Classifications

• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • 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
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages
  • C07F7/0803—Compounds with Si-C or Si-Si linkages
  • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
  • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
  • C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
• • 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
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/283—Esters of polyhydroxy compounds
• • 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
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/286—Esters of polymerised unsaturated acids
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
• • 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
  • 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
• • 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
  • 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
• • 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
  • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
  • C10M2227/04—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes
• • 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

• Jetturbine bearings are lubricated by pumping a lubricant to .the bearings from a reservoir in a closed. system-
• the design of more, powerful jet turbines has led to an increase in' the lubricant reservoir temperature and to greater difficulty. in maintaining lubricant stability under the more severe conditions.
• a lubricant which will'operate satisfactorily at a reservoir-terniv v United States atent perature of 250 F. will sludge badly, build up viscosity, develop high acidity and corrode metals at a reservoir temperature of 400 F.
• Carboxylic acidesteraf such as esters' of polyols with alkanoic acidsare useful as lubricants and esters of poly-v ols, such astriinethylolpropane, trimethylolethane and pentaerythritol," which have at least two methylol groups bonded to a quaternary carbon atom are particularly useful for good oxidative. and. thermal stability. However, even these compounds are not" stable under oxidative conditions in a system ,where the reservoir temperature is 'of the order of 400,F. and the local temperature at the bearings may be as high as600 to 700 F.
• the objects of this invention are achieved by provid-
• the polyol esters are esterificationproducts of single alkanoic acids, or mixtures of alkanoic, acids, with a polyol having atleast two, and preferably three, methylol groups one. quaternary carbon atom.
• the polyols which may be used are trimethylolpropane, trimethylolethane, neopentyl glycol, pentaerythritol, 2butyl-2-ethyl- 1,3-propanedio'l and 2,2,4-trimethyl-1,3-pentanediol.
• the alkanoic acids used to make the polyol esters have average chains of at least 5 carbon atoms and preferably from 5 to 8 carbon atoms.
• the individual acids, where mixtures are used may range in chain length from 2 12 carbon atoms. Normal acids are preferred, althoug branched alkanoic acids may also be used, particular those with no more than two carbon atoms in side chain
• the polyol esters are prepared by the esterification t the polyol in the'presence of a slight excess of alkano acid, either in the presence or in-the absence of an acid catalyst. For optimum heat stability, it is preferred carry out the reaction in the absence of a catalyst.
• a catalyst is used, it is generally used in an amount b tween about 0.05 and about 1.0 percent, based on tl weight of the reactants.
• the preferred catalysts are 1 toluene sulfonic acid, benzene sulfonic acid, zinc salt lead salts, and related materials.
• the 'esterification temperature is preferably betwee about 180 and about 240 C. and the reaction peric may suitably range from about 6 to about 18 hour Water isremov'ed by volatilization, preferably in ti presence of an azeotroping agent, such as a liquid hydrt carbon. v
• the diaromatic secondary amines include diaryl amine aryl-alkaryl amines and dialkaryl. amines, with the arj groups preferably having no more than 5 benzene ring and the alkyl substituents, when present, having no mo: than 24 carbon atoms.
• specific diaromat secondary amines which may be used are phenyl a nap] thylamine, p,p' dioctyldiphenylamine and phenyl B napl thylamine.
• the diaromatic secondary amine is suitably used i amounts between about 0.25 and about 3% by weigh based on the polyol ester and most preferably in amoun
• This compound may be prepared from N-ethyl diphen; amine by first reacting one mol of the latter with tw moles of butyl lithium (at C. with a nitrogen purg to sweep out the butane by-product) to produce 2,2 dilithium-N-ethyl diphenylamine and then reacting th last named compound (at 180-220 C.) with an eqtr molar proportion of diphenyl dichlorosilane to produc the desired compound.
• Another method of preparation involves the reactio. of N-ethyl phenothiazine with diphenylsilane in equimola proportions to produce the desired compound with hydrc gen sulfide as a by-product.
• phenosilazine derivatives which may be use include phenodiphenyl silazine, N-methyl-phenodipheny silazine, N-isopropyl-phenodiphenyl silazine, N-ethyl phenoditolyl silazine and N-ethyl-phenodinaphthyl sila zine, bis-N-ethyl phenosilazine, and his compounds 0 the other derivatives mentioned above.
• the phenosilazine derivative is suitably used in amount between about 0.25 and about 3% by weight, based 0: the pol'yolesterand most preferably in amounts betweei about 0.5 and about 2% by weight.
• a high temperature lubricant comprising a major proportion of a normally liquid'alkanoic acid ester of a lenosilazine' derivative generallyfbeing dissolved-at a pound having a phenosilazine ring. having its nitrogen valence satisfied by a member of the groupconsisting of polyol having two to four methylol groups on a quaternary carbon atom.
• saidalkanoic acid having an average of at least 5 carbon atonsandfthe individual acids of which contain 2 to 12- carbon atoms, said ester being stabilized against high temperature oxidati ve degradation by a minor proportion of a diaro'matic secondary amine selected from the group consisting-of diaryl amines, aryl alkaryl amines and di alkaryl ar'ninesand aininor proportion of acomhydrogen and lower alkyl radicals and its silicon valences bonded to aromatic rings.
• a diaro'matic secondary amine selected from the group consisting-of diaryl amines, aryl alkaryl amines and di alkaryl ar'ninesand aininor proportion of acomhydrogen and lower alkyl radicals and its silicon valences bonded to aromatic rings.
• a high temperature lubricant comprising a major proportion of a normallyiliquidalkanoic acid ester of a .5.h'ours with the-maximum temperature in the-reaction ui'drising to 242 C.
• e naphtha was flashed off.
• the mixture-was-then dispolyol having three methylol groups on a quaternary carbon atom.
• said alkanoic acid having an average of at least 5 carbon atoms and the individual acids of which contain led at an'absolu'te pressure of Hg and the fr'ac- Pl'l coming'ofi at a vapor temperature of 255-281 C. lS- collected.
• the collected material was giveriian alkale wash and a water wash and then The finishedvv nie'thylolpropane triheptanoate had .a specific gravity 0/20) of 0.963, an acid number (mg, KOH/g.) of 0.04, hydroxyl content of 0.20 weight-percent and a water mainof 0.0] weight percent,
• ester being stabilized against high temperature oxidative degradation by a minor prolportion of a diaromatic secondary amine selected from the group consisting of diarylj amines, aryl alkaryl amines and di-alkaryl amines and a minor proportion of "a com pound having a phenosilazine ring having its nitrogen valence satisfied by a member of the group consisting of *hydrogen and lower alkyl radicals and its silicon valences bondedto aromatic rings.
• a diaromatic secondary amine selected from the group consisting of diarylj amines, aryl alkaryl amines and di-alkaryl amines and a minor proportion of "a com pound having a phenosilazine ring having its nitrogen valence satisfied by a member of the group consisting of *hydrogen and lower alkyl radicals and its silicon valences bondedto aromatic rings.
• a high temperature-lubricant comprising a major proportion of an alkanoic acid ester of trimethylolpropane, said alkanoic acid having an average of from 5 to 8 carbon atoms, said ester beingstabiliz'ed against high temperature oxidative degradation by a minor proportion of a diaromatic secondary amine selected from the group consisting of diaryl amines, aryl alkaryl amines and dialkaryl amines and a minor proportion of a compound having a phenosilazine ring having its nitrogen valence sat isfied by a member of the group consisting of hydrogen and lower alkyl radicals and its silicon valences bonded to aromatic rings.
• a high temperature lubricant comprising a major Q proportion of trimethylolpropane triheptanoate, said trimethylolpropane triheptanoate being stabilized against high temperature oxidative degradation by a minor proportion of .a diaromatic secondary amine selected from the group consistinggof diary-l amines, aryl alkaryl amines and di-alkaryl-amin'esand a minor proportion of a compound having a phenosilazine ring having its nitrogen v lence satisfiedibya member of the group consisting of.
• said alkanoic acid having an average of from 5 to 8 c bon atoms, said ester being stabilized against high te perature oxidative degradation by from 0.25 to 3 wei percent of phenyl ot-naphthylamine and from 0.25 tc weight percent of N-ethyl-phenodiphenyl silazine.
• a high temperature lubricant comprising a ma; proportion of trimethylolpropane triheptanoate, said 1 methylolpropane triheptanoate being stabilized agaii high temperature oxidative degradation by from abc 0.5 to about 2 weight percent of phenyl e-naphthylami and from about 0.5 to about 2 weight percent of N-eth pheno'diphenyl silazine.
• An anti-oxidant composition consisting essential of a diaromatic secondary amine selected from the grow consistingod diaryl amines, aryl alkaryl amines and alkaryl amines and a compound having a phenosilazi ring having its nitrogen valence satisfied by a member the group consisting of hydrogen and lower alkyl radica and it's' silicon valences bonded to aromatic rings, sa components being present in a weight ratio of 0.25
• a high. temperature lubricant comprising a' majoreonsisting of diaryl amines, aryl alkaryl amines and c proportion ofa normally liquid alkanoic acid ester ottri- I methylolpropan'e, said alkan'oic'acidhaving an average of contain 2 to 12 carbon atoms, said ester being stabilized i at least 5 carbon atoms and the individual acids of which? against high temperature oxidative degradation by a; minor proportion of a diarom'atic secondary amine selected I from the groupconsisting of diaryl amines, aryl alkaryl amines and di-alkaryl amines and a minor proportion of an N-alkylphenodiphenyl silazine.
• a high temperature lubricant comprising a major proportion of a normally liquid alkanoic acid ester of a
• polyol having two tofour' methylol groups on a quaternary against high temperature oxidativefdegradation by a minor proportion of a diaromatic secondary amine selected from the group consistingof diaryl amines, aryl alkaryl amines and di-alkar'yl' amines and a minor'proportion of N-ethylphenodiphenyl sila'z'ine.
• a diaromatic secondary amine selected from the group consistingof diaryl amines, aryl alkaryl amines and di-alkar'yl' amines and a minor'proportion of N-ethylphenodiphenyl sila'z'ine.
• An anti-oxidant composition consisting essential of a diaromatic secondary amine selected from the grot alkaryl-amines and a phenosilazine compound having tl structure wherein the nitrogen valence is satisfied by a member the group consisting of hydrogen and lower alkyl radica and the silicon valences are bonded to aromatic ring 3 said components being present in a weight ratio of 0.25:
• a high temperature lubricant comprising a major.
• alkanoic acid having an average of from 5 to 8 carbon atoms, saidester being stabilized against high temperature oxidative degradation by a minor proportion of phenyl a-naphthylamine and a minor proportion of a 4 15.
• An anti-oxidant composition consisting essential] of phenyl a-naphthylamine and a compound having 'phenosilazine ring having its nitrogen valence satisfie .by a member of the group consisting of hydrogen an lower alkyl radicals and its silicon valences bonded t aromatic-rings, said components being present in a weigl ratio of 0.25:3 to 3:025.
• An anti-oxidant composition consisting essential] of a diaromatic secondary amine and N-ethyl-phenod lubricants consisting essentially of phenyl a-naphthylamin compound havinga phenosilazine ring having its nitrogen valence satisfied by a member of the group'consisting of hydrogen and lower alkyl radicals and its silicon valences bonded to aromatic rings.
• a high temperature lubricant comprising a major proportion of an alkanoic acid ester of a polyol having two to four methylol groups on a quaternary carbon atom, said alkanoic acid having an average of from 5 to 8 carbon atoms, said ester being stabilized against high temperature oxidative degradation by a minor proportion of phenyl phenyl s'ilazine in a weight ratio of 0.25:3 to 3:025.
• a high temperature lubricant comprising a-major proportion of an alkanoic acid ester of trimethylolpropane

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Lubricants (AREA)

Priority Applications (4)

Applications Claiming Priority (1)

Publications (1)

Family

ID=25198463

Family Applications (1)

Country Status (3)

Cited By (8)

Citations (1)

• 1959
  • 1959-04-23 US US808325A patent/US3036005A/en not_active Expired - Lifetime
• 1960
  • 1960-04-08 DE DEC21162A patent/DE1282825B/de active Pending
  • 1960-04-13 GB GB13173/60A patent/GB948633A/en not_active Expired

Patent Citations (1)

Also Published As

Similar Documents