US3112271A - Liquid hydrocarbon composition - Google Patents
Liquid hydrocarbon composition Download PDFInfo
- Publication number
- US3112271A US3112271A US805686A US80568659A US3112271A US 3112271 A US3112271 A US 3112271A US 805686 A US805686 A US 805686A US 80568659 A US80568659 A US 80568659A US 3112271 A US3112271 A US 3112271A
- Authority
- US
- United States
- Prior art keywords
- acid
- oil
- oils
- additive
- lubricating 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
Links
- 239000000203 mixture Substances 0.000 title claims description 29
- 229930195733 hydrocarbon Natural products 0.000 title description 9
- 150000002430 hydrocarbons Chemical class 0.000 title description 9
- 239000004215 Carbon black (E152) Substances 0.000 title description 8
- 239000007788 liquid Substances 0.000 title description 5
- 239000010687 lubricating oil Substances 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 11
- -1 aryl pho-sphites Chemical class 0.000 description 28
- 239000000654 additive Substances 0.000 description 21
- 239000003921 oil Substances 0.000 description 21
- 230000000996 additive effect Effects 0.000 description 14
- 239000002253 acid Substances 0.000 description 12
- MOFCYHDQWIZKMY-UHFFFAOYSA-N chloromethylphosphonic acid Chemical compound OP(O)(=O)CCl MOFCYHDQWIZKMY-UHFFFAOYSA-N 0.000 description 7
- ARRDXFYXBCFIAI-UHFFFAOYSA-N decylsulfanylmethylphosphonic acid Chemical compound C(CCCCCCCCC)SCP(O)(O)=O ARRDXFYXBCFIAI-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000002480 mineral oil Substances 0.000 description 7
- 235000010446 mineral oil Nutrition 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 230000001476 alcoholic effect Effects 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000010688 mineral lubricating oil Substances 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000295 fuel oil Substances 0.000 description 3
- 239000003502 gasoline Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 235000021313 oleic acid Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 description 2
- MVWGPENDPGDDOO-UHFFFAOYSA-N C(CCCCCCCCCCC)SCP(O)(O)=O Chemical compound C(CCCCCCCCCCC)SCP(O)(O)=O MVWGPENDPGDDOO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- JPIROWHTPUZLPV-UHFFFAOYSA-N phenylsulfanylmethylphosphonic acid Chemical compound OP(O)(=O)CSC1=CC=CC=C1 JPIROWHTPUZLPV-UHFFFAOYSA-N 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LSGPZYLAHPLSBS-UHFFFAOYSA-N 1-[butoxy(chloromethyl)phosphoryl]oxybutane Chemical compound CCCCOP(=O)(CCl)OCCCC LSGPZYLAHPLSBS-UHFFFAOYSA-N 0.000 description 1
- CHJJBUJCUJHDIJ-UHFFFAOYSA-N 1-chloropentylphosphonic acid Chemical class C(CCC)C(P(O)(=O)O)Cl CHJJBUJCUJHDIJ-UHFFFAOYSA-N 0.000 description 1
- KTZUJACCHDUECE-UHFFFAOYSA-N 1-chloroundecylphosphonic acid Chemical compound C(CCCCCCCCC)C(P(O)(=O)O)Cl KTZUJACCHDUECE-UHFFFAOYSA-N 0.000 description 1
- CWTHQOPTQAZCJV-UHFFFAOYSA-N 10-phenyldecane-1-thiol Chemical compound SCCCCCCCCCCC1=CC=CC=C1 CWTHQOPTQAZCJV-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FLPSWUXKDMMXBJ-UHFFFAOYSA-N [chloromethyl(cyclohexyloxy)phosphoryl]oxycyclohexane Chemical compound ClCP(OC1CCCCC1)(OC1CCCCC1)=O FLPSWUXKDMMXBJ-UHFFFAOYSA-N 0.000 description 1
- YFLPIZLPODNMOC-UHFFFAOYSA-N [chloromethyl(phenylmethoxy)phosphoryl]oxymethylbenzene Chemical compound C=1C=CC=CC=1COP(=O)(CCl)OCC1=CC=CC=C1 YFLPIZLPODNMOC-UHFFFAOYSA-N 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- LAYURVHZIIBYAP-UHFFFAOYSA-N benzylsulfanylmethylphosphonic acid Chemical compound OP(O)(=O)CSCC1=CC=CC=C1 LAYURVHZIIBYAP-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001787 chalcogens Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- CMKBCTPCXZNQKX-UHFFFAOYSA-N cyclohexanethiol Chemical compound SC1CCCCC1 CMKBCTPCXZNQKX-UHFFFAOYSA-N 0.000 description 1
- VTXVGVNLYGSIAR-UHFFFAOYSA-N decane-1-thiol Chemical compound CCCCCCCCCCS VTXVGVNLYGSIAR-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid ester group Chemical group C(CCCCCCCCCCC)(=O)O POULHZVOKOAJMA-UHFFFAOYSA-N 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
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000010720 hydraulic oil Substances 0.000 description 1
- XAKRTGZVYPZHCO-UHFFFAOYSA-O hydroxy-methoxy-oxophosphanium Chemical compound CO[P+](O)=O XAKRTGZVYPZHCO-UHFFFAOYSA-O 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000010699 lard oil Substances 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- GMTCPFCMAHMEMT-UHFFFAOYSA-N n-decyldecan-1-amine Chemical compound CCCCCCCCCCNCCCCCCCCCC GMTCPFCMAHMEMT-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical class CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 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
- 150000002889 oleic acids Chemical class 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 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
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- 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
- C10L1/2608—Organic compounds containing phosphorus containing a phosphorus-carbon bond
-
- 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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/12—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond
- C10M137/14—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond containing sulfur
-
- 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
- C10L1/2608—Organic compounds containing phosphorus containing a phosphorus-carbon bond
- C10L1/2616—Organic compounds containing phosphorus containing a phosphorus-carbon bond sulfur containing
-
- 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
- C10L1/2608—Organic compounds containing phosphorus containing a phosphorus-carbon bond
- C10L1/2625—Organic compounds containing phosphorus containing a phosphorus-carbon bond amine salts
-
- 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
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/10—Compounds containing silicon
- C10M2201/102—Silicates
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
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- C10M2219/088—Neutral salts
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Definitions
- acids and polyhydric alcohols or alkyl or aryl pho-sphites or phosphates or free fatty acids and sulfur derivatives thereof such as C1043 fatty acids (oleic or stearic acids) and sulfurized unsaturated fatty acids, e.g., sulfun'zed oleic acid.
- these compounds when used in liquid hydrocarbons, such as lubricating oil compositions which are subjected to high temperatures and pressures break down and fail to impart their expected desired properties under these extreme conditions.
- liquid hydrocarbon compositions are improved with respect to stability, wear inhibition and extreme pressure properties and contribute to minimizing octane requirement increase when used in an internal combustion engine, and the like by incorporating therein a minor amount of an oil-soluble Z-thiaalkyl phosphorus-containing compound having the general formula:
- R is an oil-soluble hydrocarbyl group, such as an alkyl, aryl, aralkyl, alkaryl or cycloalkyl radical having at least 6 and preferably a straight-chain alkyl radical having from to 18 carbon atoms, the Rfs are thesame or different groups selected from hydrogen, hydrocarbyl,
- alkyl portion of the molecule be C1048 alkyl CHR -S-CH and wherein R is hydrogen or a short alkyl radical of 1-4 carbon atoms,
- A is an aliphatic amine, preferably a primary or secondary amine, such as C primary straight chain amines, e.g., octylamine, laurylamine,
- stearylamine etc.
- branched chain primary aliphatic amines e.g., t-C alkylamine, such as t-C H N'l-l t-C1 H 5NH t0 t-C 5H3LNH2 01' t-C12H 5NH2 t0 t-C H LNH or C 1 secondary aliphatic amines, such as diamylamine, di-Z-ethylhexylamine, didecylamine, etc.
- the Z-thiaalkylphosphonic compounds are prepared by reacting a mercaptan or mercaptide having at least 6 carbon atoms with a halomethylphosphono compound such as chloromethylphosphonic acid or chloromethylphosphonate or their thioderivatives in a suitable solvent, such as an aqueous alcoholic solution, at reflux temperature and under inert conditions until the reaction is completed which normally requires from 1 to about 5 days.
- a suitable solvent such as an aqueous alcoholic solution
- the mercaptans include aliphatic mercaptans, such as hexyl, octyl, decyl, dodecyl, octadecyl mercaptans, cycloalkyl mercaptans, such as cyclohexyl mercaptan, dicyclohexyl mercaptan, aralkyl mercaptan; such as phenyldecyl mercaptan, benzyl mercaptan and the like.
- the mercaptides can be used such as the alkali metal (Na or K) mercaptides of the above compounds.
- Suitable halomethylphosphonic compounds inelude chloromethylphosphonic acid, mono or dihydrocarbyl chloromethylphosphonates, e.g., mono or dibutyl chloromethylphosphonate, mono or di-Z-ethylhexyl chloromethylphosphonate, mono or dilauryl ohloromethylphosphonate, mono or diphenyl :chloromethylphosphonate, mono or dicyclohexyl chloromethylphosphonate, mono or dibenzyl chloromethylphosphonate, dibutyl dithiochloromethylphosphonate, diphenyl chloromethyl dithiophosphonate, dibutyl chloromethyl-trithiophosphonate, alkali metal salts such as Na and K salts of chloromethylphosphonic acid, Na and K salts of monobutyl chloromethylphosphonic acid, Na and K salt of monodecyl chloromethylphosphonic acid and the like.
- alkali metal salts such as Na and K salts of chlor
- a preferred method of making the Z-thiaalkylphosphonates is to react a suitable mercapto compound, such as an alkali metal (Na or K) C1048 alkyl mercaptide with an alkali metal (Na or K) salt of chloromethylphosphonic acid in an alcoholic solution under reflux conditions and under an inert atmosphere to form the alkali metal salt of an a1kylmercaptomethylphosphonic acid.
- a strong acid such as hydrochloric acid to spring the free alkylmercaptomethylphosphonic acid, which can be converted into desired partial or full esters or polyvalent metal salts or amine salts for use as oil, fuel and grease additives as well as other uses.
- Di-Z-ethylhexylamine salt of decylmercaptomethylphosphonic acid was prepared by reacting the product of Example I with di-2-ethylhexylamine in an amount sufficient to completely neutralize both acid groups, at about 50 C. in an alcoholic solution and thereafter recovering the amine salt from the alcoholic solution.
- the additives of this invention are believed to be novel compounds. They are oil-soluble and can be used in amounts of from about 0.1% to about 25%, preferably from about 0.5% to about 5.0% by weight.
- Mercaptomethylphosphono compounds of this invention are outstanding additives for various liquid hydrocarbon products, such as natural and synthetic hydrocarbon lubricating oils, greases, fuels (gasoline, kerosene, gas oil, burner fuel oil), asphalts, waxes, slushing oils, industrial oils, e.g., metal working and drawing oils, quenching oils, textile oils, hydraulic oils, dielectric compositions and other industrial oils. They are particularly outstanding when added in small amounts to lubricating oils and lubricating compositions to impart extreme pressure and anti-wear properties to such materials. Also, these additives are useful additives for gasoline, fuel oils, and other light oil products.
- Lubricating oils useful for the preparation of compositions of this invention can be one or more of a variety of synthetic oils or natural hydrocarbon oils having a viscosity range of from 50 SUS at 100 F. to 250 SUS at 210 F. (SAE viscosity number ranging from SAE W to SAE 90).
- the natural hydrocarbon oils can be obtained from parafiinic naphthenic, asphaltic or mixed base crudes, and/or mixtures thereof.
- Synthetic oils include polymerized olefins, alkylated aromatics, isomerized waxes, copolymers of alkylene glycols and alkylene oxides (Ucon fluids) which are described in U.S.
- Patents 2,425,755, 2,425,845 and 2,774,733 such as Ucon 50HB170, Ucon 50HB660 or Ucon LB550X and which are copolymers of ethylene and 1,2-propylene oxides, the mono and diols, as well as their ester derivatives; organic esters of aliphatic dibasic acids such as di-2-ethylhexyl sebacate or di-Z-ethylhexyl adipate and the like.
- the hydrocarbon oils may be blended with fixed oils such as castor oil, lard oil and the like and/or synthetic oils as mentioned or silicone polymers and the like.
- Two typical oils A and B are paratfinic and naphthenic in character, respectively, having the following properties:
- Suitable oils are the gas turbine lube oils having the following properties:
- Example II additive 1 SAE 30 mineral oil Balance Composition F:
- Example I additive 5 Ucon 50HB660 (polyethylene-propylene glycol having a SUS viscosity at F. of 660) Balance Composition 1:
- Example I additive 2 Di-Z-ethylhexyl sebacate Balance Composition J
- Example I additive 01 Fuel oil (No. 2) Balance were:
- compositions were also tested for stability in the Dornt oxidation test described in the Natural Petroleum News, September 17, 1941, pages 2946, under the following conditions: 302 F., iron catalyst, mineral white oil base and additive amount in each example was about 1% by weight and the results are shown in Table II.
- n-Decylmercaptomethylphosphonic acid 140 n-C ioH21SCH2 1 (OH) 2)
- 2-Ethylhexylmercaptomethylphosphonic acid 80 O CHaC1-I2CH2CH2CHCH2SCH2%-(OH)2) (52H!)
- n-Decylmercaptoethylphosphonic acid 14 The mercaptomethylphosphono compounds of this invention are useful also for providing superior load-carrying properties for lubricating oils which contain minor amounts of other agents, such as silicone anti-foaming agents, alkylphenol anti-oxidants, polyacrylate ester viscosity-index improvers, long chain fatty acids such as lauric and oleic acids, oiliness agents and the like.
- a lubricating oil composition comprising a major amount of lubricating oil and a minor amount, sufiicient to impart extreme pressure properties to the lubricating oil, of an oil-soluble alkylmercaptomethylphosphono compound having the general formula wherein R is a C -C saturated alkyl radical, the R s are selected independently from the group consisting of hydrogen, and C -C saturated alkyl radical.
- a lubricating oil composition consisting essentially of a major amount of mineral lubricating oil and from about 0.1% to about 5% of a C1048 alkylmercaptomethylphosphonic acid.
- a lubricating oil composition consisting essentially of a major amount of mineral lubricating oil and from about 0.1% to about 5% of an ester of C1048 alkylmercaptomethylphosphonic acid.
- a lubricating oil composition consisting essentially of a major amount of mineral lubricating oil and from about 0.1% to about 5% of decylmercaptomethylphosphonic acid.
- a lubricating oil composition consisting essentially a major amount of mineral lubricating oil and from about 0.1% to about 5% of an ester of decylmercaptomethylphosphonic acid.
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Description
United States Patent 3,112,271 LIQUID HYDROCARBON COMPOSITION George M. Calhoun, Berkeley, Calif., assignor to Shell Oil Company, New York, N'.Y;, a corporation of Delaware No Drawing. Filed Apr. 13, 1959, Ser. No. 805,686 5 Claims. (Cl. 25246.6)
acids and polyhydric alcohols or alkyl or aryl pho-sphites or phosphates, or free fatty acids and sulfur derivatives thereof such as C1043 fatty acids (oleic or stearic acids) and sulfurized unsaturated fatty acids, e.g., sulfun'zed oleic acid. However, these compounds when used in liquid hydrocarbons, such as lubricating oil compositions which are subjected to high temperatures and pressures break down and fail to impart their expected desired properties under these extreme conditions.
It has now been discovered that liquid hydrocarbon compositions are improved with respect to stability, wear inhibition and extreme pressure properties and contribute to minimizing octane requirement increase when used in an internal combustion engine, and the like by incorporating therein a minor amount of an oil-soluble Z-thiaalkyl phosphorus-containing compound having the general formula:
XRI (I) wherein R is an oil-soluble hydrocarbyl group, such as an alkyl, aryl, aralkyl, alkaryl or cycloalkyl radical having at least 6 and preferably a straight-chain alkyl radical having from to 18 carbon atoms, the Rfs are thesame or different groups selected from hydrogen, hydrocarbyl,
or amine, preferably an alkylamine and the Xs are independently chalcogen atoms having an atomic number of from 8 to 16, such as oxygen or sulfur. Preferred compounds of the general Formula I have the following formula:
0 OH 10-18 alkyl-s-om-i or the amine sals thereof represented-by 0 OH-(A) 010-18 a1kyl-SCHr--P 011 (III) 0 OH-(A) Cloalkyl-SCH2-i and of the above formulas it is preferred that the alkyl portion of the molecule be C1048 alkyl CHR -S-CH and wherein R is hydrogen or a short alkyl radical of 1-4 carbon atoms, A is an aliphatic amine, preferably a primary or secondary amine, such as C primary straight chain amines, e.g., octylamine, laurylamine,
3,112,271 Patented Nov. 26, 1963 stearylamine, etc., or branched chain primary aliphatic amines, e.g., t-C alkylamine, such as t-C H N'l-l t-C1 H 5NH t0 t-C 5H3LNH2 01' t-C12H 5NH2 t0 t-C H LNH or C 1 secondary aliphatic amines, such as diamylamine, di-Z-ethylhexylamine, didecylamine, etc.
The Z-thiaalkylphosphonic compounds are prepared by reacting a mercaptan or mercaptide having at least 6 carbon atoms with a halomethylphosphono compound such as chloromethylphosphonic acid or chloromethylphosphonate or their thioderivatives in a suitable solvent, such as an aqueous alcoholic solution, at reflux temperature and under inert conditions until the reaction is completed which normally requires from 1 to about 5 days. The mercaptans include aliphatic mercaptans, such as hexyl, octyl, decyl, dodecyl, octadecyl mercaptans, cycloalkyl mercaptans, such as cyclohexyl mercaptan, dicyclohexyl mercaptan, aralkyl mercaptan; such as phenyldecyl mercaptan, benzyl mercaptan and the like. Instead. of the mercaptans, the mercaptides can be used such as the alkali metal (Na or K) mercaptides of the above compounds. Suitable halomethylphosphonic compounds inelude chloromethylphosphonic acid, mono or dihydrocarbyl chloromethylphosphonates, e.g., mono or dibutyl chloromethylphosphonate, mono or di-Z-ethylhexyl chloromethylphosphonate, mono or dilauryl ohloromethylphosphonate, mono or diphenyl :chloromethylphosphonate, mono or dicyclohexyl chloromethylphosphonate, mono or dibenzyl chloromethylphosphonate, dibutyl dithiochloromethylphosphonate, diphenyl chloromethyl dithiophosphonate, dibutyl chloromethyl-trithiophosphonate, alkali metal salts such as Na and K salts of chloromethylphosphonic acid, Na and K salts of monobutyl chloromethylphosphonic acid, Na and K salt of monodecyl chloromethylphosphonic acid and the like.
A preferred method of making the Z-thiaalkylphosphonates is to react a suitable mercapto compound, such as an alkali metal (Na or K) C1048 alkyl mercaptide with an alkali metal (Na or K) salt of chloromethylphosphonic acid in an alcoholic solution under reflux conditions and under an inert atmosphere to form the alkali metal salt of an a1kylmercaptomethylphosphonic acid. The salt is then treated with a strong acid such as hydrochloric acid to spring the free alkylmercaptomethylphosphonic acid, which can be converted into desired partial or full esters or polyvalent metal salts or amine salts for use as oil, fuel and grease additives as well as other uses.
The following examples illustrate the preparation of additives for use in accordance with the present invention.
EXAMPLE I Per- Per- Per- Per- Equiv Equiv.
cent cent cent cent Wt. 1st Wt. Both 0 H S P Hydrogen Hydrogens Found 49.1 9.4 12.0 11.2 261 132 Expected.-. 49.2 9.4 11.94 11.54 268.3 134.1
EXAMPLE -II The procedure of Example I was followed except'that potassium salt of phenylmercaptan was used instead of potassium salt of decylmercaptan and the final product was phenylmercaptomethylphosphonic acid.
3 EXAMPLE III The dibutyl ester of decylmercaptomethylphosphonic acid of Example I was prepared by treating decylmercaptomethylphosphonic acid with butyl alcohol in an alcoholic solution at about 60 and extracting the ester with ether.
EXAMPLE IV Di-Z-ethylhexylamine salt of decylmercaptomethylphosphonic acid (Z-thiadodecylphosphonic acid) was prepared by reacting the product of Example I with di-2-ethylhexylamine in an amount sufficient to completely neutralize both acid groups, at about 50 C. in an alcoholic solution and thereafter recovering the amine salt from the alcoholic solution.
EXAMPLE V Following the procedure of Example IV, the tert-octadecylamine salt of decylmercaptomethylphosphonic acid was prepared using tertoctadecylamine, available commercially under the trade-name of Primene IM-R, instead of di-2-ethylhexylamine.
The following additional compounds were prepared: octylmercaptomethylphosphonic acid, dodecylmercaptomethylphosphonic acid, cyclohexylmercaptomethylphosphonic acid, benzylmercaptomethylphosphonic acid, phenylmercaptomethylphosphonic acid, dibutyl decylmercaptomethylphosphonate, phenyldecylmercaptomethyl acid phosphonate, dithiobutyl dodecylmercaptomethylphosphonate, dibutyl phenylmercaptomethylphosphonate, dithiooctyl cyclohexylmercaptomethylthiophosphonate, dioctylamine dodecylmercaptomethylphosphonate, dioctadecylamine phenylmercaptomethylphosphonate, tert-octa decylamine dodecylmercaptomethylphosphonate and mixtures thereof.
The additives of this invention are believed to be novel compounds. They are oil-soluble and can be used in amounts of from about 0.1% to about 25%, preferably from about 0.5% to about 5.0% by weight.
Mercaptomethylphosphono compounds of this invention are outstanding additives for various liquid hydrocarbon products, such as natural and synthetic hydrocarbon lubricating oils, greases, fuels (gasoline, kerosene, gas oil, burner fuel oil), asphalts, waxes, slushing oils, industrial oils, e.g., metal working and drawing oils, quenching oils, textile oils, hydraulic oils, dielectric compositions and other industrial oils. They are particularly outstanding when added in small amounts to lubricating oils and lubricating compositions to impart extreme pressure and anti-wear properties to such materials. Also, these additives are useful additives for gasoline, fuel oils, and other light oil products.
Lubricating oils useful for the preparation of compositions of this invention can be one or more of a variety of synthetic oils or natural hydrocarbon oils having a viscosity range of from 50 SUS at 100 F. to 250 SUS at 210 F. (SAE viscosity number ranging from SAE W to SAE 90). The natural hydrocarbon oils can be obtained from parafiinic naphthenic, asphaltic or mixed base crudes, and/or mixtures thereof. Synthetic oils include polymerized olefins, alkylated aromatics, isomerized waxes, copolymers of alkylene glycols and alkylene oxides (Ucon fluids) which are described in U.S. Patents 2,425,755, 2,425,845 and 2,774,733 such as Ucon 50HB170, Ucon 50HB660 or Ucon LB550X and which are copolymers of ethylene and 1,2-propylene oxides, the mono and diols, as well as their ester derivatives; organic esters of aliphatic dibasic acids such as di-2-ethylhexyl sebacate or di-Z-ethylhexyl adipate and the like. The hydrocarbon oils may be blended with fixed oils such as castor oil, lard oil and the like and/or synthetic oils as mentioned or silicone polymers and the like. Two typical oils A and B are paratfinic and naphthenic in character, respectively, having the following properties:
Other suitable oils are the gas turbine lube oils having the following properties:
Grade 1010 1065 Flash, 000, F 300 465 Four, F -10 0 Viscosity, SUS at 100 F 59. 4 530 Neutral Number 0. 02 0. 01. A h None None The following compositions are illustrative of the invention, the percentages being by weight, of the indicated additive or additives with the remainder being essentially the base.
Percent Composition A:
Example I additive 2 1010 mineral oil Balance Composition B:
Example II additive 2 1010 mineral oil Balance Composition C:
Example III additive 2 1010 mineral oil Balance Composition D:
Example IV additive 2 1010 mineral oil Balance Composition E:
Example II additive 1 SAE 30 mineral oil Balance Composition F:
Example I additive 2 SAE mineral oil Balance Composition G:
Example I additive 2 Laurie acid 2 SAE 90 mineral oil Balance Composition H:
Example I additive 5 Ucon 50HB660 (polyethylene-propylene glycol having a SUS viscosity at F. of 660) Balance Composition 1:
Example I additive 2 Di-Z-ethylhexyl sebacate Balance Composition J Example I additive 1 Leaded gasoline (3 cc. of TEL) Balance Composition K:
Example I additive 01 Fuel oil (No. 2) Balance were:
Speed .p.m 3200 Oil temperature C 100 Oil flow-rate cc./scc 10 Load in increments 5 min. at each setting.
Results of the evaluations are given in Table I and for the purpose of comparison, the results obtained from the use of the base oil alone and with other known extreme pressure compositions are also given.
The following compositions were also tested for stability in the Dornt oxidation test described in the Natural Petroleum News, September 17, 1941, pages 2946, under the following conditions: 302 F., iron catalyst, mineral white oil base and additive amount in each example was about 1% by weight and the results are shown in Table II.
Table II Additive Induction period (hrs) (1) n-Decylmercaptomethylphosphonic acid 140 (n-C ioH21SCH2 1 (OH) 2) (2) 2-Ethylhexylmercaptomethylphosphonic acid 80 O (CHaC1-I2CH2CH2CHCH2SCH2%-(OH)2) (52H!) (3) n-Decylmercaptoethylphosphonic acid 14 The mercaptomethylphosphono compounds of this invention are useful also for providing superior load-carrying properties for lubricating oils which contain minor amounts of other agents, such as silicone anti-foaming agents, alkylphenol anti-oxidants, polyacrylate ester viscosity-index improvers, long chain fatty acids such as lauric and oleic acids, oiliness agents and the like.
I claim as my invention:
1. A lubricating oil composition comprising a major amount of lubricating oil and a minor amount, sufiicient to impart extreme pressure properties to the lubricating oil, of an oil-soluble alkylmercaptomethylphosphono compound having the general formula wherein R is a C -C saturated alkyl radical, the R s are selected independently from the group consisting of hydrogen, and C -C saturated alkyl radical.
2. A lubricating oil composition consisting essentially of a major amount of mineral lubricating oil and from about 0.1% to about 5% of a C1048 alkylmercaptomethylphosphonic acid.
3. A lubricating oil composition consisting essentially of a major amount of mineral lubricating oil and from about 0.1% to about 5% of an ester of C1048 alkylmercaptomethylphosphonic acid.
4. A lubricating oil composition consisting essentially of a major amount of mineral lubricating oil and from about 0.1% to about 5% of decylmercaptomethylphosphonic acid.
5. A lubricating oil composition consisting essentially a major amount of mineral lubricating oil and from about 0.1% to about 5% of an ester of decylmercaptomethylphosphonic acid.
References Cited in the file of this patent UNITED STATES PATENTS 2,346,155 Denison et al Apr. 11, 1944 2,391,099 McNab et al Dec. 18, 1945 2,535,174 Tawney Dec. 26, 1950 2,689,220 Mulvany Sept. 14, 1954 2,724,718 Stiles et al Nov. 22, 1955 2,737,492 Beegle et a1. Mar. 6, 1956 2,857,305 Birum Oct. 21, 1958 2,881,201 Schrader Apr. 7, 1959 2,971,019 Ladd et a1. Feb. 7, 1961 FOREIGN PATENTS 751,755 Great Britain July 4, 1956 804,141 Great Britain Nov. 12, 1958 OTHER REFERENCES Arbuzov et al.: Syntheses of Some Phosphone Sulfides and Phosphone Silfones, in J. Gen. Chem, U.S.S.R. 27, pages 2419-21, September 1957.
Claims (1)
1. A LUBRICATING OIL COMPOSITION COMPRISING A MAJOR AMOUNT OF LUBRICATING OIL AND A MINOR AMOUNT, SUFFICIENT TO IMPART EXTREME PRESSURE PROPERTIES TO THE LUBRICATING OIL, OF AN OIL-SOLUBLE ALKYLMERCAPTOMETHYLPHOSPHONO COMPOUND HAVING THE GENERAL FORMULA
Priority Applications (20)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE611851D BE611851A (en) | 1959-04-13 | ||
NL272803D NL272803A (en) | 1959-04-13 | ||
NL287245D NL287245A (en) | 1959-04-13 | ||
NL272804D NL272804A (en) | 1959-04-13 | ||
NL109943D NL109943C (en) | 1959-04-13 | ||
NL250415D NL250415A (en) | 1959-04-13 | ||
BE626579D BE626579A (en) | 1959-04-13 | ||
US805686A US3112271A (en) | 1959-04-13 | 1959-04-13 | Liquid hydrocarbon composition |
GB12814/60A GB904968A (en) | 1959-04-13 | 1960-04-11 | Mercaptomethyl phosphono compounds and compositions containing them |
DES68011A DE1151085B (en) | 1959-04-13 | 1960-04-11 | Lubricant mixture |
FR824022A FR1253771A (en) | 1959-04-13 | 1960-04-11 | Hydrocarbylmercaptomethylphosphono compounds and compositions containing them |
FR882716A FR81903E (en) | 1959-04-13 | 1961-12-21 | Hydrocarbylmercaptomethyl-phosphono compounds and compositions containing them |
GB45905/61A GB955357A (en) | 1959-04-13 | 1961-12-21 | Organophosphorus-substituted dimethyl disulphides, and lubricant and fuel compositions containing the same |
GB45909/61A GB1010536A (en) | 1959-04-13 | 1961-12-21 | Organic phosphonic compounds useful as fuel and lubricant additives, and compositions containing organic phosphonic compounds |
FR882715A FR81706E (en) | 1959-04-13 | 1961-12-21 | Hydrocarbylmercaptomethylphosphono compounds and compositions containing them |
FR919847A FR83758E (en) | 1959-04-13 | 1962-12-27 | Hydrocarbylmercaptomethyl-phosphono compounds and compositions containing them |
GB48702/62A GB957772A (en) | 1959-04-13 | 1962-12-27 | Polythiahydrocarbylphosphono compounds and compositions containing them |
US305809A US3198826A (en) | 1959-04-13 | 1963-08-30 | Alkyl mercaptomethylphosphonic acids |
US312329A US3316332A (en) | 1959-04-13 | 1963-09-30 | Sulfoxy alkyl phosphono compounds |
US472663A US3309428A (en) | 1959-04-13 | 1965-07-16 | Oil-soluble bis(methylphosphonodisulfides |
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US805686A US3112271A (en) | 1959-04-13 | 1959-04-13 | Liquid hydrocarbon composition |
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US3197497A (en) * | 1962-03-16 | 1965-07-27 | Monsanto Co | Allenic phosphorus derivatives |
US3205252A (en) * | 1963-03-26 | 1965-09-07 | Socony Mobil Oil Co Inc | Thiophosphonous acid ester insecticides |
US3223754A (en) * | 1959-12-04 | 1965-12-14 | Bayer Ag | Alkyl mercapto alkyl esters of substituted phosphonic acids |
US3226322A (en) * | 1961-12-28 | 1965-12-28 | Shell Oil Co | Liquid hydrocarbon composition and additives therefor |
US3235628A (en) * | 1959-12-14 | 1966-02-15 | Shell Oil Co | 2-thiaphosphono compounds |
US3305610A (en) * | 1963-07-02 | 1967-02-21 | Stauffer Chemical Co | Phosphonodithioates as pesticides |
US3326749A (en) * | 1963-07-05 | 1967-06-20 | Monsanto Co | Alkylphosphonothioates |
US3485918A (en) * | 1966-06-24 | 1969-12-23 | Chemagro Corp | Nematocidal method using alkylthioalkylphosphonodithioates |
US5244591A (en) * | 1992-03-23 | 1993-09-14 | Chevron Research And Technology Company | Lubricating oil compositions for internal combustion engines having silver bearing parts |
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US3485918A (en) * | 1966-06-24 | 1969-12-23 | Chemagro Corp | Nematocidal method using alkylthioalkylphosphonodithioates |
US5244591A (en) * | 1992-03-23 | 1993-09-14 | Chevron Research And Technology Company | Lubricating oil compositions for internal combustion engines having silver bearing parts |
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