EP0009746A1 - Huiles d'esters modifiées par des lactones et compositions lubrifiantes les contenant - Google Patents

Huiles d'esters modifiées par des lactones et compositions lubrifiantes les contenant Download PDF

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Publication number
EP0009746A1
EP0009746A1 EP79103593A EP79103593A EP0009746A1 EP 0009746 A1 EP0009746 A1 EP 0009746A1 EP 79103593 A EP79103593 A EP 79103593A EP 79103593 A EP79103593 A EP 79103593A EP 0009746 A1 EP0009746 A1 EP 0009746A1
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EP
European Patent Office
Prior art keywords
aliphatic
weight
ester oils
acid
acids
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.)
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Application number
EP79103593A
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German (de)
English (en)
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EP0009746B1 (fr
Inventor
Rolf Dr. Dhein
Karl-Heinz Dr. Hentschel
Karl Dr. Nützel
Klaus Dr. Morche
Wolfgang Schüle
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Bayer AG
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Bayer AG
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    • 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
    • C10M105/42—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic 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
    • C10M101/00—Lubricating compositions characterised by the base-material being a mineral or fatty oil
    • C10M101/02—Petroleum 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
    • 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
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
    • 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
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
    • C10M135/36—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon with nitrogen or oxygen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102—Aliphatic fractions
    • C10M2203/1025—Aliphatic fractions used as base material
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/104—Aromatic fractions
    • C10M2203/1045—Aromatic fractions used as base material
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/106—Naphthenic fractions
    • C10M2203/1065—Naphthenic fractions used as base material
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/108—Residual fractions, e.g. bright stocks
    • C10M2203/1085—Residual fractions, e.g. bright stocks used as base material
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10M2207/2805—Esters 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
    • C10M2207/281—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
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    • 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
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/301—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids used as base material
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • C10M2207/345—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives used as base material
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C10M2215/065—Phenyl-Naphthyl amines
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/066—Arylene diamines
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/067—Polyaryl amine alkanes
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/068—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings having amino groups bound to polycyclic aromatic ring systems, i.e. systems with three or more condensed rings
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106—Thiadiazoles
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108—Phenothiazine
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    • 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
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines

Definitions

  • the present application relates to ester oils from mono- or polyhydric alcohols, di- or monocarboxylic acids and lactones, and to lubricants and lubricant combinations containing these ester oils.
  • Petroleum fractions required for motor oils contain on the one hand very volatile constituents that impair the motor behavior at high working temperatures, and on the other hand substances that become tough or even solid very early in the cold.
  • the improved base oil obtained by separating the volatile and crystallizing fractions by distillation and treatment with urea has a higher viscosity than before, which results in poorer cold behavior as a result of the increased low-temperature viscosities. For this reason, this aftertreatment (solvent refining) of the base oils is often avoided.
  • solvent refining of petroleum fractions has been largely replaced by cheaper hydrorefining, but hydroraffinates also have, albeit to a lesser extent, the above-mentioned disadvantages of solvent refining, e.g. unsatisfactory low-temperature properties.
  • multigrade oils have become increasingly popular, which have good motor behavior in both winter and summer ambient temperatures. These oils have such good viscosity-temperature behavior, e.g. low viscosity changes with the temperatures and a high "viscosity index” (V.I.), which cannot be achieved by the base oil alone.
  • V.I. viscosity index
  • Polymers admixed to the base oil so-called “VI improvers”, significantly increase the basic viscosity and the viscosity index of the lubricating oil mixture, but are gradually destroyed or changed by oxidation processes due to the high shear forces acting on the lubricating film, so that the VI -increasing effect of these additives is lost over time.
  • Ester oils are either dicarboxylic acid esters of straight-chain, but preferably branched monoalcohols, monocarboxylic acid esters of polyalcohols or neutral oligocondensates from monocarboxylic acids and / or dicarboxylic acids and / or polyalcohols ("complex ester oils").
  • Ester oils generally outperform mineral oils more similarly Viscosities due to a lower pour point, a higher flash point, lower volatility and less dependence of the viscosity on the temperature (high viscosity index, VI).
  • esters of trimethyladipic acid with aliphatic C 6 -C 10 alcohols are often also mixed with mineral base oils.
  • mineral base oils predominantly paraffin-based mineral oils often become cloudy at temperatures above 0 ° C when such esters are added, which, depending on the aromatic content, can also occur with mixed-base mineral oils.
  • the motor oils alloyed with such esters can no longer fully perform their function at low temperatures.
  • Special ester oils with kinematic viscosities ⁇ 8 cSt / 210 have been used for machine elements and motors, e.g. turbine engines in aviation, for machines in the ceramic industry, for drum furnaces in the inorganic insulation industry or for chain-transported stenter frames in the textile industry, in which temperatures exceed 170 ° C ° F has been very successful so far.
  • many of these ester oils are still too volatile at temperatures of 170 ° C and above even after the addition of antioxidants.
  • Another disadvantage is the inclination of even the best at the moment. known high-temperature ester oils, already in practice on frequently encountered operating temperatures up to 200 ° C after a few weeks to form so many solid deposits or to increase their viscosity to such an extent that they no longer adequately fulfill their function as lubricants.
  • condensation products from aliphatic mono- or polyhydric alcohols, (cyclo) aliphatic or aromatic mono- or dicarboxylic acids and aliphatic hydroxycarboxylic acids or their lactones are ester oils which do not have the disadvantages of the above-mentioned ester oils and are excellent for blending with mineral base oils own.
  • low molecular weight and therefore shear stable ester oils are characterized by very high viscosity indices, low pour points and good compatibility with mineral base oils. They are therefore very suitable for improving the viscosity index of mineral base oils and for lowering the pour point and increasing the viscosity viscosity of paraffin or naphthenic base oils pretreated in a known manner, so that the addition of polymeric VI improvers can be largely or completely dispensed with.
  • the higher viscosity of the oils according to the invention ( ⁇ 8 cSt / 210 ° F), provided with appropriate antioxidants, have a particularly low volatility at temperatures around 200 ° C and a long service life.
  • the free hydroxycarboxylic acids can also be used to produce the ester oils according to the invention.
  • the more easily accessible 6 to 9-membered lactones of the corresponding aliphatic C 5 -C 12 -hydroxycarboxylic acids are used, such as ⁇ -caprolactone, trimethyl--C-caprolactone, önantholactone and caprylolactone.
  • the lactones of the C 5 -C 6 hydroxycarboxylic acids are preferred, especially the lactones of the hydroxycaproic acids.
  • ⁇ -Caprolactone is particularly preferred.
  • oils with a lactone content higher than 45% by weight or with a C / O ratio lower than 4.1 have less favorable mineral oil tolerances and low temperature properties; in the case of oils containing less than 5% by weight of lactone, the effect which increases the viscosity index and / or the long-term usability at high temperatures is not sufficient.
  • the use of larger proportions of branched, cycloaliphatic or aromatic mono- or dicarboxylic acids or corresponding monoalcohols affects the favorable viscosity-temperature behavior of the oils according to the invention.
  • the higher-viscosity ( ⁇ 8 cSt) of the oils according to the invention have excellent high-temperature properties even at 200 ° C., although they contain ester bonds with free C-H bonds on the ⁇ -carbon of the alcohol component.
  • the ester oils which consist of 5-25% by weight of one or more polyalcohols with 2-12 carbon atoms and two or more alcoholic hydroxyl groups per molecule, 5-45% by weight ⁇ -caprolactone and 35-80% have proven to be particularly advantageous % of one or more aliphatic, straight-chain or slightly branched carboxylic acids with 4-18 carbon atoms, on the other hand the ester oils from 15-45% by weight of preferably straight-chain or slightly branched aliphatic dicarboxylic acids with 4-14 carbon atoms, 5-45% by weight of t-caprolactone and 30-60% by weight of one or more straight-chain or slightly branched monoalcohols with 1-14 carbon atoms, the% by weight information always being 100% complete.
  • Suitable mono-alcohols are those having 1-14, preferably with 4-10 carbon atoms such as M ethanol, ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, 2-ethylhexanol, nonanol, trimethylhexanol, decanol, undecanol, dodecanol, tridecanol, tetradecanol , ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether D-i, Diethylglykolmonoethylether and diethylene glycol monobutyl ether.
  • These alcohols are 5-45% by weight, preferably 10-35% by weight ⁇ -caprolactone, based on the total weight of all the stocks required to build up the finished ester oil parts, by heating to 80-200 C, preferably 130-180 ° C, in the presence of a suitable catalyst to give hydroxycarboxylic esters, which are referred to below as lactone-modified alcohols.
  • the lactone-modified monoalcohols are preferably esterified with aliphatic straight-chain or weakly branched dicarboxylic acids having 4-14, preferably 6-12, carbon atoms.
  • Suitable dicarboxylic acids are e.g. Succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, trimethyladipic acid, sebacic acid, undecanedioic acid, dodecanedioic acid and succinic acids substituted with alkyl radicals.
  • aliphatic mono- or dicarboxylic acids can be replaced by up to 55 mol% with cycloaliphatic C 6 -C 12 mono- or dicarboxylic acids and up to 5 mol% by aromatic C 7 -C 12 mono- or dicarboxylic acids, for example by 6-cyclohexylcaproic acid, cyclohexane carboxylic acid, cyclohexane-1,2-dicarboxylic acid, benzoic acid, phthalic acid and terephthalic acid.
  • esters are preferably suitable as mineral oil additives.
  • esterification of the polyalcohols with a very low molecular weight e.g. ethylene glycol
  • a very low molecular weight e.g. ethylene glycol
  • esters are expediently used which are composed of polyalcohols with higher molecular weights and a larger number of hydroxyl groups and / or longer-chain monocarboxylic acids with a higher degree of branching (such as, for example, cyclohexane carboxylic acid) compared to the ester oils which are used for blending serve with mineral lubricants.
  • the esterification is carried out either by simply heating a 10-30 mol% excess of the carboxylic acid or the carboxylic acid mixture with the lactone-modified multiple alcohols to temperatures of 110-240 ° C., preferably 160-210 ° C., at normal pressure or elevated pressure and separation the water of reaction formed or by azeotropic esterification in the presence of a water-forming solvent such as benzene, chlorobenzene, toluene or xylene and heating to temperatures of 80-240 ° C, preferably 140-210 ° C, with distillation of the azeotrope.
  • a water-forming solvent such as benzene, chlorobenzene, toluene or xylene
  • the lactone-modified monoalcohol is first esterified with an excess of about 5-20 equivalent% of dicarboxylic acid by the process mentioned above up to the lowest possible hydroxyl number, then an excess of the unmodified alcohol is added and the reaction is brought to an end with the lowest possible acid number.
  • Acidic catalysts such as sulfuric acid, phosphoric acid, polyphosphoric acid, hydrogen sulfates, dihydrogen phosphates, aromatic sulfonic acids or trialkyl phosphates can be used in the esterification.
  • any remaining catalyst, monocarboxylic acids or other impurities are removed by treating the crude ester oil with aqueous alkali solutions or finely powdered anhydrous alkalis such as calcium oxide and anhydrous soda or by stripping in a high vacuum.
  • ester oils according to the invention can of course also be composed of more than a single monoalcohol, polyalcohol, monocarboxylic acid or dicarboxylic acid component.
  • esters according to the invention provide valuable lubricants with outstanding service life at 200 ° C or can be added in amounts of 1-90 wt .-% naphthenic, paraffinic or mixed basic mineral base oils, preferably those which are obtained after a dewaxing treatment and after a distillation to remove the volatile constituents , which improves the viscosity-temperature behavior of the resulting "partially synthetic" oil.
  • a small amount of other customary lubricating oil additives such as, for example, dispersants, detergents, corrosion inhibitors, antioxidants, wear reducers, "extreme pressure" additives, viscosity index improvers and dyes, can be added.
  • Suitable antioxidants for use at high temperatures are e.g. those of phenothiazine, phenylenediamine. Diphenylamine, but preferably of the phenylnaphthylamine type.
  • 201 g of trimethylolpropane are heated with 342 g of ⁇ -caprolactone in the presence of 1 g of dibutyltin oxide to 170 ° C. in one hour and kept at this temperature for 4 hours.
  • a mixture of 34.1 g of caproic acid, 439.3 g of caprylic acid, 276.4 g of capric acid and 7.6 g of lauric acid and 130 ml of xylene are added.
  • 81 g of water have separated out and the acid number has dropped to 21 mg KOH / g.
  • the xylene and the excess carboxylic acids are first distilled off in a water jet vacuum at 200 ° C.
  • n 1.4591, acid number: 0.1-0.2 mg KOH / g
  • 201 g of trimethylolpropane are heated with 205.2 g of ⁇ -caprolactone in the presence of 2 g of dibutyltin oxide to 170 ° C. in 1 hour and kept at this temperature for 4 hours.
  • n 1.4717, acid number: 0, 1 mg KOH mg / g.
  • the evaporation loss is 32% for A and 34% for B; on the other hand, a commercially available high-temperature oil, also provided with 5% of the same antioxidant, namely the pentaerythritol ester of 2-hexylcapric acid becomes solid under the same conditions - with an evaporation loss of 42%.
  • the caprolactone-free comparison ester analogous to Example 2 - kinem. viscosity at 210 0 F 10.7 cSt; VI 128, pour point 24 ° C - became very viscous with an evaporation loss of 45%.
  • n 1.4501, acid number: 0.2 mg KOH / g,
  • neopentyl glycol are analogous to Example 3 with 228 g of ⁇ -caprolactone, then with a mixture of 30.4 g of caproic acid (0.26 mol), 391.7 g of caprylic acid (2.72 mol), 246.5 g of capric acid (1 , 43 mol) and 6.8 g of lauric acid (0.03 mol) up to a final acid number of about 22 mg KOH / g.
  • n 1.4522, acid number: 0.1 mg K OH / g,
  • the following table shows the particularly high viscosity indices as well as the other important lubrication data.
  • Example 3 The oil mentioned in Example 3 was added in various amounts by weight to a paraffin-based, dewaxed and devolatilized solvent raffinate with a viscosity of 38 cSt (50 ° C.).
  • the V.I. of the solvent refinate was 105, the pour point was -23 ° C.
  • Table 2 explains the changes in the oil properties after the addition of increasing amounts of the ester oil according to the invention.
  • Example 4 The oil mentioned in Example 4 was mixed into a solvent raffinate of viscosity class 4.5 ° E / 50 ° C. The change in the oil properties can be seen from Table 3.
  • the Noack evaporation loss of the pure ester according to Example 4 is 5.4%.
  • a mixed ester of trimethyladipic acid with aliphatic C 8 -C 10 alcohols, which is used as an admixture component for mineral oils has the following evaporation loss values (according to Noack):

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EP79103593A 1978-10-05 1979-09-24 Huiles d'esters modifiées par des lactones et compositions lubrifiantes les contenant Expired EP0009746B1 (fr)

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DE2843473 1978-10-05
DE19782843473 DE2843473A1 (de) 1978-10-05 1978-10-05 Lactonmodifizierte esteroele

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3842703A1 (de) * 1988-12-19 1990-06-21 Henkel Kgaa Verwendung ausgewaehlter esteroele in bohrspuelungen insbesondere zur off-shore-erschliessung von erdoel- bzw. erdgasvorkommen (ii)
EP0374671A1 (fr) * 1988-12-19 1990-06-27 Henkel Kommanditgesellschaft auf Aktien Utilisation d'huiles d'esters sélectionnées, dans les fluides de forage, en particulier pour l'exploitation off-shore du pétrole ou du gaz
EP0382071A1 (fr) * 1989-02-09 1990-08-16 Henkel Kommanditgesellschaft auf Aktien Méthylester d'acide monocarboxylique dans des fluides de forage du type émulsion inverse
EP0386638A1 (fr) * 1989-03-08 1990-09-12 Henkel Kommanditgesellschaft auf Aktien Utilisation d'huiles d'esters sélectionnées, d'acides carboxyliques inférieurs dans des fluides de forage
EP0386636A1 (fr) * 1989-03-08 1990-09-12 Henkel Kommanditgesellschaft auf Aktien Ester d'acides carboxyliques à chaîne moyenne, comme composants de la phase huile d'émulsion de forage inverses
EP0398113A1 (fr) * 1989-05-16 1990-11-22 Henkel Kommanditgesellschaft auf Aktien Utilisation d'huiles d'esters sélectionnées dans de fluides de forage à base d'eau du type émulsion huile dans l'eau, et fluides de forage à qualités écologiques améliorées
US5232910A (en) * 1988-12-19 1993-08-03 Henkel Kommanditgesellschaft Auf Aktien Use of selected ester oils in drilling fluids and muds
USRE36066E (en) * 1988-12-19 1999-01-26 Henkel Kgaa Use of selected ester oils in drilling fluids and muds
US5892027A (en) * 1995-03-07 1999-04-06 Henkel Kommanditgesellschaft Auf Aktien Process for the production of neutralized polysaccharide-based polycarboxylates

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JPS62187799A (ja) * 1985-12-23 1987-08-17 ザ・ダウ・ケミカル・カンパニ− 潤滑剤組成物
US4751012A (en) * 1985-12-23 1988-06-14 The Dow Chemical Company Lubricants for reciprocating air compressors
US5032320A (en) * 1986-10-07 1991-07-16 Exxon Chemical Patents Inc. Lactone modified mono- or dicarboxylic acid based adduct dispersant compositions
US4954276A (en) * 1986-10-07 1990-09-04 Exxon Chemical Patents Inc. Lactone modified adducts or reactants and oleaginous compositions containing same
US4963275A (en) * 1986-10-07 1990-10-16 Exxon Chemical Patents Inc. Dispersant additives derived from lactone modified amido-amine adducts
US4866142A (en) * 1986-10-07 1989-09-12 Exxon Chemical Patents Inc. Lactone modified polymeric amines useful as oil soluble dispersant additives
US4866140A (en) * 1986-10-07 1989-09-12 Exxon Chemical Patents Inc. Lactone modified adducts or reactants and oleaginous compositions containing same
US4866141A (en) * 1986-10-07 1989-09-12 Exxon Chemical Patents Inc. Lactone modified, esterfied or aminated additives useful in oleaginous compositions and compositions containing same
US4866139A (en) * 1986-10-07 1989-09-12 Exxon Chemical Patents Inc. Lactone modified, esterified dispersant additives useful in oleaginous compositions
US4936866A (en) * 1986-10-07 1990-06-26 Exxon Chemical Patents Inc. Lactone modified polymeric amines useful as oil soluble dispersant additives
US4866135A (en) * 1986-10-07 1989-09-12 Exxon Chemical Patents Inc. Heterocyclic amine terminated, lactone modified, aminated viscosity modifiers of improved dispersancy
US4954277A (en) * 1986-10-07 1990-09-04 Exxon Chemical Patents Inc. Lactone modified, esterified or aminated additives useful in oleaginous compositions and compositions containing same
US4906394A (en) * 1986-10-07 1990-03-06 Exxon Chemical Patents Inc. Lactone modified mono-or dicarboxylic acid based adduct dispersant compositions
US4913830A (en) * 1987-07-24 1990-04-03 Exxon Chemical Patents Inc. Lactone-modified, mannich base dispersant additives useful in oleaginous compositions
US4828742A (en) * 1987-07-24 1989-05-09 Exxon Chemical Patents, Inc. Lactone-modified, mannich base dispersant additives useful in oleaginous compositions
US4971711A (en) * 1987-07-24 1990-11-20 Exxon Chemical Patents, Inc. Lactone-modified, mannich base dispersant additives useful in oleaginous compositions
US4820432A (en) * 1987-07-24 1989-04-11 Exxon Chemical Patents Inc. Lactone-modified, Mannich base dispersant additives useful in oleaginous compositions
US4943382A (en) * 1988-04-06 1990-07-24 Exxon Chemical Patents Inc. Lactone modified dispersant additives useful in oleaginous compositions
US4933098A (en) * 1988-04-06 1990-06-12 Exxon Chemical Patents Inc. Lactone modified viscosity modifiers useful in oleaginous compositions
DE3812235A1 (de) * 1988-04-13 1989-10-26 Draegerwerk Ag Atemanalysesystem
US4851144A (en) * 1989-01-10 1989-07-25 The Dow Chemical Company Lubricants for refrigeration compressors
WO2018110142A1 (fr) * 2016-12-13 2018-06-21 花王株式会社 Huile de base lubrifiante et composition lubrifiante comprenant ladite huile de base lubrifiante
JP7216563B2 (ja) * 2019-02-12 2023-02-01 花王株式会社 グリース基油、および該グリース基油を含有するグリース組成物
EP3926026B1 (fr) * 2020-06-16 2022-08-24 Infineum International Limited Compositions d'huile

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BE758557A (fr) * 1969-11-06 1971-04-16 Degussa Procede pour la preparation de polyesterpolyols a partir de lactones
US4130532A (en) * 1974-08-21 1978-12-19 Ciba-Geigy Ag Polyester plasticizers
GB1455390A (en) * 1974-08-22 1976-11-10 Ciba Geigy Ag Polyesters self-cooling wheel

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Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3842703A1 (de) * 1988-12-19 1990-06-21 Henkel Kgaa Verwendung ausgewaehlter esteroele in bohrspuelungen insbesondere zur off-shore-erschliessung von erdoel- bzw. erdgasvorkommen (ii)
EP0374671A1 (fr) * 1988-12-19 1990-06-27 Henkel Kommanditgesellschaft auf Aktien Utilisation d'huiles d'esters sélectionnées, dans les fluides de forage, en particulier pour l'exploitation off-shore du pétrole ou du gaz
WO1990006981A1 (fr) * 1988-12-19 1990-06-28 Henkel Kommanditgesellschaft Auf Aktien Utilisation d'huiles-esters selectionnees dans des lavages de sondage, en particulier pour la reconnaissance en mer de gisements de petrole ou de gaz naturel (ii)
USRE36066E (en) * 1988-12-19 1999-01-26 Henkel Kgaa Use of selected ester oils in drilling fluids and muds
US5232910A (en) * 1988-12-19 1993-08-03 Henkel Kommanditgesellschaft Auf Aktien Use of selected ester oils in drilling fluids and muds
EP0382071A1 (fr) * 1989-02-09 1990-08-16 Henkel Kommanditgesellschaft auf Aktien Méthylester d'acide monocarboxylique dans des fluides de forage du type émulsion inverse
WO1990009416A1 (fr) * 1989-02-09 1990-08-23 Henkel Kommanditgesellschaft Auf Aktien Methylesters d'acide monocarboxylique dans des boues de forage a emulsion inverse
DE3907391A1 (de) * 1989-03-08 1990-09-13 Henkel Kgaa Verwendung ausgewaehlter esteroele niederer carbonsaeuren in bohrspuelungen
DE3907392A1 (de) * 1989-03-08 1990-09-13 Henkel Kgaa Ester von carbonsaeuren mittlerer kettenlaenge als bestnadteil der oelphase in invert-bohrspuelschlaemmen
WO1990010681A1 (fr) * 1989-03-08 1990-09-20 Henkel Kommanditgesellschaft Auf Aktien Boues de forage inverses
WO1990010682A1 (fr) * 1989-03-08 1990-09-20 Henkel Kommanditgesellschaft Auf Aktien Utilisation d'huile-esters selectionnees d'acides carboxyliques a faible nombre d'atomes de carbone dans les fluides de forage
TR24748A (tr) * 1989-03-08 1992-03-01 Henkel Kgaa Sondaj sivilarinda,duesuek karbonik asitlerin secilmis ester yaglarinin kullanil
EP0386636A1 (fr) * 1989-03-08 1990-09-12 Henkel Kommanditgesellschaft auf Aktien Ester d'acides carboxyliques à chaîne moyenne, comme composants de la phase huile d'émulsion de forage inverses
EP0386638A1 (fr) * 1989-03-08 1990-09-12 Henkel Kommanditgesellschaft auf Aktien Utilisation d'huiles d'esters sélectionnées, d'acides carboxyliques inférieurs dans des fluides de forage
EP0398113A1 (fr) * 1989-05-16 1990-11-22 Henkel Kommanditgesellschaft auf Aktien Utilisation d'huiles d'esters sélectionnées dans de fluides de forage à base d'eau du type émulsion huile dans l'eau, et fluides de forage à qualités écologiques améliorées
WO1990014402A1 (fr) * 1989-05-16 1990-11-29 Henkel Kommanditgesellschaft Auf Aktien Utilisation d'huiles-esters selectionnees dans des fluides de forage de puits du type emulsion huile dans eau, et fluides de forage de puits moins nuisibles pour l'environnement ainsi obtenus
US5892027A (en) * 1995-03-07 1999-04-06 Henkel Kommanditgesellschaft Auf Aktien Process for the production of neutralized polysaccharide-based polycarboxylates

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JPS5558297A (en) 1980-04-30
DE2843473A1 (de) 1980-04-17
DE2961014D1 (en) 1981-12-24
US4362635A (en) 1982-12-07

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