EP4203693A1 - Procédé de production d'huile à partir d'un produit de micro-algues - Google Patents

Procédé de production d'huile à partir d'un produit de micro-algues

Info

Publication number
EP4203693A1
EP4203693A1 EP21766652.8A EP21766652A EP4203693A1 EP 4203693 A1 EP4203693 A1 EP 4203693A1 EP 21766652 A EP21766652 A EP 21766652A EP 4203693 A1 EP4203693 A1 EP 4203693A1
Authority
EP
European Patent Office
Prior art keywords
microalgae
product
oil
content
intermediate product
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.)
Pending
Application number
EP21766652.8A
Other languages
German (de)
English (en)
Inventor
Gideon GIESSELMANN
Roberto FRONZONI
Denitsa SHOPOVA-GOSPODINOVA
Elia RAMOS-TERCERO
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.)
K D Pharma Bexbach GmbH
Original Assignee
K D Pharma Bexbach 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 K D Pharma Bexbach GmbH filed Critical K D Pharma Bexbach GmbH
Publication of EP4203693A1 publication Critical patent/EP4203693A1/fr
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
    • A23D9/04—Working-up
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
    • C11C1/005—Splitting up mixtures of fatty acids into their constituents
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
    • C11C1/08—Refining
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
    • C11C1/08—Refining
    • C11C1/10—Refining by distillation
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C11C3/08—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with fatty acids

Definitions

  • the invention relates to a process for the production of, in particular edible, oil with a high content of unsaturated fatty acids from a microalgae product.
  • Algal oil which can be produced from phototrophic and/or mixotrophic microalgae, is currently not suitable as an edible oil because it forms a black paste containing chlorophyll, pigments and other fat-soluble substances.
  • the fluidity and composition of the oil depends on the type of microalgae, the cultivation conditions and the harvesting process. So far, the microalgal biomass is pretreated by freeze drying or spray drying and then extracted by solvent extraction or supercritical fluid extraction.
  • the object of the invention is to create a method that allows the production of edible oil from microalgae oil.
  • this object is achieved in that the microalgae product is treated to form an intermediate product and is subjected to material separation to remove impurities, in which triglyceride is used as a carrier for the impurities.
  • the process can remove more than 80% of the contaminants from the microalgae product. Depending on how the process is carried out, more than 90%, possibly more than 95%, of the impurities can be removed.
  • a microalgae oil and/or a lipid extract is expediently used as the microalgae product.
  • the microalgae oil or the lipid extract is preferably obtained from phototrophic and/or mixotrophic microalgae.
  • Lipid extracts from green algae or from unicellular photosynthetic organisms have proven to be particularly well suited for carrying out the method.
  • the microalgae product preferably has an EPA content of at least 15% by weight, preferably at least 20% by weight EPA, particularly preferably at least 30% by weight.
  • the microalgae product has a pigment content, in particular a chlorophyll content, which is greater than 15000 mg/100 g, possibly greater than 20000 mg/100 g.
  • the microalgae product is treated by transesterification to form the intermediate. Conveniently, it is converted into an ethyl ester. This process step serves to prepare for increasing the concentration of omega-3 fatty acids, in particular EPA and/or DHA (docosahexaenoic acid), in the intermediate product.
  • omega-3 fatty acids in particular EPA and/or DHA (docosahexaenoic acid)
  • the microalgae product is chemically and/or enzymatically neutralized and/or phospholipids are removed therefrom.
  • the microalgae product is placed in a solvent for transesterification.
  • the microalgae product can be completely or at least partially soluble in water and/or in organic solvent, in particular in polar or non-polar liquids. For example, it is soluble in ethanol or hexane and partially soluble in water.
  • the transesterification reaction is preferably at temperatures ⁇ 100° C., particularly preferably ⁇ 80° C. and for a period of >30 min, preferably >60 min, particularly preferably >300 min.
  • the intermediate product in particular after transesterification, is subjected to material separation to remove impurities.
  • the triglyceride is expediently added to the intermediate product for the separation of substances, preferably after the transesterification.
  • an organic phase is separated from an inorganic phase of the intermediate product, preferably by mechanical separation, particularly preferably sedimentation and/or centrifugation.
  • a solvent in particular an organic solvent, is expediently added to the intermediate.
  • the mechanical separation can take place, for example, by means of sedimentation, separation or centrifugation.
  • the inorganic phase separated off in this way can be subjected to the above-described transesterification again, if necessary several times, in order to additionally separate out any organic phases remaining therein.
  • the organic phase is also separated off.
  • the residue forms the intermediate in the form of an ethyl ester.
  • the organic phase of the intermediate product is subjected to thermal material separation to remove impurities.
  • impurities can be formed by pigments, in particular by chlorophylls, phycoerythrins and/or carotenoids, for example carotenes and xanthophylls.
  • the triglyceride preferably a triglyceride oil, is expediently used in the thermal separation of substances.
  • the triglyceride as a carrier is particularly well suited for removing impurities, in particular pigments that darken the oil.
  • the thermal material separation for separating off the impurities is preferably carried out by means of distillation, preferably molecular distillation. It has proven particularly advantageous to carry out the molecular distillation at a pressure of from 0.001 to 1 mbar. This enables a particularly gentle treatment of the intermediate product, since the boiling point of its individual Components is reduced and the distillation can be carried out at a comparatively low temperature.
  • the intermediate is expediently mixed with the triglyceride, in particular triglyceride oil, in a mass ratio of between 1:0.1 to 1:15, preferably in a mass ratio of 1:0.5 to 1:7, particularly preferably in a mass ratio of 1:1 to 1:5, mixed.
  • the molecular distillation is expediently carried out in a temperature range between 100.degree. C. and 190.degree. C., preferably between 130.degree. C. and 175.degree.
  • the lipids remain preferentially in the ethyl ester forming the distillate and the triglycerides containing the impurities are separated.
  • the omega-3 fatty acid concentration in the intermediate product thus obtained is suitably increased by means of an additional omega-3 fatty acid concentration-enhancing process.
  • the process of increasing the concentration can be a distillation, in particular molecular distillation, an extraction using silver salt, a liquid chromatography, in particular supercritical fluid chromatography (SFC), and/or a precipitation, in particular using urea.
  • saturated fatty acids are separated from the intermediate product, in particular after thermal material separation, preferably by adding urea, in particular urea crystals.
  • the intermediate product is expediently subjected to thermal material separation for purification purposes in order to separate off remaining impurities from the process of increasing the concentration, in particular urea.
  • the intermediate can then be converted into a triglyceride by transesterification.
  • an antioxidant is added to the intermediate product after the saturated fatty acid has been separated or after said transesterification into the triglyceride.
  • the antioxidant serves to bleach the intermediate.
  • a naturally occurring antioxidant is used.
  • Clay which has already been used in various food production processes, has proven to be suitable for this purpose.
  • the oil has a pigment content, in particular a chlorophyll content, of ⁇ 4000 mg/100 g, preferably ⁇ 3000 mg/100 g.
  • An oil paste obtained from microalgae of the genus Nannochloropsis was used as the microalgae product for the method described below for producing an edible oil with a high content of omega-3 fatty acids.
  • the oil paste was analyzed using High Performance Liquid Chromatography (HPLC) and Gas Chromatography. The following contents were determined:
  • Triglycerides 29.2% by weight
  • Lipids free fatty acids, sphingolipids, glycolipids, galactolipids, phospholipids:
  • the oil paste has been enzymatically freed from phospholipids.
  • the solution was then cooled and, after cooling, cyclohexane and water were added to separate the organic phase from the inorganic phase.
  • the solution obtained is left to stand until a separation between the organic and inorganic phases forms.
  • the inorganic phase settles at the bottom so that the organic phase can be poured off.
  • the remaining inorganic phase can be treated again, if necessary several times, with cyclohexane.
  • the organic phases obtained are distilled and the ethyl ester is obtained as an intermediate product.
  • the oil produced by the transesterification and forming the intermediate has an ethyl ester concentration of 85% by weight. It has EPA in a concentration of 38% by weight and is colored dark green.
  • the intermediate product is then subjected to molecular distillation to remove impurities which, among other things, lead to the dark green colour.
  • the molecular distillation was carried out at 0.01 mbar in order to keep the boiling temperature of the components of the intermediate product low.
  • the oil constituting the intermediate product is mixed with a triglyceride oil in a mass ratio of 1:3 and the distillation is carried out at 150°C.
  • the lipids remain in the oil containing the ethyl ester and the impurities, particularly the pigments that previously colored the oil dark green, remain in the triglyceride, which is separated with the residual stream.
  • An oil which is yellow to orange in color is obtained as a further intermediate product.
  • the oil contains at least 90% by weight ethyl ester and has EPA at a concentration of 38% by weight.
  • a precipitation with urea is then carried out to reduce the content of saturated fatty acids.
  • the intermediate product is mixed with urea crystals and ethanol and the mixture is stirred at 80° C. for 90 minutes with continuous stirring.
  • the resulting solution is then cooled and filtered. To wash out urea residues, brine is added to the remaining solution.
  • An oil is now present as a further intermediate product, which has an EPA concentration of 67% by weight.
  • the intermediate can be subjected to a further molecular distillation.
  • the intermediate product was treated at a pressure of 0.03 mbar and at 160.degree.
  • clay has been added to the intermediate product as an antioxidant and at 65°C and under a pressure of 3 mbar remaining impurities and peroxides have been removed. The clay was then separated by filtration.
  • the end product obtained from the oil paste is an oil which has a concentration of 67% by weight of EPA and is suitable for human consumption.
  • Triglycerides 29.1% by weight
  • Lipids free fatty acids, sphingolipids, glycolipids, galactolipids, phospholipids:
  • the end product obtained from the oil paste is an oil which has an EPA concentration of 45% by weight.
  • the oil is also suitable as food for humans.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Microbiology (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Fats And Perfumes (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

L'invention concerne un procédé de production d'huile, plus particulièrement d'huile comestible, ayant une teneur élevée en acides gras insaturés, à partir d'un produit de micro-algues. Selon l'invention, le produit de micro-algues est traité, un produit intermédiaire est ainsi formé, et le produit intermédiaire est soumis à un processus de séparation de matériau pour éliminer les impuretés, des triglycérides étant utilisés dans le processus de séparation de matériau comme support pour les impuretés. Une huile et/ou un extrait lipidique de micro-algues est avantageusement utilisé(e) comme produit de micro-algues. Le produit de micro-algues est de préférence obtenu à partir de micro-algues, plus particulièrement de micro-algues photoautotrophes et/ou mixotrophes. Dans un mode de réalisation de l'invention, le produit de micro-algues est traité par transestérification afin de former le produit intermédiaire, le produit de micro-algues étant de préférence transformé en un ester éthylique. Dans un mode de réalisation de l'invention, une phase organique est séparée d'une phase inorganique du produit intermédiaire et la phase organique du produit intermédiaire est soumise à un processus de séparation de matériau pour éliminer les impuretés, les triglycérides étant utilisés dans le processus de séparation de matériau.
EP21766652.8A 2020-08-26 2021-08-26 Procédé de production d'huile à partir d'un produit de micro-algues Pending EP4203693A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
LU102019A LU102019B1 (de) 2020-08-26 2020-08-26 Verfahren zur Herstellung von Öl aus einem Mikroalgenerzeugnis
PCT/EP2021/073641 WO2022043453A1 (fr) 2020-08-26 2021-08-26 Procédé de production d'huile à partir d'un produit de micro-algues

Publications (1)

Publication Number Publication Date
EP4203693A1 true EP4203693A1 (fr) 2023-07-05

Family

ID=72896039

Family Applications (1)

Application Number Title Priority Date Filing Date
EP21766652.8A Pending EP4203693A1 (fr) 2020-08-26 2021-08-26 Procédé de production d'huile à partir d'un produit de micro-algues

Country Status (5)

Country Link
US (1) US20230357665A1 (fr)
EP (1) EP4203693A1 (fr)
CN (1) CN115956114A (fr)
LU (1) LU102019B1 (fr)
WO (1) WO2022043453A1 (fr)

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59113099A (ja) * 1982-12-20 1984-06-29 高尾　正保 高度不飽和油組成物
US7666234B2 (en) * 2004-10-20 2010-02-23 Council Of Scientific And Industrial Research Process for the preparation of fatty acid methyl ester from triglyceride oil by transesterification
MX2010000263A (es) * 2007-06-29 2010-03-11 Martek Biosciences Corp Produccion y purificacion de esteres de acidos grasos poliinsaturados.
FR2991337B1 (fr) * 2012-05-29 2016-09-02 Roquette Freres Procede continu d'enrichissement en esters ethyliques de dha d'une huile produite par des microalgues
WO2014152283A1 (fr) * 2013-03-15 2014-09-25 Heliae Development, Llc Transestérification directe de biomasse algale pour la synthèse d'esters éthyliques d'acide gras (eeag)
US20140288014A1 (en) * 2013-03-15 2014-09-25 Aurora Algae, Inc. Compositions of crude algal oil
CA3001018A1 (fr) * 2015-10-05 2017-04-13 Dsm Ip Assets B.V. Compositions d'huile et leurs procedes de production
JP2021521882A (ja) * 2018-04-20 2021-08-30 ナノ アルジー ソリューションズ アーゲー エイコサペンタエン酸オイル組成物を提供するための新規なプロセス

Also Published As

Publication number Publication date
CN115956114A (zh) 2023-04-11
US20230357665A1 (en) 2023-11-09
LU102019B1 (de) 2022-02-28
WO2022043453A1 (fr) 2022-03-03

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