WO2022251329A1 - Systèmes et procédés d'extraction de matériaux - Google Patents

Systèmes et procédés d'extraction de matériaux Download PDF

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Publication number
WO2022251329A1
WO2022251329A1 PCT/US2022/030880 US2022030880W WO2022251329A1 WO 2022251329 A1 WO2022251329 A1 WO 2022251329A1 US 2022030880 W US2022030880 W US 2022030880W WO 2022251329 A1 WO2022251329 A1 WO 2022251329A1
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Prior art keywords
hydrocarbon
blend
weight
oil
feedstock
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PCT/US2022/030880
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English (en)
Inventor
Thomas Martin
Joel ENOKI
Matt LIMON
Khalid AL-NASER
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Central Coast Agriculture, Inc.
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Publication of WO2022251329A1 publication Critical patent/WO2022251329A1/fr

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/0288—Applications, solvents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)

Definitions

  • Cannabis extracted from cannabis flower embodies new opportunities and safer ways to consume cannabis.
  • the choice of solvent is important in regards of the final product consistency and purity.
  • compositions comprising a feedstock comprising a plant of the genus Cannabis admixed with a hydrocarbon blend.
  • 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 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.
  • 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 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.
  • the first hydrocarbon is n-butane.
  • the second hydrocarbon is propane.
  • the third hydrocarbon is isobutane.
  • 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.
  • 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.
  • 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
  • the feedstock is a fresh frozen feedstock.
  • 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-y
  • 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.
  • cannabinoids selected from the group consisting of tetrahydrocannabinol, cannabigerol, cannabichromene, tetrahydrocannabivarin, cannabidiol, cannabinol, cannabigerivarin, tetrahydrocannabivarian, cannabidivarin, cannabichromevarin, and carboxylic acid derivatives thereof.
  • the contacting step is carried out a temperature from about -68 to -72°C.
  • the temperature is about -70 °C.
  • the oil is characterized by a color that is substantially the same as depicted in FIG. 1.
  • 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.
  • 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.
  • the first hydrocarbon is n-butane.
  • the second hydrocarbon is propane.
  • the third hydrocarbon is isobutane.
  • 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.
  • 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.
  • 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.
  • the plant of the genus Cannabis is Cannabis sativa or
  • the feedstock is a fresh frozen feedstock.
  • 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.
  • 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.
  • 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.
  • composition comprising a feedstock comprising a plant of the genus Cannabis admixed with a hydrocarbon blend consisting essentially of n-butane, propane, and isobutane.
  • 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.
  • 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.
  • 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.
  • the plant of the genus Cannabis is Cannabis sativa or
  • the feedstock is a fresh frozen feedstock.
  • 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.
  • 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.
  • any and all isomeric, enantiomeric, or optically active derivatives are also encompassed.
  • reference to a particular cannabinoid includes both the "A Form” and the "B Form”.
  • 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).
  • 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.
  • Cannabinoids include tetrahydrocannabinolic acid, tetrahydrocannabinol, cannabigerol, cannabichromene, tetrahydrocannabivarin, cannabidiol, cannabinol, cannabigerivarin, tetrahydrocannabivarian, cannabidivarin, cannabichromevarin, and derivatives thereof.
  • 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
  • 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.
  • Tepenoid-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.
  • 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.
  • 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
  • pluricity of terpenoids refers to a mixture of one or more terpenoids.
  • plality of cannabinoids refers to a mixture of more than one cannabinoid.
  • 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
  • the present disclosure describes, in part, methods of extracting a composition
  • a feedstock comprising a plant of the genus Cannabis.
  • 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.
  • a plant material e.g., plant of the genus Cannabis
  • 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.
  • the methods of extracting described herein comprise contacting the feedstock with a solvent.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • the solvent is n-butane, propane, or isobutane
  • the solvent is a hydrocarbon or a hydrocarbon blend.
  • the hydrocarbon blend comprises a first hydrocarbon, a second hydrocarbon, and a third hydrocarbon.
  • the hydrocarbon consists essentially of a first hydrocarbon, a second hydrocarbon, and a third hydrocarbon.
  • the first hydrocarbon is n-butane.
  • the second hydrocarbon is propane.
  • the third hydrocarbon is isobutane.
  • 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.
  • 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.
  • 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.
  • 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
  • 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.
  • the genus Cannabis is Cannabis sativa, Cannabis indica , or Cannabis ruderalis.
  • the plant of the genus Cannabis is Cannabis sativa or Cannabis indica.
  • the feedstock is a fresh frozen feedstock.
  • 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-ylene
  • 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.
  • the contacting step is carried out a temperature from about -68 to -72°C.
  • 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.
  • 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.
  • the oil is characterized by a color that is substantially the same as depicted in FIG. 1.
  • 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.
  • 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.
  • the first hydrocarbon is n-butane.
  • the second hydrocarbon is propane.
  • the third hydrocarbon is isobutane.
  • 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.
  • 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.
  • 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.
  • the plant of the genus Cannabis is Cannabis sativa or
  • the feedstock is a fresh frozen feedstock.
  • 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.
  • 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.
  • 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.
  • the higher concentration is 1% to 1,000% higher.
  • 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.
  • 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.
  • 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.
  • composition comprising a feedstock comprising a plant of the genus Cannabis admixed with a hydrocarbon blend consisting essentially of n-butane, propane, and isobutane.
  • 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.
  • 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.
  • 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
  • the feedstock is a fresh frozen feedstock.
  • 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.
  • the oil comprises a total cannabinoid content of about
  • the oil comprises a total terpenoid content of about 5% to about 15% by weight based on the weight of the oil.
  • 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.
  • 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.
  • EXAMPLE 1 Extraction of oils from exemplary cannabis feedstocks.
  • 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.
  • 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.
  • 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.
  • Table 1 Exemplary feedstock extraction runs.
  • 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.
  • HPLC- DAD high-performance liquid chromatography with diode-array detection
  • GC-FID gas chromatography-flame ionization detection
  • 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.
  • 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.
  • 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.
  • 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.

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Abstract

La présente divulgation concerne des procédés d'extraction d'une huile comprenant une pluralité de cannabinoïdes ou de terpénoïdes, des huiles obtenues par l'intermédiaire desdits procédés d'extraction, ainsi que des compositions mélangées à un mélange d'hydrocarbures.
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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140271940A1 (en) * 2013-03-14 2014-09-18 Sc Laboratories, Inc. Bioactive concentrates and uses thereof
US20170020944A1 (en) * 2015-03-11 2017-01-26 Tyrell R. Towle Systems and methods for cannabinoid and terpene extraction and purification
US20190151771A1 (en) * 2016-05-02 2019-05-23 Natural Extraction Systems, LLC Improved method and apparatus for extracting botanical oils
US20190185783A1 (en) * 2017-12-19 2019-06-20 Botanex Intellectual Property LLC Modular, mobile, and automated solvent extraction and distillation systems, and methods of using the same
US20210154596A1 (en) * 2019-11-21 2021-05-27 Jenny's Rose, LLC Cannabis Plant Extracts with Butane

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140271940A1 (en) * 2013-03-14 2014-09-18 Sc Laboratories, Inc. Bioactive concentrates and uses thereof
US20170020944A1 (en) * 2015-03-11 2017-01-26 Tyrell R. Towle Systems and methods for cannabinoid and terpene extraction and purification
US20190151771A1 (en) * 2016-05-02 2019-05-23 Natural Extraction Systems, LLC Improved method and apparatus for extracting botanical oils
US20190185783A1 (en) * 2017-12-19 2019-06-20 Botanex Intellectual Property LLC Modular, mobile, and automated solvent extraction and distillation systems, and methods of using the same
US20210154596A1 (en) * 2019-11-21 2021-05-27 Jenny's Rose, LLC Cannabis Plant Extracts with Butane

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ANONYMOUS: "CIELAB color space", WIKIPEDIA, 12 December 2020 (2020-12-12), XP093013353, Retrieved from the Internet <URL:https://en.wikipedia.org/w/index.php?title=CIELAB_color_space&oldid=993825817> [retrieved on 20230112] *

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