US3804762A - Antioxidants - Google Patents

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Publication number
US3804762A
US3804762A US00289154A US28915472A US3804762A US 3804762 A US3804762 A US 3804762A US 00289154 A US00289154 A US 00289154A US 28915472 A US28915472 A US 28915472A US 3804762 A US3804762 A US 3804762A
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Prior art keywords
phenyl
antioxidant
percent
naphthylamine
ester
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US00289154A
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G Jervis
R Robson
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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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
    • 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
    • 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
    • C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
    • C10N2060/04—Oxidation, e.g. ozonisation

Definitions

  • antioxidant mixture suitable for an aviation turbine oil comprises (a) an alkylated N-phenyl naphthylamine having at least one alkyl substituent each containing from 3 to 14 carbon atoms, e.g. N-(tert-octyl henyD-B-naphthylamine and (b) an amino compound of the formula CH3 CH3 C IC CH3 where X is hydrogen, hydrocarbyl containing up to 20 carbon atoms, or the group 011, e.g. N,N' tetramethyl diamino diphenyl methane, the mole ratio of (a) to (b) being at least 1:1.
  • This antioxidant has good antioxidant potency together with low corrosive tendencies.
  • Preferred alkylated N-phenyl naphthylamines are monoor di-(C -C alkyl N-phenyl naphthylamines.
  • the alkyl groups need not of course be the same for the dialkyl compounds. When there is one alkyl substituent on the phenyl group it is preferably in the para position, although it can of course be in the orthoor meta-positions.
  • the total number of carbon atoms in the two alkyl groups is preferably not more than 20.
  • the preferred alkylated N-phenyl naphthyl amine is N-(tert-octyl phenyl)- 8-naphthylamine.
  • one or both of the aromatic rings of the naphthylamine part of the molecule may be alkylated, and the term fal-kylated N-phenyl naphthylamine covers both possibilities.
  • Suitable alkyl group substituents of the naphthylamine part of the molecule include those specifically mentioned above.
  • Component '(a) should contain no sulphur atoms present as a substituent or part of a substituent group.
  • the preferred Component (b) is N,N' tetra methyl diamino diphenyl methane, i.e. when X is hydrogen. It could however be for example 1,1-bis(N,N dimethyl amino phenyl) heptane, N,N tetra methyl diamino triphenyl methane or N,N',N hexa methyl triamino triphenyl methane.
  • X is hydrocarbyl, it preferably contains from 2 to 12 carbon atoms.
  • the mole ratio of (a) to (b) must be at least 1:1, and is preferably between 1:1 and 13:1, especially between 1:1 and 10:1.
  • a particularly preferred mole ratio is between 2:1 and 4:1 e.g. about 23:1.
  • the antioxidant mixture of the invention is suitable for use in a lubricating oil, especially an aviation turbine oil.
  • a lubricating oil especially an aviation turbine oil.
  • it should be added in minor proportion, preferably 0.001 to 10.0% by weight, e.g. 0.1 to 5.0% by weight, based on the weight of lubricating oil.
  • the lubricating oil to which the antioxidant mixture may be added can be any mineral, animal, fish, vegetable or synthetic oil, for example, petroleum oil fractions ranging from spindle oil to SAE 30, 40 or 50 lubricating oil grades, castor oil, animal or fish oils or oxidized mineral oil, e.g. palm oil, lard oil, tallow oil, arachis oil or sperm oil.
  • the preferred lubricating oil is a synthetic ester and suitable diesters include diesters of the general formula ROOCR'COOR and RCOOR'OOCR where R represents a C to C alkyl group, while R represents a C to C saturated aliphatic hydrocarbon group or an ether-interrupted saturated aliphatic hydrocarbon group.
  • suitable diesters include diesters of the general formula ROOCR'COOR and RCOOR'OOCR where R represents a C to C alkyl group, while R represents a C to C saturated aliphatic hydrocarbon group or an ether-interrupted saturated aliphatic hydrocarbon group.
  • the above types of esters may be prepared from alcohols and dicarboxylic acids or glycols and monocarboxylic acids.
  • ester lubricant are the polyesters which are prepared by reacting polyhydric alcohols e.g. those having 2 to 12 hydroxyl groups per molecule and 2 to 40 carbon atoms per molecule, such as trimethylolpropane, pentaerythritol' and di-pentaerythritol with monoand/or di-carboxylic acids such as butyric acid, caproic acid, caprylic acid and pelargonic acid, or adipic, sebacic or azelaic acids.
  • polyhydric alcohols e.g. those having 2 to 12 hydroxyl groups per molecule and 2 to 40 carbon atoms per molecule, such as trimethylolpropane, pentaerythritol' and di-pentaerythritol with monoand/or di-carboxylic acids such as butyric acid, caproic acid, caprylic acid and pelargonic acid, or adipic, sebacic or azelaic acids
  • the complex esters which may be used as 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 formulae:
  • R represents alkyl radicals derived from a monohydric alcohol
  • R represents hydrocarbon radicals derived from a dicarboxylic acid, e.g. alkanedioic acids
  • R represents divalent hydrocarbon or hydrocarbon-oxy radicals such as -CH (CH or or CH CH(CH )(OCH CH(CH derived from an alkylene glycol or polyalkyleneglycol, while R represents the alkyl group derived from a monocarboxylic acid.
  • n in the complex ester molecule which is an integer will usually range from 1 to 6 depending upon the product viscosity desired which is controlled by the relative molar ratio of the glycol or polyglycol to the dicarboxylic acid.
  • n the product viscosity desired which is controlled by the relative molar ratio of the glycol or polyglycol to the dicarboxylic acid.
  • n the complex ester
  • these complex esters will have a total of between 15 and 80, e.g. between 20 and 65 carbon atoms per molecule.
  • esters of polyhydric alcohols having the formulae where R is a CH OH group or an alkyl group, e.g. an alkyl group containing 1 to 6 carbon atoms.
  • suitable esters of this type are the neopentyl polyol esters of trimethylol ethane, trimethylol propane, trimethylol butane and of pentaerythritol or di-pentaerythritol.
  • the preferred acids used to esterify trimethylol proprone are the C to C monocarboxylic acids. Particularly preferred at the C -C esters, e.g. C (caprylic) and C (pelargonic) acid esters. Mixtures of these C -C acids may be used. When such an acid mixture is used, it is preferred that the mixture average between C and C Although more difiicult to form, it is even more preferred that one methylol group be esterified with a neoheptanoic acid, e.g. 2,2-dimethylpentanoic acid, and the remaining methylol groups esterified with non-hindered acids, e.g. pelargonic acid. This particular ester is substantially as thermally stable as the completely hindered ester but has superior volatility and low temperature characteristics.
  • the preferred acids used to esterify pentaerythritol are the C C monocarboxylic acids with the more preferred esters being those of C to C acids, e.g. n-valeric, isovaleric, 2-ethyl butyric, caproic, n-heptylic, n-octanoic or 2-ethyl hexoic acids or a mixture of C to C acids.
  • Blends of diesters with minor proportions of one or more thickening agents may also be used as lubricants.
  • Formulations suitable for gas turbine lubrication include from 65 to 90 vol. percent of one or more diesters of azelaic or sebacic acid and a C -C branched chain alcohol, particularly of 2-ethyl hexanol, or 0x0 alcohols consisting predominantly of C C 01- C alcohols, or of mixtures of such alcohols, and 35 to 10% of polywherein R R and R are hydrogen or (I -C alkyl groups and wherein not more than two such groups is hydrogen, and n is an integer greater than 1.
  • Particularly useful compounds are poly-oxypropylene glycol monoethers and the corresponding diethe-rs.
  • the thermal stability of such diester/polyoxyalkylene glycol ethers may be improved if a small proportion of a complex ester derived from three or more carboxylic acids or alcohols, at least two of which are difunctional acids or alcohols is incorporated.
  • Such complex esters may 'be glycolor dicarboxylic acid centered, the molecule being terminated with a mono-hydroxy or monocarboxylic acid compound.
  • a particularly preferred complex ester of this type is derived from polyethylene glycol of molecular weight 200, 2 molecules of sebacic or azelaic acid, and 2 molecules of a (J -C branched chain aliphatic monohydric alcohol, particularly 2-ethyl hexanol.
  • additives which may be incorporated in the lubricating oil include corrosion inhibitors, e.g. sebacic acid, a metal deactivator such as quinizarin, a foam inhibitor, e.g. a silicone polymer such as dimethyi silicone, or an antiwear additive, e.g. neutral alkyl phosphates such as tricresyl phosphate, neutral alkyl aryl phosphates, or neutral phosphonates.
  • corrosion inhibitors e.g. sebacic acid
  • a metal deactivator such as quinizarin
  • a foam inhibitor e.g. a silicone polymer such as dimethyi silicone
  • an antiwear additive e.g. neutral alkyl phosphates such as tricresyl phosphate, neutral alkyl aryl phosphates, or neutral phosphonates.
  • EXAMPLE 1 Various antioxidant mixtures were prepared by blending together N-(tert-octyl henyD-fi-naphthylamine (abbreviated C -PBNA) and N,N'-tetra methyl di-amino diphenyl methane (abbreviated TMDDPM).
  • C -PBNA N-(tert-octyl henyD-fi-naphthylamine
  • TMDDPM N,N'-tetra methyl di-amino diphenyl methane
  • the base oil was a mixture of complete esters obtained by esterification of 90% pentaerythritol and 10% dipentaerythritol with a mixture of (C -C fatty acids.
  • EXAMPLE 2 An antioxidant mixture of TMDDPM and C -PBNA was prepared and added to a synthetic ester mixture consisting of complete esters prepared from mixed C to C fatty acids and a mixture of 80 wt. percent pentaerythritol, 10 wt. percent dipentaerythritol and 10 wt. percent trimethylol propane.
  • TEDDPM N,N'-tetraethy1 diamino diphenyl methane
  • Benzene insolubles percent A kv. 210 F., percent Percent vola- Anttoxidant tility A ten 1.0 wt. percent 'IMD PM, 3.0 wt. percent C PBNA 1.0 wt. per cent TEDDPM, 3.0 wt. parcent Ca- EXAMPLE 3
  • An antioxidant mixture of TMDDPM and N-(n-heptyl phenyl)- 9 naphthylamine (abbreviated Cq-PBNA) was prepared and added to a synthetic ester mixture consisting of complete esters prepared from mixed C -C fatty acids and a mixture of 90 wt. percent pentaerythritol and 10% di-pentaerythritol.
  • An antioxidant mixture comprising (a) an alkylated N-phenyl naphthylamine having from one to two alkyl substituents each containing from 3 to 14 carbon atoms, and (b) an amino compound of the formula where X is hydrogen, hydrocarbyl containing up to 20 carbon atoms, or the group the mole ratio of (a) to (b) being within the range of 1:1 to 13:1.
  • component (a) has two alkyl groups and the total number of carbon atoms in the two alkyl groups is not more than 20.
  • component (a) is N-(tert-octyl phenyl)- 8-naphthylamine.
  • component (b) is N,N' tetramethyl diamino diphenyl methane.
  • a lubricating oil composition comprising a major proportion by weight of a lubricating oil and a minor proportion by weight of the antioxidant mixture according to claim 1.
  • component (a) is N- (heptyl henyD-fl-naphthylamine.
  • component (b) is N,N,N" hexamethyl triamino triphenyl methane.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
US00289154A 1971-10-06 1972-09-14 Antioxidants Expired - Lifetime US3804762A (en)

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE28805E (en) * 1971-11-17 1976-05-11 Mobil Oil Corporation Lubricants containing amine antioxidants
US4073701A (en) * 1976-10-15 1978-02-14 Bethlehem Steel Corporation Acid electrotinning bath
US4146490A (en) * 1977-12-02 1979-03-27 Fmc Corporation Turbine lubricant
US5489711A (en) * 1994-12-20 1996-02-06 The B. F. Goodrich Company Synthetic lubricant antioxidant from monosubstituted diphenylamines
US5516443A (en) * 1991-08-22 1996-05-14 Exxon Chemical Patents Inc. Compounds and fuel compositions
US6426324B1 (en) 1993-12-15 2002-07-30 Noveon Ip Holdings Corp. Lubricant composition

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2584884A (en) * 1983-09-16 1985-03-21 Bankamerica Corp. Lubricant for use with alcoholic fuels
IN163879B (enExample) * 1984-09-17 1988-12-03 Bank Of America
GB2294696A (en) * 1994-11-04 1996-05-08 Exxon Research Engineering Co Marine lubricant composition

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE28805E (en) * 1971-11-17 1976-05-11 Mobil Oil Corporation Lubricants containing amine antioxidants
US4073701A (en) * 1976-10-15 1978-02-14 Bethlehem Steel Corporation Acid electrotinning bath
US4146490A (en) * 1977-12-02 1979-03-27 Fmc Corporation Turbine lubricant
US5516443A (en) * 1991-08-22 1996-05-14 Exxon Chemical Patents Inc. Compounds and fuel compositions
US6426324B1 (en) 1993-12-15 2002-07-30 Noveon Ip Holdings Corp. Lubricant composition
US5489711A (en) * 1994-12-20 1996-02-06 The B. F. Goodrich Company Synthetic lubricant antioxidant from monosubstituted diphenylamines

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JPS48103472A (enExample) 1973-12-25
DE2249031A1 (de) 1973-04-12
FR2156095A1 (enExample) 1973-05-25
FR2156095B1 (enExample) 1976-10-29

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