EP3483237A1 - Procédé d'extraction d'acides gras d'une huile glycéridique - Google Patents

Procédé d'extraction d'acides gras d'une huile glycéridique Download PDF

Info

Publication number
EP3483237A1
EP3483237A1 EP17201077.9A EP17201077A EP3483237A1 EP 3483237 A1 EP3483237 A1 EP 3483237A1 EP 17201077 A EP17201077 A EP 17201077A EP 3483237 A1 EP3483237 A1 EP 3483237A1
Authority
EP
European Patent Office
Prior art keywords
oil
quaternary ammonium
fatty acids
triglyceride
phase
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.)
Withdrawn
Application number
EP17201077.9A
Other languages
German (de)
English (en)
Inventor
Jennifer HEYMANN
Matthias Bahlmann
Jan WOLTER
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.)
Evonik Operations GmbH
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
Priority to EP17201077.9A priority Critical patent/EP3483237A1/fr
Priority to US15/946,791 priority patent/US10301572B1/en
Priority to MYPI2018701506A priority patent/MY176573A/en
Priority to PH12018000112A priority patent/PH12018000112A1/en
Priority to BR102018008028-8A priority patent/BR102018008028A2/pt
Priority to JP2018082307A priority patent/JP6652588B2/ja
Priority to ARP180101049A priority patent/AR111729A1/es
Priority to CN201810378809.6A priority patent/CN109762665A/zh
Publication of EP3483237A1 publication Critical patent/EP3483237A1/fr
Withdrawn legal-status Critical Current

Links

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
    • C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
    • C11B7/0083—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils with addition of auxiliary substances, e.g. cristallisation promotors, filter aids, melting point depressors
    • 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
    • C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
    • C11B7/0008—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents
    • C11B7/0025—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents in solvents containing oxygen in their molecule
    • 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
    • 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

Definitions

  • the invention relates to an improved process for the extraction of fatty acids from triglyceride oils.
  • the extraction of the triglyceride oil is carried out with an aqueous solution comprising at least one quaternary ammonium salt and at least one aliphatic diol having 1 to 8 carbon atoms.
  • the inventive method is characterized by high efficiency.
  • Natural fats and oils have various undesirable components such as metals, free fatty acids and phospholipids and therefore must be refined.
  • the refining of natural fats and oils distinguishes between physical and chemical refining.
  • 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.
  • the WO 2016/149692 A1 describes the acidification of aqueous solutions that originate from saponification reactions and contain lipids.
  • the lipid-containing raw material is mixed with base (especially sodium or potassium hydroxide) and saponified. Subsequently, CO 2 is pressed, this reacts with the reaction mixture and the aqueous phase is removed.
  • the CN 106281672 A describes the treatment of triglyceride oils with antioxidants (eg tocopherol, lactate) and their alkali metal salts to remove trichloropropanol and its derivatives.
  • antioxidants eg tocopherol, lactate
  • alkali metal salts eg tocopherol, lactate
  • the WO 2012/031176 A1 , the WO 2016/189114 A1 , the WO 2016/189115 A1 and the WO 2016/189328 A1 describe the treatment of triglyceride oils with quaternary ammonium salts and their solutions for removing free fatty acids, metals and other undesirable components.
  • a triglyceride oil is extracted with an aqueous solution of a basic quaternary ammonium salt to remove fatty acids therefrom. After extraction, the phases are separated. To regenerate the aqueous solution, which is necessary in order 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 CO 2 . This results in the fatty acid salts of free fatty acids that can be separated from the aqueous phase.
  • WO 2016/189114 A1 discloses a reliable method for extracting free fatty acids from triglyceride oils, this has a problem especially in large-scale applications.
  • 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 from the outset technically very demanding, since they emulsify with water and oil and make the phase separation difficult. Therefore, the quaternary ammonium salts used in the extraction of the fatty acids from the triglyceride oil are difficult or impossible to completely remove from the triglyceride oil.
  • 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.
  • the proportion of the quaternary ammonium salt in the extracted oil can be significantly reduced if the quaternary ammonium salt is added an aliphatic diol having 1 to 8 carbon atoms, with ethylene glycol and propanediols, in particular Ethylene glycol and 1,2-propanediol, are most suitable.
  • nitrogen atom in the context of the invention means a cation having at least one nitrogen atom and one positive charge, this nitrogen atom being bonded only to carbon atoms.
  • the nitrogen atom may be saturated and may be bonded by single bonds to 4 carbon atoms, or it may be unsaturated and bonded to two carbon atoms by a single bond and to a third carbon atom by a double bond
  • the nitrogen atom When the nitrogen atom is unsaturated, it may also be part of a heteroaromatic ring, such as an imidazolium cation or a dialkylimidazolium cation (e.g., 1-methyl-3-ethylimidazolium cation, 1,3-dimethylimidazolium cation, 1,3-diethylimidazolium cation).
  • a heteroaromatic ring such as an imidazolium cation or a dialkylimidazolium cation (e.g., 1-methyl-3-ethylimidazolium cation, 1,3-dimethylimidazolium cation, 1,3-diethylimidazolium cation).
  • nitrogen atom When the nitrogen atom is saturated, it may also be part of an alicyclic ring, for example a pyrrolidinium ring or piperidinium ring.
  • the nitrogen atom is bonded to 4 substituted or unsubstituted hydrocarbon groups of 1 to 12 carbon atoms, which hydrocarbon groups may carry further substituents, these substituents preferably being located on carbon atoms which are not bonded to the positively charged nitrogen atom.
  • Hydrocarbon group in the context of the invention preferably means alkyl, cycloalkyl, alkenyl, alkynyl or aryl.
  • the quaternary ammonium salt is used in the present invention advantageously and preferably as a liquid comprising the salt. It is not volatile and exists only in its ionic form as part of the liquid.
  • This liquid is more preferably the solution of the salt in a solvent, for example water.
  • Possible solvents are selected from polar solvents such as water, ethanol, methanol or mixtures thereof.
  • water is used as the solvent.
  • the quaternary ammonium salt may be an ionic liquid.
  • ionic liquid is known to the person skilled in the art and is described, for example, in US Pat US 7,638,636 B2 described.
  • it may be substituted with one to three OH groups.
  • the quaternary ammonium cation is selected from its compound according to the structure [N (R a ) (R b ) (R c ) (R d ) + , wherein R a , R b , R c and R d are each independently selected from C 1 to C 4 alkyl, including methyl, ethyl, n- propyl, iso -propyl, n -butyl, sec-butyl, iso -butyl and tert -Butyl, wherein at least one of the radical R a , R b , R c or R d on a carbon atom which does not bind directly to the positively charged nitrogen, may be substituted with an OH group.
  • Substitut Of Radicals R a , R b , R c or R d are preferably 2-hydroxyethyl, 2-hydroxypropyl or 2-hydroxy-2-methylethyl.
  • choline is used as the quaternary ammonium cation: (CH 3 ) 3 N + CH 2 CH 2 OH.
  • the quaternary ammonium salt further comprises at least one basic anion selected from hydroxide, alkoxide, alkylcarbonate, bicarbonate, carbonate, serinate, prolinate, histidinate, threoninate, valinate, asparaginate, taurinate, lysinate.
  • the basic anion is selected from alkylcarbonate, bicarbonate, carbonate, hydroxide, alkoxide. More preferably, it is selected from alkoxide, hydrogencarbonate, alkylcarbonate and carbonate; most preferably hydrogencarbonate.
  • the alkyl group is unbranched or branched and is substituted or unsubstituted. It is unbranched and unsubstituted.
  • An alkyl group according to the invention preferably has 1 to 10 carbon atoms, more preferably 1 to 8, most preferably 1 to 4 carbon atoms.
  • the alkyl group may be selected from methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl. Branched alkyl groups such as iso -propyl, iso -butyl, sec -butyl, tert -butyl can also be used. Most preferably, the alkyl group is selected from methyl, ethyl, propyl, butyl, more preferably selected from methyl, ethyl
  • a quaternary ammonium salt comprising a choline cation is particularly preferred in the process of the invention.
  • a quaternary ammonium salt in the process according to the invention, which consists of choline hydrogencarbonate: (CH 3 ) 3 N + CH 2 CH 2 OH HOCOO - ; Choline hydroxide: (CH 3 ) 3 N + CH 2 CH 2 OH OH, Choline alkyl carbonate: (CH 3 ) 3 N + CH 2 CH 2 OH ROCO O - wherein R is an alkyl group having in particular 1 to 4 carbon atoms and more preferably 2 to 3 carbon atoms is, is selected. Choline hydrogen carbonate is most preferably used: (CH 3 ) 3 N + CH 2 CH 2 OH HOOO - .
  • propanediol means any propane which carries 2 OH groups, regardless of which of the carbon atoms.
  • step (a) of the process according to the invention in the aqueous solution W 1, the proportion of aliphatic diol to quaternary ammonium salt such that the molar amount of all aliphatic diols having 1 to 8 carbon atoms based on the molar amount of all quaternary ammonium salts, wherein the quaternary ammonium salt comprises at least one quaternary ammonium cation and at least one basic anion selected from hydroxide, alkoxide, alkylcarbonate, bicarbonate, carbonate, serinate, prolinate, histidinate, threoninate, valinate, asparaginate, taurinate, lysinate, in the range 0.0001% to 99.9%, preferably 0.01 % to 50.0%, more preferably 0. 1% to 40.0%, even more preferably 1.0% to 30.0%, most preferably 10.0% to 20.0%, most preferably 15.3% to 18.8%, most preferably 17.6%.
  • triglyceride oil comprises any oil or fat whose main constituent is> 50% by weight of triglycerides.
  • the oil or fat may also include 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.
  • oils and oils of plant origin and containing flavoring substances are particularly considered (where appropriate in parentheses 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 nut oil ( Anacardium occidentale ) , oil from plants of the genus Citrus (cf.
  • 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.
  • the fat and oil of plant origin is palm oil.
  • Suitable fats and oils of animal origin and containing flavoring substances are, in particular: marmot fat, butter fat, fish oil, oil obtainable from crustaceans (for example krill), cod liver oil, milk fat, lard, duck lard, goose fat, beef tallow, wool wax.
  • Fatty acids within the meaning of the invention comprises saturated and monounsaturated or polyunsaturated fatty acids. Furthermore, this term according to the invention (unless otherwise stated in the specific case) always includes both the protonated and the deprotonated form of the respective fatty acid.
  • Examples of unsaturated fatty acids are myristoleic acid, palmitoleic acid, sapienic acid, oleic acid, elaidic acid, vaccenic acid, linoleic acid, linolelaidic acid, ⁇ -linolenic acid, arachidonic acid, eicosapentaenoic acid, erucic acid and docosahexaenoic acid.
  • saturated fatty acids are caprylic, capric, undecanoic, lauric, tridecanoic, myristic, palmitic, margaric, stearic, nonadecanoic, arachidic, heneicosanoic, behenic, lignoceric and cerotic acids.
  • Palm oil means an oil obtainable from a plant of the genus Elaeis (part of the family of the palm-like or palm trees Arecaceae or Palmae ) , in particular Elaeis guineensis, Elaeis oleifera or hybrids thereof.
  • the palm oil may be available, for example, from the pulp or the core of 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 has not been subjected to a refining step.
  • 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.
  • a triglyceride oil T 1 comprising fatty acids is contacted with an aqueous solution W 1 comprising at least one quaternary ammonium salt and at least one aliphatic diol having 1 to 8 carbon atoms.
  • 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 90 ° C, more preferably 40 ° C to 90 ° C, even more preferably 70 ° C to 90 ° ° C, most preferably at 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.
  • the contacting of the triglyceride oil T 1 comprising fatty acids with an aqueous solution W 1 comprising at least one quaternary ammonium salt and at least one aliphatic diol having 1 to 8 carbon atoms can take place by methods known to the person skilled in the art.
  • the contacting can take place in a vessel in which T 1 and W 1 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 T 1 into the aqueous phase W 1 .
  • a mechanical mixer such as a stirred tank, which can be operated non-continuously or continuously
  • an ultrasonic mixer or an electromagnetic mixer used.
  • an inert gas can be passed through the resulting mixture blow.
  • T 1 and W 1 can also be mixed in a static mixer such as a Sulzer mixer or Kenics mixer.
  • T 1 and W 1 continuously in countercurrent, for example in a column or in cocurrent.
  • the column may be a sieve tray column, a packed column or a stirred column, such as a Kühni column or a Scheibel column.
  • T 1 and W 1 can also be guided through a pipe before contacting them with the aid of a pump, at the end of which they meet and mix, and then pass through a flow pipe R.
  • the triglyceride oil T 1 is introduced at or at least near the bottom of the column and the aqueous solution W 1 is introduced at or near the top of the column.
  • aqueous phase W 2 which has a higher fatty acid content than W 1 , is then removed at or near the bottom of the column, and a triglyceride oil phase T 2 having a reduced fatty acid content compared to T 1 is then at or near discharged at the top of the column.
  • the column also has a sump region in which a secondary stream can be collected, and more preferably the triglyceride oil T 1 is then fed directly above this sump region.
  • countercurrent column 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) is carried out in which T 1 and W 1 are mixed in cocurrent, more preferably in at least one mixer-settler.
  • the volume ratio of T 1 and W 1 in step (a) of the method is likewise not limited further.
  • the ratio of the volume of triglyceride oil T 1 to the volume of the aqueous phase W 1 is in particular in the range from 10: 1 to 1: 100, more preferably 1: 1 to 1:10; even more preferably 1: 1.5 to 1: 4, even more preferably 3: 7.
  • the mixing such as, for example, the contacting in the column in the case of continuous contacting, can be adapted by the person skilled in the art so that as much of the fatty acids as possible are transferred from the triglyceride oil phase T 1 into the aqueous phase W 1 . Accordingly, the contacting is carried out, for example, for 1 second to 2 hours, in particular 30 seconds to 1 hour, preferably 1 to 50 minutes, more preferably 10 to 40 minutes, most preferably 20 to 30 minutes.
  • the fatty acids comprised by the triglyceride oil T 1 are neutralized in step (a) of the process according to the invention by the quaternary ammonium salts comprised by the aqueous phase W 1 .
  • the molar amount of all quaternary ammonium salts comprised by the aqueous phase W 1 is at least equal to the molar amount of all the fatty acids comprised by the triglyceride oil T 1 .
  • the ratio of the molar amount of all quaternary ammonium salts comprised by aqueous phase W 1 to the molar amount of all fatty acids comprising triglyceride oil T 1 is preferably in the range 1: 1 to 500: 1, more preferably 2: 1 to 200: 1, even more preferably 10 : 1 to 100: 1, most preferably 30: 1 to 70: 1.
  • 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 phenolphthaleininidkator. After determining the proportions of fatty acids in the triglyceride oil T 1, the expert then also knows how large the desired molar amount of all quaternary from the aqueous phase W 1 ammonium salts must be, which he can then adjust accordingly.
  • an aqueous phase W 1 comprising at least one quaternary ammonium salt and at least one aliphatic diol having 1 to 8 carbon atoms is used.
  • the aqueous solution may also comprise further solvents, for example acetone, ethyl acetate, alcohols, preferably methanol or ethanol.
  • the aqueous phase W 1 preferably comprises no further solvents, which means according to the invention that the weight fraction of the sum of all quaternary ammonium salts and all aliphatic diol having 1 to 8 carbon atoms and of the water in W 1 is at least 95% by weight, preferably at least 99 wt%, more preferably at least 99.9 wt%, and the rest of W 1 thereof are various chemical substances such as organic solvents.
  • the total concentration of all quaternary ammonium salts in the aqueous phase W 1 is not further limited and is preferably in the range 70 to 80 wt .-%, preferably 75 wt .-%, based on the total mass of the phase W 1 .
  • a triglyceride oil T 1 comprising fatty acids
  • an aqueous solution comprising at least one quaternary ammonium salt and at least one aliphatic diol having 1 to 8 carbon atoms W 1
  • the fatty acids from the triglyceride oil T 1 at least partially pass into the aqueous phase W 1 . Therefore, when carrying out step (a), a triglyceride oil phase T 2 and an aqueous phase W 2 are obtained, wherein T 2 has a reduced fatty acid content compared to T 1 and W 2 has an increased content of fatty acids compared to W 1 .
  • step (b) of the process according to the invention the triglyceride oil phase T 2 is then separated from the aqueous phase W 2 .
  • the triglyceride oil phase T 2 is the upper phase, while the aqueous phase W 2 is the lower phase.
  • 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.
  • the triglyceride oil phase T 2 is separated from the aqueous phase W 2 in a centrifuge.
  • a salt precipitates in W 1 during the contacting in step (a) and is present in the triglyceride oil phase T 2 as a solid, it can also be separated off by centrifugation or filtration. Solvent or water may also be added to the solid triglyceride oil phase T 2 to solubilize the solid and separate the aqueous solution containing the appropriate salt as described above.
  • the step (a) and the step (b) of the method according to the invention ie the contacting and separation, in a centrifugal separator, such as in US 4,959,158 . US 5,571,070 . US 5,591,340 . US 5,762,800 . WO 99/12650 and WO 00/29120 is described.
  • T 1 and W 1 are first supplied as separate streams into the separator 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 T 1 into the first separator of the series, and the aqueous phase W 1 into the last separator in the series, so that triglyceride oil with decreasing content of fatty acids passes through the first to the last separator of the series, while the aqueous phase with increasing content of fatty acids the separator in the opposite direction passes.
  • the aqueous phase W 2 is then taken from the first separator in the series, the triglyceride oil phase T 2 is taken from the last separator in the series.
  • the triglyceride oil phase T 2 can also be fed to a coalescing filter in order to remove the last drop 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 T 2 can then be fed to a further work-up or processing.
  • a step may be one or more selected from degumming, deacidification, winterization, bleaching, depigmentation, deodorization.
  • the triglyceride oil phase T 2 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 T 2 is used as triglyceride oil T 1 is contacted and in each step with a new batch of aqueous phase W 1 comprising (alkaline) alkali metal (hydrogen) carbonate (s) to further reduce the proportion of fatty acids in the triglyceride oil phase T 2 .
  • aqueous phases W 2 obtained in these additional steps can then be supplied completely or partially to the subsequent step (c), etc.
  • step (c), in which the aqueous phase is regenerated can then be carried out.
  • step (c) the addition of CO 2 and optionally an organic solvent to the aqueous phase W 2 takes place, whereby a fatty acid-containing organic phase and an aqueous phase W 3 is obtained, which has a lower content of fatty acids compared to W 2 .
  • the corresponding conditions are known to the skilled person and, for example, in the WO 2016/149692 A1 described.
  • the contacting of the aqueous phase W 2 with CO 2 and optionally an organic solvent can take place by methods known to those skilled in the art.
  • the contacting can take place in a gas-tight sealable pressure vessel in which W 2 and CO 2 and optionally an organic solvent are mixed together.
  • CO 2 can be introduced, for example, via a capillary or a gasatable stirrer.
  • the contacting should take place so that as much CO 2 in the aqueous Phase W 2 is entered.
  • a mechanical mixer or an electromagnetic mixer is used.
  • the volume ratio of W 2 and the organic solvent in step (c) of the process is not further 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.
  • organic solvent in step (c) are preferably diisopropyl ether, n-butyl acetate, ethyl acetate, hexane, 1-hexanol, preferably n-butyl acetate.
  • 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 from 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 CO 2 used in step (c) may come from a combustion process or blast furnace process and may include other ingredients such as N 2 O, SO 2 , H 2 S, NO 2 . These components can further acidify the aqueous phase W 2 , so that it further favors the formation of a fatty acid-containing organic phase.
  • step (c) a fatty acid-containing organic phase and an aqueous phase W 3 having a lower content of fatty acids than W 2 are then obtained.
  • step (d) in the process according to the invention, the aqueous phase W 3 can be separated off from the fatty acid-containing organic phase obtained in step (c).
  • step (b) of the process according to the invention can be carried out by methods familiar to the person skilled in the art, as also described for step (b) of the process according to the invention.
  • phase W 3 is obtained which can be treated in a new cycle with a new batch of triglyceride oil.
  • aqueous phase W 3 is contacted with further triglyceride oil T 3 comprising at least one quaternary ammonium salt and at least one aliphatic diol having 1 to 8 carbon atoms, whereby a triglyceride oil phase T 4 and an aqueous phase W 4 are obtained, wherein T 4 has a relation to T 3 reduced content of fatty acids and W 4 has a relation to W 3 increased content of fatty acids.
  • step (e) is preferably carried out as described for step (a).
  • the process according to the invention is suitable for recycling the aqueous phase W 1 over and over again and for use in a new extraction process.
  • triglyceride phase T 2 obtained in step (b) of the process according to the invention can be subjected to one or more further refining steps, for example selected from degumming, deacidification, bleaching, depigmentation, deodorization, winterization.
  • the content of fatty acids in the obtained triglyceride phase was determined by titration to 0.16 wt .-%. This corresponds to a turnover of free fatty acids of 97.2%.
  • the content of free choline in the triglyceride phase was determined by HPLC-ESI-MS to be 389 ppm.
  • the content of fatty acids in the obtained triglyceride phase was determined by titration to 0.13 wt .-%. This corresponds to a conversion of free fatty acids of 97.8%.
  • the content of free choline in the triglyceride phase was determined by HPLC-ESI-MS to be 2442 ppm.
  • the content of fatty acids in the obtained triglyceride phase was determined by titration to 0.11 wt .-%. This corresponds to a free fatty acid conversion of 98.2%.
  • the content of free choline in the triglyceride phase was determined by HPLC-ESI-MS to 4853 ppm.
  • Table 1 example diol FFA content [%] Sales [%] Choline content [ppm] separation time V1 - 12:11 98.2 11364 120 minutes, turbid aqueous phase V2 - 12:08 98.6 6405 30 minutes, turbid aqueous phase E1 3.5 g of ethylene glycol 12:16 97.2 389 30 min, clear phases E2 3.5 g of ethylene glycol 12:13 97.8 2442 45 min, clear phases E3 3.5 g of 1,2-propanediol 12:11 98.2 4853 45 min, clear phase
EP17201077.9A 2017-11-10 2017-11-10 Procédé d'extraction d'acides gras d'une huile glycéridique Withdrawn EP3483237A1 (fr)

Priority Applications (8)

Application Number Priority Date Filing Date Title
EP17201077.9A EP3483237A1 (fr) 2017-11-10 2017-11-10 Procédé d'extraction d'acides gras d'une huile glycéridique
US15/946,791 US10301572B1 (en) 2017-11-10 2018-04-06 Process for extracting fatty acids from triglyceride oils
MYPI2018701506A MY176573A (en) 2017-11-10 2018-04-17 Process for extracting fatty acids from triglyceride oils
PH12018000112A PH12018000112A1 (en) 2017-11-10 2018-04-19 Process for extracting fatty acids from triglyceride oils
BR102018008028-8A BR102018008028A2 (pt) 2017-11-10 2018-04-20 Processo para extrair ácidos graxos de óleos triglicerídeos
JP2018082307A JP6652588B2 (ja) 2017-11-10 2018-04-23 トリグリセリド油から脂肪酸を抽出する方法
ARP180101049A AR111729A1 (es) 2017-11-10 2018-04-24 Proceso para extraer ácidos grasos de aceites de triglicéridos
CN201810378809.6A CN109762665A (zh) 2017-11-10 2018-04-25 从甘油三酯油中提取脂肪酸的方法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP17201077.9A EP3483237A1 (fr) 2017-11-10 2017-11-10 Procédé d'extraction d'acides gras d'une huile glycéridique

Publications (1)

Publication Number Publication Date
EP3483237A1 true EP3483237A1 (fr) 2019-05-15

Family

ID=60515104

Family Applications (1)

Application Number Title Priority Date Filing Date
EP17201077.9A Withdrawn EP3483237A1 (fr) 2017-11-10 2017-11-10 Procédé d'extraction d'acides gras d'une huile glycéridique

Country Status (8)

Country Link
US (1) US10301572B1 (fr)
EP (1) EP3483237A1 (fr)
JP (1) JP6652588B2 (fr)
CN (1) CN109762665A (fr)
AR (1) AR111729A1 (fr)
BR (1) BR102018008028A2 (fr)
MY (1) MY176573A (fr)
PH (1) PH12018000112A1 (fr)

Citations (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2771480A (en) 1953-07-29 1956-11-20 Benjamin Clayton Purification of glyceride oils by means of ion-exchange resins
GB1520523A (en) * 1975-08-21 1978-08-09 Rewo Chemische Werke Gmbh Processes for the refining of crude oils &c of animal or vegetable origin
US4959158A (en) 1989-03-30 1990-09-25 The United States Of America As Represented By The Unitd States Department Of Energy Method for separating disparate components in a fluid stream
US5571070A (en) 1996-01-16 1996-11-05 Costner Industries Nevada, Inc. Rotor sleeve for a centrifugal separator
US5591340A (en) 1995-09-01 1997-01-07 Costner Industries Nevada, Inc. Centrifugal separator
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
US20010005759A1 (en) * 1998-08-11 2001-06-28 Raymond Bertholet Process for refining fatty substances
US7638636B2 (en) 2002-08-16 2009-12-29 Cytec Technology Corp. Phosphonium and imidazolium salts and methods of their preparation
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
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
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
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
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
US20170022447A1 (en) * 2013-11-28 2017-01-26 Martin Atkins Removal of free fatty acids from glyceride oils

Family Cites Families (68)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB499678A (en) 1936-09-28 1939-01-27 Bataafsche Petroleum A process for removing acid components from hydrocarbons or derivatives thereof
US2200391A (en) * 1939-01-17 1940-05-14 Pittsburgh Plate Glass Co Solvent extraction of glyceride oils
GB708831A (en) 1950-08-09 1954-05-12 Unilever Ltd Improvements in the refining of fatty glycerides
GB764833A (en) 1954-05-07 1957-01-02 Benjamin Clayton Improvements in or relating to treatment of glyceride oils
US2998382A (en) 1958-10-01 1961-08-29 Exxon Research Engineering Co Regeneration of spent caustic by foaming
US4199440A (en) 1977-05-05 1980-04-22 Uop Inc. Trace acid removal in the pretreatment of petroleum distillate
GB2068404B (en) 1979-10-25 1984-01-18 Unilever Ltd Process for bleaching oils and fats
AU548951B2 (en) 1982-04-21 1986-01-09 Unilever Plc Process for refining lipids by ultrafiltration
US4629588A (en) 1984-12-07 1986-12-16 W. R. Grace & Co. Method for refining glyceride oils using amorphous silica
US4915876A (en) 1987-07-20 1990-04-10 General Mills, Inc. Process for the deodorization and stabilization of polyunsaturated oils
JPH04183794A (ja) 1990-11-19 1992-06-30 Fuji Oil Co Ltd 精製パーム油の製造方法
EP0560121A3 (en) 1992-03-09 1994-07-27 Vandemoortele Int Nv Method for refining glyceride oil
EP0646162A4 (en) 1993-03-18 1995-04-19 Pq Corporation Process for reducing contaminants in glyceride oils.
JPH08302382A (ja) 1995-05-09 1996-11-19 Nippon Synthetic Chem Ind Co Ltd:The 魚油の精製法
GB9603754D0 (en) 1996-02-22 1996-04-24 Bp Chem Int Ltd Lubricating oils
DE19638459A1 (de) 1996-09-19 1998-03-26 Peter Siegfried Verfahren zur Reinigung von Fetten und Ölen tierischen oder vegetabilischen Ursprungs
CN1087339C (zh) 1997-07-09 2002-07-10 结晶及脱胶公司 从脂肪物质中除去金属以及粘合在所述金属上的树胶的方法
JP2000202299A (ja) 1999-01-20 2000-07-25 Tosoh Corp エチレンの三量化触媒及びこれを用いたエチレンの三量化方法
GB9902518D0 (en) 1999-02-04 1999-03-24 Bp Exploration Operating A process for deacidifying a crude oil system
WO2000068236A1 (fr) 1999-05-07 2000-11-16 Daniels Ralph S Economie et autres avantages retires du raffinage de l'huile vegetale avec l'hydroxyde de potassium
HUP0203610A3 (en) 1999-11-05 2004-06-28 Johnson Mattey Plc Immobilised ionic liquids
US6395948B1 (en) 2000-05-31 2002-05-28 Chevron Chemical Company Llc High viscosity polyalphaolefins prepared with ionic liquid catalyst
US6832229B2 (en) 2001-03-09 2004-12-14 Oracle International Corporation System and method for maintaining large-grained database concurrency with a log monitor incorporating dynamically redefinable business logic
US6673737B2 (en) 2001-05-30 2004-01-06 Exxonmobil Research And Engineering Company Ionic liquid compositions
DE10155281A1 (de) 2001-11-08 2003-06-05 Solvent Innovation Gmbh Verfahren zur Entfernung polarisierbarer Verunreinigungen aus Kohlenwasserstoffen und Kohlenwasserstoffgemischen durch Extraktion mit ionischen Flüssigkeiten
WO2003040264A1 (fr) 2001-11-06 2003-05-15 Extractica, Llc Procede d'extraction de composes organo-sulfureux a partir d'hydrocarbures a l'aide de liquides ioniques
US6638551B1 (en) 2002-03-05 2003-10-28 Selecto Scientific, Inc. Methods and compositions for purifying edible oil
FR2845084B1 (fr) 2002-09-26 2009-07-17 Centre Nat Rech Scient Compositions contenant des liquides ioniques et leurs utilisations, notamment en synthese organique
FR2861084B1 (fr) 2003-10-15 2006-01-21 Arkema Procede d'elimination de composes benzothiopheniques contenus dans un melange d'hydrocarbures
FR2875235B1 (fr) 2004-09-10 2006-11-24 Inst Francais Du Petrole Procede de separation des composes oxygenes contenus dans une charge hydrocarbonee, mettant en oeuvre un liquide ionique
JP2006160969A (ja) 2004-12-10 2006-06-22 Mitsubishi Materials Corp 灯軽油留分の精製方法及び灯軽油留分を精製する抽出溶剤
GB0500029D0 (en) 2005-01-04 2005-02-09 Univ Belfast Basic ionic liquids
GB0525251D0 (en) 2005-12-12 2006-01-18 Univ Belfast Oligomerisation
US7572944B2 (en) 2005-12-20 2009-08-11 Chevron U.S.A. Inc. Process for making and composition of superior lubricant or lubricant blendstock
CN101032677A (zh) 2006-03-08 2007-09-12 波克股份有限公司 气体净化方法
EP1911829A1 (fr) 2006-10-10 2008-04-16 The Queen's University of Belfast Procédé de déacidification du brut
WO2007138307A2 (fr) 2006-05-25 2007-12-06 The Queen's University Of Belfast Procédé d'élimination d'acides contenant du soufre dans le pétrole brut
DE102007028427A1 (de) 2007-06-20 2008-12-24 KLüBER LUBRICATION MüNCHEN KG Verwendung von ionischen Flüssigkeiten zur Verbesserung der Eigenschaften von Schmierstoffzusammensetzungen
DE102008060059A1 (de) 2008-12-02 2010-06-10 Süd-Chemie AG Verfahren zur Reduzierung des 3-MCPD-Gehalts in raffinierten Pflanzenölen
GB0908986D0 (en) 2009-05-26 2009-07-01 Univ Belfast Process for removing organic acids from crude oil and crude oil distillates
US8173826B2 (en) 2009-06-17 2012-05-08 Chevron U.S.A. Inc. Enrichment of monounsaturated acids/esters in vegetable oil—or animal fat-based feedstock using metal salts dissolved in ionic liquids
SG177423A1 (en) 2009-06-30 2012-02-28 Sime Darby Malaysia Berhad Process for removing unwanted propanol components from unused triglyceride oil
MX2012000945A (es) 2009-07-21 2012-02-28 Nestec Sa Un aceite o grasa comestible desodorizada con niveles bajos de mcpd ligado y proceso de elaboracion mediante purificacion de carboximetil celulosa y/o resina.
EP2456848A1 (fr) 2009-07-21 2012-05-30 Nestec S.A. Graisse ou huile comestible désodorisée à faibles teneurs en mcpd lié et son procédé de fabrication au moyen d'un gaz inerte
US8764967B2 (en) 2009-07-31 2014-07-01 Gas Technology Institute On-site frying oil regeneration method and apparatus
RU2012125197A (ru) 2009-12-04 2014-01-10 Арчер Дэниелс Мидлэнд Компани Уменьшение глицидных сложных эфиров в масле
US8715490B2 (en) 2009-12-23 2014-05-06 Uop Llc Low metal biomass-derived pyrolysis oils and processes for producing the same
US8426621B2 (en) 2010-02-22 2013-04-23 Riceland Foods, Inc. Refined edible oil having high beneficial constituents and methods for refining thereof
AU2011234658B2 (en) * 2010-04-01 2014-12-04 Evonik Operations Gmbh Fabric softener active composition
WO2012004810A1 (fr) 2010-07-08 2012-01-12 Indian Oil Corporation Ltd. Procédé pour l'élimination de métaux d'huiles/matières grasses
DE102010052723B4 (de) 2010-11-25 2013-11-07 Technische Universität Ilmenau Verfahren und Vorrichtung zum Vorbereiten oder Bearbeiten von Prozessgut, insbesondere biologischen Prozesgut
GB2485824B (en) 2010-11-25 2017-12-20 The Queen's Univ Of Belfast Process for removing organic acids from crude oil and crude oil distillates
CN102031202B (zh) 2010-12-08 2012-12-05 中国科学院西双版纳热带植物园 一种离子液体催化制备生物柴油的方法
EP2502500B1 (fr) 2011-03-25 2013-08-21 Nestec S.A. Production d'huiles végétales raffinées à partir d'huile végétale brute lavée
KR101207413B1 (ko) 2011-06-09 2012-12-04 씨제이제일제당 (주) 3-클로로-1,2-프로판디올 생성물질이 저감된 식용유지 및 그 제조방법
JP6008596B2 (ja) 2011-06-15 2016-10-19 花王株式会社 精製油脂の製造方法
ES2731265T3 (es) 2011-12-23 2019-11-14 Bunge Loders Croklaan B V Método de tratamiento de un aceite vegetal
JP2013250186A (ja) 2012-06-01 2013-12-12 Fuji Oil Co Ltd 超臨界流体クロマトグラフィーを用いた、食用油脂中の３−モノクロロプロパン−１，２−ジオール脂肪酸エステル類の分離又は測定方法
WO2014012548A1 (fr) 2012-07-18 2014-01-23 Aarhuskarlshamn Ab Réduction de composés de mcpd dans l'huile végétale raffinée pour aliments
WO2014042937A1 (fr) 2012-09-14 2014-03-20 Archer Daniels Midland Company Procédés d'élimination de monochloropropanediols et/ou de glycidol du glycérol
DE102013010035A1 (de) 2013-06-17 2014-12-18 Evonik Degussa Gmbh Absorptionsmedium und Verfahren zur Absorption von CO2 aus einer Gasmischung
CN104419519B (zh) 2013-08-30 2017-08-22 中国石油化工股份有限公司 一种乳化生物柴油破乳的方法
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
CN106459828A (zh) 2014-06-05 2017-02-22 Gea韦斯伐里亚分离机集团有限公司 分步加工有机油的方法和装置
GB2528128A (en) 2014-07-11 2016-01-13 Univ Belfast Oligomerisation process
GB2538756A (en) 2015-05-27 2016-11-30 The Queen's Univ Of Belfast A process for refining glyceride oil comprising a basic ionic liquid treatment
GB2538759B (en) 2015-05-27 2020-12-16 Univ Belfast Process for removing metal contaminants from glyceride oil and a glyceride oil refining process incorporating the same
GB2538760A (en) 2015-05-27 2016-11-30 The Queen's Univ Of Belfast Removal of free fatty acids from glyceride oils

Patent Citations (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2771480A (en) 1953-07-29 1956-11-20 Benjamin Clayton Purification of glyceride oils by means of ion-exchange resins
GB1520523A (en) * 1975-08-21 1978-08-09 Rewo Chemische Werke Gmbh Processes for the refining of crude oils &c of animal or vegetable origin
US4959158A (en) 1989-03-30 1990-09-25 The United States Of America As Represented By The Unitd States Department Of Energy Method for separating disparate components in a fluid stream
US5591340A (en) 1995-09-01 1997-01-07 Costner Industries Nevada, Inc. Centrifugal separator
US5762800A (en) 1995-09-01 1998-06-09 Costner Industries Nevada, Inc. Centrifugal separator
US5571070A (en) 1996-01-16 1996-11-05 Costner Industries Nevada, Inc. Rotor sleeve for a centrifugal separator
WO1999012650A1 (fr) 1997-09-11 1999-03-18 Costner Industries Nevada, Inc. Rotor autonettoyant pour separateur centrifuge
US20010005759A1 (en) * 1998-08-11 2001-06-28 Raymond Bertholet Process for refining fatty substances
WO2000029120A1 (fr) 1998-11-16 2000-05-25 Costner Industries Nevada, Inc. Ensemble rotor pour separateur centrifuge
US7638636B2 (en) 2002-08-16 2009-12-29 Cytec Technology Corp. Phosphonium and imidazolium salts and methods of their preparation
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
US20170022447A1 (en) * 2013-11-28 2017-01-26 Martin Atkins Removal of free fatty acids from glyceride oils
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
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
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
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

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
C.E.C. RODRIGUES; C.B. GONGALVES; E. BATISTA; J.A. MEIRELLES, RECENT PATENTS ON ENGINEERING, vol. 1, 2007, pages 95 - 102

Also Published As

Publication number Publication date
CN109762665A (zh) 2019-05-17
BR102018008028A2 (pt) 2019-06-04
JP2019089995A (ja) 2019-06-13
US20190144778A1 (en) 2019-05-16
US10301572B1 (en) 2019-05-28
PH12018000112A1 (en) 2019-11-04
MY176573A (en) 2020-08-17
JP6652588B2 (ja) 2020-02-26
AR111729A1 (es) 2019-08-14

Similar Documents

Publication Publication Date Title
DE883605C (de) Verfahren zur Fraktionierung von Mischungen organischer Verbindungen durch Behandlung mit Harnstoff
EP0610742B1 (fr) Procédé d'obtention de tocophérols et de stérols à partir de sources naturelles
EP1339817B1 (fr) Procede de production d'esters d'acides gras
EP3152283B1 (fr) Procédé et dispositif de traitement par étapes d'une huile organique
DK170227B1 (da) Fremgangsmåde til kontinuerlig fraktionering af en blanding af fedtsyrer og anvendelse af en fraktion beriget med gamma-linolensyre opnået ved fremgangsmåden
EP1802731B1 (fr) Procede de transesterification de graisses et d'huiles d'origine biologique au moyen d'une alcoolyse, a l'aide de carbonates specifiques
DE60104390T2 (de) Procede d'extraction des insaponifiables des huiles vegetales au moyen de chloro-1-butane
EP1171555B1 (fr) Procede pour eliminer des acides gras libres, contenus dans des corps gras et des huiles d'origine biologique ou dans leurs condensats de vapeur
JP2016540077A (ja) グリセリド油からの遊離脂肪酸の除去
DE102005003625A1 (de) Verfahren zur Herstellung einer DHA-haltigen Fettsäure-Zusammensetzung
DE3446795A1 (de) Verfahren zur herstellung einer fettsaeuremischung mit einer hohen konzentration an eicosapentaensaeure
EP2548937A1 (fr) Glycérates métalliques alcalino-terreux ou alcalins destinés à la désacidification et au séchage d'esters d'acides gras
DE102008063711A1 (de) Verfahren zum Erzeugen von Biodiesel mit verbesserten Filtrationseigenschaften und entsprechend erzeugter Biodiesel
CH630403A5 (de) Verfahren zur entfernung von verunreinigungen aus triglyceridoelen.
EP2635592B1 (fr) Procédé d'extraction de phytostérols et/ou de tocophérols à partir de résidus d'une distillation d'esters d'huiles végétales, de préférence à partir de résidus de distillation issus d'une transestérification d'huiles végétales
AT397966B (de) Verfahren zur herstellung von fettsäureestern niederer einwertiger alkohole
EP3483237A1 (fr) Procédé d'extraction d'acides gras d'une huile glycéridique
WO2019092013A1 (fr) Procédé d'extraction d'acides gras à partir d'huiles triglycéridiques
AT510636B1 (de) Verfahren zur herstellung von fettsäureestern niederer alkohole
WO2019092017A1 (fr) Procédé d'extraction d'acides gras à partir d'huiles triglycéridiques
DE102017220041A1 (de) Verfahren zur Extraktion von Chlorid aus Triglyceridölen
DE60026869T2 (de) Verfahren zur reinigung von phytosterol aus fettsäuren und deren estern
DE102017220045A1 (de) Verfahren zur Extraktion von 3-Chlor-1,2-Propandiol aus Triglyceridölen
AT519685B1 (de) Verfahren zur Herstellung eines Fettsäurealkylesters
EP2933322A1 (fr) Procédé de préparation de cires animales et végétales

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

AX Request for extension of the european patent

Extension state: BA ME

17P Request for examination filed

Effective date: 20190730

RBV Designated contracting states (corrected)

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: EVONIK OPERATIONS GMBH

RIC1 Information provided on ipc code assigned before grant

Ipc: C11B 3/06 20060101ALI20200518BHEP

Ipc: C11B 3/00 20060101AFI20200518BHEP

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: GRANT OF PATENT IS INTENDED

INTG Intention to grant announced

Effective date: 20200706

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20201117