EP0224798A1 - Use of alkyl glycosides in the separation of fatty acid ester mixtures - Google Patents

Use of alkyl glycosides in the separation of fatty acid ester mixtures Download PDF

Info

Publication number
EP0224798A1
EP0224798A1 EP86116026A EP86116026A EP0224798A1 EP 0224798 A1 EP0224798 A1 EP 0224798A1 EP 86116026 A EP86116026 A EP 86116026A EP 86116026 A EP86116026 A EP 86116026A EP 0224798 A1 EP0224798 A1 EP 0224798A1
Authority
EP
European Patent Office
Prior art keywords
fatty acid
wetting agent
weight
alkyl
acid ester
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.)
Granted
Application number
EP86116026A
Other languages
German (de)
French (fr)
Other versions
EP0224798B1 (en
Inventor
Richard Schuh
Manfred Dr. Biermann
Alfred Dr. Struve
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0224798A1 publication Critical patent/EP0224798A1/en
Application granted granted Critical
Publication of EP0224798B1 publication Critical patent/EP0224798B1/en
Expired legal-status Critical Current

Links

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
    • C11B7/0091—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils non-solvents, e.g. water wherein the fat or oil is dispersed account a more washing out of fractions is not taken into
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives

Definitions

  • the invention relates to separations of fatty acid ester mixtures occurring in fats and oils by the known crosslinking process using aqueous wetting agent solutions containing alkylglycosides.
  • Natural fats and oils differ in chain length and degree of saturation of their fatty acid ester components and thus also in their physical properties.
  • the melting points of saturated fatty acid esters are above room temperature, while unsaturated fatty acid esters are liquid at room temperature.
  • the separation of fats into solid and liquid components represents a separation into more saturated and more unsaturated parts.
  • a separation into solid and liquid constituents can be achieved in an advantageous manner by the so-called cross-linking process, a separation in the presence of aqueous solutions containing wetting agents, the solid portions being absorbed by the aqueous phase by wetting.
  • JP 57/197 discloses mixtures of fatty alcohol sulfate and sorbitan fatty acid esters as wetting agents for separating fatty acids and fats into solid and liquid constituents.
  • the abstracts of Chemical Abstracts CA 100 , 123 162v and CA 96 , 144 899e describe the cross-linking of fats using wetting agents containing sucrose fatty acid esters or mixtures of sorbitan or polyoxyethylene sorbitan fatty acid esters and fatty acid salts.
  • sorbitan fatty acid esters can be subject to hydrolysis in alkaline media, in particular at higher temperatures, proves disadvantageous when using sorbitan fatty acid esters.
  • the object of the invention was to provide wetting agent solutions which show equally good separation effects of fats and oils in solid and liquid components as wetting agent solutions of the prior art, but which contain hydrolysis-stable substances which are produced from renewable raw materials.
  • aqueous glyceride-containing aqueous wetting agent solutions are particularly suitable for achieving the object according to the invention, although alkyl glycosides and their wetting agent properties have been known for years.
  • the invention accordingly relates to the use of alkyl glycosides with up to 24 carbon atoms in the alkyl chain as wetting agents in aqueous wetting agent solutions for separating fatty acid ester mixtures into solid and liquid constituents by the known crosslinking process.
  • wetting agent solutions containing alkylglycoside have the great advantage over wetting agent solutions from the prior art in that they are hydrolysis-stable and that the alkylglycosides contained in them represent a known class of substance which can be prepared from renewable raw materials by conventional methods of organic synthesis.
  • the alkyl glycosides used according to the invention are derived in particular from fatty alcohols and sugars.
  • Alkyl glycosides with a C6-, C8-, C10-, C12-, C16-, C16- and / or C18-alkyl radical are preferred which are straight-chain or branched, saturated but also mono- or poly-olefinically unsaturated and have, for example, up to 3 double bonds can, or mixtures of such compounds.
  • Alkyl glycosides whose alkyl or alkenyl radical contains 10 to 16 carbon atoms are particularly suitable.
  • both alkyl monoglycosides in which a cyclic sugar residue is bonded to the alcohol are suitable, but also oligomers with preferably up to 8, in particular up to 3, glycosidically bonded sugar residues, for example glucose or maltose residues.
  • the number of sugar residues is a statistical mean, which is based on the distribution customary for these compounds.
  • Alkyl glycosides based on C12 to C14 fatty alcohols and with up to 2.5 glycoside residues can be particularly suitable.
  • aqueous wetting agent solutions containing alkylglycoside contain non-surface-active electrolytes which are inert towards the starting materials.
  • non-surface-active electrolytes include, for example, the water-soluble chlorides, sulfates and nitrates of 1- to 3-membered metals, preferably the alkali, alkaline earth and earth metals.
  • alkyl glycoside-containing aqueous wetting agent solutions are preferably to be understood as meaning electrolyte-containing alkyl glycoside-containing aqueous wetting agent solutions.
  • the effect of the aqueous glyceride-containing wetting agent solutions can be improved by adding unsaturated natural fatty acid salts with more than 14 carbon atoms, preferably with 16 to 20 carbon atoms.
  • unsaturated natural fatty acids in the form of their alkali and / or alkaline earth salts, for example potassium oleate, have proven particularly useful.
  • the aqueous wetting agent solutions containing alkylglycoside according to the invention preferably contain 0.5 to 3 percent by weight alkylglycosides, 1 to 20 percent by weight inorganic electrolytes and 0 to 2 percent by weight unsaturated natural fatty acid salts, particularly preferably about 1 percent by weight alkylglycosides, 2 to about 10 percent by weight inorganic electrolytes and 0 to 1.5 Weight percent unsaturated natural fatty acid salts.
  • alkyl glycoside-containing aqueous wetting agent solutions according to the invention are expediently used in amounts such that 50 to 500 g, preferably 50 to 200 g, of wetting agent solution are present per 100 g of fat and / or oil.
  • Fats and oils which can be separated into solid and liquid constituents with the alkyl glycoside-containing aqueous wetting agent solutions according to the invention, are fatty acid ester mixtures of vegetable, animal and / or synthetic origin.
  • the fatty acid ester mixtures of vegetable origin include, for example, coconut, palm kernel and shea fat, palm, cottonseed, olive, soybean, peanut, linseed, rapeseed and castor oil.
  • Fatty acid ester mixtures of animal origin are, for example, butter, chicken and goose fat, lard, mutton and beef tallow, kidney and bone fats as well as the large number of different fish oils, tears, whale oils such as menhaden, herring and sperm oil and cod liver oil.
  • Synthetic fatty acid ester mixtures obtained from the above-mentioned vegetable and / or animal fatty acid ester mixtures by transesterification are also suitable.
  • Fatty acid ester mixtures from which saturated triglyceride portions have been separated are also suitable.
  • the separation of fatty acid ester mixtures is carried out according to the known cross-linking process - see, for example, the literature cited at the beginning - by transferring the starting materials to be separated into a dispersion of liquid and solid particles in aqueous alkylglycoside-containing wetting agent solution, separating this dispersion in 2 phases of different specific weights and separating the solid fatty acid ester components from the aqueous alkyl glycoside-containing wetting agent solution.
  • pulpy mixtures of crystalline and liquid components Since the achievable separation effect into solid and liquid components includes Depending on the nature of the solid fraction crystals, it is advisable to melt the starting mixtures completely and then slowly cool them down to the temperature at which the solid portions crystallize and then the wetting agent solution is to be added.
  • the aqueous wetting agent solution wets the solid components, thus separating them from the liquid fatty acid ester components and suspend them in the aqueous phase.
  • the liquid fatty acid ester components are emulsified in the aqueous phase under the action of the alkyl glycoside-containing solution.
  • the separation of the dispersion into a liquid phase with a lower specific weight, which contains the liquid fatty acid ester components, and into a water phase with a higher specific weight, which contains the solid fatty acid ester components is carried out in conventional devices for separating several liquid phases according to their specific weights, for example in separating boxes , Centrifuges, plate separators or hydrocyclones.
  • the solid fatty acid ester constituents suspended in the water phase are advantageously separated from the wetting agent solution by heating the suspension to temperatures above the melting point of the solid fatty acid ester constituents and separating the two resulting liquid phases from one another in a manner known per se, for example by means of separators or centrifuges .
  • the resulting aqueous phase which contains the wetting agent contained in the solid components, is returned to the process. If desired, the solid fatty acid ester components can be washed again with water to completely remove the wetting agent.
  • alkyl glycosides were used in aqueous wetting agent solutions:
  • Alkylglycoside A A C12 / C14 alkyl oligoglucoside (Degree of oligomerization 1.5), whose alkyl radicals are derived from an n-dodecanol / n-tetradecanol mixture in a weight ratio of 70:30.
  • Alkylglycoside B A C12 / C14 alkyl oligoglucoside (Degree of oligomerization 2.2), the alkyl residues of which are derived from an n-dodecanol / n-tetradecanol mixture in a ratio of 70:30.
  • the liquid palm oil fraction had been separated off, the water phase with the solids was heated to about 50 ° C. and the melted fat was separated off by centrifugation.
  • the liquid and solid fatty acid ester components obtained behaved as 81:19 by weight.
  • the liquid palm oil components had an iodine number (according to Kaufmann) of 60.9, the solid palm oil components had an iodine number of 37.1 and a rising melting point of 27.8 ° C. 65% by weight of crystalline components were measured in the solid component by the NMR method (Bruker) at 20 ° C.
  • the liquid and solid components behaved as 84: 16 by weight.
  • the iodine number of the liquid component was 60.1 and that of the solid component 32.8.
  • the rising melting point of the solid palm oil components was 28.4 ° C.
  • 75.4 percent by weight crystalline portions could be determined by the NMR method (20 ° C.).
  • the solid fraction was determined by the NMR method at 20 ° C 29 wt .-% crystalline fractions.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Health & Medical Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Saccharide Compounds (AREA)
  • Fats And Perfumes (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Abstract

Alkylglycosides containing up to 24 carbon atoms in the alkyl chain are used as wetting agents in aqueous wetting agent solutions for the separation of fatty acid ester mixtures such as vegetable, animal and fish oils into solid and liquid components by the hydrophilization process. The alkylglycosides have the advantage of being non-toxic, biodegradable, stable to alkaline hydrolysis and can be prepared from renewable raw materials. The aqueous solution preferably also contains an inorganic electrolyte such as a sulphate.

Description

Die Erfindung betrifft Trennungen von in Fetten und Ölen vor­kommenden Fettsäureestergemischen nach dem an sich bekannten Umnetzverfahren unter Verwendung alkylglycosidhaltiger wässri­ger Netzmittellösungen.The invention relates to separations of fatty acid ester mixtures occurring in fats and oils by the known crosslinking process using aqueous wetting agent solutions containing alkylglycosides.

Natürliche Fette und Öle unterscheiden sich in Kettenlänge und Sättigungsgrad ihrer Fettsäureesterkomponenten und damit auch in ihren physikalischen Eigenschaften. So liegen die Schmelz­punkte gesättigter Fettsäureester oberhalb Raumtemperatur, während ungesättigte Fettsäureester bei Raumtemperatur flüssig sind. Die Trennung von Fetten in feste und flüssige Komponenten stellt eine Auftrennung in stärker gesättigte und stärker ungesättigte Anteile dar.Natural fats and oils differ in chain length and degree of saturation of their fatty acid ester components and thus also in their physical properties. The melting points of saturated fatty acid esters are above room temperature, while unsaturated fatty acid esters are liquid at room temperature. The separation of fats into solid and liquid components represents a separation into more saturated and more unsaturated parts.

Eine Trennung in feste und flüssige Bestandteile kann in vorteil­hafter Weise durch das sogenannte Umnetzverfahren, eine Trennung in Gegenwart wäßriger netzmittelhaltiger Lösungen erreicht werden, wobei die festen Anteile durch Benetzung von der wäßrigen Phase aufgenommen werden.A separation into solid and liquid constituents can be achieved in an advantageous manner by the so-called cross-linking process, a separation in the presence of aqueous solutions containing wetting agents, the solid portions being absorbed by the aqueous phase by wetting.

In den Patentschriften DE-PS 977 544, DE-PS 20 53 257 und US 1 326 049 werden Verfahren zur Trennung von Fettsäure- und Fettsäureestergemischen, insbesondere Triglyceridgemischen, in Bestandteile verschiedener Schmelzpunkte mit Hilfe wässriger Netzmittellösungen beschrieben. Diese Netzmittellösungen enthalten beispielsweise Fettalkoholsulfate oder Alkylbenzolsulfonate. Bei Fettsäuretrennungen haben sich Fettalkoholsulfate mit 10 bis 12 Kohlenstoffatomen in der Kette besonders bewährt.In the patents DE-PS 977 544, DE-PS 20 53 257 and US 1 326 049 processes for the separation of fatty acid and fatty acid ester mixtures, in particular triglyceride mixtures, in components of different melting points with the aid of aqueous Wetting agent solutions described. These wetting agent solutions contain, for example, fatty alcohol sulfates or alkylbenzenesulfonates. When separating fatty acids, fatty alcohol sulfates with 10 to 12 carbon atoms in the chain have proven particularly useful.

Aus der JP 57/197 sind Gemische aus Fettalkoholsulfat und Sorbi­tanfettsäureestern als Netzmittel zur Fettsäure-und Fettrennung in feste und flüssige Bestandteile bekannt. In den Referaten von Chemical Abstracts CA 100, 123 162v und CA 96, 144 899e werden Umnetzungen von Fetten unter Verwendung von Netzmitteln enthaltend Sucrose-Fettsäureester beziehungsweise Gemische aus Sorbitan- oder Polyoxyethylensorbitanfettsäureestern und Fettsäuresalzen beschrieben. Als nachteilig erweist sich jedoch bei Verwendung von Sorbitanfettsäureestern die Tatsache, daß Sorbitanfettsäureester in alkalischen Medien, insbesondere bei höheren Temperaturen, der Hydrolyse unterliegen können.JP 57/197 discloses mixtures of fatty alcohol sulfate and sorbitan fatty acid esters as wetting agents for separating fatty acids and fats into solid and liquid constituents. The abstracts of Chemical Abstracts CA 100 , 123 162v and CA 96 , 144 899e describe the cross-linking of fats using wetting agents containing sucrose fatty acid esters or mixtures of sorbitan or polyoxyethylene sorbitan fatty acid esters and fatty acid salts. However, the fact that sorbitan fatty acid esters can be subject to hydrolysis in alkaline media, in particular at higher temperatures, proves disadvantageous when using sorbitan fatty acid esters.

Die Aufgabe der Erfindung bestand in der Bereitstellung von Netzmittellösungen, die gleich gute Trenneffekte von Fetten und Ölen in feste und flüssige Bestandteile wie Netzmittellösungen des Standes der Technik zeigen, die jedoch hydrolysestabile Substanzen enthalten, die aus nachwachsenden Rohstoffen hergestellt werden.The object of the invention was to provide wetting agent solutions which show equally good separation effects of fats and oils in solid and liquid components as wetting agent solutions of the prior art, but which contain hydrolysis-stable substances which are produced from renewable raw materials.

Überraschenderweise hat sich jetzt gezeigt, daß Alkylglycosid­haltige, wässrige Netzmittellösungen besonders geeignet sind, die erfindungsgemäße Aufgabe zu lösen, obwohl an sich Alkylglyco­side und ihre Netzmitteleigenschaften seit Jahren bekannt sind.Surprisingly, it has now been shown that aqueous glyceride-containing aqueous wetting agent solutions are particularly suitable for achieving the object according to the invention, although alkyl glycosides and their wetting agent properties have been known for years.

Gegenstand der Erfindung ist dementsprechend die Verwendung von Alkylglycosiden mit bis zu 24 C-Atomen in der Alkylkette als Netzmittel in wässrigen Netzmittellösungen zur Trennung von Fettsäureestergemischen in feste und flüssige Bestandteile nach dem an sich bekannten Umnetzverfahren.The invention accordingly relates to the use of alkyl glycosides with up to 24 carbon atoms in the alkyl chain as wetting agents in aqueous wetting agent solutions for separating fatty acid ester mixtures into solid and liquid constituents by the known crosslinking process.

Alkylglycosid-haltige Netzmittellösungen besitzen gegenüber Netzmittellösungen aus dem Stand der Technik den großen Vorteil, daß sie hydrolysestabil sind und daß die in diesen enthaltenen Alkylglycoside eine bekannte, aus nachwachsenden Rohstoffen nach gängigen Methoden der organischen Synthese herstellbare Substanzklasse darstellen. In diesem Zusammenhang wird auf die US-Patentschriften 3 839 318, 3 707 535 und 3 547828, die deutschen Offenlegungsschriften 30 01 064, 20 36 472, 19 43 689 und 19 05 523 sowie auf die europäische Patentanmeldung 77 167 verwiesen. Die erfindungsgemäß eingesetzten Alkylglycoside leiten sich insbesondere von Fett­alkoholen und Zuckern ab. Bevorzugt werden Alkylglycoside mit einem C₆-, C₈-, C₁₀-, C₁₂-, C₁₄-, C₁₆- und/oder C₁₈-Alkylrest, der geradkettig oder verzweigt, gesättigt aber auch einfach oder mehrfach olefinisch ungesättigt sein und beispielsweise bis zu 3 Doppelbindungen aufweisen kann, oder Mischungen derartiger Verbindungen. Besonders geeignet sind Alkylglycoside deren Alkyl- oder Alkenylrest 10 bis 16 C-Atome enthält. Bezüglich des Saccharidrestes der Alkylglycoside gilt, daß sich sowohl Alkyl­monoglycoside, bei denen ein cyclischer Zuckerrest an den Alko­hol gebunden ist, eignen, aber auch Oligomere mit vorzugsweise bis zu 8, insbesondere bis zu 3 glycosidisch gebundenen Zucker­resten, beispielsweise Glucose- oder Maltoseresten. Dabei ist die Anzahl der Zuckerreste ein statistischer Mittelwert, dem die bei diesen Verbindungen übliche Verteilung zugrunde liegt. Alkylgly­coside auf der Basis von C₁₂- bis C₁₄-Fettalkoholen und mit bis zu 2,5 Glycosidresten können besonders geeignet sein.Wetting agent solutions containing alkylglycoside have the great advantage over wetting agent solutions from the prior art in that they are hydrolysis-stable and that the alkylglycosides contained in them represent a known class of substance which can be prepared from renewable raw materials by conventional methods of organic synthesis. In this connection, reference is made to US Pat. Nos. 3,839,318, 3,707,535 and 3,547,828, German Offenlegungsschriften 30 01 064, 20 36 472, 19 43 689 and 19 05 523 and European patent application 77 167. The alkyl glycosides used according to the invention are derived in particular from fatty alcohols and sugars. Alkyl glycosides with a C₆-, C₈-, C₁₀-, C₁₂-, C₁₆-, C₁₆- and / or C₁₈-alkyl radical are preferred which are straight-chain or branched, saturated but also mono- or poly-olefinically unsaturated and have, for example, up to 3 double bonds can, or mixtures of such compounds. Alkyl glycosides whose alkyl or alkenyl radical contains 10 to 16 carbon atoms are particularly suitable. With regard to the saccharide residue of the alkyl glycosides, both alkyl monoglycosides in which a cyclic sugar residue is bonded to the alcohol are suitable, but also oligomers with preferably up to 8, in particular up to 3, glycosidically bonded sugar residues, for example glucose or maltose residues. The number of sugar residues is a statistical mean, which is based on the distribution customary for these compounds. Alkyl glycosides based on C₁₂ to C₁₄ fatty alcohols and with up to 2.5 glycoside residues can be particularly suitable.

Die Wirkung der alkylglycosidhaltigen wässrigen Netzmittel­lösungen wird verbessert, wenn sie nicht-oberflächenaktive, gegenüber den Ausgangsstoffen inerte Elektrolyte enthalten. Hierzu gehören beispielsweise die wasserlöslichen Chloride, Sulfate und Nitrate von 1- bis 3-wehrwertigen Metallen, vorzugsweise der Alkali-, Erdalkali- und Erdmetalle. Insbesondere haben sich Zu­ sätze von Natriumsulfat und/oder Magnesiumsulfat bewährt. Im Zusammenhang mit der vorliegenden Erfindung sind unter alkylglycosidhaltigen, wässrigen Netzmittellösungen bevorzugt elektrolythaltige alkylglycosidhaltige wässrige Netzmittellösungen zu verstehen.The action of the aqueous wetting agent solutions containing alkylglycoside is improved if they contain non-surface-active electrolytes which are inert towards the starting materials. These include, for example, the water-soluble chlorides, sulfates and nitrates of 1- to 3-membered metals, preferably the alkali, alkaline earth and earth metals. In particular, have Proven sets of sodium sulfate and / or magnesium sulfate. In connection with the present invention, alkyl glycoside-containing aqueous wetting agent solutions are preferably to be understood as meaning electrolyte-containing alkyl glycoside-containing aqueous wetting agent solutions.

Darüber hinaus kann die Wirkung der alkylglycosidhaltigen wässrigen Netzmittellösungen durch einen Zusatz an ungesättigten natürlichen Fettsäuresalzen mit mehr als 14 C-Atomen, vorzugs­weise mit 16 bis 20 C-Atomen verbessert werden. Insbesondere haben sich ungesättigte natürliche Fettsäuren in Form ihrer Alkali- und/oder Erdalkalisalze, beispielsweise Kaliumoleat, bewährt.In addition, the effect of the aqueous glyceride-containing wetting agent solutions can be improved by adding unsaturated natural fatty acid salts with more than 14 carbon atoms, preferably with 16 to 20 carbon atoms. Unsaturated natural fatty acids in the form of their alkali and / or alkaline earth salts, for example potassium oleate, have proven particularly useful.

Die erfindungsgemäßen alkylglycosidhaltigen wässrigen Netzmittel­lösungen enthalten bevorzugt 0,5 bis 3 Gewichtsprozent Alkylglycoside, 1 bis 20 Gewichtsprozent anorganische Elektrolyte und 0 bis 2 Gewichtsprozent ungesättigte natürliche Fettsäuresalze, besonders bevorzugt etwa 1 Gewichtsprozent Alkylglycoside, 2 bis etwa 10 Gewichtsprozent anorganische Elektrolyte und 0 bis 1,5 Gewichtsprozent ungesättigte natürliche Fettsäuresalze.The aqueous wetting agent solutions containing alkylglycoside according to the invention preferably contain 0.5 to 3 percent by weight alkylglycosides, 1 to 20 percent by weight inorganic electrolytes and 0 to 2 percent by weight unsaturated natural fatty acid salts, particularly preferably about 1 percent by weight alkylglycosides, 2 to about 10 percent by weight inorganic electrolytes and 0 to 1.5 Weight percent unsaturated natural fatty acid salts.

Zweckmäßigerweise werden die erfindungsgemäßen alkylglycosid­haltigen wässrigen Netzmittellösungen in solchen Mengen einge­setzt, daß pro 100 g Fett und/oder Öl, 50 bis 500 g, vorzugs­weise 50 bis 200 g Netzmittellösung vorhanden sind.The alkyl glycoside-containing aqueous wetting agent solutions according to the invention are expediently used in amounts such that 50 to 500 g, preferably 50 to 200 g, of wetting agent solution are present per 100 g of fat and / or oil.

Fette und Öle, die mit den erfindungsgemäßen alkylglycosidhal­tigen wässrigen Netzmittellösungen in feste und flüssige Bestand­teile getrennt werden können, sind Fettsäureestergemische pflanz­lichen, tierischen und/oder synthetischen Ursprungs.Fats and oils, which can be separated into solid and liquid constituents with the alkyl glycoside-containing aqueous wetting agent solutions according to the invention, are fatty acid ester mixtures of vegetable, animal and / or synthetic origin.

Zu den Fettsäureestergemischen pflanzlichen Ursprungs gehören beispielsweise Kokos-, Palmkern- und Sheafett, Palm-, Baumwollsaat-, Oliven-, Soja-, Erdnuß-, Lein-, Raps- und Rizinusöl. Fettsäureestergemische tierischen Ursprungs sind beispielsweise Butter, Hühner- und Gänsefett, Schweineschmalz, Hammel- und Rindertalg, Nieren- und Knochenfette sowie die große Zahl der verschiedenen Fischöle, Trane, Walöle wie beispielsweise Menhaden-, Herings- und Spermöl und Lebertrane. Weiterhin eignen sich auch synthetische Fettsäureestergemische, die aus den obengenannten pflanzlichen und/oder tierischen Fettsäureestergemischen durch Umesterung erhalten werden. Fettsäureestergemische, von denen gesättigte Triglyceridanteile abgetrennt worden sind, sind ebenfalls geeignet.The fatty acid ester mixtures of vegetable origin include, for example, coconut, palm kernel and shea fat, palm, cottonseed, olive, soybean, peanut, linseed, rapeseed and castor oil. Fatty acid ester mixtures of animal origin are, for example, butter, chicken and goose fat, lard, mutton and beef tallow, kidney and bone fats as well as the large number of different fish oils, tears, whale oils such as menhaden, herring and sperm oil and cod liver oil. Synthetic fatty acid ester mixtures obtained from the above-mentioned vegetable and / or animal fatty acid ester mixtures by transesterification are also suitable. Fatty acid ester mixtures from which saturated triglyceride portions have been separated are also suitable.

Die Trennung von Fettsäureestergemischen erfolgt nach dem an sich bekannten Umnetzverfahren - siehe hierzu beispielsweise die eingangs zitierte Literatur - durch Überführen der zu trennenden Ausgangsstoffe in eine Dispersion flüssiger und fester Partikel in wässriger alkylglycosidhaltiger Netzmittellösung, Trennen dieser Dispersion in 2 Phasen verschiedener spezifischer Gewichte und Trennen der festen Fettsäureesterbestandteile aus der wässrigen alkylglycosidhaltigen Netzmittellösung. Zur Herstellung von Dispersionen flüssiger und fester Komponenten in wässrigen alkylglycosidhaltigen Netzmittellösungen setzt man zweckmäßigerweise breiige Gemische aus kristallinen und flüssigen Anteilen ein. Da der erzielbare Trenneffekt in feste und flüssige Bestandteile u.a. von der Beschaffenheit der Festanteilkristalle abhängt, empfiehlt es sich, die Ausgangsgemische vollständig aufzuschmelzen und anschließend langsam auf die Temperatur abzukühlen, bei der die Festanteile auskristallisieren und anschließend die Netzmittellösung zugegeben werden soll.The separation of fatty acid ester mixtures is carried out according to the known cross-linking process - see, for example, the literature cited at the beginning - by transferring the starting materials to be separated into a dispersion of liquid and solid particles in aqueous alkylglycoside-containing wetting agent solution, separating this dispersion in 2 phases of different specific weights and separating the solid fatty acid ester components from the aqueous alkyl glycoside-containing wetting agent solution. For the preparation of dispersions of liquid and solid components in aqueous alkylglycoside-containing wetting agent solutions, it is expedient to use pulpy mixtures of crystalline and liquid components. Since the achievable separation effect into solid and liquid components includes Depending on the nature of the solid fraction crystals, it is advisable to melt the starting mixtures completely and then slowly cool them down to the temperature at which the solid portions crystallize and then the wetting agent solution is to be added.

Die wässrige Netzmittellösung benetzt die festen Komponenten, trennt sie damit von den flüssigen Fettsäureesteranteilen und suspendiert sie in der wässrigen Phase. Die flüssigen Fettsäureesterbestandteile werden unter der Wirkung der alkylglycosidhaltigen Lösung in der wässrigen Phase emulgiert. Die Trennung der Dispersion in eine Flüssigphase mit geringerem spezifischen Gewicht, die die flüssigen Fettsäureesterbestandteile enthält, und in eine Wasserphase mit höherem spezifischem Ge­wicht, die die festen Fettsäureesterkomponenten enthält, erfolgt in üblichen Einrichtungen zur Trennung mehrerer flüssiger Pha­sen nach ihren spezifischen Gewichten, beispielsweise in Scheide­kästen, Zentrifugen, Tellerseperatoren oder Hydrocyclonen.The aqueous wetting agent solution wets the solid components, thus separating them from the liquid fatty acid ester components and suspend them in the aqueous phase. The liquid fatty acid ester components are emulsified in the aqueous phase under the action of the alkyl glycoside-containing solution. The separation of the dispersion into a liquid phase with a lower specific weight, which contains the liquid fatty acid ester components, and into a water phase with a higher specific weight, which contains the solid fatty acid ester components, is carried out in conventional devices for separating several liquid phases according to their specific weights, for example in separating boxes , Centrifuges, plate separators or hydrocyclones.

Die in der Wasserphase suspendierten festen Fettsäureesterbe­standteile werden in vorteilhafter Weise von der Netzmittellösung abgetrennt, indem die Suspension auf Temperaturen oberhalb des Schmelzpunktes der festen Fettsäureesterbestandteile erhitzt wird und die beiden entstehenden flüssigen Phasen in an sich bekann­ter Weise, beispielsweise durch Abscheider oder Zentrifugen, voneinander getrennt werden. Die anfallende wäßrige Phase, die das in den Festanteilen enthaltene Netzmittel enthält, wird in das Verfahren zurückgeführt. Gewünschtenfalls können die festen Fettsäureesterbestandteile noch einmal mit Wasser zur vollständigen Entfernung des Netzmittels gewaschen werden.The solid fatty acid ester constituents suspended in the water phase are advantageously separated from the wetting agent solution by heating the suspension to temperatures above the melting point of the solid fatty acid ester constituents and separating the two resulting liquid phases from one another in a manner known per se, for example by means of separators or centrifuges . The resulting aqueous phase, which contains the wetting agent contained in the solid components, is returned to the process. If desired, the solid fatty acid ester components can be washed again with water to completely remove the wetting agent.

BeispieleExamples

Folgende Alkylglycoside wurden in wässrigen Netzmittellösungen eingesetzt:The following alkyl glycosides were used in aqueous wetting agent solutions:

Alkylglycosid A: Ein C₁₂/C₁₄-Alkyloligoglucosid
(Oligomerisierungsgrad 1,5), desssen Alkylreste sich von einem n-Dodecanol/n-Tetradecanolge­misch im Gewichtsverhältnis 70 : 30 ableiten.Alkylglycoside A: A C₁₂ / C₁₄ alkyl oligoglucoside
(Degree of oligomerization 1.5), whose alkyl radicals are derived from an n-dodecanol / n-tetradecanol mixture in a weight ratio of 70:30.

Alkylglycosid B: Ein C₁₂/C₁₄-Alkyloligoglucosid
(Oligomerisierungsgrad 2,2), dessen Alkylreste sich von einem n-Dodecanol/n-Tetradecanolge­misch im Verhältnis 70 : 30 ableiten.Alkylglycoside B: A C₁₂ / C₁₄ alkyl oligoglucoside
(Degree of oligomerization 2.2), the alkyl residues of which are derived from an n-dodecanol / n-tetradecanol mixture in a ratio of 70:30.

Beispiel 1example 1 Trennung von Palmöl (Verseifungszahl VZ = 198,4; Säurezahl SZ = 6,0; Jodzahl JZ = 55,8).Separation of palm oil (saponification number VZ = 198.4; acid number SZ = 6.0; iodine number JZ = 55.8).

150 g Palmöl wurden bei etwa 40 °C aufgeschmolzen und unter Rühren bei 20 °C über 3 Tage zur Kristallisation gebracht. Zu dem erhaltenen breiigen Gemisch aus flüssigen und festen Be­standteilen wurde eine Netzmittellösung hinzugefügt, die sich aus 205 g Wasser, 90 g Magnesiumsulfatheptahydrat und 4,9 g 62 %igem Alkylglycosid A (entsprechend 1 Gewichtsprozent Aktiv substanz in der Netzmittellösung) zusammensetzte. Die Mischung wurde 20 Minuten bei etwa 20 °C gerührt und anschließend in einer Becherzentrifuge (Varifuge st, Firma Heraeus/Christ) bei 4000 Umdrehungen pro Minute in 5 Minuten getrennt. Es erfolgte Auftrennung in eine netzmittelfreie Flüssigphase und in eine schwerere Wasserphase, in der sich die dispergierten Festanteile befanden.150 g of palm oil were melted at about 40 ° C and brought to crystallization with stirring at 20 ° C for 3 days. A wetting agent solution was added to the resulting pulpy mixture of liquid and solid components, which was composed of 205 g of water, 90 g of magnesium sulfate heptahydrate and 4.9 g of 62% alkylglycoside A (corresponding to 1% by weight of active substance in the wetting agent solution). The mixture was stirred at about 20 ° C. for 20 minutes and then separated in a cup centrifuge (Varifuge st, Heraeus / Christ company) at 4000 revolutions per minute in 5 minutes. It was separated into a wetting agent-free liquid phase and a heavier water phase in which the dispersed solids were.

Nach Abtrennung der flüssigen Palmölfraktion wurde die Wasser­phase mit den Festanteilen auf etwa 50 °C erhitzt und das geschmolzene Fett durch Zentrifugieren abgetrennt. Die erhaltenen flüssigen und festen Fettsäureesterbestandteile verhielten sich gewichtsmäßig wie 81:19. Die flüssigen Palmölbestandteile besaßen eine Jodzahl (nach Kaufmann) von 60,9, die festen Palmölbestandteile eine Jodzahl von 37,1 und einen Steigschmelzpunkt von 27,8 °C. Im Festanteil wurden nach der NMR-Methode (Bruker) bei 20 °C 65 Gewichtsprozent kristalline Anteile vermessen.After the liquid palm oil fraction had been separated off, the water phase with the solids was heated to about 50 ° C. and the melted fat was separated off by centrifugation. The liquid and solid fatty acid ester components obtained behaved as 81:19 by weight. The liquid palm oil components had an iodine number (according to Kaufmann) of 60.9, the solid palm oil components had an iodine number of 37.1 and a rising melting point of 27.8 ° C. 65% by weight of crystalline components were measured in the solid component by the NMR method (Bruker) at 20 ° C.

Wurde das Alkylglycosid A durch eine gleichgroße Menge an Alkylglucosid B ersetzt und unter sonst gleichen Bedingungen Palmöl in flüssige und feste Bestandteile getrennt, verhielten sich die Flüssig- und Festanteile gewichtsmäßig wie 84 : 16. Die Jodzahl des Flüssiganteils betrug 60,1, die des Festanteils 32,8. Der Steigschmelzpunkt der festen Palmölkomponenten lag bei 28,4 °C. Im Festanteil konnten 75,4 Gewichtsprozent kristalline Anteile nach der NMR-Methode (20 °C) ermittelt werden.If the alkyl glycoside A was replaced by an equal amount of alkyl glucoside B and palm oil was separated into liquid and solid components under otherwise identical conditions, the liquid and solid components behaved as 84: 16 by weight. The iodine number of the liquid component was 60.1 and that of the solid component 32.8. The rising melting point of the solid palm oil components was 28.4 ° C. In the solid fraction, 75.4 percent by weight crystalline portions could be determined by the NMR method (20 ° C.).

Beispiel 2Example 2 Trennung von Kokosöl (VZ = 254,1; SZ = 12,4; JZ = 8,7)Separation of coconut oil (VZ = 254.1; SZ = 12.4; JZ = 8.7)

Die Trennung von Kokosöl in feste und flüssige Bestandteile wurde unter den in Beispiel 1 angegebenen Bedingungen durchgeführt. Die Ergebnisse sind in untenstehender Tabelle zusammengefaßt.

Figure imgb0001
The separation of coconut oil into solid and liquid components was carried out under the conditions given in Example 1. The results are summarized in the table below.
Figure imgb0001

1) Zusammensetzung der Netzmittellösungen s. Beispiel 1 1) Composition of wetting agent solutions see example 1

Beispiel 3Example 3 Trennung von Palmöl (Verseifungszahl VZ = 199,6; Säurezahl SZ = 0,8; Jodzahl JZ = 52,6).Separation of palm oil (saponification number VZ = 199.6; acid number SZ = 0.8; iodine number JZ = 52.6).

150 g Palmöl wurden bei etwa 40 °C aufgeschmolzen und nach Zusatz von 1,5 g Kaliumoleat unter Rühren bei 20 °C über 3 Tage zur Kristallisation gebracht. Anschließend wurde eine Lösung von 90 g Magnesiumsulfatheptahydrat und 5 g 60%igem Alkylglycosid B (entsprechend 3 g Aktivsubstanz) in 205 g Wasser zugesetzt. Die Mischung wurde 20 Minuten bei 20 °C gerührt. Die Trennung erfolgte unter den in Beispiel 1 angegebenen Bedingungen. Die erhaltenen festen und flüssigen Fettsäureesterbestandteile verhielten sich gewichtsmäßig wie 19,5 : 80,5.
Jodzahl des Flüssiganteils: 57,6
Jodzahl des Festanteils: 38,3
Steigschmelzpunkt des Festanteils: 27,7 °C150 g of palm oil were melted at about 40 ° C. and, after addition of 1.5 g of potassium oleate, they were brought to crystallization with stirring at 20 ° C. over 3 days. A solution of 90 g of magnesium sulfate heptahydrate and 5 g of 60% alkylglycoside B (corresponding to 3 g of active substance) in 205 g of water was then added. The mixture was stirred at 20 ° C for 20 minutes. The separation was carried out under the conditions given in Example 1. The weight of the solid and liquid fatty acid ester components obtained was 19.5: 80.5.
Iodine number of the liquid portion: 57.6
Iodine number of the solid component: 38.3
Rise melting point of the solid portion: 27.7 ° C

Im Festanteil wurden NMR-spektroskopisch bei 20 °C 59,1 Gew.-% kristalline Anteile ermittelt.In the solid fraction, 59.1% by weight of crystalline components were determined by NMR spectroscopy at 20 ° C.

Beispiel 4Example 4 Trennung von Schweineschmalz (Verseifungszahl VZ = 194,5; Säurezahl SZ = 3,9; Jodzahl JZ = 63,2).Separation of lard (saponification number VZ = 194.5; acid number SZ = 3.9; iodine number JZ = 63.2).

200 g Schweineschmalz wurden bei etwa 40 °C aufgeschmolzen und unter Rühren wie folgt abgekühlt: 1 Stunde bei 26 °C, 1 Stunde bei 24 °C, 1 Stunde bei 22 °C, 1 Stunden bei 21 °C und 3 Stunden bei 20 °C. Anschließend wurde eine Netzmittellösung zugefügt, die sich aus 286 g Wasser, 6 g Natriumsulfat, 3 g Na­triumoleat und 5 g 60-Gew.-%igem Alkylglycosid B (entsprechend 1 Gew.-% Aktivsubstanz in der Netzmittellösung) zusammensetzte. Die weitere Verfahrensweise entsprach der in Beispiel 1 beschrie­benen. Die erhaltenen flüssigen und festen Fettsäureesterbestand­teile verhielten sich gewichtsmäßig wie 80,5 : 19,5.
Jodzahl des Flüssiganteils: 70,6
Trübungspunkt des Flüssiganteils: 6 °C
Jodzahl des Festanteils: 58,3
Steigschmelzpunkt des Festanteils: 35,9 °C200 g of lard were melted at about 40 ° C and cooled with stirring as follows: 1 hour at 26 ° C, 1 hour at 24 ° C, 1 hour at 22 ° C, 1 hour at 21 ° C and 3 hours at 20 ° C. A wetting agent solution was then added, which was composed of 286 g of water, 6 g of sodium sulfate, 3 g of sodium oleate and 5 g of 60% by weight alkylglycoside B (corresponding to 1% by weight of active substance in the wetting agent solution). The further procedure corresponded to that described in Example 1. The liquid and solid fatty acid ester components obtained behaved as 80.5: 19.5 by weight.
Iodine number of the liquid portion: 70.6
Cloud point of the liquid portion: 6 ° C
Iodine number of the solid component: 58.3
Rise melting point of the solid portion: 35.9 ° C

Im Festanteil wurden nach der NMR-Methode bei 20 °C 29 Gew.-% kristalline Anteile ermittelt.The solid fraction was determined by the NMR method at 20 ° C 29 wt .-% crystalline fractions.

Wurde die Trennung von Schweineschmalz unter Verwendung von 300 g einer wäßrigen Netzmittellösung mit 1 Gew.-% Aktivsubstanz des Alkylglycosids B und 5 Gew.-% Magnesiumsulfatheptahydrat nach obiger Vorgehensweise durchgeführt, so wurden Flüssig- ­und Festanteil im Gewichtsverhältnis 65 : 35 erhalten.
Jodzahl des Flüssiganteils: 70,5
Trübungspunkt des Flüssiganteils: 6 °C
Jodzahl des Festanteils: 51,1
Steigschmelzpunkt des Festanteils: 38 °CIf the separation of lard was carried out using 300 g of an aqueous wetting agent solution with 1% by weight of active substance of alkyl glycoside B and 5% by weight of magnesium sulfate heptahydrate according to the above procedure, liquid and solid contents in a weight ratio of 65:35 were obtained.
Iodine number of the liquid portion: 70.5
Cloud point of the liquid portion: 6 ° C
Iodine number of the solid component: 51.1
Rising melting point of the solid component: 38 ° C

Im Festanteil wurden nach der NMR-Methode bei 20 °C 43 Gew.-% kristalline Anteile ermittelt.In the solid fraction, 43% by weight crystalline portions were determined by the NMR method at 20 ° C.

Claims (6)

1. Verwendung von Alkylglycosiden mit bis zu 24 C-Atomen in der Alkylkette als Netzmittel in wässrigen Netzmittellösungen zur Trennung von Fettsäureestergemischen in feste und flüs­sige Bestandteile nach dem an sich bekannten Umnetzverfah­ren.1. Use of alkyl glycosides with up to 24 carbon atoms in the alkyl chain as wetting agents in aqueous wetting agent solutions for separating fatty acid ester mixtures into solid and liquid constituents by the known crosslinking process. 2. Ausführungsform nach Anspruch 1, dadurch gekennzeichnet, daß Alkylglycoside mit 6 bis 18, vorzugsweise 10 bis 16 C-Atomen im Alkylrest verwendet werden.2. Embodiment according to claim 1, characterized in that alkyl glycosides having 6 to 18, preferably 10 to 16 carbon atoms in the alkyl radical are used. 3. Ausführungsform nach den Ansprüchen 1 und 2, dadurch gekennzeichnet, daß Alkylmono- und/oder Alkylpolyglycoside mit bis zu 8, vorzugsweise mit bis zu 3 Glycosideinheiten verwendet werden.3. Embodiment according to claims 1 and 2, characterized in that alkyl mono- and / or alkyl polyglycosides with up to 8, preferably with up to 3, glycoside units are used. 4. Ausführungsform nach den Ansprüchen 1 bis 3, dadurch gekennzeichnet, daß die Alkylglycoside zusammen mit anorganischen Elektrolyten, gewünschtenfalls in Abmischung mit ungesättigten natürlichen Fettsäuresalzen mit mehr als 14 C-Atomen, vorzugsweise 16 bis 20 C-Atomen, in den wässrigen Netzmittellösungen verwendet werden.4. Embodiment according to claims 1 to 3, characterized in that the alkyl glycosides are used together with inorganic electrolytes, if desired in a mixture with unsaturated natural fatty acid salts with more than 14 C atoms, preferably 16 to 20 C atoms, in the aqueous wetting agent solutions . 5. Ausführungsform nach den Ansprüchen 1 bis 4, dadurch gekennzeichnet, daß wässrige alkylglycosidhaltige Netzmittellösungen mit 0,5 bis 3 Gewichtsprozent, vorzugsweise etwa 1 Gewichtsprozent Alkylglycosiden, 1 bis 20 Gewichtsprozent, vorzugsweise 2 bis etwa 10 Gewichtsprozent anorganischen Elektrolyten und 0 bis 2 Gewichtsprozent, vorzugsweise 0 bis 1,5 Gewichtsprozent ungesättigten natürlichen Fettsäuresalzen mit mehr als 14 C-Atomen, vorzugsweise 16 bis 20 C-Atomen, verwendet werden.5. Embodiment according to claims 1 to 4, characterized in that aqueous alkylglycoside-containing wetting agent solutions with 0.5 to 3 percent by weight, preferably about 1 percent by weight alkylglycosides, 1 to 20 percent by weight, preferably 2 to about 10 percent by weight of inorganic electrolytes and 0 to 2 percent by weight, preferably 0 to 1.5 percent by weight of unsaturated natural fatty acid salts with more than 14 C atoms, preferably 16 to 20 C atoms, can be used. 6. Ausführungsform nach den Ansprüchen 1 bis 5, dadurch gekennzeichnet, daß pro 100 g Fettsäureestergemisch 50 bis 500 g, vorzugsweise 50 bis 200 g, wässrige alkylglycosidhaltige Netzmittellösung eingesetzt werden.6. Embodiment according to claims 1 to 5, characterized in that 50 to 500 g, preferably 50 to 200 g, of aqueous alkyl glycoside-containing wetting agent solution are used per 100 g of fatty acid ester mixture.
EP86116026A 1985-11-29 1986-11-19 Use of alkyl glycosides in the separation of fatty acid ester mixtures Expired EP0224798B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3542226 1985-11-29
DE3542226 1985-11-29

Publications (2)

Publication Number Publication Date
EP0224798A1 true EP0224798A1 (en) 1987-06-10
EP0224798B1 EP0224798B1 (en) 1989-05-24

Family

ID=6287174

Family Applications (1)

Application Number Title Priority Date Filing Date
EP86116026A Expired EP0224798B1 (en) 1985-11-29 1986-11-19 Use of alkyl glycosides in the separation of fatty acid ester mixtures

Country Status (7)

Country Link
EP (1) EP0224798B1 (en)
JP (1) JPS62132531A (en)
DE (1) DE3663532D1 (en)
DK (1) DK551386A (en)
ES (1) ES2003554A6 (en)
GB (1) GB2183669B (en)
MY (1) MY100868A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0278712A2 (en) * 1987-02-06 1988-08-17 Kao Corporation Method of separating oleaginous matter into components having various melting points

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2989682B2 (en) * 1991-04-04 1999-12-13 花王株式会社 Method for producing liquid fatty acid and solid fatty acid
KR102228443B1 (en) * 2013-09-30 2021-03-16 엔자 바이오테크 에이비 Surfactant composition

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB472086A (en) * 1936-08-18 1937-09-16 Schou Herbert Improvements in or relating to the preparation of emulsions
DE1267367B (en) * 1963-05-21 1968-05-02 Henkel & Cie GmbH 4000 Dusseldorf Processes for the separation of mixtures of liquid and solid fatty substances, in particular of liquid and solid fatty acids

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB472086A (en) * 1936-08-18 1937-09-16 Schou Herbert Improvements in or relating to the preparation of emulsions
DE1267367B (en) * 1963-05-21 1968-05-02 Henkel & Cie GmbH 4000 Dusseldorf Processes for the separation of mixtures of liquid and solid fatty substances, in particular of liquid and solid fatty acids

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Band 100, Nr. 20, Mai 1984, Seite 109, Zusammenfassung Nr. 123162v, Columbus, Ohio, US; & JP-A-58 198 423 (NIPPON OILS AND FATS CO., LTD) 18-11-1983 *
CHEMICAL ABSTRACTS, Band 100, Nr. 20, Mai 1984, Seite 114, Zusammenfassung Nr. 158592n, Columbus, Ohio, US; & JP-A-58 222 195 (PROCTER AND GAMBLE CO.) 23-12-1983 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0278712A2 (en) * 1987-02-06 1988-08-17 Kao Corporation Method of separating oleaginous matter into components having various melting points
EP0278712A3 (en) * 1987-02-06 1989-09-13 Kao Corporation Method of separating oleaginous matter into components having various melting points

Also Published As

Publication number Publication date
MY100868A (en) 1991-05-16
DE3663532D1 (en) 1989-06-29
DK551386D0 (en) 1986-11-18
GB8626285D0 (en) 1986-12-03
EP0224798B1 (en) 1989-05-24
GB2183669A (en) 1987-06-10
GB2183669B (en) 1989-10-04
DK551386A (en) 1987-05-30
JPS62132531A (en) 1987-06-15
ES2003554A6 (en) 1988-11-01

Similar Documents

Publication Publication Date Title
EP0555776A1 (en) Process for separating and purifying fatty acids and alpha-hydroxy fatty acids
DE3317909A1 (en) PEARL SHINE DISPERSION
DE3734217C1 (en) Use of organosilicon compounds to thicken OElen
EP0224798B1 (en) Use of alkyl glycosides in the separation of fatty acid ester mixtures
CH426452A (en) Process for the production of fats, especially edible fats with a melting behavior that differs from the starting material
WO2015185675A1 (en) Apparatus and method for obtaining glycoglycerolipids and glycosphingolipids from lipid phases
DE1542067A1 (en) Process for granulating powdery substances such as metal salts and the like.
EP0268974A2 (en) Method for the preparation of mixtures of mono- and oligomers of carbohydrate esters, mixtures of carbohydrate esters so obtained and their use
DE1617023C3 (en) Process for separating fat crystals from fatty or fatty acid mixtures
DE2309165C2 (en) Process for the separation of a mixture of liquid and crystalline fatty acid triglycerides into two fractions
DD297396A5 (en) METHOD FOR THE TREATMENT OF FATS
DE2053257C3 (en) Process for the separation of fatty acid ester mixtures into components with different melting points
DE19906551C1 (en) Purification of phytosterols useful as hypocholesterolemic agents and as food additives comprises crystallization from a saturated hydrocarbon solvent
DE60305791T2 (en) Process for the preparation of a fatty acid
DE2100022C3 (en) Process for separating mixtures of fatty substances into components with different melting points
DE2420623C2 (en) Process for the separation of mixtures of fatty substances
DE977544C (en) Process for the separation of mixtures of carboxylic acid esters into components of different melting points
DE925674C (en) Process for the separation of fatty acid mixtures into components with different melting points
CH646069A5 (en) METHOD FOR INSULATING A MATERIAL FROM A SOLUTION.
EP0014439A2 (en) Process for the separation of fatty mixtures into components of different melting points
DE1078562B (en) Process for the production of solid fats from palm oil suitable for the preparation of margarine
DE1107659B (en) Process for the separation of mixtures of higher molecular weight fatty alcohols
DEH0014530MA (en)
DE2602998B2 (en) Process for separating an oil or fat into a liquid and a solid fraction
DE1010062B (en) Process for the separation of mixtures of higher molecular weight alcohols into components with different melting points

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH DE FR IT LI NL SE

17P Request for examination filed

Effective date: 19871106

17Q First examination report despatched

Effective date: 19880713

RBV Designated contracting states (corrected)

Designated state(s): BE DE FR IT NL

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): BE DE FR IT NL

REF Corresponds to:

Ref document number: 3663532

Country of ref document: DE

Date of ref document: 19890629

ET Fr: translation filed
ITF It: translation for a ep patent filed

Owner name: STUDIO JAUMANN

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
ITTA It: last paid annual fee
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 19921130

Year of fee payment: 7

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 19921223

Year of fee payment: 7

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19931026

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19931110

Year of fee payment: 8

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Effective date: 19931130

BERE Be: lapsed

Owner name: HENKEL K.G.A.A.

Effective date: 19931130

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19940601

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Effective date: 19950731

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19950801

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES;WARNING: LAPSES OF ITALIAN PATENTS WITH EFFECTIVE DATE BEFORE 2007 MAY HAVE OCCURRED AT ANY TIME BEFORE 2007. THE CORRECT EFFECTIVE DATE MAY BE DIFFERENT FROM THE ONE RECORDED.

Effective date: 20051119