[go: up one dir, main page]
More Web Proxy on the site http://driver.im/

WO1992022627A1 - Esters de glycerine d'acides gras a proprietes rheologiques ameliorees - Google Patents

Esters de glycerine d'acides gras a proprietes rheologiques ameliorees Download PDF

Info

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
Authority
WO
WIPO (PCT)
Prior art keywords
triglycerides
carbon atoms
fatty acid
fatty acids
branched
Prior art date
Application number
PCT/EP1992/001227
Other languages
German (de)
English (en)
Inventor
Akira Nakashima
Nagao Totani
Yoshio Kawahara
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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 Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Publication of WO1992022627A1 publication Critical patent/WO1992022627A1/fr

Links

Classifications

    • 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.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

On obtient des esters de glycérine d'acides gras à propriétés rhéologiques améliorées en soumettant à une estérification et à une transestérification simultanées de manière connue en soi un mélange contenant: (a) des triglycérides de la formule (I) dans laquelle R?1CO, R2CO et R3¿CO désignent indépendamment les uns des autres des restes acyle linéaires ayant 6 à 24 atomes de carbone et 0 ou 1 à 3 liaisons doubles ; (b) des acides gras ramifiés de la formule (II): R4CO-OH, dans laquelle R4CO désigne un reste acyle ramifié ayant 16 à 22 atomes de carbone et 0 ou 1 à 3 liaisons doubles; et (c) de la glycérine.
PCT/EP1992/001227 1991-06-11 1992-06-03 Esters de glycerine d'acides gras a proprietes rheologiques ameliorees WO1992022627A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP3/139023 1991-06-11
JP13902391A JPH04363351A (ja) 1991-06-11 1991-06-11 混合グリセリドおよびその製造方法

Publications (1)

Publication Number Publication Date
WO1992022627A1 true WO1992022627A1 (fr) 1992-12-23

Family

ID=15235671

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1992/001227 WO1992022627A1 (fr) 1991-06-11 1992-06-03 Esters de glycerine d'acides gras a proprietes rheologiques ameliorees

Country Status (2)

Country Link
JP (1) JPH04363351A (fr)
WO (1) WO1992022627A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0556995A1 (fr) * 1992-02-21 1993-08-25 Castrol Limited Lubrifiants
EP0594320A1 (fr) * 1992-10-17 1994-04-27 Castrol Limited Huiles industrielles
EP0612831A1 (fr) * 1992-12-07 1994-08-31 Idemitsu Kosan Company Limited Huile hydraulique ignifuge
WO2002010114A2 (fr) * 2000-08-02 2002-02-07 Mj Research & Development, L.P. Of Which Mjrd, Llc Is A General Partner Circuit d'huile lubrifiante et frigorigene
EP2011819A1 (fr) * 1999-08-19 2009-01-07 Danisco A/S Procédé
EP1685218A4 (fr) * 2003-09-26 2010-12-15 Arizona Chem Esters d'acides gras et utilisations associees
US8299281B2 (en) 2009-03-27 2012-10-30 Exxonmobil Research And Engineering Company Process for making triglyceride plasticizer from crude glycerol

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997046641A1 (fr) * 1996-06-04 1997-12-11 Fuji Oil Co., Ltd. Huile de base de lubrification et procede de preparation
JP4947798B2 (ja) * 2007-12-27 2012-06-06 竹本油脂株式会社 合成繊維用処理剤、合成繊維の処理方法及び合成繊維
DE102010033035A1 (de) * 2010-08-02 2012-02-02 Emery Oleochemicals Gmbh Gleitmittelkombination für die Verarbeitung von thermoplastischen Kunststoffen
JP6351569B2 (ja) * 2013-03-29 2018-07-04 松本油脂製薬株式会社 合成繊維用処理剤及びその利用
JP5960885B1 (ja) * 2015-06-30 2016-08-02 松本油脂製薬株式会社 合成繊維用処理剤及びその利用

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU30510A1 (fr) *
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 (fr) * 1984-12-22 1986-07-30 Hoechst Aktiengesellschaft Procédé de préparation d'esters partiels de glycérine et de glycérine condensée avec des acides gras
JPS62290795A (ja) * 1986-06-11 1987-12-17 Nippon Steel Corp 鋼板の冷間圧延油

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU30510A1 (fr) *
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 (fr) * 1984-12-22 1986-07-30 Hoechst Aktiengesellschaft Procédé de préparation d'esters partiels de glycérine et de glycérine condensée avec des acides gras
JPS62290795A (ja) * 1986-06-11 1987-12-17 Nippon Steel Corp 鋼板の冷間圧延油

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 (fr) * 1992-02-21 1993-08-25 Castrol Limited Lubrifiants
AU652686B2 (en) * 1992-02-21 1994-09-01 Castrol Limited Lubricants
EP0594320A1 (fr) * 1992-10-17 1994-04-27 Castrol Limited Huiles industrielles
EP0612831A1 (fr) * 1992-12-07 1994-08-31 Idemitsu Kosan Company Limited Huile hydraulique ignifuge
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 (fr) * 1999-08-19 2009-01-07 Danisco A/S Procédé
WO2002010114A2 (fr) * 2000-08-02 2002-02-07 Mj Research & Development, L.P. Of Which Mjrd, Llc Is A General Partner Circuit d'huile lubrifiante et frigorigene
WO2002010114A3 (fr) * 2000-08-02 2002-08-15 Mj Res & Dev L P Of Which Mjrd Circuit d'huile lubrifiante et frigorigene
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 (fr) * 2003-09-26 2010-12-15 Arizona Chem Esters d'acides gras et utilisations associees
US8299281B2 (en) 2009-03-27 2012-10-30 Exxonmobil Research And Engineering Company Process for making triglyceride plasticizer from crude glycerol

Also Published As

Publication number Publication date
JPH04363351A (ja) 1992-12-16

Similar Documents

Publication Publication Date Title
EP1135998B1 (fr) Utilisation de glycérides synthétiques à base d'acide linoléique conjugué comme antioxydant dans les produits alimentaires
DE69516154T2 (de) Verfahren zur herstellung eines synthetischen esters aus pflanzlichem öl
DE69005501T2 (de) Verfahren zum Herstellen von Niedrigalkylfettsäuremonoester.
EP0593524B1 (fr) Procede de fabrication d'alkylesters inferieurs d'acides gras
WO1996018598A1 (fr) Esters synthetiques constitues d'alcools et de melanges d'acides gras d'huiles vegetales riches en acide oleique et pauvres en acide stearique
DE4242466C2 (de) Verfahren zur Herstellung von Fettalkoholen
WO1992022627A1 (fr) Esters de glycerine d'acides gras a proprietes rheologiques ameliorees
EP2358851B1 (fr) Utilisation de l'acide méthanesulfonique pour la fabrication d'esters d'acide gras
EP0433420B1 (fr) Procede de production de diamides d'acides digras symetriques
WO2003004591A1 (fr) Procede de transesterification de matiere grasse et/ou d'huile par alcoolyse
DE10219781A1 (de) Verfahren zur Herstellung von konjugierten Linolsäureglyceriden
EP0554590B1 (fr) Procédé de préparation de composés d'acides gras hydroxylés
EP0728176B1 (fr) Procede de fabrication d'alkylesters inferieurs d'acides gras
DE4125031C1 (en) Prepn. of hydroxylated fatty acid, used to form polymer - comprises hydrolysing epoxidised fatty acid with oxirane rings in presence of activated catalyst e.g. alumina
DE3916356A1 (de) Verfahren zur herstellung von gemischen aus fettsaeuredialkylendiamiden, fettsaeureestern und gegebenenfalls metallseifen, so erhaltene gemische und ihre verwendung als kunststoffadditive
DE3639857A1 (de) Verfahren zur herstellung von fettsaeurenitrilen und glycerin aus glyceriden
EP1189857B1 (fr) Alcools gras ramifies et largement insatures
EP1075460A1 (fr) Procede de preparation d'esters de polyol
DE19819655A1 (de) Verfahren zur Herstellung von Fettsäureestern aus Triglyceriden
DE3244752A1 (de) Verfahren zur herstellung von fettsaeurenitrilen und glycerin aus glyceriden, insbesondere aus natuerlichen fetten und oelen
WO1992012955A1 (fr) Procede de preparation de substances grasses ramifiees
DE4136278A1 (de) Verfahren zur herstellung verzweigter fettstoffe
DE4330353A1 (de) Poly(meth)acrylate langkettiger, verzweigter Alkanole und ihre Verwendung in Schmiermitteln
WO1991000264A1 (fr) Procede pour la preparation directe sous forme de substance chimique de base a partir de graisses et d'huiles
DE1136686B (de) Verfahren zur Herstellung von als Schmieroele dienenden Mischestern

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): JP US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IT LU MC NL SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
122 Ep: pct application non-entry in european phase