US3901815A - Synthetic aircraft turbine oil - Google Patents
Synthetic aircraft turbine oil Download PDFInfo
- Publication number
- US3901815A US3901815A US476625A US47662574A US3901815A US 3901815 A US3901815 A US 3901815A US 476625 A US476625 A US 476625A US 47662574 A US47662574 A US 47662574A US 3901815 A US3901815 A US 3901815A
- Authority
- US
- United States
- Prior art keywords
- thiouracil
- lubricating oil
- oil composition
- percent
- composition according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000010723 turbine oil Substances 0.000 title description 3
- -1 aliphatic ester Chemical class 0.000 claims abstract description 46
- 239000000203 mixture Substances 0.000 claims abstract description 46
- 229950000329 thiouracil Drugs 0.000 claims abstract description 29
- 239000002199 base oil Substances 0.000 claims abstract description 11
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims abstract 2
- 239000010687 lubricating oil Substances 0.000 claims description 31
- ZEQIWKHCJWRNTH-UHFFFAOYSA-N 1h-pyrimidine-2,4-dithione Chemical compound S=C1C=CNC(=S)N1 ZEQIWKHCJWRNTH-UHFFFAOYSA-N 0.000 claims description 11
- ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical compound O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 claims description 9
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical class CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 claims description 2
- HWGBHCRJGXAGEU-UHFFFAOYSA-N Methylthiouracil Chemical compound CC1=CC(=O)NC(=S)N1 HWGBHCRJGXAGEU-UHFFFAOYSA-N 0.000 claims description 2
- 229960002545 methylthiouracil Drugs 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 abstract description 8
- 125000000217 alkyl group Chemical group 0.000 abstract description 7
- 229910019142 PO4 Inorganic materials 0.000 abstract description 6
- 239000010452 phosphate Substances 0.000 abstract description 6
- 239000010689 synthetic lubricating oil Substances 0.000 abstract description 5
- 230000001050 lubricating effect Effects 0.000 abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 24
- 150000002148 esters Chemical class 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- 239000007789 gas Substances 0.000 description 6
- 239000000314 lubricant Substances 0.000 description 6
- 239000012530 fluid Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 229940036565 thiouracil antithyroid preparations Drugs 0.000 description 4
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- UQJDVLPHTXQTRP-UHFFFAOYSA-N 2,2-bis(heptanoyloxymethyl)butyl heptanoate Chemical compound CCCCCCC(=O)OCC(CC)(COC(=O)CCCCCC)COC(=O)CCCCCC UQJDVLPHTXQTRP-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical class CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 1
- LIAWCKFOFPPVGF-UHFFFAOYSA-N 2-ethyladamantane Chemical compound C1C(C2)CC3CC1C(CC)C2C3 LIAWCKFOFPPVGF-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- UUNBFTCKFYBASS-UHFFFAOYSA-N C(CCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCC Chemical compound C(CCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCC UUNBFTCKFYBASS-UHFFFAOYSA-N 0.000 description 1
- RVKKRRXSXPNVLU-UHFFFAOYSA-N C(CCCCCCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCCCCCC Chemical compound C(CCCCCCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCCCCCC RVKKRRXSXPNVLU-UHFFFAOYSA-N 0.000 description 1
- 101100361281 Caenorhabditis elegans rpm-1 gene Proteins 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- GTVWRXDRKAHEAD-UHFFFAOYSA-N Tris(2-ethylhexyl) phosphate Chemical compound CCCCC(CC)COP(=O)(OCC(CC)CCCC)OCC(CC)CCCC GTVWRXDRKAHEAD-UHFFFAOYSA-N 0.000 description 1
- AOZDHFFNBZAHJF-UHFFFAOYSA-N [3-hexanoyloxy-2,2-bis(hexanoyloxymethyl)propyl] hexanoate Chemical compound CCCCCC(=O)OCC(COC(=O)CCCCC)(COC(=O)CCCCC)COC(=O)CCCCC AOZDHFFNBZAHJF-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical class CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid group Chemical group C(CCCCCC)(=O)O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 239000010688 mineral lubricating oil Substances 0.000 description 1
- 150000005002 naphthylamines Chemical class 0.000 description 1
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical class CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- 229940093635 tributyl phosphate Drugs 0.000 description 1
- IELLVVGAXDLVSW-UHFFFAOYSA-N tricyclohexyl phosphate Chemical compound C1CCCCC1OP(OC1CCCCC1)(=O)OC1CCCCC1 IELLVVGAXDLVSW-UHFFFAOYSA-N 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
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
- 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
- C10M2207/284—Esters of aromatic 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
- C10M2207/285—Esters of aromatic polycarboxylic 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
- C10M2207/286—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
- 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
- C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/09—Heterocyclic compounds containing no sulfur, selenium or tellurium compounds in the ring
-
- 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
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
-
- 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
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/041—Triaryl phosphates
-
- 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
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
Definitions
- the ester base comprises the major portion of the fully formulated synthetic ester base lubricating oil composition.
- this ester base fluid is present in concentrations from about to 98 percent of the composition.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Abstract
Synthetic lubricating oil composition comprising a major portion of an aliphatic ester base oil having lubricating properties formed from the reaction of a pentaerythritol or trimethylolpropane and an organic monocarboxylic acid containing (a) from about 0.005 to 0.5 percent of a thiouracil compound, (b) from about 0.3 to 5 percent of an alkyl or alkaryl phenylnaphthylamine; (c) from about 0.3 to 5 percent of a dialkyldiphenylamine; and (d) from about 0.25 to 10 percent of a hydrocarbyl phosphate ester.
Description
United States Patent 11 1 [111 3,901,815
Reale, Jr. 1 Aug. 26, 1975 [54] SYNTHETIC AIRCRAFT TURBINE OIL 3,779,921 12/1973 Patmore et a], 252/475 X 3,798 164 3/1974 Kmet eta]. 252/475 [75 lnventor: John Reale, Jr., Wappmgers Falls,
Primary Examiner-Delbert E. Gantz 173 l Assignee: Texaco Inc.. New York. NY. Assistant Examiner-Andrew H. Metz Attorney, Agent, or Firm-T. I-I. Whaley; C. G. Ries; [22] Fil i J n 1 James J. OLoughlin [21] Appl. No.: 476,625
[57] ABSTRACT [52] CL 252/46'7: 252/475 52 35 6 Synthetic lubricating oil composition comprising a major portion of an aliphatic ester base oil having 1n- [51] Int. Cl CIOm 1/48 f d f th f Field 0 Search 252/46 7 47 5 ricatlng proper res orme rom e reac ion 0 a pentaerythntol or trimethylolpropane and an organlc monocarboxylic acid containing (a) from about 0.005 [56] References cued to 0.5 percent of a thiouracil compound, (b) from UNITED STATES PATENTS about 0.3 to 5 percent of an alkyl or alkaryl phenyl- 2.800,491 7/1957 Ellis 252/475 X naphthylamine; (c) from about 0.3 to 5 percent of a 9 3/1960 Tifimey 6131- dialkyldiphenylamine; and (d) from about 0.25 to 10 3,404,090 10/1968 Betty a a1. 252/475 percent f a hydrocarbw phosphate esten 3,476,685 11/1969 Oberender et al 252/467 3,553,131 1/1971 Hepplewhite et a1 252/467 9 Claims, No Drawings SYNTHETIC AIRCRAFT TURBINE OIL BACKGROUND OF THE INVENTION 1. Field of the Invention This invention is concerned with the lubricating oil 5 composition used in gas turbine or jet engines. Gas turbine engines are operated under extreme environmental conditions. The lubricant must be fluid at extremely low temperatures and must be an effective lubricant in an engine which produces internal engine temperatures in the range of 450500F. or above. These operating conditions put severe stresses on the lubricating oil, so much so that the most advanced mineral lubricating oil compositions cannot be employed in gas turbine engines.
Currently, synthetic ester base lubricating oil compositions containing a critically balanced blend of additives are being effectively employed for lubricating gas turbine engines. These ester base oils are operative over a wide temperature range and exhibit high thermal stability, anti-wear, load-carrying and antioxidation properties while providing good lubrication.-
With the advent of newer and more powerful gas turbine engines designed to provide advanced levels of supersonic flight, the resulting higher stress levels require lubricating oil compositions having improved loadcarrying properties.
2. Description of the Prior Art No patents are known which disclose thiouracils or their salts as load-carrying additives for synthetic ester base lubricating oil composition.
SUMMARY OF THE INVENTION The synthetic lubricating oil composition of the invention comprises a major portion of an aliphatic ester base oil having lubricating properties containing a thiouracil compound, an alkylphenyl or alkarylphenyl naphthylamine, a dialkyldiphenylamine, and a hydrocarbyl phosphate. More specifically, the lubricating oil composition of the invention comprises a major portion of an aliphatic ester base oil formed from the reaction of a pentaerythritol or trimethylolpropane and an organic monocarboxylic acid having from about 2 to l8 carbon atoms per molecule containing:
a. from about 0.005 to 0.5 weight percent of a thiouracil compound selected from the class of thiouracils, dithiouracils and their amine salts.
b. from about 0.3 to 5 percent by weight of the lubrieating oil composition of allkyl or alkaryl derivatives of 50 phenyl or or B naphthylamines in which the alkyl radicals have from four to 12 carbon atoms.
0. from about 0.3 to 5 percent of a dialkyldiphenylamine in which the alkyl radicals have from four to 12 carbon atoms, and
d. from about 0.25 to l0 percent of a trihydrocarbyl phosphate in which the hydrocarbyl radicals contain from about two to 12 carbon atoms.
The lubricating oil of the invention is characterized by possessing outstanding load-carrying properties. These properties are attributed to a carefully balanced and formulated synthetic ester base lubricating oil blend containing a thiouracil compound. The results were surprising and unexpected because heretofore thiouracil compounds have not been known to impart load-carrying properties to a synthetic ester lubricating oil composition.
The base fluid component of the lubricant of the invention is an ester-base fluid prepared from pentaerythritol or trimethylolpropane and a mixture of hydrocarbyl monocarboxylic acids. Polypentaerythritols, such as dipentaerythritol, tripentaerythritol and tetrapentaerythritol can also be employed in the reaction to prepare the base oil.
The hydrocarbon monocarboxylic acids which are used to form the ester-base fluid include the straightchain and branched-chain aliphatic acids, cycloaliphatic acids and aromatic acids as well as mixtures of these acids. The acids employed have from about two to 18 carbon atoms per molecule, and preferably from about five to 10 carbon atoms. Examples of suitable specific acids are acetic, propionic, butyric, valeric, isovaleric, caproic, decanoic, hexadecanoic, vinylbenzoic, dodecylbenzoic, pelargonic, cyclohexanoic, naphthenic, benzoic, phenylacetic, tertiary-butylacetic and 2-ethylhexanoic acids.
In general, the acids are reacted in proportions leading to a completely esterified pentaerythritol or trimethylolpropane with the preferred ester base being the pentaerythritol tetraesters. Examples of commercially available tetresters include pentaerythritol tetracaproate, which is prepared from purified pentaerythritol and crude caproic acid containing other C monobasic acids. Another suitable tetraester is prepared from a technical grade pentaerythritol and a mixture of acids comprising 38 percent valeric, l3 percent 2-methyl pentanoic, 32 percent octanoic and 17 percent pelargonic acids. Another effective ester is the triester of trimethylolpropane in which the trimethylolpropane is esterified with a monobasic acid mixture consisting of 2 percent valeric, 9 percent caproic, 13 percent heptanoic, 7 percent octanoic, 3 percent caprylic, 65 percent palargonic and 1 percent capric acids. Trimethylolpropane triheptanoate, trimethylolpropanepentanoate and trimethylolpropanehexanoate are also suitable ester bases.
The ester base comprises the major portion of the fully formulated synthetic ester base lubricating oil composition. In general, this ester base fluid is present in concentrations from about to 98 percent of the composition.
The essential thiouracil compound is selected from the group consisting of the thiouracils, dithiouracils and the amine salts of these compounds.
The thiouracils are represented by the formula:
in which R is hydrogen or a hydrocarbyl radical having from one to about 30 carbon atoms. A preferred class of compounds are those in which R is hydrogen, an alky], aryl, or alkaryl radical having from one to about eight carbon atoms and particularly from one to six carbon atoms.
The dithiouracils are represented by the formula:
in which R has the values noted above.
The amine salt of a thiouracil compound is represented by the formula:
c=c -s-c \N Y in which R has the values noted above and Y represents hydrogen or an ammonium radical represented by the formula H NR in which R is a hydrocarbyl radical having from one to 24 carbon atoms, at least one Y member being said ammonium radical.
Specific examples of effective thiouracil compounds include the following:
2-thiouracil tS-methyl Z-thiouracil fi-elhyl 2 thiouracil 6-propyl Z-thiouracil o-phenyl 2 thiouracil b-benzyl Z-Ihiouracil 5.6-dimethyl 2-thiouracil 5 ,fi-diphenyl 2thiouracil 6-( 4-isopropylphenyl Z-thiouracil Specific examples of dithiouracil compounds include the following:
2,4dithiouracil fi-methyl 2,4-dithiouracil 6-ethyl 2,4-dithiouracil 6propyl 2,4-dithiouracil 6-phenyl 2,4-dithiouracil 6 benzyl 2,4dithiouracil 5,6-dimethyl 2.4-dithiouracil 5,6-diphenyl 2,4-difl1iouracil 65 about 0.005 to 0.5 weight percent with the preferred concentration ranging from about 0.0l to 0.1 weight percent.
The essential alkyl or alkaryl phenyl naphthylamine component of the invention is represented by the formula:
in which R is an alkyl or alkaryl radical having from about three to 12 carbon atoms. This radical can be a straight or branched chain alkyl radical with the tertiary alkyl structure being preferred or it can be an alkaryl radical. The naphthylamine can be either an alpha or beta naphthylamine. Specific effective compounds of this class include N-(p-t-octylphenyDanaphthylamine. N-( p-a-cumylphenyl )-6-a-cumyl-B- naphthylamine, N(p-t-octylphenyl)-B-naphthylamine and the corresponding p-t-dodecylphenyl, p-tbutylphenyl, and p-dodeeylphenyl-o: and -B-naphthy1 amines. The preferred concentration of this component is from about 0.5 to 2.5 percent.
Another essential component of the lubricating oil composition of the invention is a dialkyldiphenylamine. These compounds are represented by the formula:
in which R is an alkyl radical having from about four to 12 carbon atoms. Suitable alkylamines include dioctyldiphenylamine, didecyldiphenylamine, didodecyldiphenylamine, dihexyldiphenylamine and similar compounds. The preferred compound is p,p'-di-toctyldiphenylamine and the preferred concentration isfrom 0.5 to 2.0 percent.
The final essential component of the lubricating oil composition of the invention is a hydrocarbylphosphate ester. more specifically a trihydrocarbyl phosphate having the formula (RO) PO in which R is a hydrocarbyl radical i.e. an alkyl, aryl, alkaryl, cycloalkyl or aralkyl radical or mixture thereof having from two to 12 carbon atoms and preferably from four to eight carbon atoms. Effective specific compounds include tricresylphosphate, cresyl diphenylphosphate, triphenylphosphate, tributylphosphate, tri( 2-ethylhexyl)- phosphate and tricyclohexyl phosphate. These compounds are preferably present in the lubricating oil composition in a concentration ranging from about 0.5 to 5 percent.
The lubricating oil composition of the invention was tested for its load-carrying property in the [AB Gear Test conducted in accordance with the institute of Fetroleum Test Method lPl66" and the Ryder Gear Test conducted in accordance with the ASTM Dl947 standard.
The ester base oils employed in preparing the lubricating oil compositions tested below comprised pentaerythritol containing a minor amount of dipentaerythritol esterified with mixtures of fatty acids.
Base Oil A consisted of technical grade pentaerythritol ester made from a mixture of carboxylic acids consisting of (mole 96):
This ester base oil had the following properties:
Viscosity, on at 2l0'F. 5.03 Viscosity, cs at lF. 25.l Viscosity, cl at 40F. 7247 Viscosity Index 140 Flalh, 'F. 490
TABLE I EVALUATION OF THIOURACIL COMPOUNDS LOAD-CARRYING ABILITY Conc. IAE GEAR RYDER GEAR Run Additive Wt.% TEST, l l0C TEST ppi 6000 rpm 1. None 40 2055 2. Dithiour- 0.085 55 3025 acil 3. C -C 0.5 3075 alkylprimary amine salt of dithiouracil 4. 2-thiour- 0.05 2340 acil The novel synthetic ester base lubricant of the invention containing a thiouracil compound possesses outstanding load-carrying properties as shown in the lAE Gear and the Ryder Gear Tests above. These lubricants are highly effective for providing a synthetic lubricating oil composition which can meet the ever increasing stresses put on the lubricants by the new and larger gas turbine engines.
l claim:
1. A synthetic lubricating oil composition comprising a major portion of an aliphatic ester base oil having lubricating properties formed from the reaction of a pentaerythritol or trimethylolpropane and a saturated hydrocarbyl monocarboxylic acid having from about 2 to 18 carbon atoms per moledule, containing A. From about 0.005 to 0.5 weight percent of a thiouracil compound represented by the formula selected from the group consisting of I l c c m t 2 l'lll i l c 0 (ii! 5 (2/ Nil d I II /c c um -s C Y2 wherein R is hydrogen or a hydrocarbyl radical having from one to about 30 carbon atoms and Y is hydrogen or an ammonium radical having the formula H NR' in which R is a hydrocarbyl radical having from one to 24 carbon atoms, at least one Y being said ammonium radical.
8. From about 0.3 to 5 percent by weight of the lubricating oil composition of an alkyl or alkaryl phenyl naphthylamine in which the alkyl radical has from three to 12 carbon atoms,
C. From about 0.3 to 5 percent of a dialkyldiphenylamine in which the alkyl radicals have from four to 12 carbon atoms, and
D. From about 0.25 to 10 percent of a trihydrocarbyl phosphate in which said hydrocarbyl radicals contain from about two to 12 carbon atoms.
2. A lubricating oil composition according to claim 1 in which said thiouracil compound is a thiouracil represented by the formula:
in which R is hydrogen or a hydrocarbyl radical having from one to about 30 carbon atoms.
3. A lubricating oil composition according to claim 1 in which said thiouracil compound is a dithiouracil represented by the fon'nula:
in which R is hydrogen or a hydrocarbyl radical having from one to about 30 carbon atoms.
in which R is hydrogen or a hydrocarbyl radical having from one to about 30 carbon atoms, and Y is hydrogen or an ammonium radical having the formula H NR in which R is a hydrocarbyl radical having from one to 24 carbon atoms, at least one Y member being said ammonium radical 5. A lubricating oil composition according to claim 1 in which said thiouracil compound is dithiouracil.
6. A lubricating oil composition according to claim 1 in which said thiouracil compound is C -C -t-alkyl primary amine salt of dithiouracil.
7. A lubricating oil composition according to claim 1 in which saidthiouracil compound is 2-thiouracil.
8. A lubricating oil composition according to claim 1 in which said thiouracil compound is 6-methyl-2- thiouracil.
9. A lubricating oil composition according to claim 1 in which said thiouracil compound is 2-ethylhexylamine salt of 2,4-dithiouracil.
Claims (9)
1. A SYNTHATIC LUBERCATING OIL COMPOSITION COMPRISING A MAJOR PORTION OF AN ALIPHATIC ESTER BASE OIL HAVING LUBERCATING PROPERTIES FORMED FROM THE REACTION OF A PENTAERYTHRITOL OF TRIMETHYLOPROPANE AND A SATURATED HYDROCARBYL MONOCARBOXYLIC ACID HAVING FROM ABOUT 2 TO 18 CARBON TOMS PER MOLEDULE, CONTAINING A. FROM ABOUT 0.005 TO 0.5 WEIGHT PERCENT OF A THIOURACIL COMPOUND REPRESENTED BY THE FORMULA SELECTED FROM THE GROUP CONTAINING OF
2. A lubricating oil composition according to claim 1 in which said thiouracil compound is a thiouracil represented by the formula:
3. A lubricating oil composition according to claim 1 in which said thiouracil compound is a dithiouracil represented by the formula:
4. A lubricating oil composition according to claim 1 containing the amine salt of said thiouracil compound represented by the formula:
5. A lubricating oil composition according to claim 1 in which said thiouracil compound is dithiouracil.
6. A lubricating oil composition according to claim 1 in which said thiouracil compound is C18-C22 -t-alkyl primary amine salt of dithiouracil.
7. A lubricating oil composition according to claim 1 in which said thiouracil compound is 2-thiouracil.
8. A lubricating oil composition according to claim 1 in which said thiouracil compound is 6-methyl-2-thiouracil.
9. A lubricating oil composition according to claim 1 in which said thiouracil compound is 2-ethylhexyl-amine salt of 2,4-dithiouracil.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US476625A US3901815A (en) | 1974-06-05 | 1974-06-05 | Synthetic aircraft turbine oil |
| DE19752528526 DE2528526A1 (en) | 1974-06-05 | 1975-06-26 | LUBRICATING OIL FORMULATION |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US476625A US3901815A (en) | 1974-06-05 | 1974-06-05 | Synthetic aircraft turbine oil |
| DE19752528526 DE2528526A1 (en) | 1974-06-05 | 1975-06-26 | LUBRICATING OIL FORMULATION |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3901815A true US3901815A (en) | 1975-08-26 |
Family
ID=25769075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US476625A Expired - Lifetime US3901815A (en) | 1974-06-05 | 1974-06-05 | Synthetic aircraft turbine oil |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3901815A (en) |
| DE (1) | DE2528526A1 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53136170A (en) * | 1977-05-02 | 1978-11-28 | Asahi Denka Kogyo Kk | Synthetic ester family working oil composite |
| US4784782A (en) * | 1986-03-27 | 1988-11-15 | The Lubrizol Corporation | Heterocyclic compounds useful as additives for lubricant and fuel compositions |
| US20040029743A1 (en) * | 2002-08-07 | 2004-02-12 | Ravindranath Mukkamala | Cyclic thioureas as additives for lubricating oils |
| WO2013090051A1 (en) | 2011-12-13 | 2013-06-20 | Chemtura Corporation | Cross products and co-oligomers of phenylenediamines and aromatic amines as antioxidants for lubricants |
| US8987515B2 (en) | 2011-12-13 | 2015-03-24 | Chemtura Corporation | Cross products and co-oligomers of phenylenediamines and aromatic amines as antioxidants for lubricants |
| CN114479988B (en) * | 2020-10-27 | 2023-11-10 | 中国石油化工股份有限公司 | Antioxidant composition and preparation method thereof |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2800491A (en) * | 1954-12-14 | 1957-07-23 | Stauffer Chemical Co | Oxidation-resistant oleaginous materials |
| US2930758A (en) * | 1956-09-28 | 1960-03-29 | Texaco Inc | Ester-base lubricant containing anti-oxidant mixtures |
| US3404090A (en) * | 1967-02-14 | 1968-10-01 | Armour & Co | Water base lubricant |
| US3476685A (en) * | 1967-05-08 | 1969-11-04 | Texaco Inc | Synthetic lubricating composition |
| US3553131A (en) * | 1967-04-24 | 1971-01-05 | Mobil Oil Corp | Lubricant containing an aminephosphonate combined additive |
| US3779921A (en) * | 1972-08-21 | 1973-12-18 | Texaco Inc | Synthetic aircraft turbine oil |
| US3798164A (en) * | 1971-05-24 | 1974-03-19 | Richardson Co | Polyoxyalkylene bis-thiourea extreme pressure agents and methods of use |
-
1974
- 1974-06-05 US US476625A patent/US3901815A/en not_active Expired - Lifetime
-
1975
- 1975-06-26 DE DE19752528526 patent/DE2528526A1/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2800491A (en) * | 1954-12-14 | 1957-07-23 | Stauffer Chemical Co | Oxidation-resistant oleaginous materials |
| US2930758A (en) * | 1956-09-28 | 1960-03-29 | Texaco Inc | Ester-base lubricant containing anti-oxidant mixtures |
| US3404090A (en) * | 1967-02-14 | 1968-10-01 | Armour & Co | Water base lubricant |
| US3553131A (en) * | 1967-04-24 | 1971-01-05 | Mobil Oil Corp | Lubricant containing an aminephosphonate combined additive |
| US3476685A (en) * | 1967-05-08 | 1969-11-04 | Texaco Inc | Synthetic lubricating composition |
| US3798164A (en) * | 1971-05-24 | 1974-03-19 | Richardson Co | Polyoxyalkylene bis-thiourea extreme pressure agents and methods of use |
| US3779921A (en) * | 1972-08-21 | 1973-12-18 | Texaco Inc | Synthetic aircraft turbine oil |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53136170A (en) * | 1977-05-02 | 1978-11-28 | Asahi Denka Kogyo Kk | Synthetic ester family working oil composite |
| US4784782A (en) * | 1986-03-27 | 1988-11-15 | The Lubrizol Corporation | Heterocyclic compounds useful as additives for lubricant and fuel compositions |
| US5308520A (en) * | 1986-03-27 | 1994-05-03 | The Lubrizol Corporation | Heterocyclic compounds useful as additives for lubricant and fuel compositions |
| US5366516A (en) * | 1986-03-27 | 1994-11-22 | The Lubrizol Corporation | Heterocyclic compounds useful as additives for lubricant and fuel compositions |
| US20040029743A1 (en) * | 2002-08-07 | 2004-02-12 | Ravindranath Mukkamala | Cyclic thioureas as additives for lubricating oils |
| EP1394241A1 (en) * | 2002-08-07 | 2004-03-03 | Rohm And Haas Company | Cyclic thioureas as additives for lubricating oils |
| WO2013090051A1 (en) | 2011-12-13 | 2013-06-20 | Chemtura Corporation | Cross products and co-oligomers of phenylenediamines and aromatic amines as antioxidants for lubricants |
| US8987515B2 (en) | 2011-12-13 | 2015-03-24 | Chemtura Corporation | Cross products and co-oligomers of phenylenediamines and aromatic amines as antioxidants for lubricants |
| CN114479988B (en) * | 2020-10-27 | 2023-11-10 | 中国石油化工股份有限公司 | Antioxidant composition and preparation method thereof |
| CN114479989B (en) * | 2020-10-27 | 2023-11-10 | 中国石油化工股份有限公司 | Antioxidant composition, preparation method thereof and lubricating oil composition |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2528526A1 (en) | 1977-01-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3720612A (en) | Synthetic ester lubricating oil compositions | |
| US3247111A (en) | High temperature jet lubricant | |
| US3850824A (en) | Synthetic aircraft turbine oil | |
| US3218256A (en) | Lubricating compositions | |
| US3185644A (en) | Lubricating compositions containing amine salts of boron-containing compounds | |
| US4320018A (en) | Synthetic aircraft turbine oil | |
| US3476685A (en) | Synthetic lubricating composition | |
| GB2126245A (en) | Synthetic ester lubricating oil composition | |
| US3697427A (en) | Lubricants having improved anti-wear and anti-corrosion properties | |
| US4226732A (en) | Synthetic aircraft turbine oil | |
| US3790481A (en) | Synthetic lubricants for aero gas turbines | |
| US3053768A (en) | Synthetic lubricant compositions | |
| US3951973A (en) | Di and tri (hydrocarbylammonium) trithiocyanurate | |
| US4096078A (en) | Synthetic aircraft turbine oil | |
| US3901815A (en) | Synthetic aircraft turbine oil | |
| US3535243A (en) | Stable synthetic ester lubricant compositions | |
| US4157971A (en) | Synthetic aircraft turbine oil | |
| US3134737A (en) | Novel titanium compound and lubricating composition containing said compound | |
| US3779919A (en) | Synthetic aircraft turbine oil | |
| US4189388A (en) | Synthetic aircraft turbine oil | |
| US2836565A (en) | Lubricating compositions | |
| US4119551A (en) | Synthetic aircraft turbine lubricating oil compositions | |
| US3779921A (en) | Synthetic aircraft turbine oil | |
| US4124514A (en) | Synthetic aircraft turbine lubricating oil compositions | |
| US4157970A (en) | Synthetic aircraft turbine oil |