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WO2019092013A1 - Procédé d'extraction d'acides gras à partir d'huiles triglycéridiques - Google Patents

Procédé d'extraction d'acides gras à partir d'huiles triglycéridiques Download PDF

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Publication number
WO2019092013A1
WO2019092013A1 PCT/EP2018/080464 EP2018080464W WO2019092013A1 WO 2019092013 A1 WO2019092013 A1 WO 2019092013A1 EP 2018080464 W EP2018080464 W EP 2018080464W WO 2019092013 A1 WO2019092013 A1 WO 2019092013A1
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WO
WIPO (PCT)
Prior art keywords
oil
phase
fatty acids
aqueous phase
triglyceride
Prior art date
Application number
PCT/EP2018/080464
Other languages
German (de)
English (en)
Inventor
Jennifer HEYMANN
Benjamin Willy
Matthias Bahlmann
Christian BRAMSIEPE
Jörg ZÖLLNER
Original Assignee
Evonik Degussa Gmbh
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
Application filed by Evonik Degussa Gmbh filed Critical Evonik Degussa Gmbh
Publication of WO2019092013A1 publication Critical patent/WO2019092013A1/fr

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Classifications

    • 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
    • C11B3/00—Refining fats or fatty oils
    • C11B3/02—Refining fats or fatty oils by chemical reaction
    • C11B3/04—Refining fats or fatty oils by chemical reaction with acids
    • 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
    • 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
    • C11B3/00—Refining fats or fatty oils
    • C11B3/001—Refining fats or fatty oils by a combination of two or more of the means hereafter
    • 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
    • C11B3/00—Refining fats or fatty oils
    • C11B3/006—Refining fats or fatty oils by extraction
    • 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
    • C11B3/00—Refining fats or fatty oils
    • C11B3/02—Refining fats or fatty oils by chemical reaction
    • C11B3/06—Refining fats or fatty oils by chemical reaction with bases
    • 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
    • C11B3/00—Refining fats or fatty oils
    • C11B3/12—Refining fats or fatty oils by distillation
    • C11B3/14—Refining fats or fatty oils by distillation with the use of indifferent gases or vapours, e.g. steam

Definitions

  • the invention relates to an improved process for the extraction of fatty acids from triglyceride oils.
  • (Earth) alkali metal hydrogencarbonates carried out.
  • the inventive method is characterized by a particularly gentle treatment of triglyceride oils and a lower
  • Natural fats and oils have various undesirable components, such as metals, free fatty acids and phospholipids, and therefore need to be refined. In the refining of natural fats and oils is thereby between the physical and the chemical
  • soapstocks In chemical refining, which is mainly used for triglyceride oils with a low content of free fatty acids, the free fatty acids are separated by reaction with a base. This produces Soapstocks, an aqueous mixture of base, free fatty acids, the salts of free fatty acids and oil. These soapstocks are an undesirable by-product of chemical refining of low value and limited use.
  • WO 2016/149692 A1 describes the acidification of aqueous solutions consisting of
  • Saponification reactions are derived and contain lipids.
  • the lipid-containing raw material is mixed with base (especially sodium or potassium hydroxide) and saponified. Subsequently, C ⁇ 2 is pressed, this reacts with the reaction mixture and the aqueous phase is removed.
  • base especially sodium or potassium hydroxide
  • C ⁇ 2 is pressed, this reacts with the reaction mixture and the aqueous phase is removed.
  • CN 106281672 A describes the treatment of triglyceride oils with antioxidants
  • WO 2015/031857 A2 describes the workup of soap-containing solutions with CO2 at a temperature between 0 ° C and 50 ° C, whereby the soaps are converted into free fatty acids.
  • DE 196 38 459 A1 describes a process for the purification of vegetable or animal fats or oils, in which the fat or oil to be purified is extracted with polyethylene glycol.
  • WO 2012/035020 A1 and GB 1 520 523 A describe processes for the extraction of fatty acids from vegetable oils, in which polyols are used in combination with bases as extractants.
  • WO 2015/185657 A1 describes a process for working up an organic oil, in which it is first degummed by adding water and / or acid and then combined with sodium bicarbonate and / or sodium acetate.
  • WO 2016/189328 A1 describe the treatment of triglyceride oils with quaternary
  • Ammonium salts and their solutions for the removal of free fatty acids, metals and other undesirable components are desirable components.
  • a triglyceride oil is extracted with an aqueous solution of a basic quaternary ammonium salt in order to remove fatty acids therefrom. After extraction, the phases are separated. To regenerate the aqueous solution, which is necessary to use it in a new extraction step of the process, this aqueous, loaded with fatty acid salts of the triglyceride oil phase is pressurized with CO2.
  • WO 2016/189114 A1 discloses a reliable process for the extraction of free fatty acids from triglyceride oils, this has a problem especially in large-scale applications.
  • the aqueous phase used for the extraction (comprising the quaternary ammonium salts) can be regenerated by applying CO2.
  • the inventors of the present applications have found that the use of this so-regenerated aqueous phase to a foul odor and sometimes dark Deposits in the oil treated with it. This causes a significant reduction in the quality of the extracted oil.
  • the process described in WO 2016/1891 14 A1 is poorly suited, especially for the industrial scale, where it is desirable to minimize the consumption of resources in the production of high-quality oils and to recycle waste streams.
  • quaternary ammonium salts are surface active and are often used as cationic surfactants in soaps and softeners. Their separation after the treatment of triglyceride oils is therefore technically very demanding, since they emulsify with water and oil and make the phase separation difficult.
  • the object of the present invention was therefore to provide a process for the extraction of fatty acids from triglyceride oils, which does not have the aforementioned disadvantages. Above all, a process should be provided which allows recycling of the phases while ensuring high quality of the extracted triglyceride oil.
  • the invention accordingly relates to a process for the extraction of fatty acids from triglyceride oils, comprising the following steps:
  • step (c) adding CO2 and optionally an organic solvent to the aqueous phase W2, whereby an aqueous phase W3 having a lower fatty acid content than W2 and a fatty acid-containing organic phase Fo are obtained; (d) separating the aqueous phase W3 from the fatty acid-containing organic phase Ph obtained in step (c);
  • an aqueous solution W1 of a salt S is selected the group consisting of alkaline earth metal bicarbonate, alkali metal bicarbonate, is used. If such a solution is used in step (a), this leads to an improved quality of the aqueous phase W3 obtained in step (c).
  • step (d) of the process according to the invention After completion of step (d) of the process according to the invention, a phase W3 is obtained which can be treated in a new cycle with a new batch of triglyceride oil.
  • the problems which have been observed when using an aqueous phase regenerated according to the prior art do not occur.
  • the sequence of the steps of the process according to the invention the aqueous phase obtained in step (d) can be used again for the extraction of new triglyceride oil comprising fatty acids in step (a) and not just to an odor of the extracted triglyceride oil leads, as is the case in the case of the method described in WO 2016/1891 14 A1.
  • aqueous phase W3 is contacted with further triglyceride oil T3 comprising fatty acids, whereby a
  • Triglyceride oil phase T 4 and an aqueous phase W 4 are obtained, wherein T 4 has a reduced content of fatty acids compared to T3 and W 4 has a relative to W3 increased content of fatty acids.
  • the salt S is selected according to the invention from the group consisting of
  • Alkaline earth metal bicarbonate alkali metal bicarbonate, and is preferably one
  • an alkali metal hydrogencarbonate is preferably selected from the group consisting of sodium bicarbonate, potassium bicarbonate, and more preferably is in the context of the invention in the alkali metal bicarbonate to
  • the most preferred salt S which is selected from the group consisting of alkaline earth metal bicarbonate, alkali metal bicarbonate, is potassium bicarbonate.
  • triglyceride oil includes any oil or fat whose main constituent is> 50% by weight of triglycerides
  • the oil or fat may also comprise mono- and diglycerides.
  • the triglyceride oil is preferably of natural origin and more preferably of animal or vegetable origin. More preferably, the triglyceride oil is a fat or oil of vegetable origin.
  • algae oil As fats and oils of plant origin come in particular into consideration (where appropriate in brackets Latin terms indicate the plant species from which the oil is obtained): algae oil, apricot kernel oil (Prunus armeniaca), argan oil (Argania spinosa), avocado oil (Persea americana) , Babassu oil (Attalea speciosa), cottonseed oil (Gossypium), borage oil (Moringa oleifera), borage oil (Borago officinalis), nettle seed oil (Urtica pilulifera or Urtica dioica), beech oil (Fagus), cashew peel oil (Anacardium
  • Occidentale oil from plants of the genus Citrus (for example lemon, orange, grapefruit, lime), Cupuagu butter (Theobroma grandiflorum), thistle oil (Carthamus), peanut oil (Arachis hypogaea), rosehip seed oil (Rosa), hemp oil (cannabis), Hazelnut oil (Corylus avellana), jatropha oil (Jatropha curcas), jojoba oil (Simmondsia chinensis), coffee bean oil (Coffea), cocoa butter (Theobroma cacao), camellia oil (Camellia), cabbage palm (Euterpe oleracea), coconut oil (Cocos nucifera), pumpkin seed oil (Cucurbita) , Camelina oil (Camelina sativa), linseed oil (Linum),
  • Corn oil (Zea mays), macadamia oil (Macadamia integrifolia, Macadamia tetraphylla), almond oil (Prunus dulcis), mango butter (Mangifera indica), corn oil (Zea mays), poppy seed oil (Papaver),
  • primrose oil (Oenothera biennis), olive oil (Olea europaea), palm oil (oil obtainable from a plant of the genus Elaeis, in particular Elaeis guineensis, Elaeis oleifera), papaya seed oil (Carica papaya), pecan nut oil (Carya illinoinensis), perilla oil (Perilla frutescens), pine nut oil
  • the fats and oils of vegetable origin are selected from coconut oil, corn oil, cottonseed oil, olive oil, palm oil, peanut oil, rice oil, soybean oil, sunflower oil, rapeseed oil, castor oil, thistle oil. Most preferably, the fat and oil of plant origin is palm oil.
  • fatty acids comprise saturated and monounsaturated or polyunsaturated fatty acids.Furthermore, this term according to the invention (unless otherwise specified in the specific case) always encompasses both the protonated and the deprotonated form of the respective fatty acid.
  • Examples of unsaturated fatty acids are myristoleic acid, palmitoleic acid, sapiens acid, oleic acid, elaidic acid, vaccenic acid, linoleic acid, linolelaidic acid, ⁇ -linolenic acid, arachidonic acid, eicosapentaenoic acid, erucic acid and docosahexaenoic acid.
  • Examples of saturated fatty acids are caprylic acid, capric acid, undecanoic acid, lauric acid, tridecanoic acid, myristic acid,
  • Palmitic acid margaric acid, stearic acid, nonadecanoic acid, arachic acid, heneicosanoic acid, behenic acid, lignoceric acid and cerotic acid.
  • Palm oil means an oil obtainable from a plant of the genus Elaeis (part of the palm family or palm trees Arecaceae or Palmae), in particular Elaeis guineensis, Elaeis oleifera or hybrids thereof, for example, the pulp of the pulp or the kernel be available to the plant.
  • the triglyceride oil in particular the palm oil used in step (a), may be unrefined or at least partially refined.
  • This also includes fractionated triglyceride oil, for example fractionated palm oil, in particular stearic acid fractions or oleic acid fractions of palm oil.
  • unrefined triglyceride oil means triglyceride oil which does not belong to anyone
  • Refining step was subjected.
  • unrefined triglyceride oil has not undergone any of the following refining steps: degumming, deacidification, bleaching, depigmentation, deodorization, winterization.
  • “Refined” triglyceride oil has undergone at least one refining step, for example at least one selected from degumming, deacidification, bleaching, depigmenting, deodorization, winterization.
  • step (a) of the process according to the invention a triglyceride oil Ti comprising fatty acids is contacted with an aqueous solution W 1 comprising at least one salt S selected from the group consisting of alkaline earth metal bicarbonate, alkali metal bicarbonate.
  • the temperature in step (a) of the process according to the invention is not limited further.
  • step (a) of the process according to the invention is carried out at a temperature ⁇ 100 ° C, preferably at a temperature of 25 ° C to 99 ° C, more preferably 40 ° C to 95 ° C, even more preferably 55 ° C to 90 ° ° C, more preferably at 70 ° C to 80 ° C.
  • step (a) of the process according to the invention is likewise not limited further.
  • step (a) of the process according to the invention is carried out at a pressure of from 1 bar to 100 bar, in particular at atmospheric pressure of 1 bar.
  • Alkaline earth metal hydrogen carbonate, alkali metal bicarbonate can take place by methods known in the art.
  • the contacting may take place in a vessel in which Ti and Wi are mixed together. It goes without saying that the contacting should take place in such a way that as many fatty acids as possible pass from the triglyceride oil Ti into the aqueous phase Wi.
  • a mechanical mixer such as a stirred tank, which can be operated non-continuously or continuously
  • an ultrasonic mixer an electromagnetic mixer used.
  • an inert gas can be blown through the resulting mixture.
  • Ti and Wi can also be mixed in a static mixer such as a Sulzer mixer or Kenics mixer.
  • the column may be a sieve tray column, a packed column or a stirred column, such as a Kühni column or a Scheibel column.
  • Trigylceride oil Ti is introduced at or at least near the bottom of the column and the aqueous solution Wi of at least one salt S selected from the group consisting of alkaline earth metal bicarbonate, alkali metal bicarbonate is introduced at or near the top of the column.
  • aqueous phase W2 which has a higher fatty acid content than Wi, is then removed at or near the bottom of the column, and a triglyceride oil phase T2 having a reduced fatty acid content relative to Ti is then added at or near the top Column dissipated.
  • the column also has a sump region in which a secondary stream can be collected, and more preferably the triglyceride oil Ti is then fed directly above this sump region.
  • a secondary stream can be collected, and more preferably the triglyceride oil Ti is then fed directly above this sump region.
  • several such countercurrent column can be used, for example 2 to 6, or 3 to 5 or 4.
  • the column also has a packing, for example a pack of Raschig rings or "trays".
  • step (a) of the process according to the invention is carried out in which Ti and Wi are mixed in cocurrent, more preferably in at least one mixer-settler.
  • the volume ratio of Ti and Wi in step (a) of the method is not further limited.
  • the ratio of the volume of the triglyceride oil Ti to the volume of the aqueous phase Wi is in particular in the range of 1: 1 to 1: 200, preferably 1: 2 to 1: 20, more preferably 1: 2.3 to 1: 10.
  • the mixing as for Example, the contacting in the column in the case of continuous contacting can be adjusted by the expert so that as much as possible of the fatty acids of the triglyceride oil phase Ti passes into the aqueous phase Wi.
  • the contact is therefore for example for 1 second to 2 hours, in particular 30 seconds to
  • 1 hour preferably 1 to 40 minutes, more preferably 5 to 20 minutes, most preferably 10 to 15 minutes.
  • the fatty acids comprised of triglyceride oil Ti which are not present as soaps, are selected in step (a) of the process according to the invention by the salts S comprised by the aqueous phase Wi selected from the group consisting of alkaline earth metal bicarbonate,
  • the molar amount of all salts S included in the aqueous phase Wi is selected from the group consisting of
  • the ratio of the molar amount of all salts S comprised by the aqueous phase Wi is preferably selected from the group consisting of alkaline earth metal bicarbonate, alkali metal hydrogencarbonate to the molar amount of all fatty acids comprised of triglyceride oil Ti in the range from 1: 1 to 300: 1, more preferably
  • the proportion of fatty acids in the triglyceride oil can be determined by methods known to those skilled in the art, for example by titration with potassium hydroxide and a Phenolphthalein. After determining the proportions of fatty acids in the triglyceride oil Ti, the expert then also knows how large the desired molar amount of all of the aqueous phase Wi comprised salts S selected from the group consisting of alkaline earth metal bicarbonate, alkali metal bicarbonate must be, which he can then adjust accordingly.
  • an aqueous phase Wi comprising at least one salt S selected from the group consisting of
  • Alkaline earth metal hydrogen carbonate alkali metal hydrogen carbonate used.
  • the aqueous solution may also comprise further solvents, for example acetone,
  • the aqueous phase Wi comprises, in addition to water, no further solvents, which according to the invention means that the proportion by weight of the sum of all salts S is selected from the group consisting of
  • the concentration of all salts S selected from the group consisting of
  • Alkaline earth metal hydrogencarbonate, alkali metal hydrogencarbonate in the aqueous phase Wi is not further limited and is preferably in the range of> 0.4 mol / L, more preferably 0.5 mol / L to 5.0 mol / L, even more preferably 0.5 mol / L to 4.0 mol / L, even more preferably 1.0 mol / L to 3.5 mol / L, much more preferably 2.0 mol / L to 3.0 mol / L.
  • a triglyceride oil phase T 2 and an aqueous phase W 2 are obtained, wherein T 2 has a reduced fatty acid content relative to Ti and W 2 has a higher fatty acid content than Wi.
  • step (b) of the process according to the invention the triglyceride oil phase T 2 is then separated from the aqueous phase W 2 .
  • This separation can also be carried out by methods known to the person skilled in the art, for example by means of gravity in a seeding unit.
  • the triglyceride oil phase T 2 is then separated from the aqueous phase W 2 .
  • the separation of the triglyceride oil phase T 2 from the aqueous phase W 2 can alternatively also be carried out in a decanter, a hydrocyclone, an electrostatic coalescer, a centrifuge or a membrane filter press. Preference is given in step (b) of In accordance with the invention, the triglyceride oil phase T2 is separated from the aqueous phase W2 in a centrifuge.
  • salt S selected from the group consisting of alkaline earth metal bicarbonate, alkali metal bicarbonate of W1 at least partially precipitate during contacting in step (a) and present as a solid in the triglyceride oil phase T2, it may also be separated by centrifugation or filtration. Solvent or water may also be added to the solid triglyceride oil phase T2 to solubilize the solid and separate the aqueous solution comprising the appropriate salt as described above.
  • the step (a) and the step (b) of the process according to the invention ie the contacting and separation in a centrifugal separator, as described for example in US 4,959,158, US 5,571,070, US 5,591,340, US 5,762,800, WO 99/12650 and WO 00/29120.
  • T1 and W1 are in particular supplied to the separator only as separate streams and mixed in an annular mixing zone. The mixture is then passed to the deposition zone, where the phases are then separated by means of a centrifuge.
  • one uses a series of centrifugal separators, for example 2 to 6, 3 to 5 or 4, and introduces the triglyceride oil T1 into the first separator of the series, and the aqueous phase W1 into the last separator in the series so that triglyceride oil decreases with decreasing Content of fatty acids passes through the first to last separator in the series, while the aqueous phase with increasing content of fatty acids passes through the separator in the opposite direction.
  • the aqueous phase W2 is then taken from the first separator, the triglyceride oil phase T2 from the last separator in the series.
  • the triglyceride oil phase T2 can also be fed to a coalescing filter in order to remove last drops of aqueous solution from the fat or oil phase.
  • a coalescing filter is known to the person skilled in the art and comprises, for example, a filter material which is wetted by the aqueous phase rather than by the oil phase, for example a glass or cellulose filter material.
  • the triglyceride oil phase T2 can then be sent for further processing.
  • a step may be one or more selected from degumming, deacidification, winterization, bleaching, depigmentation, deodorization.
  • the triglyceride oil phase T2 after the separation in step (b) can be fed once more or several times, for example twice to ten times, to a contacting step (a) in which the triglyceride oil phase T2 is used as triglyceride oil T1 and contacting each step with a new batch of aqueous phase W1 comprising salts S selected from the group consisting of alkaline earth metal bicarbonate, alkali metal bicarbonate, to further lower the level of fatty acids in the triglyceride oil phase T2.
  • aqueous phases W2 obtained in these additional steps can then be fed completely or partially to the subsequent step (c).
  • step essential for the invention is then step (c) of the invention
  • fatty acid-containing organic phase Fo means the phase which forms the second phase comprising free fatty acids in addition to the aqueous phase W3.
  • the content of fatty acids is increased compared to the content of fatty acids in W 2.
  • the phase Fo is already alone therefore "organic” because it includes free fatty acids. It may contain, in addition to the free fatty acids, an organic solvent, if this is added in step (c) of the
  • step (c) of the process according to the invention the phase Fo forms as a separate and separable in particular by centrifugation phase in addition to the aqueous phase W3, as shown in the inventive example 2.
  • the addition of an organic solvent in step (c) of the process according to the invention is preferred because it facilitates the separation of the fatty acid-containing organic phase Fo from the aqueous phase W3.
  • the contacting of the aqueous phase W2 with CO2 and optionally an organic solvent can take place by methods known to the person skilled in the art.
  • the contacting can take place in a gas-tight sealable pressure vessel in which W2 and CO2 and optionally an organic solvent are mixed together.
  • CO2 can be introduced, for example, via a capillary or a gasatable stirrer.
  • the contacting should take place so that as much CO2 in the aqueous Phase W2 is entered.
  • a mechanical mixer or an electromagnetic mixer is used.
  • step (c) of the process according to the invention If an organic solvent is added in step (c) of the process according to the invention, then the volume ratio of W 2 and the organic solvent in step (c) of
  • Procedure is not limited.
  • the ratio of the volume of W 2 to the volume of the organic solvent is then in particular in the range from 1: 100 to 100: 1, preferably 1: 5 to 5: 1, more preferably 1: 2 to 2: 1.
  • an organic solvent in step (c) it is preferably diisopropyl ether, n-butyl acetate, ethyl acetate, hexane, 1-hexanol, more preferably n-butyl acetate.
  • At least one salt S is selected from the group consisting of
  • Alkaline metal hydrogencarbonate, alkali metal bicarbonate is used in the aqueous phase, the disadvantages of the prior art, which result from the method of WO 2016/1891 14 A1, can be avoided. This is evidenced by the fact that when the aqueous solution is reused in later extraction steps with, for example, fresh triglyceride oil, the bad smell is absent.
  • the pressure and the temperature in step (c) of the method according to the invention are not limited further.
  • the pressure during the addition of the CO 2 is in a range of 0.1 to 55 bar, preferably 1 to 20 bar, more preferably 5 to 10 bar.
  • the temperature is preferably in the range of 0 ° C to 120 ° C, more preferably 5 ° C to 100 ° C, even more preferably 10 ° C to 90 ° C, even more preferably 20 ° C to 80 ° C, even more preferably 40 ° C to 60 ° C, most preferably 50 ° C.
  • the CO2 used in step (c) may come from a combustion process or
  • Blast furnace process may include other components such as N2O, SO2, H2S, NO2. These components can further acidify the aqueous phase W2, so that this further favors the formation of a fatty acid-containing organic phase Fo.
  • a fatty acid-containing organic phase Fo and an aqueous phase W3 which has a lower content of fatty acids than W2 are then obtained.
  • step (d) of the process according to the invention the aqueous phase W3 is separated off from the fatty acid-containing organic phase Fo obtained in step (c).
  • step (e) of the method according to the invention is preferably carried out as described for step (a).
  • the process according to the invention is suitable for recycling the aqueous phase W1 again and again and for use in a new extraction process.
  • the following examples are intended to illustrate the invention without limiting it.
  • Inventive Example 1 60 g of palm oil (5.5% by weight of free fatty acids, determined by titration according to DGF method DGF-CV 2, based on palmitic acid) were admixed with 154 g of a 3.0 molar aqueous solution of KHCO 3 and at 80 ° C. for 1 hour touched. After the reaction, the aqueous phase and the organic phase were separated by a centrifuge. The content of fatty acids in the obtained triglyceride phase was determined by titration to 0.34 wt .-%. This corresponds to a conversion of free fatty acids of 94.1%. The triglyceride phase exhibited the characteristic odor of crude palm oil. The aqueous phase was transferred to a reactor and combined with n-butyl acetate in a volume ratio of 1: 1. In the mixture CO2 was introduced and at a
  • the content of fatty acids in the obtained triglyceride phase was determined by titration to 0.40 wt .-%. This corresponds to a conversion of free fatty acids of 93.1%.
  • the triglyceride phase exhibited the characteristic odor of crude palm oil.
  • Triglyceride phase showed thereby the characteristic smell of the raw palm oil.
  • the aqueous salt solution was transferred to a reactor. After introduction of CO 2, this was stirred at 40 ° C. partial pressure of 25 bar for 1 hour. After cooling to room temperature, the CC pressure was released and the reaction solution was discharged into a glass. Here, a second almost solid phase was observed on the salt solution, which is free fatty acid.
  • This example shows that addition of an organic solvent is not necessarily necessary to ensure separation of the resulting fatty acid phase. A corresponding result is also to be expected when starting from an aqueous salt solution of potassium hydrogen carbonate.
  • the content of fatty acids in the obtained triglyceride phase was determined by titration to 0.18 wt .-%. This corresponds to a conversion of free fatty acids of 97.2%.
  • the triglyceride phase showed a pungent odor.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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Abstract

L'invention concerne un procédé amélioré d'extraction d'acides gras à partir d'huiles triglycéridiques. L'extraction de l'huile triglycéridique est effectuée à l'aide d'une solution aqueuse de carbonates d'hydrogène de métaux alcalins (terreux). Le procédé selon l'invention se caractérise par un traitement particulièrement précautionneux des huiles triglycéridiques et une moindre consommation de ressources.
PCT/EP2018/080464 2017-11-10 2018-11-07 Procédé d'extraction d'acides gras à partir d'huiles triglycéridiques WO2019092013A1 (fr)

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EP17201046 2017-11-10
EP17201046.4 2017-11-10

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WO2019092013A1 true WO2019092013A1 (fr) 2019-05-16

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WO1999012650A1 (fr) 1997-09-11 1999-03-18 Costner Industries Nevada, Inc. Rotor autonettoyant pour separateur centrifuge
WO2000029120A1 (fr) 1998-11-16 2000-05-25 Costner Industries Nevada, Inc. Ensemble rotor pour separateur centrifuge
WO2012031176A1 (fr) 2010-09-03 2012-03-08 Stepan Company Élimination des espèces organohalogénées et oxiranes dans les courants d'ester d'acide carboxylique
WO2012035020A1 (fr) 2010-09-13 2012-03-22 Palsgaard A/S Huile végétale raffinée et procédé pour la produire
WO2015031857A2 (fr) 2013-08-30 2015-03-05 Inventure Renewables, Inc. Procédés et procédés industriels de production d'acides gras libres et deux leurs dérivés associés à partir de pâtes de neutralisation
WO2015185657A1 (fr) 2014-06-05 2015-12-10 Gea Westfalia Separator Group Gmbh Procédé et dispositif de traitement par étapes d'une huile organique
WO2016149692A1 (fr) 2015-03-19 2016-09-22 Inventure Renewables, Inc. Saponification complète et acidulation de sous-produits de traitement d'huile naturelle et traitement de produits de réaction
WO2016189115A1 (fr) 2015-05-27 2016-12-01 Evonik Degussa Gmbh Procédé d'élimination du métal d'une huile glycéridique contenant un métal comportant un traitement au sel d'ammonium quaternaire basique
WO2016189114A1 (fr) 2015-05-27 2016-12-01 Evonik Degussa Gmbh Procédé de raffinage d'huile de glycéride comprenant un traitement au sel d'ammonium quaternaire basique
WO2016189328A1 (fr) 2015-05-27 2016-12-01 Green Lizard Technologies Ltd Procédé d'élimination de chloropropanols et/ou de glycidol, ou leurs esters d'acide gras, à partir d'huile de glycéride, et processus de raffinage d'huile de glycéride amélioré le comprenant
CN106281672A (zh) 2015-05-28 2017-01-04 丰益(上海)生物技术研发中心有限公司 一种降低油脂中三氯丙醇或其酯含量的方法

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