US3585137A - Synthetic ester lubricating oil composition - Google Patents

Synthetic ester lubricating oil composition Download PDF

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US3585137A
US3585137A US836613A US3585137DA US3585137A US 3585137 A US3585137 A US 3585137A US 836613 A US836613 A US 836613A US 3585137D A US3585137D A US 3585137DA US 3585137 A US3585137 A US 3585137A
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alkyl
oil
esters
ester
acid
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David S Bosniack
Stephen J Metro
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ExxonMobil Technology and Engineering Co
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Exxon Research and Engineering Co
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    • 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
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    • C10M2207/02—Hydroxy compounds
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    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines

Definitions

  • R and R ar each hydrogen, C C alkyl, phenyl, phenalkyl or cycloalkyl, R and R are each hydrogen, C C alkyl, (l -C acyl or phenyl, and R is hydrogen, C C alkyl or halo C -C alkyl.
  • the nuclear amino radical is ortho to the amide group.
  • An arylamine may be also employed, as an antioxidant, in conjunction with the anthranilamide-type compound.
  • An arylthiazine may be used in conjunction with the antioxidant.
  • additives such as phosphate esters or phosphite esters, dimer acids (dilinoleic acid) and the like are also incorporated into the ester lubricating oil for the purpose of improving its extreme pressure, antiwear and/ or load carrying properties. If desired, still further additives may be incorporated for the purpose of reducing acidity or minimizing acidity increases during usage of the oil.
  • Turbine engines are customarily employed in aircraft today. They are, however, subjected to extreme temperatures, and excessive corrosion difliculties are encountered because of the bearings and seals employed in such engines. Alloyed bearings are customarily used in such engines and the seals which are employed to retain the oil in the engine are also subjected to extremes of temperatures, which conditions necessitate the employment of highly specialized synthetic ester oils. Heretofore these oils have been improved by the use of minor amounts, i.e. of the order of 0.01 up to as high as 5.0 wt. percent of various special purpose additives, in an effort to overcome some of the deficiencies of the synthetic ester oils. The severity of operating conditions far exceeds those encountered in internal combustion automotive engines.
  • the synthetic neutral saturated carboxylic acid ester lubricants have employed phenothiazine or the nuclearly substituted C C alkyl derivatives thereof as an antioxidant. See, U.S. Pat. 3,218,256, column 2, as well as British Pat. 824,114, which latter mentioned patent also shows the use of benzotriazole in such capacity with or without the use of phenothiazine. Additionally, amine antioxidants as shown in column 3 of U.S. Pat. 3,247,111 have been employed in conjunction with the phenothiazine and benzotriazoles for the purpose of inhibiting the undue rapid oxidation of such synthetic ester oils. Phenolic antixodiants have been employed as well.
  • the load carrying additives which have been employed are generally the phosphate esters and phosphite esters; see, for example, U.S. Pats. 2,971,912, column 6; 3,215,720, column 1; and 3,247,111, column 4.
  • dibutyl posphite and tricresyl phosphate have been widely used for the purpose of imparting antiwear or load carrying characteristics to the synthetic ester oils although any of the specific materials mentioned in the last three stated U.S. patents are also applicable conventionally for imparting load carrying properties to such oils.
  • 3,247,111 most often are N-phenyl alpha naphthylamine, N-phenyl beta naphthylamine or p,p-di-isooctyl diphenylamine, although any of the aromatic amines mentioned therein (lines 36-48) may be used in the instant novel oil compositions.
  • the synthetic neutralized saturated carboxylic acid ester lubricating oils which serve as the base oil and to which one or more of the aforementioned additives are added may be of several kinds. Numerous patents disclose these types of ester oils as being conventionally produced and used as shown by the following patents: 1,993,736; 2,249,768; 2,766,273; 2,015,088; 2,723,286; 2,743,234; 2,575,196; 3,218,256 and 3,360,465.
  • ester base oils As examples of the specific types of oils to which the present invention relates, the following ester base oils are described; the triester and tetraester lubricating oils, the complex ester oils and the diester oils all of which are conventional articles of commerce.
  • Such oils have heretofore all been used at one time or another and are still used in turbine engines that power aircraft. These engines are of the turbo jet, turbo prop, turbo fan and supersonic jet transport types. Because these engines and drive mechanisms for powering aircraft are all operated under extremely wide temperature ranges, the use of synthetic ester oils is presently almost an absolute necessity.
  • esters as referred to in the above patents, can be described as being formed in the following manner.
  • the triester and tetraester types are formed by reacting tri and tetra polyols such as trimethylol propane, pentaerythritol, trimethylol ethane, and higher trimethylol alkanes, and so forth, with C C e.g. C C normal or branched chain monocarboxylic acid or mixtures of two or more of such types of acids.
  • n-butanoic acid valeric acid, caproic acid, heptanoic acid, caprylic acid, pivalic acid, 2-ethyl hexanoic acid, pelargonic acid, lauric acid and the like.
  • the hexaesters of dipentaerythritol are also useful alone or admixed with the aforementioned tetraesters of monopentaerythritol.
  • Complex or polyester oils are also conventionally used. These are formed by esterifying polyols such as the glycols, the neopolyols previously mentioned, and the straight chain alkane diols with such dicarboxylic acids as succinic, glutaric, adipic, 2,2,4-trimethyl adipic acid, pimelic, suberic, azelaic, sebacic, brassylic acids, and dibasic dimer acids of oleic and/or linoleic acids.
  • the diols or polyethoxylated diols of C C alkylene groups or mixtures thereof are also employed in preparing polyesters from the dibasic acids.
  • the complex esters and their methods of preparation are conventional and are disclosed in representative US. patents such as 2,575,195 and 2,743,234, columns 36, inclusive.
  • diesters are conventionally formed from monohydric alcohols and dibasic acids. There are numerous references in the literature to their formation. These diesters are formed from the same dibasic acids used in connection with the formation of the complex esters hereinbefore described.
  • the alcohols are such alcohols as the 0x0 alcohols or 0x0 alcohol mixtures such as C C oxo alcohols, or from 2-ethyl hexyl alcohols, n-octyl alcohol, nonyl alcohol,
  • the synthetic ester oils or blends thereof generally have physical properties and specifications as follows: a viscosity index of at least 100, a pour or freezing point not exceeding 40 F., a boiling or decomposition temperature of at least 600 F., a Cleveland Open Cup Flash 'Point of at least 400 F., and a kinematic viscosity of less than 10 centistokes at 210 F.
  • the supersonic turbine engine oils have a more exacting specification and requirement.
  • a viscosity index of at least 100 a pour or freezing point not exceeding 65 F., a boiling or decomposition temperature of at least 600 F., a Cleveland Open Cup Flash Point of at least 450 F., and a kinematic viscosity of less than 5.5 to 6.0 centistokes at 210 F.
  • the novel additive incorporated into the synthetic ester oils in accordance with the presently discovered advance in the art is applicable to the more generally used synthetic aviation ester oils of less exacting specification as well as to the more exacting requirements of the supersonic aviation turbine ester oils.
  • the acidity of the ester oil is increased with continued use even though conventional nitrogen-containing additives (aromatic amino compounds) have been used as antioxidants therein.
  • aromatic amino compounds aromatic amino compounds
  • the use of the aminobenzamide-type compounds not only reduces the acidity and viscosity increase during oil usage but additionally dramatically reduces corrosion of copper and magnesium as well as that of other metals present in the turbine engines.
  • R and R are each hydrogen, C -C alkyl, phenyl, phenalkyl or cycloalkyl, R and R are each hydrogen, C -C alkyl, C -C acyl, or phenyl, and R is hydrogen, C -C alkyl or halo C -C alkyl.
  • typical alkyl radicals are methyl, ethyl, isopropyl, n-proply, butyl, hexyl, octyl, decyl, or dodecyl, of either straight chain or branched chain configuration;
  • typical phenalkyl radicals are benzyl, phenethyl, phenpropyl, etc.;
  • typical cycloalkyl radicals are cyclohexyl and cyclopentyl;
  • typical acyl radicals are acetyl, propionyl, butyryl, lauroyl, caproyl, capryl, caprylyl, etc.; and halo alkyl may be fiuoro or chloro mono or di-substituted methyl, ethyl, etc., i.e.
  • Orthoaminobenzamide anthranilamide
  • metaaminobenzamide may be employed.
  • Other useful compounds are:
  • the synthetic ester oils will contain between about 0.01 and 5.0 wt. percent, preferably between about 0.05 and about 0.2 wt. percent. Such small amounts do not necessitate a high degree of oil solubility of the anthranilamide-type component.
  • the solubility of anthranilamide, per se, is sufficiently high in ester oils that it is unnecessary to substitute onto either the amino or amido nitrogen, an alkyl or cycloalkyl radical for the purpose of improving the oil solubility of the anthranilamide.
  • Anthranilamide, or its simple hydrocarbon substituted or chlorhydrocarbon substituted derivatives find great utility when these are used in association with the usual aromatic amino hydrocarbon antioxidants heretofore employed.
  • these compounds are also of quite high effectiveness in passivating or inhibiting metals such as copper and/or magnesium when used in association with mono or di, or mixed mono and dialkyl phosphate or phosphite esters or the primary amine salts of dibasic or monobasic chloralkyl-phosphoric acid as described in U.S. Pat. 2,858,332.
  • One useful antiwear load bearing phosphate ester is a mixture of mono and dimethyl phosphate esters neutralized with a branched chain mixed primary C -C alkyl amine.
  • Other similar types of acidic phosphate or phosphite esters neutralized with primary or secondary long chain alkyl amines are also equally eificacious.
  • a mixture of C -C mono and di'alkyl hydrogen phosphates partially or completely neutralized with Primene 81-R (a commercial mixture of C -C alkyl primary amine) is also suitable.
  • the conventional materials previously employed such as phenothiazine, the benzotriazoles, quinizarin and its analogues, and the primary and secondary aromatic amino antioxidants may also be used in association with the anthranilamides or their nitrogen substituted hydrocarbon derivatives.
  • the amount employed of the conventional additives are those which have here tofore been employed. These amounts range between about 0.01 and about 5.0 wt. percent. -It has, however, been discovered that it is unnecessary to employ benzotriazole, heretofore used as a specific copper corrosion inhibitor, when one employs the aminobenzamide or its derivatives as a metal passivator. Benzotriazole, while effectively minimizing metal corrosion, markedly increases magnesium corrosion and increases total acidity buildup.
  • Anthranilamide may be prepared by a number of processes but the one which is generally employed involves the reaction of anthranilic acid with chloro carbonic esters of the lower aliphatic alcohols to form isatoic anhydride which is then reacted with ammonia or with a suitable primary or secondary amine to produce anthranilamide or the amino nitrogen substituted alkyl derivatives thereof.
  • the amino nitrogen is substituted as heretofore set forth instead of using anthranilic acid
  • the corresponding N-alkyl 0r N-cycloalkyl derivatives of anthranilic acid are used.
  • test data have been obtained using standard tests for determining the suitability of the aviation ester lubricants for their intended use.
  • One of the tests which have been employed is the so-called Oxidation/ Corrosion Stability Test. This is a standardized test procedure described in Specification FTMSTD 791 Method 5308. Briefly, this test involves blowing air through the oil to be tested at a specified temperature for a specified length of time (usually 347 F. for 72 hours or 400 F. for 72 hours) in the presence of metal specimens consisting of aluminum, magnesium, steel and copper tied together to form a square with a silver specimen inserted as a diagonal between the copper and steel and the aluminum and magnesium junctions.
  • the number of hours of test and the temperatures can be varied from those above specified but if and when such is the case in connection with the following tests, expressed mention of this deviation or variation will be made.
  • the test is a severe test, the results being affected by the specific chemical nature of the ester base oil and by the nature of the additive or additives present in the oil during test.
  • the test is designed to measure the attack on the various metal specimens, the percentage of change in viscosity measured in centistokes at F. (usually this is an increase in viscosity), the total increase in acidity meas ured as total acid number (TAN) measured in milligrams of KOH per gram of oil.
  • TAN total acid number
  • the attack on the various metals is measured in milligrams per square centimeter (although in some cases a protection film or deposit forms resulting in a plus value instead of a minus value) and finally, although not always, the amount of sludge or insolubles formed in grams per 100 mls. of oil is also determined.
  • EXAMPLE 1 The following compounded synthetic aviation oil was prepared: 100 parts constituted the tetraester and the hexaester of a mixture of 90% monopentaerythritol and 10% dipentaerythritol poly esterified with mixed C -C normal alkanoic acids. Based on the 100 parts of the ester base oil, (this and all subsequent oil compositions are also based on 100 parts by weight of ester base oil) the following additives (also in parts by weight per 100 parts of base oil) were added:
  • EXAMPLE 5 Same base composition as in Example 4 but contains, in addition, 0.1 quinizarin.
  • EXAMPLE 6 35 parts monopentaerythritol ester of a mixture of C -C normal alkanoic acids
  • EXAMPLE 8 50 parts of base oil of Example 1 (without additives);
  • TAB LE Used oil Percent Corrosion, change in Total acid .8 ase oil, Add. mg./em. viscosity, number, Example amount, increase increase- Example N0. N0. Additives pts. Cu Mg cs. at 100 F. Mg-KOH/gm.
  • a lubricating oil composition comprising a major portion of a synthetic neutral saturated carboxylic acid ester lubricating oil, and an amount, sufficient to inhibit metal corrosion, of an amino-benzamide having the formula:
  • R and R are each hydrogen, C -C alkyl, phenyl, phenalkyl or cycloalkyl, R and R are each hydrogen, C -C alkyl, C -C acyl, or phenyl and R is hydrogen, C -C alkyl, or halo C -C alkyl.
  • a lubricating oil composition comprising a major portion of a synthetic neutral saturated carboxylic acid ester lubricating oil, an amount, sufiicient to inhibit oxidation, of an aromatic amine antioxidant, and an amount, sufficient to inhibit metal corrosion, of an aminobenzamide having the formula:
  • R and R are each hydrogen, C -C alkyl, phenyl, phenalkyl or cycloalkyl, R and R are each hydrogen, C -C alkyl, C C acyl, or phenyl and R is hydrogen, C -C alkyl, or halo C -C alkyl.
  • An oil composition as in claim 7 which also contains phenothiazine and the aromatic amine is p,p-dioctyl diphenylamine.
  • ester oil is the tetraester of pentaerythritol with a mixture of C -C normal alkanoic acids.
  • An oil composition as in claim 15 wherein the aryl- W. J. SHINE, Assistant Examiner thiazine is phenothiazine, the aromatic amine is p,p'-dioctyl 10 diphenylamine and the composition also contains an amine addition salt of a phosphorus ester.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US836613A 1969-06-25 1969-06-25 Synthetic ester lubricating oil composition Expired - Lifetime US3585137A (en)

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US3857791A (en) * 1972-05-25 1974-12-31 Cities Service Oil Co Lubricating oil additive and lubricating oil compositions containing same
US3984337A (en) * 1973-07-02 1976-10-05 Mobil Oil Corporation Lubricant compositions containing naphthylamino benzamide antioxidants
US4107054A (en) * 1977-06-27 1978-08-15 Continental Oil Company Lubricating oil compositions
US4204970A (en) * 1978-12-07 1980-05-27 Standard Oil Company (Indiana) Lubricant compositions containing alkylated aromatic amino acid antioxidants
EP0320281A3 (en) * 1987-12-11 1989-10-25 Exxon Research And Engineering Company Corrosion inhibitor
US5560848A (en) * 1995-05-26 1996-10-01 Exxon Research And Engineering Company Combination diphenyl amine-phenothiazine additive for improved oxidation stability in polyol ester based greases (Law236)
US5780400A (en) * 1996-10-07 1998-07-14 Dover Chemical Corp. Chlorine-free extreme pressure fluid additive
US5798321A (en) * 1995-05-23 1998-08-25 Exxon Research And Engineering Company Rust resistant turbo oils containing monobasic amino phosphates and dicarboxylic acids
US6043199A (en) * 1997-08-26 2000-03-28 Exxon Research And Engineering Co. Corrosion inhibiting additive combination for turbine oils
CN103703114A (zh) * 2011-05-31 2014-04-02 卢布里佐尔公司 具有改进tbn保持性的润滑组合物

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GB1392600A (en) * 1971-11-24 1975-04-30 Exxon Research Engineering Co Lubricating oil compositions
BE795113A (fr) * 1972-02-07 1973-05-29 Tenneco Chem Esters synthetiques lubrifiants pour compresseurs d'air a mouvement alternatif
US3979308A (en) * 1974-03-27 1976-09-07 Texaco Inc. Lubricant compositions with improved viscosity index
US3931023A (en) * 1974-07-22 1976-01-06 Fmc Corporation Triaryl phosphate ester functional fluids
US4178260A (en) * 1974-10-31 1979-12-11 Exxon Research & Engineering Co. Ester based metal working lubricants
US3986965A (en) * 1975-10-31 1976-10-19 Monsanto Company Ester base lubricating compositions having improved oxidative resistance
GB1583873A (en) * 1976-05-05 1981-02-04 Exxon Research Engineering Co Synthetic lubricating oil composition
FR2414547A1 (fr) * 1978-01-11 1979-08-10 Exxon Research Engineering Co Composition d'huile lubrifiante synthetique de type ester
US4514312A (en) * 1982-07-22 1985-04-30 Witco Chemical Corporation Lubricant compositions comprising a phosphate additive system
US4514311A (en) * 1983-05-09 1985-04-30 Texaco Inc. Wear-resistant aircraft engine lubricating oil
US4661271A (en) * 1984-08-09 1987-04-28 Mobil Oil Corporation Friction reducing, antiwear additives
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
US5789358A (en) * 1995-12-22 1998-08-04 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and thiosemicarbazide derivatives
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
EP1051463A4 (en) * 1998-01-09 2002-01-30 Exxonmobil Res & Eng Co RUST-RESISTANT OIL FOR TURBINES WITH MONOBASIC AMINOPHOSPHATES AND DI-CARBONIC ACIDS
US9969950B2 (en) * 2012-07-17 2018-05-15 Infineum International Limited Lubricating oil compositions containing sterically hindered amines as ashless TBN sourcces
EP3144534B1 (en) * 2014-05-12 2018-09-12 Panasonic Intellectual Property Management Co., Ltd. Compressor and refrigeration cycle device using the same
CN106460840B (zh) * 2014-05-12 2019-11-05 松下知识产权经营株式会社 压缩机和使用其的制冷循环装置

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US2723286A (en) * 1951-10-06 1955-11-08 Exxon Research Engineering Co Reduction of acidity in synthetic ester lubes with ethylene carbonate
US2839468A (en) * 1956-05-10 1958-06-17 California Research Corp Jet turbine lubricant composition
NL108246C (enExample) * 1956-05-14
BE586528A (enExample) * 1959-01-14
US3247111A (en) * 1963-04-08 1966-04-19 Socony Mobil Oil Co High temperature jet lubricant

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3857791A (en) * 1972-05-25 1974-12-31 Cities Service Oil Co Lubricating oil additive and lubricating oil compositions containing same
US3984337A (en) * 1973-07-02 1976-10-05 Mobil Oil Corporation Lubricant compositions containing naphthylamino benzamide antioxidants
US4107054A (en) * 1977-06-27 1978-08-15 Continental Oil Company Lubricating oil compositions
US4204970A (en) * 1978-12-07 1980-05-27 Standard Oil Company (Indiana) Lubricant compositions containing alkylated aromatic amino acid antioxidants
EP0320281A3 (en) * 1987-12-11 1989-10-25 Exxon Research And Engineering Company Corrosion inhibitor
US4877541A (en) * 1987-12-11 1989-10-31 Exxon Research And Engineering Company Corrosion inhibitor
US5798321A (en) * 1995-05-23 1998-08-25 Exxon Research And Engineering Company Rust resistant turbo oils containing monobasic amino phosphates and dicarboxylic acids
US5560848A (en) * 1995-05-26 1996-10-01 Exxon Research And Engineering Company Combination diphenyl amine-phenothiazine additive for improved oxidation stability in polyol ester based greases (Law236)
WO1999035216A1 (en) * 1996-02-09 1999-07-15 Exxon Research And Engineering Company Rust resistant turbo oils containing monobasic amino phosphates and dicarboxylic acids
US5780400A (en) * 1996-10-07 1998-07-14 Dover Chemical Corp. Chlorine-free extreme pressure fluid additive
US5939366A (en) * 1996-10-07 1999-08-17 Dover Chemical Corp. Lubrication process using chlorine-free lubricant
US6043199A (en) * 1997-08-26 2000-03-28 Exxon Research And Engineering Co. Corrosion inhibiting additive combination for turbine oils
CN103703114A (zh) * 2011-05-31 2014-04-02 卢布里佐尔公司 具有改进tbn保持性的润滑组合物
US9222051B2 (en) 2011-05-31 2015-12-29 The Lubrizol Corporation Lubricating composition with improved TBN retention
CN103703114B (zh) * 2011-05-31 2016-02-10 路博润公司 具有改进tbn保持性的润滑组合物

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US3720612A (en) 1973-03-13
GB1256999A (enExample) 1971-12-15
DE2029906A1 (de) 1971-01-07
DE2029906B2 (de) 1980-09-04

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