US2786812A - Mineral oil compositions containing tincontaining dithiophosphate compounds - Google Patents
Mineral oil compositions containing tincontaining dithiophosphate compounds Download PDFInfo
- Publication number
- US2786812A US2786812A US381512A US38151253A US2786812A US 2786812 A US2786812 A US 2786812A US 381512 A US381512 A US 381512A US 38151253 A US38151253 A US 38151253A US 2786812 A US2786812 A US 2786812A
- Authority
- US
- United States
- Prior art keywords
- compounds
- products
- mineral oil
- tincontaining
- oil
- 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
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- 239000002480 mineral oil Substances 0.000 title claims description 6
- 235000010446 mineral oil Nutrition 0.000 title claims description 5
- 239000000203 mixture Substances 0.000 title description 18
- 150000001875 compounds Chemical class 0.000 title description 14
- 150000003606 tin compounds Chemical class 0.000 claims description 6
- 239000000047 product Substances 0.000 description 26
- 239000004215 Carbon black (E152) Substances 0.000 description 13
- 229930195733 hydrocarbon Natural products 0.000 description 13
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- 229910052718 tin Inorganic materials 0.000 description 9
- -1 tin halide Chemical class 0.000 description 9
- 239000000654 additive Substances 0.000 description 8
- 239000000314 lubricant Substances 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 239000010687 lubricating oil Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000005260 corrosion Methods 0.000 description 6
- 230000007797 corrosion Effects 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000010688 mineral lubricating oil Substances 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000000962 organic group Chemical group 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 239000002199 base oil Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000010730 cutting oil Substances 0.000 description 3
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WIKSRXFQIZQFEH-UHFFFAOYSA-N [Cu].[Pb] Chemical compound [Cu].[Pb] WIKSRXFQIZQFEH-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 229960004756 ethanol Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000012988 Dithioester Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- ZSUXOVNWDZTCFN-UHFFFAOYSA-L Tin(II) bromide Inorganic materials Br[Sn]Br ZSUXOVNWDZTCFN-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- DQNJHGSFNUDORY-UHFFFAOYSA-N bis(2-ethylhexoxy)-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCCCC(CC)COP(S)(=S)OCC(CC)CCCC DQNJHGSFNUDORY-UHFFFAOYSA-N 0.000 description 1
- SFIWAVRBROEWBI-UHFFFAOYSA-N bis(butylsulfanyloxy)-sulfanyl-sulfanylidene-lambda5-phosphane Chemical compound C(CCC)SOP(S)(OSCCCC)=S SFIWAVRBROEWBI-UHFFFAOYSA-N 0.000 description 1
- UGEDQORWHYKCGT-UHFFFAOYSA-N bis[(1-methylcyclohexyl)oxy]-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound C1CCCCC1(C)OP(S)(=S)OC1(C)CCCCC1 UGEDQORWHYKCGT-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- QNMWTTFPYZEDCD-UHFFFAOYSA-N butylsulfanyl-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCCCSP(O)(O)=S QNMWTTFPYZEDCD-UHFFFAOYSA-N 0.000 description 1
- NSAODVHAXBZWGW-UHFFFAOYSA-N cadmium silver Chemical compound [Ag].[Cd] NSAODVHAXBZWGW-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- RZAQYVWTBXBLLW-UHFFFAOYSA-N didodecoxy-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCCCCCCCCCCCOP(S)(=S)OCCCCCCCCCCCC RZAQYVWTBXBLLW-UHFFFAOYSA-N 0.000 description 1
- YREAYUWMESCMHJ-UHFFFAOYSA-L didodecyltin(2+);dichloride Chemical compound CCCCCCCCCCCC[Sn](Cl)(Cl)CCCCCCCCCCCC YREAYUWMESCMHJ-UHFFFAOYSA-L 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- IRDLUHRVLVEUHA-UHFFFAOYSA-N diethyl dithiophosphate Chemical class CCOP(S)(=S)OCC IRDLUHRVLVEUHA-UHFFFAOYSA-N 0.000 description 1
- ZMJYZFFBAHUZSF-UHFFFAOYSA-L dipotassium (4,4-dimethylcyclohexyl)sulfanyl-dioxido-sulfanylidene-lambda5-phosphane Chemical compound P(=S)(SC1CCC(CC1)(C)C)([O-])[O-].[K+].[K+] ZMJYZFFBAHUZSF-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000005022 dithioester group Chemical group 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- AVGQPNBPXNPEPF-UHFFFAOYSA-N ethylsulfanyl-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCSP(O)(O)=S AVGQPNBPXNPEPF-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000012208 gear oil Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- KJSACGHPPNXZFT-UHFFFAOYSA-M iodo(triphenyl)stannane Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(I)C1=CC=CC=C1 KJSACGHPPNXZFT-UHFFFAOYSA-M 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- YICRPERKKBDRSP-UHFFFAOYSA-N methyl 3-amino-4-methylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC=C(C)C=1N YICRPERKKBDRSP-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BPLJLGTYWGSFCL-UHFFFAOYSA-M potassium;oxido-propan-2-yloxy-propan-2-ylsulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound [K+].CC(C)OP([O-])(=S)SC(C)C BPLJLGTYWGSFCL-UHFFFAOYSA-M 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010723 turbine oil Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
-
- 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
- C07F7/22—Tin compounds
- C07F7/226—Compounds with one or more Sn-S linkages
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/26—Organic compounds containing phosphorus
- C10L1/2633—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond)
- C10L1/265—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond) oxygen and/or sulfur bonds
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/108—Residual fractions, e.g. bright stocks
-
- 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
- C10M2209/102—Polyesters
-
- 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
- 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
- C10M2227/08—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 metal-to-carbon bonds
- C10M2227/083—Sn compounds
-
- 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
- C10N2040/02—Bearings
-
- 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
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
-
- 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
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
-
- 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
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
-
- 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
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
-
- 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
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
-
- 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
- C10N2040/135—Steam engines or 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
- C10N2040/14—Electric or magnetic purposes
- C10N2040/16—Dielectric; Insulating oil or insulators
-
- 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
- C10N2040/14—Electric or magnetic purposes
- C10N2040/17—Electric or magnetic purposes for electric contacts
-
- 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
- C10N2040/20—Metal working
- C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
-
- 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
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
-
- 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
- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
Definitions
- the present invention relates to a new class of tin-containing compounds and more particularly to the use of these compounds as additives for various hydrocarbon products. 7 I
- the new class of compounds forming the subject of the present invention are tetravalent tin compounds having four organo radicals comprising at least two oil solubiliz ing hydrocarbon radicals attached directly to the tin through carbon atoms and having at least one dithiophosphate radical attached directly to the tin through a sulfur atom.
- the compounds are conveniently formed by reacting an organo tetravalent tin halide with a salt of a dithid phosphoric acid in such manner that halogen in the tin compound is substantially completely replaced by the organic radical.
- the compounds are stable and soluble in the usual hydrocarbon products such as fuels, lubricating oils and the like, are good anti-corrosive agents for organic materials that tend to corrode the usual metals, and have other useful properties.
- the new class of compounds of the present invention may be more accurately defined by the following general formula:
- R is a hydrocarbon radical, w is 2; to 3, y is 1 to 2 and w plus y totals 4.
- R is also a hydrocarbon radical,
- R and R each preferably have 1 to 20 carbon atoms and may be alkyl, alkenyl, cyc'lo-alkyl, aryl, aralkyl, and alkaryl radicals.
- Alkyl radicals such as methyl, isopropyl, octyl, 'dodecyl, octadecyl'and other straight or branched chain radicals are preferred.
- Otherradicals include phenyl, naphthyl', benzyl, octylphenyl, ethylcyclohexyl, and the like.
- R and R should include suilicient caroon atoms to render the compound solublein hydlrocarbon products and preferably a total of at least 10 carbon atoms are contained in R and R;
- organo tetravalent tin halides used in the preparation of the compounds of the present invention may be represented by the following formula:
- R is a hydrocarbon radical as defined above
- X is a reactive halogen such as chlorine, bromine and iodine
- w is 2 to 3
- y is l to 2 and w plus totals 4.
- Specific compounds include dibutyltindichloride, triphenyltiniodide, tri-tert.-octyltiniodide, tri-cyclohexyltinchloride, din-hexyl-tindibromide' and the like.
- the halide preferably has two R radicals, and the R radicals are preferably alkyl radicals.
- the organo tetravale'nt halides may be prepared by means well known to the art. I
- the salts of dithiophosphoric acids'are represented by RZ s Diester of dithiophosphate Z in the above formulas may be either oxygen or sulfur although oxygen is generally preferred.
- R has the meaning defined above.
- Y is a cation and is preferably ametal equivalent of hydrogen.
- the reactive alkali .and alkaline earth metals such as sodium, potassium, calcium and the like may be used. Ammonium or amine salts may also be used.
- the dithiophosphates are prepared by .wellknown means. a
- Specific salts of the above general types includepotassium, sodium, lithium, barium, ammonium andzthe like salts of diethyldithiophosphoric acid, isoprcpyl ethyl dithiophosphoric acid, didodecyl dithiophosphoric acid, di butyl dithiophosphoric acid, diphenylethyl dithiophosphoric acid, (di-(methylcyclohexyl) dithiophosphoricacid, di-(2-ethylhexyl)dithiophosphoric acid, dicetyldithiophosphonic acid, di-Lorol-B dithiophosphoric'acid (where Lorol-B compounds are derived from Lorol-B alco hol which is a commercial mixture of higher alcohols commonly derived from coconut oil and having from 8 to 18 carbon atoms per molecule), di(butyl mercapto) dithiophosphoric acid, and the like.
- the particular compound selected will'depend largely on the concentrations used and the specific properties to be improved in various hydrocarbon products.
- the dithiophosphate derivatives will sometimes be especially valuable for imparting mild extreme pressure properties to gear oils and the like.
- the dithioester dithiopho'sphate derivatives will generally be preferred for cutting oils where high sulfur concentrations are desired.
- the salt may be added relatively slowly to the tin halide with care being taken to prevent excessive temperature rise as a result of the exothermic reaction which takes place.
- the reactants may be heated together for a period of from about 0.5 to 2 hours, depending on the types of materials present. Preferably, the reaction temperatures are maintained in a range of about 10 to 100 C.
- the reaction is carried out in the presence of an inert solvent in which the halide reaction by-products are insoluble or from which such by-products may be readily removed.
- Such solvents include petroleum ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, acetone, dioxane and the like.
- the heating step may be carried out under refluxing conditions when a solvent is used.
- the resulting metal halide will generally precipitate out of solution and may be removed by filtration, decantation or by other means.
- Solvent may be removed from the finished product by stripping with nitrogen or other inert gas, by distillation or by other means.
- a desired method for producing a relatively pure product is to filter the material, preferably before solvent is removed, through a diatomaceous filter aid such as Hy-flo.”
- the products of the present invention are added to a mineral oil for inhibiting oxidation and preventing corrosion of metal parts and the like, they are preferably used in proportions of about 0.01 to 5% or by weight based on the total composition. A preferred range is from about 0.1 to 2% by Weight. Concentrations up to as high as or even higher may be used for extreme pressure lubricants, cutting oils, and the like. It is usually preferred, when marketing the additive commercially and especially when intended for use in lubricating oils, to prepare a concentrated lubricating oil solution in which the amount of additive in the composition ranges from about 20 to 50% or up to 75% by weight, depending on the solubility of the additive in the oil. The concentrate is then conveniently transported and stored in such form and may be subsequently blended with a base lubricant in the required amount before being used as a crank case oil or the like.
- Product B Dibutyltindi-(dimethylcyclohexyldithiophosphate) This preparation was carried out as described in connection with Product A, using 18.2 g. dibutyltindichloride (0.06 mol) and 43.2 g. potassium dimethylcyclohexyl dithiophosphate (0.12 mol). A viscous, yellow oil was obtained which analyzed 6.7% P, 13.2% S, and 8.8% Sn.
- the additives of the present invention may be used in various lubricating oil base stocks derived from pctroleum distillates and residuals refined by conventional means. Hydrogenated oils or white oils may be employed as well as synthetic oils prepared by polymerization of olefins, by reaction of oxides of carbon with hydrogen, or by hydrogenation of coal. The products may also be used in the synthetic polyether and polyestertype lubricants and the like as such or blended with mineral lubricants. The lubricants will usually range from about 35 to seconds (Saybolt) viscosity at 210 F.
- agents may of course be employed in the oil compositions, such agents including dyes, pour point depressants, sludge dispersers, thickeners, viscosity index improvers, oiliness agents, and the like.
- the additives of the present invention may also be used in other mineral oil products such as motor fuels, heating oils, hydraulic fluids, cutting oils, turbine oils, transformer oils, gear lubricants, greases and other products containing mineral oils as ingredients.
- a mineral oil product having incorporated therein in the range of about 0.01 to 20% by weight of an organo tetravalent tin compound of the formula wherein Z is selected from the class consisting of oxygen and sulfur, and R and R represent hydrocarbon radicals having 1 to 20 carbon atoms.
- composition as in claim 1 wherein said oil product is a lubricating oil is a lubricating oil.
- composition as in claim 1 wherein the R groups are alkyl radicals.
- composition as in claim 1 wherein the R groups are alkaryl radicals.
- a concentrate consisting essentially of a hydrocarbon oil and about 20 to 50% by weight based on said concentrate of an organo-tetravalent tin compound of the formula wherein Z is selected from the class consisting of oxygen and sulfur, and R and R represent hydrocarbon radicals having 1 to 20 carbon atoms.
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Description
John P. McDermott, Springfield, N. 1., assignor to Esso' Research and Engineering Company, a corporation of Delaware No Drawing. Application September 21, 1953, Serial No. 381,512
9 Claims. (Cl. 2552-32-7) The present invention relates to a new class of tin-containing compounds and more particularly to the use of these compounds as additives for various hydrocarbon products. 7 I
I This is a continuation-in-part of Serial No. 256,597, filed November 15, 1951, and now abandoned.
In the development of.marketable hydrocarbon products such as lubricating oils, the trend has been to use more and more efficient refining methods in order to improve their stability and reduce their tendency to form carbon and deposits of solid matter or sludge. While such highly refined materials possess many advantages, their resistance to oxidation, particularly under conditions of severe service, is generally decreased and they are more prone to form soluble acid oxidation products which are corrosive. They are generally less effective than the untdStates,PatenfC treated products in protecting the metal surfaces which they contact against rusting and corrosion due to oxygen and moisture. Such lubricants also often deposit thick films of varnish on hot metal surfaces,-.such as the pistons of internal combustion engines.
In accordance with the present invention a new class of chemical compounds has been discovered, and these compounds have been found to reduce the tendency of refined lubricating oils and other hydrocarbon products to corrode metal surfaces when added in small quantities to such materials. These additives are active in reducing the corrosion of copper-lead and cadmium-silver bearings which are employed in internal combustion engines; they are likewise effective in inhibiting the oxidation of hydrocarbon products generally and especially those of petroleurn origin, and they impart other useful properties to various products.
The new class of compounds forming the subject of the present invention are tetravalent tin compounds having four organo radicals comprising at least two oil solubiliz ing hydrocarbon radicals attached directly to the tin through carbon atoms and having at least one dithiophosphate radical attached directly to the tin through a sulfur atom. The compounds are conveniently formed by reacting an organo tetravalent tin halide with a salt of a dithid phosphoric acid in such manner that halogen in the tin compound is substantially completely replaced by the organic radical. The compounds are stable and soluble in the usual hydrocarbon products such as fuels, lubricating oils and the like, are good anti-corrosive agents for organic materials that tend to corrode the usual metals, and have other useful properties.
The new class of compounds of the present invention may be more accurately defined by the following general formula:
' S ZRI (R)wSn -siy \ZR I wherein R is a hydrocarbon radical, w is 2; to 3, y is 1 to 2 and w plus y totals 4. R is also a hydrocarbon radical,
and Z is selected from the class consisting of oxygen and the following formula:
2,786,812 1 'latented" M811; 25,1
sulfur. R and R each preferably have 1 to 20 carbon atoms and may be alkyl, alkenyl, cyc'lo-alkyl, aryl, aralkyl, and alkaryl radicals. Alkyl radicals such as methyl, isopropyl, octyl, 'dodecyl, octadecyl'and other straight or branched chain radicals are preferred. Otherradicals include phenyl, naphthyl', benzyl, octylphenyl, ethylcyclohexyl, and the like. R and R should include suilicient caroon atoms to render the compound solublein hydlrocarbon products and preferably a total of at least 10 carbon atoms are contained in R and R;
The organo tetravalent tin halides used in the preparation of the compounds of the present invention may be represented by the following formula:
wherein R is a hydrocarbon radical as defined above, X is a reactive halogen such as chlorine, bromine and iodine, w is 2 to 3, y is l to 2 and w plus totals 4. Specific compounds include dibutyltindichloride, triphenyltiniodide, tri-tert.-octyltiniodide, tri-cyclohexyltinchloride, din-hexyl-tindibromide' and the like. The halide preferably has two R radicals, and the R radicals are preferably alkyl radicals. The organo tetravale'nt halides may be prepared by means well known to the art. I
The salts of dithiophosphoric acids'are represented by RZ s Diester of dithiophosphate Z in the above formulas may be either oxygen or sulfur although oxygen is generally preferred. R has the meaning defined above. Y is a cation and is preferably ametal equivalent of hydrogen. The reactive alkali .and alkaline earth metals such as sodium, potassium, calcium and the like may be used. Ammonium or amine salts may also be used. The dithiophosphates are prepared by .wellknown means. a
Specific salts of the above general types includepotassium, sodium, lithium, barium, ammonium andzthe like salts of diethyldithiophosphoric acid, isoprcpyl ethyl dithiophosphoric acid, didodecyl dithiophosphoric acid, di butyl dithiophosphoric acid, diphenylethyl dithiophosphoric acid, (di-(methylcyclohexyl) dithiophosphoricacid, di-(2-ethylhexyl)dithiophosphoric acid, dicetyldithiophosphonic acid, di-Lorol-B dithiophosphoric'acid (where Lorol-B compounds are derived from Lorol-B alco hol which is a commercial mixture of higher alcohols commonly derived from coconut oil and having from 8 to 18 carbon atoms per molecule), di(butyl mercapto) dithiophosphoric acid, and the like.
The particular compound selected will'depend largely on the concentrations used and the specific properties to be improved in various hydrocarbon products. In addition to their antioxidant properties, the dithiophosphate derivatives will sometimes be especially valuable for imparting mild extreme pressure properties to gear oils and the like. The dithioester dithiopho'sphate derivatives will generally be preferred for cutting oils where high sulfur concentrations are desired. I
Sufficient salt of the acid'is reacted with the tin halide compound to replace the halogen substantially completely. A typical reaction is represented by the following formula:
Thus from 1 to 2 mols of the desired dithiophosphate radical will be used for tin compounds having from 1 to 2 atoms of halogen although it may be desired to use excess salt in order to insure complete reaction. In carrying out the reaction, the salt may be added relatively slowly to the tin halide with care being taken to prevent excessive temperature rise as a result of the exothermic reaction which takes place. The reactants may be heated together for a period of from about 0.5 to 2 hours, depending on the types of materials present. Preferably, the reaction temperatures are maintained in a range of about 10 to 100 C. Conveniently, the reaction is carried out in the presence of an inert solvent in which the halide reaction by-products are insoluble or from which such by-products may be readily removed. Such solvents include petroleum ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, acetone, dioxane and the like. The heating step may be carried out under refluxing conditions when a solvent is used. The resulting metal halide will generally precipitate out of solution and may be removed by filtration, decantation or by other means. Solvent may be removed from the finished product by stripping with nitrogen or other inert gas, by distillation or by other means. A desired method for producing a relatively pure product is to filter the material, preferably before solvent is removed, through a diatomaceous filter aid such as Hy-flo."
If the products of the present invention are added to a mineral oil for inhibiting oxidation and preventing corrosion of metal parts and the like, they are preferably used in proportions of about 0.01 to 5% or by weight based on the total composition. A preferred range is from about 0.1 to 2% by Weight. Concentrations up to as high as or even higher may be used for extreme pressure lubricants, cutting oils, and the like. It is usually preferred, when marketing the additive commercially and especially when intended for use in lubricating oils, to prepare a concentrated lubricating oil solution in which the amount of additive in the composition ranges from about 20 to 50% or up to 75% by weight, depending on the solubility of the additive in the oil. The concentrate is then conveniently transported and stored in such form and may be subsequently blended with a base lubricant in the required amount before being used as a crank case oil or the like.
The invention will be more fully understood by reference to the following examples. It is pointed out, however, that the examples are given for the purpose of illustration only and are not to be construed as limiting the scope of the present invention in any Way.
EXAMPLE I.PREPARATION OF PRODUCTS Product A.Dilauryltindi-(diisopropyldithiophosphate) A mixture of 26.4 g. dilauryltindichloride (0.05 mol), 25.2 g. potassium diisopropyl dithiophosphate (0.1 mol) and 250 ml. of petroleum ether was stirred at room temperature for two hours in a S-necked 1 liter flask equipped with a thermometer and reflux condenser. The reaction mixture was then heated at reflux (50 C.) for two hours followed by filtration, whereupon 7.5 g. of ciystalline white precipitate was obtained (theoretical for KCl=7.4 g.). The filtrate was poured into an evaporating dish and placed on the steam bath to remove the solvent. A viscous, light brown liquid was obtained which analyzed 6.6% P, 14.2% S, and 12.4% Sn.
Product B.Dibutyltindi-(dimethylcyclohexyldithiophosphate) This preparation was carried out as described in connection with Product A, using 18.2 g. dibutyltindichloride (0.06 mol) and 43.2 g. potassium dimethylcyclohexyl dithiophosphate (0.12 mol). A viscous, yellow oil was obtained which analyzed 6.7% P, 13.2% S, and 8.8% Sn.
Product C.--Dibutyltindi-(dioctylphenyldithiophosphate) This reaction was conducted as described in connection with Product A, using 15.2 g. dibutyltindichloride (0.05 mol) and 54.4 g. potassium-dioctylphenyldithiophosphate (0.1 mol). A brown waxy solid was obtained which, upon analysis was found to contain 3.0% P, 5.3% S, and 4.5% Sn.
EXAMPLE II Laboratory bearing corrosion test A blend was prepared containing 0.25% by weight of the products prepared as described in Example I using as the base oil a solvent extracted, parafiinic type mineral lubricating oil of S. A. E.-20 viscosity grade. Samples of these blends and a sample of the unblended base oil were submitted to a laboratory test designed to measure the effectiveness of the additive in inhibiting the corrosiveness of a typical mineral lubricating oil towards the surfaces of copper-lead bearings. The test was carried out substantially as described in Example 12 of U. S. Patent No. 2,529,303 to McDermott. The results are reported in the table below as Bearing Corrosion Life which shows the number of hours required for the -4a Bearing Corrosion Lite (Hours to lose mg. per 25 sq. cm. of Cu- Pb bearing) Product in Base Oil (0.25 wt. percent active ingredient) The additives of the present invention may be used in various lubricating oil base stocks derived from pctroleum distillates and residuals refined by conventional means. Hydrogenated oils or white oils may be employed as well as synthetic oils prepared by polymerization of olefins, by reaction of oxides of carbon with hydrogen, or by hydrogenation of coal. The products may also be used in the synthetic polyether and polyestertype lubricants and the like as such or blended with mineral lubricants. The lubricants will usually range from about 35 to seconds (Saybolt) viscosity at 210 F.
Other agents may of course be employed in the oil compositions, such agents including dyes, pour point depressants, sludge dispersers, thickeners, viscosity index improvers, oiliness agents, and the like. In addition to being employed in lubricants, the additives of the present invention may also be used in other mineral oil products such as motor fuels, heating oils, hydraulic fluids, cutting oils, turbine oils, transformer oils, gear lubricants, greases and other products containing mineral oils as ingredients.
What is claimed is:
1. A mineral oil product having incorporated therein in the range of about 0.01 to 20% by weight of an organo tetravalent tin compound of the formula wherein Z is selected from the class consisting of oxygen and sulfur, and R and R represent hydrocarbon radicals having 1 to 20 carbon atoms.
2. A composition as in claim 1 wherein said oil product is a lubricating oil.
3. A composition as in claim 1 in which R is an alkyl radical.
4. A composition as in claim 1 wherein the R groups are alkyl radicals.
5. A composition as in claim 1 wherein the R groups are alkaryl radicals.
6. A mineral lubricating oil composition containing dissolved therein in the range of 0.1 to 2% by weight, based on the total composition, of dilauryltindi-(diisopropyldithiophosphate) 7. A mineral lubricating oil composition containing dissolved therein in the range of 0.1 to 2% by weight, based on the total composition, of dibutyltindi-(dimethylcyclohexyldithiophosphate) 8. A mineral lubricating oil composition containing dissolved therein in the range of 0.1 to 2% by weight, based'on the total composition, of dibutyltindi-(dioctylphenyldithiophosphate) 9. A concentrate consisting essentially of a hydrocarbon oil and about 20 to 50% by weight based on said concentrate of an organo-tetravalent tin compound of the formula wherein Z is selected from the class consisting of oxygen and sulfur, and R and R represent hydrocarbon radicals having 1 to 20 carbon atoms.
References Cited in the file of this patent OTHER REFERENCES Lowy et al.: Introduction to Organic Chemistry, 6th edition, page 213.
Claims (1)
1. A MINERAL OIL PRODUCT HAVING INCORPORATED THEREIN IN THE RANGE OF ABOUT 0.01 TO 20% BY WEIGHT OF AN ORGANOTETRAVALENT TIN COMPOUND OF THE FORMULA
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US381512A US2786812A (en) | 1953-09-21 | 1953-09-21 | Mineral oil compositions containing tincontaining dithiophosphate compounds |
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US381512A US2786812A (en) | 1953-09-21 | 1953-09-21 | Mineral oil compositions containing tincontaining dithiophosphate compounds |
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Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3055925A (en) * | 1960-05-12 | 1962-09-25 | Gulf Research Development Co | Alkyl lead phosphates |
US3149093A (en) * | 1958-09-23 | 1964-09-15 | Argus Chem | Stabilizing polypropylene |
US3358006A (en) * | 1962-08-28 | 1967-12-12 | Stauffer Chemical Co | Organotin dithiophosphates |
US3410797A (en) * | 1964-11-13 | 1968-11-12 | Exxon Research Engineering Co | Drilling muds |
FR2162341A1 (en) * | 1971-12-10 | 1973-07-20 | Stauffer Chemical Co | |
US3919418A (en) * | 1972-10-02 | 1975-11-11 | Stauffer Chemical Co | Methods of killing insects and mites using certain phosphorus containing organotin compounds |
US3947481A (en) * | 1972-10-02 | 1976-03-30 | Stauffer Chemical Company | Organotin miticidal and insecticidal compounds |
US4071545A (en) * | 1975-10-02 | 1978-01-31 | Stauffer Chemical Company | Preparation of S-tricyclohexyltin-O,O-diisopropyl dithiophosphate |
US4581373A (en) * | 1983-01-19 | 1986-04-08 | The Dow Chemical Company | Derivatives of biologically active substituted tin compounds, emulsifiable concentrates of said derivatives and method of controlling plant infestations |
US5092908A (en) * | 1990-06-28 | 1992-03-03 | Exxon Research And Engineering Company | Composition for improving cold flow properties of middle distillates (OP-3571) |
US5258130A (en) * | 1992-10-30 | 1993-11-02 | Mobil Oil Corporation | Antioxidant and antiwear additives for lubricants and fuels |
US5525248A (en) * | 1991-01-30 | 1996-06-11 | Mobil Oil Corporation | Antioxidants and antiwear additives for lubricants |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2365938A (en) * | 1941-10-17 | 1944-12-26 | American Cyanamid Co | Wax substituted diaryl dithiophosphoric acids and salts thereof |
US2476037A (en) * | 1945-04-05 | 1949-07-12 | Socony Vacuum Oil Co Inc | Wax-substituted diaryl dithiophosphoric acids and salts thereof |
US2630436A (en) * | 1949-05-21 | 1953-03-03 | Metal & Thermit Corp | Organotin phosphates |
-
1953
- 1953-09-21 US US381512A patent/US2786812A/en not_active Expired - Lifetime
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2365938A (en) * | 1941-10-17 | 1944-12-26 | American Cyanamid Co | Wax substituted diaryl dithiophosphoric acids and salts thereof |
US2476037A (en) * | 1945-04-05 | 1949-07-12 | Socony Vacuum Oil Co Inc | Wax-substituted diaryl dithiophosphoric acids and salts thereof |
US2630436A (en) * | 1949-05-21 | 1953-03-03 | Metal & Thermit Corp | Organotin phosphates |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3149093A (en) * | 1958-09-23 | 1964-09-15 | Argus Chem | Stabilizing polypropylene |
US3055925A (en) * | 1960-05-12 | 1962-09-25 | Gulf Research Development Co | Alkyl lead phosphates |
US3358006A (en) * | 1962-08-28 | 1967-12-12 | Stauffer Chemical Co | Organotin dithiophosphates |
US3410797A (en) * | 1964-11-13 | 1968-11-12 | Exxon Research Engineering Co | Drilling muds |
FR2162341A1 (en) * | 1971-12-10 | 1973-07-20 | Stauffer Chemical Co | |
US3919418A (en) * | 1972-10-02 | 1975-11-11 | Stauffer Chemical Co | Methods of killing insects and mites using certain phosphorus containing organotin compounds |
US3947481A (en) * | 1972-10-02 | 1976-03-30 | Stauffer Chemical Company | Organotin miticidal and insecticidal compounds |
US4071545A (en) * | 1975-10-02 | 1978-01-31 | Stauffer Chemical Company | Preparation of S-tricyclohexyltin-O,O-diisopropyl dithiophosphate |
US4581373A (en) * | 1983-01-19 | 1986-04-08 | The Dow Chemical Company | Derivatives of biologically active substituted tin compounds, emulsifiable concentrates of said derivatives and method of controlling plant infestations |
US5092908A (en) * | 1990-06-28 | 1992-03-03 | Exxon Research And Engineering Company | Composition for improving cold flow properties of middle distillates (OP-3571) |
US5525248A (en) * | 1991-01-30 | 1996-06-11 | Mobil Oil Corporation | Antioxidants and antiwear additives for lubricants |
US5258130A (en) * | 1992-10-30 | 1993-11-02 | Mobil Oil Corporation | Antioxidant and antiwear additives for lubricants and fuels |
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