WO2019092017A1 - 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
WO2019092017A1
WO2019092017A1 PCT/EP2018/080471 EP2018080471W WO2019092017A1 WO 2019092017 A1 WO2019092017 A1 WO 2019092017A1 EP 2018080471 W EP2018080471 W EP 2018080471W WO 2019092017 A1 WO2019092017 A1 WO 2019092017A1
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WO
WIPO (PCT)
Prior art keywords
oil
fatty acids
aqueous phase
phase
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2018/080471
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German (de)
English (en)
Inventor
Jennifer HEYMANN
Benjamin Willy
Matthias Bahlmann
Christian BRAMSIEPE
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
Publication of WO2019092017A1 publication Critical patent/WO2019092017A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C11B3/006—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

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 mixtures of (alkaline) alkali metal bicarbonates and certain carboxylic acid salts.
  • the inventive method is characterized by the fact that a particularly efficient separation is achieved compared to conventional methods.
  • 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 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 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 2015/031857 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.
  • WO 2016/189114 A1 describes the treatment of triglyceride oils with quaternary ammonium salts and their solutions for removing free fatty acids, metals and other undesired components.
  • 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, CO2 is pressed, this reacts with the reaction mixture and the aqueous phase is removed.
  • WO 2012/031 176 A1 describes the extraction of unrefined triglyceride oil with solutions of alkali metal carbonates.
  • 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 invention accordingly relates to a process for the extraction of fatty acids from triglyceride oils, comprising the step (a), in which (a) a triglyceride oil Ti comprising fatty acids with an aqueous solution Wi comprising at least one salt S selected from the group consisting of
  • step (a) is essential for the method according to the invention.
  • the inventive method also comprises the step (b) with
  • step (b) separating the triglyceride oil phase T2 from the aqueous phase W2.
  • step (c) is followed by step (c)
  • step (c) addition of CO2 and optionally an organic solvent to the aqueous phase W2, whereby an aqueous phase W3, which has a lower content of fatty acids compared to W2, and a fatty acid-containing organic phase Fo are obtained.
  • step (c) is followed by a step (d)
  • step (d) separating the aqueous phase W3 from the fatty acid-containing organic phase Fo obtained in step (c).
  • step (d) is followed by a step (e)
  • alkaline earth metal bicarbonate selected from the group consisting of alkaline earth metal bicarbonate
  • step (a) If such a solution is used in step (a), this leads to a surprisingly rapid and efficient separation of the aqueous phases T2 and W2 obtained in this step.
  • 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
  • the alkali metal bicarbonate is preferably selected from the group consisting of sodium bicarbonate, potassium bicarbonate, and more preferably in the context of the invention in the alkali metal bicarbonate to
  • 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 (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 (for example lemon, orange, grapefruit, lime), cupuagu butter (Theobroma grandiflorum), thistle oil (Carthamus ), Peanut oil (Arachis hypogaea), rose hip seed oil (Rosa), hemp oil (cannabis), hazel
  • fats and oils of animal origin are in particular: marmot fat, butter fat, fish oil, oil available from crustaceans (for example krill), cod liver oil, milk fat, lard, duck lard, goose fat, beef tallow, wool wax.
  • 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 of the plant.
  • Refining step was subjected.
  • unrefined triglyceride oil has not undergone any of the following refining steps: degumming, deacidification, bleaching, depigmentation, deodorization, winterization.
  • 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 of ⁇ 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.
  • the fatty acids comprised by the triglyceride oil T1 are neutralized in step (a) of the process according to the invention by the salts S selected from the aqueous phase W1 selected from the group consisting of alkaline earth metal hydrogencarbonate, alkali metal hydrogen carbonate.
  • 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
  • the concentration of all salts S selected from the group consisting of
  • E2 aqueous salt solution in which the following concentration of the respective substance is present:
  • E3 aqueous salt solution in which the following concentration of the respective substance is present:
  • V1 3.0 M KHCOs solution in water.
  • reaction mixture was transferred to a separatory funnel and the time was determined until complete separation of the phases.
  • the content of fatty acids in the obtained triglyceride phase was determined by titration (see Table 1, next page).
  • 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.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Microbiology (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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 contenant des mélanges de carbonates d'hydrogène de métaux alcalins (terreux) et de sels d'acides carboxyliques déterminés. Le procédé selon l'invention est caractérisé en ce qu'une séparation particulièrement efficace est obtenue par rapport aux procédés classiques.
PCT/EP2018/080471 2017-11-10 2018-11-07 Procédé d'extraction d'acides gras à partir d'huiles triglycéridiques Ceased WO2019092017A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP17201066.2 2017-11-10
EP17201066 2017-11-10

Publications (1)

Publication Number Publication Date
WO2019092017A1 true WO2019092017A1 (fr) 2019-05-16

Family

ID=60574359

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2018/080471 Ceased WO2019092017A1 (fr) 2017-11-10 2018-11-07 Procédé d'extraction d'acides gras à partir d'huiles triglycéridiques

Country Status (2)

Country Link
AR (1) AR113568A1 (fr)
WO (1) WO2019092017A1 (fr)

Citations (15)

* 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
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
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
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

Patent Citations (16)

* 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
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
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
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

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

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