EP0218207B1 - Use of complex esters in synthetic lubricants, and lubricants containing them - Google Patents

Use of complex esters in synthetic lubricants, and lubricants containing them Download PDF

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Publication number
EP0218207B1
EP0218207B1 EP86113639A EP86113639A EP0218207B1 EP 0218207 B1 EP0218207 B1 EP 0218207B1 EP 86113639 A EP86113639 A EP 86113639A EP 86113639 A EP86113639 A EP 86113639A EP 0218207 B1 EP0218207 B1 EP 0218207B1
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Prior art keywords
lubricants
ester
synthetic
complex esters
acid
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German (de)
French (fr)
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EP0218207A3 (en
EP0218207A2 (en
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Richard Dr. Baur
Knut Dr. Oppenlaender
Roland Dr. Schwen
Hans-Henning Dr. Vogel
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BASF SE
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Classifications

    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/68—Esters
    • C10M129/78—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, hydroxy carboxylic acids
    • C10M129/82—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, hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no 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
    • 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
    • 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
    • C10M105/46—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 derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/68—Esters
    • C10M129/78—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, 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/11—Complex polyesters

Definitions

  • the invention relates to the use of complex esters in synthetic lubricants. It also relates to a lubricant that contains at least one complex ester.
  • the HD oils (heavy duty) - to which additives were added for their additional tasks, such as aging and corrosion protection, high-pressure resistance, and as "dirt carriers" - were followed by the multigrade oils with flat viscosity curves and suitability for summer and winter operation, for longer oil change intervals and also already reduced fuel consumption, especially in winter and short-haul operations.
  • a flat viscosity curve means a reduced temperature dependence of the lubricating oil.
  • the viscosity index (VI) is a measure of the temperature dependence.
  • Complex esters are particularly suitable as synthesis components due to their low basic and low viscosity, their low volatility and high viscosity indices.
  • US-A-4 130 494 relates to the use of amine salts of phosphate esters as additives to synthetic lubricating oil compositions. These are intended to reduce unwanted deposits in the engines, especially in turbine engines.
  • US-A-4 155 861 relates to a lubricant which comprises a mixture of a monomeric ester of a branched dicarboxylic acid and an aliphatic primary monoalcohol and a complex ester of a dicarboxylic acid and hexanediol or trimethylhexanediol.
  • the lubricant should be characterized by universal applicability.
  • FR-A-1 508 458 describes the preparation of complex esters with a phosphate ester component.
  • adipic acid, neopentyl glycol and C 6 -C 10 -monocarboxylic acids are reacted with tributyl phosphate, and a complex ester is obtained which is claimed to have increased resistance to oxidation.
  • US Pat. No. 4,064,058 describes a basic lubricant composition which is essentially a mixture of a pentaerythrol ester and a neopentyl glycol ester, the neopentyl glycol ester being obtained by reacting neopentyl glycol with a C 4 -C 12 alkanedicarboxylic acid and a C 4 -C 12 alkanol was obtained.
  • the invention has for its object to provide complex esters for use in synthetic lubricants, and corresponding lubricants, which have good temperature-viscosity behavior, expressed by a high viscosity index and a low pour point, and a low evaporation loss.
  • the dicarboxylic acid component is preferably adipic acid.
  • the invention also relates to a lubricant which contains at least one compound of the general formula 1 according to one of claims 1 or 2.
  • the lubricant is preferably in the form of a synthetic lubricating oil.
  • the complex esters of the general formula I can be used either individually or in a mixture.
  • the term mixture here means a mixture of complex esters of the general formula in which the index n and / or the index m can have all of the values mentioned.
  • the measured values n and m represent mean values.
  • the mean value of the index n can be e.g. represent any value between 1 and 3. The same applies to the index m.
  • the complex ester of the general formula 1 has the isooctyl, isodecanyl or isotridecanyl radical as the monoalcohol component.
  • the isodecanyl or isotridecanyl radical are particularly preferred.
  • the alcohols R-OH used in the esterification are commercially available isomer mixtures, such as those e.g. incurred during oxosynthesis.
  • R can, for example, have the following structures 2-ethyl-4-methylpentyl, 3,3-dimethylhexyl, 3,5-dimethylhexyl, 4,5-dimethylhexyl, 2-ethylhexyl, 3-methylheptyl, 5-methylheptyl -, 3,5,5-Trimethylheptyl-, 3,5-dimethyloctyl-, 4,7-dimethyloctyl-, 3,5,5,7-tetramethylnonyl- and their isomers.
  • lubricants for engines or motor vehicle engines, compressor oils, hydraulic fluids, insulating fluids for electrical devices, electrical contact oils, lubricating greases, chain lubricants, heat transfer fluids, vacuum pump oils, synthetic fiber lubricants, instrument oils, rust protection oils and rolling oils . All applications in lubricants that have a lubricating function are included.
  • the complex esters intended for use in accordance with the invention have a very good temperature-viscosity behavior, expressed by a high viscosity index and a low pour point, and a low evaporation loss according to Noack.
  • di-isooctyl, di-isodecyl or di-isotridecyl adipate can be transesterified with hydroxypivalic acid neopentyl glycol ester (HPN) or a direct esterification of the monoalcohol, the dicarboxylic acid and the diol can be carried out.
  • HPN hydroxypivalic acid neopentyl glycol ester
  • the dicarboxylic acid and the diol can be carried out.
  • the lubrication data are listed in the table below.
  • the lubrication data are listed in the table below.
  • the lubrication data are listed in the table below.

Description

Die Erfindung betrifft die Verwendung von Komplexestern in synthetischen Schmiermitteln. Sie betrifft auch ein Schmiermittel, welches mindestens einen Komplexester enthält.The invention relates to the use of complex esters in synthetic lubricants. It also relates to a lubricant that contains at least one complex ester.

Moderne Schmiermittel, insbesondere Leichtlauf-Motorenöle, sind nicht mehr allein durch Mineralölkomponenten herstellbar, die Zumischung von Synthesekomponenten ist erforderlich. Insbesondere bei Schmierölen für Kraftfahrzeugmotoren werden ständig steigende Anforderungen gestellt, da Drehzahlen, Arbeitsdrücke und Leistungen bei gleichzeitiger Forderung nach hoher Lebensdauer und Zuverlässigkeit im Motorenbau ständig ansteigen.Modern lubricants, especially low-friction motor oils, can no longer be produced using mineral oil components alone, the addition of synthetic components is required. In particular, lubricating oils for motor vehicle engines are subject to ever increasing demands, since speeds, working pressures and outputs are constantly increasing while at the same time demanding a long service life and reliability in engine construction.

Den HD-Ölen (Heavy Duty) - denen für ihre zusätzlichen Aufgaben, wie Alterungs- und Korrosionsschutz, Hochdruckbeständigkeit, sowie als "Schmutzträger" Additive zugesetzt wurden - folgten die Mehrbereichsöle mit flachen Viskositätskurven und einer Eignung für Sommer- und Winterbetrieb, für längere Ölwechselintervalle und auch bereits verminderten Kraftstoffverbrauch, insbesondere im Winter- und Kurzstreckenbetrieb. Eine flache Viskositätskurve bedeutet eine verminderte Temperaturabhängigkeit des Schmieröls. Ein Maß für die Temperaturabhängigkeit ist der Viskositätsindex (VI).The HD oils (heavy duty) - to which additives were added for their additional tasks, such as aging and corrosion protection, high-pressure resistance, and as "dirt carriers" - were followed by the multigrade oils with flat viscosity curves and suitability for summer and winter operation, for longer oil change intervals and also already reduced fuel consumption, especially in winter and short-haul operations. A flat viscosity curve means a reduced temperature dependence of the lubricating oil. The viscosity index (VI) is a measure of the temperature dependence.

Komplexester sind aufgrund ihrer niedrigen Grund- und Kälteviskosität, ihrer geringen Flüchtigkeit und hohen Viskositätsindices als Synthesekomponenten besonders geeignet.Complex esters are particularly suitable as synthesis components due to their low basic and low viscosity, their low volatility and high viscosity indices.

Nach dem Stand der Technik ist die Verwendung einer Vielzahl unterschiedlichster Komplexester in synthetischen Schmiermittelzusammensetzungen bekannt. So betrifft die US-A-4 130 494 die Verwendung von Aminsalzen von Phosphatestern als Additive zu synthetischen Schmierölzusammensetzungen. Diese sollen unerwünschte Ablagerungen in den Motoren, insbesondere in Turbinenmotoren, verringern.The use of a large number of very different complex esters in synthetic lubricant compositions is known from the prior art. For example, US-A-4 130 494 relates to the use of amine salts of phosphate esters as additives to synthetic lubricating oil compositions. These are intended to reduce unwanted deposits in the engines, especially in turbine engines.

Die US-A-4 155 861 betrifft ein Schmiermittel, welches eine Mischung aus einem monomeren Ester einer verzweigten Dicarbonsäure und einem aliphatischen primären Monoalkohol und einem Komplexester einer Dicarbonsäure und Hexandiol oder Trimethylhexandiol, umfaßt. Das Schmiermittel soll sich durch universelle Anwendbarkeit auszeichnen.US-A-4 155 861 relates to a lubricant which comprises a mixture of a monomeric ester of a branched dicarboxylic acid and an aliphatic primary monoalcohol and a complex ester of a dicarboxylic acid and hexanediol or trimethylhexanediol. The lubricant should be characterized by universal applicability.

In der FR-A-1 508 458 ist die Herstellung von Komplexestern mit einer Phosphatesterkomponente beschrieben. Hierbei setzt man beispielsweise Adipinsäure, Neopentylglykol und C6-C10-Monocarbonsäuren mit Tributylphosphat um und erhält so einen Komplexester, für den geltend gemacht wird, daß er eine erhöhte Oxidationsbeständigkeit aufweist.FR-A-1 508 458 describes the preparation of complex esters with a phosphate ester component. Here, for example, adipic acid, neopentyl glycol and C 6 -C 10 -monocarboxylic acids are reacted with tributyl phosphate, and a complex ester is obtained which is claimed to have increased resistance to oxidation.

In der US-A-4 064 058 ist eine Schmiermittelgrundzusammensetzung beschrieben, bei der es sich im wesentlichen um eine Abmischung aus einem Pentaerythrolester und einem Neopentylglykolester handelt, wobei der Neopentylglykolester durch Reaktion von Neopentylglykol mit einer C4-C12-Alkandicar- bonsäure und einem C4-C12-Alkanol erhalten wurde.US Pat. No. 4,064,058 describes a basic lubricant composition which is essentially a mixture of a pentaerythrol ester and a neopentyl glycol ester, the neopentyl glycol ester being obtained by reacting neopentyl glycol with a C 4 -C 12 alkanedicarboxylic acid and a C 4 -C 12 alkanol was obtained.

Der Erfindung liegt die Aufgabe zugrunde, Komplexester zur Verwendung in synthetischen Schmiermitteln, sowie entsprechende Schmiermittel zur Verfügung zu stellen, welche ein gutes Temperatur-Viskositätsverhalten, ausgedrückt durch einen hohen Viskositätsindex und einen tiefen Stockpunkt, sowie einen niedrigen Verdampfungsverlust aufweisen.The invention has for its object to provide complex esters for use in synthetic lubricants, and corresponding lubricants, which have good temperature-viscosity behavior, expressed by a high viscosity index and a low pour point, and a low evaporation loss.

Diese Aufgabe wird gelöst durch Verwendung von Komplexestem der allgemeinen Formel (1)

Figure imgb0001
worin

  • R für einen Isooctyl-, Isodecanyl- oder Isotridecanylrest steht,
  • m für 4 oder 6 steht,
  • n die Bedeutungen 1, 2 oder 3 besitzt, und
  • X den Hydroxipivalinsäureneopentylglykolrest der Formel
    Figure imgb0002
    bedeutet, einzeln oder in Mischung in synthetischen Schmiermitteln.
This object is achieved by using complex esters of the general formula (1)
Figure imgb0001
 wherein
  • R represents an isooctyl, isodecanyl or isotridecanyl radical,
  • m represents 4 or 6,
  • n has the meanings 1, 2 or 3, and
  • X is the hydroxipivalic acid neopentyl glycol residue of the formula
    Figure imgb0002
     means individually or as a mixture in synthetic lubricants.

Nach einer bevorzugten Ausführungsform steht in der allgemeinen Formel I m für 4, d.h. bei der Dicarbonsäurekomponente handelt es sich bevorzugt um Adipinsäure.According to a preferred embodiment, in the general formula I m stands for 4, i.e. the dicarboxylic acid component is preferably adipic acid.

Die Erfindung betrifft auch ein Schmiermittel, welches mindestens eine Verbindung der allgemeinen Formel 1 nach einem der Ansprüche 1 oder 2 enthält. Vorzugsweise liegt das Schmiermittel in Form eines synthetischen Schmieröls vor.The invention also relates to a lubricant which contains at least one compound of the general formula 1 according to one of claims 1 or 2. The lubricant is preferably in the form of a synthetic lubricating oil.

Die Komplexester der allgemeinen Formel I können entweder einzeln oder in Mischung eingesetzt werden. Unter dem Begriff Mischung wird hier ein Gemisch von Komplexestern der allgemeinen Formel verstanden, bei dem der Index n und/oder der Index m sämtliche genannten Werte aufweisen können. Mit anderen Worten stellen dann die gemessenen Werte n und m Mittelwerte dar. So kann der Mittelwert des Indexes n z.B. irgendeinen Wert zwischen 1 und 3 darstellen. Sinngemäßes gilt für den Index m.The complex esters of the general formula I can be used either individually or in a mixture. The term mixture here means a mixture of complex esters of the general formula in which the index n and / or the index m can have all of the values mentioned. In other words, the measured values n and m represent mean values. For example, the mean value of the index n can be e.g. represent any value between 1 and 3. The same applies to the index m.

Als Monoalkoholkomponente weist der Komplexester der allgemeinen Formel 1 den Isooctyl-, Isodecanyl- oder Isotridecanylrest auf. Besonders bevorzugt sind der Isodecanyl- bzw. Isotridecanylrest.The complex ester of the general formula 1 has the isooctyl, isodecanyl or isotridecanyl radical as the monoalcohol component. The isodecanyl or isotridecanyl radical are particularly preferred.

Die bei der Veresterung benutzten Alkohole R-OH (Isooctyl-, Isodecanyl-, Isotridecanylalkohole) sind handelsübliche Isomerengemische, wie sie z.B. bei der Oxosynthese anfallen.The alcohols R-OH used in the esterification (isooctyl, isodecanyl, isotridecanyl alcohols) are commercially available isomer mixtures, such as those e.g. incurred during oxosynthesis.

Dabei kann R beispielsweise die folgenden Strukturen 2-Ethyl-4-methylpentyl-, 3,3-Dimethylhexyl-, 3,5-Dimethylhexyl-, 4,5-Dimethylhexyl-, 2-Ethylhexyl-, 3-Methylheptyl-, 5-Methylheptyl-, 3,5,5-Trimethylheptyl-, 3,5-Dimethyloctyl-, 4,7-Dimethyloctyl-, 3,5,5,7-Tetramethylnonyl-, und deren Isomere, bedeuten.R can, for example, have the following structures 2-ethyl-4-methylpentyl, 3,3-dimethylhexyl, 3,5-dimethylhexyl, 4,5-dimethylhexyl, 2-ethylhexyl, 3-methylheptyl, 5-methylheptyl -, 3,5,5-Trimethylheptyl-, 3,5-dimethyloctyl-, 4,7-dimethyloctyl-, 3,5,5,7-tetramethylnonyl- and their isomers.

Die Verwendung der Komplexester der allgemeinen Formel I ist vorgesehen in Schmiermitteln. Hierbei kann es sich beispielsweise um Schmierstoffe (Schmieröle) für Triebwerke oder Kfz-Motoren, um Kompressorenöle, hydraulische Flüssigkeiten, Isolierflüssigkeiten für elektrische Geräte, elektrische Kontaktöle, Schmierfette, Kettenschmierstoffe, Wärmeübertragungs-Flüssigkeiten, Vakuumpumpenöle, synthetische Faserschmierstoffe, Instrumentenöle, Rostschutzöle und Walzöle handeln. Sämtliche Anwendungen in Schmiermitteln, welche eine Schmierfunktion haben, sind umfaßt.The use of the complex esters of the general formula I is intended in lubricants. These can be, for example, lubricants (lubricating oils) for engines or motor vehicle engines, compressor oils, hydraulic fluids, insulating fluids for electrical devices, electrical contact oils, lubricating greases, chain lubricants, heat transfer fluids, vacuum pump oils, synthetic fiber lubricants, instrument oils, rust protection oils and rolling oils . All applications in lubricants that have a lubricating function are included.

Die zur erfindungsgemäßen Verwendung vorgesehenen Komplexester weisen ein sehr gutes Temperatur-Viskositätsverhalten, ausgedrückt durch einen hohen Viskositätsindex und einen tiefen Stockpunkt, sowie einen niedrigen Verdampfungsverlust nach Noack auf.The complex esters intended for use in accordance with the invention have a very good temperature-viscosity behavior, expressed by a high viscosity index and a low pour point, and a low evaporation loss according to Noack.

Zur Herstellung der Komplexester kann man entweder Di-Isooctyl-, Di-Isodecyl- bzw. Di-Isotridecyl-Adipat mit Hydroxipivalinsäureneopentylglykolester (HPN) umestern oder eine Direktveresterung des Monoalkohols, der Dicarbonsäure und des Diols durchführen.To prepare the complex esters, either di-isooctyl, di-isodecyl or di-isotridecyl adipate can be transesterified with hydroxypivalic acid neopentyl glycol ester (HPN) or a direct esterification of the monoalcohol, the dicarboxylic acid and the diol can be carried out.

Die Erfindung wird durch die nachstehenden Beispiele näher erläutert.The invention is illustrated by the examples below.

Beispiel 1example 1 Umesterung von Adipinsäurediisodecylester mit HPN (Hydroxipivalinsäureneopentylglykolester) 2:1 molar (Adipinsäureester:HNP)Transesterification of adipic acid diisodecyl ester with HPN (hydroxipivalic acid neopentylglycol ester) 2: 1 molar (adipic acid ester: HNP)

853,4 g (2 Mol) Adipinsäurediisodecylester, 204,0 g (1 Mol) HPN und 0,85 g Tetrabutylorthotitanat werden gemischt und langsam auf 100°C erhitzt. Man legt Wasserstrahlvakuum an und erhitzt langsam weiter auf 250°C. Während 2 Stunden bei 250°C sammelt man 310 g Isodecanol. Nach Abkühlen und Filtration erhält man 747 g des schwach gelb gefärbten Komplexesters der folgenden Struktur:853.4 g (2 mol) of diisodecyl adipate, 204.0 g (1 mol) of HPN and 0.85 g of tetrabutyl orthotitanate are mixed and slowly heated to 100.degree. A water jet vacuum is applied and heating is continued slowly to 250 ° C. During 2 hours at 250 ° C., 310 g of isodecanol are collected. After cooling and filtration, 747 g of the pale yellow complex ester of the following structure are obtained:

Figure imgb0003
Figure imgb0003

Die schmiertechnischen Daten sind in der nachstehenden Tabelle 1 aufgeführt.The lubrication data are listed in Table 1 below.

Beispiel 2Example 2 Umesterung von Adipinsäurediisodecylester mit HPN (Hydroxipivalinsäureneopentylglykolester) 3:2 molar (Adipinsäureester:HNP)Transesterification of diisodecyl adipate with HPN (hydroxipivalic acid neopentylglycol ester) 3: 2 molar (adipic acid ester: HNP)

896,1 g (2,1 Mol) Adipinsäurediisodecylester, 285,6 g (1,4 Mol) HPN und 0,90 g Tetrabutylorthotitanat werden gemischt und langsam auf 100°C erhitzt. Man legt Wasserstrahlvakuum an und erhitzt langsam weiter auf 250°C. Während 2stündigem Erhitzen auf 250°C hat man 420 g Isodecanol gesammelt. Nach Abkühlen und Filtration erhält man 760 g des schwach gelb gefärbten Komplexesters der folgenden Struktur:896.1 g (2.1 mol) of Adipinsäurediisodecylester, 285.6 g (1.4 mol) of HPN and 0.90 g of tetrabutyl orthotitanate are mixed and heated slowly to 100 ° C. A water jet vacuum is applied and heating is continued slowly to 250 ° C. During 2 hours of heating to 250 ° C., 420 g of isodecanol have been collected. After cooling and filtration, 760 g of the slightly yellow-colored complex ester of the following structure are obtained:

Figure imgb0004
Die schmiertechnischen Daten sind der nachstehenden Tabelle aufgeführt.
Figure imgb0004
 The lubrication data are listed in the table below.

Beispiel 3Example 3 Direktveresterung von Adipinsäure, Tridecanol und HPN (Hydroxipivalinsäureneopentylglykolester) 1:1,05:0,5 molar (Adipinsäure: Alkohol:HNP)Direct esterification of adipic acid, tridecanol and HPN (hydroxipivalic acid neopentylglycol ester) 1: 1.05: 0.5 molar (adipic acid: alcohol: HNP)

292 g (2 Mol) Adipinsäure, 420,7 g (2,1 Mol) Tridecanol, 204,3 g (1 Mol) HPN und 1,46 g p-Toluolsulfonsäure werden gemischt und langsam auf 200°C erhitzt. Ab ca. 120°C beginnt die Abspaltung von Wasser. Nach 2stündigem Rühren bei 200°C legt man langsam Wasserstrahlvakuum an und rührt noch 1 Stunde nach (abgespaltene Wassermenge: 71 ml). Nach Abkühlen und Reinigen des Esters (Entfernung von Säureresten, Entfernung des Restalkohols) erhält man ca. 810 g des schwach gelb gefärbten Komplexesters der folgenden Struktur:292 g (2 mol) adipic acid, 420.7 g (2.1 mol) tridecanol, 204.3 g (1 mol) HPN and 1.46 g p-toluenesulfonic acid are mixed and slowly heated to 200 ° C. At about 120 ° C, water begins to split off. After stirring for 2 hours at 200 ° C., a water jet vacuum is slowly applied and stirring is continued for 1 hour (amount of water split off: 71 ml). After cooling and cleaning the ester (removal of acid residues, removal of the residual alcohol), about 810 g of the slightly yellow-colored complex ester of the following structure are obtained:

Figure imgb0005
Figure imgb0005

Die schmiertechnischen Daten sind in der nachstehenden Tabelle aufgeführt.The lubrication data are listed in the table below.

Beispiel 4Example 4 Direktveresterung von Adipinsäure, Tridecanol und HPN (Hydroxipivalinsäureneopentylglykolester) 1:0,9:0,6 molar (Adipinsäure:Alkohol:HNP)Direct esterification of adipic acid, tridecanol and HPN (hydroxipivalic acid neopentyl glycol ester) 1: 0.9: 0.6 molar (adipic acid: alcohol: HNP)

292 g (2 Mol) Adipinsäure, 360 g (1,8 Mol) Tridecanol, 245,1 g (1,2 Mol) HPN und 1,5 g p-Toluolsulfonsäure werden gemischt und langsam auf 200°C erhitzt. Ab ca. 1200C beginnt die Abspaltung von Wasser. Nach 2stündigem Rühren bei 200°C legt man langsam Wasserstrahlvakuum an und rührt noch 1 Stunde nach (abgespaltene Wassermenge: 70 ml). Nach Abkühlen und Reinigen des Esters (Entfernung von Säureresten, Entfernung des Restalkohols) erhält man ca. 820 g des schwach gelb gefärbten Komplexesters der folgenden Struktur:

Figure imgb0006
292 g (2 mol) adipic acid, 360 g (1.8 mol) tridecanol, 245.1 g (1.2 mol) HPN and 1.5 g p-toluenesulfonic acid are mixed and slowly heated to 200 ° C. The splitting off of water begins at approx. 1200C. After stirring for 2 hours at 200 ° C., a water jet vacuum is slowly applied and stirring is continued for 1 hour (amount of water split off: 70 ml). After cooling and cleaning the ester (removal of acid residues, removal of the residual alcohol), about 820 g of the slightly yellow-colored complex ester of the following structure are obtained:
Figure imgb0006

Die schmiertechnischen Daten sind in der nachstehenden Tabelle aufgeführt.

Figure imgb0007
The lubrication data are listed in the table below.
Figure imgb0007

Claims (4)

1. Use of complex esters of the formula (I)
Figure imgb0010
where R is isooctyl, isodecyl or isotridecyl, m is 4 or 6, n is 1, 2 or 3 and X is the neopentylglycol hydroxypivalate radical of the formula (II)
Figure imgb0011
individually or as a mixture in a synthetic lubricant.
2. Use as claimed in claim 1, wherein, in the formula I, m is 4.
3. A lubricant containing one or more compounds of the formula I as claimed in either of claims 1 and 2.
4. A lubricant as claimed in claim 3, in the form of a synthetic lubricating oil.
EP86113639A 1985-10-10 1986-10-02 Use of complex esters in synthetic lubricants, and lubricants containing them Expired - Lifetime EP0218207B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19853536197 DE3536197A1 (en) 1985-10-10 1985-10-10 USE OF COMPLEXESTERS IN SYNTHETIC LUBRICANTS AND LUBRICANTS CONTAINING THEM
DE3536197 1985-10-10

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EP0218207A2 EP0218207A2 (en) 1987-04-15
EP0218207A3 EP0218207A3 (en) 1988-01-27
EP0218207B1 true EP0218207B1 (en) 1990-01-10

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Publication number Priority date Publication date Assignee Title
JPH03217494A (en) * 1990-01-22 1991-09-25 Kao Corp Refrigerating machine oil
DE4006828A1 (en) * 1990-03-05 1991-09-12 Hoechst Ag Use of ester lubricating oils
DE69414185T2 (en) * 1993-06-30 1999-04-22 Nof Corp Synthetic lubricating oil and working fluid composition for chillers
US5391312A (en) * 1993-08-02 1995-02-21 Albemarle Corportion Lubricant additives
DE19546117A1 (en) * 1995-12-11 1997-06-12 Henkel Kgaa Non-toxic heat transfer oils
US5942475A (en) * 1996-09-06 1999-08-24 Exxon Chemical Patents Inc. Engine oil lubricants formed from complex alcohol esters
KR100690351B1 (en) 2005-07-15 2007-03-12 주식회사 엘지화학 Hydroxypivalyl hydroxypivalate ester plasticizer composition and process for preparing the same

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Publication number Priority date Publication date Assignee Title
GB768119A (en) * 1954-03-17 1957-02-13 Exxon Research Engineering Co Improvements in or relating to complex ester synthetic lubricants
NL247300A (en) * 1959-01-14
US4064058A (en) * 1972-03-01 1977-12-20 Hercules Incorporated Mixed synthetic ester grease base stock

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DE3536197A1 (en) 1987-04-16
DE3668184D1 (en) 1990-02-15
EP0218207A2 (en) 1987-04-15

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