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WO2021118539A1 - Systèmes, procédés, et équipement d'extraction chimique - Google Patents

Systèmes, procédés, et équipement d'extraction chimique Download PDF

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Publication number
WO2021118539A1
WO2021118539A1 PCT/US2019/065500 US2019065500W WO2021118539A1 WO 2021118539 A1 WO2021118539 A1 WO 2021118539A1 US 2019065500 W US2019065500 W US 2019065500W WO 2021118539 A1 WO2021118539 A1 WO 2021118539A1
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WIPO (PCT)
Prior art keywords
feedstock
motive gas
chemical compound
gas
plant material
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2019/065500
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English (en)
Inventor
Raechel SHERWOOD
Steven Sherwood
Reese CULLIMORE
Greg MEHOS
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Loxley Systems LLC
Original Assignee
Loxley Systems LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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Priority to PCT/US2019/065500 priority Critical patent/WO2021118539A1/fr
Publication of WO2021118539A1 publication Critical patent/WO2021118539A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D5/00—Condensation of vapours; Recovering volatile solvents by condensation
    • B01D5/0078—Condensation of vapours; Recovering volatile solvents by condensation characterised by auxiliary systems or arrangements
    • B01D5/009—Collecting, removing and/or treatment of the condensate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/10—Vacuum distillation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/34—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances
    • B01D3/40—Extractive distillation
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/02—Recovery or refining of essential oils from raw materials
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/02—Recovery or refining of essential oils from raw materials
    • C11B9/027—Recovery of volatiles by distillation or stripping
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/10—Greenhouse gas [GHG] capture, material saving, heat recovery or other energy efficient measures, e.g. motor control, characterised by manufacturing processes, e.g. for rolling metal or metal working

Definitions

  • the present invention relates generally to a novel thermal evaporative process for the recovery of heat-sensitive constituents, raw essential oil concentrates, and other compounds from plant biomass material, and particularly to a solvent-less process for either batch-wise or continuous removal and recovery of refined oils, such as volatile aroma components and heavier oils, from plant material.
  • a solvent which is usually either a hydrocarbon-based solvent (e.g. an alcohol or butane) or a high- pressure (e.g. supercritical CO 2 ) gas.
  • Patent 7,622,140 entitled “Processes and apparatus for extraction of active substances and enriched extracts from natural products,” issued 24 November 2009 to Whittle et al. (“Whittle”).
  • S. Casano et al. “Variations in terpene profiles of different strains of Cannabis sativa L.,” 925 Acta Horticulturae 115 (Dec.2011).
  • S. Elzinga et al. “Cannabinoids and terpenes as chemotaxonomic markers in cannabis,” 3 Natural Products Chemistry & Research 181 (July 2015) (“Elzinga”).
  • Previous methods and systems, including but not limited to those disclosed in Whittle, have attempted to overcome the above-identified limitations.
  • a method for extracting at least one chemical compound from plant material comprising a) preparing a feedstock by at least one of chopping, cutting, treating, pelletizing, and grinding the plant material; b) preheating the feedstock to a first temperature at atmospheric or sub-atmospheric pressure for a preselected time to form a preheated feedstock; c) heating the preheated feedstock to a second temperature at sub-atmospheric pressure in an evaporation chamber to form a heated feedstock; d) flowing a heated motive gas through the evaporation chamber to drive the at least one chemical compound from the heated feedstock, thereby forming a pregnant motive gas; and e) condensing a portion of the pregnant motive gas to
  • the plant material may comprise a plant of the genus Cannabis.
  • the first temperature may be at least about 110 °C.
  • the first time may be between about 10 minutes and about 120 minutes.
  • the second temperature may be between about 120°C and about 200 °C.
  • the second time may be between about 20 minutes and about 200 minutes.
  • the motive gas may comprise a non-oxidizing gas.
  • the motive gas may, but need not, comprise at least one gas selected from the group consisting of helium, argon, an inert gas other than helium and argon, air, nitrogen, CO 2 , and superheated steam.
  • a temperature of the heated motive gas in step d) may be between about 120 °C and about 250 °C.
  • the at least one chemical compound may comprise at least one cannabinoid.
  • the at least one chemical compound may comprise at least one terpene or terpenoid.
  • the pressures in the preheater and the vacuum evaporator may both be between about 0.02 inHg absolute and about 14 inHg absolute.
  • the system may be configured to drive a first chemical compound from the feedstock in the preheater and a second chemical compound from the preheated feedstock in the vacuum evaporator, and to recover the first and second chemical compounds in the recovery unit.
  • the pressure in the preheater may be about atmospheric pressure and the pressure in the vacuum evaporator may be between about 0.02 inHg absolute and about 14 inHg.
  • the system may be configured to drive a first chemical compound from the feedstock in the preheater and collect the first chemical compound in the first recovery unit, and to drive a second chemical compound from the preheated feedstock in the vacuum evaporator and collect the second chemical compound in the second recovery unit.
  • each of the expressions “at least one of A, B, and C,” “at least one of A, B, or C,” “one or more of A, B, and C,” “one or more of A, B, or C,” and “A, B, and/or C” means A alone, B alone, C alone, A and B together, A and C together, B and C together, or A, B, and C together.
  • the term “a” or “an” entity refers to one or more of that entity.
  • the terms “a” (or “an”), “one or more,” and “at least one” can be used interchangeably herein.
  • the terms “comprising,” “including,” and “having” can be used interchangeably.
  • Figure 1 is a generalized flowchart illustrating a laboratory-scale method for extraction of target compounds from plant material at biomass feed rates of up to a few hundred pounds per day, according to embodiments of the present invention.
  • Figure 2 is a schematic of a laboratory-scale system for extraction of target compounds from plant material, according to embodiments of the present invention.
  • Figure 3 is a schematic of a system for the extraction of targeted compounds from plant material operable to process larger quantities of biomass on the order of multiple tons per day, according to embodiments of the present invention.
  • Figure 4 is a graph showing the CBD content of a crushed pelletized hemp plant material as a function of extraction time in Example 2 of the present application.
  • feedstock refers to size- reduced plant material.
  • chopped, cut, or ground cannabis plants constitute a cannabis feedstock within the meaning of the present application.
  • plant material refers to whole plants and/or parts of plants that contain one or more compounds to be extracted, including but not limited to aerial parts, leaves, stems, flowering heads, fruits, and/or roots.
  • Plant material may be freshly harvested plants or parts of plants, plants or parts of plants that have been subjected to one or more pre-treatment steps (e.g. drying, removal of debris, etc.), and/or plants or parts of plants that have been frozen or pelletized.
  • pre-treatment steps e.g. drying, removal of debris, etc.
  • the term “treating,” when applied to plant material refers to biomass surface digestion processes, i.e. processes in which at least a portion of a surface of the plant material is digested, disrupted, or dissolved, either chemically or physically.
  • a plant material that has been subjected to a surface digestion process e.g. using acid, caustic chemicals, or other chemical processes, or using physical disruption, is thus a “treated” plant material.
  • the present invention may be suitably applied to any plant or other biomass material to extract any compound that may be obtained by distillation.
  • the present invention may be employed to extract essential oils or other volatile compounds from spices, fruits, flowers, or any other suitable plant material, as such embodiments are within the scope of the present invention.
  • Methods of extracting a target compound from plant material generally comprise coarsely chopping, cutting, or grinding plant material; preheating the feedstock under atmospheric or sub-atmospheric pressure to drive off moisture and collect volatile compounds having a relatively low boiling point (e.g. terpenes); subsequently subjecting the feedstock to a flow of a motive gas, and optionally further heating the feedstock to collect volatile compounds having a relatively high boiling point (e.g. cannabinoids); and condensing the collected volatile compounds to form one or more extract products.
  • a relatively low boiling point e.g. terpenes
  • a relatively high boiling point e.g. cannabinoids
  • the methods exhibit advantageous efficiency and selectivity as compared to prior art methods of solvent extraction, especially in relation to the isolation of high-purity, cannabinoid-rich fractions, which in embodiments may contain over 80% total cannabinoids, from cannabis plant material.
  • the methods may be operated in either a batch mode or a continuous mode and are therefore particularly suitable for use in large-scale commercial production of extracts from natural products.
  • Plant material for use in the present invention may be, by way of non-limiting example, whole plants, aerial parts, leaves, stems, flowering heads, fruits, and/or roots, and may be freshly harvested, dried, frozen and/or pelletized. When using freshly harvested plant material, e.g.
  • the methods of the invention may advantageously include a pre-treatment step in which the plant material is dried to remove water vapor therefrom.
  • the temperature of the motive gas used to volatilize compounds having relatively high boiling points, e.g. cannabinoids, may vary depending on the nature of the plant material and the target compounds. In embodiments, the temperature will generally be selected to avoid pyrolysis of the plant material or degradation of any target compounds contained therein.
  • Motive gas temperatures typical of embodiments of the present invention may be between about 120 °C and about 250 °C. Certain steps of the methods of the invention are advantageously carried out at sub-atmospheric pressure, and in some embodiments absolute vacuum or near-vacuum.
  • Motive gases suitable for use in the process may include warm or hot air.
  • non-oxidizing gas instead may be desirable.
  • non-oxidizing gases include but are not limited to CO 2 , nitrogen, superheated steam, and inert gases such as helium and argon.
  • the temperature of the extraction steps may be varied over the course of the extraction process. In embodiments, two or more discrete temperature steps may be used. Where multiple temperature steps are used, it is generally desirable that the temperature be increased at each step. The use of two or more discrete temperatures may be beneficial where, by way of non-limiting example, it is desired to extract two or more target compounds of different boiling points. The present inventors have found that heating the feedstock may also encourage desirable chemical reactions of the constituent compounds present in the feedstock.
  • the principal active constituents of Cannabis sativa and Cannabis indica are the cannabinoids; tetrahydrocannabinol (THC) and cannabidiol (CBD) are the most common cannabinoids, but others (e.g. cannabigerol (CBG) and cannabichromene (CBC)) are often present in smaller quantities and may be desirable in certain applications.
  • THC cannabigerol
  • CBC cannabichromene
  • the bulk of the cannabinoids present in the cannabis plant are present not in free or neutral form but as their corresponding carboxylic acids, which typically exhibit little or no biological activity.
  • cannabinoid carboxylic acids it is necessary to convert the cannabinoid carboxylic acids into their corresponding free cannabinoids before extraction; prior art methods have generally accomplished this decarboxylation by preheating in a separate step.
  • the present inventors have found that by extracting cannabinoids from cannabis at elevated temperatures (e.g. between about 120 and about 200 °C) for a suitable period of time (e.g. between about 20 and about 200 minutes), the cannabinoid carboxylic acids may be converted into free cannabinoids without the need for a separate decarboxylation step.
  • decarboxylation and evaporation of the cannabinoids may be accomplished simultaneously in a single step by heating the feedstock under atmospheric or sub- atmospheric pressure.
  • temperatures and times for the heating steps of the methods of the present invention may vary according to the particular cannabinoids or other compounds that are to be extracted, as well as the consideration of running the process in a batch mode or a continuous mode.
  • certain chemotypes of cannabis express a high proportion of their total cannabinoid content as THC, or as CBD.
  • an extraction temperature may be selected to prevent thermal oxidation of CBD to ⁇ 8 -THC, ⁇ 9 -THC and other degradation products.
  • operating temperatures should be selected to limit the conversion of ⁇ 9 -THC to ⁇ 8 -THC and cannabinol (CBN). As discussed below, these temperatures may be adjusted to produce extracts that are higher or lower in compounds having higher or lower boiling points; by way of non- limiting example, where a cannabis extract high in cannabinoids and low in terpenes is desired, a somewhat higher temperature may be used to drive off the more volatile terpenes and preserve the cannabinoids. Other factors, including but not limited to the flow rate of the feedstock and/or motive gas, residence time, the choice of batch versus continuous processing, and the condensation conditions, may affect the preferred extraction temperature and time.
  • the extracts are characterized by a high degree of purity of the free cannabinoids and heavy terpenes, and in many embodiments are substantially free of waxes, sterols, and other lipid-soluble compounds that are common in extracts produced by the solvent-based methods and CO 2 systems of the prior art.
  • the relatively selective CO 2 extraction processes of the prior art typically yield extracts that are about 65 wt% cannabinoid
  • the present invention is suitable for producing extracts of at least about 80 wt% cannabinoid, and as much as about 90 wt% cannabinoid, particularly from relatively cannabinoid-rich feedstocks.
  • the obtained composition may represent a mixture of at least about 80 wt% combined cannabinoids and terpenes/terpenoids.
  • the methods and systems of the present invention thus exhibit significantly increased selectivity for cannabinoids relative to the methods and systems of the prior art.
  • Most of the undesired or waste mass/ballast of cannabis plants consists of involatile material.
  • the methods and systems of the present invention efficiently separate the desired active cannabinoids from this involatile ballast by volatilizing the cannabinoids, but not the ballast.
  • methods and systems of the present invention may use a single-step temperature profile to produce a cannabinoid-rich extract substantially free of volatile terpenes, wherein the majority of the cannabinoids are present in the biologically active free or neutral form rather than as their naturally occurring carboxylic acids; as a result, neither a separate decarboxylation step (to convert the cannabinoids to the free form) nor a separate “winterization” step (to remove terpenes and other undesired compounds) is necessary, representing a clear advantage over methods and systems of the prior art.
  • cannabis extracts produced by the present invention contain a blend of cannabinoids in approximately the same proportion as are present in the raw cannabis plant material. In other words, little or no fractionation of cannabinoids may be observed so a “Full Spectrum” product is produced that reflects the cannabinoid profile of the feedstock. It may be advantageous to process high-THC and high-CBD chemotypes of cannabis separately to produce extracts rich in CBD or THC respectively, from which mixtures containing desired concentrations of THC and/or CBD can be made.
  • the present invention provides apparatuses and systems for extracting target compounds from plant material without the use of a hydrocarbon-derived, alcohol, or CO 2 solvents.
  • the apparatuses and systems generally comprise a pretreatment unit, wherein chopped, cut, pelletized, or ground plant material; a hopper, dispensing the feedstock; a preheater, configured to drive off moisture from the feedstock and optionally collect volatile compounds having a relatively low boiling point; an evaporator wherein a motive gas flows to the feedstock, and the feedstock is optionally further heated, to collect volatile compounds having a relatively high boiling point; and a vapor recovery units, wherein one or more plant extracts are condensed.
  • plant material is first placed in a feedstock preparation unit 100.
  • feedstock preparation unit 100 the plant material is first chopped, cut, or ground to increase the surface area of the plant material for subsequent processing.
  • the plant material need not be finely ground, and in fact it may be desirable in some embodiments for the plant material to contain minimal fines; a coarse chop, grind, or shred, e.g. passing between a 40-mesh and 0.25” sieve, is sufficient, but may require more specification depending on the nature of the plant material itself.
  • the unit may optionally comprise various further operations.
  • additional cleansing agents e.g.
  • surface-active agents, natural catalysts and/or enzymes, and caustic or acidic chemicals may be applied to the plant material; the plant material may be subjected to attritioning, steam explosion or other quick pressure reduction, or microwave or ultrasonic treatment; and/or the feedstock may be additionally exposed to conventional extraction processes, such as extraction by hydrocarbon- or alcohol-based solvents or high- pressure CO 2 , to make volatile constituents of the feedstock more available to downstream evaporation processes.
  • the feedstock is then passed to a feed hopper 200.
  • the hopper 200 is integrally interconnected to downstream operation units and is fitted with a double dump valve, rotary valve, or similar apparatus to maintain atmospheric to sub-atmospheric pressures, in some embodiments between about 2 inHg and about 14 inHg, while continuously feeding the downstream operation units.
  • the hopper 200 is preferably configured, e.g. by outlet size, wall steepness, low-friction construction, etc., to ensure that a stable rathole or arch does not develop and impede the flow of feedstock.
  • the hopper 200 may optionally comprise a rotary valve or screw to feed the feedstock to downstream operation units; when present, the screw of the hopper 200 preferably has a stepped or tapered shaft section, and optionally an increasing pitch section, to ensure reliable flow of the feedstock, especially where the outlet of the hopper 200 is a slot.
  • the hopper 200 may optionally comprise additional components, e.g. a removable lid to reduce leakage of air.
  • the feedstock is conveyed (by a pneumatic conveyance, gravity, auger, plunger, or other means of positive displacement transport) to an evaporator 300, which in the embodiment illustrated in Figure 1 comprises two stages: a preheater and/or Low-Temperature Evaporator 310, and a high-temperature evaporator 320.
  • the low-temperature evaporator 310 may comprise a screw-type or tube-in- tube heat exchanger, wherein the feedstock is conveyed along a length of the heat exchanger through a heated trough by a screw. The screw may or may not be heated.
  • the low-temperature evaporator 310 may comprise a moving bed heat exchanger, wherein material flows by gravity between heated plates. Where a screw-type heat exchanger is used, the screw preferably has the same diameter as an outlet of the feed hopper 200.
  • the low-temperature evaporator 310 is preferably maintained at a temperature of at least about 110 °C, and at sub-atmospheric pressures (preferably between about 0.02 inHg absolute and about atmospheric pressure), to assist in driving off moisture and volatile compounds having relatively low boiling points; vapors of these volatile constituents then exit through a gas exhaust port.
  • the high-temperature evaporator 320 comprises a screw with a gas-permeable shaft, a gas-permeable cylindrical trough, and a gas-impermeable cylinder.
  • the gas-impermeable cylinder surrounds and has a larger diameter than the gas-permeable cylindrical trough, thereby forming an annular space between the gas-permeable cylindrical trough and the gas-impermeable cylinder.
  • the high-temperature evaporator 320 is maintained at sub-atmospheric pressure, preferably between about 0.02 inHg absolute and about 14 inHg absolute, and is heated or insulated to maintain a desired extraction temperature, most typically between about 120 °C and about 200 °C.
  • a heated motive gas also referred to as a stripping gas
  • Flow of the motive gas through the high-temperature evaporator 320 may be any combination of co-current with, counter-current to, and/or cross-current to the flow of the feedstock and may have any suitable flow rate, which in typical embodiments may (but need not) be between about 0.10 and about 40 standard liters per minute for every pound per hour of solid feed material; more generally, a ratio of the flow rate of the heated motive gas to the flow rate of the feedstock may be between about 1 standard liter per pound and about 12,000 standard liters per pound, or between about 6 standard liters per pound and about 2,400 standard liters per pound. In this way, volatilizable compounds having a relatively high boiling point, e.g.
  • the motive gas may be any suitable gas, including but not limited to an inert gas (helium, argon, etc.), air, CO 2 , nitrogen, superheated steam, etc., and may preferably be a non-oxidizing gas.
  • the high-temperature evaporator 320 may, in operation, be substantially or completely filled with feedstock material, or it may be partially filled, at least in a portion, by increasing the pitch of the screw. Lifters or paddles may be installed in appropriate portions of the high-temperature evaporator 320 to promote mixing and movement of the feedstock.
  • the solids exit port of the high-temperature evaporator 320 also typically comprises a rotary air lock, slide gate valve, or double dump valve to form a seal between the high-temperature evaporator 320 and downstream operational units.
  • the gas-permeable cylindrical trough constitutes an inner “shell” of the high-temperature evaporator 320, wherein the inner shell rotates on an auger. Blades of the auger may be disposed on the inner shell, promoting motion of the feedstock through the high-temperature evaporator 320.
  • the gas-impermeable cylinder thus constitutes the outer “shell” of the high-temperature evaporator 320 to define the annular space within the evaporator, and may comprise a gas exhaust port, preferably near a longitudinal center of the high-temperature evaporator 320, through which the motive gas and the extracted compounds exit the evaporator.
  • the motive gas may be introduced into the high-temperature evaporator 320 by a small-diameter gas dispersion membrane, which may (but need not) be mounted to an auger to transport the motive gas through the high-temperature evaporator 320, and a larger-diameter gas dispersion membrane may be positioned about the auger to provide cross-flow contact of the motive gas with the feedstock, thus allowing for pregnant motive gas containing the evaporated product materials to be collected in a void and/or annular space.
  • the remnants of the feedstock e.g. dried and substantially or completely devolatilized plant material
  • the system may also comprise means 500 for metering and/or heating the motive gas, which may in embodiments comprise at least one of a gas generation system (e.g. steam boiler or nitrogen generator), a gas metering device, and a gas heater/temperature controller.
  • a gas generation system e.g. steam boiler or nitrogen generator
  • the motive gas and volatile compounds extracted from the feedstock exit the high- temperature evaporator 320 via the exhaust port and are then passed to a vapor recovery module 600.
  • the vapor recovery module 600 typically comprises a coiled tube-in-tube heat exchanger, whereby the volatile compounds are condensed.
  • the volatile compounds may condense and coalesce directly on a surface of the heat exchanger, and then drip into, precipitate into, or otherwise be collected in an extract collection vessel.
  • the process gases and vapors condensed and collected in this way can, in suitable embodiments, coalesce with minimal pressure loss.
  • remaining extraction products e.g. monoterpenes and lighter sesquiterpenes
  • Additional coalescing, condensing, phase separation, and recovery techniques may also be employed, including but not limited to liquid-phase recovery, cyclone recovery, and demisting operations.
  • the motive gas and unrecoverable volatile products are pulled via the vacuum pump 700 out of the recovery module 600 to be recycled, remediated, separated, further processed, and/or vented to the atmosphere.
  • the vacuum pump 700 may also be used to provide suitable sub-atmospheric pressures in any one or more other components of the system, including but not limited to the preheater and/or low-temperature evaporator 310 and/or the high-temperature evaporator 320.
  • plant material is first placed in a feedstock preparation unit 800.
  • the plant material is first chopped, cut, or ground to increase the surface area of the plant material for subsequent processing. It may be desirable in some embodiments for the plant material to contain minimal fines; a coarse chop, grind, or shred, e.g.
  • the feedstock is then passed to a feed hopper 900.
  • the hopper 900 is integrally interconnected to downstream operation units and is fitted with a double dump valve, rotary valve, or similar apparatus to maintain sub- atmospheric or atmospheric pressures, in some embodiments between about 0.02 inHg absolute and about 30 inHg absolute, while continuously feeding the downstream operation units.
  • the hopper 900 is preferably configured (e.g. by outlet size, wall steepness, low- friction construction, etc.) to ensure that a stable rathole or arch does not develop and impede the flow of feedstock.
  • the feed hopper 900 may optionally comprise a screw to feed the feedstock to downstream operation units; when present, the screw of the hopper 900 preferably has a stepped or tapered shaft section, and optionally an increasing pitch section, to ensure reliable flow of the feedstock.
  • a first double dump valve or rotary valve 1000 pressure isolation valve system is positioned at the discharge of the hopper 900 to allow for the controlled flow of solids to a lower pressure vessel. From the first double dump valve or rotary valve 1000, the treated feedstock is conveyed, e.g.
  • the heat transfer mechanism employed by the low- temperature evaporator 1100 may be direct (contact with heated gas), indirect (conductive contact with heated surfaces), radiant (no direct contact between the heated surface and solids), microwave, or any combination of these mechanisms.
  • the low-temperature evaporator 300 system illustrated in Figures 1 and 2, which employs direct, indirect, and radiant heat transfer mechanisms, may be employed as the low-temperature evaporator 1100 illustrated in Figure 3.
  • Variants or modified commercial solids drying processes such as thin-film, tray, vacuum paddle, and purge column dryers may also be used as a low-temperature evaporator system 1100.
  • the low-temperature evaporator 1100 is preferably maintained at a temperature of at least about 110 °C, and at atmospheric to sub-atmospheric pressures.
  • a gas circuit of the low-temperature evaporator 1100 is fitted with a first vacuum pump 1300 to provide a pressure differential for the flow of motive gas through the low-temperature evaporator 1100.
  • a blower 1500 When operating at atmospheric or higher pressures, a blower 1500 is placed upstream of the low-temperature evaporator 1100 to provide a driving force for the motive gas through the system. At a higher operating pressure, a recycle stream can be added to the motive gas circuit for the recovery of lean process gas and to reduce demand from gas production systems.
  • a heated motive gas is injected into the low-temperature evaporator 1100 through a first motive gas production module 1400 to assist in driving off moisture and lower- molecular weight volatile compounds having relatively low boiling points; these compounds may include monoterpenes and certain sesquiterpenes.
  • the temperature of gas from the first motive gas production module 1400 is preferably between about 120 °C and about 250 oC.
  • the motive gas preferably comprises a non-oxidizing gas, which may be selected from the group consisting of nitrogen, steam, helium, argon, an inert gas other than helium and argon, air, carbon dioxide, and steam.
  • a gas-generating utility such as a steam boiler or nitrogen generator (PSA- or membrane-based) may be included in the first motive gas production module 1400.
  • the pregnant motive gas containing moisture and the light terpenes exits the low-temperature evaporator 1100 through a gas exhaust port and is directed to a first vapor recovery unit 1200.
  • the first vapor recovery unit 1200 typically comprises a coiled tube-in-tube heat exchanger and/or a cold finger condenser, whereby water and volatile compounds are condensed. Additional coalescing, condensing, phase separation, and recovery techniques may also be employed, including but not limited to liquid-phase recovery, cyclone recovery, and demisting operations.
  • the motive gas and unrecoverable volatile products are pulled via the first vacuum pump 1300 out of the first vapor recovery unit 1200 and vented to the atmosphere or recycled back to the motive gas circuit.
  • the blower 1500 is placed upstream of the low-temperature evaporator 1100 to provide a driving force for motive gas through the system.
  • a high-temperature evaporator 320 as illustrated in Figure 1 may be employed as the high-temperature evaporator 1700 illustrated in Figure 3.
  • the high- temperature evaporator 1700 is comprised of a screw with a gas-permeable shaft, a gas- permeable cylindrical trough, and a gas-impermeable cylinder.
  • the gas-impermeable cylinder surrounds the gas-permeable cylindrical trough, and has a larger diameter that thereby forms an annular space between the gas-permeable cylindrical trough and the gas- impermeable cylinder.
  • the high-temperature evaporator 1700 may, in operation, be substantially and/or completely filled with feedstock material, or it may be partially filled, at least in a portion, by increasing the pitch of the screw. Lifters or paddles may be installed in appropriate portions of the high-temperature evaporator 1700 to promote mixing and movement of the feedstock.
  • the gas-permeable cylindrical trough constitutes an inner “shell” of, wherein the inner shell rotates on an auger.
  • Blades of the auger may be disposed on the inner shell, promoting motion of the feedstock through the high-temperature evaporator 1700.
  • the gas-impermeable cylinder thus constitutes the outer “shell” of the high-temperature evaporator 1700 to define the annular space within the high-temperature evaporator 1700, and may comprise a gas exhaust port, preferably near a longitudinal center of the high-temperature evaporator 1700, through which the motive gas and the extracted compounds exit the high-temperature evaporator 1700.
  • Motive gas is introduced into the high-temperature evaporator 1700 by a small-diameter gas dispersion membrane, which may be mounted to an auger to transport the motive gas through the high-temperature evaporator 1700, and a larger-diameter gas dispersion membrane may be positioned about the auger to provide cross-flow contact of the motive gas with the feedstock, thus allowing for pregnant motive gas containing the evaporated product materials may be collected in a void and/or annular space.
  • the high-temperature evaporator 1700 may comprise a gravity moving bed extractor, wherein the motive gas passes cross-currently between parallel gas-permeable plates, or variants or modified commercial vacuum solids drying processes such as vacuum paddle dryers and purge columns.
  • the high-temperature, low-pressure evaporator 1700 is maintained at sub- atmospheric pressure, preferably between about 0.02 inHg absolute and about 14 inHg absolute, and is heated and/or insulated to maintain a desired solids bed temperature, most typically between about 120 °C and about 200 °C.
  • a heated motive gas (also referred to as a stripping gas) is injected into the high-temperature evaporator 1700 and drawn through the high-temperature evaporator by a second vacuum pump 2200; the flow of the motive gas through the high-temperature evaporator 1700 may be any combination of co-current with, counter-current to, and/or cross-current to the flow of the feedstock through the high- temperature evaporator 1700, and may have any suitable flow rate sufficient to evaporate volatilizable compounds having a relatively high boiling point, e.g. THC and other cannabinoids, present in the feedstock.
  • the motive gas may be any suitable non-oxidizing gas, including but not limited to an inert gas (helium, argon, etc.), air, nitrogen, CO 2 , and superheated steam.
  • an inert gas helium, argon, etc.
  • air nitrogen
  • CO 2 carbon dioxide
  • superheated steam a gas that is produced by the high-temperature evaporator 1700.
  • the remnants of the feedstock e.g. dried and substantially completely devolatilized plant material (spent residue)
  • the motive gas for the high-temperature evaporator 1700 is generated, metered, and heated in a second motive gas production module 2000.
  • the module may comprise a boiler to produce superheated steam, a nitrogen gas generator, and/or a natural gas combustor to generate a gas mixture of CO 2 , nitrogen, and steam.
  • the motive gas is sent through a pressure let-down valve or orifice and heated to at least about 120 °C before introduction to the high-temperature evaporator 1700.
  • a non-condensable gas such as CO 2 or nitrogen
  • the gas may be recycled from the vacuum pump exhaust stream to reduce demand on the gas production operation.
  • process steam is condensed in the second vapor recovery module 2100, where the aqueous condensate is treated and recycled to the second motive gas production module 2000.
  • Pregnant process gas from the high-temperature evaporator 1700 containing steam, cannabinoids, sesquiterpenes, and noncondensable gases is directed to the second vapor recovery module 2100.
  • the second vapor recovery unit 2100 typically comprises a coiled tube-in-tube heat exchanger, whereby the condensable cannabinoids and terpenes and moisture are condensed. Additional coalescing, condensing, phase separation, scrubbers and recovery techniques may also be employed, including but not limited to liquid-phase recovery, cyclone recovery, and demisting operations.
  • the present inventors have found that the cannabinoids condense and coalesce directly on the surface of a tube-in-shell heat exchanger, and then drip by gravity into an extract collection chamber.
  • the raw oil thus produced can contain approximately 80 wt% cannabinoids when produced from a cannabinoid-rich feedstock.
  • the oil exhibits a “full-spectrum” quality, in which all cannabinoids present in the feedstock are present in similar ratios in the oil.
  • the oil is generally substantially free of chlorophyll and waxes.
  • the cannabinoid content of the raw oil can be increased by operating the high-temperature evaporator 1700 at full vacuum (i.e.
  • Noncondensable gases flow from the second vapor recovery unit 2100 collection system and to the second vacuum pump 2200. Exhaust from the second vacuum pump 2200 can be discharged to the atmosphere, treated with activated carbon, and/or flared to reduced emission particulate, mist, and odor.
  • Embodiments of the present invention may suitably be used to extract any one or more cannabinoids from cannabis or other plant material.
  • Cannabinoids amenable to extraction by embodiments of the present invention include, but are not limited to, cannabichromene-type (CBC) cannabinoids, e.g. ( ⁇ )-cannabichromene (CBC-C 5 ), ( ⁇ )- cannabichromenic acid A (CBCA-C 5 A), ( ⁇ )-cannabichromevarin (CBCV-C3), and ( ⁇ )- cannabichromevarinic acid A (CBCVA-C3 A); cannabichromanone-type (CBCN) cannabinoids, e.g.
  • CBC cannabichromene-type
  • CBC-C 5 cannabichromenic acid A
  • CBCV-C3 cannabichromevarin
  • CBCVA-C3 A cannabichromanone-type cannabinoids
  • cannabichromanone cannabichromanone-C 5
  • cannabichromanone-C 3 cannabichromanone-C 3
  • cannabicoumaronone cannabidiol-type (CBD) cannabinoids, e.g.
  • CBD-C 5 cannabidiol
  • CBD-C 4 cannabidiol monomethyl ether
  • CBD- C 4 cannabidiol-C4
  • CBD- C 4 cannabidiol-C 4
  • CBD- C 3 cannabidiorcol
  • CBD-C 1 cannabidiolic acid
  • CBDVA-C 3 cannabidivarinic acid
  • CBDVA-C 3 cannabielsoin-type (CBE) cannabinoids, e.g.
  • cannabigerol ((E)-CBG-C 5 ), cannabigerol monomethyl ether ((E)-CBGM-C 5 A), cannabinerolic acid A ((Z)-CBGA-C 5 A), cannabigerovarin ((E)-CBGV-C3), cannabigerolic acid A ((E)-CBGA-C 5 A), cannabigerolic acid A monomethyl ether ((E)-CBGAM-C 5 A), and cannabigerovarinic acid A ((E)-CBGVA-C 3 A); cannabicyclol-type (CBL) cannabinoids, e.g.
  • cannabinol CBN-C 5
  • cannabinol-C 4 CBN-C 4
  • cannabivarin CBN-C 3
  • cannabinol-C 2 CBN-C 2
  • cannabiorcol CBN-C 1
  • cannabinolic acid A CBNA-C 5 A
  • cannabinol methyl ether CBNM-C 5
  • cannabinodiol-type (CBND) cannabinoids e.g.
  • CBD cannabinodiol
  • CBD-C 3 cannabinodivarin
  • CBD cannabicitran-type or cannabitriol-type
  • cannabicitran CBT-C 5
  • (–)-(9R,10R)-trans-cannabitriol ((–)-trans-CBT-C 5 )
  • (+)-(9S,10S)-cannabitriol (+)-trans- CBT-C 5 )
  • ( ⁇ )-(9R,10S/9S,10R)-cannabitriol ( ⁇ )-cis-CBT-C 5 )
  • (–)-(9R,10R)-trans-10-O- ethyl cannabitriol ((–)-trans-CBT-OEt-C 5 ),
  • ( ⁇ )-(9R,10R/9S,10S)-cannabitriol-C 3 (( ⁇ )- trans-CBT-C3), 8,9-dihydroxy- ⁇ 6a(10a) -tetrahydrocannabinol (8,9-Di-OH-CBT-C 5 ), cannabidiolic acid
  • CBDA can
  • ⁇ 9 -tetrahydrocannabinol ( ⁇ 9 -THC- C5), ⁇ 9 -tetrahydrocannabinol-C4 ( ⁇ 9 -THC-C4), ⁇ 9 -tetrahydrocannabivarin ( ⁇ 9 -THCV-C3), ⁇ 9 -tetrahydrocannabiorcol ( ⁇ 9 -THCO-C1), ⁇ 9 -tetrahydrocannabinolic acid A ( ⁇ 9 -THCA- C5 A), ⁇ 9 -tetrahydrocannabinolic acid B ( ⁇ 9 -THCA-C 5 B), ⁇ 9 -tetrahydrocannabinolic acid- C 4 A and/or B ( ⁇ 9 -THCA-C 4 A and/or B), ⁇ 9 -tetrahydrocannabivarinic acid A ( ⁇ 9 -THCVA- C3 A), ⁇ 9 -tetrahydrocannabiorcolic acid A and
  • Embodiments of the present invention may suitably be used to extract any one or more terpenes and terpenoids from cannabis or other plant material.
  • Terpenes and terpenoids amenable to extraction by embodiments of the present invention include, but are not limited to, endo-borneol; ⁇ -carene; bornyl acetate; ⁇ -y GmbHe; ⁇ -copaene; aromadendrene; eremophilene; longifolene; ⁇ -guaiene; valencene; ⁇ -bisabolene; ⁇ -cadinene; ⁇ -selinene; neophytadiene; ferruginol; aristolone; ⁇ -amyrin; oleanane; ketoursene; ⁇ -amyrin; iridoids; iridoid glycosides; steroids, e.g.
  • campesterol ⁇ -sitosterol, ⁇ -sitosterol, stigmasterol, tocopherols, cholesterol, testosterone, cholecalciferol, and ecdysone
  • hemiterpenoids e.g. isoprene, prenol, and isovaleric acid
  • acyclic monoterpenes e.g. ocimene and myrcenes
  • monocyclic monoterpenes e.g. limonene, terpinene, phellandrene, and umbellulone
  • bicyclic monoterpenes e.g.
  • acyclic monoterpenoids e.g. linalool, citronellal, citral, citronellol, geraniol, and geranyl pyrophosphate
  • monocyclic monoterpenoids e.g. grapefruit mercaptan, menthol, p-cymene, thymol, perillyl alcohol, and carvacrol
  • bicyclic monoterpenoids e.g. camphor, borneol, eucalyptol, halomon, and ascaridole
  • sesquiterpenoids e.g.
  • farnesyl pyrophosphate, artemisinin, and bisabolol diterpenoids, e.g. geranylgeranyl pyrophosphate, gibberellin, retinol, retinal, phytol, taxol, forskolin, aphidicolin, and salvinorin A; sesterterpenoids, e.g. geranylfarnesol; non-steroidal triterpenoids, e.g. saponins, squalene, lanosterol, oleanolic acid, ursolic acid, betulinic acid, and moronic acid); sesquarterpenes and sesquarterpenoids, e.g.
  • carotenes e.g. ⁇ -carotene, ⁇ -carotene, ⁇ - carotene, ⁇ -carotene, lycopene, neurosporene, phytofluene, and phytoene
  • xanthophylls e.g. canthaxanthin, cryptoxanthin, zeaxanthin, astaxanthin, lutein, and rubixanthin
  • polyterpenoids norisoprenoids, e.g. 3-oxo- ⁇ -ionol, 7,8-dihydroionone, and precursors thereto; and activated isoprenes, e.g.
  • Example 1 Static Batch An extraction system according to the present invention comprised a heated column partially submerged in a hot oil bath allowing the flow of nitrogen gas through.
  • a thermocouple in the extraction system determined the temperature achieved by the feedstock as it was exposed to the gas during operation of the extraction system.
  • the feedstock a CBD-rich hemp material
  • Example 1 illustrates, a doubling of the absolute system pressure (from 1.5 inHg to 3.0 inHg) cannot be completely compensated for by a doubling of the extraction time (from 90 minutes to 180 minutes).
  • Example 2 Continuous Flow Crushed pelletized hemp plant material as the feed material was processed in a continuous agitated vessel; at a moisture content of 15%, the hemp plant material comprised 6.52 wt% CBD and 0.26 wt% THC. The feedstock was untreated before entering the agitator and heated at 170 oC for 60 minutes at 20 torr absolute to ensure all water and low boiling point volatiles had been removed from the feedstock.
  • the pressure was thereafter decreased to 2 torr absolute, and samples of the feedstock were retrieved at several intervals over a 120-minute period to examine the proportion of CBD still residing in the feedstock.
  • the results from this 120-minute period are illustrated in Figure 4.
  • Figure 4 illustrates, over 90% of the native CBD was removed from the hemp solids in the continuous process used for this Example.
  • the oil condensed in the extraction system was collected and its chemical composition quantified via GCMS.
  • the cannabinoid profile of the oil is presented in Table 2.
  • Example 2 Cannabinoid Profile of Oil from Continuous Extraction Process
  • the continuous process of Example 2 extracts the cannabinoids present in the plant material, exhibiting negligible fractionation between cannabinoids; a CBD:THC weight ratio in the extract product was about 23.7, similar to the ratio in the feedstock of about 25.1.
  • This Example thus illustrates that a high-cannabinoid product (80 wt% or higher) can be obtained from a cannabinoid-rich feedstock by the use of systems and methods of the present invention.
  • Example 3 Laboratory Scale System An extraction system as illustrated in Figure 1 was operated at a throughput rate of 100 pounds of plant material per day.
  • Table 3 Summary of Results from 100 lb/day System Results were analyzed from the feedstock exiting and collecting in the collection tank 400, recorded as a percentage of the cannabinoid no longer in the feedstock, and therefore inferred to have been stripped by the motive gas. As Example 3 illustrates, greater cannabinoid removal is generally associated with lower pressures. Runs that resulted in the highest cannabinoid removal rates tended to involve nearly absolute vacuum conditions at high temperatures, while runs with comparatively inhibited cannabinoid removal overall operated at higher pressures.
  • Example 4 Feedstock, Spent Feed, and Oil Comparisons Table 4 illustrates a comparison of the cannabinoid content of the THC-rich feedstock utilized in Example 3 and the cannabinoid content of the extract produced by the process of Example 3. Results were quantified by HPLC. Table 4: Comparison of Feedstock to Product As Example 4 illustrates, systems and methods of the present invention are effective to completely decarboxylate cannabinoids present in the feedstock; by way of non-limiting example, in the product, THC is present in the free/decarboxylated form in much greater amounts than in the feed material, whereas the quantity of the carboxylated THC-A is negligible.
  • the present inventors have unexpectedly found that the methods and systems of the present invention provide various advantages and benefits relative to the chemical extraction methods and systems of the prior art. Particularly, the methods and systems of the present invention are effective to continuously extract chemical compounds from a solid feedstock material at low pressures. To the best of the present inventors’ understanding, no currently existing method or system can achieve all of these advantages (continuous operation, solid feedstock, low pressure).
  • the invention illustratively disclosed herein suitably may be practiced in the absence of any element which is not specifically disclosed herein.

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Abstract

L'invention concerne de nouveaux processus d'évaporation thermique pour la récupération de constituants thermosensibles, de concentrés d'huile essentielle bruts, et d'autres composés à partir d'un matériau de biomasse végétale, ainsi que des systèmes pour mettre en oeuvre de tels processus En particulier, les procédés comprennent un processus exempt de solvant pour l'élimination par lots ou en continu et la récupération d'huiles raffinées, telles que des composants d'arômes volatils et des huiles lourdes, à partir de matière végétale.
PCT/US2019/065500 2019-12-10 2019-12-10 Systèmes, procédés, et équipement d'extraction chimique Ceased WO2021118539A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7622140B2 (en) * 2001-05-04 2009-11-24 Gw Pharma Limited Processes and apparatus for extraction of active substances and enriched extracts from natural products
US20160243460A1 (en) * 2015-02-19 2016-08-25 Biofract, Llc Thermal Fractionation Of Plant Material
US20180078874A1 (en) * 2015-04-03 2018-03-22 Natural Extraction Systems, LLC Method and apparatus for extracting botanical oils
US10428040B2 (en) * 2017-09-12 2019-10-01 Albert Jan DIJKSTRA Processes for the isolation of a cannabinoid extract and product from Cannabis plant material
US10456708B2 (en) * 2013-10-04 2019-10-29 Natural Extraction Systems, LLC Method and apparatus for extracting botanical oils

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7622140B2 (en) * 2001-05-04 2009-11-24 Gw Pharma Limited Processes and apparatus for extraction of active substances and enriched extracts from natural products
US10456708B2 (en) * 2013-10-04 2019-10-29 Natural Extraction Systems, LLC Method and apparatus for extracting botanical oils
US20160243460A1 (en) * 2015-02-19 2016-08-25 Biofract, Llc Thermal Fractionation Of Plant Material
US20180078874A1 (en) * 2015-04-03 2018-03-22 Natural Extraction Systems, LLC Method and apparatus for extracting botanical oils
US10428040B2 (en) * 2017-09-12 2019-10-01 Albert Jan DIJKSTRA Processes for the isolation of a cannabinoid extract and product from Cannabis plant material

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