Process for isolating terpenes from trichomes

Abstract

A method of plant extraction comprising: (a) providing a plurality of trichomes from a plant at a first temperature below about 35 °C; and either: (b1) applying a negative pressure to the trichomes to volatize at least one desired compound from the trichomes to form a gaseous plant extract; and (c1) condensing the gaseous plant extract at a second temperature below about 25 °C to form a liquid plant extract; or (b2) combining the trichomes with a fluid to form a mixture; (c2) inducing cavitation in the mixture to release at least one desired compound from the trichome into the fluid; and (d2) separating out the at least one desired compound from the mixture; wherein the at least one desired compound is a terpene, a terpenoid, a cannabinoid, or a flavonoid.

Description

PROCESS FOR ISOLATING TERPENES FROM TRICHOMESRELATED APPLICATIONS

[0001] This application claims priority under 35 U.S.C. §119(e) to U.S. Provisional Patent Application No. 63 / 602,754 filed November 27, 2023, which is incorporated herein by reference.BACKGROUND

[0002] 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). These components have a wide array of uses, ranging from taste and aroma to medicinal uses. As such, there exists a continued need for improved extraction of components from cannabis and hops that provide the highest quality extracts without high operating costs or residual byproducts. These needs and others are at least partially satisfied by the present disclosure.

[0003] Conventional methods of producing cannabis and hops extracts are usually very heat intensive. Typically, the plant or its buds are dried, macerated, and soaked in a chilled solvent. The chilled solvent serves to extract out desired compounds (e.g., terpenes or cannabinoids) from other compounds in the plant (e.g., fats or wax) in a process called winterization. This can include additional solvent dissolution steps to further extract the plant or to yield a specific compound from the plant. To isolate terpenes, the macerated plant materials are sieved off, and the extract is heated to evaporate off the solvent from the terpenes. Not only does this increase the operating costs of such methods, but it also ultimately evaporates off a majority of small, lightweight terpenes (and other lightweight molecules, such as, thiols or other sulfurous compounds) found in the trichomes that are the primary contributors to the taste and aroma of the extract. As such, there is a need for a method that uses as little heat as possible to form an extract of superior quality with a significantly decreased heating cost.SUMMARY

[0004] Disclosed herein are methods for isolating terpenes, terpene derivatives (e.g., terpenoids), cannabinoids, and / or flavonoids from trichomes of a plant material (e.g., cannabisor hops), specifically, the resin glands of cannabis or the lupulin glands of 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.

[0005] In an aspect, provided is a method of plant extraction, the method 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.

[0006] In another aspect, provided is a method of plant extraction, the method 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.

[0007] In another aspect, provided is a method of plant extraction, the method 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 terpene, a terpene derivative (e.g., a terpenoid), a cannabinoid, or a flavonoid.

[0008] In another aspect, provided is a 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.

[0009] Other systems, methods, features and / or advantages will be or may become apparent to one with skill in the art upon examination of the following drawings and detailed description. It is intended that all such additional systems, methods, features and / or advantages be included within this description and be protected by the accompanying claims.

[0010] Further embodiments, forms, features, aspects, benefits, objects, and advantages of the invention shall become apparent from the following detailed description and the attached drawings, which are an integral part of the present disclosure.BRIEF DESCRIPTION OF DRAWINGS

[0011] The foregoing summary, as well as the following detailed description of illustrative implementations, is better understood when read in conjunction with the appended drawings. For the purpose of illustrating the implementations, there is shown in the drawings example constructions of the implementations; however, the implementations are not limited to the specific methods and instrumentalities disclosed. In the drawings:

[0012] FIGURE 1 depicts an example method of producing cannabis extract including trichome harvest, vacuum extraction of trichomes, and cavitation extraction of trichomes.

[0013] FIGURE 2 depicts an example method of trichome harvest.

[0014] FIGURE 3 depicts an example method of vacuum extraction of trichomes.

[0015] FIGURE 4 depicts another example method of vacuum extraction of trichomes.

[0016] FIGURE 5 depicts an example method of cavitation extraction of trichomes.DETAILED DESCRIPTION

[0017] It is appreciated that certain features of the disclosure, which are, for clarity, described in the context of separate aspects, can also be provided in combination with a single aspect. Conversely, various features of the disclosure, which are, for brevity, described in the context of a single aspect, can also be provided separately or in any suitable sub combination. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. Methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present disclosure.

[0018] In an embodiment, disclosed herein is a method of extracting terpenes from trichomes, particularly from the resin glands of cannabis or the lupulin glands of hops. Cannabis and hops 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.

[0019] 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.

[0020] As used herein, the term “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).

[0021] Once the isoprene -based skeleton is constructed, 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.

[0022] As used herein, the term “terpenoid” or “isoprenoid” refers to a terpene that further includes oxygen-containing functional groups.

[0023] As used herein, the term “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).

[0024] As used herein, the term “cannabinoid” refers to a terpene which can interact with a cannabinoid receptor 1 (CBi) or a cannabinoid receptor 2 (CB2) in a human.

[0025] Cannabinoids" include “Phyto cannabinoids,” which are produced by the cannabis plant, “endocannabinoids,” which are produced by mammals, and synthetic cannabinoids. However, the term “cannabinoid” is primarily used herein to refer to Phyto cannabinoids.

[0026] With reference to FIG. 1, in an aspect, provided is 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. Next, 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 isthen 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.

[0027] In the vacuum extraction stage 103, 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. In some aspects, 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 10'2torr, or below about 10'6torr, or below about 10'10torr. For example, 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.

[0028] In the cavitation extraction stage 105, 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.

[0029] For example, 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. Thus, 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. Further, 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.

[0030] In the example method 100, each of the desired first and second compounds may be a terpene, a terpenoid, a cannabinoid, or a flavonoid. In some aspects, the plant is cannabis and the trichomes are resin glands. In some aspects, the plant is hops and the trichomes are lupulin glands. In some aspects, the trichomes are from any other essence or essential oil producing plant or any organism that produces trichomes that contain a desirable compound.In some aspects, 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- terpinene, a-terpineol, terpinolene, ylangene, cannabinol (CBN), cannabinolic acid (CBNA), DELTA (9)-tetrahydrocannabinol (DELTA (9)-THC), DELTA (9)-tetrahydrocannabinolic acid (DELTA (9)-THCA), DELTA (9)-cannabidiol (DELTA (9)-CBD), DELTA (9)- tetrahydrocannabidiolic acid (DELTA (9)-CBDA), DELTA (8)-tetrahydrocannabinol (DELTA (8)-THC), DELTA (8)-tetrahydrocannabinolic acid (DELTA (8)-THCA), DELTA (8)-tetrahydrocannabidiol (DELTA (8)-CBD), DELTA (8)-tetrahydrocannabidiolic acid (DELTA (8)-CBDA), DELTA (9)-tetrahydrocannabivarin (DELTA (9)-THV), cannabigerol (CBG), cannabigerolic acid (CBGA), cannabichromene (CBC), cannabichromenic acid (CBCA), cannabicyclol (CBL), cannabicyclolic acid (CBLA), cannabivarin (CBV), tetrahydrocannabivarin (THCV), cannabidivarin (CBDV), cannabichromevarin (CBCV), cannabigerovarin (CBGV), cannabigerol monomethyl ether (CBGM), beta-caryophyllene epoxide, mentha-l,8(9)-dien-5-ol, pulegone, limonene, limonene oxide, alpha-terpinene, terpinen-4-ol, carvacrol, carvone, 1,8-cineole, p-cymene, fenchone, pulegone- 1,2-epoxide, beta-myrcene, cannflavin A, or cannflavin B .

[0031] In another aspect, provided is a 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. In some aspects, the method produces multiple liquid plant extracts. In some aspects, the multiple liquid plant extracts are combined.

[0032] The following implementations of the present disclosure are intended to describe additional details of the aforementioned three phases (trichome harvest 101, vacuum extraction 103, and cavitation extraction 105) of the plant extraction method. It should be understood that any of the three phases can be performed alone or in conjunction with another phase or with another conventional harvest / extraction method.TRICHOME HARVEST

[0033] With reference to FIG. 2, in an aspect, provided is an example method of harvesting trichomes 101’. First, a wet plant material 102 including a plurality of trichomes is provided. As used herein, the term “wet plant material” refers to a harvested plant material that has notbeen 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. In some aspects, the plant is cannabis and the trichomes are resin glands. In some aspects, the plant is hops and the trichomes are lupulin glands. In some aspects, the trichomes are from any other essence or essential oil producing plant or any organism that produces trichomes that contain a desirable compound.

[0034] 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. Next, 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. In some aspects, the bucking step 212 is performed manually. In some aspects, the bucking step 212 is performed using a bucking machine. The buds 214 then undergo the remainder of the trichome harvesting method. In some aspects, 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. In some aspects, the wet plant material 102 or the buds 214 can be milled or macerated. In some aspects, the wet plant material 102 or the buds 214 can be dried.

[0035] The buds 214 are frozen 104 to a first temperature below about 0°C using a chilled fluid 218. In some aspects, the chilled fluid 218 is water, glycerol, air, or another suitable refrigerant that could be identified by one of skill in the art. In some aspects, the chilled fluid 218 is liquid nitrogen. In some aspects, 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.

[0036] In some aspects, 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.

[0037] Finally, 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. In some aspects, the agitating step 106 is performed using a screened vibrating rack. In some aspects, the agitating step 106 is performed using a screened tumbler or rotating drum. In some aspects, 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. For example, 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.

[0039] In some aspects, 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.

[0040] 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.

[0041] In some aspects, 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. In some aspects, the method of harvesting trichomes confers lower shipping and storage costs than conventional harvesting methods that harvest the entire plant or entire buds. In some aspects, 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. In some aspects, the disclosed method can be performed in conjunction with conventional plant extraction methods (e.g., winterization).VACUUM EXTRACTION OF TRICHOMES

[0042] With reference to FIG. 3, in an aspect, provided is an example method of a plant extraction via vacuum extraction 103’. A plurality of trichomes 108 from a plant are providedat 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. Finally, 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.

[0043] In some aspects, 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 10'2torr, or below about 10'6torr, or below about 10'10torr. In some aspects, the negative pressure is the same in each repetition. In some aspects, 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. In some aspects, 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 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.

[0044] In some aspects, 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 someaspects, the first, second, and third temperatures are different. In some aspects, the first, second, and third temperatures are the same.

[0045] In some aspects, 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. In some aspects, 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. In some aspects, 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 increments with subsequent repetitions.

[0046] In some aspects, 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. In some aspects, the chamber is purged with N2, CO2, or another inert gas before use to prevent oxidation and / or degradation of the desired compounds.

[0047] With reference to FIG 4, in some aspects, provided is another example method of 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. In some aspects, 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 10'2torr, or below about 10'6torr, or below about 10'10torr. 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. In some aspects, microwaves or ultrasonic waves can be applied to the trichomes 108 during the applying negative pressure step to facilitate volatilization.

[0048] In the first cold trap, a portion of the gaseous plant extract 114 is condensed 416a at a first temperature below about 25 °C into a first liquid plant extract 418b. In the second cold trap, 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. In the third cold trap, 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. In the fourth cold trap, 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. In the fifth cold trap, 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.

[0049] In some aspects, 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 -200°C. In some aspects, 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. In some aspects, 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.

[0050] Each of the condensation steps 416a, 416b, 416c, 416d, and 416e collectively define a method of fractional condensation 420. In some aspects, 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.

[0051] In the example methods 103’ and 103”, each of the desired compounds is a terpene, a terpenoid, a cannabinoid, or a flavonoid. In some aspects, the plant is cannabis and the trichomes are resin glands. In some aspects, the plant is hops and the trichomes are lupulin glands. In some aspects, the trichomes are from any other essence or essential oil producing plant or any organism that produces trichomes that contain a desirable chemical compound. Insome aspects, 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- terpinene, a-terpineol, terpinolene, ylangene, cannabinol (CBN), cannabinolic acid (CBNA), DELTA (9)-tetrahydrocannabinol (DELTA (9)-THC), DELTA (9)-tetrahydrocannabinolic acid (DELTA (9)-THCA), DELTA (9)-cannabidiol (DELTA (9)-CBD), DELTA (9)- tetrahydrocannabidiolic acid (DELTA (9)-CBDA), DELTA (8)-tetrahydrocannabinol (DELTA (8)-THC), DELTA (8)-tetrahydrocannabinolic acid (DELTA (8)-THCA), DELTA (8)-tetrahydrocannabidiol (DELTA (8)-CBD), DELTA (8)-tetrahydrocannabidiolic acid (DELTA (8)-CBDA), DELTA (9)-tetrahydrocannabivarin (DELTA (9)-THV), cannabigerol (CBG), cannabigerolic acid (CBGA), cannabichromene (CBC), cannabichromenic acid (CBCA), cannabicyclol (CBL), cannabicyclolic acid (CBLA), cannabivarin (CBV), tetrahydrocannabivarin (THCV), cannabidivarin (CBDV), cannabichromevarin (CBCV), cannabigerovarin (CBGV), cannabigerol monomethyl ether (CBGM), beta-caryophyllene epoxide, mentha-l,8(9)-dien-5-ol, pulegone, limonene, limonene oxide, alpha-terpinene, terpinen-4-ol, carvacrol, carvone, 1,8-cineole, p-cymene, fenchone, pulegone- 1,2-epoxide, beta-myrcene, cannflavin A, or cannflavin B.

[0052] In another aspect, provided is a 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. In some aspects, the method produces multiple liquid plant extracts. In some extracts, the multiple liquid plant extracts are combined.

[0053] In some aspects, 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. In some aspects, the method of plant extraction via vacuum extraction requires less solvent than conventional extraction methods. In some aspects, the method of plant extraction via vacuum extraction can be performed on trichomes obtained by the method of harvesting trichomes. In some aspects, the method of plant extraction via vacuum extraction can be performed on trichomes obtained by conventional harvest methods. In some aspects, 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. In some aspects, the method of plant extraction via vacuum extraction can be performed as a sole extraction method. In some aspects, the method of plant extraction via vacuum extraction can be used in conjunction with another conventional plant extraction method (e.g., winterization).CAVITATION EXTRACTION OF TRICHOMES

[0054] With reference to FIG 5, in an aspect, provided is an example method of plant extraction via cavitation extraction 105’. The term “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.

[0055] A plurality of trichomes 108 from a plant are provided and combined 120 with a fluid 122 to form a mixture 124. In some aspects, the fluid is water, alcohol, glycerin, propane, butane, or a mixture thereof. Cavitation is then induced 126 in the mixture 124. In some aspects, the combining 120 and inducing cavitation 126 steps occur concurrently. In some aspects, 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.

[0056] In some aspects, 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. In some aspects, the stirred tank further includes a heat exchanger to control heat generated by the cavitation process.

[0057] In some aspects, 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.

[0058] Next, 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. In some aspects, 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. In some aspects,the separating step 128 includes a separation using only one apparatus. In some aspects, the separating step 128 includes a separation using an apparatus of increasing selectivity (e.g., increasingly smaller particle size).

[0059] In an aspect, a brine 502 can be added to the mixture 124 to facilitate separating out 128 the at least one desired compound 130. In some aspects, the brine solution includes sodium chloride, sodium sulfate, sodium phosphate, or another suitable ionic salt or combinations thereof. In some aspects, a brine is not added. In some aspects, 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. In some aspects, 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.

[0060] In some aspects, 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. In some aspects, all the depleted mixture 532 containing all of the recovered trichomes is recycled back into the mixture 124. In some aspects, 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). In some aspects, all the depleted mixture 532 is discarded.

[0061] In the example method 105’, each of the desired compounds is a terpene, a terpenoid, a cannabinoid, or a flavonoid. In some aspects, the plant is cannabis and the trichomes are resin glands. In some aspects, the plant is hops and the trichomes are lupulin glands. In some aspects, the trichomes are from any other essence or essential oil producing plant or any organism that produces trichomes that contain a desirable compound. In some aspects, 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(1 l)-diene, P-farnesene, 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- terpinene, a-terpineol, terpinolene, ylangene, cannabinol (CBN), cannabinolic acid (CBNA), DELTA (9)-tetrahydrocannabinol (DELTA (9)-THC), DELTA (9)-tetrahydrocannabinolicacid (DELTA (9)-THCA), DELTA (9)-cannabidiol (DELTA (9)-CBD), DELTA (9)- tetrahydrocannabidiolic acid (DELTA (9)-CBDA), DELTA (8)-tetrahydrocannabinol (DELTA (8)-THC), DELTA (8)-tetrahydrocannabinolic acid (DELTA (8)-THCA), DELTA (8)-tetrahydrocannabidiol (DELTA (8)-CBD), DELTA (8)-tetrahydrocannabidiolic acid (DELTA (8)-CBDA), DELTA (9)-tetrahydrocannabivarin (DELTA (9)-THV), cannabigerol (CBG), cannabigerolic acid (CBGA), cannabichromene (CBC), cannabichromenic acid (CBCA), cannabicyclol (CBL), cannabicyclolic acid (CBLA), cannabivarin (CBV), tetrahydrocannabivarin (THCV), cannabidivarin (CBDV), cannabichromevarin (CBCV), cannabigerovarin (CBGV), cannabigerol monomethyl ether (CBGM), beta-caryophyllene epoxide, mentha-l,8(9)-dien-5-ol, pulegone, limonene, limonene oxide, alpha-terpinene, terpinen-4-ol, carvacrol, carvone, 1,8-cineole, p-cymene, fenchone, pulegone- 1,2-epoxide, beta-myrcene, cannflavin A, or cannflavin B.

[0062] In another aspect, provided is a 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.

[0063] In some aspects, 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. In some aspects, the method of plant extraction via cavitation extraction requires less solvent than conventional extraction methods. In some aspects, the method of plant extraction via cavitation extraction can be performed on trichomes obtained by the method of harvesting trichomes. In some aspects, the method of plant extraction via cavitation extraction can be performed on trichomes obtained by conventional harvest methods. In some aspects, 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. In some aspects, the method of plant extraction via cavitation extraction can be performed as a sole extraction method. In some aspects, the method of plant extraction via cavitation extraction can be used in conjunction with another conventional plant extraction method (e.g., winterization).

[0064] Throughout the description and claims of this specification, the word “comprise” and other forms of the word, such as “comprising” and “comprises,” means including but not limited to, and are not intended to exclude, for example, other additives, segments, integers, orsteps. Furthermore, it is to be understood that the terms comprise, comprising, and comprises as they relate to various aspects, elements, and features of the disclosed invention also include the more limited aspects of “consisting essentially of’ and “consisting of.”

[0065] As used herein, the singular forms “a,” “an,” and “the” include plural referents unless the context clearly dictates otherwise. Thus, for example, reference to a “plant” includes aspects having two or more such plants unless the context clearly indicates otherwise.

[0066] 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.

[0067] As used herein, the terms “optional” or “optionally” mean that the subsequently described event or circumstance may or may not occur, and that the description includes instances where said event or circumstance occurs and instances where it does not.

[0068] For the terms “for example” and “such as,” and grammatical equivalences thereof, the phrase “and without limitation” is understood to follow unless explicitly stated otherwise.

[0069] All publications, patents, and patent documents cited herein are incorporated by reference as though individually incorporated by reference. No limitations inconsistent with this disclosure are to be understood therefrom. The invention has been described with reference to various specific and preferred embodiments and techniques. However, variations and modifications may be made while remaining within the spirit and scope of the invention.

[0070] While specific embodiments have been described above with reference to the disclosed embodiments and examples, such embodiments are only illustrative and do not limit the scope of the invention. Changes and modifications can be made in accordance with ordinary skill in the art without departing from the invention in its broader aspects as defined in the following claims.

Claims

What is claimed is:

1. A method of plant extraction, the method comprising: 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 terpenoid, a cannabinoid, or a flavonoid.

2. The method of claim 1, wherein the plant is cannabis and the trichomes are resin glands.

3. The method of claim 1, wherein the plant is hops and the trichomes are lupulin glands.

4. The method of claim 1, wherein the fluid is water, alcohol, glycerin, propane, butane, or a mixture thereof.

5. The method of claim 1, wherein step c is performed using a stirred tank having a rotor, wherein the rotor has a design that induces the cavitation when the rotor is spun.

6. The method of claim 1, wherein step d is executed using a centrifugal particle separator, a membrane filter, and / or a ceramic filtration apparatus.

7. The method of claim 1, wherein step d further comprises recovering the trichomes and recycling the trichomes back into the mixture in step b to further release any remaining desired compound according to step c and step d.

8. The method of claim 1, wherein step a further comprises separating the trichomes from unwanted contaminants or debris via a static electricity process.

9. A method of plant extraction, the method comprising:a) providing a plurality of trichomes from a plant at a first temperature below about35 °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 terpenoid, a cannabinoid, or a flavonoid.

10. The method of claim 9, wherein the plant is cannabis and the trichomes are resin glands.

11. The method of claim 9, wherein the plant is hops and the trichomes are lupulin glands.

12. The method of claim 9, further comprising repeating step b and step c to form multiple liquid plant extracts; wherein the negative pressure is lowered in each repetition; and wherein each liquid plant extract has a different chemical composition.

13. The method of claim 12, wherein step b and step c are repeated twice.

14. The method of claim 9, wherein: step b and step c are 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.

15. The method of claim 14, further comprising multiple cold traps operably coupled to the conduit; wherein each cold trap operates at a subsequently lower temperature to condense the gaseous plant extract to form multiple liquid plant extracts; and wherein each liquid plant extract has a different chemical composition.

16. The method of claim 9, wherein 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, exofenchol, 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-terpinene, a-terpineol, terpinolene, ylangene, cannabinol (CBN), cannabinolic acid (CBNA), DELTA (9)-tetrahydrocannabinol (DELTA (9)-THC), DELTA (9)-tetrahydrocannabinolic acid (DELTA (9)-THCA), DELTA (9)-cannabidiol (DELTA (9)-CBD), DELTA (9)-tetrahydrocannabidiolic acid (DELTA (9)- CBDA), DELTA (8)-tetrahydrocannabinol (DELTA (8)-THC), DELTA (8)- tetrahydrocannabinolic acid (DELTA (8)-THCA), DELTA (8)-tetrahydrocannabidiol (DELTA (8)-CBD), DELTA (8)-tetrahydrocannabidiolic acid (DELTA (8)-CBDA), DELTA (9)-tetrahydrocannabivarin (DELTA (9)-THV), cannabigerol (CBG), cannabigerolic acid (CBGA), cannabichromene (CBC), cannabichromenic acid (CBCA), cannabicyclol (CBL), cannabicyclolic acid (CBLA), cannabivarin (CBV), tetrahydrocannabivarin (THCV), cannabidivarin (CBDV), cannabichromevarin (CBCV), cannabigerovarin (CBGV), cannabigerol monomethyl ether (CBGM), beta-caryophyllene epoxide, mentha-l,8(9)-dien-5- ol, pulegone, limonene, limonene oxide, alpha-terpinene, terpinen-4-ol, carvacrol, carvone, 1,8-cineole, p-cymene, fenchone, pulegone- 1,2-epoxide, beta-myrcene, cannflavin A, or cannflavin B.

17. The method of claim 9, wherein step a further comprises separating the trichomes from unwanted contaminants or debris via a static electricity process.

18. A liquid plant extract prepared from the method of claim 9, comprising a greater quantity of at least one mono terpene than a control liquid plant extract prepared from a conventional method.

19. A method of plant extraction, the method comprising a) providing a wet plant material comprising 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 terpene, a terpenoid, a cannabinoid, or a flavonoid.

20. The method of claim 19, wherein step b is performed using liquid nitrogen to reach the first temperature.

21. The method of claim 19, wherein step a further comprises: i) discarding fan leaves and leaves without trichomes; ii) separating out branches; and / or iii) bucking the branches to remove buds; wherein only the buds undergo step b and step c.

22. The method of claim 19, wherein 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, exofenchol, 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-terpinene, a-terpineol, terpinolene, ylangene, cannabinol (CBN), cannabinolic acid (CBNA), DELTA (9)-tetrahydrocannabinol (DELTA (9)-THC), DELTA (9)-tetrahydrocannabinolic acid (DELTA (9)-THCA), DELTA (9)-cannabidiol (DELTA (9)-CBD), DELTA (9)-tetrahydrocannabidiolic acid (DELTA (9)- CBDA), DELTA (8)-tetrahydrocannabinol (DELTA (8)-THC), DELTA (8)- tetrahydrocannabinolic acid (DELTA (8)-THCA), DELTA (8)-tetrahydrocannabidiol (DELTA (8)-CBD), DELTA (8)-tetrahydrocannabidiolic acid (DELTA (8)-CBDA), DELTA (9)-tetrahydrocannabivarin (DELTA (9)-THV), cannabigerol (CBG), cannabigerolic acid(CBGA), cannabichromene (CBC), cannabichromenic acid (CBCA), cannabicyclol (CBL), cannabicyclolic acid (CBLA), cannabivarin (CBV), tetrahydrocannabivarin (THCV), cannabidivarin (CBDV), cannabichromevarin (CBCV), cannabigerovarin (CBGV), cannabigerol monomethyl ether (CBGM), beta-caryophyllene epoxide, mentha-l,8(9)-dien-5- ol, pulegone, limonene, limonene oxide, alpha-terpinene, terpinen-4-ol, carvacrol, carvone, 1,8-cineole, p-cymene, fenchone, pulegone- 1,2-epoxide, beta-myrcene, cannflavin A, or cannflavin B.

23. The method of claim 19, wherein step a further comprises separating the trichomes from unwanted contaminants or debris via a static electricity process.

24. A liquid plant extract prepared from the method of claim 19, comprising a greater quantity of at least one mono terpene than a control liquid plant extract prepared from a conventional method.

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