EP0255824B1 - Un procédé de fabrication de concentré d'huile de poisson raffinée - Google Patents

Un procédé de fabrication de concentré d'huile de poisson raffinée Download PDF

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Publication number
EP0255824B1
EP0255824B1 EP86906964A EP86906964A EP0255824B1 EP 0255824 B1 EP0255824 B1 EP 0255824B1 EP 86906964 A EP86906964 A EP 86906964A EP 86906964 A EP86906964 A EP 86906964A EP 0255824 B1 EP0255824 B1 EP 0255824B1
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EP
European Patent Office
Prior art keywords
fatty acid
concentrate
urea
cholesterol
compounds
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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.)
Expired - Lifetime
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EP86906964A
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German (de)
English (en)
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EP0255824A1 (fr
Inventor
Harald Breivik
Bernt Borretzen
Tore-Erling Jorgensen
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Norsk Hydro ASA
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Norsk Hydro ASA
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Priority to AT86906964T priority Critical patent/ATE49774T1/de
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • 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

Definitions

  • the present invention concerns a process for producing refined fish oil concentrate.
  • cholesterol and useful by products such as urea adducts of fatty acid compounds are produced, in addition to higher unsaturated fatty acids.
  • waste products from the fish refining industry contain usable products, among others fatty acids, cholesterol, proteins and enzymes. These are either fat-soluble or water-soluble. Such waste products are normally referred to as fish entrails.
  • the water-soluble portion containing proteins and enzymes may be separated from the fat-soluble portion.
  • the present invention concerns the fat-soluble portion of the waste products, but it can also use other refined fish oils such as occur for instance in the fish product industry. In the following these basic raw materials will be called «fish oil product”.
  • fatty acids the following may be specified as suitable for the medicinal purposes referred to : eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). Both fatty acids are w 3-fatty acids of the C-20 and C-22 acids..Their nomenclature according to the IUPAC system is:
  • docosahexaenoic acid 22 6 ⁇ 3
  • 20 and 22 indicate the number of C-atoms respectively in the molecule of the fatty acid, 5 and 6 the number of unsaturated bondings, and ⁇ 3 that the last unsaturated bonding is positioned at a distance of 3 carbon atoms from the w-position.
  • the fat soluble portion of cod entrails usually contains 10-25 % of the fatty acid compounds EPA and DHA, sometimes referred to herein as the essential fatty acid compounds, as well as 2-4 % cholesterol.
  • the remainder is mainly fatty acid compounds with lower unsaturation, such as pure fatty acids or their glycerides.
  • the purpose of the invention is to treat fish oil product so as to separate the fatty acid compounds EPA and DHA from cholesterol and other fatty acid compounds, and thereby from a concentrate containing high concentrations of EPA and DHA.
  • esters for instance as methyl or ethyl esters.
  • trans-esterification and esterification for instance with methanol for production of fatty acid methyl esters.
  • This basic material is well suited for further separation of EPA and DHA and cholesterol from the remaining less important fatty acid compounds.
  • Another patent, SU-A-950,393 describes a method for production of cholesterol from, for instance, fish waste products by hydrolysing the fatty acid compounds and converting them to soaps. These are then subjected to an extraction of trichlorethylene at room temperature, whereby the cholesterol is combined with the trichlorethylene and this compound is then subject to further separation.
  • GB-A-1,240 513 also concerns a separation technique by means of urea where the raw material consists of pure methyl and ethyl esters of the C 16 -C 18 fatty acids. Urea precipitation occurs in a neutral environment with a surplus of the relevant alcohol. The purpose is to be able to obtain a stronger concentration of y-linolenic acid.
  • the above-mentioned fatty acid esters do not contain any higher fatty acids other than C-18 in the form of stearic acid, oleic acid, linoleic acid and linolenic acid, which after the urea precipitation and separation of the urea adduct from the rest of the material has obtained a higher content of y-linolenic acid by means of chromotography.
  • the higher unsaturated fatty acid compounds 20 : 5 w3 and 22 : 6 w3 may be concentrated according to a method described in Japanese Patent Publication No. 59-071396 where the fatty acid compounds mentioned are extracted by means of polar solvents, such as acetone, methyl ethyl ketone, methanol, ethanol, and similar solvents, whereby a soluble and an insoluble extract are formed. Thereafter the extract is further processed to obtain essential fatty acid compounds.
  • polar solvents such as acetone, methyl ethyl ketone, methanol, ethanol, and similar solvents
  • the present invention provides a process for the production of a refined fish oil concentrate containing at least 20 % eicosapentaenoic acid (EPA) and at least 35 % docosehexaensoic (DHA) by weight, the remainder of the concentrate including other unsaturated fatty acid compounds, and the fatty acid compounds of the concentrate being mainly present as alkyl esters of lower alcohols, which comprises the steps of :
  • a one special feature of this process is that fatty acid compounds are not separated prior to precipitation of the urea adduct, but instead precipitate from the same non-uniform mixture of components like they are found in the basic raw material.
  • Another special feature is that the precipitation of the urea adduct takes place in an alkaline environment, and in such a way that the alkaline environment is created through applying the base only in catalytic quantities such as a catalytic agent for the trans-esterification of glycerides to methyl esters and not as a means of saponification of the fatty acids.
  • a third special feature is that the esterification and/or trans-esterification takes place at room temperature.
  • a result of esterification or trans-esterification at low temperature and in an environment with low alkalinity is that isomerization of the double bonds is avoided, which results in a more uniform product with no toxic effect. At the same time transconfigurations are avoided.
  • the remaining solution is thereafter extracted by means of a non-polar solvent, for example hexane, whereby the w3-fatty acids as well as cholesterol will be found in the non-polar phase.
  • the non-polar phase is treated to remove the solvent, as by being subjected to evaporation of the solvent under moderate conditions, for instance by means of vacuum distillation.
  • the remaining ⁇ 3-concentrate now contains all the cholesterol, and it becomes apparent that the cholesterol does not dissolve easily in this concentrate and will crystallize on cooling.
  • the M 3- concentrate which is left will contain 20-30 per cent EPA by weight and 35-50 % DHA by weight.
  • the remainder of the concentrate consists mainly of non-essential fatty acid compounds which are not important for our purpose.
  • FIG. 1 shows diagrammatically one way of carrying out the invention and where each block represents a step in the process and is marked with a reference number.
  • the flow. of the material to and from each block and between the blocks is marked by solid and dotted lines.
  • each material is characterized by a letter.
  • the basic material is fat and/or fatty acids from fish and especially fat and/or fatty acids obtained from the fish processing industry in connection with ensilage and or auto-catalysis processes, but the process may also be used with other forms of marine fat.
  • This fatty raw material is called fish oil product in the claims.
  • Such fat/fatty acids have a high content of saturated, unsaturated and polyunsaturated fatty acids with a chain length C 18, C 20 and C 22 as well as a certain amount of cholesterol, vitamins and other fat soluble products which are undefin- able, usually characterized as unsaponifiable, as well as fatty acid compounds with shorter chain lengths.
  • B alcohol with a low boiling point
  • methanol or ethanol for instance methanol, preferably methanol
  • C auxiliary compounds
  • Potassium hydroxide may be used as a catalytic agent, and in order to prevent oxidization, especially when heavy metals such as chromium, iron, cobalt, nickel and copper are present, small amounts of the sodium salt of ethylenediaminetetra-acetic acid (EDTA-Na 3 ) may be added.
  • EDTA-Na 3 ethylenediaminetetra-acetic acid
  • the esterification and trans-esterification take place under moderate conditions and stirring at about 20 °C for some hours.
  • the formation of alkyl esters is nearly complete when the ester product has changed its appearance from opalescent to clear.
  • the clear solution (D1) therefore contains alkyl esters of the fatty acids, glycerol, alkanol, as well as some water from the esterification of the free fatty acids.
  • the clear solution is then heated to a temperature of 55-90°, preferably 60-80°, most preferably 65-68 °C, whereafter a fixed amount of urea (E) and alkanol (B) is added and stirred in until everything is completely dissolved.
  • the amount of urea depends on the composition of the fatty acids so that if the raw material (A) contains 6-8 % EPA by weight, urea is added in the ratio 3 parts urea by weight to 1 part alkyl ester. In order to ensure that the components are completely soluble, 9 parts alkanol by weight is added.
  • the slightly alkaline filter mass (G) is saturated with hexane or other non-polar solvent, preferably hexane, and is extracted by means of this solvent through a known technique, as, for instance, by a continuing fluid-to-fluid counter current process, whereafter a further quantity of adduct of urea fatty ester may be crystallized.
  • hexane I
  • K residue
  • the hexane extract (1) which contains the alkyl- fatty esters of the polyunsaturated fatty acids 18 : 4003,20: 5 ⁇ 3-and22 : 6 00 3 as well as cholesterol as the most important components, is washed in dilute hydrochloric acid (L) in order to neutralize possible potassium soaps of the essential polyunsaturated fatty acids in the hexane extract.
  • the washing water is decanted.
  • Hexane (H) is thereafter removed by evaporation of the extract (1) so that a concentrate is produced which is free from solvents (N) and which contains the compounds that are essential for the invention, the fatty acid compounds EPA and DHA as well as cholesterol.
  • the dehydrated extract normally contains 20-30 % EPA, 35-45 % DHA, 10-20 % other polyunsaturated fatty acids, as well as 5-15 % cholesterol and undefined compounds, all by weight, but the exact composition referred to will depend on the type of fish used, the time of year the fish is caught, and the type and condition of the raw material.
  • alkyl fatty acid ester (N) is thereafter cooled to approx. minus 25 °C, whereafter cholesterol (O) is crystallized. This is centrifuged and/or filtered.
  • w3-concentrate (P) thus contains 20-35% EPA, 35-50 % DHA and 15-25 % of other polyunsaturated w3-fatty acid compounds (all by weight) as well as unsaturated fatty acid compounds which are not essential for the invention.
  • Product .(p) which contains the alkyl esters of the corresponding w3-fatty acids may be utilized as it is or if desired the concentration of EPA and DHA may be increased.
  • the product contains only small amounts of other fatty acids with the same chain length as EPA and DHA, it is well suited for separation of the essential fatty acids, EPA and DHA, by means of supercritical fluid extraction.
  • Another method for increasing the concentration is by means of preparative liquid chromatography by which method a more than 90 % purity of the essential fatty acids is obtained.
  • a hexane fraction (R) is precipitated in an upper layer which is separated.
  • the hexane fractions (R) contain free fatty acids as well as some of their alkyl esters and fairly high percentages of EPA and DHA, but also a fairly substantial portion of C 18-, C 20- and C 22-fatty acids with lower unsaturation.
  • This acid solution contains water, alcohol, alkanol, glycerol, urea and other products which may be retrieved by a separate process which is not described here.
  • the fatty acid components of the hexane fraction are increased by evaporating hexane (H) in a separate piece of equipment.
  • the remaining solution is esterified using lower alkanols, for instance methanol or ethanol by means of an appropriate catalytic agent (V) which for instance may be dehydrated hydrochloric acid, acetic acid chloride or boron-trichloride.
  • V catalytic agent
  • the resultant alkyl ester (D2) from the fatty acid components (T) from box 7 may be processed in various ways, for instance returned to box 2 for urea precipitation of the less unsaturated fatty acids.
  • the whole mixture was subjected to stirring for 15 hours at 20 °C in order to bring about a trans-esterification of the glycerides to methyl esters and esterification of the free fatty acids to methyl esters.
  • the urea adduct was separated from the solution by decanting and filtering according to an ordinary, known technique. Result : 100.1 kg urea adduct (F).
  • This filtrate (G) contained 003-polyunsaturated fatty acid methyl esters, cholesterol and a residue of unwanted fatty acid fractions with lower unsaturated C 18, C 20 and C 22 fatty acid methyl esters.
  • To this filtrate we added hexane for saturation, whereby a further amount of urea adduct (22 kg) could be separated.
  • This hexane-saturated solution was extracted in a counter-current with hexane so that the hexane extract (1) finally made up approx. 300 I. The remaining unextracted solution is called (K). The hexane extract was thereafter evaporated.
  • the yield of 003-fatty acid methyl ester concentrate 10.2 kilos.
  • the concentrate (N) which contained 23 % EPA, 41 % DHA and 8 % cholesterol, all by weight, was thereafter cooled to minus 25 °C, whereby pure cholesterol (O) crystallized and was removed by means of centrifuging during which time the residue in the centrifuge was washed with hexane with a lower temperature in order to remove the fatty acid methyl esters from the cholesterol crystals. Yield : 760 g pure cholesterol.
  • the concentrated filtrate (P) contained 25 % EPA-methy. lester, 43 % DHA-methylester by weight based on the fatty acid portion, and traces of cholesterol.
  • Another advantage with the invention is that it is possible to produce a urea adduct without following the cumbersome procedure of first producing the fatty acids, esterify these with alkanol and then separating them by means of the fractionated urea precipitation.

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

Claims (8)

1. Procédé pour la fabrication d'un concentré d'huile de poisson raffinée contenant au moins 20 % d'acide éicosapentaénoïque (EPA) et au moins 35% d'acide docosehexaensoïque (DHA) en poids, le reste du concentré comportant d'autres composés insaturés d'acides gras, et les composés d'acides gras du concentré étant principalement présents sous forme d'esters alkyliques d'alcools inférieurs, procédé qui comprend les étapes consistant à :
(a) estérifier et/ou trans-estérifier la fraction corps gras/acides gras de l'huile de poisson obtenue à la température ambiante avec un alcool inférieur dans un environnement alcalin contenant des quantités d'une base suffisantes seulement pour catalyser la réaction d'estérification et/ou de transestérification ;
(b) chauffer l'ester alkylique obtenu avec un excès d'urée dans un alcanol à une température comprise entre 55 et 90 °C;
(c) refroidir le produit obtenu dans l'étape (b) à 0 °C pour précipiter le produit d'addition urée- ester alkylique d'acides gras et ensuite séparer ce produit d'addition pour laisser une solution contenant principalement des esters de 3 acides gras et une partie insaponifiable ;
(d) séparer de la solution restante à l'issue de l'étape (c) les esters alkyliques de 3 acides gras et la partie insaponifiable, de préférence par extraction avec un solvant ;
(e) enlever tout solvant du mélange obtenu dans l'étape (d) ; et
(f) refroidir le concentré obtenu dans l'étape (e) pour cristalliser le cholestérol et précipiter tout composé insaponifiable indéfini, ce qui permet de laisser un concentré d'huile de poisson raffinée.
2. Procédé selon la revendication 1, dans lequel le concentré obtenu dans l'étape (f) est en outre traité de manière à augmenter la concentration de EPA et de DHA.
3. Procédé selon l'une quelconque des revendications 1 et 2, dans lequel, dans l'étape (b) les esters alkyliques d'acides gras sont traités avec de l'urée à une température comprise entre 60 et 80 °C, d'où il résulte que le produit d'addition urée-esters alkyliques d'acides gras dans la partie principale ne contient pas des composés des 3 acides gras et des composés insaponifiables.
4. Procédé selon l'une quelconque des revendications précédentes dans lequel, dans l'étape (d) la séparation est effectuée par extraction avec de l'hexane.
5. Procédé selon la revendication 4, dans lequel avant l'étape (e) l'extrait par l'hexane est purifié avec un acide dilué, de préférence avec de l'acide chlorhydrique.
6. Procédé selon l'une quelconque des revendications précédentes, dans lequel l'étape (f) est effectuée en refroidissant d'abord le concentré d'esters alkyliques de 3 acides gras, à une température non inférieure à -25 °C, d'où il résulte que le cholestérol est cristallisé, et ensuite à -50 °C, d'où il résulte que la partie restante des composés insaponifiables précipite.
7. Procédé selon l'une quelconque des revendications précédentes, dans lequel on utilise du méthanol dans l'étape (a), d'où il résulte que les composés d'acides gras du concentré obtenu sont principalement présents sous forme d'esters méthyliques.
8. Procédé selon l'une quelconque des revendications précédentes; dans lequel le concentré d'huile de poisson raffinée obtenu dans l'étape.(f) contient de 20 à 30 % de EPA et de 35 à 50 % de DHA.
EP86906964A 1985-12-19 1986-11-21 Un procédé de fabrication de concentré d'huile de poisson raffinée Expired - Lifetime EP0255824B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT86906964T ATE49774T1 (de) 1985-12-19 1986-11-21 Ein verfahren zur herstellung von raffiniertem fischoelkonzentrat.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NO855147 1985-12-19
NO855147A NO157302C (no) 1985-12-19 1985-12-19 Fremgangsmaate for fremstilling av et fiskeoljekonsentrat.

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EP0255824A1 EP0255824A1 (fr) 1988-02-17
EP0255824B1 true EP0255824B1 (fr) 1990-01-24

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EP (1) EP0255824B1 (fr)
AR (1) AR242111A1 (fr)
AU (1) AU6621186A (fr)
CA (1) CA1303416C (fr)
DD (1) DD261805A1 (fr)
DE (1) DE3668467D1 (fr)
IE (1) IE59171B1 (fr)
IS (1) IS1425B6 (fr)
MA (1) MA20840A1 (fr)
MX (1) MX168698B (fr)
NO (1) NO157302C (fr)
NZ (1) NZ218500A (fr)
PT (1) PT83991B (fr)
WO (1) WO1987003899A1 (fr)
ZA (1) ZA868927B (fr)

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US7678930B2 (en) 2002-07-11 2010-03-16 Pronova Biopharma Norge As Process for decreasing the amount of cholesterol in a marine oil using a volatile working fluid
US7718698B2 (en) 2002-07-11 2010-05-18 Pronova Biopharma Norge As Process for decreasing environmental pollutants in an oil or a fat
US9234157B2 (en) 2011-07-06 2016-01-12 Basf Pharma Callanish Limited SMB process
US9260677B2 (en) 2011-07-06 2016-02-16 Basf Pharma Callanish Limited SMB process
WO2016028235A1 (fr) * 2014-08-18 2016-02-25 Chiang Mai University Système et procédé d'extraction et/ou de concentration
US9315762B2 (en) 2011-07-06 2016-04-19 Basf Pharma Callanish Limited SMB process for producing highly pure EPA from fish oil
US9370730B2 (en) 2011-07-06 2016-06-21 Basf Pharma Callanish Limited SMB process
EP3789476A1 (fr) 2015-05-13 2021-03-10 Epax Norway AS Acides gras polyinsaturés à très longue chaîne fabriqués à partir d'huiles naturelles

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* Cited by examiner, † Cited by third party
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GB8819110D0 (en) * 1988-08-11 1988-09-14 Norsk Hydro As Antihypertensive drug & method for production
CA2077914C (fr) * 1990-03-12 2000-05-30 Einar Sola Procede d'enrichissement de matieres grasses en acides gras polyinsatures et en phospholipides, et utilisation de telles matieres grasses enrichies
SE9303446D0 (sv) * 1993-10-20 1993-10-20 Trikonex Ab A novel urea fractionation process
GB9404483D0 (en) * 1994-03-08 1994-04-20 Norsk Hydro As Refining marine oil compositions
TW425285B (en) 1996-06-10 2001-03-11 Viva America Marketing Inc Fish oil and garlic nutritive supplement
US6313167B1 (en) 1997-06-16 2001-11-06 Nippon Suisan Kaisha Ltd. Composition having capability of removing risk factor during exercise
NO309795B1 (no) * 1998-07-01 2001-04-02 Norsk Hydro As FremgangsmOte for O stabilisere oljer samt anvendelse derav, fremgangsmOte for O stabilisere pigmenter, og fremgangsmOte for fremstilling av for
IT1308613B1 (it) 1999-02-17 2002-01-09 Pharmacia & Upjohn Spa Acidi grassi essenziali nella prevenzione di eventi cardiovascolari.
NO311041B1 (no) * 1999-12-22 2001-10-01 Norsk Hydro As Stabilisering av pigmenter og flerumettede oljer og oljekonsentrater
US6395778B1 (en) 2000-01-11 2002-05-28 Omegatech, Inc. Process for making an enriched mixture of polyunsaturated fatty acid esters
AT414205B (de) 2000-06-20 2006-10-15 Vis Vitalis Lizenz & Handels Verfahren zur herstellung von ungesättigtem fettsäure-trockenkonzentrat
ITMI20010129A1 (it) 2001-01-25 2002-07-25 Pharmacia & Upjohn Spa Acidi grassi essenziali nella terapia di insufficienza cardiaca e scompenso cardiaco
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CA2611324C (fr) 2005-06-07 2017-02-14 Ocean Nutrition Canada Limited Micro-organismes eucaryotes pour produire des lipides et des antioxydants
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WO2008129358A2 (fr) 2006-08-01 2008-10-30 Ocean Nutrition Canada Ltd. Microbes produisant des huiles et procedes de modification associes
RU2014146265A (ru) 2009-12-30 2015-07-10 Басф Фарма (Калланиш) Лимитед Способ хроматографического разделения с псевдодвижущимся слоем
ITMI20102297A1 (it) 2010-12-15 2012-06-16 Prime Europ Therapeuticals Procedimento per stabilizzare acidi grassi poliinsaturi per mezzo di idruri metallici
US8889895B2 (en) * 2011-03-08 2014-11-18 Cognis Ip Management Gmbh Process for the distillation of fatty acid esters
GB201111594D0 (en) 2011-07-06 2011-08-24 Equateq Ltd New improved process
GB201300354D0 (en) 2013-01-09 2013-02-20 Basf Pharma Callanish Ltd Multi-step separation process
AU2014229307B2 (en) 2013-03-13 2017-08-31 Dsm Nutritional Products Ag Engineering microorganisms
US9428711B2 (en) 2013-05-07 2016-08-30 Groupe Novasep Chromatographic process for the production of highly purified polyunsaturated fatty acids
EP3118186B1 (fr) 2013-12-11 2022-02-09 Novasep Process Installation chromatographique de production d acides gras polyinsatures
BR112016015718B1 (pt) 2014-01-07 2021-12-07 Novasep Process Solutions Processo de purificação de aminoácidos aromáticos
US9163198B2 (en) * 2014-01-17 2015-10-20 Orochem Technologies, Inc. Process for purification of EPA (eicosapentanoic acid) ethyl ester from fish oil
AR104042A1 (es) 2015-03-26 2017-06-21 Mara Renewables Corp Producción de alta densidad de biomasa y aceite utilizando glicerol en bruto
US10821090B2 (en) 2015-03-26 2020-11-03 Tiberio Bruzzese Purified compositions of polyunsaturated fatty acids, their preparation method and their use
US9951326B2 (en) 2015-07-13 2018-04-24 MARA Renewables Corporation Enhancing microbial metabolism of C5 organic carbon
US10851395B2 (en) 2016-06-10 2020-12-01 MARA Renewables Corporation Method of making lipids with improved cold flow properties
WO2019053744A1 (fr) 2017-09-14 2019-03-21 Fermenta Biotech Limited Processus amélioré d'extraction de cholestérol à partir de résidus de déchets d'huile de poisson
US10196586B1 (en) * 2018-02-14 2019-02-05 Golden Omega S.A. Feed ingredient

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1176916B (it) * 1984-10-10 1987-08-18 Elvira Pistolesi Composizione farmaceutica o dietetica ad elevata attivita' antitrombotica e antiarteriosclerotica

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7678930B2 (en) 2002-07-11 2010-03-16 Pronova Biopharma Norge As Process for decreasing the amount of cholesterol in a marine oil using a volatile working fluid
US7718698B2 (en) 2002-07-11 2010-05-18 Pronova Biopharma Norge As Process for decreasing environmental pollutants in an oil or a fat
US7732488B2 (en) 2002-07-11 2010-06-08 Pronova Biopharma Norge As Pharmaceutical composition comprising low concentrations of environmental pollutants
US9234157B2 (en) 2011-07-06 2016-01-12 Basf Pharma Callanish Limited SMB process
US9260677B2 (en) 2011-07-06 2016-02-16 Basf Pharma Callanish Limited SMB process
US9315762B2 (en) 2011-07-06 2016-04-19 Basf Pharma Callanish Limited SMB process for producing highly pure EPA from fish oil
US9370730B2 (en) 2011-07-06 2016-06-21 Basf Pharma Callanish Limited SMB process
WO2016028235A1 (fr) * 2014-08-18 2016-02-25 Chiang Mai University Système et procédé d'extraction et/ou de concentration
EP3789476A1 (fr) 2015-05-13 2021-03-10 Epax Norway AS Acides gras polyinsaturés à très longue chaîne fabriqués à partir d'huiles naturelles

Also Published As

Publication number Publication date
NZ218500A (en) 1989-03-29
NO157302B (no) 1987-11-16
DD261805A1 (de) 1988-11-09
MA20840A1 (fr) 1987-07-01
WO1987003899A1 (fr) 1987-07-02
DE3668467D1 (de) 1990-03-01
CA1303416C (fr) 1992-06-16
MX168698B (es) 1993-06-04
PT83991A (en) 1987-01-01
IS1425B6 (is) 1990-03-28
EP0255824A1 (fr) 1988-02-17
IE863064L (en) 1987-06-19
NO157302C (no) 1988-02-24
AR242111A1 (es) 1993-03-31
NO855147L (no) 1987-06-22
ZA868927B (en) 1987-08-26
AU6621186A (en) 1987-07-15
PT83991B (pt) 1989-01-17
IE59171B1 (en) 1994-01-12
IS3159A7 (is) 1987-06-20

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