US3376225A - Lubricating oil containing trithione-soxides as antioxidants - Google Patents
Lubricating oil containing trithione-soxides as antioxidants Download PDFInfo
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- US3376225A US3376225A US555245A US55524566A US3376225A US 3376225 A US3376225 A US 3376225A US 555245 A US555245 A US 555245A US 55524566 A US55524566 A US 55524566A US 3376225 A US3376225 A US 3376225A
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- Prior art keywords
- trithione
- lubricating oil
- antioxidants
- soxides
- oil containing
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- Expired - Lifetime
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- 239000010687 lubricating oil Substances 0.000 title claims description 4
- 239000003963 antioxidant agent Substances 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims description 10
- 230000003064 anti-oxidating effect Effects 0.000 claims description 2
- 239000003921 oil Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- -1 e.g. Substances 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 230000001050 lubricating effect Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- DRHABPMHZRIRAH-UHFFFAOYSA-N 2,4,4,6,6-pentamethylhept-2-ene Chemical group CC(C)=CC(C)(C)CC(C)(C)C DRHABPMHZRIRAH-UHFFFAOYSA-N 0.000 description 1
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 1
- URRHKOYTHDCSDA-UHFFFAOYSA-N 2,5,8,11-tetramethyldodec-2-ene Chemical group CC(C)CCC(C)CCC(C)CC=C(C)C URRHKOYTHDCSDA-UHFFFAOYSA-N 0.000 description 1
- 101000737090 Agrotis ipsilon Neuropeptide CCHamide-2 Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003376 silicon Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/04—Five-membered rings having the hetero atoms in positions 1 and 2, e.g. lipoic acid
-
- 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
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
-
- 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
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
-
- 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
-
- 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
- C10M2219/10—Heterocyclic compounds containing 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
-
- 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
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/106—Thiadiazoles
Definitions
- Trithiones are .well known to Trithione compositions have been repeatedly reported in the literature. See for-example*U.S.-Paitent No. 2,995,569.
- R and R are hydrogen or hydrocarbyl (hydrocarbyl is a monovalent organic radical composed solely of carbon and hydrogen which may be aliphatic, alicyclic or aromatic, or combinations thereof, e.g., aralkyl), usually aliphatic hydrocarbyl, of a total of l to 22 carbon atoms, when other than hydrogen. Most usually, R and R will be alkyl of from about 1 to 8 carbon atoms, more usually of from about 1 to 6 carbon atoms.
- the oxy derivative may then be prepared by dissolving the trithione in a suitable inert solvent, e.g., benzene, followed by the addition of hydrogen peroxide at ambient temperatures in the presence of a hydroxylic organic solvent, e.g., methanol, acetic acid, etc.
- a suitable inert solvent e.g., benzene
- hydrogen peroxide at ambient temperatures in the presence of a hydroxylic organic solvent, e.g., methanol, acetic acid, etc.
- Olefins which find use in the preparation of the trithione are isobutylene, diisobutylene, triisobutylene, tetraisobutylene, 2-methyl-2-butene, 2,4,4-dirnethylpentene, etc.
- the trithiones may also be prepared from compounds having functionalities other than olefinic, e.g., ketonic.
- the S-oxy trithione may be included in various lubricating media, i.e., oils and greases.
- oils lubricating fluids which may be used with the compounds of this invention (hereinafter referred to as oils) may be derived from natural or synthetic sources. Oils generally have viscosities of from about 35 to 50,000 Saybolt Universal seconds (SUS) at 100 F.
- SUS Saybolt Universal seconds
- natural hydrocarbonaceous oils are paraffin base, naphthenic base, asphaltic base and mxied base oils.
- Illustrative synthetic oils are: hydrocarbon oils, such as polymer of various olefins, genearlly of from 2 to 8 carbon atoms, and alkylated aromatic hydrocarbons; and nonhydrocarbon oils, such as polyalkylene oxides, aromatic ethers, carboxylate esters, phosphate esters and silicon esters.
- the preferred media are the hydrocarbonaceous media, both natural and synthetic.
- oils may be used individually or together, whenever miscible or made so by the use of mutual solvents.
- additives may also-be present such as :detergents, extreme pressure agents, grease thickeners, dyes,.oiliness” agents, corrosion inhibitors, etc.
- EXAMPLE K Into a reaction flask was introduced 48.55 g. (0.19 mole) of 4-neopentyl-5-t.-butyl-1,2-dithiole-3-thione, 200 ml.of 'methanoland 25 'ml. ofethyl etheriTothis mix ture was slowly added 21.2 g. (0.19'mo1e) of 30% aqueous hydrogen peroxide in ml. of methanol. During the addition the temperature was maintained between 35 and 40 C. When the addition was completed, the reaction mixture was refluxed for 1 hour. At the end of this time, the reaction mixture was transferred to a separatory funnel, diluted with 250 ml. of water and extracted 3 times with m1.
- a clean copper strip 1" x 3" x g" thickness is immersed in 300 ml. of a Mid-Continent SAE 30 oil and held in the oil at 340 F. for 20 hours, while the oil is stirred with a stirrer rotating at 800 rpm.
- the strip is then removed, washed with hexanes, allowed to dry and weighed.
- the strip is then washed with a potassium cyanide solution (40 g. of potassium cyanide in 160 ml. of water), rinsed with water, then acetone, allowed to dry and reweighed.
- the potassium cyanide removes any scale which may be present.
- a lubricating oil composition containing in an amount sufiicient for antioxidation a corn-position of the formula:
- R and R are hydrogen or hydrocarbyl having a total of from 1 to 22 carbon atoms.
- composition according to claim 1 wherein R and R when other than hydrogen, are aliphatic.
- composition according to claim 1 wherein R and R are alkyl of from about 1 to 8 carbon atoms.
- composition according to claim 1 wherein R is neopentyl and R is tert.-butyl.
- composition according to claim 1 wherein said amount is in the range of 0.1 to 5 weight percent.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Lubricants (AREA)
Description
United States Patent 9 1 3,376,225 LUBRICATING OIL CONTAINING TRITHIONE-S- OXIDES'IAS ANTIOXIDANTS. Donald J. AndersomSan Anselmo, Calif., assignor to Chevron Research Company, San Francisco, Calif., a corporation of Delaware p v No Drawing. Filed June 6, 1966, Ser, No. 555,245 5 Claims. (Cl. 252-481) This-invention concerns. novel lubricating oil compositions having sulfur containing antioxidants.
Trithiones are .well known to Trithione compositions have been repeatedly reported in the literature. See for-example*U.S.-Paitent No. 2,995,569.
S C=SO S wherein R and R are hydrogen or hydrocarbyl (hydrocarbyl is a monovalent organic radical composed solely of carbon and hydrogen which may be aliphatic, alicyclic or aromatic, or combinations thereof, e.g., aralkyl), usually aliphatic hydrocarbyl, of a total of l to 22 carbon atoms, when other than hydrogen. Most usually, R and R will be alkyl of from about 1 to 8 carbon atoms, more usually of from about 1 to 6 carbon atoms.
The S-oxy trithione compositions can be prepared according to the methods disclosed in the art. Most conveniently, an olefin having the following functionality HC I=CCHa is contacted with sulfur at an elevated temperature, usually in excess of 175 C. and generally less than 275 C. for periods ranging from about 2 to 24 hours. The trithione compound may then be directly isolated.
The oxy derivative may then be prepared by dissolving the trithione in a suitable inert solvent, e.g., benzene, followed by the addition of hydrogen peroxide at ambient temperatures in the presence of a hydroxylic organic solvent, e.g., methanol, acetic acid, etc.
Olefins which find use in the preparation of the trithione are isobutylene, diisobutylene, triisobutylene, tetraisobutylene, 2-methyl-2-butene, 2,4,4-dirnethylpentene, etc.
The trithiones may also be prepared from compounds having functionalities other than olefinic, e.g., ketonic.
See Landis, Chem. Rev., 65 237 (1965).
The S-oxy trithione may be included in various lubricating media, i.e., oils and greases. The lubricating fluids which may be used with the compounds of this invention (hereinafter referred to as oils) may be derived from natural or synthetic sources. Oils generally have viscosities of from about 35 to 50,000 Saybolt Universal seconds (SUS) at 100 F. Among natural hydrocarbonaceous oils are paraffin base, naphthenic base, asphaltic base and mxied base oils. Illustrative synthetic oils are: hydrocarbon oils, such as polymer of various olefins, genearlly of from 2 to 8 carbon atoms, and alkylated aromatic hydrocarbons; and nonhydrocarbon oils, such as polyalkylene oxides, aromatic ethers, carboxylate esters, phosphate esters and silicon esters. The preferred media are the hydrocarbonaceous media, both natural and synthetic.
The above oils may be used individually or together, whenever miscible or made so by the use of mutual solvents.
have antioxidant activity.-
Otheradditives may also-be present such as :detergents, extreme pressure agents, grease thickeners, dyes,.oiliness" agents, corrosion inhibitors, etc.
The following example is offered by way of illustration and not by way of limitation.
EXAMPLE K Into a reaction flask was introduced 48.55 g. (0.19 mole) of 4-neopentyl-5-t.-butyl-1,2-dithiole-3-thione, 200 ml.of 'methanoland 25 'ml. ofethyl etheriTothis mix ture was slowly added 21.2 g. (0.19'mo1e) of 30% aqueous hydrogen peroxide in ml. of methanol. During the addition the temperature was maintained between 35 and 40 C. When the addition was completed, the reaction mixture was refluxed for 1 hour. At the end of this time, the reaction mixture was transferred to a separatory funnel, diluted with 250 ml. of water and extracted 3 times with m1. fractions of diethyl ether. The combined ether fractions were dried and the ether distilled off. The residue weighed 41.92 g. After standing overnight, the residue crystallized and was recrystallized in an ether pentane solution. Melting point 83-35" C. An infrared spectrum was consistent wtih the S-oxy 4- neopentyl-5-t.-butyl-1,2-dithiole-3-thione structure.
In order to demonstrate the effectiveness as an antioxidant of the S-oxy trithione, the following test was carried out. To 25 g. of a Mid-Continent SAE 30 oil was added 0.2 cc. of a solution having 3,160 ppm. of copper, 2,670 ppm. of iron, p.p.m. of manganese, 36,700 p.p.m. of lead and 1,631 p.p.m. of tin, all as their naphthenates, providing a distribution of metals which would be expected to be found in used crankcase oils after an L-4 Chevrolet engine test. The oil sample to be tested is maintained at 340 F. and the time required to absorb 250 ml. of oxygen is observed. The results are reported as if 100 g. was used and 1,000 ml. of oxygen absorbed. Without the additive, the oxygen was absorbed in 0.12 hour, while with the additive the time required was 3.21 hours.
In order to demonstrate the significant decrease in copper corrosion, the following test was carried out. A clean copper strip 1" x 3" x g" thickness is immersed in 300 ml. of a Mid-Continent SAE 30 oil and held in the oil at 340 F. for 20 hours, while the oil is stirred with a stirrer rotating at 800 rpm. The strip is then removed, washed with hexanes, allowed to dry and weighed. The strip is then washed with a potassium cyanide solution (40 g. of potassium cyanide in 160 ml. of water), rinsed with water, then acetone, allowed to dry and reweighed. The potassium cyanide removes any scale which may be present.
Two samples were prepared, one containing 0.5 weight percent of 4 neopentyl-5-t.-butyl-1,2 dithiole-3-thione and the other containing 0.5 weight percent of the S-oxy derivative of the same trithione, and a third sample without additive used as a control. The following table indicates the results:
TAB LE I Copper Weight Loss (mg) Before KCN After KCN Trithione 342 365 S-oxy trithione 18. 6 25. 7 No additive 124 128 will generally range from- As will be evident to those skilled in the art, various modifications on this invention can be made or followed, in the light of the foregoing disclosure and discussion, without departing from the spirit or scope of the disclosure or from the scope of the following claims.
I claim:
1. A lubricating oil composition containing in an amount sufiicient for antioxidation a corn-position of the formula:
wherein R and R are hydrogen or hydrocarbyl having a total of from 1 to 22 carbon atoms.
2. A composition according to claim 1, wherein R and R when other than hydrogen, are aliphatic.
3. A composition according to claim 1, wherein R and R are alkyl of from about 1 to 8 carbon atoms.
5 4. A composition according to claim 1, wherein R is neopentyl and R is tert.-butyl.
5. A composition according to claim 1, wherein said amount is in the range of 0.1 to 5 weight percent.
References Cited UNITED STATES PATENTS 2,816,075 12/1957 Fields 252-45 2,995,569 8/1961 Hamilton et al. 252406 XR 15 DANIEL E. WYMAN, Primary Examiner.
W. H. CANNON, Assistant Examiner.
Claims (1)
1. A LUBRICATING OIL COMPOSITION CONTAINING IN AN AMOUNT SUFFICIENT FOR ANTIOXIDATION A COMPOSITION OF THE FORMULA:
Priority Applications (1)
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US555245A US3376225A (en) | 1966-06-06 | 1966-06-06 | Lubricating oil containing trithione-soxides as antioxidants |
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US555245A US3376225A (en) | 1966-06-06 | 1966-06-06 | Lubricating oil containing trithione-soxides as antioxidants |
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US3376225A true US3376225A (en) | 1968-04-02 |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3959177A (en) * | 1973-12-07 | 1976-05-25 | Petrolite Corporation | Multifunctional corrosion inhibitors |
JPS51106104A (en) * | 1975-02-17 | 1976-09-20 | Orogil | |
US4012331A (en) * | 1974-07-25 | 1977-03-15 | Edwin Cooper And Company Limited | Sulphur compounds |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2816075A (en) * | 1954-06-01 | 1957-12-10 | Standard Oil Co | Lubricating oil compositions |
US2995569A (en) * | 1957-05-02 | 1961-08-08 | Socony Mobil Oil Co Inc | Process for preparation of alkyl-1, 2-dithiole-3-thiones |
-
1966
- 1966-06-06 US US555245A patent/US3376225A/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2816075A (en) * | 1954-06-01 | 1957-12-10 | Standard Oil Co | Lubricating oil compositions |
US2995569A (en) * | 1957-05-02 | 1961-08-08 | Socony Mobil Oil Co Inc | Process for preparation of alkyl-1, 2-dithiole-3-thiones |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3959177A (en) * | 1973-12-07 | 1976-05-25 | Petrolite Corporation | Multifunctional corrosion inhibitors |
US4012331A (en) * | 1974-07-25 | 1977-03-15 | Edwin Cooper And Company Limited | Sulphur compounds |
JPS51106104A (en) * | 1975-02-17 | 1976-09-20 | Orogil | |
JPS552240B2 (en) * | 1975-02-17 | 1980-01-18 |
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