EP0565673B1 - Verfahren zur verbesserung eines glycerolysierten öl - Google Patents

Verfahren zur verbesserung eines glycerolysierten öl Download PDF

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Publication number
EP0565673B1
EP0565673B1 EP92922210A EP92922210A EP0565673B1 EP 0565673 B1 EP0565673 B1 EP 0565673B1 EP 92922210 A EP92922210 A EP 92922210A EP 92922210 A EP92922210 A EP 92922210A EP 0565673 B1 EP0565673 B1 EP 0565673B1
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EP
European Patent Office
Prior art keywords
oil
temperature
crystals
crystallization
glycerolysed
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.)
Expired - Lifetime
Application number
EP92922210A
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English (en)
French (fr)
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EP0565673A1 (de
Inventor
Jean-Marie Klein
Joel Denis
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.)
Gattefosse SA
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Gattefosse SA
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Filing date
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Application filed by Gattefosse SA filed Critical Gattefosse SA
Publication of EP0565673A1 publication Critical patent/EP0565673A1/de
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Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
    • C11B7/0075—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of melting or solidifying points

Definitions

  • the invention relates to a method for improving a glycerolysed oil.
  • glycerolysed oils are obtained by glycerolysis in the presence of alkaline catalysts.
  • these oils have a residual level of glycerol at most equal to one percent (1%).
  • glycosylated oil means a natural oil, of vegetable or animal origin, having undergone an alcoholysis treatment with glycerol, or a direct esterification of its fatty acids on glycerol.
  • glycerolysed oils are essentially characterized by the fact that they consist of a majority mixture of mono- and di-esters of glycerol and of a smaller amount of triesters. These glycerolysed oils must contain at least 90% by weight of glycerides (FDA-21 CFR requirements - Chapter I - ⁇ 184.1505), and have a high proportion (at least 50% and in practice of the order of 80%) of unsaturated fatty acids.
  • oils there may be mentioned oils of vegetable origin, such as those of corn, sunflower (high and low linoleic acid content), safflower (high and low linoleic acid content), palm (fractionated or not) , peanut or rapeseed, or of animal origin, such as tallow.
  • the invention overcomes these drawbacks. It relates to a process for improving these glycerolysed oils, and more particularly aims to extract the portion capable of crystallizing by a physical process, so that the oils treated in this way can meet the requirements of the pharmaceutical industry.
  • the invention relates more particularly to a process which makes it possible to obtain a glycerolysed oil, liquid and clear for at least three days at 15 ° C., which we did not previously know how to obtain.
  • this process can be implemented in a single phase, one can also use a process in several successive phases. It is therefore important that the characteristic temperature of the treatment be lower from one phase to the next, and that the temperature of the last phase be between 0 and 15 ° C.
  • end of crystallization temperature is meant the temperature at which the thermal cycle used for the partial crystallization of the product stops, which in fact takes place over a range of temperatures and at which the separation steps begin and are carried out.
  • a glycerolized corn oil having a residual glycerol level of less than one percent (1%), used by the Applicant under the name MAISINE are used.
  • This oil contains 37.0% (by mass) of monoglycerides, 48.0% of diglycerides and 14.5% of triglycerides, and the complement of glycerol and free fatty acids.
  • the fatty acids constituting these glycerides represent 10.1% of C 16 fatty acid (palmitic acid), 2.6% of C 18 (stearic acid), 29.6% of C 18: 1 (oleic acid), 54 , 2% C 18: 2 (linoleic acid), 1.1% C 18: 3 (linolenic acid), the supplement in higher fatty acids.
  • this glycerolysed oil When this glycerolysed oil is stored at room temperature, an appreciable quantity of white crystals is formed which deposit on the bottom, then grow very quickly until forming spherulites of very variable diameters between 10 and 500 microns, very difficult to separate. After three days, this glycerolysed oil is partially solidified.
  • This glycerolysed oil is then heated in an oven for one hour at 80 ° C. until total disappearance of the crystals formed, but also disappearance of the thermal past of this sample.
  • the hot glycerolysed oil is then placed in a three-liter beaker surrounded by a bath thermostatically controlled at 20 ° C.
  • the mixture is stirred slowly by means of a frame formed by three vertical bars spaced five centimeters apart, interconnected by two horizontal bars spaced ten centimeters apart.
  • the speed of rotation of this winterization agitator is 25 revolutions / minute. It is thus stirred at 20 ° C for forty-eight hours.
  • the pasty liquid obtained is then transferred to six 300 ml centrifuge bowls and centrifuged at this same temperature of 20 ° C for ten minutes at 4000 rpm, or 3500 G.
  • the supernatant liquid phase is extracted by transfer and this liquid phase is recovered. The remaining base sticks to the walls. A liquid phase yield of about 50% is obtained.
  • This liquid phase is again heated to 80 ° C. for one hour, then it is crystallized at 5 ° C. (end of crystallization temperature) for forty-eight hours using the same apparatus, then it is still centrifuged at this temperature of 5 °. C for ten minutes at 3500 G.
  • a new liquid phase is extracted (70% yield - a total yield of 35%).
  • the fractionated glycerolysed oil obtained is perfectly clear at 15 ° C for at least four days and meets the legal definition of glycerolysed corn oil. It is completely inert vis-à-vis the active ingredients, and the medication of the excipient compound added to the active ingredient, remains constant over time in given volume, since this medication is not disturbed by the appearance of parasitic crystals, this that we didn't know how to do before.
  • the glycerolysed oil treated in this way makes it easier for the active ingredients to be available per os. As already said, this oil is perfectly suited as an excipient for medication intended to be administered orally.
  • Example 1 is repeated, but replacing the two separation-centrifugation stages with two stages of filtration through a 50 micron mesh screen, at a relative pressure of 0.5 bars.
  • Example 1 is repeated, replacing the glycerolized corn oil with glycerolized sunflower oil, having a free glycerol level of less than 2.5%.
  • Glycerolysed corn oil contains 37.0% (by mass) of monoglycerides; 47.7% diglycerides and 14.7% triglycerides and the complement in glycerol and free fatty acids.
  • the fatty acids constituting these glycerides represent 10.5% of C 16 fatty acid (palmitic acid); 2.1% C 18 (stearic acid); 29.1% C 18: 1 (oleic acid); 54.7% C 18: 2 (linoleic acid); 1.0% C 18: 3 (linolenic acid); the complement in higher fatty acids.
  • the complement consists of higher fatty acids.
  • this glycerolysed oil When stored at room temperature, a large amount of white crystals are formed in this glycerolysed oil, mainly consisting of saturated glycerides, in particular glycerol monopalmitate. Two days after storage, the glycerolysed oil is cloudy and two weeks after storage at room temperature, the glycerolysed oil is partially solidified and a large white deposit is located in the bottom of the barrel, which makes its use difficult.
  • This glycerolysed oil is brought to 80 ° C for about thirty minutes to erase its thermal past, then is gradually cooled in stages by constantly adjusting the temperature difference between the oil and the heat transfer fluid.
  • the refrigerant has a temperature three degrees (3 ° C) lower than that of oil.
  • the oil is then cooled from 26 ° C to 19 ° C in 13 hours, still with stirring but adjusted to 15 revolutions / minute, and the temperature of the refrigerant is one degree (1 ° C) lower than that of oil.
  • the oil is kept at the end of crystallization temperature of eight degrees (8 ° C).
  • the solid phase consists of spherulites, with an average diameter of 350 microns, bathed in a liquid phase. It is filtered on a membrane filter press placed in a cold room, to separate the spherulites from the oil which it is sought to recover. This separation is facilitated by the homogeneous diameter of these spherulites.
  • the supply of the filter is obtained by a variable flow pump regulated so that the supply pressure is around 2 relative bars.
  • a perfectly clear liquid phase (fractionated glycerolysed oil) is obtained, having the following characteristics: 30.9% monoglycerides (compared to 37.0%) at the start, 52.3% diglycerides (versus 47.7%) 16.3% triglycerides (versus 14.7%).
  • Composition of fatty acids in glyceride fractions In monoglycerides: 3.2% of C 16 (versus 12.5%), 0.6% of C 18 (compared to 2.2%), 29.8% C 18: 1 (against 28.9%), 64.4% of C 18: 2 (versus 55.1%) In diglycerides: 10.2% of C 16 (versus 12.5%), 1.9% of C 18 (compared to 2.2%), 29.1% C 18: 1 (against 28.4%), 56.8% C 18: 2 (versus 55.4%). In triglycerides: 11.2% of C 16 (versus 13.6%), 2.2% of C 18 (versus 2.7%), 28.9% C 18: 1 (against 29.2%), 56.2% C 18: 2 (versus 52.9%).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth 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)
  • Edible Oils And Fats (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (7)

  1. Verfahren zur Herstellung eines glycerolysierten Öls mit einer verbesserten Kristallisationsstabilität, wobei das Öl reicher an Monoglyceriden und Diglyceriden als an Triglyceriden ist,
    dadurch gekennzeichnet, daß das Verfahren besteht aus:
    - Erwärmen des glycerolysierten Öls auf 80°C, dann Aufrechterhalten dieser Temperatur für eine Stunde bis die Kristalle, die sich gebildet haben könnten, verschwunden sind;
    - anschließend Kristallisieren des Öls durch Abkühlen unter langsamer Bewegung für acht bis zweiundsiebzig Stunden, bis eine Endtemperatur der Kristallisation von zwischen 0 und 15°C erreicht wird;
    - und schließlich Trennen der gebildeten Kristalle von dem erhaltenen Öl bei der gleichen Endtemperatur der Kristallisation, um ein stabiles gereinigtes glycerolysiertes Öl zu erhalten.
  2. Verfahren gemäß Anspruch 1,
    dadurch gekennzeichnet, daß das Verfahren besteht aus:
    - in einem ersten Schritt:
    - Erwärmen des Öls auf 80°C bis die Kristalle, die sich gebildet haben könnten, verschwunden sind;
    - dann Kristallisieren des Öls unter langsamer Bewegung für acht bis zweiundsiebzig Stunden, bis eine Endtemperatur der Kristallisation von zwischen 15 und 25°C erreicht wird;
    - anschließend Trennen der gebildeten Kristalle immer bei einer Temperatur von zwischen 15 und 25°C;
    - anschließend in einem zweiten Schritt:
    - erneutes Erwärmen des erhaltenen Öls auf 80°C, bis die restlichen Kristalle aufgelöst sind;
    - Wiederholen des Kristallisationsschrittes, aber bei einer Endtemperatur der Kristallisation von zwischen 0 und 15°C und auf jeden Fall unter der Endtemperatur der Kristallisation des ersten Schrittes;
    - und schließlich erneutes Trennen der gebildeten Kristalle bei dieser zweiten Endtemperatur der Kristallisation.
  3. Verfahren gemäß einem der Ansprüche 1 und 2,
    dadurch gekennzeichnet, daß die Kristallisation durch "Winterisation" bewirkt wird.
  4. Verfahren gemäß einem der Ansprüche 1 bis 3,
    dadurch gekennzeichnet, daß die Trennung der Kristalle durch Zentrifugation bei einer Temperatur von höchstens 15°C, aber höher als 0°C, für eine Dauer von fünf bis sechzig Minuten mit Beschleunigungen von 500 bis 12000 G bewirkt wird.
  5. Verfahren gemäß einem der Ansprüche 1 bis 3,
    dadurch gekennzeichnet, daß die Trennung der Kristalle durch Filtration bei einer Temperatur von zwischen 0 und 15°C über ein Filtriersieb mit einer Siebweite von 10 bis 500 µm unter einem relativen Druck niedriger als 5 bar bewirkt wird.
  6. Verfahren gemäß Anspruch 4,
    dadurch gekennzeichnet, daß der Zentrifugationsschritt mit einem Filtrationsschritt gemäß Anspruch 5 verbunden wird.
  7. Verfahren gemäß einem der Ansprüche 5 und 6, angewendet an ein Maisöl,
    dadurch gekennzeichnet, daß die Endtemperatur der Kristallisation zwischen 8 und 10°C beträgt.
EP92922210A 1991-10-31 1992-10-08 Verfahren zur verbesserung eines glycerolysierten öl Expired - Lifetime EP0565673B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9113715 1991-10-31
FR9113715A FR2683225B1 (fr) 1991-10-31 1991-10-31 Procede pour ameliorer une huile glycerolysee.
PCT/FR1992/000939 WO1993009211A1 (fr) 1991-10-31 1992-10-08 Procede pour ameliorer une huile glycerolysee

Publications (2)

Publication Number Publication Date
EP0565673A1 EP0565673A1 (de) 1993-10-20
EP0565673B1 true EP0565673B1 (de) 1997-08-27

Family

ID=9418694

Family Applications (1)

Application Number Title Priority Date Filing Date
EP92922210A Expired - Lifetime EP0565673B1 (de) 1991-10-31 1992-10-08 Verfahren zur verbesserung eines glycerolysierten öl

Country Status (8)

Country Link
US (1) US5441738A (de)
EP (1) EP0565673B1 (de)
JP (1) JPH06504574A (de)
AT (1) ATE157391T1 (de)
CA (1) CA2096744A1 (de)
DE (1) DE69221848D1 (de)
FR (1) FR2683225B1 (de)
WO (1) WO1993009211A1 (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6262022B1 (en) 1992-06-25 2001-07-17 Novartis Ag Pharmaceutical compositions containing cyclosporin as the active agent
WO1993023010A1 (en) 1992-05-13 1993-11-25 Sandoz Ltd. Ophthalmic compositions containing a cyclosporin
ES2168271T3 (es) 1992-09-25 2002-06-16 Novartis Ag Composiciones farmaceuticas que contienen ciclosporinas.
AT404137B (de) * 1994-04-08 1998-08-25 Bundesanstalt Fuer Landtechnik Verfahren zur trennung von fettsäureestergemischen
DE29824679U1 (de) 1997-01-30 2002-03-28 Novartis Ag Pharmazeutische Zusammensetzungen
ES2573539T3 (es) * 2005-03-21 2016-06-08 Teva Czech Industries S.R.O. Inhibidor de la cristalización y su uso en cápsulas de gelatina
US10059906B2 (en) * 2016-07-20 2018-08-28 MARA Renewables Corporation Solventless winterization of microbial oil

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB616190A (en) * 1945-11-06 1949-01-18 Procter & Gamble Improvements in application of low temperature inter-esterification or alcoholysis to glycerides
US3012890A (en) * 1960-02-03 1961-12-12 Herbert J Dutton Synthetic cocoa butter substitute
JPS6033878B2 (ja) * 1977-12-01 1985-08-05 味の素株式会社 油脂類の自然分別法
US4272447A (en) * 1979-12-26 1981-06-09 The Procter & Gamble Company Crude edible oil wax removal process
FR2482976A1 (fr) * 1980-05-22 1981-11-27 Lesieur Cotelle Associes Sa Procede de traitement des huiles vegetales pour l'amelioration de leur stabilite a froid
US4471961A (en) * 1982-09-15 1984-09-18 Pepsico, Inc. Golf club with bulge radius and increased moment of inertia about an inclined axis
CH658163A5 (fr) * 1983-10-07 1986-10-31 Nestle Sa Procede de production de fractions comestibles de matieres grasses et leur utilisation.
GB8430344D0 (en) * 1984-11-30 1985-01-09 Unilever Plc Fractionating triglyceride oil
JP2560290B2 (ja) * 1986-06-27 1996-12-04 日新電機株式会社 遠方監視制御装置の被制御所用装置
JPH0749592B2 (ja) * 1986-08-04 1995-05-31 不二製油株式会社 油脂物質の乾式分別法
LU86602A1 (fr) * 1986-09-22 1988-04-05 Tirtiaux Fractionnement Procede et installation de fractionnement par cristallisation de matieres grasses
JPS642675A (en) * 1987-02-23 1989-01-06 Hitachi Metals Ltd Iron head of low gravity center structure

Also Published As

Publication number Publication date
WO1993009211A1 (fr) 1993-05-13
FR2683225A1 (fr) 1993-05-07
CA2096744A1 (fr) 1993-05-01
ATE157391T1 (de) 1997-09-15
DE69221848D1 (de) 1997-10-02
EP0565673A1 (de) 1993-10-20
US5441738A (en) 1995-08-15
FR2683225B1 (fr) 1993-12-31
JPH06504574A (ja) 1994-05-26

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