US3294500A - Fuel for internal combustion engines - Google Patents
Fuel for internal combustion engines Download PDFInfo
- Publication number
- US3294500A US3294500A US168801A US16880162A US3294500A US 3294500 A US3294500 A US 3294500A US 168801 A US168801 A US 168801A US 16880162 A US16880162 A US 16880162A US 3294500 A US3294500 A US 3294500A
- Authority
- US
- United States
- Prior art keywords
- acid
- ester
- fuel
- dicarboxylic
- phosphonic
- 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
- 239000000446 fuel Substances 0.000 title claims description 36
- 238000002485 combustion reaction Methods 0.000 title claims description 12
- 239000000203 mixture Substances 0.000 claims description 38
- 239000000654 additive Substances 0.000 claims description 15
- 230000000996 additive effect Effects 0.000 claims description 13
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 11
- 230000007935 neutral effect Effects 0.000 claims description 8
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 6
- 150000003008 phosphonic acid esters Chemical class 0.000 claims description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 6
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 4
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 description 17
- -1 diphenyl dicarboxylic acid Chemical compound 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 10
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 7
- 235000011037 adipic acid Nutrition 0.000 description 6
- 239000001361 adipic acid Substances 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- OOMQAYMCTYABQN-UHFFFAOYSA-N 1-chloro-2-dibutoxyphosphorylbenzene Chemical compound CCCCOP(=O)(OCCCC)C1=CC=CC=C1Cl OOMQAYMCTYABQN-UHFFFAOYSA-N 0.000 description 2
- WCJLOEFXANROAO-UHFFFAOYSA-N CCCCOP(O)=O Chemical compound CCCCOP(O)=O WCJLOEFXANROAO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 239000002283 diesel fuel Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- PSFDQSOCUJVVGF-UHFFFAOYSA-N harman Chemical compound C12=CC=CC=C2NC2=C1C=CN=C2C PSFDQSOCUJVVGF-UHFFFAOYSA-N 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 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 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001400 nonyl 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])[H] 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229940116254 phosphonic acid Drugs 0.000 description 2
- 150000003009 phosphonic acids Chemical class 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003254 radicals Chemical group 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- HJONNNXQWUWENQ-UHFFFAOYSA-N (2-ethylphenyl)phosphonic acid Chemical compound CCC1=CC=CC=C1P(O)(O)=O HJONNNXQWUWENQ-UHFFFAOYSA-N 0.000 description 1
- RBSXHDIPCIWOMG-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-yl)sulfonylurea Chemical compound CCS(=O)(=O)C=1N=C2C=CC=CN2C=1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 RBSXHDIPCIWOMG-UHFFFAOYSA-N 0.000 description 1
- QJGNSTCICFBACB-UHFFFAOYSA-N 2-octylpropanedioic acid Chemical compound CCCCCCCCC(C(O)=O)C(O)=O QJGNSTCICFBACB-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- FBBCDCFCZPFWJP-UHFFFAOYSA-N P(OC1=C(C=CC=C1)Cl)(OC1=C(C=CC=C1)Cl)=O Chemical compound P(OC1=C(C=CC=C1)Cl)(OC1=C(C=CC=C1)Cl)=O FBBCDCFCZPFWJP-UHFFFAOYSA-N 0.000 description 1
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 1
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- PPKCVUUJHQNTLW-UHFFFAOYSA-N chlorooxy(phenyl)phosphinic acid Chemical group ClOP(=O)(O)C1=CC=CC=C1 PPKCVUUJHQNTLW-UHFFFAOYSA-N 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- FBSFTJQYCLLGKH-UHFFFAOYSA-N cyclohexylphosphonic acid Chemical compound OP(O)(=O)C1CCCCC1 FBSFTJQYCLLGKH-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
- 230000007547 defect Effects 0.000 description 1
- OSPSWZSRKYCQPF-UHFFFAOYSA-N dibutoxy(oxo)phosphanium Chemical compound CCCCO[P+](=O)OCCCC OSPSWZSRKYCQPF-UHFFFAOYSA-N 0.000 description 1
- SVMUEEINWGBIPD-UHFFFAOYSA-N dodecylphosphonic acid Chemical compound CCCCCCCCCCCCP(O)(O)=O SVMUEEINWGBIPD-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 125000003106 haloaryl group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- YOOYVODKUBZAPO-UHFFFAOYSA-N naphthalen-1-ylphosphonic acid Chemical compound C1=CC=C2C(P(O)(=O)O)=CC=CC2=C1 YOOYVODKUBZAPO-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000376 reactant Substances 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
- 125000003944 tolyl group Chemical group 0.000 description 1
Classifications
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- 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
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
-
- 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
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- 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
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- 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
- C10L1/18—Organic compounds containing oxygen
- C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
- C10L1/1905—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polycarboxylic acids
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- 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
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/284—Esters of aromatic monocarboxylic acids
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/285—Esters of aromatic polycarboxylic acids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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- 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
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
- C10M2211/044—Acids; Salts or esters thereof
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- 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
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/06—Perfluorinated compounds
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/044—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms having cycloaliphatic groups
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
- C10M2215/26—Amines
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
-
- 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
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
- C10N2040/26—Two-strokes or two-cycle engines
-
- 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
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
- F02B3/00—Engines characterised by air compression and subsequent fuel addition
- F02B3/06—Engines characterised by air compression and subsequent fuel addition with compression ignition
Definitions
- the present invention refers to a new composition of matter; more particularly, it concerns a new composition which contains a fuel for combustion engines and mixtures of neutral esters of polycarboxylic and of phosphonic acids.
- the acids on which the esters of the polycarboxylic or phosphonic acids may be based are, for example, phthalic acid, isop-hthalic acid, terephthalic acid, trimellitic acid, naphthalene dicarboxylic acid, diphenyl dicarboxylic acid and the halogen substitution products of these acids; hexahydrophthalic acid, alkylnaphthalene dicarboxylic acids; adipic acid, pimel-ic acid, suberic acid, azelaic acid, sebacic acid, nonane dicarboxylic acid, decane dicarboxylic acid or pheny-lphos-p honic acid, its halogen and alkyl substitution products, such as for example di(chlorophenyl)phosphonic acid, di(fiuorophenyl)phosphonic acid, tolyl phosphonic acids, xylyl phosphonic acids, di(tolyl)phosp-honic acids, (eth
- the alcohols on which the esters are based may be the following, for example: metyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, octyl, nonyl, or decyl alcohols etc., stearyl alcohol, and cycl-ohexanol.
- the neutral phosphonic esters correspond to the general formula wherein R stands for alkyl or cycloalkyl, X represents alkyl, cycloalkyl, aryl, alkaryl, or halogen-substituted aryl, while Y stands for one of the aforesaid OR-radicals or X radicals.
- ester components are suitably chosen so that the boiling point of the esters is sufficiently high as to enable the ester mixtures to be used for the desired purpose without any risk of a substantial loss by evaporation or the like.
- the mixtures according to the invention When using the mixtures according to the invention in fuels for combustion engines, it is irrelevant whether the components are added to the fuels together or separately. In order to render the measuring more easy, it is also possible to dissolve the esters or their mixtures first in a mineral oil, preferably a spindle oil of low viscosity from naphthenes, and to admix this concentrate with the fuels.
- a mineral oil preferably a spindle oil of low viscosity from naphthenes
- the amounts of the ester mixture required vary within wide limits and can easily be ascertained by preliminary tests. They frequently depend on the nature of the fuels and the additives which may already be present in the fuels. In general, 1-2 parts by weight of the mixture according to the invention are sufiicient per 1000 to 100,000 parts by weight of fuel.
- the ratio of the esters of carboxylic acid to phosphon-ic acid can also be varied within Wide limits.
- a suitable ratio of the mixture is about 5 parts by weight of carboxyl-ic ester to 1 part by weight of phosphonic ester.
- basic compounds particularly amines, can be added to the fuels apart from the mixtures of the invention.
- Example 1 To 100 kg. of a normal carburetor fuel of a mixutrc of equal parts of top benzine and cracked benzine there is added a mixture of 0.005 kilogram of di(chlorophenyl)phosphonic acid-n-butyl ester, 0.025 kilogram of dibutyl phthalate and 0.170 kilogram of a mineral oil of low viscosity, a so-called spindle oil having a viscosity of about 1.5 Engler degrees at 50 C. This fuel inhibits incrustation and corrosion of the engine parts in normal LC. engines.
- Example 2 To 100 kilograms of a carburetor fuel comprising about two-thirds of top benzine and one-third of cracked benzine and 0.04 percent by volume of tetraethyl lead is added 0.01 kilogram of a mixture of parts by weight of di(chlorophenyl)iphosphonic acid-n-butyl ester and 20 parts by weight of chlorophenyl phosphonic acid dibutyl ester, 0.05 kilogram of methyl-amyl ester of adipic acid and 0.12 kilogram of a gas oil.
- This mixture particularly prevents the motor parts in two-stroke engines becoming encrusted or corroded.
- the same result is obtained by replacing the adipic acid ester by the imethyl-butyl ester of terephthalic acid as a component of the mixture.
- Example 3 A fuel for combustion engines is prepared by adding to 2500 kilograms of a normal carburetor fuel kilograms of'a so-called two-stroke oil mixed with 0.05 kilogram of chloro'phenyl phosphonic acid distearyl ester, 0.20 kilogram of di-buty l ester of sebacic acid and 0.05 kilogram of dicyclohexyl amine. By the use of this fuel many defects are cured which occur with fuels containing no ester mixtures.
- Example 4 additive mixture, said mixture consisting essentially of (1) a neutral ester of an acid selected from the group consisting of phthalic acid, isophthalic acid, terephthalic acid, diphenyl dicarboxylic acid and corresponding halodi-phenyl dicarboxylic acids, hexahydrophthalic acid, alkylnaphthalene dicarboxylic acid, adipic acid, pimelic acid, suberic acid, azclaic acid,sebacic acid,nouane dicarboxylic acid, decane dicarboxylic acid, the corresponding halo and alkyl hydrocarbon substitution products thereof with members selected from the group consisting of an alkanol and cycloalkanol, and (2) a neutral phosphonic acid ester of the formula wherein R is a member selected from the group consisting of alkyl and cycloalkyl; X is a member selected from the group consisting of alkyl, cycloalkyl,
- composition of claim 1 wherein the alcohol reactants of 1) are members selected from the group consisting of methyl, ethyl, propyl, 'butyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, stearyl, and cyclohexyl alcohols.
- composition according to claim 1 wherein the ratio of component (1) to component (2) of the additive mixture is about 4-20:1 in parts by weight.
- a fuel for internal combustion engines comprising a fuel base of a mixture of distillate benzine and cracked benzine containing an additive mixture of di(chlorphenyl) phosphonic surfaced-n-butyl ester and dibutyl phthalate, with a mineral oil, the ratio of additive mixture to fuel base being about 3:10,000 in parts by weight, and the ratio of dibutyl phthalate to di(chlorphenyl)phosphonic acid-n-butyl ester being about 5:1 in parts by weight.
- a fuel for internal combustion engines comprising a fuel base of distillate benzine and cracked benzine and an additive mixture of di(fluorophenyl) phosphonic acidn-butyl ester and dibutyl phthalate with a mineral oil, the ratio of additive mixture to fuel base being about 3: 10,000 parts by weight and the ratio of dibutyl phthalate to di(fiuorophenyl) phosphonic acid-n-butyl ester is about 5:1 parts by Weight.
- a fuel for internal combustion engines comprising a liquid fuel for an internal combustion engine consisting of distillate benzine and crack benzine and an additive mixture of di(ehlorophenyl) phosphonic acid-n-butyl ester, chlorophenyl phosphonic acid dibutyl ester and the methyl-amyl ester of adipic acid in the presence of tetraethyl lead and a gas oil, the ratio of said additive mixture to said liquid fuel being about 1:10,000 parts by weight and the ratio of adipic acid ester to the phosphonic acid ester being about 5:1 parts by weight.
- a fuel for internal combustion engines comprising a fuel base of distillate benzine and cracked benzine and an additive mixture of di(chlorophenyl) phosphonic acidn-butyl ester, ch'lorophenyl phosphonic acid dibutyl ester and the methyl-butyl ester of terephthalic acid in the presence of tetraethyl lead and a gas oil, the ratio of said additive mixture to fuel component being about 1110,000 parts by weight and the ratio of terephthalic acid ester t0 the phosphonic acid esters is about 5: 1.
- An additive mixture for fuel selected from the group consisting of carburetor fuel and diesel fuel consisting of (A) a neutral ester of a polycarboxylic acid and an alcohol selected from the group consisting of alkanol and a cycloalkanol and (B) a neutral phosphonic acid ester of the formula C
- )R 0 1lX Y wherein the ratio of (A) and (B) is about 4-2021 in parts by Weight, and, wherein R stands for a member selected from the group consisting of alkyl and cycloalkyl; X is a member selected from the group consisting of alkyl, cycloa-lkyl, aryl, alkylaryl and halogensubstituted aryl; and Y 'is a member selected from the group consisting of X, --O-alkyl, and O-cyeloalkyl.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Combustion & Propulsion (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Lubricants (AREA)
Description
United States Patent 3,294,500 FUEL FOR INTERNAL CGMBUSTION ENGINES Max Zimmermann, Leverkusen, Werner Miiller, Cologne, and Walter Hagge, Leverkusen, Germany, assignors to Farbenfabriken Bayer Aktiengesellschaft, Leverkusen, Germany, a German corporation No Drawing. Filed Jan. 25, 1962, Ser. No. 168,801 Claims priority, application Germany, May 15, 1954, F 14,727 Claims. (Cl. 44-70) v This application is a continuation-in-part application of application Serial Number 508,295, filed May 13, 1955, now abandoned.
The present invention refers to a new composition of matter; more particularly, it concerns a new composition which contains a fuel for combustion engines and mixtures of neutral esters of polycarboxylic and of phosphonic acids.
It has been found, that such mixtures have valuable properties: as additives to fuels used in combustion engines, such as carburetor fuel or diesel fuel, they are capable of protecting the exposed engine parts against corrosion and incrustation so that the engine'parts, particularly pistons, rings, grooves and the like do not prematurely wear out.
The acids on which the esters of the polycarboxylic or phosphonic acids may be based are, for example, phthalic acid, isop-hthalic acid, terephthalic acid, trimellitic acid, naphthalene dicarboxylic acid, diphenyl dicarboxylic acid and the halogen substitution products of these acids; hexahydrophthalic acid, alkylnaphthalene dicarboxylic acids; adipic acid, pimel-ic acid, suberic acid, azelaic acid, sebacic acid, nonane dicarboxylic acid, decane dicarboxylic acid or pheny-lphos-p honic acid, its halogen and alkyl substitution products, such as for example di(chlorophenyl)phosphonic acid, di(fiuorophenyl)phosphonic acid, tolyl phosphonic acids, xylyl phosphonic acids, di(tolyl)phosp-honic acids, (ethylphenyl) phosphonic acid, naphthyl phosphonic acid, alkylna-phthyl phopshonic acids, cyclohexyl phosphonic acid, dodecyl phosphonic acid, as well as phos'pihonic acids which are substituted by radicals of petroleum fractions.
The alcohols on which the esters are based may be the following, for example: metyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, octyl, nonyl, or decyl alcohols etc., stearyl alcohol, and cycl-ohexanol.
Thus, the neutral phosphonic esters correspond to the general formula wherein R stands for alkyl or cycloalkyl, X represents alkyl, cycloalkyl, aryl, alkaryl, or halogen-substituted aryl, while Y stands for one of the aforesaid OR-radicals or X radicals.
The ester components are suitably chosen so that the boiling point of the esters is sufficiently high as to enable the ester mixtures to be used for the desired purpose without any risk of a substantial loss by evaporation or the like.
When using the mixtures according to the invention in fuels for combustion engines, it is irrelevant whether the components are added to the fuels together or separately. In order to render the measuring more easy, it is also possible to dissolve the esters or their mixtures first in a mineral oil, preferably a spindle oil of low viscosity from naphthenes, and to admix this concentrate with the fuels. The amounts of the ester mixture required vary within wide limits and can easily be ascertained by preliminary tests. They frequently depend on the nature of the fuels and the additives which may already be present in the fuels. In general, 1-2 parts by weight of the mixture according to the invention are sufiicient per 1000 to 100,000 parts by weight of fuel. The ratio of the esters of carboxylic acid to phosphon-ic acid can also be varied Within Wide limits. A suitable ratio of the mixture is about 5 parts by weight of carboxyl-ic ester to 1 part by weight of phosphonic ester. Instead of individual esters there can also be applied mixtures of different esters of carboxylic acid or phosp honic acid.
If desired, basic compounds, particularly amines, can be added to the fuels apart from the mixtures of the invention.
Example 1 To 100 kg. of a normal carburetor fuel of a mixutrc of equal parts of top benzine and cracked benzine there is added a mixture of 0.005 kilogram of di(chlorophenyl)phosphonic acid-n-butyl ester, 0.025 kilogram of dibutyl phthalate and 0.170 kilogram of a mineral oil of low viscosity, a so-called spindle oil having a viscosity of about 1.5 Engler degrees at 50 C. This fuel inhibits incrustation and corrosion of the engine parts in normal LC. engines.
A mixture containing instead of di(chlorophenyl)phosphonic acid-n-butyl ester the same amount of di(fluorop henyl)phosphonic acid-n-butyl ester shows the same good results.
Example 2 To 100 kilograms of a carburetor fuel comprising about two-thirds of top benzine and one-third of cracked benzine and 0.04 percent by volume of tetraethyl lead is added 0.01 kilogram of a mixture of parts by weight of di(chlorophenyl)iphosphonic acid-n-butyl ester and 20 parts by weight of chlorophenyl phosphonic acid dibutyl ester, 0.05 kilogram of methyl-amyl ester of adipic acid and 0.12 kilogram of a gas oil.
This mixture particularly prevents the motor parts in two-stroke engines becoming encrusted or corroded. The same result is obtained by replacing the adipic acid ester by the imethyl-butyl ester of terephthalic acid as a component of the mixture.
Example 3 A fuel for combustion engines is prepared by adding to 2500 kilograms of a normal carburetor fuel kilograms of'a so-called two-stroke oil mixed with 0.05 kilogram of chloro'phenyl phosphonic acid distearyl ester, 0.20 kilogram of di-buty l ester of sebacic acid and 0.05 kilogram of dicyclohexyl amine. By the use of this fuel many defects are cured which occur with fuels containing no ester mixtures.
Example 4 .additive mixture, said mixture consisting essentially of (1) a neutral ester of an acid selected from the group consisting of phthalic acid, isophthalic acid, terephthalic acid, diphenyl dicarboxylic acid and corresponding halodi-phenyl dicarboxylic acids, hexahydrophthalic acid, alkylnaphthalene dicarboxylic acid, adipic acid, pimelic acid, suberic acid, azclaic acid,sebacic acid,nouane dicarboxylic acid, decane dicarboxylic acid, the corresponding halo and alkyl hydrocarbon substitution products thereof with members selected from the group consisting of an alkanol and cycloalkanol, and (2) a neutral phosphonic acid ester of the formula wherein R is a member selected from the group consisting of alkyl and cycloalkyl; X is a member selected from the group consisting of alkyl, cycloalkyl, aryl, alkylaryl, and haloaryl; Y is a member selected from the group consisting of alkoxy, cycloalkoxy and X, as above defined; the ratio of additive mixture to fuel being about 1-2:1000100,000.
2. The composition of claim 1 wherein the alcohol reactants of 1) are members selected from the group consisting of methyl, ethyl, propyl, 'butyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, stearyl, and cyclohexyl alcohols.
3. The composition of claim 4 in which the phosphonic acid ester is a chlorophenyl phosphonic acid ester.
4. A composition according to claim 1 wherein the ratio of component (1) to component (2) of the additive mixture is about 4-20:1 in parts by weight.
5. A fuel for combustion engines according to claim 1 wherein the ratio of component (1) to component (2) is about 4-8.5:1 parts by weight.
6. A fuel for internal combustion engines comprising a fuel base of a mixture of distillate benzine and cracked benzine containing an additive mixture of di(chlorphenyl) phosphonic aicid-n-butyl ester and dibutyl phthalate, with a mineral oil, the ratio of additive mixture to fuel base being about 3:10,000 in parts by weight, and the ratio of dibutyl phthalate to di(chlorphenyl)phosphonic acid-n-butyl ester being about 5:1 in parts by weight.
7. A fuel for internal combustion engines comprising a fuel base of distillate benzine and cracked benzine and an additive mixture of di(fluorophenyl) phosphonic acidn-butyl ester and dibutyl phthalate with a mineral oil, the ratio of additive mixture to fuel base being about 3: 10,000 parts by weight and the ratio of dibutyl phthalate to di(fiuorophenyl) phosphonic acid-n-butyl ester is about 5:1 parts by Weight.
8. A fuel for internal combustion engines comprising a liquid fuel for an internal combustion engine consisting of distillate benzine and crack benzine and an additive mixture of di(ehlorophenyl) phosphonic acid-n-butyl ester, chlorophenyl phosphonic acid dibutyl ester and the methyl-amyl ester of adipic acid in the presence of tetraethyl lead and a gas oil, the ratio of said additive mixture to said liquid fuel being about 1:10,000 parts by weight and the ratio of adipic acid ester to the phosphonic acid ester being about 5:1 parts by weight.
9. A fuel for internal combustion engines comprising a fuel base of distillate benzine and cracked benzine and an additive mixture of di(chlorophenyl) phosphonic acidn-butyl ester, ch'lorophenyl phosphonic acid dibutyl ester and the methyl-butyl ester of terephthalic acid in the presence of tetraethyl lead and a gas oil, the ratio of said additive mixture to fuel component being about 1110,000 parts by weight and the ratio of terephthalic acid ester t0 the phosphonic acid esters is about 5: 1.
10. An additive mixture for fuel selected from the group consisting of carburetor fuel and diesel fuel consisting of (A) a neutral ester of a polycarboxylic acid and an alcohol selected from the group consisting of alkanol and a cycloalkanol and (B) a neutral phosphonic acid ester of the formula C|)R 0=1lX Y wherein the ratio of (A) and (B) is about 4-2021 in parts by Weight, and, wherein R stands for a member selected from the group consisting of alkyl and cycloalkyl; X is a member selected from the group consisting of alkyl, cycloa-lkyl, aryl, alkylaryl and halogensubstituted aryl; and Y 'is a member selected from the group consisting of X, --O-alkyl, and O-cyeloalkyl.
References Cited by the Examiner UNITED STATES PATENTS 2,174,019 9/1939 Sullivan 25249.8 2,204,598 6/1940 Humphreys et al. 252396 2,215,590 9/1940 Maverick 25257 2,481,372 9/1949 Von Fuchs et a1 252498 2,485,341 10/1949 Wasson et al. 252-49.8 2,573,568 10/1951 Harman et a1 25246.7 2,843,466 7/1958 Greenwald 4470 2,897,071 7/1959 Gilbert 44-69 FOREIGN PATENTS 5/1959 Canada. 5/1954 Great Britain.
Claims (1)
1. A COMPOSITION OF MATTER CONTAINING A LIQUID FUEL FOR INTERNAL COMBUSTION ENGINES AND AN ACTIVE AMOUNT OF ADDITIVE MIXTURE, SAID MIXTURE CONSISTING ESSENTIALLY OF (1) A NEUTRAL ESTER OF AN ACID SELECTED FROM THE GROUP CONSISTING OF PHTHALIC ACID, ISOPHTHALIC ACID, TEREPHTHALIC ACID, DIPHENYL DICARBOXYLIC ACID AND CORRESPONDING HALODIPHENYL DICARBOXYLIC ACIDS, HEXAHYDROPHTHALIC ACID, ALKYLNAPHTHALENE DICARBOXYLIC ACID, ADIPHIC ACID, PIMELIC ACID, SUBERIC ACID, AZELAIC ACID, SEBACIC ACID, NONE DICARBOXYLIC ACID, DECANE DICARBOXYLIC ACID, THE CORRESPONDING HALO AND ALKYL HYDROCARBON SUBSTITUTION PRODUCTS THEREOF WITH MEMBERS SELECTED FROM THE GROUP CONSISTING OF AN ALKANOL AND CYCLOALKANOL, AND (2) A NEUTRAL PHOSPHONIC ACID ESTER OF THE FORMULA
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF14727A DE1062484B (en) | 1954-05-15 | 1954-05-15 | Additive mixture for fuels based on hydrocarbons |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3294500A true US3294500A (en) | 1966-12-27 |
Family
ID=7087685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US168801A Expired - Lifetime US3294500A (en) | 1954-05-15 | 1962-01-25 | Fuel for internal combustion engines |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3294500A (en) |
| BE (1) | BE538168A (en) |
| CH (1) | CH339778A (en) |
| DE (1) | DE1062484B (en) |
| FR (1) | FR1138286A (en) |
| GB (1) | GB793460A (en) |
| NL (2) | NL197217A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3807974A (en) * | 1970-07-24 | 1974-04-30 | Ethyl Corp | Fuels for automotive engines |
| US5004478A (en) * | 1988-11-17 | 1991-04-02 | Basf Aktiengesellschaft | Motor fuel for internal combustion engines |
| WO2002024840A1 (en) * | 2000-09-20 | 2002-03-28 | Exxonmobil Research And Engineering Company | Diesel engine lubricant composition |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1117940B (en) * | 1959-07-31 | 1961-11-23 | Socony Mobil Oil Co Inc | Fuel for jet engines and jet engines |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2174019A (en) * | 1936-11-27 | 1939-09-26 | Standard Oil Co | Lubricant |
| US2204598A (en) * | 1937-02-23 | 1940-06-18 | Standard Oil Co | Compounded lubricating oil |
| US2215590A (en) * | 1935-07-20 | 1940-09-24 | Standard Oil Dev Co | Lubricating composition |
| US2481372A (en) * | 1946-09-27 | 1949-09-06 | Shell Dev | Rust protective lubricants |
| US2485341A (en) * | 1947-10-18 | 1949-10-18 | Standard Oil Dev Co | Rust inhibiting composition |
| US2573568A (en) * | 1948-05-10 | 1951-10-30 | Shell Dev | Lubricant composition containing dialkyl trihaloalkane phosphonate as an extreme pressure agent |
| GB709471A (en) * | 1950-06-10 | 1954-05-26 | Bataafsche Petroleum | Fuels for internal combustion engines and compositions for the production of such fuels |
| US2843466A (en) * | 1957-04-19 | 1958-07-15 | Cities Service Res & Dev Co | Fuel composition |
| CA575281A (en) * | 1959-05-05 | E.I. Du Pont De Nemours And Company | Gasoline additives | |
| US2897071A (en) * | 1953-06-30 | 1959-07-28 | Ethyl Corp | Gasoline fuels |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR863630A (en) * | 1939-03-02 | 1941-04-05 | Standard Oil Dev Co | Improvements to fuel products |
| US2405560A (en) * | 1943-02-06 | 1946-08-13 | Gen Motors Corp | Fuel |
| DE825921C (en) * | 1944-03-09 | 1951-12-27 | Alexander Duckham & Company Lt | Fuel for internal combustion engines |
| US2493713A (en) * | 1946-05-21 | 1950-01-03 | Gen Aniline & Film Corp | Stabilized iron pentacarbonyl and motor fuel containing the same |
| DE855480C (en) * | 1950-01-13 | 1952-11-13 | Shell Refining & Marketing Co | Fuel for internal combustion engines |
| FR1043087A (en) * | 1950-06-10 | 1953-11-05 | Bataafsche Petroleum | Anti-fouling composition for engines |
| DE885500C (en) * | 1951-08-31 | 1953-08-06 | Josef Schaefer | Additive to diesel fuel |
-
0
- NL NL102633D patent/NL102633C/xx active
- NL NL197217D patent/NL197217A/xx unknown
- BE BE538168D patent/BE538168A/xx unknown
-
1954
- 1954-05-15 DE DEF14727A patent/DE1062484B/en active Pending
-
1955
- 1955-05-12 CH CH339778D patent/CH339778A/en unknown
- 1955-05-13 FR FR1138286D patent/FR1138286A/en not_active Expired
- 1955-05-13 GB GB13933/55A patent/GB793460A/en not_active Expired
-
1962
- 1962-01-25 US US168801A patent/US3294500A/en not_active Expired - Lifetime
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA575281A (en) * | 1959-05-05 | E.I. Du Pont De Nemours And Company | Gasoline additives | |
| US2215590A (en) * | 1935-07-20 | 1940-09-24 | Standard Oil Dev Co | Lubricating composition |
| US2174019A (en) * | 1936-11-27 | 1939-09-26 | Standard Oil Co | Lubricant |
| US2204598A (en) * | 1937-02-23 | 1940-06-18 | Standard Oil Co | Compounded lubricating oil |
| US2481372A (en) * | 1946-09-27 | 1949-09-06 | Shell Dev | Rust protective lubricants |
| US2485341A (en) * | 1947-10-18 | 1949-10-18 | Standard Oil Dev Co | Rust inhibiting composition |
| US2573568A (en) * | 1948-05-10 | 1951-10-30 | Shell Dev | Lubricant composition containing dialkyl trihaloalkane phosphonate as an extreme pressure agent |
| GB709471A (en) * | 1950-06-10 | 1954-05-26 | Bataafsche Petroleum | Fuels for internal combustion engines and compositions for the production of such fuels |
| US2897071A (en) * | 1953-06-30 | 1959-07-28 | Ethyl Corp | Gasoline fuels |
| US2843466A (en) * | 1957-04-19 | 1958-07-15 | Cities Service Res & Dev Co | Fuel composition |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3807974A (en) * | 1970-07-24 | 1974-04-30 | Ethyl Corp | Fuels for automotive engines |
| US5004478A (en) * | 1988-11-17 | 1991-04-02 | Basf Aktiengesellschaft | Motor fuel for internal combustion engines |
| WO2002024840A1 (en) * | 2000-09-20 | 2002-03-28 | Exxonmobil Research And Engineering Company | Diesel engine lubricant composition |
| JP2004510017A (en) * | 2000-09-20 | 2004-04-02 | エクソンモービル リサーチ アンド エンジニアリング カンパニー | Diesel engine lubricant composition |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1062484B (en) | 1959-07-30 |
| GB793460A (en) | 1958-04-16 |
| NL197217A (en) | |
| FR1138286A (en) | 1957-06-12 |
| BE538168A (en) | |
| CH339778A (en) | 1959-07-15 |
| NL102633C (en) |
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