SYSTEMS AND METHODS FOR EXTRACTING MATERIALS

CROSS-REFERENCE

[001] This application claims priority to U.S. Provisional Application Number

63/192,861 filed May 25, 2021, which is incorporated herein by reference in its entirety.

BACKGROUND

[002] The cannabis industry is expanding in several parts of the world where it has been legalized for either recreational or medical use. For that matter, industrials are trying to create new products in order to develop their economical market. The recent legalization of cannabis and the development of this industry have led to the development of new extraction processes in order to make quality products in agreement with standards established by local governments.

[003] Cannabis extracted from cannabis flower embodies new opportunities and safer ways to consume cannabis. For that matter, in the solvent extraction field, the choice of solvent is important in regards of the final product consistency and purity. Thus there is a need for new methods of obtaining extracts from cannabis flowers.

SUMMARY

[004] Provided herein, in part, are methods of extracting an oil comprising a plurality of cannabinoids or terpenoids, or a combination thereof, from a feedstock comprising a plant of the genus Cannabis , oils comprising a plurality of cannabinoids or terpenoids, and compositions comprising a feedstock comprising a plant of the genus Cannabis admixed with a hydrocarbon blend.

[005] Thus, in an aspect provided herein is a method of extracting an oil comprising a plurality of cannabinoids or terpenoids, or a combination thereof, from a feedstock comprising a plant of the genus Cannabis , the method comprising: i) contacting the feedstock with a hydrocarbon blend consisting essentially of a first hydrocarbon, a second hydrocarbon, and a third hydrocarbon at a temperature at or below -50°C to provide a hydrocarbon-based mixture; ii) isolating the hydrocarbon-based mixture from the feedstock; and iii) removing the hydrocarbon blend from the hydrocarbon -based mixture thereby obtaining the oil. [006] In an aspect, provided herein is a method of extracting an oil comprising a plurality of cannabinoids or terpenoids, or a combination thereof, from a feedstock comprising a plant of the genus Cannabis , the method comprising: i) contacting the feedstock with a hydrocarbon blend consisting essentially of a first hydrocarbon, a second hydrocarbon, and a third hydrocarbon at a temperature at or below -60°C to provide a hydrocarbon-based mixture; ii) isolating the hydrocarbon-based mixture from the feedstock; and iii) removing the hydrocarbon blend from the hydrocarbon -based mixture thereby obtaining the oil.

[007] In some embodiments, the first hydrocarbon is n-butane.

[008] In some embodiments, the second hydrocarbon is propane.

[009] In some embodiments, the third hydrocarbon is isobutane.

[0010] In some embodiments, the n-butane is present in the hydrocarbon blend in an amount of about 50 weight % to about 90 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the n-butane is present in the hydrocarbon blend in an amount of about 80 weight % to about 90 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the n-butane is present in the hydrocarbon blend in an amount of about 85 weight % based on the total weight of the hydrocarbon blend.

[0011] In some embodiments, the propane is present in the hydrocarbon blend in an amount of about 5 weight % to about 25 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the propane is present in the hydrocarbon blend in an amount of about 5 weight % to about 15 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the propane is present in the hydrocarbon blend in an amount of about 10 weight % based on the total weight of the hydrocarbon blend.

[0012] In some embodiments, the isobutane is present in the hydrocarbon blend in an amount of about 1 weight % to about 15 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the isobutane is present in the hydrocarbon blend in an amount of about 1 weight % to about 10% weight % based on the total weight of the hydrocarbon blend. In some embodiments, the isobutane is present in the hydrocarbon blend in an amount of about 5 weight % based on the total weight of the hydrocarbon blend. [0013] In some embodiments, the plant of the genus Cannabis is Cannabis sativa or

Cannabis indica.

[0014] In some embodiments, the feedstock is a fresh frozen feedstock.

[0015] In some embodiments, the plurality of terpenoids comprises one or more terpenoids selected from the group consisting of alpha thujene, alpha pinene, camphene, beta pinene, beta myrcene, p-mentha- 1,5-diene, 3-carene, alpha terpinene, p-cymene, D-limonene, beta ocimene, terpinolene, linalool, fenchol, trans-2-pinanol, alpha terpineol, beta caryophyllene, gamma elemene, alpha bergamotene, humulene, caryophyllene oxide, 4,8,12- Tetradecatrienal, beta selinene, alpha selinene, alpha bulnesene, alpha farnesene, beta maaliene, (4aR,8aS)-4a-Methyl-l-methylene-7-(propan-2-ylidene)decahydr onaphthalene, cis nerolidol, trans nerolidol, Selina-3, 7(1 l)-diene, trans alpha bisabolene, beta guaiene, epi- gamma-eudesmol, longifolene, cis beta guaiene, aromandendrene, alpha eudesmol, alpha bulnesene, alpha bisabolol, juniper camphor, and beta bisabolene.

[0016] In some embodiments, the plurality of cannabinoids comprises one or more cannabinoids selected from the group consisting of tetrahydrocannabinol, cannabigerol, cannabichromene, tetrahydrocannabivarin, cannabidiol, cannabinol, cannabigerivarin, tetrahydrocannabivarian, cannabidivarin, cannabichromevarin, and carboxylic acid derivatives thereof.

[0017] In some embodiments, the contacting step is carried out a temperature from about -68 to -72°C.

[0018] In some embodiments, the temperature is about -70 °C.

[0019] In some embodiments, the oil is characterized by a color that is substantially the same as depicted in FIG. 1.

[0020] In some embodiments, the method extracts at least 100 g of terpenoids per 4.5 kg of the feedstock. In some embodiments, the method extracts at least 15 g of cannabinoids per 4.5 kg of the feedstock. In some embodiments, the method extracts at least 40 g of cannabinoids per 4.5 kg of the feedstock.

[0021] In another aspect, provided herein is an oil comprising a plurality of cannabinoids or terpenoids, or a combination thereof, obtained by: i) contacting a feedstock comprising a plant of the genus Cannabis with a hydrocarbon blend consisting essentially of a first hydrocarbon, a second hydrocarbon, and a third hydrocarbon at a temperature at or below -60°C to provide a hydrocarbon-based mixture; ii) isolating the hydrocarbon-based mixture from the feedstock; and iii) removing the hydrocarbon blend from the hydrocarbon- based mixture to produce the oil.

[0022] In some embodiments, the first hydrocarbon is n-butane.

[0023] In some embodiments, the second hydrocarbon is propane.

[0024] In some embodiments, the third hydrocarbon is isobutane.

[0025] In some embodiments, the n-butane is present in the hydrocarbon blend in an amount of about 50 weight % to about 90 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the n-butane is present in the hydrocarbon blend in an amount of about 80 weight % to about 90 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the n-butane is present in the hydrocarbon blend in an amount of about 85 weight % based on the total weight of the hydrocarbon blend.

[0026] In some embodiments, the propane is present in the hydrocarbon blend in an amount of about 5 weight % to about 25 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the propane is present in the hydrocarbon blend in an amount of about 5 weight % to about 15 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the propane is present in the hydrocarbon blend in an amount of about 10 weight % based on the total weight of the hydrocarbon blend.

[0027] In some embodiments, the isobutane is present in the hydrocarbon blend in an amount of about 1 weight % to about 15 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the isobutane is present in the hydrocarbon blend in an amount of about 1 weight % to about 10% weight % based on the total weight of the hydrocarbon blend. In some embodiments, the isobutane is present in the hydrocarbon blend in an amount of about 5 weight % based on the total weight of the hydrocarbon blend.

[0028] In some embodiments, the plant of the genus Cannabis is Cannabis sativa or

Cannabis indica.

[0029] In some embodiments, the feedstock is a fresh frozen feedstock. [0030] In some embodiments, the oil is characterized by a higher concentration of terpenes and/or cannabinoids relative to an oil produced by: i) contacting a feedstock comprising a plant of the genus Cannabis with a hydrocarbon mixture essentially consisting of n-butane and propane in about 7:3 weight ratio at a temperature at or below -50°C to provide a hydrocarbon-based blend; ii) isolating the hydrocarbon-based blend from the feedstock; and iii) removing the hydrocarbon mixture from the hydrocarbon-based blend to produce the oil.

[0031] In some embodiments, the oil is characterized by a higher concentration of terpenes and/or cannabinoids relative to an oil produced by: i) contacting a feedstock comprising a plant of the genus Cannabis with a hydrocarbon mixture essentially consisting of n-butane and propane in about 7:3 weight ratio at a temperature at or below -60°C to provide a hydrocarbon-based blend; ii) isolating the hydrocarbon-based blend from the feedstock; and iii) removing the hydrocarbon mixture from the hydrocarbon-based blend to produce the oil.

[0032] In some embodiments, the oil is characterized as having substantially less color relative to an oil produced by: i) contacting a feedstock comprising a plant of the genus Cannabis with a hydrocarbon mixture essentially consisting of n-butane and propane in about 7:3 weight ratio at a temperature at or below -60°C to provide a hydrocarbon-based blend; ii) isolating the hydrocarbon-based blend from the feedstock; and iii) removing the hydrocarbon mixture from the hydrocarbon-based blend to produce the oil.

[0033] In another aspect, provided herein is a composition comprising a feedstock comprising a plant of the genus Cannabis admixed with a hydrocarbon blend consisting essentially of n-butane, propane, and isobutane.

[0034] In some embodiments, the n-butane is present in the hydrocarbon blend in an amount of about 50 weight % to about 90 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the n-butane is present in the hydrocarbon blend in an amount of about 80 weight % to about 90 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the n-butane is present in the hydrocarbon blend in an amount of about 85 weight % based on the total weight of the hydrocarbon blend.

[0035] In some embodiments, the propane is present in the hydrocarbon blend in an amount of about 5 weight % to about 25 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the propane is present in the hydrocarbon blend in an amount of about 5 weight % to about 15 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the propane is present in the hydrocarbon blend in an amount of about 10 weight % based on the total weight of the hydrocarbon blend.

[0036] In some embodiments, the isobutane is present in the hydrocarbon blend in an amount of about 1 weight % to about 15 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the isobutane is present in the hydrocarbon blend in an amount of about 1 weight % to about 10% weight % based on the total weight of the hydrocarbon blend. In some embodiments, the isobutane is present in the hydrocarbon blend in an amount of about 5 weight % based on the total weight of the hydrocarbon blend.

[0037] In some embodiments, the plant of the genus Cannabis is Cannabis sativa or

Cannabis indica.

[0038] In some embodiments, the feedstock is a fresh frozen feedstock.

BRIEF DESCRIPTION OF THE DRAWINGS

[0039] These and other features of the present disclosure will become more apparent in the following detailed description in which reference is made to the appended drawings. The appended drawings illustrate one or more embodiments of the present disclosure by way of example only and are not to be construed as limiting the scope of the present disclosure. [0040] The patent or application file contains at least one drawing executed in color.

Copies of this patent or patent application publication with color drawing(s) will be provided by the Office upon request and payment of the necessary fee.

[0041] FIG. 1 shows an exemplary grading system of color. Darker color (toward 1) is characterized by dark brown, red/orange, or dark orange color. Lighter color (toward 10) is characterized by gold, light yellow, or opaque yellow.

DETAILED DESCRIPTION

[0042] The following description is provided to enable any person skilled in the art to make and use the contents of this disclosure and sets forth the best modes contemplated by the inventors. Various modifications, however, will remain readily apparent to those skilled in the art, since the general principles of the present disclosure have been defined herein specifically to provide strain specific cannabis extracts. It will be understood that that the processes described herein have been contemplated to work with all plant cultivars of the genus Cannabis regardless of whether the particular cultivar is called "hemp," "sativa," "indica" or any other variety, species or subspecies of Cannabis.

Definitions

[0043] As used herein, the term "cannabinoid " refers to: (i) a chemical compound belonging to a class of secondary compounds commonly found in plants of genus Cannabis , (ii) synthetic cannabinoids and any enantiomers thereof; and/or (iii) one of a class of diverse chemical compounds that may act on cannabinoid receptors such as CB1 and CB2.

[0044] Any and all isomeric, enantiomeric, or optically active derivatives are also encompassed. In particular, where appropriate, reference to a particular cannabinoid includes both the "A Form" and the "B Form". For example, it is known that THCA has two isomers, THCA-A in which the carboxylic acid group is in the 1 position between the hydroxyl group and the carbon chain (A Form) and THCA-B in which the carboxylic acid group is in the 3 position following the carbon chain (B Form). As will be appreciated by those skilled in the art who have benefited from the teachings of the present disclosure, "cannabinoid" may refer to: salts of acid forms, such as Na ⁺ or Ca ²⁺ salts of such acid forms; and/or ester forms, such as formed by hydroxyl-group esterification to form traditional esters, sulphonate esters, and/or phosphate esters.

[0045] Cannabinoids include tetrahydrocannabinolic acid, tetrahydrocannabinol, cannabigerol, cannabichromene, tetrahydrocannabivarin, cannabidiol, cannabinol, cannabigerivarin, tetrahydrocannabivarian, cannabidivarin, cannabichromevarin, and derivatives thereof. Examples of cannabinoids include, but are not limited to, Cannabigerolic Acid, (CBGA), Cannabigerolic Acid Monomethylether (CBGAM), Cannabigerol (CBG), Cannabigerol Monomethylether (CBGM), Cannabigerovarinic Acid (CBGVA), Cannabigerovarin (CBGV), Cannabichromenic Acid (CBCA), Cannabichromene (CBC), Cannabichromevarinic Acid (CBCVA), Cannabichromevarin (CBCV), Cannabidiolic Acid (CBDA), Cannabidiol (CBD), A6-Cannabidiol (DQ-CBD), Cannabidiol Monomethylether (CBDM), Cannabidiol-C4 (CBD-C4), Cannabidivarinic Acid (CBDVA), Cannabidivarin (CBDV), Cannabidiorcol (CBD-C1), Tetrahydrocannabinolic Acid (e.g., Tetrahydrocannabinolic Acid A (THCA-A), Tetrahydrocannabinolic Acid B (THCA-B)), Tetrahydrocannabinol (THC or DQ-THC), Dd-tetrahydrocannabinoi (Dd-THC), trans- A 10- tetrahydrocannabinol (trans-AlO-THC), cis-Al 0-tetrahydrocannabinol (cis-AlO-THC), Tetrahydrocannabinolic Acid C4 (THCA-C4), Tetrahydrocannabinol C4 (THC-C4), Tetrahydrocannabivarinic Acid (THCVA), Tetrahydrocannabivarin (THCV), Dd- Tetrahydrocannabivarin (Dd-THCV), A9-Tetrahydrocannabivarin (A9-THCV), Tetrahydrocannabiorcolic Acid (THCA-Cl), Tetrahydrocannabiorcol (THC-C1), A7-cis-iso- tetrahydrocannabivarin, Dd-Tetrahydrocannabinolic Acid (Dd-THCA), A9- Tetrahydrocannabinolic Acid (DQ-THCA), CannabicycloJic Acid (CB1_A), Cannabicycloi (CBL), Cannabicyclovarin (CBLV), Cannabielsoic Acid A (CBEA-A), Cannabielsoic Acid B (CBEA-B), Cannabielsoin (CBE), Cannabinoiic Acid (CBNA), Cannabinol (CBN), Cannabinol Methylether (CBNM), Cannabinol-C4 (CBN-C4), Cannabivarin (CBV), Cannabino-C2 (CBN-C2), Cannabiorcol (CBN-C1), Cannabinodiol (CBND), Cannabinodivarin (CBDV), Cannabitriol (CBT), ll-hydroxy-A9-tetrahydrocannabinol (1 1- OH-THC), 11 nor 9-carboxy-A9-tetrahydrocannabinol, Ethoxy-cannabitriolvarin (CBTVE), 10-Ethoxy-9-hydroxy-A6a-tetrahydrocannabinol, Cannabitriolvarin (CBTV), 8,9 Dihydroxy - A6a(10a)-tetrahydrocannabinol (8,9-Di-OH-CBT-C5), Dehydrocannabifuran (DCBF), Cannbifuran (CBF), Cannabichromanon (CBCN), Cannabicitran, 10-Oxo-A6a(10a)- tetrahydrocannabinol (OTHC), A9-cis-tetrahydrocannabinol (cis-THC), Cannabiripsol (CBR), 3,4,5,6-tetrahydro-7-hydroxy-alpha-alpha-2-trimethyl-9-n-pro pyl-2,6-methano-2H-l- benzoxocin-5 -methanol (OH-iso-HHC V), Trihydroxy-delta -9-tetrahydrocannabinol (triOH- THC), Yangonin, Epigallocatechin gall ate, Dodeca-2E, 4E, 8Z, lOZ-tetraenoic acid isobutyl amide, hexahydrocannibinol, and Dodeca-2E,4E-dienoic acid isobutyl amide.

[0046] As used herein and unless otherwise specified, the term "terpenoid" may refer to either a "terpene compound" or "terpenoid-type compound." "Terpene compound" refers to isoprene-containing hydrocarbons, having isoprene units (CH ₂ C(CH ₃ )CHCH ₂ ) in a head- to-tail orientation. Terpene compounds in general, have the molecular formula (C ₅ H ₈ ) _n , and include hemiterpenes, (C5), monoterpenes (C10), sesquiterpenes (Cl 5), diterpenes (C20), triterpenes (C30), and tetraterpenes (C40) which respectively have 1, 2, 3, 4, 6 and 8 isoprene units. Terpene compounds may be further classified as acyclic or cyclic. "Terpenoid-type compound" refers to a terpene-related compound, which contains at least one oxygen atom in addition to isoprene units, and thus includes alcohols, aldehydes, ketones, ethers, such as but not limited to, carboxylic acids derivatives thereof, such as esters. Terpenoid-type compounds are subdivided according to the number of carbon atoms in a manner similar to terpene and thus include hemiterpenoids, (C5), monoterpenoid-type compounds (CIO), sesquiterpenoid-type (C15), diterpenoid-type (C20), triterpenoid-type (C30), and tetraterpenoid-type compounds (C40) which respectively have 1, 2, 3, 4, 6 and 8 isoprene units. The skeleton of terpenoid-type compounds may differ from strict additivity of isoprene units by the loss or shift of a fragment, commonly a methyl group. Examples of monoterpenoid-type compounds include camphor, eugenol, menthol and bomeol. Examples of diterpenoid-type compounds include phytol, retinol and taxol. Examples of triterpenoid- type compounds include betulinic acid and lanosterol. Terpenoid-type compounds may be acyclic or may contain one or more ring-structures. Triterpenoid-type compounds may be acyclic or may contain one or more ring-structures. The rings may contain only carbon atoms, or alternatively may contain one or more oxygen atoms besides carbon atoms. Common ring-sizes range from three-membered rings to ten-membered rings. Larger ring sizes of up to at least twenty -membered rings are possible. More than one ring and more than one ring-size maybe present in a single tri terpenoid-type compounds. In case a triterpenoid- type compound contains more than one ring, the rings may be present and separated by one or more acyclic bonds; alternatively, the rings may be directly connected via connections of the annealed type, the bridged type, the spiro-type or combinations of any of these types. Multiply annealed, fused, bridged, or spiro-type ring systems are possible. Combinations of singly and multiply annealed, bridged, fused, spiro-type rings are possible. Combinations of isolated rings and connected rings in the same triterpenoid-type are possible, Exemplary terpenoids include, but are not limited to alpha thujene, alpha pinene, camphene, beta pinene, beta myrcene, p-mentha- 1,5-diene, 3-carene, alpha terpinene, p-cymene, D-limonene, beta ocimene, terpinolene, linalool, fenchol, trans-2-pinanol, alpha terpineol, beta caryophyllene, gamma elemene, alpha bergamotene, humulene, caryophyllene oxide, 4,8,12- Tetradecatrienal, beta selinene, alpha selinene, alpha bulnesene, alpha famesene, beta maaliene, (4aR,8aS)-4a-Methyl-l-methylene-7-(propan-2-ylidene)decahydr onaphthalene, cis nerolidol, trans nerolidol, Selina-3, 7(1 l)-diene, trans alpha bisabolene, beta guaiene, epi- gamma-eudesmol, longifolene, cis beta guaiene, aromandendrene, alpha eudesmol, alpha bulnesene, alpha bisabolol, juniper camphor, and beta bisabolene.

[0047] As used herein, "plurality of terpenoids" refers to a mixture of one or more terpenoids. As used herein, "plurality of cannabinoids" refers to a mixture of more than one cannabinoid.

[0048] As used herein, the term "about" denotes an approximate range of plus or minus 10% from a specified value. For instance, the language "about 20%" encompasses a range of 18-22%. As used herein, "about" also includes the exact amount. Hence "about 20%" means "about 20% " and also "20%. " Methods of Extraction

[0049] The present disclosure describes, in part, methods of extracting a composition

(e.g., an oil) comprising a plurality of cannabinoids or terpenoids, or a combination thereof, from a feedstock comprising a plant of the genus Cannabis.

[0050] In some embodiments, the feedstock comprising a plant of the genus Cannabis is produced by harvesting a plant material (e.g., plant of the genus Cannabis) and rapidly freezing it to protect the volatile terpenoids many of which are lost during the usual drying/curing of cannabis material. Then the frozen cannabis is pulverized to form the feedstock.

[0051] Harvesting the Plant Material. The majority of cannabis extracts are produced by extracting cannabis material that is grown, harvested and stored according to the "traditional" methods. Growing cannabis is beyond the scope of the current disclosure; although the precise cultural conditions will undoubtedly influence the quantity and quality of various natural products ultimately extracted from the plant material. Traditionally, cannabis material is harvested when the inflorescence is at the peak level of trichome production. This normally occurs when or shortly after the stigmas have reached peak maturity and have started to deteriorate. The plants (or only the inflorescences) are harvested and allowed to dry under controlled conditions. Often the material is allowed to dry at somewhat elevated temperature and reduced humidity to speed the dehydration process and to accelerate the decarboxylation of cannabinoid acids into active cannabinoids. Unfortunately, during the collection and drying process significant quantities of volatile terpenoids are lost to the atmosphere. As in wine, cannabis strains have distinctive fragrances such as piney, or fruity, "berry -like", or even "banana-like" when fresh. They may well lose these distinctive characteristics during the collection and drying process. This process eschews the traditional drying process. Instead the freshly harvested plant material is rapidly frozen at cryogenic temperatures immediately following harvest and stored in a frozen state to preserve the original terpenoid profile of the individual strain.

[0052] Extraction. The methods of extracting described herein comprise contacting the feedstock with a solvent. In some embodiments, the solvent has a polarity index range of 0.0 to 5.0, 0.0 to 4.0, 0.0 to 3.0, 0.0 to 2.0, or 0.0 to 1.0. For example, the solvent has a polarity index of 0.0, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0,9, or 1.0. In some embodiments, the solvent has a dielectric constant of 1.5 to 20.0, 1.5 to 15.0, 1.5 to 10.0, 1.5 to 5.0, or 1.5 to 2,0. For example, the solvent has a dielectric constant of about 1.5, 1.6, 1.7, 1 .8, 1 .9, 2,0, 2.1, 2,2, 2,3, 2,4, or 2,5. In some embodiments, the solvent has a boiling point of about 25 °C to about 100 °C, e.g., about 25 °C to about 80 °C, about 25 °C to about 60 °C, about 25 °C to about 40 °C, about 30 °C to about 60 °C, or about 30 °C to 40 °C. Exemplary solvents include, but are not limited to, pentane, hexane, heptane, isopentane, isobutane, methanol, ethanol, isopropano!, dimethyl sulfoxide, acetone, ethyl acetate, diethyl ether, tert-butyl methyl ether, water, acetic acid, anisole, 1 -butanol, 2-butanol, butane, butyl acetate, ethyl formate, formic acid, isobutyl acetate, isopropyl acetate, methyl acetate, 3 -methyl- 1 -butanol, methylethyl ketone, 2-methyl- i -propanol , 1-pentanol, 1-propanol, propane, propyl acetate, trimethylamine, or a combination thereof. In some embodiments, the solvent is n-butane, propane, or isobutane, or a combination thereof.

[0053] In some embodiments, the solvent is a hydrocarbon or a hydrocarbon blend.

For example, the hydrocarbon blend comprises a first hydrocarbon, a second hydrocarbon, and a third hydrocarbon. In some embodiments, the hydrocarbon consists essentially of a first hydrocarbon, a second hydrocarbon, and a third hydrocarbon.

[0054] In some embodiments, the first hydrocarbon is n-butane.

[0055] In some embodiments, the second hydrocarbon is propane.

[0056] In some embodiments, the third hydrocarbon is isobutane.

[0057] In some embodiments, the n-butane is present in the hydrocarbon blend in an amount of about 50 weight % to about 90 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the n-butane is present in the hydrocarbon blend in an amount of about 80 weight % to about 90 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the n-butane is present in the hydrocarbon blend in an amount of about 85 weight % based on the total weight of the hydrocarbon blend.

[0058] In some embodiments, the propane is present in the hydrocarbon blend in an amount of about 5 weight % to about 25 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the propane is present in the hydrocarbon blend in an amount of about 5 weight % to about 15 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the propane is present in the hydrocarbon blend in an amount of about 10 weight % based on the total weight of the hydrocarbon blend. [0059] In some embodiments, the isobutane is present in the hydrocarbon blend in an amount of about 1 weight % to about 15 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the isobutane is present in the hydrocarbon blend in an amount of about 1 weight % to about 10% weight % based on the total weight of the hydrocarbon blend. In some embodiments, the isobutane is present in the hydrocarbon blend in an amount of about 5 weight % based on the total weight of the hydrocarbon blend.

[0060] In some embodiments, the method results in obtaining at least 1 g of cannabinoids per 4.5 kg of the feedstock, at least 5 g of cannabinoids per 4.5 kg of the feedstock, at least at least 10 g of cannabinoids per 4.5 kg of the feedstock, at least 15 g of cannabinoids per 4.5 kg of the feedstock, at least 20 g of cannabinoids per 4.5 kg of the feedstock, at least 25 g of cannabinoids per 4.5 kg of the feedstock, at least 30 g of cannabinoids per 4.5 kg of the feedstock, at least 35 g of cannabinoids per 4.5 kg of the feedstock, at least 40 g of cannabinoids per 4.5 kg of the feedstock, at least 45 g of cannabinoids per 4.5 kg of the feedstock, at least 50 g of cannabinoids per 4.5 kg of the feedstock, or at least 100 g of cannabinoids per 4.5 kg of the feedstock. In some embodiments, the method extracts at least 100 g of terpenoids per 4.5 kg of the feedstock. In some embodiments, the method extracts at least 15 g of cannabinoids per 4.5 kg of the feedstock. In some embodiments, the method extracts at least 40 g of cannabinoids per 4.5 kg of the feedstock.

[0061] In some embodiments, of the genus Cannabis is Cannabis sativa, Cannabis indica , or Cannabis ruderalis. In some embodiments, the plant of the genus Cannabis is Cannabis sativa or Cannabis indica.

[0062] In some embodiments, the feedstock is a fresh frozen feedstock.

[0063] In some embodiments, the plurality of terpenoids comprises one or more terpenoids selected from the group consisting of alpha thujene, alpha pinene, camphene, beta pinene, beta myrcene, p-mentha- 1,5-diene, 3-carene, alpha terpinene, p-cymene, D-limonene, beta ocimene, terpinolene, linalool, fenchol, trans-2-pinanol, alpha terpineol, beta caryophyllene, gamma elemene, alpha bergamotene, humulene, caryophyllene oxide, 4,8,12- Tetradecatrienal, beta selinene, alpha selinene, alpha bulnesene, alpha famesene, beta maaliene, (4aR,8aS)-4a-Methyl-l-methylene-7-(propan-2-ylidene)decahydr onaphthalene, cis nerolidol, trans nerolidol, Selina-3, 7(1 l)-diene, trans alpha bisabolene, beta guaiene, epi- gamma-eudesmol, longifolene, cis beta guaiene, aromandendrene, alpha eudesmol, alpha bulnesene, alpha bisabolol, juniper camphor, and beta bisabolene.

[0064] In some embodiments, the plurality of cannabinoids comprises one or more cannabinoids selected from the group consisting of tetrahydrocannabinol, cannabigerol, cannabichromene, tetrahydrocannabivarin, cannabidiol, cannabinol, cannabigerivarin, tetrahydrocannabivarian, cannabidivarin, cannabichromevarin, and carboxylic acid derivatives thereof.

[0065] In some embodiments, the contacting step is carried out a temperature from about -68 to -72°C.

[0066] In some embodiments, the temperature is about -70 °C. In some embodiments, the temperature is about -80 °C. In some embodiments, the temperature is about -60 °C to about -80 °C. In some embodiments, the temperature is about -65 °C to about -80 °C.

[0067] In some embodiments, the oil comprises a total cannabinoid content of about 60% to about 90% by weight based on the weight of the oil. In some embodiments, the oil comprises a total terpenoid content of about 5% to about 15% by weight based on the weight of the oil. In some embodiments, the oil is characterized by an L* value of at least 30 (e.g., at least 35, e.g., about 35 to about 40) or an a* value less than 9 in the CIELAB color space. In some embodiments, the oil is characterized by an L* value of at least 30 (e.g., at least 35, e.g., about 35 to about 40) and an a* value less than 9 in the CIELAB color space.

[0068] In some embodiments, the oil is characterized by a color that is substantially the same as depicted in FIG. 1.

Compositions

[0069] In another aspect, provided herein is an oil comprising a plurality of cannabinoids or terpenoids, or a combination thereof, obtained by: i) contacting a feedstock comprising a plant of the genus Cannabis with a hydrocarbon blend consisting essentially of a first hydrocarbon, a second hydrocarbon, and a third hydrocarbon at a temperature at or below -50°C to provide a hydrocarbon-based mixture; ii) isolating the hydrocarbon-based mixture from the feedstock; and iii) removing the hydrocarbon blend from the hydrocarbon- based mixture to produce the oil.

[0070] In another aspect, provided herein is an oil comprising a plurality of cannabinoids or terpenoids, or a combination thereof, obtained by: i) contacting a feedstock comprising a plant of the genus Cannabis with a hydrocarbon blend consisting essentially of a first hydrocarbon, a second hydrocarbon, and a third hydrocarbon at a temperature at or below -60°C to provide a hydrocarbon-based mixture; ii) isolating the hydrocarbon-based mixture from the feedstock; and iii) removing the hydrocarbon blend from the hydrocarbon- based mixture to produce the oil.

[0071] In some embodiments, the first hydrocarbon is n-butane.

[0072] In some embodiments, the second hydrocarbon is propane.

[0073] In some embodiments, the third hydrocarbon is isobutane.

[0074] In some embodiments, the n-butane is present in the hydrocarbon blend in an amount of about 50 weight % to about 90 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the n-butane is present in the hydrocarbon blend in an amount of about 80 weight % to about 90 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the n-butane is present in the hydrocarbon blend in an amount of about 85 weight % based on the total weight of the hydrocarbon blend.

[0075] In some embodiments, the propane is present in the hydrocarbon blend in an amount of about 5 weight % to about 25 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the propane is present in the hydrocarbon blend in an amount of about 5 weight % to about 15 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the propane is present in the hydrocarbon blend in an amount of about 10 weight % based on the total weight of the hydrocarbon blend.

[0076] In some embodiments, the isobutane is present in the hydrocarbon blend in an amount of about 1 weight % to about 15 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the isobutane is present in the hydrocarbon blend in an amount of about 1 weight % to about 10% weight % based on the total weight of the hydrocarbon blend. In some embodiments, the isobutane is present in the hydrocarbon blend in an amount of about 5 weight % based on the total weight of the hydrocarbon blend.

[0077] In some embodiments, the plant of the genus Cannabis is Cannabis sativa or

Cannabis indica.

[0078] In some embodiments, the feedstock is a fresh frozen feedstock.

[0079] In some embodiments, the oil is characterized by a higher concentration of terpenes and/or cannabinoids relative to an oil produced by: i) contacting a feedstock comprising a plant of the genus Cannabis with a hydrocarbon mixture essentially consisting of n-butane and propane in about 7:3 weight ratio at a temperature at or below -50°C to provide a hydrocarbon-based blend; ii) isolating the hydrocarbon-based blend from the feedstock; and iii) removing the hydrocarbon mixture from the hydrocarbon-based blend to produce the oil.

[0080] In some embodiments, the oil is characterized as having substantially less color relative to an oil produced by: i) contacting a feedstock comprising a plant of the genus Cannabis with a hydrocarbon mixture essentially consisting of n-butane and propane in about 7:3 weight ratio at a temperature at or below -50°C to provide a hydrocarbon-based blend; ii) isolating the hydrocarbon-based blend from the feedstock; and iii) removing the hydrocarbon mixture from the hydrocarbon-based blend to produce the oil.

[0081] In some embodiments, the oil is characterized by a higher concentration of terpenes and/or cannabinoids relative to an oil produced by: i) contacting a feedstock comprising a plant of the genus Cannabis with a hydrocarbon mixture essentially consisting of n-butane and propane in about 7:3 weight ratio at a temperature at or below -60°C to provide a hydrocarbon-based blend; ii) isolating the hydrocarbon-based blend from the feedstock; and iii) removing the hydrocarbon mixture from the hydrocarbon-based blend to produce the oil. In some embodiments, the higher concentration is 1% to 1,000% higher. In some embodiments, the higher concentration is 1%, 5%, 10%, 15%, 20% 25%, 30%, 35%, 40%, 45%, 50%, 55%, 25%, 30%, 35%, 40%, 50%, 60%, 70%, 80%, 90%, 100%, 150%, 200%, 300%, 400%, or 500% higher. In some embodiments, the oil is characterized by a higher concentration of terpenes and/or cannabinoids relative to an oil produced by: i) contacting a feedstock comprising a plant of the genus Cannabis with a hydrocarbon mixture essentially consisting of n-butane and propane in about 7:3 weight ratio at a temperature at or below -60°C to provide a hydrocarbon-based blend; ii) isolating the hydrocarbon-based blend from the feedstock; and iii) removing the hydrocarbon mixture from the hydrocarbon-based blend to produce the oil.

[0082] In some embodiments, the oil is characterized as having substantially less color relative to an oil produced by: i) contacting a feedstock comprising a plant of the genus Cannabis with a hydrocarbon mixture essentially consisting of n-butane and propane in about 7:3 weight ratio at a temperature at or below -60°C to provide a hydrocarbon-based blend; ii) isolating the hydrocarbon-based blend from the feedstock; and iii) removing the hydrocarbon mixture from the hydrocarbon-based blend to produce the oil.

[0083] In another aspect, provided herein is a composition comprising a feedstock comprising a plant of the genus Cannabis admixed with a hydrocarbon blend consisting essentially of n-butane, propane, and isobutane.

[0084] In some embodiments, the n-butane is present in the hydrocarbon blend in an amount of about 50 weight % to about 90 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the n-butane is present in the hydrocarbon blend in an amount of about 80 weight % to about 90 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the n-butane is present in the hydrocarbon blend in an amount of about 85 weight % based on the total weight of the hydrocarbon blend.

[0085] In some embodiments, the propane is present in the hydrocarbon blend in an amount of about 5 weight % to about 25 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the propane is present in the hydrocarbon blend in an amount of about 5 weight % to about 15 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the propane is present in the hydrocarbon blend in an amount of about 10 weight % based on the total weight of the hydrocarbon blend.

[0086] In some embodiments, the isobutane is present in the hydrocarbon blend in an amount of about 1 weight % to about 15 weight % based on the total weight of the hydrocarbon blend. In some embodiments, the isobutane is present in the hydrocarbon blend in an amount of about 1 weight % to about 10% weight % based on the total weight of the hydrocarbon blend. In some embodiments, the isobutane is present in the hydrocarbon blend in an amount of about 5 weight % based on the total weight of the hydrocarbon blend. [0087] In some embodiments, the plant of the genus Cannabis is Cannabis sativa or

Cannabis indica.

[0088] In some embodiments, the feedstock is a fresh frozen feedstock.

[0089] In some embodiments, the temperature is about -70 °C. In some embodiments, the temperature is about -80 °C. In some embodiments, the temperature is about -60 °C to about -80 °C. In some embodiments, the temperature is about -65 °C to about -80 °C.

[0090] In some embodiments, the oil comprises a total cannabinoid content of about

60% to about 90% by weight based on the weight of the oil. In some embodiments, the oil comprises a total terpenoid content of about 5% to about 15% by weight based on the weight of the oil. In some embodiments, the oil is characterized by an L* value of at least 30 (e.g., at least 35, e.g., about 35 to about 40) or an a* value less than 9 in the CIELAB color space. In some embodiments, the oil is characterized by an L* value of at least 30 (e.g., at least 35, e.g., about 35 to about 40) and an a* value less than 9 in the CIELAB color space.

EXAMPLES

EXAMPLE 1. Extraction of oils from exemplary cannabis feedstocks.

[0091] Extraction of samples from exemplary cannabis feedstocks was performed and their cannabinoid and terpenoid yields were analyzed. The oils were extracting using either (1) a solvent blend of butane, propane, and isobutane in a ratio of 85:5: 10 or (2) a solvent blend of butane and propane in a ratio of 70:30.

[0092] The extractions were performed in an extraction system. The procedure was as follows:

[0093] Solvent blends were cleaned before being entered into the extraction system.

A blend of 70/30 butane/propane and a blend of 85/5/10 blend of butane/propane/isobutane were distilled.

[0094] Solvent blends were isolated in the extraction system to eliminate the potential of cross contamination. The blend of 70/30 Butane/Propane was introduced into an isolated bank of the extraction system. The 85/5/10 blend of butane/propane/isobutane was loaded into the opposite isolated bank of the extraction system. The temperature of each solvent blend in the system was -70 °C.

[0095] Feedstock material (Leeroy OG x GG4) was winterized at -65 °C and then loaded as a fresh frozen sample into a single material vessel of the system. The weight of each fresh frozen feedstock sample was 10 lbs. The fresh frozen feedstock sample was then extracted using 35 lbs of one of the solvent blends.

[0096] Extraction of the feedstock then occurred at -70 °C with one of the loaded solvent blends. Extracts obtained from the feedstock sample was then obtained and isolated from the solvent blend. The solvent blends were recovered upon isolation from the oil; solvent blend recovery times were observed and recorded. Yields of terpenoid and cannabinoid content were determined based on weights of cannabinoids and terpenoids obtained.

Table 1. Exemplary feedstock extraction runs.

[0097] *In Table 1, "85/5/10 B/R/G: 85/5/10 butane/propane/isobutane; "70/30 B/P": 70/30 butane/propane.

[0098] Visual comparisons of extracts obtained from individual trials that utilized one of the solvent blends were then observed. Trials utilizing 85/5/10 blend of butane/propane/isobutane produced an extract that was lighter in color, visibly clearer, and had better cannabinoid crystalline formation than the blend of 70/30 butane/propane. The 85/5/10 blend of butane/propane/isobutane formed less, but larger nucleation sites than the 70/30 blend of butane/propane. Trials utilizing blends of 70/30 butane/propane trials resulted in a darker extract with more nucleation sites which was ultimately undesirable.

EXAMPLE 2. Extraction of oils from exemplary cannabis feedstocks.

[0099] Oils of cannabis samples extracted using a solvent blend of butane, propane, and isobutane in a ratio of 85:5: 10 at -50 °C, -60 °C, and -80 °C were evaluated for their cannabinoid and terpenoid contents.

[00100] In analyses performed, the following percentage calculations of the oils were made. Sum of Cannabinoids = D ⁹ -THC + THCa + CBD + CBDa + CBG + CBGa + THCV + THCVa + CBC + CBCa + CBDV + CBDVa + D ⁸ -THC + CBL + CBN; Total Cannabinoids = (D 9 -THC+0.877*THCa) + (CBD+0.877*CBDa) + (CBG+0.877*CBGa) +

(THCV +0.877* THCVa) + (CBC+0.877*CBCa) + (CBDV+0.877*CBDVa) + D ⁸ -THC + CBL + CBN; and Total THC/CBD is calculated using the following formulas to take into account the loss of a carboxyl group during the decarboxylation step: Total THC = D ⁹ -THC + (THCa (0.877)) Total CBD = CBD + (CBDa (0.877)). These cannabinoid test results were determined with high-performance liquid chromatography with diode-array detection (HPLC- DAD). Terpenoid content results were determined with gas chromatography-flame ionization detection (GC-FID).

[00101] In an exemplary 9.0 gram oil extracted from a cannabis sample at -50 °C (Green Crack-LB1240 (-50)), the sum of cannabinoids was determined to be 80.64%, total cannabinoids was determined to be 70.92%, total THC was determined to be 65.76%, and total CBD was determined to be 0.17%. Total terpenoids were determined to be 7.03%. Further, b-caryophyllene content was determined to be 21.289 mg/g, limonene content was determined to be 14.983 mg/g, and a-humulene was determined to be 9.239 mg/g.

[00102] In an exemplary 9.0 gram oil extracted from a cannabis sample at -60 °C (Green Crack-LB1240 (-60)), the sum of cannabinoids was determined to be 80.12%, total cannabinoids was determined to be 70.43%, total THC was determined to be 65.63%, and total CBD was determined to be 0.17%. Total terpenoids were determined to be 7.67%. Further, b-caryophyllene content was determined to be 23.157 mg/g, limonene content was determined to be 16.904 mg/g, and a-humulene was determined to be 9.983 mg/g. [00103] In an exemplary 6.0 gram oil extracted from a cannabis sample at -80 °C (Green Crack-LB1240 (-80)), the sum of cannabinoids was determined to be 82.34%, total cannabinoids was determined to be 72.37%, total THC was determined to be 68.17%, and total CBD was determined to be 0.14%. Total terpenoids were determined to be 6.48%. Further, b-caryophyllene content was determined to be 19.444 mg/g, limonene content was determined to be 14.762 mg/g, and a-humulene was determined to be 8.461 mg/g.

EXAMPLE 3. Color Analysis of oils.

[00104] Oils of cannabis samples extracted using a solvent blend of butane, propane, and isobutane in a ratio of 85:5: 10 at -80 °C were evaluated using the CIELAB color space. L* is a measurement of lightness that defines black as zero and white as 100. The a* value describes the sample hue along a green-red axis where negative values represent increased green and positive values increased red. Measurements were obtained using 1-3 g of oil on a VISTA color analyzer (Hunter Associates Laboratory). These parameters translate visually to oil that is lighter in hue and yellow in color rather than dark or reddish-orange. Average values of oil yields, cannabinoid percentage, terpenoid percentage, L*, and a* values across 68 oil samples are provided in Table 2 below.

Table 2.

EQUIVALENTS AND SCOPE

[00105] In the claims articles such as "a," "an," and "the" may mean one or more than one unless indicated to the contrary or otherwise evident from the context. Claims or descriptions that include "or" between one or more members of a group are considered satisfied if one, more than one, or all of the group members are present in, employed in, or otherwise relevant to a given product or process unless indicated to the contrary or otherwise evident from the context. The invention includes embodiments in which exactly one member of the group is present in, employed in, or otherwise relevant to a given product or process. The invention includes embodiments in which more than one, or all of the group members are present in, employed in, or otherwise relevant to a given product or process. [00106] Furthermore, the invention encompasses all variations, combinations, and permutations in which one or more limitations, elements, clauses, and descriptive terms from one or more of the listed claims is introduced into another claim. For example, any claim that is dependent on another claim can be modified to include one or more limitations found in any other claim that is dependent on the same base claim. Where elements are presented as lists, e.g., in Markush group format, each subgroup of the elements is also disclosed, and any element(s) can be removed from the group. It should it be understood that, in general, where the invention, or aspects of the invention, is/are referred to as comprising particular elements and/or features, certain embodiments of the invention or aspects of the invention consist, or consist essentially of, such elements and/or features. For purposes of simplicity, those embodiments have not been specifically set forth in haec verba herein. It is also noted that the terms "comprising" and "containing" are intended to be open and permits the inclusion of additional elements or steps. Where ranges are given, endpoints are included. Furthermore, unless otherwise indicated or otherwise evident from the context and understanding of one of ordinary skill in the art, values that are expressed as ranges can assume any specific value or sub-range within the stated ranges in different embodiments of the invention, to the tenth of the unit of the lower limit of the range, unless the context clearly dictates otherwise.

[00107] This application refers to various issued patents, published patent applications, journal articles, and other publications, all of which are incorporated herein by reference. If there is a conflict between any of the incorporated references and the instant specification, the specification shall control. In addition, any particular embodiment of the present invention that falls within the prior art may be explicitly excluded from any one or more of the claims. Because such embodiments are deemed to be known to one of ordinary skill in the art, they may be excluded even if the exclusion is not set forth explicitly herein. Any particular embodiment of the invention can be excluded from any claim, for any reason, whether or not related to the existence of prior art.

[00108] Those skilled in the art will recognize or be able to ascertain using no more than routine experimentation many equivalents to the specific embodiments described herein. The scope of the present embodiments described herein is not intended to be limited to the above Description, but rather is as set forth in the appended claims. Those of ordinary skill in the art will appreciate that various changes and modifications to this description may be made without departing from the spirit or scope of the present invention, as defined in the following claims.