WO2017050666A1 - Procédé de purification de glycérides d'acide gras, compositions dérivées de ces derniers, et leur utilisation - Google Patents

Procédé de purification de glycérides d'acide gras, compositions dérivées de ces derniers, et leur utilisation Download PDF

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Publication number
WO2017050666A1
WO2017050666A1 PCT/EP2016/072095 EP2016072095W WO2017050666A1 WO 2017050666 A1 WO2017050666 A1 WO 2017050666A1 EP 2016072095 W EP2016072095 W EP 2016072095W WO 2017050666 A1 WO2017050666 A1 WO 2017050666A1
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Prior art keywords
composition
glycerides
acids
equal
omega
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PCT/EP2016/072095
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English (en)
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Tiberio Bruzzese
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Tiberio Bruzzese
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Publication of WO2017050666A1 publication Critical patent/WO2017050666A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • 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
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/158—Fatty acids; Fats; Products containing oils or fats
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A23K50/80—Feeding-stuffs specially adapted for particular animals for aquatic animals, e.g. fish, crustaceans or molluscs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A23L33/12—Fatty acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/66—Phosphorus compounds
    • A61K31/661—Phosphorus acids or esters thereof not having P—C bonds, e.g. fosfosal, dichlorvos, malathion or mevinphos
    • A61K31/6615—Compounds having two or more esterified phosphorus acid groups, e.g. inositol triphosphate, phytic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/66—Phosphorus compounds
    • A61K31/683—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols
    • A61K31/685—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols one of the hydroxy compounds having nitrogen atoms, e.g. phosphatidylserine, lecithin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • 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
    • 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
    • C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
    • C11C1/04—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis
    • 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
    • C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
    • C11C1/04—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis
    • C11C1/045—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis using enzymes or microorganisms, living or dead
    • 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
    • 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
    • C11C3/02—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/805—Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
    • Y02A40/80—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in fisheries management
    • Y02A40/81—Aquaculture, e.g. of fish
    • Y02A40/818—Alternative feeds for fish, e.g. in aquacultures

Definitions

  • the glycerides substituted with polyunsaturated acyl groups are preferably subjected to hydrolysis or alcoholysis by enzymatic route, by means of lipases - also immobilized - selective for the structure of the acyl and for its position on the glycerol: it is thus possible to operate in very mild reaction conditions and - by virtue of the higher resistance to enzymatic cleavage of polyunsaturated acyl groups, compared to saturated and monounsaturated acyls - it is also possible to isolate compositions of glycerols that are still partially acylated and particularly enriched in polyunsaturated acids.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Food Science & Technology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Zoology (AREA)
  • Birds (AREA)
  • Emergency Medicine (AREA)
  • Animal Husbandry (AREA)
  • Mycology (AREA)
  • Nutrition Science (AREA)
  • Insects & Arthropods (AREA)
  • Dermatology (AREA)
  • Biochemistry (AREA)
  • Marine Sciences & Fisheries (AREA)
  • Fats And Perfumes (AREA)

Abstract

La présente invention concerne un nouveau procédé de purification de glycérides d'acide gras (mono- et/ou di- et/ou tri-glycérides), de n'importe quelle origine, et en particulier ceux caractérisés par une estérification au moins partielle avec des acides gras polyinsaturés à longue chaîne (PUFA). Ce procédé de purification consiste en traitement desdits glycérides avec une quantité d'urée convenant à leur complexation totale, et en la séparation ultérieure par filtration ou centrifugation du complexe d'incorporation d'urée à partir de la phase solvant contenant les autres produits qui sont structurellement non liés au glycéride, suivi de l'isolement du complexe des glycérides, qui sont purifiés et par conséquent exempts de nombreux polluants organiques "rémanents" (POP) de l'environnement, tels que les dibenzo-dioxines polychlorées et les dibenzo-furanes polychlorés, les biphényls polychlorés, les diphényl éthers polybromés, les hydrocarbures aromatiques polycycliques, et d'autres polluants qui sont habituellement présents et également extrêmement toxiques. L'invention concerne également les compositions purifiées des glycérides ainsi obtenus, ainsi que ceux pouvant dériver de ces derniers avec des procédés d'hydrolyse ou de transestérification, soit par la voie chimique soit enzymatique, ainsi que l'utilisation de telles compositions comme aliment, aliment pour utilisation médicale spéciale, complément alimentaire et diététique, et comme médicament.
PCT/EP2016/072095 2015-09-24 2016-09-19 Procédé de purification de glycérides d'acide gras, compositions dérivées de ces derniers, et leur utilisation WO2017050666A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITUB2015A003877A ITUB20153877A1 (it) 2015-09-24 2015-09-24 Metodo di purificazione di gliceridi di acidi grassi, composizioni che ne derivano, e loro uso
IT102015000055101 2015-09-24

Publications (1)

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WO2017050666A1 true WO2017050666A1 (fr) 2017-03-30

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3709817B1 (fr) * 2017-11-17 2022-11-16 Hill's Pet Nutrition, Inc. Compositions comprenant des acides gras oméga 3 polyinsaturés et à chaîne moyenne
EP4019930A4 (fr) * 2019-08-22 2023-09-13 Miura Co., Ltd. Procédé de purification d'huiles

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2700036A (en) * 1950-03-13 1955-01-18 Shell Dev Fractionation of fatty acid glycerides
WO2004007654A1 (fr) 2002-07-11 2004-01-22 Pronova Biocare As Procede et fluide de travail volatile reduisant les polluants environnementaux presents dans des graisses ou des huiles, supplement dietetique, et produit alimentaire pour animaux
WO2008133573A1 (fr) * 2007-04-26 2008-11-06 Patrick Adlercreutz Huile marine enrichie en acide gras polyinsaturé (pufa), comprenant l'acide eicosapentaénoïque (epa) et l'acide docosahexaénoïque (dha) et son procédé de fabrication
CN101575553A (zh) * 2009-06-05 2009-11-11 大连理工大学 一种低凝固点部分甘油酯的分级方法
WO2014068056A1 (fr) * 2012-11-02 2014-05-08 Pronova Biopharma Norge As Élimination de constituants indésirables à partir de compositions huileuses
US20140275594A1 (en) * 2011-07-14 2014-09-18 Soluciones Extractivas Alimentarias, S.L. New process for reducing pollutants in fats and oils and their derivatives
US20150126760A1 (en) * 2012-05-14 2015-05-07 Nippon Suisan Kaisha, Ltd. Highly unsaturated fatty acid or highly unsaturated fatty acid ethyl ester with reduced environmental pollutants, and method for producing same
WO2016150936A1 (fr) * 2015-03-26 2016-09-29 Tiberio Bruzzese Compositions purifiées d'acides gras polyinsaturés, leur méthode de préparation et leur utilisation

Patent Citations (10)

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US2700036A (en) * 1950-03-13 1955-01-18 Shell Dev Fractionation of fatty acid glycerides
WO2004007654A1 (fr) 2002-07-11 2004-01-22 Pronova Biocare As Procede et fluide de travail volatile reduisant les polluants environnementaux presents dans des graisses ou des huiles, supplement dietetique, et produit alimentaire pour animaux
EP1523541A1 (fr) 2002-07-11 2005-04-20 Pronova Biocare AS Procede et fluide de travail volatile reduisant les polluants environnementaux presents dans des graisses ou des huiles, supplement dietetique, et produit alimentaire pour animaux
US7732488B2 (en) 2002-07-11 2010-06-08 Pronova Biopharma Norge As Pharmaceutical composition comprising low concentrations of environmental pollutants
WO2008133573A1 (fr) * 2007-04-26 2008-11-06 Patrick Adlercreutz Huile marine enrichie en acide gras polyinsaturé (pufa), comprenant l'acide eicosapentaénoïque (epa) et l'acide docosahexaénoïque (dha) et son procédé de fabrication
CN101575553A (zh) * 2009-06-05 2009-11-11 大连理工大学 一种低凝固点部分甘油酯的分级方法
US20140275594A1 (en) * 2011-07-14 2014-09-18 Soluciones Extractivas Alimentarias, S.L. New process for reducing pollutants in fats and oils and their derivatives
US20150126760A1 (en) * 2012-05-14 2015-05-07 Nippon Suisan Kaisha, Ltd. Highly unsaturated fatty acid or highly unsaturated fatty acid ethyl ester with reduced environmental pollutants, and method for producing same
WO2014068056A1 (fr) * 2012-11-02 2014-05-08 Pronova Biopharma Norge As Élimination de constituants indésirables à partir de compositions huileuses
WO2016150936A1 (fr) * 2015-03-26 2016-09-29 Tiberio Bruzzese Compositions purifiées d'acides gras polyinsaturés, leur méthode de préparation et leur utilisation

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BREIVIK H: "Long-Chain Omega-3 Specialty Oils", 2007, THE OILY PRESS
BREIVIK: "Concentrates", 2007, pages: 111 - 130
BREIVIK: "Enzymatic processing of omega-3 specialty oils", 2007, pages: 141 - 164
DOUGLAS G. HAYES ET AL: "Urea-Based Fractionation of Seed Oil Samples Containing Fatty Acids and Acylglycerols of Polyunsaturated and Hydroxy Fatty Acids", JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY (JAOCS), vol. 77, no. 2, 1 February 2000 (2000-02-01), DE, pages 207 - 213, XP055271624, ISSN: 0003-021X *
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ZENNEGG M ET AL., ORGANOHALOGEN COMPOUNDS, vol. 68, 2006, pages 1967

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3709817B1 (fr) * 2017-11-17 2022-11-16 Hill's Pet Nutrition, Inc. Compositions comprenant des acides gras oméga 3 polyinsaturés et à chaîne moyenne
EP4019930A4 (fr) * 2019-08-22 2023-09-13 Miura Co., Ltd. Procédé de purification d'huiles

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