WO2023043324A1 - Procédé d'extraction à partir de matière végétale et algale, et extraits obtenus à partir de celui-ci - Google Patents

Procédé d'extraction à partir de matière végétale et algale, et extraits obtenus à partir de celui-ci Download PDF

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WO2023043324A1
WO2023043324A1 PCT/NZ2022/050122 NZ2022050122W WO2023043324A1 WO 2023043324 A1 WO2023043324 A1 WO 2023043324A1 NZ 2022050122 W NZ2022050122 W NZ 2022050122W WO 2023043324 A1 WO2023043324 A1 WO 2023043324A1
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tetraalkylphosphonium
extraction
component
oil soluble
salt
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PCT/NZ2022/050122
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English (en)
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Luke Valentine Schneider
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Natural Extraction Technologies Limited
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Publication of WO2023043324A1 publication Critical patent/WO2023043324A1/fr

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    • 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
    • C11B1/00—Production of fats or fatty oils from raw materials
    • C11B1/02—Pretreatment
    • C11B1/04—Pretreatment of vegetable raw material
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
    • 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
    • C11B1/00—Production of fats or fatty oils from raw materials
    • C11B1/02—Pretreatment
    • 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
    • C11B1/00—Production of fats or fatty oils from raw materials
    • C11B1/10—Production of fats or fatty oils from raw materials by extracting
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
    • C11C1/007—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids using organic solvents

Definitions

  • the present invention relates to methods for extracting a lipidic component and/or oil soluble component from plant or algal material.
  • the present invention also relates to such a lipidic component and/or oil soluble component extracted from plant or algal material.
  • the lipids of plant and algal tissues are being used as sources for biodiesel fuels and dietary supplements.
  • the lipid and fatty acid content in most leafy plants and algae are high because of the thylakoid membrane of the chloroplasts. They represent an excellent replacement for fossil fuels because they are produced using sunlight as the energy source and both sequester atmospheric carbon dioxide and produce oxygen in the process.
  • the oils of plants are also typically lower in sulfur and nitrogen than fossil fuels, hence are considered clean burning.
  • Plant and algal tissues are also rich in polyunsaturated oils (e.g., omega-3 and omega-6 fatty acids) and oil-soluble secondary metabolites such as astaxanthins and zeoxanthins which are taken as antioxidant dietary supplements to promote joint health and reduce inflammation, and added to feed to impart a pink color to the flesh of farmed fish [Guerin et al. (2003)].
  • Anthocyanin and lycopene are oil-soluble pigmented phenolic plant compounds used to enhance the immune system, inhibit macular degeneration, and to promote heart health [Ghosh and Konishi (2007)]. All of these polyunsaturated compounds are considered essential nutrients for animals and humans since they are sourced primarily through the animal's diet, not synthesized directly by animal tissues. The low extraction yields of these materials from plant and algal tissues means that there is a lot of associated agricultural waste from the production of these dietary supplement ingredients.
  • the primary challenge has been recovering the oils from these tissues.
  • the extraction of oils and other components from algal and plant cells is typically low because of the polysaccharide rich cell walls that surround the contents of the plant cells and membranes. These are typically insoluble and crosslinked polysaccharide materials and often absorb and inhibit the diffusion of oils and oil-soluble compounds through the cell walls. These cell walls also prevent organic extraction solvents from entering the cell to dissolve and extract organically-soluble materials (e.g., lipids and fatty acids).
  • oils are extracted by pressing seeds and nuts (e.g., rape seed, linseed, sunflower seeds, hemp seed, peanuts, and olives) where the oil concentrations are sufficient enough to be free flowing when the pulp containing it is pressed with sufficient force.
  • seeds and nuts e.g., rape seed, linseed, sunflower seeds, hemp seed, peanuts, and olives
  • oils are uniquely used in the seeds and nuts of plants as an high density energy storage vehicle to support the germination of the seed germ.
  • Folch et al. (1951) developed a solid/liquid extraction method to recover lipids and fatty acids along with other oil-soluble materials from animal brains involving homogenizing the tissue in a single phase in a 2:1 chloroforr methanol solution, filtering the solids from the solution, then breaking the solution into two phases by the addition of additional water containing salts. Later work [Folch, et al. (1957)] showed that the salt type and concentration affected the lipid recovery and extended the technique to liver and animal mussel tissues. Reported lipid yields, however, never exceeded 38.5% and varied considerably by tissue type. Bligh and Dyer (1959) adapted and optimized this method for oil recovery from other animal tissues, particularly fish and marine animals.
  • the Bligh and Dyer method was similarly based on solid-liquid extraction, in which the animal tissues to be extracted where first macerated into small pieces in a monophasic solution of chloroform, methanol, and water (initial extraction). Sufficient methanol was used to draw the normally immiscible chloroform and water into a single combined phase. After a period of time, additional chloroform and/or water was added to the monophasic extraction solvent to dilute the methanol forcing a phase separation. The oils were recovered in the chloroform phase. Their inability to extract additional oil with a second extraction caused them to speculate that they had achieved complete (or near complete recovery).
  • Solvent extraction remained the industry standard although different water-immiscible extraction solvents were substituted over time, such as hexane for chloroform and ethanol for methanol, because of the toxicity of chloroform.
  • the intrinsic problem was dealing with the water presented by working with raw tissues. Oils and water don't mix, so a cosolvent that would allow an oil dissolving phase to intermix with the water in the tissue was necessary to aid the release and solubilization of tissue-embedded lipids into the liquid phase for extraction.
  • Refined fossil fuel hydrocarbons are typically used to extract the oils from dried algae and plants for biodiesel production, since the end goal of biodiesel production is the combustion value of the oil and the natural oils can merely be left in the hydrocarbons for this purpose.
  • Ethanol is now more typically used for dietary supplement oil extraction since it is more easily removed from the final dietary supplement product by evaporation and it is intrinsically food safe. This is still a solid/liquid extraction process, and, as such, the size of the dried tissue particle directly effects the lipid recovery, which means the best extraction efficiency is obtained from the finest powdered solids.
  • Supercritical fluids are now often used as alternative extraction solvents for dried or freeze-dried plant tissues [Catchpole et al. 2018)]. Unlike ethanol which must be thermally- evaporated, sometimes causing thermal damage to the nutrient value or market appeal of polyunsaturated oils, oil extraction by supercritical carbon dioxide can be recovered cold and instantaneously by releasing the pressure, evaporating the supercritical fluid and leaving droplets of oil to be collected. However, the extraction efficiency of supercritical CO 2 (scCO 2 ) was low (below 50%) [Catchpole et al. (2018)] because only the neutral lipids (triglycerides) were recovered.
  • the major challenge in both wet tissue and dried tissue extraction is the ability of a lipid-compatible solvent to penetrate the solid matrix.
  • Lipids are naturally hydrophobic and are effectively insoluble in water.
  • the large amounts of water inside of animal tissues prevent the lipid-compatible, water- immiscible solvents from penetrating the wet tissue particle, inhibiting lipid extraction.
  • the tissues are dried or freeze-dried, the lipids become encased in a hard proteinaceous or polysaccharide matrix that is difficult for solvents to penetrate and create a tortuous diffusional path to get the lipids back out of the solid particles once they are dispersed.
  • this method does nothing to remove the polysaccharide cell walls of algae and plants.
  • Xylanase and cellulase enzymes have been applied to reduce the polysaccharides of woody tissues into their constitutive sugars [Srivastava et al. (2016)], which can be subsequently fermented to produce biofuels (e.g., methane by anaerobic bacteria, and lipid membranes in aerobic bacteria).
  • biofuels e.g., methane by anaerobic bacteria, and lipid membranes in aerobic bacteria.
  • this approach is very inefficient for digesting woody tissues since the saccharase enzymes typically work from the outside in as they can't efficiently penetrate the cellulose fibers of the cell wall.
  • a known advantage of liquid/liquid extractions is that the higher the intensity of mixing (higher shear) reduces the diffusional path and increases the efficiency and rate of mass transport between the aqueous and solvent-rich phases. This does not happen in solid/liquid extraction where the diameter of the solid particle determines the rate and efficiency of mass transport.
  • N 2 O 4 is a strong oxidizing agent spontaneously generating hydroxyl radicals in the presence of water, which is again damaging to the polyunsaturated materials [Gert et al. (1993)].
  • the effect of N 2 O 4 on cellulose is the production of soluble nitrocellulosic materials (gun cotton), which is explosive, when dried.
  • N-methylmorpholine- N-oxide (NMMO) is a milder oxidizing agent than N 2 O 4 that operates through a reversible physical solubilization process [Lang et al. (1986)].
  • organic solvent may refer to a solvent consisting of a single entity (such as chloroform), or may refer to a solvent consisting of a plurality of entities - namely a solvent system such as a mixture of trichloroethylene and dichloromethane, and even mixtures of components such as oils, such as food grade oil.
  • alkylphosphonium typically tetraalkylphosphonium
  • alkylammonium typically tetraalkylammonium salts
  • hydroxides and other strong bases such as hydroxides and other strong bases
  • lipidic component and/or oil soluble component extraction efficiencies increase with the concentration of the tetraalkylphosphonium and tetraalkylammonium ions above 15% by weight in the aqueous phase with maximum extraction efficiencies peaking near 20%, and declining as concentration of the tetraalkylphosphonium and tetraalkylammonium ions exceed 35% by weight in the aqueous solution.
  • the tetraalkylphosphonium and tetraalkylammonium ions are present at a concentration of no more than about 50% by weight in the aqueous solution.
  • tetraalkylphosphonium and tetraalkylammonium ions that may be suitable for use in the present invention include tetramethylammonium, tetraethylammonium, tetrapropylammonium, benzyltrimethylammonium, tetrabutylammonium, tributylmethylphosphonium, tetrabutylphosphonium, and trioctylmethylphosphonium ions.
  • the preferred tetraalkylphosphonium and tetraalkylammonium ions are tetrabutylphosphonium and tetrabutylammonium ions.
  • counterions examples include hydroxide, fluoride, chloride, bromide, iodide, acetate, propionate, glycolate, oxalate, chloroacetate, formate, phosphate, hydrogen phosphate, dihydrogen phosphate, sulfate, nitrate, hydrogen sulfate, nitrite, thiosulfate, sulfite.
  • the tetraalkylphosphonium and tetraalkylammonium salts include hydroxide or acetate counterions.
  • the acetate salts can be synthesized by mixing the tetraalkylphosphonium or tetraalkylammonium hydroxide salt with acetic acid (such as a 40-60% aqueous acetic acid solution).
  • acetic acid such as a 40-60% aqueous acetic acid solution.
  • Tetraalkylphosphonium salts are believed to be more thermally stable than tetraalkylammonium salts, and are therefore preferred since they can be more readily recovered and recycled in the overall process.
  • the present invention uses a tetraalkylphosphonium or tetraalkylammonium salt which: i) Is provided wherein the counterion is a hydroxide or other strong base; and/or ii) Is provided at a concentration of no more than about 50% by weight in the aqueous solution.
  • the present invention uses a tetraalkylphosphonium or tetraalkylammonium salt which: i) Is provided wherein the counterion is a hydroxide or other strong base; and ii) Is provided at a concentration of no more than about 50% by weight in the aqueous solution.
  • the tetralkylphosphonium or tetraalkylammonium salts may be added directly to the harvested wet plant or algal material in proportion to the water content of the solid biomass (of the plant or algal material) to attain the desired aqueous phase concentration.
  • an aqueous solution containing tetraalkylphosphonium or tetraalkylammonium ions can be added to the tissues in a sufficient quantity to promote mixing of the tissues and solubilization of the polysaccharides present.
  • the step of mixing the plant or algal material with a tetraalkylphosphonium or tetraalkylammonium salt in the presence of water to form a mixture is conducted prior to a separate discrete step of adding the organic solvent to perform the extraction step.
  • the organic solvent is added at the same time that the plant or algal material is mixed with a tetraalkylphosphonium or tetraalkylammonium salt in the presence of water to form a mixture.
  • solvents examples include: chlorinated solvents (such as chloroform, dichloromethane, carbon tetrachloride, 1,2- dichloroethane, chlorobenzene, trichloroethylene, perchloroethylene (tetrachloroethylene)); hydrocarbon solvents (such as cyclohexane, cyclohexene, benzene, toluene, butane, isobutane, pentane, isopentane, neopentane, hexane, 2-methylp
  • plant or algal proteins that may be present may remain undigested in their natural intact composition. Such proteins may then be recovered (such as by chromatography, fractional precipitation, or immunoaffinity enrichment) from the de-lipidated tetraalkylphosphonium or tetraalkylammonium salt solution. This allows the production of a second useful product from the original plant or algal tissue, such as rubisco protein, which is a vegan alternative to egg whites.
  • the present invention can be applied to algae and microalgae species such as Chlorella sp.
  • the present invention can be applied to seaweeds, such as Pyropia sp.
  • the present invention can be applied to the leaves of terrestrial vining plants, such as Vitis sp.
  • the present invention can be applied to leaves of grasses, such as Triticum sp.
  • the present invention can be applied to leafy shrubs, such as Nicotiana sp. or Lactuca sp.
  • the present invention can be applied to the leaves of root vegetables, such as Colocasia esculenta or Beta sp.
  • the present invention can be applied to the leaves of trees, such as Maias domestica or Pranas dalcis.
  • the present invention can be applied to the skins of fruits and berries, such as Sambucus sp.
  • the present invention can be applied to the stamen and pedals of flowers, such as Echinacea purpurea.
  • FIG. 1 Gas chromatogram of US National Institute of Standards SRM 3275 samples used to identify the polyunsaturated fatty acid methyl ester peaks.
  • the lipid extract is prepared from algal or plant tissues that have been substantially dissolved in an aqueous tetraalkylphosphonium or tetraalkylammonium solution and the subsequent recovery of the lipid and oil-soluble fraction by extraction with a water- immiscible solvent or oil.
  • the hydrated plant tissues may be fresh or frozen with woody stems attached, is subjected to dissolution by mixing a sufficient amount of tetraalkylphosphonium or tetraalkylammonium ions added to the natural water content of the soft tissues to reach a final concentration of above 25% weight-to-volume and preferably above 15%. With the optimal tetraalkylphosphonium or tetraalkylammonium ion concentration being between 15-30% weight-to-volume.
  • the acetic acid is mixed with the plant tissue and any associated woody stems, dissolving the softer primary photosynthetic tissues in this process.
  • the insoluble materials, such as the woody stems may optionally be filtered from the remainder of the solubilized tissue solution.
  • a sufficient amount of aqueous tetraalkylphosphonium or tetraalkylammonium ions may be added to previously dried, freeze-dried, wilted or otherwise inadequately-hydrated plant or algal tissue to both rehydrate and solubilize the tissue.
  • the tetraalkylphosphonium or tetraalkylammonium ions may be pre-mixed in the proper ratio before contacting the tissue.
  • the water may be contacted first with the tissue, subsequently adding concentrated tetraalkylphosphonium or tetraalkylammonium salts to the proper ratio. The mixture is mixed to homogenize the solution and dissolve the tissues. Insoluble materials, such as woody stems, may optionally be filtered from the remainder of the solubilized tissue solution.
  • the ratio of aqueous tetraalkylphosphonium or tetraalkylammonium solution to plant tissues should be sufficient to allow mixing to occur. Otherwise, the higher the tissue solids content the better. In one embodiment the solids content can be maximized using an extruder for mixing. Lower solids contents can be processed by tumble mixers and tank-based agitators. The lower the volume of the aqueous phase tissue solution the higher the extraction efficiency that can be obtained.
  • a volume of an immiscible organic phase can be added to extract the lipidic component and/or oil soluble component in the plant or algal material.
  • organic solvents and oils can be used for the extraction process.
  • the choice of organic solvent can be optimized on the basis of Hansen solubility parameters. Hansen parameters are thermodynamic state properties of the organic solvent and measured values for many solvents are available in the literature [including Barton (1991) and Abbott et al. (2008) the entire contents of which are hereby incorporated herein by reference]. In addition to measured/known values for certain organic solvents, the Hansen parameters can be estimated using group contribution methods [Barton (1991)] for those other solvents whose solubility parameters have not been measured.
  • chloroform is an ideal solvent to optimise extraction.
  • R Euclidean distance
  • 6ds Hansen dispersive parameter for the solvent or solvent blend.
  • 6hs Hansen hydrogen-bonding parameter for the solvent or solvent blend.
  • Hansen solubility parameter values for miscible mixtures can be determined from the volumefraction average for each parameter [Schneider (1991)]. This principle enables the use of homogeneous solvent mixtures to mimic the behavior of other solvents by adjusting the volume fractions of the solvent mixture to match the solubility parameters of the target solvent. This technique can be used to swap extraction solvents based to lower cost, toxicity, increase volatility or otherwise enhance downstream separation from the extracted solute.
  • 6j refers to an individual Hansen solubility parameter (dispersive, polar, or hydrogen-bonding).
  • i the individual solvents comprising the miscible mixture.
  • the ratio of organic solvent to the tetraalkylphosphonium or tetraalkylammonium ions, and plant or algal material, can be adjusted to that sufficient for the level of recovery desired.
  • the lipidic component and/or oil soluble component will equilibrate between the organic-rich and aqueous ionic salt phases based on their phase equilibrium constant (Hn P id), which relates the lipid concentration in the aqueous phase (C a eq ) to that in the organic phase (C o e ⁇ 7 ) at equilibrium. This equilibrium constant is a property of the organic phase.
  • Hlipid Ysi
  • the maximum concentration of lipid that can be reached in the organic phase (C o eq ) can be determined from the initial concentration of lipid (C,) in the tetraalkylphosphonium or tetraalkylammonium ions and tissue homogenate as a function of Hn pi d and the volumes of aqueous (14) and organic (14) phases.
  • the maximum lipid yield (Yn P id) is determined from the aqueous to organic volume ratio and the equilibrium constant [Hn P id ⁇ for the water-immiscible organic solvents chosen for the extraction. Hu pid varying inversely the Euclidean distance of the organic solvent from chloroform.
  • SAdrop the average surface area of a droplet in the discontinuous (included) phase.
  • an organic solvent including: the ability to separate the lipidic component and/or oil soluble component extracted from the organic solvent by evaporation, chromatography, winterization, affinity enrichment, precipitation, or zone recrystallization.
  • the extraction can be operated under pressure so that a low boiling point organic solvent (such as (liquid) butane or propane) can be used as the extraction solvent. When the pressure is released the butane and propane will vaporize and the lipid recovered.
  • the extraction can be performed with lauric acid as the extraction solvent at 45 °C. By then lowering the temperature below 44 °C, the lauric acid can be slowly solidified by winterization, leaving the lower melting lipids as a liquid.
  • any fatty acid that remains in the liquid state at the processing temperature can be separated by anion exchange chromatography from the extracted neutral lipids it contains.
  • the above process can be operated at any temperature above the freezing point of the aqueous and or organic phases, whichever is higher (approximately 0-10 °C) and the temperature at which the desired lipidic component and/or oil soluble component decomposes.
  • a temperature at which the desired lipidic component and/or oil soluble component decomposes For polyunsaturated fatty acids decomposition starts to occur at 45 °C.
  • Another advantage of this process is that it operates at ambient temperatures and pressures, so requires no heat or refrigeration.
  • the tetraalkylphosphonium and tetraalkylammonium salts are known anti-microbial agents [Melezhyk et al. (2015) and Kanazawa et al. (1994)].
  • organic solvents and oils also do not support microbial growth.
  • the products, both lipidic component and/or oil soluble component and residual protein are protected from microbial contamination and digestion during processing.
  • the 1.5 mL of the resulting aqueous mixture was transferred to a 15 mL centrifuge tube and an equal volume of chloroform was added to the mixture to extract the lipids.
  • the tubes were sealed and put on an end-over-end rotary mixer for 24 hr to accomplish the extraction.
  • the 10% TBPOH was not observed to form a second lipid-rich chloroform phase.
  • the 20%, 30%, and 40% TBPOH solutions all formed two phases.
  • the mixed phases in example 2 were separated by centrifugation and samples of each phase recovered for fatty acid analysis.
  • 0.2 mL of aqueous and organic layers were added separately into respective 15 mL centrifuge tubes by transfer pipette.
  • Toluene (0.2 mL), 1.5 mL of methanol, and 0.3 mL of methanolic HCI (8% w/v) were added into each of the samples sequentially.
  • Example 4 Each tube was vortexed for 10 seconds to mix to homogeneity and incubated at 45 °C for 20 hours to both saponify the lipids and convert the resulting fatty acids into their corresponding methyl esters following the method of Ichihara and Fukubayashi (2010). The samples were again centrifuged to remove any particulates transferred to a glass gas chromatography vial and capped with a rubber gasket.
  • Example 4
  • a three-sample set of Omega-3 and Omega-6 fatty Acids in Fish Oil acid methyl ester standard mixture (US National Institute of Standards, SRM 3275) was used to identify the components in the samples prepared in example 5.
  • a 0.1 mL sample from each standard was diluted in 1 mL of a 30% methanol/70% toluene mixture.
  • a 0.25 mL sample of this dilution was then transferred into 1.13 mL of methylation buffer (Example 4).
  • the samples were capped, mixed and incubated for 16 hours at 45 °C in a heating block.
  • the samples were centrifuged to remove any particulates transferred to a glass gas chromatography vial and capped with a rubber gasket.
  • the methylated fatty acid contents of the saponified and methylated fatty acid samples prepared in examples 3 and 4 were analyzed on a Shimadzu GC-2014 gas chromatograph equipped with a 30 m Restek Stabiwax capillary column (0.25 mm ID, 0.25 micron film thickness) using a flame ionization detector (FID).
  • the injection volume was 1 pL using a split injector at 220 °C with a split ratio of 1:186 using hydrogen at 50 cm/s as the carrier gas.
  • the FID was operated at 250 °C.
  • the column was operated with a temperature gradient consisting of 160 °C for 1 min.
  • Example 5 Individual methylated fatty acid peaks in the samples from example 5 were identified by comparison to the elution times of the FAME standards (example 6). The identities of each of the polyunsaturated (omega-3 and omega-6) fatty acid methyl ester peaks in the standards were determined from the reported abundances and approximate elution times of each fatty acid methyl ester on the certificate of analysis ( Figure 1 and Table 2). Only the polyunsaturated fatty acids (omega-3 and omega-6) were tracked as these are the molecules that imparted the known clinical utility.
  • Fatty acid methyl esters were identified by their elution times by comparison to NIST 3275 Fish Oil standards run on the same column (Example 5). The abundances of each identified FAME were determined relative to baseline for each identified FAME. Since the volumes of the organic and aqueous phases were equal in the extraction, the yield of each FAME was calculated as the peak area of the FAME in the organic phase divided by the sum of the peak areas in both phases. The phase equilibrium constant was calculated as the ratio of the peak area in the organic phase to that in the aqueous phase sample. The Yields and Equilibrium constants for each experiment are shown in Tables 3-5. These data were determined from the averages of replicate experiments.
  • Table 3 Algal oil recovery by room temperature chloroform extraction from 20% TBPOH solubilized dried Chlorella vulgaris.
  • Table 4 Algal oil recovery by room temperature chloroform extraction from 30% TBPOH solubilized dried Chlorella vulgaris.
  • the invention may also be said broadly to consist in the parts, elements and features referred to or indicated in the specification of the application, individually or collectively, in any or all combinations of two or more of said parts, elements or features.

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Abstract

La présente invention concerne des procédés d'extraction d'un composant lipidique et/ou d'un composant soluble dans l'huile à partir d'une matière végétale ou algale. La présente invention concerne également un tel composant lipidique et/ou composant liposoluble extrait d'une matière végétale ou algale.
PCT/NZ2022/050122 2021-09-15 2022-09-08 Procédé d'extraction à partir de matière végétale et algale, et extraits obtenus à partir de celui-ci WO2023043324A1 (fr)

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US8598378B2 (en) * 2008-03-14 2013-12-03 University Of Hawaii Methods and compositions for extraction and transesterification of biomass components
WO2013192572A1 (fr) * 2012-06-22 2013-12-27 Suganit Systems, Inc Procédé et appareil de traitement de substrats de biomasse
WO2017091781A1 (fr) * 2015-11-24 2017-06-01 Sandia Corporation Liquides ioniques à base d'ammonium utiles pour un traitement de matières lignocellulosiques
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ZHANG YUJIE, WARD VALERIE, DENNIS DOROTHY, PLECHKOVA NATALIA, ARMENTA ROBERTO, REHMANN LARS: "Efficient Extraction of a Docosahexaenoic Acid (DHA)-Rich Lipid Fraction from Thraustochytrium sp. Using Ionic Liquids", MATERIALS, vol. 11, no. 10, 15 October 2018 (2018-10-15), pages 1986, XP093049719, DOI: 10.3390/ma11101986 *

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