desired compound to form a first gaseous plant extract 314a, which is then condensed 316a at a first temperature below about 25 °C into a first liquid plant extract 318a.
  • a second negative pressure is applied 312b to the trichomes 108 to volatize at least a second desired compound to form a second gaseous plant extract 314b, which is then condensed 316b at a second temperature below about 25°C into a second liquid plant extract 318b.
  • a third negative pressure is applied 312c to the trichomes 108 to volatize at least a third desired compound to form a third gaseous plant extract 314c, which is then condensed 316c at a third temperature below about 25°C into a third liquid plant extract 318c.
  • each of the first negative pressure, the second negative pressure, and the third negative pressure is below about 760 torr, or below about 500 torr, or below about 100 torr, or below about 1 torr, or below about 10' 2 torr, or below about 10' 6 torr, or below about 10' 10 torr.
  • the negative pressure is the same in each repetition.
  • the negative pressure is lowered in each repetition by about 10 torr to about 100 torr, including exemplary values of about 15 torr, about 20 torr, about 25 torr, about 30 torr, about 35 torr, about 40 torr, about 45 torr, about 50 torr, about 55 torr, about 60 torr, about 65 torr, about 70 torr, about 75 torr, about 80 torr, about 85 torr, about 90 torr, and about 95 torr, such that each of the first liquid plant extract 318a, the second liquid plant extract 318b, and the third liquid plant extract 318c has a different chemical composition.
  • the negative pressure is lowered by the same amount in each subsequent repetition.
  • the negative pressure is lowered in increasing increments with subsequent repetitions. In some aspects, the negative pressure is lowered in decreasing increments with subsequent repetitions. In some aspects, microwaves or ultrasonic waves can be applied to the trichomes 108 during any of the applying negative pressure steps to facilitate volatilization.
  • each of the first, second and third temperatures is below from about 25°C to about -200°C. In some aspects, each of the first, second, and third temperatures is below about 25°C, or below about 20°C, or below about 10°C, or below about 0°C, or below about -10°C, or below about -20°C, or below about -30°C, or below about -40°C, or below about -50°C, or below about -60°C, or below about -70°C, or below about -80°C, or below about -90°C, or below about -100°C, or below about -110°C, or below about -120°C, or below about -130°C, or below about -140°C, or below about -150°C, or below about -160°C, or below about -170°C, or below about -180°C, or below about -190°C, or below about -200°C. In some aspects, the first
  • the third applying negative pressure 312c and third condensing 316c steps are omitted, and only first and second liquid plant extracts (318a, 318b) are formed.
  • the applying negative pressure and condensing steps are iterated more than three times, and negative pressure is lowered by about 10 torr to about 100 torr in each additional repetition, including exemplary values of about 15 torr, about 20 torr, about 25 torr, about 30 torr, about 35 torr, about 40 torr, about 45 torr, about 50 torr, about 55 torr, about 60 torr, about 65 torr, about 70 torr, about 75 torr, about 80 torr, about 85 torr, about 90 torr, or about 95 torr.
  • the negative pressure is lowered by the same amount in each subsequent repetition. In some aspects, the negative pressure is lowered in increasing increments with subsequent repetitions. In some aspects, the negative pressure is lowered in decreasing
  • the method is executed in a chamber that is coupled to a vacuum pump, wherein the vacuum pump applies a negative pressure to the chamber; the vacuum pump is distanced from the chamber by a conduit; and at least one cold trap is operably coupled to the conduit, wherein the at least one cold trap condenses the gaseous plant extract.
  • the chamber is purged with N2, CO2, or another inert gas before use to prevent oxidation and/or degradation of the desired compounds.
  • a plant extraction via vacuum extraction 103 wherein multiple, user- selected, cold traps (e.g., between two, three, four, or five) are operably coupled to the conduit and each cold trap operates at a subsequently lower temperature (i.e., starting from the cold trap closest to the chamber and going to the cold trap closest to the vacuum pump) to condense the gaseous plant extract to form multiple liquid plant extracts.
  • a plurality of trichomes 108 from a plant material are provided at a temperature below about 35°C, and a negative pressure is applied 112 to the trichomes 108 to volatize at least a first desired compound to form a gaseous plant extract 114.
  • the negative pressure is below about 760 torr, or below about 500 torr, or below about 100 torr, or below about 1 torr, or below about 10' 2 torr, or below about 10' 6 torr, or below about 10' 10 torr.
  • the temperature is below about 35°C, or below about 30°C, or below about 25°C, or below about 20°C.
  • microwaves or ultrasonic waves can be applied to the trichomes 108 during the applying negative pressure step to facilitate volatilization.
  • another portion of the gaseous plant extract 114 is condensed 416b at a second temperature below about 25°C into a second liquid plant extract 418b.
  • another portion of the gaseous plant extract 114 is condensed 416c at a third temperature below about 25°C into a third liquid plant extract 418c.
  • another portion of the gaseous plant extract 114 is condensed 416d at a fourth temperature below about 25°C into a fourth liquid plant extract 418d.
  • another portion of the gaseous plant extract 114 is condensed 416e at a fifth temperature below about 25°C into a fifth liquid plant extract 418e.
  • each of the first, second, third, fourth, and fifth temperatures is below from about 25 °C to about -200°C . In some aspects, each of the first, second, third, fourth, and fifth temperatures is below about 25 °C, or below about 20°C, or below about 10°C, or below about 0°C, or below about -10°C, or below about -20°C, or below about -30°C, or below about -40°C, or below about -50°C, or below about -60°C, or below about -70°C, or below about -80°C, or below about -90°C, or below about -100°C, or below about -110°C, or below about -120°C, or below about -130°C, or below about -140°C, or below about -150°C, or below about -160°C, or below about -170°C, or below about -180°C, or below about -190°C, or below about
  • the first, second, third, fourth, and fifth temperatures are subsequently lowered by from about 10°C to about 30°C, including exemplary values of about 12°C, about 14°C, about 16°C, about 18°C, about 20°C, about 22°C, about 24°C, about 26°C, or about 28°C.
  • the temperature is lowered by the same amount across subsequent cold traps. In some aspects, the temperature is lowered in increasing increments across subsequent cold traps. In some aspects, the temperature is lowered in decreasing increments across subsequent cold traps.
  • Each of the first, second, third, fourth, and fifth liquid plant extracts (418a, 418b, 418c, 418d, 418e) has a different chemical composition.
  • Each of the condensation steps 416a, 416b, 416c, 416d, and 416e collectively define a method of fractional condensation 420.
  • one or more of the condensation steps in the example method 103’ (316a, 316b, 316c) can be replaced with the method of fractional condensation 420.
  • each of the desired compounds is a terpene, a terpenoid, a cannabinoid, or a flavonoid.
  • the plant is cannabis and the trichomes are resin glands.
  • the plant is hops and the trichomes are lupulin glands.
  • the trichomes are from any other essence or essential oil producing plant or any organism that produces trichomes that contain a desirable chemical compound.
  • the at least one desired compound is aristolene epoxide, cis-a-bisabolene, a- bisabolol, camphene, 5-3-carene, P-caryophyllene, caryophyllene oxide, p-cymene, eucalyptol, eudesma-3,7(l l)-diene, P-famesene, exo-fenchol, geraniol, guaiol, r-gurjunene, a-humulene (a-caryophyllene), iso-borneol, d-limonene, linalool, linalool oxide, P-myrcene, nerolidol, ocimene, phytol, trans-pinalol, a-pinene, P-pinene, iso-pulegol, a-selenene, a-terpinene, y-
  • liquid plant extract prepared from any of the disclosed methods of plant extraction via vacuum extraction, including a greater quantity of at least one monoterpene (e.g., myrcene, pinene, limonene) than a control liquid plant extract prepared from an alternate method.
  • the method produces multiple liquid plant extracts. In some extracts, the multiple liquid plant extracts are combined.
  • the method of plant extraction via vacuum extraction yields more lightweight chemical compounds (terpenes, terpene derivatives (e.g., a terpenoids), cannabinoids, or flavonoids) in the trichomes than conventional extraction methods.
  • the method of plant extraction via vacuum extraction requires less solvent than conventional extraction methods.
  • the method of plant extraction via vacuum extraction can be performed on trichomes obtained by the method of harvesting trichomes.
  • the method of plant extraction via vacuum extraction can be performed on trichomes obtained by conventional harvest methods.
  • the method of plant extraction via vacuum extraction can be performed in conjunction with the method of cavitation extraction to extract any remaining terpenes, terpene derivatives (e.g., a terpenoids), cannabinoids, or flavonoids, that were not removed by vacuum extraction.
  • the method of plant extraction via vacuum extraction can be performed as a sole extraction method.
  • the method of plant extraction via vacuum extraction can be used in conjunction with another conventional plant extraction method (e.g., winterization).
  • cavitation refers to a spontaneous formation and implosion of small vapor cavities in a liquid.
  • the implosion can be destructive, but if controlled, can be used to advantageously lyse or homogenize a solid.
  • a plurality of trichomes 108 from a plant are provided and combined 120 with a fluid 122 to form a mixture 124.
  • the fluid is water, alcohol, glycerin, propane, butane, or a mixture thereof. Cavitation is then induced 126 in the mixture 124.
  • the combining 120 and inducing cavitation 126 steps occur concurrently.
  • the combining step 120 occurs in a mixing vessel (e.g., a tank with an impeller) to provide a solid suspension of the trichomes 108 in the fluid 122, and the solid suspension is transported to a separate vessel for the inducing cavitation step 126.
  • cavitation is induced using a stirred tank having a rotor, wherein the rotor has a design that induces cavitation when the rotor is spun (e.g., pores). Rotation of the rotor within the tank induces highly energetic cavitation events in the mixture. These cavitation events induce highly energetic shock waves and corresponding highly intense and rapid pressure fluctuations that propagate through the mixture.
  • This environment liberates terpenes, terpene derivatives (e.g., a terpenoids), cannabinoids, or flavonoids, from the trichomes within the mixture, and these compounds become dissolved, entrained, or suspended within the fluid of the mixture.
  • the stirred tank further includes a heat exchanger to control heat generated by the cavitation process.
  • the cavitation further facilitates lysis of the trichome membrane.
  • Trichomes are often surrounded by a membrane, which can inhibit full extraction of the desirable compounds.
  • the lysis coupled with cavitation provides increased yield and selectivity.
  • the at least one desired compound 130 is separated out 128, which yields a depleted mixture 532 without a majority of the at least one desired compound 130.
  • the separating step 128 is executed using a centrifugal separator, a membrane filter, and/or a ceramic filtration apparatus, such as those conventional in the art.
  • the separating step 128 includes a separation using only one apparatus.
  • the separating step 128 includes a separation using an apparatus of increasing selectivity (e.g., increasingly smaller particle size).
  • a brine 502 can be added to the mixture 124 to facilitate separating out 128 the at least one desired compound 130.
  • the brine solution includes sodium chloride, sodium sulfate, sodium phosphate, or another suitable ionic salt or combinations thereof.
  • a brine is not added.
  • the mixture 124 is chilled to facilitate separating out 128 the at least one desired compound 130. In some aspects, the mixture 124 is chilled to a temperature below about 25 °C, or below about 20°C, or below about 15°C, or below about 10°C, or below about 5°C, or below about 0°C.
  • the mixture 124 is chilled using a refrigerated tank (e.g., double walled storage tank). In some aspects, the mixture 124 is chilled using a refrigerated environment (e.g., cold room). In some aspects, the mixture 124 is not chilled.
  • a refrigerated tank e.g., double walled storage tank
  • a refrigerated environment e.g., cold room
  • the mixture 124 is not chilled.
  • the depleted mixture 532 is at least partially recycled back into the mixture 124 in the combining step 120 to further release any remaining desired compound from the trichomes recovered in the separating step 128 by re-subjecting the recovered trichomes to the inducing cavitation 126 and separating 128 steps.
  • all the depleted mixture 532 containing all of the recovered trichomes is recycled back into the mixture 124.
  • a portion of the depleted mixture 532a containing a portion of the recovered trichomes is recycled back into the mixture 124, and the remaining mixture 532b containing the remaining recovered trichomes is purged (e.g., discarded).
  • all the depleted mixture 532 is discarded.
  • each of the desired compounds is a terpene, a terpenoid, a cannabinoid, or a flavonoid.
  • the plant is cannabis and the trichomes are resin glands.
  • the plant is hops and the trichomes are lupulin glands.
  • the trichomes are from any other essence or essential oil producing plant or any organism that produces trichomes that contain a desirable compound.
  • liquid plant extract prepared from any of the disclosed methods of plant extraction via cavitation extraction, including a greater quantity of at least one monoterpene (e.g., myrcene, pinene, limonene) than a control liquid plant extract prepared from an alternate (e.g., conventional) method.
  • monoterpene e.g., myrcene, pinene, limonene
  • the method of plant extraction via cavitation extraction yields more lighter molecular weight chemical compounds (terpenes, terpene derivatives (e.g., a terpenoids), cannabinoids, or flavonoids) in the trichomes than provided by conventional extraction methods.
  • the method of plant extraction via cavitation extraction requires less solvent than conventional extraction methods.
  • the method of plant extraction via cavitation extraction can be performed on trichomes obtained by the method of harvesting trichomes.
  • the method of plant extraction via cavitation extraction can be performed on trichomes obtained by conventional harvest methods.
  • the method of plant extraction via cavitation extraction can be performed in conjunction with the method of vacuum extraction to extract any remaining terpenes, terpene derivatives (e.g., a terpenoids), cannabinoids, or flavonoids, that were not removed by vacuum extraction.
  • the method of plant extraction via cavitation extraction can be performed as a sole extraction method.
  • the method of plant extraction via cavitation extraction can be used in conjunction with another conventional plant extraction method (e.g., winterization).
  • Ranges can be expressed herein as from “about” one particular value and/or to “about” another particular value. When such a range is expressed, another aspect includes from the one particular value and/or to the other particular value. Similarly, when values are expressed as approximations, by use of the antecedent “about,” it will be understood that the particular value forms another aspect. It should be further understood that the endpoints of each of the ranges are significant both in relation to the other endpoint, and independently of the other endpoint.

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Abstract

L'invention concerne un procédé d'extraction de plantes consistant à : (a) fournir une pluralité de trichomes provenant d'une plante à une première température inférieure à environ 35 °C ; et soit : (b1) appliquer une pression négative aux trichomes pour volatiliser au moins un composé souhaité à partir des trichomes pour former un extrait de plante gazeux ; et (c1) condenser l'extrait de plante gazeux à une seconde température inférieure à environ 25 °C pour former un extrait de plante liquide ; soit (b2) combiner les trichomes avec un fluide pour former un mélange ; (c2) induire une cavitation dans le mélange pour libérer au moins un composé souhaité du trichome dans le fluide ; et (d2) séparer le ou les composés souhaités du mélange ; le ou les composés souhaités étant un terpène, un terpénoïde, un cannabinoïde ou un flavonoïde.
PCT/US2024/057769 2023-11-27 2024-11-27 Procédé permettant d'isoler des terpènes à partir de trichomes Pending WO2025117755A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016205923A1 (fr) * 2015-06-25 2016-12-29 Compressed Perforated Puck Technologies Inc. Pilule de source végétale à ingérer et procédé
US20200237840A1 (en) * 2016-04-18 2020-07-30 Kenneth Michael MORROW Isolation of plant extracts
US20210023155A1 (en) * 2019-07-22 2021-01-28 Marquette Analytica Cannabis screw conveyor processor and membrane system and methods
US20220315870A1 (en) * 2017-09-12 2022-10-06 Yakima Chief Hops, Inc Cryogenic hop lupulin or cannabis trichome pellets

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016205923A1 (fr) * 2015-06-25 2016-12-29 Compressed Perforated Puck Technologies Inc. Pilule de source végétale à ingérer et procédé
US20200237840A1 (en) * 2016-04-18 2020-07-30 Kenneth Michael MORROW Isolation of plant extracts
US20220315870A1 (en) * 2017-09-12 2022-10-06 Yakima Chief Hops, Inc Cryogenic hop lupulin or cannabis trichome pellets
US20210023155A1 (en) * 2019-07-22 2021-01-28 Marquette Analytica Cannabis screw conveyor processor and membrane system and methods

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