WO1992022627A1 - Fatty acid glycerin esters having improved rheological properties - Google Patents

Fatty acid glycerin esters having improved rheological properties Download PDF

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Publication number
WO1992022627A1
WO1992022627A1 PCT/EP1992/001227 EP9201227W WO9222627A1 WO 1992022627 A1 WO1992022627 A1 WO 1992022627A1 EP 9201227 W EP9201227 W EP 9201227W WO 9222627 A1 WO9222627 A1 WO 9222627A1
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Prior art keywords
triglycerides
carbon atoms
fatty acid
fatty acids
branched
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PCT/EP1992/001227
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German (de)
French (fr)
Inventor
Akira Nakashima
Nagao Totani
Yoshio Kawahara
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Henkel Kommanditgesellschaft Auf Aktien
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Publication of WO1992022627A1 publication Critical patent/WO1992022627A1/en

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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M101/00—Lubricating compositions characterised by the base-material being a mineral or fatty oil
    • C10M101/04—Fatty oil fractions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/38—Esters of polyhydroxy compounds
    • 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
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C11C3/06—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with glycerol
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C11C3/08—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with fatty acids
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C11C3/10—Ester interchange
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species

Definitions

  • the invention relates to fatty acid glycerol esters with improved rheological properties, a process for their preparation in which triglycerides of linear fatty acids, branched fatty acids and glycerol are subjected to simultaneous esterification and transesterification in a manner known per se, and the use of these products for the production of lubricants.
  • Animal fats and oils such as beef tallow or lard, are known as base oils for the production of rolling oils, metal treatment agents, finishing agents, or PVC additives.
  • base oils for the production of rolling oils, metal treatment agents, finishing agents, or PVC additives.
  • they have the serious technical disadvantage that they have inadequate flow properties at low temperatures and can therefore only be used to a limited extent, for example in winter or in cold regions.
  • the object of the invention was to provide fatty acid glycerol esters which are free from the disadvantages described.
  • the invention relates to fatty acid glycerol esters with improved rheological properties, obtainable by containing a mixture a) triglycerides of the formula (I),
  • R 1 CO, R 2 CO and R 3 CO independently of one another represent linear acyl radicals having 6 to 24 carbon atoms and 0 or 1 to 5 double bonds, b) branched fatty acids of the formula (II),
  • the fatty acid glycerol esters produced in this way are low-viscosity, have excellent lubricating properties and low pour points, and are therefore advantageously different from natural triglycerides of the same chain length.
  • Another object of the invention relates to a process for the preparation of fatty acid glycerol esters with improved rheological properties, in which one contains a mixture a) triglycerides of the formula (I),
  • R 1 CO, R 2 CO and R 3 CO independently of one another represent linear acyl radicals having 6 to 24 carbon atoms and 0 or 1 to 5 double bonds, b) branched fatty acids of the formula (II),
  • Triglycerides that can be used as component a) can be synthetic in nature. However, natural fats and / or oils are preferably used, which are predominantly, ie. H. more than 95% of linear fatty acids with 6 to 24 carbon atoms and 0 or 1 to 5
  • Typical examples of fatty acids from which the triglycerides mentioned can be constructed are caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid,
  • Linolenic acid arachidic acid, gadoleic acid, arachidonic acid, behenic acid,
  • hydroxy-substituted fatty acids such as ricinoleic acid or 12-hydroxystearic acid can also be used.
  • triglycerides which are wholly or predominantly derived from fatty acids having 12 to 18 carbon atoms and 0 or 1
  • triglycerides which are suitable as starting materials in the context of the invention are olive oil, peanut oil, cottonseed oil, sunflower oil, rapeseed oil, meadowfoam oil, castor oil, linseed oil, soybean oil, babassu oil, fish oil and in particular palm oil, palm kernel oil, coconut oil, beef tallow and lard.
  • Those triglycerides which have an iodine number of less than 100 are preferably used.
  • Branched fatty acids are understood to mean those monocarboxylic acids whose fat residue is substituted by at least one methyl and / or ethyl residue. Typical examples are isopalmitic and isostearic acid. Those branched fatty acids which are obtained as a monomer fraction in the dimerization of unsaturated fatty acids having 16 to 18 carbon atoms in the presence of bentonites or montmorillonites are preferably used.
  • the triglycerides and the branched fatty acids can each be used in a molar ratio of 1: 5 to 5: 1.
  • a molar ratio of triglyceride to branched fatty acid or triglyceride to glycerin of 1: 1 to 1: 3 has proven to be optimal.
  • the simultaneous esterification and transesterification can be carried out in a manner known per se, alkali metal, tin and / or zinc compound being suitable as catalysts.
  • Typical examples are sodium hydroxide, potassium hydroxide, tin oxalate and zinc acetate.
  • the catalysts can be used in amounts of 0.01 to 3, preferably 0.02 to 0.4% by weight, based on the triglycerides.
  • fatty acid glycerol esters it is advisable to mix the mixture of triglyceride, branched fatty acid, glycerol and catalyst in a stirred reactor within 4 to 25, preferably 4 to 20 hours at a reduced pressure of 1 to 50, preferably 5 to 25 mmHg to a temperature of 180 to 250, preferably 200 to 240 ° C. If necessary, undesired autoxidation of the feed materials by covering with inert gas can be largely avoided.
  • the crude reaction product is advantageously with an adsorption or. Filter aids such as activated clay are added in order to separate acidic and discolored components and other impurities together with the catalyst.
  • new fatty acid glycerol esters are formed, which on average contain at least one branched fatty acid.
  • the fatty acid glycerol esters according to the invention have a surprisingly low pour point of less than 5 ° C., a low viscosity of 30 to 100 est (Ubbelohde viscometer, 40 ° C.) and excellent lubricating properties.
  • Another object of the invention therefore relates to the use of the fatty acid glycerol esters according to the invention for the production of lubricants, such as rolling and drawing oils, lubricating oils for metalworking and textile finishing and additives for polyvinyl chloride, in which they are present in amounts of 1 to 100, preferably 10 to 50,% by weight .-% - based on the funds - may be included.
  • lubricants such as rolling and drawing oils, lubricating oils for metalworking and textile finishing and additives for polyvinyl chloride, in which they are present in amounts of 1 to 100, preferably 10 to 50,% by weight .-% - based on the funds - may be included.
  • a mixture of 2000 g (.2.2 mol) of beef tallow (AI), 2000 g (6.4 mol) of fatty acid (B1), 200 g (2nd.) was placed in a 3-1 four-necked flask with stirrer, internal thermometer, water separator and gas inlet tube , 2 mol) of glycerol and 0.48 g of tin oxalate - corresponding to 0.024% by weight, based on the beef tallow - and heated to 230 ° C. within 90 minutes.
  • a vacuum of 20 mmHg was then applied and the reaction mixture was stirred at this temperature for 20 hours under reduced pressure.
  • the crude product was then cooled, 20 g of filter aid (Celite (R) ) and activated clay were added, the mixture was stirred for a further hour at 100 ° C. and 5 mmHg and filtered.
  • Example 2 Analogously to Example 1, 1000 g (1.1 mol) of beef tallow (A2), 1000 (3.2 mol) g of fatty acid (B1), 100 g (1.1 mol) of glycerol and 0.7 g of tin oxalate - corresponding to 0.07 Wt .-% based on the beef tallow - submitted.
  • the reaction mixture was pressurized with nitrogen and heated to 150 ° C. in the course of 90 min, during which condensation water was continuously distilled off and removed from the equilibrium. The mixture was then heated to 230 ° C. in the course of 27 minutes and stirred at this temperature for a further hour. A vacuum of 25 mmHg was then applied and the mixture was stirred for a further 18 h.
  • Working up was carried out analogously to Example 1. Characteristics of the product:
  • Example 2 Analogously to Example 2, 1000 g (1.1 mol) of palm oil (A3), 1000 g of fatty acid (B1), 103 g (1.1 mol) of glycerol and 0.7 g of tin oxalate were covered with nitrogen and at 230 ° within 2 h C. heated. The product was then stirred for a further hour, a vacuum of 20 mmHg was applied and 12 was stirred again. The crude product was worked up analogously to Example 1.

Abstract

Fatty acid glycerin esters having improved rheological properties are obtained by simultaneously esterifying and transesterifying in a known manner a mixture containing: (a) triglycerides having formula (I), in which R1CO, R2CO and R3CO stand independently from each other for linear acyl residues with 6 to 24 carbon atoms and 0 or 1 to 3 double bonds; (b) branched fatty acids having the formula (II): R4CO-OH, in which R4CO stands for a branched acyl residue with 16 to 22 carbon atoms and 0 or 1 to 3 double bonds; and (c) glycerin.

Description

Fettsäureglycerinester  Fatty acid glycerol esters
mit verbesserten rheologischen Eigenschaften  with improved rheological properties
Gebiet der Erfindung Field of the Invention
Die Erfindung betrifft Fettsäureglycerinester mit verbesserten rheologischen Eigenschaften, ein Verfahren zu ihrer Herstellung, bei dem man Triglyceride linearer Fettsäuren, verzweigte Fettsäuren und Glycerin in an sich bekannter Weise einer gleichzeitigen Veresterung und Umesterung unterwirft sowie die Verwendung dieser Produkte zur Herstellung von Schmiermitteln. The invention relates to fatty acid glycerol esters with improved rheological properties, a process for their preparation in which triglycerides of linear fatty acids, branched fatty acids and glycerol are subjected to simultaneous esterification and transesterification in a manner known per se, and the use of these products for the production of lubricants.
Stand der Technik State of the art
Tierische Fette und Öle, wie beispielsweise Rindertalg oder Schweineschmalz, sind als Grundöl für die Herstellung von Walzölen, Metallbehandlungsmitteln, AvivagemitteIn oder PVC- Additiven bekannt. Sie weisen jedoch den schwerwiegenden technischen Nachteil auf, daß sie bei niedrigen Temperaturen unzureichende Fließeigenschaften besitzen und somit beispielsweise im Winter oder in kalten Gegenden nur eingeschränkt eingesetzt werden können. Animal fats and oils, such as beef tallow or lard, are known as base oils for the production of rolling oils, metal treatment agents, finishing agents, or PVC additives. However, they have the serious technical disadvantage that they have inadequate flow properties at low temperatures and can therefore only be used to a limited extent, for example in winter or in cold regions.
Die Aufgabe der Erfindung bestand nun darin, Fettsäureglycerinester zur Verfügung zu stellen, die frei von den geschilderten Nachteilen sind. The object of the invention was to provide fatty acid glycerol esters which are free from the disadvantages described.
Beschreibung der Erfinduno Description of the invention
Gegenstand der Erfindung sind Fettsäureglycerinester mit verbesserten rheologischen Eigenschaften, dadurch erhältlich, daß man eine Mischung enthaltend a) Triglyceride der Formel (I), The invention relates to fatty acid glycerol esters with improved rheological properties, obtainable by containing a mixture a) triglycerides of the formula (I),
Figure imgf000004_0001
Figure imgf000004_0001
in der R1CO, R2CO und R3CO unabhängig voneinander für lineare Acylreste mit 6 bis 24 Kohlenstoffatomen und 0 oder 1 bis 5 Doppelbindungen stehen, b) verzweigte Fettsäuren der Formel (II), in which R 1 CO, R 2 CO and R 3 CO independently of one another represent linear acyl radicals having 6 to 24 carbon atoms and 0 or 1 to 5 double bonds, b) branched fatty acids of the formula (II),
R4CO-OH (II) in der R4CO für einen verzweigten Acylrest mit 16 bis 22 Kohlenstoffatomen und 0 oder 1 bis 3 Doppelbindungen steht, und c) Glycerin in an sich bekannter Weise einer gleichzeitigen Veresterung und Umesterung unterwirft. R 4 CO-OH (II) in which R 4 CO represents a branched acyl radical having 16 to 22 carbon atoms and 0 or 1 to 3 double bonds, and c) subjecting glycerol to simultaneous esterification and transesterification in a manner known per se.
Überraschenderweise wurde gefunden, daß die auf diesem Wege hergestellten Fettsäureglycerinester niedrigviskos sind, hervorragende Schmiereigenschaften sowie niedrige Stockpunkte besitzen und sich damit vorteilhaft von natürlichen Triglyceriden gleicher Kettenlänge unterscheiden. Surprisingly, it was found that the fatty acid glycerol esters produced in this way are low-viscosity, have excellent lubricating properties and low pour points, and are therefore advantageously different from natural triglycerides of the same chain length.
Ein weiterer Gegenstand der Erfindung betrifft ein Verfahren zur Herstellung von Fettsäureglycerinestern mit verbesserten rheologischen Eigenschaften, bei dem man eine Mischung enthaltend a) Triglyceride der Formel ( I ) , Another object of the invention relates to a process for the preparation of fatty acid glycerol esters with improved rheological properties, in which one contains a mixture a) triglycerides of the formula (I),
Figure imgf000005_0001
Figure imgf000005_0002
in der R1CO, R2CO und R3CO unabhängig voneinander für lineare Acylreste mit 6 bis 24 Kohlenstoffatomen und 0 oder 1 bis 5 Doppelbindungen stehen, b) verzweigte Fettsäuren der Formel (II),
Figure imgf000005_0001
Figure imgf000005_0002
in which R 1 CO, R 2 CO and R 3 CO independently of one another represent linear acyl radicals having 6 to 24 carbon atoms and 0 or 1 to 5 double bonds, b) branched fatty acids of the formula (II),
R4CO-OH (II) in der R4CO für einen verzweigten Acylrest mit 16 bis 22 Kohlenstoffatomen und 0 oder 1 bis 3 Doppelbindungen steht, und c) Glycerin R 4 CO-OH (II) in which R 4 CO represents a branched acyl radical having 16 to 22 carbon atoms and 0 or 1 to 3 double bonds, and c) glycerol
in an sich bekannter Weise einer gleichzeitigen Veresterung und Umesterung unterwirft. subject to simultaneous esterification and transesterification in a manner known per se.
Triglyceride, die als Einsatzkomponente a) in Betracht kommen, können synthetischer Natur sein. Vorzugsweise werden jedoch natürliche Fette und/oder Öle eingesetzt, die sich überwiegend, d. h. zu mehr als 95 % von linearen Fettsäuren mit 6 bis 24 Kohlenstoffatomen und 0 oder 1 bis 5 Triglycerides that can be used as component a) can be synthetic in nature. However, natural fats and / or oils are preferably used, which are predominantly, ie. H. more than 95% of linear fatty acids with 6 to 24 carbon atoms and 0 or 1 to 5
Doppelbindungen ableiten. Typische Beispiele für Fettsäuren aus denen die genannten Triglyceride aufgebaut sein können, sind Capronsäure, Caprylsäure, Caprinsäure, Laurinsäure, Myristinsäure, Palmitinsäure, Palmoleinsäure, Stearinsäure, Ölsäure, Elaidinsäure, Petroselinsäure, Linolsäure, Derive double bonds. Typical examples of fatty acids from which the triglycerides mentioned can be constructed are caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid,
Linolen- säure, Arachinsäure, Gadoleinsäure, Arachidonsäure, Behensäure, Linolenic acid, arachidic acid, gadoleic acid, arachidonic acid, behenic acid,
Erucasäure und Clupanodonsäure. Des weiteren können auch hydroxysubstituierte Fettsäuren, wie beispielsweise Ricinolsäure oder 12-Hydroxystearinsäure, eingesetzt werden. Bevorzugt sind Triglyceride, die sich ganz oder überwiegend von Fettsäuren mit 12 bis 18 Kohlenstoffatomen und 0 oder 1 Erucic acid and clupanodonic acid. Furthermore, hydroxy-substituted fatty acids such as ricinoleic acid or 12-hydroxystearic acid can also be used. Preferred are triglycerides which are wholly or predominantly derived from fatty acids having 12 to 18 carbon atoms and 0 or 1
Doppelbindung ableiten. Typische Beispiele für Triglyceride, die im Sinne der Erfindung als Ausgangsstoffe in Betracht kommen, sind Olivenöl, Erdnußöl, Baumwollsaatöl, Sonnenblumenöl, Rapsöl, Meadowfoamöl, Ricinusöl, Leinöl, Sojaöl, Babassuöl, Fischöl und insbesondere Palmöl, Palmkernöl, Kokosöl, Rindertalg und Schweineschmalz. Vorzugsweise werden solche Triglyceride eingesetzt, die eine Iodzahl kleiner 100 aufweisen. Derive double bond. Typical examples of triglycerides which are suitable as starting materials in the context of the invention are olive oil, peanut oil, cottonseed oil, sunflower oil, rapeseed oil, meadowfoam oil, castor oil, linseed oil, soybean oil, babassu oil, fish oil and in particular palm oil, palm kernel oil, coconut oil, beef tallow and lard. Those triglycerides which have an iodine number of less than 100 are preferably used.
Unter verzweigten Fettsäuren sind solche Monocarbonsäuren zu verstehen, deren Fettrest mit mindestens einem Methyl- und/ oder Ethylrest substituiert ist. Typische Beispiele sind Isopalmitin- und Isostearinsäure. Bevorzugt eingesetzt werden solche verzweigten Fettsäuren, die als Monomer- fraktion bei der Dimerisierung ungesättigter Fettsäuren mit 16 bis 18 Kohlenstoffatomen in Gegenwart von Bentoniten oder Montmorilloniten anfallen. Technische Fettsäuren der genannten Art werden beispielsweise unter der Bezeichnung "Aliphat(R) 47" (Henkel Hakusui), "Haridime(R)" (Harima Chem.), "Emer- sol(R) 871, 875" (Henkel Corp.) und "Prisorine(R) 3505" (Uni Chema) vertrieben und enthalten mindestens 40 Gew.-% verzweigte Anteile. Branched fatty acids are understood to mean those monocarboxylic acids whose fat residue is substituted by at least one methyl and / or ethyl residue. Typical examples are isopalmitic and isostearic acid. Those branched fatty acids which are obtained as a monomer fraction in the dimerization of unsaturated fatty acids having 16 to 18 carbon atoms in the presence of bentonites or montmorillonites are preferably used. Technical fatty acids of the type mentioned are known, for example, under the name "Aliphat (R) 47" (Henkel Hakusui), "Haridime (R)" (Harima Chem.), "Emerald (R) 871, 875" (Henkel Corp.) and "Prisorine (R) 3505" (Uni Chema) and contain at least 40% by weight of branched portions.
Die Triglyceride und die verzweigten Fettsäuren können ebenso wie die Triglyceride und das Glycerin jeweils im molaren Verhältnis von 1 : 5 bis 5 : 1 eingesetzt werden. Als optimal hat sich ein molares Einsatzverhältnis von Triglycerid zu verzweigter Fettsäure bzw. Triglycerid zu Glycerin von jeweils 1 : 1 bis 1 : 3 erwiesen. The triglycerides and the branched fatty acids, like the triglycerides and the glycerol, can each be used in a molar ratio of 1: 5 to 5: 1. A molar ratio of triglyceride to branched fatty acid or triglyceride to glycerin of 1: 1 to 1: 3 has proven to be optimal.
Die gleichzeitige Veresterung und Umesterung kann in an sich bekannter Weise erfolgen, wobei als Katalysatoren Alkali-, Zinn- und/oder Zinkverbindung in Betracht kommen. Typische Beispiele sind Natriumhydroxid, Kaliumhydroxid, Zinnoxalat und Zinkacetat. Die Katalysatoren können in Mengen von 0,01 bis 3, vorzugsweise 0,02 bis 0,4 Gew.-% - bezogen auf die Triglyceride - eingesetzt werden. The simultaneous esterification and transesterification can be carried out in a manner known per se, alkali metal, tin and / or zinc compound being suitable as catalysts. Typical examples are sodium hydroxide, potassium hydroxide, tin oxalate and zinc acetate. The catalysts can be used in amounts of 0.01 to 3, preferably 0.02 to 0.4% by weight, based on the triglycerides.
Zur Herstellung der erfindungsgemäßen Fettsäureglycerinester empfiehlt es sich, die Mischung aus Triglycerid, verzweigter Fettsäure, Glycerin und Katalysator in einem Rührreaktor innerhalb von 4 bis 25, vorzugsweise 4 bis 20 h bei einem verminderten Druck von 1 bis 50, vorzugsweise 5 bis 25 mmHg auf eine Temperatur von 180 bis 250, vorzugsweise 200 bis 240°C zu erhitzen. Falls erforderlich, kann eine unerwünschte Autoxidation der Einsatzstoffe durch Abdeckung mit Inertgas weitgehend vermieden werden. Das rohe Umsetzungsprodukt wird vorteilhafterweise mit einem Adsorptionsbzw. Filterhilfsmittel wie beispielsweise aktiviertem Ton versetzt, um saure und verfärbte Komponenten sowie andere Verunreinigungen zusammen mit dem Katalysator abzutrennen. To prepare the fatty acid glycerol esters according to the invention, it is advisable to mix the mixture of triglyceride, branched fatty acid, glycerol and catalyst in a stirred reactor within 4 to 25, preferably 4 to 20 hours at a reduced pressure of 1 to 50, preferably 5 to 25 mmHg to a temperature of 180 to 250, preferably 200 to 240 ° C. If necessary, undesired autoxidation of the feed materials by covering with inert gas can be largely avoided. The crude reaction product is advantageously with an adsorption or. Filter aids such as activated clay are added in order to separate acidic and discolored components and other impurities together with the catalyst.
Im Verlauf der gleichzeitigen Veresterung und Umesterung des Gemisches aus Triglycerid, verzweigter Fettsäure und Glycerin kommt es zur Bildung neuer Fettsäureglycerinester, die im statistischen Mittel mindestens eine verzweigte Fettsäure enthalten. In the course of the simultaneous esterification and transesterification of the mixture of triglyceride, branched fatty acid and glycerin, new fatty acid glycerol esters are formed, which on average contain at least one branched fatty acid.
Gewerbliche Anwendbarkeit Industrial applicability
Die erfindungsgemäßen Fettsäureglycerinester weisen einen überraschend niedrigen Stockpunkt von kleiner 5°C, eine geringe Viskosität von 30 bis 100 est (Ubbelohde Viskosimeter, 40°C) und ausgezeichnete Schmiereigenschaften auf. The fatty acid glycerol esters according to the invention have a surprisingly low pour point of less than 5 ° C., a low viscosity of 30 to 100 est (Ubbelohde viscometer, 40 ° C.) and excellent lubricating properties.
Ein weiterer Gegenstand der Erfindung betrifft daher die Verwendung der erfindungsgemäßen Fettsäureglycerinester für die Herstellung von Schmiermitteln, wie Walz- und Ziehölen, Schmierölen für die Metallbearbeitung und Textilavivage sowie Additiven für Polyvinylchlorid, in denen sie in Mengen von 1 bis 100, vorzugsweise 10 bis 50 Gew.-% - bezogen auf die Mittel - enthalten sein können. Another object of the invention therefore relates to the use of the fatty acid glycerol esters according to the invention for the production of lubricants, such as rolling and drawing oils, lubricating oils for metalworking and textile finishing and additives for polyvinyl chloride, in which they are present in amounts of 1 to 100, preferably 10 to 50,% by weight .-% - based on the funds - may be included.
Die folgenden Beispiele sollen den Gegenstand der Erfindung näher erläutern, ohne ihn darauf einzuschränken. The following examples are intended to explain the subject matter of the invention in more detail without restricting it.
Beispiele Examples
I. Eingesetzte Substanzen I. Substances used
AI) Rindertalg I AI) Beef tallow I
Herkunft : Fa.Miyoshi Oil & Fat, Japan  Origin: Miyoshi Oil & Fat, Japan
Säurezahl : 4,0  Acid number: 4.0
Verseifungszahl : 197,4  Saponification number: 197.4
lodzahl : 47,8  Iodine number: 47.8
Schmelzpunkt : 42,1°C  Melting point: 42.1 ° C
A2) Rindertalg II A2) Beef tallow II
Herkunft : Fa.Shikoku Oil & Fat, Japan  Origin: Shikoku Oil & Fat, Japan
Säurezahl : 1,7  Acid number: 1.7
Verseifungszahl : 195,0  Saponification number: 195.0
lodzahl : 49,2  Iodine number: 49.2
Schmelzpunkt : 42,8°C  Melting point: 42.8 ° C
A3) Palmöl A3) Palm oil
Herkunft : Fa.Jomalina, Japan  Origin: Faom Jomalina, Japan
Säurezahl : 2,0  Acid number: 2.0
Verseifungszahl : 198,2  Saponification number: 198.2
lodzahl : 51,1  Iodine number: 51.1
Schmelzpunkt : 43,5°C  Melting point: 43.5 ° C
A4) C16/18-Talgfettsäure A4) C 16/18 tallow fatty acid
Herkunft : Fa.Miyoshi Oil & Fat, Japan  Origin: Miyoshi Oil & Fat, Japan
Säurezahl : 205,27  Acid number: 205.27
Verseifungszahl : 206,1  Saponification number: 206.1
lodzahl : 50,8  Iodine number: 50.8
Schmelzpunkt : 42,1°C  Melting point: 42.1 ° C
Bl) Verzweigte Cjö/is-Fettsäure Bl) Branched Cjö / is fatty acid
Herkunft : Aliphat(R), Fa.Henkel Hakusui, Japan Säurezahl : 180 Origin: Aliphat (R) , Fa. Henkel Hakusui, Japan Acid number: 180
lodzahl : 70 II . Herstel lungsbeispiele Iodine number: 70 II. Manufacturing examples
Beispiel 1 : Example 1 :
In einem 3-1-Vierhalskolben mit Rührer, Innernthermometer, Wasserabscheider und Gaseinleitungsrohr wurde eine Mischung von 2000 g (.2,2 mol) Rindertalg (AI), 2000 g (6,4 mol) Fettsäure (Bl), 200 g (2,2 mol) Glycerin und 0,48 g Zinnoxalat - entsprechend 0,024 Gew.-% bezogen auf den Rindertalg - vorgelegt und innerhalb von 90 min auf 230°C erhitzt. Anschließend wurde ein Vakuum von 20 mmHg angelegt und die Reaktionsmischung bei dieser Temperatur über einen Zeitraum von 20 h unter vermindertem Druck gerührt. Danach wurde das Rohprodukt abgekühlt, mit jeweils 20 g Filterhilfsmittel (Celite(R)) und aktiviertem Ton versetzt, eine weitere Stunde bei 100°C und 5 mmHg gerührt und filtriert. A mixture of 2000 g (.2.2 mol) of beef tallow (AI), 2000 g (6.4 mol) of fatty acid (B1), 200 g (2nd.) Was placed in a 3-1 four-necked flask with stirrer, internal thermometer, water separator and gas inlet tube , 2 mol) of glycerol and 0.48 g of tin oxalate - corresponding to 0.024% by weight, based on the beef tallow - and heated to 230 ° C. within 90 minutes. A vacuum of 20 mmHg was then applied and the reaction mixture was stirred at this temperature for 20 hours under reduced pressure. The crude product was then cooled, 20 g of filter aid (Celite (R) ) and activated clay were added, the mixture was stirred for a further hour at 100 ° C. and 5 mmHg and filtered.
Kenndaten des Produktes; Product characteristics;
Säurezahl : 0,8  Acid number: 0.8
Verseifungszahl : 178,0  Saponification number: 178.0
Hydroxylzahl : 8,1  Hydroxyl number: 8.1
Viskosität* : 52 cst  Viscosity *: 52 cst
Stockpunkt : 0°C  Pour point: 0 ° C
*) Die Viskosität wurde in einem Ubbelohde-Viskosimeter bei 40°C bestimmt. *) The viscosity was determined in an Ubbelohde viscometer at 40 ° C.
Beispiel 2: Example 2:
Analog Beispiel 1 wurden 1000 g (1,1 mol) Rindertalg (A2), 1000 (3,2 mol) g Fettsäure (Bl), 100 g (1,1 mol) Glycerin und 0,7 g Zinnoxalat - entsprechend 0,07 Gew.-% bezogen auf den Rindertalg - vorgelegt. Die Reaktionsmischung wurde mit Stickstoff beaufschlagt und innerhalb von 90 min auf 150°C erhitzt, wobei anfallendes Kondensationswasser kontinuierlich abdesti liiert und aus dem Gleichgewicht entfernt wurde. Anschließend wurde die Mischung innerhalb von 27 min auf 230°C erhitzt und eine weitere Stunde bei dieser Temperatur gerührt. Danach wurde ein Vakuum von 25 mmHg angelegt und weitere 18 h gerührt. Die Aufarbeitung erfolgte analog Beispiel 1. Kenndaten des Produktes : Analogously to Example 1, 1000 g (1.1 mol) of beef tallow (A2), 1000 (3.2 mol) g of fatty acid (B1), 100 g (1.1 mol) of glycerol and 0.7 g of tin oxalate - corresponding to 0.07 Wt .-% based on the beef tallow - submitted. The reaction mixture was pressurized with nitrogen and heated to 150 ° C. in the course of 90 min, during which condensation water was continuously distilled off and removed from the equilibrium. The mixture was then heated to 230 ° C. in the course of 27 minutes and stirred at this temperature for a further hour. A vacuum of 25 mmHg was then applied and the mixture was stirred for a further 18 h. Working up was carried out analogously to Example 1. Characteristics of the product:
Ausbeute : 97,5 % der Theorie Yield: 97.5% of theory
Säurezahl : 0,69  Acid number: 0.69
Verseifungszahl : 187,3  Saponification number: 187.3
Hydroxylzahl : 6,99  Hydroxyl number: 6.99
Viskosität : 52,6 cst  Viscosity: 52.6 cst
Stockpunkt : 0°C  Pour point: 0 ° C
Beispiel 3: Example 3:
Analog Beispiel 2 wurden 1000 g (1,1 mol) Palmöl (A3), 1000 g Fettsäure (Bl), 103 g (1,1 mol) Glycerin und 0,7 g Zinnoxalat mit Stickstoff abgedeckt und innerhalb von 2 h auf 230°C erhitzt. Anschließend wurde das Produkt für eine weitere Stunde gerührt, ein Vakuum von 20 mmHg angelegt und abermals 12 gerührt. Die Aufarbeitung des Rohproduktes erfolgte analog Beispiel 1. Analogously to Example 2, 1000 g (1.1 mol) of palm oil (A3), 1000 g of fatty acid (B1), 103 g (1.1 mol) of glycerol and 0.7 g of tin oxalate were covered with nitrogen and at 230 ° within 2 h C. heated. The product was then stirred for a further hour, a vacuum of 20 mmHg was applied and 12 was stirred again. The crude product was worked up analogously to Example 1.
Kenndaten des Produktes: Characteristics of the product:
Säurezahl : 0,9 Acid number: 0.9
Verseifungszahl : 189,2  Saponification number: 189.2
Hydroxylzahl : 9,5  Hydroxyl number: 9.5
Viskosität : 53,5 cst  Viscosity: 53.5 cst
Stockpunkt : 0°C  Pour point: 0 ° C
Vergleichsbeispiel VI: Comparative Example VI:
Analog Beispiel 2 wurden 1000 g (3,7 mol) Ci6/i8~Talgfettsäure (A4), 1110 g (3,6 mol) Fettsäure (Bl), 228,7 (2,5 mol) Glycerin über einen Zeitraum von 13 h bei einer Temperatur von 230°C und einem verminderten Druck von 25 πrniHg gerührt. Analogously to Example 2, 1000 g (3.7 mol) of Ci6 / 18 tallow fatty acid (A4), 1110 g (3.6 mol) of fatty acid (B1), 228.7 (2.5 mol) of glycerol were used over a period of 13 hours stirred at a temperature of 230 ° C and a reduced pressure of 25 πrniHg.
Kenndaten des Produktes: Characteristics of the product:
Ausbeute : 97,0 % der Theorie Yield: 97.0% of theory
Säurezahl : 0,60  Acid number: 0.60
Verseifungszahl : 186,2  Saponification number: 186.2
Hydroxylzahl : 9,81  Hydroxyl number: 9.81
Viskosität : 52,6 cst  Viscosity: 52.6 cst
Stockpunkt : 11°C  Pour point: 11 ° C

Claims

Patentansprüche Claims
1. Fettsäureglycerinester mit verbesserten rheologischen Eigenschaften, dadurch erhältlich, daß man eine Mischung enthaltend a) Triglyceride der Formel (I), 1. fatty acid glycerol esters with improved rheological properties, obtainable by preparing a mixture comprising a) triglycerides of the formula (I),
Figure imgf000013_0001
Figure imgf000013_0001
in der R1CO, R2CO und R3CO unabhängig voneinander für lineare Acylreste mit 6 bis 24 Kohlenstoffatomen und 0 oder 1 bis 5 Doppelbindungen stehen, b) verzweigte Fettsäuren der Formel (II), in which R 1 CO, R 2 CO and R 3 CO independently of one another represent linear acyl radicals having 6 to 24 carbon atoms and 0 or 1 to 5 double bonds, b) branched fatty acids of the formula (II),
R4CO-OH (II) in der R4CO für einen verzweigten Acylrest mit 16 bis 22 Kohlenstoffatomen und 0 oder 1 bis 3 Doppelbindungen steht, und c) Glycerin in an sich bekannter Weise einer gleichzeitigen Veresterung und Umesterung unterwirft. R 4 CO-OH (II) in which R 4 CO represents a branched acyl radical having 16 to 22 carbon atoms and 0 or 1 to 3 double bonds, and c) subjecting glycerol to simultaneous esterification and transesterification in a manner known per se.
2. Verfahren zur Herstellung von Fettsäureglycerinestern mit verbesserten rheologischen Eigenschaften, bei dem man eine Mischung enthaltend a) Triglyceride der Formel (I), 2. A process for the preparation of fatty acid glycerol esters with improved rheological properties, in which a mixture containing a) triglycerides of the formula (I),
Figure imgf000014_0001
in der R^-CO, R2C0 und R3C0 unabhängig voneinander für lineare Acylreste mit 6 bis 24 Kohlenstoffatomen und 0 oder 1 bis 5 Doppelbindungen stehen, b) verzweigte Fettsäuren der Formel (II),
Figure imgf000014_0001
in which R ^ -CO, R 2 C0 and R 3 C0 independently of one another represent linear acyl radicals having 6 to 24 carbon atoms and 0 or 1 to 5 double bonds, b) branched fatty acids of the formula (II),
R4CO-OH (II) in der R4CO für einen verzweigten Acylrest mit 16 bis 22 Kohlenstoffatomen und 0 oder 1 bis 3 Doppelbindungen steht, und c) Glycerin in an sich bekannter Weise einer gleichzeitigen Veresterung und Umesterung unterwirft. R 4 CO-OH (II) in which R 4 CO represents a branched acyl radical having 16 to 22 carbon atoms and 0 or 1 to 3 double bonds, and c) subjecting glycerol to simultaneous esterification and transesterification in a manner known per se.
3. Verfahren nach Anspruch 2, dadurch gekennzeichnet, daß man Triglyceride ausgewählt aus der Gruppe, die von Palmöl, Palmkernöl, Kokosölgebildet, Rindertalg und Schweineschmalz gebildet wird, einsetzt. 3. The method according to claim 2, characterized in that triglycerides selected from the group consisting of palm oil, palm kernel oil, coconut oil, beef tallow and lard are used.
4. Verfahren nach Anspruch 2, dadurch gekennzeichnet, daß man als verzweigte Fettsäuren die Monomerfraktion aus der Dimerisierung ungesättigter Fettsäuren mit 16 bis 22 Kohlenstoffatomen einsetzt. 4. The method according to claim 2, characterized in that the monomer fraction from the dimerization of unsaturated fatty acids having 16 to 22 carbon atoms is used as branched fatty acids.
5. Verfahren nach Anspruch 2, dadurch gekennzeichnet, daß man die Triglyceride und die verzweigten Fettsäuren im molaren Verhältnis von 1 : 5 bis 5 : 1 einsetzt. 5. The method according to claim 2, characterized in that the triglycerides and the branched fatty acids are used in a molar ratio of 1: 5 to 5: 1.
6. Verfahren nach Anspruch 2, dadurch gekennzeichnet, daß man die Triglyceride und das Glycerin im molaren Verhältnis von 1 : 5 bis 5 : 1 einsetzt. 6. The method according to claim 2, characterized in that the triglycerides and glycerol are used in a molar ratio of 1: 5 to 5: 1.
7. Verfahren nach Anspruch 2, dadurch gekennzeichnet, daß man die Umsetzung in Gegenwart einer Alkali-, Zinn-und/oder Zinkverbindung durchführt. 7. The method according to claim 2, characterized in that one carries out the reaction in the presence of an alkali, tin and / or zinc compound.
8. Verfahren nach Anspruch 7, dadurch gekennzeichnet, daß man die Alkali-, Zinn- und/oder Zinkverbindungen in Mengen von 0,01 bis 3 Gew.-% - bezogen auf die Triglyceride - einsetzt. 8. The method according to claim 7, characterized in that one uses the alkali, tin and / or zinc compounds in amounts of 0.01 to 3 wt .-% - based on the triglycerides.
9. Verfahren nach Anspruch 2, dadurch gekennzeichnet, daß man die Umsetzung gegebenenfalls unter Inertgas bei Temperaturen von 180 bis 250°C durchführt. 9. The method according to claim 2, characterized in that one carries out the reaction optionally under inert gas at temperatures of 180 to 250 ° C.
10. Verfahren nach Anspruch 2, dadurch gekennzeichnet, daß man die Umsetzung bei verminderten Drücken von 1 bis 50 mmHg durchführt. 10. The method according to claim 2, characterized in that one carries out the reaction at reduced pressures of 1 to 50 mmHg.
11. Verwendung der Fettsäureglycerinester nach Anspruch 1 zur Herstellung von Schmiermitteln. 11. Use of the fatty acid glycerol esters according to claim 1 for the production of lubricants.
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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0556995A1 (en) * 1992-02-21 1993-08-25 Castrol Limited Lubricants
EP0594320A1 (en) * 1992-10-17 1994-04-27 Castrol Limited Industrial oils
EP0612831A1 (en) * 1992-12-07 1994-08-31 Idemitsu Kosan Company Limited Flame retardant hydraulic oil
WO2002010114A2 (en) * 2000-08-02 2002-02-07 Mj Research & Development, L.P. Of Which Mjrd, Llc Is A General Partner Transesterified fatty esters for lubricant and refrigerant oil system
EP2011819A1 (en) * 1999-08-19 2009-01-07 Danisco A/S Process
EP1685218A4 (en) * 2003-09-26 2010-12-15 Arizona Chem Fatty acid esters and uses thereof
US8299281B2 (en) 2009-03-27 2012-10-30 Exxonmobil Research And Engineering Company Process for making triglyceride plasticizer from crude glycerol

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997046641A1 (en) * 1996-06-04 1997-12-11 Fuji Oil Co., Ltd. Lube base oil and process for preparing the same
JP4947798B2 (en) * 2007-12-27 2012-06-06 竹本油脂株式会社 Synthetic fiber treatment agent, synthetic fiber treatment method and synthetic fiber
DE102010033035A1 (en) * 2010-08-02 2012-02-02 Emery Oleochemicals Gmbh Lubricant combination for the processing of thermoplastics
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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU30510A1 (en) *
GB820270A (en) * 1956-12-08 1959-09-16 Drew & Co Inc E F Method of treating coconut type oils and the product thereby obtained
US3579548A (en) * 1968-05-10 1971-05-18 Procter & Gamble Triglyceride esters of alpha-branched carboxylic acids
GB2161809A (en) * 1984-07-18 1986-01-22 Institiut Penyelidikan Minyak Carboxylic acid esterification
EP0188725A1 (en) * 1984-12-22 1986-07-30 Hoechst Aktiengesellschaft Process for preparing partial esters of glycerine and condensed glycerine with fatty acids
JPS62290795A (en) * 1986-06-11 1987-12-17 Nippon Steel Corp Cold rolling oil for steel plate

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU30510A1 (en) *
GB820270A (en) * 1956-12-08 1959-09-16 Drew & Co Inc E F Method of treating coconut type oils and the product thereby obtained
US3579548A (en) * 1968-05-10 1971-05-18 Procter & Gamble Triglyceride esters of alpha-branched carboxylic acids
GB2161809A (en) * 1984-07-18 1986-01-22 Institiut Penyelidikan Minyak Carboxylic acid esterification
EP0188725A1 (en) * 1984-12-22 1986-07-30 Hoechst Aktiengesellschaft Process for preparing partial esters of glycerine and condensed glycerine with fatty acids
JPS62290795A (en) * 1986-06-11 1987-12-17 Nippon Steel Corp Cold rolling oil for steel plate

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WORLD PATENTS INDEX LATEST, Sektie Ch, Woche 8805, Derwent Publications Ltd., London, GB; Klasse D, AN 88-032071 & JP,A,62 290 795 (NIPPON STEEL CORP.) 17. Dezember 1987, *

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0556995A1 (en) * 1992-02-21 1993-08-25 Castrol Limited Lubricants
AU652686B2 (en) * 1992-02-21 1994-09-01 Castrol Limited Lubricants
EP0594320A1 (en) * 1992-10-17 1994-04-27 Castrol Limited Industrial oils
EP0612831A1 (en) * 1992-12-07 1994-08-31 Idemitsu Kosan Company Limited Flame retardant hydraulic oil
US6361711B1 (en) * 1992-12-07 2002-03-26 Idemitsu Kosan Co., Ltd. Flame retardant hydraulic oil containing a synthetic ester formed by reaction of a polyol and a mixture of carboxylic acids including oleic acid and isostearic acid
EP2011819A1 (en) * 1999-08-19 2009-01-07 Danisco A/S Process
WO2002010114A2 (en) * 2000-08-02 2002-02-07 Mj Research & Development, L.P. Of Which Mjrd, Llc Is A General Partner Transesterified fatty esters for lubricant and refrigerant oil system
WO2002010114A3 (en) * 2000-08-02 2002-08-15 Mj Res & Dev L P Of Which Mjrd Transesterified fatty esters for lubricant and refrigerant oil system
US7252779B2 (en) 2000-08-02 2007-08-07 Mj Research Limited Partnership Transesterification composition of fatty acid esters, and uses thereof
US7968504B2 (en) 2000-08-02 2011-06-28 MJ Research and Development, LP Transesterification composition of fatty acid esters, and uses thereof
EP1685218A4 (en) * 2003-09-26 2010-12-15 Arizona Chem Fatty acid esters and uses thereof
US8299281B2 (en) 2009-03-27 2012-10-30 Exxonmobil Research And Engineering Company Process for making triglyceride plasticizer from crude glycerol

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