US3029204A - Acidic partial esters as lubricating oil additives - Google Patents

Acidic partial esters as lubricating oil additives Download PDF

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US3029204A
US3029204A US812583A US81258359A US3029204A US 3029204 A US3029204 A US 3029204A US 812583 A US812583 A US 812583A US 81258359 A US81258359 A US 81258359A US 3029204 A US3029204 A US 3029204A
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acid
lubricating oil
glycol
ester
percent
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Alfred H Matuszak
Stephen J Metro
Schwarz John Samuel Paul
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ExxonMobil Technology and Engineering Co
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Exxon Research and Engineering Co
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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
    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
    • C—CHEMISTRY; METALLURGY
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/04—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing aromatic monomers, e.g. styrene
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • 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
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    • 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
    • C10M2207/302—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 derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
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    • 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
    • C10M2207/304—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 derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
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    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
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    • 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
    • C10M2209/102—Polyesters
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    • 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
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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    • 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
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
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    • 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
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10M2209/111—Complex polyesters having dicarboxylic acid centres
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    • 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
    • C10M2209/112—Complex polyesters having dihydric acid centres
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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
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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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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
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    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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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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    • C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2221/043—Polyoxyalkylene ethers with a thioether group
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    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/041—Siloxanes with specific structure containing aliphatic substituents

Definitions

  • This invention relates to lubricating oil additives for improving the load-carrying ability of a lubricant and for inhibiting corrosion of lead.
  • the invention relates to synthetic ester lubricating oil compositions containing acidic partial esters which are prepared by esterification reactions between dicarboxylic acids and glycols.
  • the loadcarrying ability of the aliphatic ester oils is not particularly high. Because of the increasing severity of the conditions prevailing in the lubrication of aviation gas-turbine systems it is highly desirable to form synthetic ester lubricating compositions which have higher load-carrying ability than is now generally available. At the same time the composition should be noncorrosive to lead in the copperlead bearings generally present in aircraft engines. It has now been found that the acidic partial esters of this invention are very effective in synthetic ester lubricating oil compositions not only for improving load-carrying ability but also for inhibiting lead corrosion by the ester oil. At the same time, these new additive materials do not unduly attack copper, magnesium, aluminum or silver which are generally also present in the engine.
  • the acidic partial esters of the invention are believed to be represented by the following formula:
  • This acidic material is prepared by simple esterification reactions between a glycol and a dicarboxylic acid using about 1.2 to 2.0, preferably 1.7 to 2.0 moles of the dicarboxylic acid per mole of the glycol.
  • the primary product is believed to have the formula: Dibasic Acid-Glycol-Dibasic Acid, i.e. x is 0.
  • minor amounts of longer chain mole cules are undoubtedly also present, i.e. where x is l or more, and the exact composition is not known with certainty.
  • the dicarboxylic acids used in preparing the acidic partial ester will include the C to C alkandioic acids, such as adipic, sebacic, azelaic and isosebacic acid.
  • the isosebacic acid is a mixture of C acids comprising about 60 to 90 weight percent of wethyl suberic acid, about to 25 weight percent of m,a-diethyl adipic acid, and about 5 to 15 weight percent of sebacic acid.
  • a typical acid will contain about 75 weight percent of a-ethyl suberic acid, about 15 weight percentof a,a'-diethyl adipic acid and about weight percent of sebacic acid.
  • the glycol which is used, may be either an alkylene ice glycol or a polyalkylene glycol, said glycol containing a total of 2 to 36, preferably 4 to 18, carbon atoms.
  • included in the invention are ethylene glycol, propylene glycol, butanediol-1,4, pentanediol-1,5; hexanediol-l,6, octylene glycol, and other straight or branched chain hydrocarbon glycols.
  • Operable polyglycols will include polyethylene glycols of the formula HO (CH CH O CH CH OH wherein n is 1 to 17, preferably 1 to 8, and polypropylene glycol of the formula l '1: 1 l a HO(CHCHO)nCH-CHOH wherein either R or R is a methyl group and the other is hydrogen, and n is l to 11, preferably 2 to 5.
  • the esterification reaction is preferably carried out in the absence of an esterification catalyst. While the reaction will take place more rapidly with a catalyst, a catalyst is not used in order to obtain. a purer reaction product and to avoid washing procedures to eliminate the catalyst. If desired a water entraining agent such as heptane or toluene may be used.
  • ester oils operable as base oils in the compositions of this invention comprise hydrocarbon chains interrupted with ester linkages.
  • the hydrocarbon chains may be further interrupted with ether or tlrioether linkages.
  • esters will include diesters, polyesters, and complex esters.
  • the diesters are prepared from dicarboxylic acids fully esterified with monohydric alcohols, or from glycols fully esterified with monocarboxylic acids.
  • the total number of carbon atoms in the diester molecule is about 20 to 36, preferably 22 to 26.
  • Preferred dicarboxylic diesters are those of the formula:
  • ROOCR'COOR wherein each R may be the same or different and represents the straight or branched chain alkyl radical of an alkanol having about 6 to 13 carbon atoms, and R is a straight or branched chain C to C divalent saturated aliphatic hydrocarbon radical.
  • diesters examples include: di-Z-ethylhexyl sebacate, di-n-nonyl adipate, di-C Oxo azelate, di-n-heptyl isosebacate, di-C 0x0 adipate, di-C Oxo adipate, di-Z-ethylhexyl adipate, di-C, 0x0 adipate, di-C 0x0 trimethyl adipate, di-C Oxo pimelate, etc.
  • Other operable diesters are those prepared from glycols and monocarboxylic acids such as dipropylene glycol dipelargonate and polyethylene glycol 200 dicaproate.
  • Diesters prepared from the 0x0 alcohols which are isomeric mixtures of branched chain aliphatic primary alcohols, are particularly desirable.
  • the Oxo alcohols have a very high degree of branching in the hydrocarbon chain, which results in diester oils having low pour points and low viscosity at low temperature.
  • These alcohols are prepared from olefins, such as polymers and copolymers of C and C monoolefins, which are reacted with carbon monoxide and hydrogen in the presence of a cobalt-containing catalyst such as a cobalt carbonyl catalyst, at temperatures of about 300 to 400 F., and under pressures of about 1000 to 3000 p.s.i. to form aldehydes.
  • the resulting aldehyde product is then hydrogenated to form the 0x0 alcohol which is then recovered from the hydrogenation product.
  • Operable polyesters are prepared by reacting polyhy- 'dric alcohols such as trimethylolpropane and pentaerythritol with monocarboxylic acids such as butyric acid, caproic acid, caprylic acid, pelargonic acid, etc. to give the corresponding trior tetraesters.
  • polyhy- 'dric alcohols such as trimethylolpropane and pentaerythritol
  • monocarboxylic acids such as butyric acid, caproic acid, caprylic acid, pelargonic acid, etc.
  • the complex esters which may be used as the base oils are formed by esterification reactions between a dicarboxylic acid, a glycol, and an alcohol and/or a monocarboxylic acid. These esters may be represented by the following formulas:
  • R and R are alkyl radicals of a monohydric alcohol (e.g. alkanols), or a monocarboxylic acid (e.g. alkanoic acids), R and R are hydrocarbon radicals of dicarboxylic acids (e.g. alkandioic acids), and R and R are divalent hydrocarbon or hydrocarbon-oxy radicals, such as CH (CH or or CH CH(CH )OCH CH(CH derived from an alkylene glycol or polyalkylene glycol.
  • Some specific materials used in preparing the above types of complex esters are as follows: alkanols having 6 to 13 carbon atoms such as n-butyl alcohol, 2-ethylbutyl alcohol, 2-ethylhexanol, n-hexyl alcohol, C Oxo alcohol and C Oxo alcohol, etc.; the corresponding fatty or monocarboxylic acids; dicarboxylic acids and glycols of the same type described as useful in the preparation of the acidic partial esters of the invention.
  • the corresponding thioglycols may be used.
  • these complex esters will have a total of 20 to 80, preferably 30 to 50, carbon atoms.
  • the lubricating compositions of the invention will comprise a major proportion of a synthetic ester lubricating oil and about 0.01 to 2.0%, preferably 0.1 to 0.5 wt. percent of the acidic partial ester additive.
  • the composition can also include other additives (e.g. 0.01 to 10.0 wt. percent) such as oxidation inhibitors such as phenothiazine, phenyl-a-naphthylamine, p-amino diphenyl amine; viscosity index improvers such as polymethacrylates, polystyrene; anti-foamants such as dimethylsilicone polymers; anti-wear agents; additional loadcarrying agents; corrosion inhibitors; etc.
  • additives e.g. 0.01 to 10.0 wt. percent
  • oxidation inhibitors such as phenothiazine, phenyl-a-naphthylamine, p-amino diphenyl amine
  • Sebacic acid-PEG 200-sebacic acid EXAMPLE II 2 moles of sebacic acid was reacted with 1 mole of hexanediol-2,5 following the procedure of Example I.
  • the diester base composition was a 50/50 volume mixture of a di-C Oxo adipate and a di-C Oxo adipate which mixture contained 1 wt. percent of phenothiazine as an oxidation inhibitor.
  • the Oxo portions of the adipates were derived from Oxo alcohols prepared from a C -C olefin feed.
  • compositions tested in a lead corrosion test which was carried out by rapidly rotating a bi-metallic strip consisting of a lead strip and a copper strip bound together in an oil sample maintained at 325 F. while air was bubbled through the sample. The weight loss of the lead strip is then determined and reported in terms of milligram weight loss per sq. inch of lead surface.
  • the compositions tested and the results obtained are summarized in the following table:
  • the above table demonstrates the remarkable effectiveness of the compositions of the invention in reducing lead corrosion caused by the ester base oils.
  • the diester base composition (Test 1) showed considerable corrosivity to lead.
  • the addition of varying amounts of the acidic partial esters of Examples I through V drastically reduced the amount of corrosion (see Tests 2 to 7).
  • Test 5 shows that .44 wt. percent of the product of Example III completely eliminated lead corrosion.
  • Tests 8 to 10 demonstrate the effectiveness of the acidic partial esters with a complex ester base oil composition.
  • Example I is repeated by reacting 3 moles of the sebacic acid with 2 moles of the Polyethylene Glycol 200.
  • ester lubricating oil is a diester having the formula ROOCR'COOR wherein R is a C to C alkyl group and R is a C to C saturated hydrocarbon radical.
  • a lubricating oil composition comprising a major amount of a carboxylic acid ester lubricating oil and dissolved therein about 0.01 to about 0.5 wt. percent of the esterification reaction produce of about 2 moles of a C to C alkandioic acid with 1 mole of a C to C glycol.

Description

United States Patent 3,029,204 ACIDIC PARTIAL ESTERS AS LUBRICATING OIL ADDITIVES Alfred H. Matuszak, Westfield, and Stephen J. Metro, Scotch Plains, N.J., and John Samuel Paul Schwarz, Dugway Proving Ground, Utah, assignors to Esso Research and Engineering Company, a corporation of Delaware No Drawing. Filed May 12, 1959, Ser. No. 812,583
9 Claims. (Cl. 252-56) This invention relates to lubricating oil additives for improving the load-carrying ability of a lubricant and for inhibiting corrosion of lead. Particularly, the invention relates to synthetic ester lubricating oil compositions containing acidic partial esters which are prepared by esterification reactions between dicarboxylic acids and glycols.
The use of various fully esterified aliphatic diesters and complex esters as synthetic lubricating oils is well known to the art and has been described in numerous patents, e.g. US. 2,723,286; 2,743,234; and 2,575,196. In general, these prior aliphatic synthetic ester lubricating oils are characterized by viscosity properties that are outstanding at both low and high temperatures, especially when compared to mineral lubricating oil. Because of these characteristics, the synthetic ester oils have become of increasing importance in the field of lubrication. And one of the most important current applications of such compounds is in the lubrication of aviation gas-turbine systems such as are used in the turbo-jet or turboprop type of aircraft. However, in general, the loadcarrying ability of the aliphatic ester oils is not particularly high. Because of the increasing severity of the conditions prevailing in the lubrication of aviation gas-turbine systems it is highly desirable to form synthetic ester lubricating compositions which have higher load-carrying ability than is now generally available. At the same time the composition should be noncorrosive to lead in the copperlead bearings generally present in aircraft engines. It has now been found that the acidic partial esters of this invention are very effective in synthetic ester lubricating oil compositions not only for improving load-carrying ability but also for inhibiting lead corrosion by the ester oil. At the same time, these new additive materials do not unduly attack copper, magnesium, aluminum or silver which are generally also present in the engine.
The acidic partial esters of the invention are believed to be represented by the following formula:
Dibasic AcidGlycol-(Dibasic Acid-Glycol),,-Dibasic Acid wherein x is a number of 0 to 4. This acidic material is prepared by simple esterification reactions between a glycol and a dicarboxylic acid using about 1.2 to 2.0, preferably 1.7 to 2.0 moles of the dicarboxylic acid per mole of the glycol. When using two moles of acid per mole of glycol, the primary product is believed to have the formula: Dibasic Acid-Glycol-Dibasic Acid, i.e. x is 0. However, minor amounts of longer chain mole cules are undoubtedly also present, i.e. where x is l or more, and the exact composition is not known with certainty.
The dicarboxylic acids used in preparing the acidic partial ester will include the C to C alkandioic acids, such as adipic, sebacic, azelaic and isosebacic acid. The isosebacic acid is a mixture of C acids comprising about 60 to 90 weight percent of wethyl suberic acid, about to 25 weight percent of m,a-diethyl adipic acid, and about 5 to 15 weight percent of sebacic acid. A typical acid will contain about 75 weight percent of a-ethyl suberic acid, about 15 weight percentof a,a'-diethyl adipic acid and about weight percent of sebacic acid.
The glycol, which is used, may be either an alkylene ice glycol or a polyalkylene glycol, said glycol containing a total of 2 to 36, preferably 4 to 18, carbon atoms. Thus, included in the invention are ethylene glycol, propylene glycol, butanediol-1,4, pentanediol-1,5; hexanediol-l,6, octylene glycol, and other straight or branched chain hydrocarbon glycols. Operable polyglycols will include polyethylene glycols of the formula HO (CH CH O CH CH OH wherein n is 1 to 17, preferably 1 to 8, and polypropylene glycol of the formula l '1: 1 l a HO(CHCHO)nCH-CHOH wherein either R or R is a methyl group and the other is hydrogen, and n is l to 11, preferably 2 to 5.
The esterification reaction is preferably carried out in the absence of an esterification catalyst. While the reaction will take place more rapidly with a catalyst, a catalyst is not used in order to obtain. a purer reaction product and to avoid washing procedures to eliminate the catalyst. If desired a water entraining agent such as heptane or toluene may be used.
The ester oils operable as base oils in the compositions of this invention comprise hydrocarbon chains interrupted with ester linkages. The hydrocarbon chains may be further interrupted with ether or tlrioether linkages. Such esters will include diesters, polyesters, and complex esters.
The diesters are prepared from dicarboxylic acids fully esterified with monohydric alcohols, or from glycols fully esterified with monocarboxylic acids. The total number of carbon atoms in the diester molecule is about 20 to 36, preferably 22 to 26. Preferred dicarboxylic diesters are those of the formula:
ROOCR'COOR wherein each R may be the same or different and represents the straight or branched chain alkyl radical of an alkanol having about 6 to 13 carbon atoms, and R is a straight or branched chain C to C divalent saturated aliphatic hydrocarbon radical. Examples of such diesters include: di-Z-ethylhexyl sebacate, di-n-nonyl adipate, di-C Oxo azelate, di-n-heptyl isosebacate, di-C 0x0 adipate, di-C Oxo adipate, di-Z-ethylhexyl adipate, di-C, 0x0 adipate, di-C 0x0 trimethyl adipate, di-C Oxo pimelate, etc. Other operable diesters are those prepared from glycols and monocarboxylic acids such as dipropylene glycol dipelargonate and polyethylene glycol 200 dicaproate. Diesters prepared from the 0x0 alcohols, which are isomeric mixtures of branched chain aliphatic primary alcohols, are particularly desirable. The Oxo alcohols have a very high degree of branching in the hydrocarbon chain, which results in diester oils having low pour points and low viscosity at low temperature. These alcohols are prepared from olefins, such as polymers and copolymers of C and C monoolefins, which are reacted with carbon monoxide and hydrogen in the presence of a cobalt-containing catalyst such as a cobalt carbonyl catalyst, at temperatures of about 300 to 400 F., and under pressures of about 1000 to 3000 p.s.i. to form aldehydes. The resulting aldehyde product is then hydrogenated to form the 0x0 alcohol which is then recovered from the hydrogenation product.
Operable polyesters are prepared by reacting polyhy- 'dric alcohols such as trimethylolpropane and pentaerythritol with monocarboxylic acids such as butyric acid, caproic acid, caprylic acid, pelargonic acid, etc. to give the corresponding trior tetraesters.
The complex esters which may be used as the base oils are formed by esterification reactions between a dicarboxylic acid, a glycol, and an alcohol and/or a monocarboxylic acid. These esters may be represented by the following formulas:
wherein R and R are alkyl radicals of a monohydric alcohol (e.g. alkanols), or a monocarboxylic acid (e.g. alkanoic acids), R and R are hydrocarbon radicals of dicarboxylic acids (e.g. alkandioic acids), and R and R are divalent hydrocarbon or hydrocarbon-oxy radicals, such as CH (CH or or CH CH(CH )OCH CH(CH derived from an alkylene glycol or polyalkylene glycol. n in the complex ester molecule, will usually range from 1 to 6 and is controlled by the relative molar ratio of the glycol or polyglycol to the dicarboxylic acid. In preparing the complex ester, there will always be some simple ester formed, i.e. n=0, but this will generally be a minor portion.
Some specific materials used in preparing the above types of complex esters are as follows: alkanols having 6 to 13 carbon atoms such as n-butyl alcohol, 2-ethylbutyl alcohol, 2-ethylhexanol, n-hexyl alcohol, C Oxo alcohol and C Oxo alcohol, etc.; the corresponding fatty or monocarboxylic acids; dicarboxylic acids and glycols of the same type described as useful in the preparation of the acidic partial esters of the invention. In addition the corresponding thioglycols may be used. In general these complex esters will have a total of 20 to 80, preferably 30 to 50, carbon atoms. These complex esters and methods for their preparation are known in the art and have been described in various patents.
The lubricating compositions of the invention will comprise a major proportion of a synthetic ester lubricating oil and about 0.01 to 2.0%, preferably 0.1 to 0.5 wt. percent of the acidic partial ester additive. The composition can also include other additives (e.g. 0.01 to 10.0 wt. percent) such as oxidation inhibitors such as phenothiazine, phenyl-a-naphthylamine, p-amino diphenyl amine; viscosity index improvers such as polymethacrylates, polystyrene; anti-foamants such as dimethylsilicone polymers; anti-wear agents; additional loadcarrying agents; corrosion inhibitors; etc.
The invention will be further understood by the following examples:
EXAMPLE I An acidic partial ester was prepared as follows:
Into a 1,000 ml. round-bottom 3-neck flask fitted with a stirrer, thermometer and a reflux condenser with a water trap was placed 808 grams (4.0 moles) of sebacic acid and 364 grams (2.0 moles) of Polyethylene Glycol 200 (PEG 200a commercial polyglycol having an average molecular weight of about 182). 60 ml. of heptane as a water entraining agent was also introduced. No esterification catalyst was employed. The mixture was then refluxed at atmospheric pressure and to a final liquid temperature of 225 C. while stirring for 2 hours. The calculated amount of water (4 moles) was collected in the trap. The resulting residue was stripped of volatiles at 200 C. under a jet of nitrogen and about 1100 grams of a white semi-solid acidic partial ester was obtained. This material may be represented by the following word formula:
Sebacic acid-PEG 200-sebacic acid EXAMPLE II 2 moles of sebacic acid was reacted with 1 mole of hexanediol-2,5 following the procedure of Example I.
EXAMPLE III 4 moles of adipic acid was reacted with 2 moles of polyethylene glycol 200 following the procedure of Example I.
EXAMPLE IV 2 moles of adipic acid was reacted with 1 mole of hexanediol-2,S following the procedure of Example I.
EXAMPLE V 2 moles of adipic acid was reacted with 1 mole of 2-ethyl-hexanediol-1,3 following the process of Example I.
The products of Examples I through V, described above, were added to a diester base oil composition and tested for lead corrosion. The diester base composition was a 50/50 volume mixture of a di-C Oxo adipate and a di-C Oxo adipate which mixture contained 1 wt. percent of phenothiazine as an oxidation inhibitor. The Oxo portions of the adipates were derived from Oxo alcohols prepared from a C -C olefin feed.
Several of the products of Examples I through V were also added to a complex ester having the general formula:
C Oxo alcohol-(adipic acid-polyethylene glycol 200) -adipic acid-C Oxo alcohol wherein x averaged about 1.7. This complex ester also contained 0.5 wt. percent of phenothiazine as antioxidant and 0.01 wt. percent of a silicone anti-foamant.
The above compositions were tested in a lead corrosion test which was carried out by rapidly rotating a bi-metallic strip consisting of a lead strip and a copper strip bound together in an oil sample maintained at 325 F. while air was bubbled through the sample. The weight loss of the lead strip is then determined and reported in terms of milligram weight loss per sq. inch of lead surface. The compositions tested and the results obtained are summarized in the following table:
Table I LEAD CORROSION TEST 1 Hr. Lead Corrosion (mg. ml) Test Composition 1 Diester 3.8 15.2 141 326 2 Diester +0.275 wt. percent sebacic acid-PEG 200-sebacic acid 0.6 1.2 1.3 3.1 3 Diester +0.5 wt. percent sebacic acid-PEG 200-sebacic acid. 0 0.2 0.2 .2 4 Dlester +0.5 wt. percent sebacic 0.2 0.4 0.8 1.0
acid-hexanediol-Z,5-sebacic acid. 5 Diester +0.44 wt. percent adtpic 0 0 0 0 acid-PEG 200-ndipic acid. 6 Diester +0.2 wt. percent adlpic 0 0 0 0.2
ncid-hexanediol-2,5-adipic acid. 7 Diester +0.22 wt. percent ad p c 0.2 0.6 1.1 1.3
acifi-Z-ethyl hexanediol-1,3-ad1p1c aci 8 Complex ester- 5 29 251 9 Complex ester +1.5 wt. percent 0 0.2 .6 .8
adipic acid-PEG 200-adipic acid. 10- Complex ester +1.5 wt. percent 0.2 1.2 2.3 3.5
sebacic acid-PE G 200-sebacic acid.
The above table demonstrates the remarkable effectiveness of the compositions of the invention in reducing lead corrosion caused by the ester base oils. Thus, the diester base composition (Test 1) showed considerable corrosivity to lead. However, the addition of varying amounts of the acidic partial esters of Examples I through V drastically reduced the amount of corrosion (see Tests 2 to 7). In fact, Test 5 shows that .44 wt. percent of the product of Example III completely eliminated lead corrosion. Tests 8 to 10 demonstrate the effectiveness of the acidic partial esters with a complex ester base oil composition.
Several of the blends of Table I were further tested for corrosiveness to copper, magnesium, iron, aluminum and silver and for changes in viscosity and acidity. These tests were carried out in accordance with MILL-7808-C specification procedure, i.e., by immersing weighed strips of the metal to be tested in a 100 cc. of the sample maintained at 347 F. for 72 hours while bubbling 0.5 liter per hour of air through the sample. The metal strip is then re-weighed to determine the weight change as mg./cm. and the change in viscosity and neutralization number of the composition is determined. The compositions tested and the results obtained are summarized in Table II which follows:
Table II OXIDATION-CORROSION STABILITY 347 F. Oxidation-Corrosion Stability Composition Corrosion, mgJcm Via/100 Neut. F., Change Percent Cu Mg Fe Al Ag Change Diestor 0. 01 0. 01 0. 01 0. 0. 01 0. 8 3. 4 Diester +0.275% sebacic acid-PEG-ZOO-sebacic 0. 05 0. 05 0. 07 0. 06 0. 07 0. 9 1. 4 Dlester +0.15% sebacic acid-PEG-200'sebacie Mid 0. 13 0. 07 0.09 0. 08 0. 11 0. 9 2. 2 Somplex llilgsttenmnin5 -gu nu di fiabbu 0.34 0.01 0.05 0.05 -0.01 1.4 10.0
om ex ser se 2010 act seb eic magi"? 0.04 0.06 02 03 0- 00 0.1 15 0 As shown by Table H, there is no significant change in corrosion of the above five metals by use of the acidic partial esters of the invention. The change shown is within the tolerance allowed for products of this sort.
Several of the compositions of Table I and Table II were next tested for load-carrying ability in the Ryder Gear Test in accordance with MIL-7808C specification procedures and in a modified SAE load-carrying test. In the modified SAE test, the Standard SAE lubricant tester was used except that a gear ratio of 3.4:1 was used in place of the conventional ratio of 14.6:1. The test was carried out by running the machine for two minutes under a 50 lb. load and then manually increasing the load 50 lbs. every ten seconds until scuffing occurred. The compositions tested and the results obtained are summarized in Table III which follows:
Table III LOAD CARRYING ABILITY As seen by the above table, the additives of the invention are also useful for imparting load-carrying ability to synthetic ester lubricating oils.
While the prior examples have shown the reaction of 2 molar proportions of a dicarboxylic acid per 1 molar proportion of a glycol, a lesser molar proportion of the dicarboxylic acid may be used. To illustrate, Example I is repeated by reacting 3 moles of the sebacic acid with 2 moles of the Polyethylene Glycol 200.
tions of a C to C alkandioic acid with one molar pro portion of a C to C glycol.
2. A lubricating oil composition according to claim 1, wherein said acid partial ester is formed by the esterification of two molar proportions of said alkandioic acid with one molar proportion of said glycol.
3. A lubricating oil composition according to claim 1, wherein said glycol is a polyalkylene glycol.
4. A lubricating oil composition according to claim 1, wherein said glycol is an alkylene glycol.
5. A lubricating oil composition according to claim 1, wherein said glycol contains 4 to 18 carbon atoms.
6. A lubricating oil composition according to claim 1, wherein said synthetic ester lubricating oil consists of a hydrocarbon chain interrupted by ester linkages.
7. A lubricating oil composition according to claim 1, wherein said ester lubricating oil is a diester having the formula ROOCR'COOR wherein R is a C to C alkyl group and R is a C to C saturated hydrocarbon radical.
8. A lubricating oil composition comprising a major amount of a carboxylic acid ester lubricating oil and dissolved therein about 0.01 to about 0.5 wt. percent of the esterification reaction produce of about 2 moles of a C to C alkandioic acid with 1 mole of a C to C glycol.
9. A lubricating oil composition according to claim 8, wherein said ester lubricating oil is a diester, said alkandioic acid is an adipic acid and said glycol is a polyethylene glycol having an average molecular weight of about 182.
References Cited in the file of this patent UNITED STATES PATENTS 2,788,326 Bondi et a1 Apr. 9, 1957 2,918,433 Buckmann Dec. 22, 1959 2,929,786 Young et al Mar. 22, 1960 2,960,469 Young Nov. 15, 1960

Claims (1)

1. A LUBRICATING OIL COMPOSITION COMPRISING A MAJOR AMOUNT OF CARBOXYLIC ACID ESTER LUBRICATING OIL AND WITHIN THE RANGE OF 0.01 TO ABOUT 2.0 WT. PERCENT, BASED ON THE WEIGHT OF SAID ESTER OIL, OF AN ACID PARTIAL ESTER DISSOLVED FICATIONS PRODUCT OF ABOUT 1.7 TO ABOTU 2.0 MOLAR PROPORTIUONS OF A C4 TO C12 ALKANDIOIC ACID WITH ONE MOLAR PROPORPORTION OF A C2 TO C36 GLYCOL.
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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3247115A (en) * 1961-10-16 1966-04-19 Texaco Inc Complex ester lubricant and composition
US3287273A (en) * 1965-09-09 1966-11-22 Exxon Research Engineering Co Lubricity additive-hydrogenated dicarboxylic acid and a glycol
US3429817A (en) * 1968-02-29 1969-02-25 Exxon Research Engineering Co Diester lubricity additives and oleophilic liquids containing the same
US3493504A (en) * 1966-06-27 1970-02-03 Emery Industries Inc Fiber lubricant
US3526596A (en) * 1968-06-05 1970-09-01 Quaker Chem Corp Lubricants for metalworking operations
US4020000A (en) * 1974-03-29 1977-04-26 American Cyanamid Company Control of corrosion and scale in circulating water systems by means of partial esters of polyfunctional organic acids
FR2338334A1 (en) * 1974-03-29 1977-08-12 American Cyanamid Co PARTIAL ESTERS OF HYDROXY-POLYCARBOXYLIC ACIDS AND THEIR USE AS AN INHIBITOR OF CORROSION AND SCALE IN CIRCULATING WATER NETWORKS
US4155861A (en) * 1971-05-05 1979-05-22 Studiengesellschaft Aktiengesellschaft Ester lubricant
US4869841A (en) * 1982-12-27 1989-09-26 Bp Chimie S.A. Process for the treatment of aqueous fluids to reduce corrosion comprising dicarboxylic aliphatic acid salt and polyol

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Publication number Priority date Publication date Assignee Title
US2788326A (en) * 1950-12-26 1957-04-09 Shell Dev Extreme pressure lubricant
US2918433A (en) * 1953-12-28 1959-12-22 Union Oil Co Extreme pressure lubricating oils
US2929786A (en) * 1956-05-18 1960-03-22 Sinclair Refining Co Synthetic lubricating oil composition
US2960469A (en) * 1956-04-19 1960-11-15 Sinclair Refining Co Load carrying lubricant

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2788326A (en) * 1950-12-26 1957-04-09 Shell Dev Extreme pressure lubricant
US2918433A (en) * 1953-12-28 1959-12-22 Union Oil Co Extreme pressure lubricating oils
US2960469A (en) * 1956-04-19 1960-11-15 Sinclair Refining Co Load carrying lubricant
US2929786A (en) * 1956-05-18 1960-03-22 Sinclair Refining Co Synthetic lubricating oil composition

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3247115A (en) * 1961-10-16 1966-04-19 Texaco Inc Complex ester lubricant and composition
US3287273A (en) * 1965-09-09 1966-11-22 Exxon Research Engineering Co Lubricity additive-hydrogenated dicarboxylic acid and a glycol
US3493504A (en) * 1966-06-27 1970-02-03 Emery Industries Inc Fiber lubricant
US3429817A (en) * 1968-02-29 1969-02-25 Exxon Research Engineering Co Diester lubricity additives and oleophilic liquids containing the same
US3526596A (en) * 1968-06-05 1970-09-01 Quaker Chem Corp Lubricants for metalworking operations
US4155861A (en) * 1971-05-05 1979-05-22 Studiengesellschaft Aktiengesellschaft Ester lubricant
US4020000A (en) * 1974-03-29 1977-04-26 American Cyanamid Company Control of corrosion and scale in circulating water systems by means of partial esters of polyfunctional organic acids
FR2338334A1 (en) * 1974-03-29 1977-08-12 American Cyanamid Co PARTIAL ESTERS OF HYDROXY-POLYCARBOXYLIC ACIDS AND THEIR USE AS AN INHIBITOR OF CORROSION AND SCALE IN CIRCULATING WATER NETWORKS
US4869841A (en) * 1982-12-27 1989-09-26 Bp Chimie S.A. Process for the treatment of aqueous fluids to reduce corrosion comprising dicarboxylic aliphatic acid salt and polyol

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