EP2146950A1 - Esters d'acide carboxylique stables à l'oxydation et leur utilisation - Google Patents

Esters d'acide carboxylique stables à l'oxydation et leur utilisation

Info

Publication number
EP2146950A1
EP2146950A1 EP08715680A EP08715680A EP2146950A1 EP 2146950 A1 EP2146950 A1 EP 2146950A1 EP 08715680 A EP08715680 A EP 08715680A EP 08715680 A EP08715680 A EP 08715680A EP 2146950 A1 EP2146950 A1 EP 2146950A1
Authority
EP
European Patent Office
Prior art keywords
acid
fatty acids
carboxylic acid
esters
component
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.)
Withdrawn
Application number
EP08715680A
Other languages
German (de)
English (en)
Inventor
Alfred Westfechtel
Matthias Hof
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.)
Emery Oleochemicals GmbH
Original Assignee
Emery Oleochemicals GmbH
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 Emery Oleochemicals GmbH filed Critical Emery Oleochemicals GmbH
Priority to EP08715680A priority Critical patent/EP2146950A1/fr
Publication of EP2146950A1 publication Critical patent/EP2146950A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
    • C07C69/58—Esters of straight chain acids with eighteen carbon atoms in the acid moiety
    • 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
    • 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
    • C10M105/40—Esters containing free hydroxy or carboxyl groups
    • 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
    • C10M2207/283—Esters of polyhydroxy compounds
    • C10M2207/2835—Esters of polyhydroxy compounds used as base material
    • 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
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
    • 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
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
    • C10M2207/2895—Partial esters containing free hydroxy groups used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/065—Saturated Compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/067—Unsaturated Compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/069—Linear chain compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/64—Environmental friendly compositions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids

Definitions

  • the invention relates to selected carboxylic acid esters and their use as a component of hydraulic oils or in lubricants.
  • Hydraulic systems are used in a variety of technical equipment, such as automobiles, trucks, cranes, trains and other means of transport, but also in agricultural equipment, ships, as well as in industrial and railway sectors.
  • the hydraulic systems contain a hydraulic fluid which traditionally contains petrochemical liquids or esters or other oleochemicals as base fluid. The latter are increasingly preferred because of their biodegradability.
  • polyol esters of fatty acids are known as suitable base fluids for hydraulic oils.
  • WO 97/39086 discloses esters obtained by reacting polyols, including trimethylolpropane, with mixtures of fatty acids, wherein the ratio of short-chain fatty acids to long-chain fatty acids must be in the range of 2: 1 to 1:20. It can be seen from the document that the claimed esters should have advantageous technical properties, in particular because of their low-temperature compatibility.
  • WO 97/39086 requires mixtures of fatty acids, the short-chain portion being selected from the group of C5-C12 fatty acids alone, in the examples exclusively C8-C10 fatty acids.
  • DE 101 15 829 A1 describes oxidation-stable polyol esters which can be prepared by using technical grade oleic acid as acid component.
  • ester systems and hydraulic fluids must, however, also have a high oxidation stability, in particular comes to fruition when the hydraulic oil is exposed to high temperatures in the presence of atmospheric oxygen.
  • antioxidants are added to the hydraulic oils as conventional additives. Decisive in this case is the so-called modified, dry "Turbine oxidation stability test", short TOST dryer according to DIN51587, which tests the stability of strigolen when aged at 95 ° C in the presence of oxygen.
  • Conventional systems reach the critical limit of 2.0 mg KOH / g strigol after only 170 to about 300 hours.
  • oxidation stability there is a continuing need on the part of the industry to be able to provide oxidation-stable oils. The attempt to achieve the desired high oxidation stability by adding further antioxidants has hitherto not been successful.
  • the present application therefore relates to synthetic carboxylic acid esters which contain trimethylolpropane as the alcohol component and a mixture of (i) linear saturated fatty acids having 8 to 18 carbon atoms and (ii) linear mono- or polyunsaturated fatty acids having 12 to 22 carbon atoms wherein the molar ratio of (i): (ii) is in the range of 3: 1 to 1: 3 and preferably in the range of 2: 1 to 1: 3, and more preferably in the range of 1: 1 to 1: 3.
  • An essential technical feature in the preparation of the esters according to the invention is the molar ratio of the fatty acid mixture. Only in the claimed, narrow range from 3: 1 to 1: 3 or preferably 2: 1 to 1: 3 and particularly preferably in the range of 1: 1 to 1: 3, the desired esters are obtained. Another preferred range for the molar ratio (i) to (ii) is 2: 1 to 1: 2, and more preferably 1: 1 to 1: 2.
  • saturated linear fatty acids those with 8 to 18, preferably 8 to 16 and in particular 8 to 14 carbon atoms can be used.
  • mixtures of C8- from C14-acids are used for the synthesis of the esters according to the invention.
  • linear saturated fatty acids (i) to those fatty acid mixtures which contain more than 80% by weight, preferably more than 85% by weight and in particular more than 90% by weight of fatty acids of chain length C-12 to C-18 and preferably C-12 to C-14.
  • Preferred fatty acid mixtures of type (i) are free of fatty acids of chain length C-18.
  • the oleic acid is selected. This can also be used in technical quality, but preferred is a pure oleic acid. Oleic acid is obtained mainly from its natural occurrence in vegetable and animal fats and oils.
  • the triglycerides first one Subjected to pressure splitting and the resulting mixtures of the different fatty acids by the process of the interaction into a saturated fraction (stearin) and an unsaturated, consisting largely of oleic acid portion (olein) separated.
  • a purified oleic acid is used.
  • less suitable is, for example, a technical oleic acid, as obtained, for example, by pressure splitting and subsequent separation from the network.
  • Technical oleic acid typically contains only about 70 wt .-% of monounsaturated oleic acid, the remaining 30 wt .-% also polyunsaturated acids, and unsaturated acids, partially C-18 and C-16 deleted.
  • the present invention advantageously and therefore preferably makes use of pure oleic acid grades containing more than 70%, preferably more than 80% and in particular more than 90% oleic acid.
  • esters in which the molar ratio between the acid component (as the acids of type (i) and (ii) together and the trimethylolpropane in the range of 5: 1 to 1: 1, preferably 2: 1 to 1 : 1 and more preferably 1, 5: 1 to 1: 1, wherein the ratios in the synthesis - ie the molar ratios of the starting compounds are considered here.
  • Another aspect of the present invention relates to the use of the described esters as constituents of a hydraulic oil, and in particular as a base oil or base oil therein.
  • Such hydraulic oils may then preferably contain up to 95% by weight of the esters, but amounts between 25 and 85% by weight are preferred.
  • these oils generally also contain additives, preferably in amounts of from 5 to 25% by weight.
  • the additives are those classes which are known in principle to the person skilled in the art, namely antioxidants, extremely pressure (EP) or anti-wear (AW) additives, corrosion inhibitors, demulsifiers and / or defoamers.
  • non-ferrous metal deactivators may also be included.
  • the additives are in usual amounts, but in total in max.
  • the EP / AW additives in amounts of preferably 0.2 to 2.0 wt .-%, antioxidants in the range of 0.2 to 1.0 wt .-%, anti-corrosion additives in the range of 0.05 to 0.2 Wt .-%, non-ferrous metal deactivators in the range of 0.05 to 0.5 and anti-foam additives defoamers in the range of 0.005 to 0.04% in the hydraulic oils according to the invention.
  • the formulation of such hydraulic oils is carried out by mixing the base liquid with the additives, optionally at elevated temperature.
  • the esters of the present application may also and preferably be used as a component of lubricants.
  • TMP esters 3 to 5 selected according to the invention have the best low-temperature properties compared with esters 1 and 2.
  • Oleic acid 0 11.3 5 C8-C14 / 0 0.4 0.7 10.6 Oleic acid
  • the TMP ester No. 5 according to the invention has an improved oxidation stability compared to a pure oleic acid ester.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)

Abstract

L'invention concerne des esters d'acide carboxylique renfermant, comme constituant alcoolique, du triméthylolpropane et, comme constituant acide, un mélange constitué (i) d'acides gras saturés linéaires possédant 8 à 18 atomes de carbone et (ii) d'acides gras mono- ou polyinsaturés linéaires possédant 12 à 22 atomes de carbone, le rapport molaire (i) : (ii) étant compris entre 3 : 1 et 1 : 3. Lesdits esters possèdent une bonne stabilité à l'oxydation et peuvent être utilisés comme huiles de base pour huiles hydrauliques.
EP08715680A 2007-02-02 2008-02-01 Esters d'acide carboxylique stables à l'oxydation et leur utilisation Withdrawn EP2146950A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP08715680A EP2146950A1 (fr) 2007-02-02 2008-02-01 Esters d'acide carboxylique stables à l'oxydation et leur utilisation

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP07002256A EP1958931A1 (fr) 2007-02-02 2007-02-02 Esters d'acides carboxyliques stables à l'oxidation et leur utilisation
PCT/EP2008/000821 WO2008092703A1 (fr) 2007-02-02 2008-02-01 Esters d'acide carboxylique stables à l'oxydation et leur utilisation
EP08715680A EP2146950A1 (fr) 2007-02-02 2008-02-01 Esters d'acide carboxylique stables à l'oxydation et leur utilisation

Publications (1)

Publication Number Publication Date
EP2146950A1 true EP2146950A1 (fr) 2010-01-27

Family

ID=38208392

Family Applications (2)

Application Number Title Priority Date Filing Date
EP07002256A Withdrawn EP1958931A1 (fr) 2007-02-02 2007-02-02 Esters d'acides carboxyliques stables à l'oxidation et leur utilisation
EP08715680A Withdrawn EP2146950A1 (fr) 2007-02-02 2008-02-01 Esters d'acide carboxylique stables à l'oxydation et leur utilisation

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP07002256A Withdrawn EP1958931A1 (fr) 2007-02-02 2007-02-02 Esters d'acides carboxyliques stables à l'oxidation et leur utilisation

Country Status (3)

Country Link
US (1) US20100048931A1 (fr)
EP (2) EP1958931A1 (fr)
WO (1) WO2008092703A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1918354A1 (fr) * 2006-10-13 2008-05-07 Cognis Oleochemicals GmbH Compositions de combustible comprenant de la glycérine
EP2036962A1 (fr) * 2007-09-14 2009-03-18 Cognis Oleochemicals GmbH Additifs pour fluides de forage à base d'eau
DE102008008251A1 (de) * 2008-02-08 2009-08-20 Cognis Oleochemicals Gmbh Vernetzte Glycerin- oder Oligoglycerinester und deren Verwendung als Additiv in Bohrspülungen
DE102012103701A1 (de) * 2012-04-26 2013-10-31 Fuchs Petrolub Ag Ester als Kühl- und Isolierflüssigkeiten für Transformatoren
US10190067B2 (en) * 2016-02-24 2019-01-29 Washington State University High performance environmentally acceptable hydraulic fluid

Family Cites Families (8)

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Publication number Priority date Publication date Assignee Title
FR2187894A1 (en) * 1972-06-12 1974-01-18 Inst Francais Du Petrole Lubricants for 2-stroke and rotary engines - contg high-viscosity simple, complex or ether esters as base lubricant
DE4018228A1 (de) * 1990-06-07 1991-12-12 Henkel Kgaa Fliessfaehige bohrlochbehandlungsmittel auf basis von kohlensaeurediestern
JPH0543888A (ja) * 1991-08-09 1993-02-23 Nippon Quaker Chem Kk 冷間圧延油
JPH06108079A (ja) * 1992-09-29 1994-04-19 Nkk Corp ブリキ用冷間圧延油
JP4020341B2 (ja) * 1997-02-19 2007-12-12 出光興産株式会社 金属加工油組成物
JP4730982B2 (ja) * 1998-03-25 2011-07-20 出光興産株式会社 難燃性油圧作動油
DE10115829A1 (de) * 2001-03-29 2002-10-10 Cognis Deutschland Gmbh Oxidationsstabiles Hydrauliköl
WO2003097774A1 (fr) * 2002-05-15 2003-11-27 Idemitsu Kosan Co., Ltd. Composition d'huile destinee au laminage a froid

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2008092703A1 *

Also Published As

Publication number Publication date
US20100048931A1 (en) 2010-02-25
WO2008092703A1 (fr) 2008-08-07
EP1958931A1 (fr) 2008-08-20

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