US3694382A - Ester lubricant - Google Patents

Ester lubricant Download PDF

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Publication number
US3694382A
US3694382A US148177A US3694382DA US3694382A US 3694382 A US3694382 A US 3694382A US 148177 A US148177 A US 148177A US 3694382D A US3694382D A US 3694382DA US 3694382 A US3694382 A US 3694382A
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Prior art keywords
parts
acid
ester
weight percent
acids
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US148177A
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Inventor
Joseph P Kleiman
Robert E Malec
Larry Lonsker
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Ethyl Corp
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Ethyl Corp
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    • 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
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2207/025—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with condensed rings
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    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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Definitions

  • An object of this invention is to provide synthetic ester blends useful in the lubricant field.
  • a further object is to provide blends of synthetic esters having physical properties making them ideally suited as lubricants for turbine engines.
  • Another object is to provide alubricant Patented Sept. 26, 1972 viding a synthetic ester blend of:
  • TMP Trimethylolpropane
  • DiPE dipentaerythritol
  • Small amounts of monopentaerythritol and higher condensation products of pentaerythritol can be present.
  • the acids used to esterify the trimethylolpropane consist of at least 90 weight percent of a mixture consisting essentially of hexanoic, octanoic and decanoic acids
  • the acids used to esterify the dipentaerythritol consist of at least 90 weight percent of a mixture consisting essentially of pentanoic, hexanoic, octanoic and decanoic acids.
  • the acid portion of the esters are substantially normal aliphatic monocarboxylic acids. By substantially normal is meant that the major portion of the acid mixture is of the normal or straight-chain type. Generally, over percent of the acids are normal, and prefera'bly, over percent of the aliphatic acids are normal.
  • the trimethylolpropane ester is a substantially fully esterified trimethylolpropane ester of a mixture of substantially normal aliphatic monocarboxylic acids consisting of at least 90 weight percent of a mixture consisting essentially of about 20-30 weight percent hexanoic acids, about 38-48 weight percent octanoic acids, and about 25-35 weight percent decanoic acids
  • the dipentaerythritol ester is a substantially fully esterified dipentaerythritol ester of a mixture of substantially normal aliphatic monocarboxylic acids consisting of at least 90 weight percent of a mixture consisting essentially of about 30-60 weight percent pentanoic acids, about 8-20 weight percent hexanoic acids, about 15-32 weight percent octanoic acids, and about 10-25 weight percent decanoic acids.
  • Both synthetic ester components of the blend are separately prepared by well-known methods.
  • the hindered polyol (tn'methylolpropane or dipentaerythritol) is generally mixed in proper proportions with the desired aliphatic monocarboxylic acid mixture and subjected to esterification conditions. There should be enough acid equivalents in the acid mixture to at least esterify substantially all of the hydroxyl radicals in the polyol. A small excess of the acid mixture is generally used, although a large excess is not recommended, because it must be removed after the esterification is complete or the product will have too high an acid number. Removal of large amounts of unreacted acids is not economical and also is troublesome because of emulsion formations. Generally from 1-1.25 equivalents of acid mixture are used for each hydrox'yl equivalent of the polyol.
  • esters are prepared by subjecting the polyol-acid mixture to esterification conditions.
  • esterification conditions is meant that the reaction is carried out under conditions well known in the art to cause an organic carboxylic acid and an alcohol to form an ester by eliminating a molecule of water. This is generally promoted by heating the mixture containing the organic carboxylic acid and the polyol. A temperature range of from about 75-300 C. is employed.
  • the reaction is carried out at a temperature high enough to cause the water formed to distill out, but not so high as to cause decomposition of the reactants or products. Frequently, removal of the water is facilitated by including a water-insoluble azeotroping solvent in the reaction mixture. Suitable solvents include aliphatic or aromatic hydrocarbons.
  • the aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and the like, are especially useful.
  • esterification is generally conducted at the boiling point of the mixture and the Water removed from the distillate by phase separation. The solvent is returned to the reaction mixture until esterification is complete. If higher temperatures are desired during an azeotroping solvent the reaction can be carried out under pressure suflicient to raise the boiling point of the mixture to the desired reaction temperature.
  • the esterification rate can be increased by adding an esterification catalyst to the mixture.
  • Acidic catalysts have been found to be most useful. These catalysts include sulfuric acid, phosphoric acid, p-toluene sulfonic acid, sodium bisulfate, potassium bisulfate, sulfonated polystyrene acidic ion exchange resins, and the like.
  • Other useful catalysts include esters of titanium or Zirconium such as tetraalkyl titanates or zirconates (e.g. tetraethyl titanate, tetrabutyl titanate, tetra-n-propyl zirconate, etc.). Also, metal oxides such as zinc oxide, alumina, and the like, can be used.
  • the amount of catalyst is not critical. Only enough is required to promote a reasonable esterilication rate.
  • a useful range is from 0.001 to weight percent, based on the weight of the reaction mixture.
  • a preferred catalyst concentration is from
  • the esterification is conducted until the hydroxyl number of the mixture is reduced below about 10. Following this, the ester can be subjected to various treatments to remove undesirable material. Solvents or excess aliphatic carboxylic acids can be removed by heating the ester, preferably under vacuum, to a temperature high enough to cause them to distill out. Temperatures of from 100- 250 C. at vacuums under 50 mm. of Hg, preferably under mm. of Hg, are usually sufficient. Residual acid can be removed by washing the ester with an aqueous base such as sodium hydroxide or sodium carbonate. Alternatively, the ester can be first washed with aqueous base prior to distilling out the solvent. This latter method allows the removal of residual water with the solvent.
  • Solvents or excess aliphatic carboxylic acids can be removed by heating the ester, preferably under vacuum, to a temperature high enough to cause them to distill out. Temperatures of from 100- 250 C. at vacuums under 50 mm. of Hg, preferably under mm
  • Further drying of the ester can be accomplished by treatment with any of the known drying agents such as anhydrous sodium sulfate. It is generally desirable to subject the final ester to further treatment with an adsorbent material such as activated clay, alumina or charcoal, to remove trace acids and other impurities.
  • an adsorbent material such as activated clay, alumina or charcoal
  • the aliphatic monocarboxylic acid mixtures useful in preparing the esters are mixtures of aliphatic monocarboxylic acids containing, in the case of the trimethylolpropane ester component, from 4-12 carbon atoms per acid molecule, and in the case of the dipentaerythritol ester component, from 4-10 carbon atoms per molecule.
  • the proportion of the individual acids in the mixture is adjusted so that on a mole basis the average number of carbon atoms in the acids of the mixture of acids used to make the trimethylolpropane esters is from 6-9 and the average number of carbon atoms in the acid mixture used to make the dipentaerythritol esters is from 5-9.
  • the average number of carbon atoms is readily calculated by multiplying the number of carbon atoms of each acid by the mole fraction of that acid in the mixture and adding the products.
  • an equal mole mixture of hexanoic and octanoic acids has an average of 7 carbon atoms per molecule on a mole basis.
  • the aliphatic monocarboxylic acids may be straight or branched chain.
  • typical acids used to prepare the esters include n-butyric acid, isobutyric acid, Z-methyI-n-butyric acid, B-methyI-n-butyric acid, n-pentanoic acid, Z-methyI-n-pentanoic acid, 2-ethyl-nbutyric acid, n-hexanoic acid, Z-methyl-n-hexanoic acid, Z-ethyI-n-pentanoic acid, 3 methyl n hexanoic acid, n-heptanoic acid, 2-ethyl-n-hexanoic acid, 2-methyl-nheptanoic acid, 3-methyl-n-heptanoic acid, 2,3-di-methyln-hexanoic "acid, n-octanoic acid, Z-methyI-n-octa
  • the preferred aliphatic monocarboxylic acids used in making the esters are normal or straight chain acids. Examples of these are n-butyric, n-pentanoic, n-hexanoic, n-heptanoic, n-octanoic, n-nonanoic, n-decanoic, n-undecanoic, and n-dodecanoic.
  • the acids used in making the tri methylolpropane ester are mixtures of n-hexanoic, n-octanoic and n-decanoic acids, and the acids used in making the dipentaerythritol esters are n-pentanoic, n-hexanoic, n-octanoic and n-decanoic.
  • a most preferred mixture of acids for preparing the substantially fully esterified TMP blending component is a mixture consisting of at least weight percent of a mixture consisting essentially of from 20-30 weight percent hexanoic acid, from 38-48 weight percent octanoic acid, and from 25-35 Weight percent decanoic acid.
  • a most preferred mixture of acids for preparing the substantially fully esterified DiPE blending component is a mixture consisting of at least 90 Weight percent of a mixture consisting essentially of from 30-60 weight percent pentanoic acid, from 8-20 weight percent hexanoic acid, from 15-32 weight percent octanoic acid, and from l0-25 weight percent decanoic acid. As stated above, best results are obtained when the acids are substantially all of the normal configuration.
  • the amount of the trimethylolpropane ester component and the dipentaerythritol ester component used to prepare the blend is adjusted so that from 1.5-2.5 parts by weight of trimethylolpropane ester is employed for each 0.75-2 parts of the dpentaerythritol ester.
  • Ester blends having superior physical properties are generally obtained when from about 1.9-2.2 parts by Weight of the trimethylolpropane ester are used for each 0.9-1.1 part by weight of the dipentaerythritol ester.
  • the trimethylolpropane ester component is a substantially fully esterified trimethylolpropane ester of a substantially normal aliphatic monocarboxylic acid mixture consisting of at least 90 weight percent of a mixture consisting essentially of about 20-30 Weight percent hexanoic acids, about 38-48 weight percent octanoic acids, and about 25-35 Weight percent decanoic acids
  • the dipentaerythritol ester component is a substantially fully esterified dipentaerythritol ester of a substantially normal aliphatic monocarboxylic acid mixture consisting of at least 90 weight percent of a mixture consisting essentially of about 30-60 weight percent pentanoic acids, about 8-20 Weight percent hexanoic acids, about 15-32 weight percent o t i acids, and about 10-25 weight percent decanoic acids.
  • An especially preferred class of ester lubricants of hi invention is a blend of from about 1.9-2.2 parts by weight of a substantially fully esterified trimethylolpropane ester of a substantially normal aliphatic monocarboxylic acid mixture consisting essentially of from about 24-28 weight percent hexanoic acid, about 41-45 weight percent octanoic acid, and about 29-33 weight percent decanoic acid, and from 0.9-1.1 parts by weight of a substantially fully esterified dipentaerythritol ester of a substantially normal aliphatic monocarboxylic acid mixture consisting essentially of from about 45-55 weight percent pentanoic acid, about 11-15 weight percent hexanoic acid, and about 13-18 weight percent decanoic acid.
  • Another highly preferred embodiment is a blend of (a) from about 0.9 to 1.1 parts by weight of a trimethylolpropane ester of a substantially normal aliphatic monocarboxylic acid mixture consisting of at least 90 weight pecent of a mixture consisting essentially of from 20-30 weight percent hexanoic acid, from 38-48 weight percent octanoic acid, and from 25-35 weight percent decanoic acid, and (b) from about 1.15 to 1.35 parts by weight of a dipentaerythritol ester of a substantially normal aliphatic monocarboxylic acid mixture consisting of at least 90 weight percent of a mixture consisting essentially of from 30-60 weight percent pentanoic acid, from 8-20 weight percent hexanoic acid, from 15-32 weight percent octanoic acid, and from 10-25 weight percent decanoic acid.
  • An especially preferred embodiment is a blend of (a) from about 0.9 to 1.1 parts by weight of a trimethylolpropane ester of a substantially normal aliphatic monocarboxylic acid mixture consisting essentially of about 24-28 weight percent hexanoic acid, about 41-45 weight percent octanoic acid, and about 29-33 weight percent decanoic acid, and (b) from about 1.15 to 1.35 parts by weight of a dipentaerythritol ester of a substantially normal aliphatic monocarboxylic acid mixture consisting essentially of about 45-55 weight percent pentanoic acid, about 11-15 weight percent hexanoic acid, about 18-24 weight percent octanoic acid, and about 13-18 weight percent decanoic acid.
  • the mixture was then cooled, diluted with an equal volume of petroleum ether, washed twice with 10 percent caustic and then with water until neutral. The solution was dried over anhydrous calcium sulfate and filtered.
  • the petroleum ether solvent was removed by heating the mixture to about 100 C., and the remaining volatile material was distilled out by heating the mixture to about 130 C. at a pressure of under 0.25 mm. Hg.
  • the remaining TMP ester was filtered, giving a blending stock for preparing the ester blends of this invention, Its viscosity was 4.0 cs. at 210 F. and 17.9 cs. at 100 F. Its viscosity index was 134 (ASTM D2270-64).
  • EXAMPLE 2 Preparation of DiPE ester
  • the mixture was refluxed for 72 hours, during which period water was continuously removed in the water trap. At this time, infrared analysis indicated less than 0.1 weight percent hydroxyl.
  • the mixture was then cooled, diluted with an equal volume of petroleum ether, washed twice with 10 percent caustic and then with water until neutral. It was then dried over anhydrous calcium sulfate and filtered.
  • the petroleum ether was distilled out up to a liquid temperature of about C. and the remaining volatile material removed by heating to about C. at a vacuum of 0.25 mm. Hg. Finally, the product was filtered, giving a DiPE blending stock useful for preparing the ester blends of this invention. Its viscosity was 9.1 cs. at 210 F., and 59.5 cs. at 100 F. Its viscosity index was 144.
  • EXAMPLE 3 The following example shows the preparation of a useful TMP ester blend component without employing a catalyst.
  • EXAMPLE 4 This example illustrates the preparation of a DiPE ester blend component without the use of a catalyst.
  • Example 1 To the reaction vessel of Example 1 was added 59.33 parts of dipentaerythritol, 165 parts of a substantially normal acid mixture consisting essentially of 50 weight percent pentanoic acids, 13 weight percent hexanoic acids, 21.5 weight percent octanoic acids, and 16.5 weight percent decanoic acids. While stirring, the mixture was heated rapidly to 165 C. and then, over a 2.25 hour period, raised to 233 C. while continually removing water in the water trap. The mixture was then slowly heated to 244 C., during the following 5 hour period, at which time the infrared analysis indicated the esterification was complete.
  • a substantially normal acid mixture consisting essentially of 50 weight percent pentanoic acids, 13 weight percent hexanoic acids, 21.5 weight percent octanoic acids, and 16.5 weight percent decanoic acids. While stirring, the mixture was heated rapidly to 165 C. and then, over a 2.25 hour period, raised to 233 C. while continually
  • TMP and DiPE blending components can readily be made following the above procedures by merely varying the amount and types of aliphatic monocarboxylic acids employed within the param eters already described.
  • EXAMPLE 5 In a glass-lined reaction vessel was placed 9.4 parts of trimethylolpropane, 2.15 parts of xylene and 32.9 parts of an acid mixture consisting essentially of 26 weight percent n-hexanoic acid, 43 weight percent n-octanoic acid, and 31 weight percent n-decanoic acid. The mixture was heated to reflux C.) while stirring and refluxed for 7 hours while removing water from the distillate. The temperature reached 251 C. It was then cooled and diluted with 30 parts of hexane. It was washed with 10 parts of 10 percent aqueous caustic and a second time with 5 parts of 10 percent aqueous caustic.
  • Blends useful as lubricants of this invention are prepercent n-pentanoic acid, 13 weight percent n-hexanoic pared by mixing the TMP esters and DiPE esters selected acid, 21.5 weight percent n-octanoic acid, and 15.5 weight from the foregoing tables in the proportion shown in the percent n-decanoic acid.
  • the mixture was heated to reflux 40 following table. (150 C.) while stirring and refluxed for 11 hours while TABLE ESTERS continuously removing water from the distillate. The temperature reached 245 C. It was then cooled and diluted Bland TMP ester met with 16.5 parts of hexane.
  • fi but l fi vanous and 9 shown In the other useful esters can be obtained by varying the amount 0 owmg ta e amolmt of acld used 15 based on the of each type ester within the range of from 1.5-2.5 parts use of 134 parts of TMP 1n the TMP ester table and 136 t f UPE h DPE bl of TMP ester for each 0.75 1.25 parts of DiPE ester.
  • 0 b l m e h 1 gi ta ahphatlc An unusual feature of the present blends is their exg g gggg ac1 5 5 own e ta 6 y are ceptionally high viscosity index.
  • the viscosity index of the blend is (a) n-butyric higher than that of either blend component.
  • Viscosity (b) isobutyric index is a standard industry-recognized criteria for measur- (c) n-pentanoic ing the ability of an oil to resist change in viscosity with (d) Z-methyI-n-butyric change in temperature (ASTM method D-2270-64).
  • n-hexanoic 65 a lubricant with a high viscosity index tends to (f) 2-methyl-n-pentanoic maintain a lubricating viscosity at higher temperature (g) 2,2-dimethyl-n-butyr1c and still not become too viscous at low temperature.
  • This (h) Z-ethyI-n-butyric is an especially important property of the lubricant in (i) n-heptanoic turbine use.
  • Turbines must be able to be started under (j) Z-methyi-n-hexanmc arctic conditions but must still have a lubricant that will (k) 2,2-dimethyl-n-pentanoic protect at the temperature reached under maximum out- (I) n-octanoic put.
  • the blend components have a viscosity index of from 134-144.
  • the blends have a viscosity index of 147-148, which is significantly higher than that of either blend component.
  • Oxidative Stability Tests were carried out to demonstrate the stability of the ester blends of this invention under high temperature oxidative conditions. These tests, called Oxidative Stability Tests, are carried out by first formulating the ester lubricant to contain 0.8weight percent dioctyl diphenylamine, 0.8 weight percent phenyl-a-naphthylamine, 0.04 weight percent benzotriazole, and 2.0 weight percent tricresylphosphate. Then 100 ml. samples are placed in test cells along with copper and steel coupons. They are heated to 400 F. and air is bubbled through the fluid at a rate of 5 1./hr. for 72 hours. Following this, the weight loss of the coupons is determined and also the acid number, viscosity increase, visual appearance and pentane insolubles are determined. Results obtained with the above blended ester lubricants are as follows:
  • ester blends of this invention not only possess excellent physical properties but are also highly stable under severe oxidative conditions.
  • antioxidants include antioxidants, metal passivators, extreme pressure agents, antifoam agents, and the like.
  • a useful antioxidant range is from 0.1 to 5.0 weight percent.
  • the preferred antioxidants include:
  • Typical extreme pressure agents are the esters of acids of phosphorus including triarylphosphates such as triphenylphosphate, tricresylphosphate, phenyldicresylphosphate, tritolylphosphate, and the trialkylphosphates and phosphonates such as tri-n-butylphosphate, tri-(2-ethylhexyl)phosphate, tri-methylcyclohexylphosphate, tri-butylphosphonate, tri-(B-chloroisopropyl)phosphonate, and the like.
  • triarylphosphates such as triphenylphosphate, tricresylphosphate, phenyldicresylphosphate, tritolylphosphate
  • trialkylphosphates and phosphonates such as tri-n-butylphosphate, tri-(2-ethylhexyl)phosphate, tri-methylcyclohexylphosphate, tri-butylphosphonate, tri-(B-
  • Silicones such as dimethyl silicone, diethyl silicone, and the like, are used in small amounts, from about 1 to 50 p.p.m., to inhibit foam.
  • EXAMPLE 7 In a blending vessel is placed parts of ester No. 3 from Table 4. To this is added one part of phenyl-anaphthyl amine, one part of dioctyldiphenyl amine, 0.1 part of a fatty acid salt of 1-salicylalaminoguanidine, 0.02 part of 1,4-di-hydroxy anthraquinone, 3 parts of tricresylphosphate and 5 p.p.m., based on the total, of dimethyl silicone. The mixture is stirred until homogenous and then filtered through a fine filter, resulting in an ester lubricant suitable for use in lubricating turbine bearings.
  • EXAMPLE 9 In a blending vessel place 1000 parts of ester No. 5 from Table 5, parts of phenyl-a-naphthyl amine, 10 parts of dioctyldiphenyl amine, 5 parts of benzotriazole and parts of tricresylphosphate. Stir the mixture until homogenous and filter to obtain a synthetic lubricant suitable for use in turbine engines.
  • ester blends described herein are also eminently useful in other applications.
  • they are readily thickened by fatty acid soaps such as the alkali or alkaline earth metal stearates to form synthetic ester greases. Addition of about 10-20 weight percent of lithium stearate to the hot ester followed by cooling gives a useful synthetic ester based grease.
  • plasticizers are also useful as plasticizers in a wide range of plastics. For example, adding 5-50 parts per 100 of ester to a calendering grade of polyvinyl chloride resin gives a useful flexible product.
  • They are also useful in various specialty applications which require a liquid that does not freeze and maintains good flow characteristics over a wide temperature range.
  • they can be used as damping fluids in instruments having moving parts that require damping, such as compasses.
  • Another example is their use as the liquid in bubble type levels.
  • They can also be used as fluid in hydraulic shock absorbers.
  • Useful automatic transmission fluids are readily formulated from the ester blends by addition of an antioxidant such as phenyl-p-naphthyl amine, a wear agent such as tricresylphosphate, and a small amount of a methyl silicone foam agent.
  • an antioxidant such as phenyl-p-naphthyl amine
  • a wear agent such as tricresylphosphate
  • a small amount of a methyl silicone foam agent such as phenyl-p-naphthyl amine
  • the ester can be used to lubricate internal combustion engines including both spark ignited and diesel engines. In this use they can be used as the sole base stock or they can be blended with mineral lubricating oils to obtain the desired properties at the least cost.
  • typical additives can be included such as zinc dialkyldithiophosphates, calcium sulfonates, barium salts of phosphosulfurized high molecular Weight olefins and dispersants such as high molecular weight alkenyl succinimides and succinamides of ethylenepolyamines such as tetraethylenepentamine and mixtures thereof.
  • a synthetic ester consisting essentially of a blend of:
  • said ester of trimethylolpropane is a substantially fully esterified trimethylolpropane ester of an aliphatic monocarboxylic acid mixture consisting of at least 90 weight percent of a mixture of hexanoic, octanoic and decanoic acids, and
  • said ester of dipentaerythritol is a substantially fully esterified dipentaerythritol ester of an aliphatic 12 monocarboxylic acid mixture consisting of at least weight percent of a mixture of pentanoic, hexanoic, octanoic and decanoic acids.
  • said ester of trimethylolpropane is a substantially fully esterified trimethylolpropane ester of a substantially normal aliphatic monocarboxylic acid mixture consisting of at least 90 weight percent of a mixture consisting essentially of from 20-30 weight percent hexanoic acid, from 38-48 weight percent octanoic acid, and from 25-35 weight percent decanoic acid, and
  • said ester of dipentaerythritol is a substantially fully esterified dipentaerythritol ester of a substantially normal aliphatic monocarboxylic acid mixture consisting of at least 90 weight percent of a mixture consisting essentially of from 30-60 weight percent pentanoic acid, from 8-20 weight percent hexanoic acid, from 15-32 weight percent octanoic acid, and from 10-25 weight percent decanoic acid.
  • said trimethylolpropane ester is a substantially fully esterified trimethylolpropane ester of a substantially normal aliphatic monocarboxylic acid mixture consisting essentially of about 24-28 weight percent hexanoic acid, about 41-45 weight percent 0ctanoic acid, and about 29-33 Weight percent decanoic acid, and
  • dipentaerythritol ester is a substantially fully esterified dipentaerythritol ester of a substantially normal aliphatic monocarboxylic acid mixture consisting essentially of about 45-55 weight percent pentanoic acid, about 11-15 weight percent hexanoic acid, about 18-24 weight percent octanoic acid, and about 13-18 weight percent decanoic acid.
  • dipentaerythritol ester is a substantially fully esterified dipentaerythritol ester of a substantially normal aliphatic monocarboxylic acid mixture consisting essentially of about 45-55 weight percent pentanoic acid, about 11-15 weight percent hexanoic acid, about 18-24 weight percent octanoic acid, and about 13-18 weight percent decanoic acid.
  • a formulated ester blend comprising at least 90 weight percent of a synthetic ester blend of claim 1 and (a) from about 0.01-5 weight percent of an antioxidant for synthetic ester lubricants,

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Cited By (37)

* Cited by examiner, † Cited by third party
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US4025447A (en) * 1974-05-08 1977-05-24 Snam Progetti S.P.A. Esters as components of lubricants
US4045376A (en) * 1976-04-23 1977-08-30 Texaco Inc. Synthetic turbine oils
US4061581A (en) * 1973-12-12 1977-12-06 Institut Francais Du Petrole Trimethylolpropane esters useful as base lubricants for motor oils
US4175046A (en) * 1978-09-20 1979-11-20 Mobil Oil Corporation Synthetic lubricant
US4175045A (en) * 1978-02-27 1979-11-20 Stauffer Chemical Company Compressor lubrication
US4234497A (en) * 1979-04-30 1980-11-18 Standard Lubricants, Inc. Iso-palmitate polyol ester lubricants
US4243540A (en) * 1973-07-09 1981-01-06 Snamprogetti S.P.A. Organic esters for lubricating compositions
US4263159A (en) * 1978-03-24 1981-04-21 Stauffer Chemical Company Automatic transmission fluid comprising esters derived from a particular monocarboxylic acid composition
US4317780A (en) * 1975-12-11 1982-03-02 Snamprogetti S.P.A. Organic ester for use in lubricant compositions
US4332738A (en) * 1980-11-24 1982-06-01 Exxon Research & Engineering Co. Esterification of neo acids by the use of cation exchange resins
US4780229A (en) * 1984-10-01 1988-10-25 Akzo America Inc. High temperature polyol ester/phosphate ester crankcase lubricant composition
US4879052A (en) * 1987-11-05 1989-11-07 Akzo America Inc. High temperature polyol ester/phosphate ester crankcase lubricant composition
EP0498152A1 (en) * 1991-01-17 1992-08-12 Cpi Engineering Services, Inc. Lubricant composition for fluorinated refrigerants
US5254277A (en) * 1991-12-20 1993-10-19 Akzo N.V. Corrosion inhibitor composition for formulated polyol ester fluids
WO1993024587A1 (en) * 1992-06-03 1993-12-09 Henkel Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids
EP0652280A3 (en) * 1993-10-15 1995-06-21 Oronite Japan Limited Multipurpose functional fluid for agricultural machinery or construction machinery
WO1993025628A3 (en) * 1992-06-03 1995-10-12 Henkel Corp Polyol ester heavy duty compressor lubricants
WO1993025629A3 (en) * 1992-06-03 1995-10-19 Henkel Corp Polyol ester lubricants for refrigerating compressors operating at high temperatures
WO1995029214A1 (en) * 1994-04-26 1995-11-02 Castrol Limited Lubricant composition
US5503760A (en) * 1992-05-02 1996-04-02 Henkel Kommanditgesellschaft Auf Aktien Engine base oils with improved seal compatibility
WO1996028525A1 (en) * 1995-03-14 1996-09-19 Exxon Chemical Patents Inc. Polyol ester compositions with unconverted hydroxyl groups
WO1997011140A1 (en) * 1995-09-21 1997-03-27 Exxon Chemical Patents Inc. Synthetic ester base stocks for low emission lubricants
US5750478A (en) * 1995-12-22 1998-05-12 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and sulfurized fatty acid
US5820777A (en) * 1993-03-10 1998-10-13 Henkel Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids
US5833876A (en) * 1992-06-03 1998-11-10 Henkel Corporation Polyol ester lubricants for refrigerating compressors operating at high temperatures
US5851968A (en) * 1994-05-23 1998-12-22 Henkel Corporation Increasing the electrical resistivity of ester lubricants, especially for use with hydrofluorocarbon refrigerants
US5853609A (en) * 1993-03-10 1998-12-29 Henkel Corporation Polyol ester lubricants for hermetically sealed refrigerating compressors
WO1999010455A1 (en) * 1997-08-25 1999-03-04 Hatco Corporation Poly(neopentyl polyol) ester based coolants and improved additive package
US5906769A (en) * 1992-06-03 1999-05-25 Henkel Corporation Polyol ester lubricants for refrigerating compressors operating at high temperatures
US5976399A (en) * 1992-06-03 1999-11-02 Henkel Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids
US6183662B1 (en) 1992-06-03 2001-02-06 Henkel Corporation Polyol ester lubricants, especially those compatible with mineral oils, for refrigerating compressors operating at high temperatures
EP0941426A4 (en) * 1996-12-04 2002-08-28 Henkel Corp SHOCK ABSORBER CONTAINING BIODEGRADABLE FLUID
US6551968B2 (en) 2001-01-05 2003-04-22 Hatco Corporation Biodegradable polyneopentyl polyol based synthetic ester blends and lubricants thereof
US20040209788A1 (en) * 1991-06-07 2004-10-21 Schaefer Thomas G. Synthetic lubricant base stock formed from high content branched chain acid mixtures
US20060019848A1 (en) * 2004-07-12 2006-01-26 Dexin Luo High gloss, non-feathering lip product
US7018558B2 (en) 1999-06-09 2006-03-28 Cognis Corporation Method of improving performance of refrigerant systems
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US5665683A (en) * 1987-04-10 1997-09-09 Bremer & Leguil Gmbh Lubricant and lubricant concentrate
DE3712132A1 (de) * 1987-04-10 1988-10-20 Grill Max Gmbh Schmiermittel bzw. schmiermittelkonzentrat
DE3712133A1 (de) * 1987-04-10 1988-10-20 Siwa Gmbh Schmiermittel bzw. schmiermittelkonzentrat

Cited By (55)

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Publication number Priority date Publication date Assignee Title
US4243540A (en) * 1973-07-09 1981-01-06 Snamprogetti S.P.A. Organic esters for lubricating compositions
US4061581A (en) * 1973-12-12 1977-12-06 Institut Francais Du Petrole Trimethylolpropane esters useful as base lubricants for motor oils
US4025447A (en) * 1974-05-08 1977-05-24 Snam Progetti S.P.A. Esters as components of lubricants
US4317780A (en) * 1975-12-11 1982-03-02 Snamprogetti S.P.A. Organic ester for use in lubricant compositions
US4045376A (en) * 1976-04-23 1977-08-30 Texaco Inc. Synthetic turbine oils
US4175045A (en) * 1978-02-27 1979-11-20 Stauffer Chemical Company Compressor lubrication
US4263159A (en) * 1978-03-24 1981-04-21 Stauffer Chemical Company Automatic transmission fluid comprising esters derived from a particular monocarboxylic acid composition
US4175046A (en) * 1978-09-20 1979-11-20 Mobil Oil Corporation Synthetic lubricant
US4234497A (en) * 1979-04-30 1980-11-18 Standard Lubricants, Inc. Iso-palmitate polyol ester lubricants
US4332738A (en) * 1980-11-24 1982-06-01 Exxon Research & Engineering Co. Esterification of neo acids by the use of cation exchange resins
US4780229A (en) * 1984-10-01 1988-10-25 Akzo America Inc. High temperature polyol ester/phosphate ester crankcase lubricant composition
US4879052A (en) * 1987-11-05 1989-11-07 Akzo America Inc. High temperature polyol ester/phosphate ester crankcase lubricant composition
EP0498152A1 (en) * 1991-01-17 1992-08-12 Cpi Engineering Services, Inc. Lubricant composition for fluorinated refrigerants
AU653572B2 (en) * 1991-01-17 1994-10-06 Cpi Engineering Services, Inc. Lubricant composition for fluorinated refrigerants used in compression refrigeration systems
US5486302A (en) * 1991-01-17 1996-01-23 Cpi Engineering Services, Inc. Lubricant composition for fluorinated refrigerants used in compression refrigeration systems
US5612299A (en) * 1991-01-17 1997-03-18 Cpi Engineering Services, Inc. Lubricant composition for fluorinated refrigerants used in compression refrigeration systems
US20040209788A1 (en) * 1991-06-07 2004-10-21 Schaefer Thomas G. Synthetic lubricant base stock formed from high content branched chain acid mixtures
US5254277A (en) * 1991-12-20 1993-10-19 Akzo N.V. Corrosion inhibitor composition for formulated polyol ester fluids
US5503760A (en) * 1992-05-02 1996-04-02 Henkel Kommanditgesellschaft Auf Aktien Engine base oils with improved seal compatibility
US6183662B1 (en) 1992-06-03 2001-02-06 Henkel Corporation Polyol ester lubricants, especially those compatible with mineral oils, for refrigerating compressors operating at high temperatures
US6221272B1 (en) 1992-06-03 2001-04-24 Henkel Corporation Polyol ester lubricants for hermetically sealed refrigerating compressors
WO1993025629A3 (en) * 1992-06-03 1995-10-19 Henkel Corp Polyol ester lubricants for refrigerating compressors operating at high temperatures
WO1993024587A1 (en) * 1992-06-03 1993-12-09 Henkel Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids
US5976399A (en) * 1992-06-03 1999-11-02 Henkel Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids
WO1993025628A3 (en) * 1992-06-03 1995-10-12 Henkel Corp Polyol ester heavy duty compressor lubricants
US6666985B2 (en) 1992-06-03 2003-12-23 Cognis Corporation Polyol ester lubricants for hermetically sealed refrigerating compressors
US6551524B2 (en) 1992-06-03 2003-04-22 Cognis Corporation Polyol ester lubricants, especially those compatible with mineral oils, for refrigerating compressors operating at high temperatures
US6296782B1 (en) 1992-06-03 2001-10-02 Henkel Corporation Polyol ester lubricants for refrigerator compressors operating at high temperatures
US5906769A (en) * 1992-06-03 1999-05-25 Henkel Corporation Polyol ester lubricants for refrigerating compressors operating at high temperatures
US5833876A (en) * 1992-06-03 1998-11-10 Henkel Corporation Polyol ester lubricants for refrigerating compressors operating at high temperatures
US5820777A (en) * 1993-03-10 1998-10-13 Henkel Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids
US5853609A (en) * 1993-03-10 1998-12-29 Henkel Corporation Polyol ester lubricants for hermetically sealed refrigerating compressors
EP0652280A3 (en) * 1993-10-15 1995-06-21 Oronite Japan Limited Multipurpose functional fluid for agricultural machinery or construction machinery
US5607907A (en) * 1993-10-15 1997-03-04 Oronite Japan Limited Multipurpose functional fluid for agricultural machinery or construction machinery
WO1995029214A1 (en) * 1994-04-26 1995-11-02 Castrol Limited Lubricant composition
CN1043053C (zh) * 1994-04-26 1999-04-21 卡斯特罗尔有限公司 润滑剂组合物
US5851968A (en) * 1994-05-23 1998-12-22 Henkel Corporation Increasing the electrical resistivity of ester lubricants, especially for use with hydrofluorocarbon refrigerants
US5744434A (en) * 1995-03-14 1998-04-28 Exxon Chemical Patents Inc. Polyol ester compositions with unconverted hydroxyl groups
WO1996028525A1 (en) * 1995-03-14 1996-09-19 Exxon Chemical Patents Inc. Polyol ester compositions with unconverted hydroxyl groups
EP0835922A1 (en) * 1995-03-14 1998-04-15 Exxon Chemical Patents Inc. Polyol ester compositions with unconverted hydroxyl groups
US6551523B1 (en) 1995-06-07 2003-04-22 Cognis Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids
WO1997011140A1 (en) * 1995-09-21 1997-03-27 Exxon Chemical Patents Inc. Synthetic ester base stocks for low emission lubricants
US5674822A (en) * 1995-09-21 1997-10-07 Exxon Chemical Patents Inc Synthetic ester base stocks for low emission lubricants
US5750478A (en) * 1995-12-22 1998-05-12 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and sulfurized fatty acid
EP0941426A4 (en) * 1996-12-04 2002-08-28 Henkel Corp SHOCK ABSORBER CONTAINING BIODEGRADABLE FLUID
US6444626B1 (en) 1997-08-25 2002-09-03 Hatco Corporation Poly(neopentyl polyol) ester based coolants and improved additive package
US5895778A (en) * 1997-08-25 1999-04-20 Hatco Corporation Poly(neopentyl polyol) ester based coolants and improved additive package
WO1999010455A1 (en) * 1997-08-25 1999-03-04 Hatco Corporation Poly(neopentyl polyol) ester based coolants and improved additive package
KR100580786B1 (ko) * 1997-08-25 2006-05-23 하트코 코포레이션 폴리(네오펜틸 폴리올) 에스테르와 폴리올 에스테르로 이루어진 에스테르 혼합물을 포함하는 합성 냉각제/윤활제 조성물 및 이를 사용하여 압축기를 냉각 및 윤활시키는 방법
US7018558B2 (en) 1999-06-09 2006-03-28 Cognis Corporation Method of improving performance of refrigerant systems
US6551968B2 (en) 2001-01-05 2003-04-22 Hatco Corporation Biodegradable polyneopentyl polyol based synthetic ester blends and lubricants thereof
US20060019848A1 (en) * 2004-07-12 2006-01-26 Dexin Luo High gloss, non-feathering lip product
US20110147999A1 (en) * 2004-07-12 2011-06-23 Dexin Luo High Gloss, Non-Feathering Lip Product
EP4559990A1 (en) 2023-11-21 2025-05-28 LANXESS Corporation Ester-fluorocarbon mixtures as efficient heat transfer fluids
WO2025111406A1 (en) 2023-11-21 2025-05-30 Lanxess Corporation Ester-fluorocarbon mixtures as efficient heat transfer fluids

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