GB774119A - Complex alkoxy metal salts of organic acids and lubricating and fuel compositions thereof - Google Patents
Complex alkoxy metal salts of organic acids and lubricating and fuel compositions thereofInfo
- Publication number
- GB774119A GB774119A GB6896/54A GB689654A GB774119A GB 774119 A GB774119 A GB 774119A GB 6896/54 A GB6896/54 A GB 6896/54A GB 689654 A GB689654 A GB 689654A GB 774119 A GB774119 A GB 774119A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- acids
- methoxy
- complex
- salt
- 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
Links
- 229910052751 metal Inorganic materials 0.000 title abstract 11
- 239000002184 metal Substances 0.000 title abstract 11
- 150000007524 organic acids Chemical class 0.000 title abstract 9
- 150000003839 salts Chemical class 0.000 title abstract 6
- 125000003545 alkoxy group Chemical group 0.000 title abstract 4
- 239000000203 mixture Substances 0.000 title abstract 4
- 235000005985 organic acids Nutrition 0.000 title abstract 4
- 239000000446 fuel Substances 0.000 title 1
- 230000001050 lubricating effect Effects 0.000 title 1
- 239000011777 magnesium Substances 0.000 abstract 18
- 229910052749 magnesium Inorganic materials 0.000 abstract 18
- 239000002253 acid Substances 0.000 abstract 16
- 150000007513 acids Chemical class 0.000 abstract 13
- 239000001993 wax Substances 0.000 abstract 12
- 229910052788 barium Inorganic materials 0.000 abstract 9
- 125000000217 alkyl group Chemical group 0.000 abstract 8
- 239000011575 calcium Substances 0.000 abstract 8
- 229910052791 calcium Inorganic materials 0.000 abstract 8
- 125000004432 carbon atom Chemical group C* 0.000 abstract 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 7
- -1 light naphtha Substances 0.000 abstract 6
- 239000002480 mineral oil Substances 0.000 abstract 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 5
- 235000010446 mineral oil Nutrition 0.000 abstract 5
- 239000011734 sodium Substances 0.000 abstract 5
- 229910052708 sodium Inorganic materials 0.000 abstract 5
- 229910052725 zinc Inorganic materials 0.000 abstract 5
- 239000011701 zinc Substances 0.000 abstract 5
- VSIIELBPDODZGZ-UHFFFAOYSA-N (2-dodecylphenyl) dihydrogen phosphate Chemical compound CCCCCCCCCCCCC1=CC=CC=C1OP(O)(O)=O VSIIELBPDODZGZ-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 4
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 abstract 4
- CQJXEKPVUKTVBG-UHFFFAOYSA-N dihydroxy-phenylsulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound OP(O)(=S)SC1=CC=CC=C1 CQJXEKPVUKTVBG-UHFFFAOYSA-N 0.000 abstract 4
- 239000003208 petroleum Substances 0.000 abstract 4
- 239000011591 potassium Substances 0.000 abstract 4
- 229910052700 potassium Inorganic materials 0.000 abstract 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 3
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- 238000002360 preparation method Methods 0.000 abstract 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 3
- 239000003784 tall oil Substances 0.000 abstract 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 2
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 abstract 2
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 abstract 2
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Substances 0.000 abstract 2
- QCJQWJKKTGJDCM-UHFFFAOYSA-N [P].[S] Chemical compound [P].[S] QCJQWJKKTGJDCM-UHFFFAOYSA-N 0.000 abstract 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000001735 carboxylic acids Chemical class 0.000 abstract 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract 2
- 239000012141 concentrate Substances 0.000 abstract 2
- 239000003599 detergent Substances 0.000 abstract 2
- 239000003502 gasoline Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 239000003350 kerosene Substances 0.000 abstract 2
- 239000010687 lubricating oil Substances 0.000 abstract 2
- 150000004780 naphthols Chemical class 0.000 abstract 2
- 239000012188 paraffin wax Substances 0.000 abstract 2
- 150000007965 phenolic acids Chemical class 0.000 abstract 2
- 235000009048 phenolic acids Nutrition 0.000 abstract 2
- 150000002989 phenols Chemical class 0.000 abstract 2
- 239000011574 phosphorus Substances 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- 150000003232 pyrogallols Chemical class 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 229910052712 strontium Inorganic materials 0.000 abstract 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract 2
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 abstract 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 abstract 1
- MKJMXPFTCHYBRV-UHFFFAOYSA-N 2-hexadecylbenzene-1,4-diol Chemical compound CCCCCCCCCCCCCCCCC1=CC(O)=CC=C1O MKJMXPFTCHYBRV-UHFFFAOYSA-N 0.000 abstract 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical class CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 abstract 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Chemical class CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 abstract 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Chemical class C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 abstract 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 abstract 1
- RYSXDTSXRRSZRO-UHFFFAOYSA-N C(CCCCCCCCCCC)OP(OCCCCCCCCCCCC)=S Chemical compound C(CCCCCCCCCCC)OP(OCCCCCCCCCCCC)=S RYSXDTSXRRSZRO-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- HVWGGPRWKSHASF-UHFFFAOYSA-N Sulfuric acid, monooctadecyl ester Chemical compound CCCCCCCCCCCCCCCCCCOS(O)(=O)=O HVWGGPRWKSHASF-UHFFFAOYSA-N 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 239000003963 antioxidant agent Substances 0.000 abstract 1
- 239000013556 antirust agent Substances 0.000 abstract 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 abstract 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 abstract 1
- 150000001559 benzoic acids Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 abstract 1
- XJTHNMNVQBJKND-UHFFFAOYSA-N dihexadecylphosphinic acid Chemical compound CCCCCCCCCCCCCCCCP(O)(=O)CCCCCCCCCCCCCCCC XJTHNMNVQBJKND-UHFFFAOYSA-N 0.000 abstract 1
- KUFDFOXPFQCUST-UHFFFAOYSA-N dipentylphosphinic acid Chemical compound CCCCCP(O)(=O)CCCCC KUFDFOXPFQCUST-UHFFFAOYSA-N 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000000295 fuel oil Substances 0.000 abstract 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 abstract 1
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical class CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000010688 mineral lubricating oil Substances 0.000 abstract 1
- FTMKAMVLFVRZQX-UHFFFAOYSA-N octadecylphosphonic acid Chemical compound CCCCCCCCCCCCCCCCCCP(O)(O)=O FTMKAMVLFVRZQX-UHFFFAOYSA-N 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 1
- 150000003022 phthalic acids Chemical class 0.000 abstract 1
- RLEFZEWKMQQZOA-UHFFFAOYSA-M potassium;octanoate Chemical compound [K+].CCCCCCCC([O-])=O RLEFZEWKMQQZOA-UHFFFAOYSA-M 0.000 abstract 1
- 150000003870 salicylic acids Chemical class 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 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
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/26—Organic compounds containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/414—Preparation of superbasic salts
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/418—Preparation of metal complexes containing carboxylic acid moieties
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
-
- 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/30—Organic compounds compounds not mentioned before (complexes)
- C10L1/301—Organic compounds compounds not mentioned before (complexes) derived from metals
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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
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/025—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with condensed rings
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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
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/027—Neutral salts thereof
-
- 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
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty 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
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
- C10M2207/128—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids containing hydroxy groups; Ethers thereof
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- 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
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
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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
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/141—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings monocarboxylic
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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
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/142—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings polycarboxylic
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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
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/144—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings containing hydroxy 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/146—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings having carboxyl groups bound to carbon atoms of six-membeered aromatic rings having a hydrocarbon substituent of thirty or more carbon atoms
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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
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/16—Naphthenic 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
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/18—Tall oil 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/042—Sulfate esters
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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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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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
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
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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
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
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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
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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
- C10M2223/061—Metal salts
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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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Lubricants (AREA)
- Liquid Carbonaceous Fuels (AREA)
Abstract
Complex alkoxy metal salts are prepared by heating an oil-soluble organic acid with an alcoholate of a metal of Group I or II derived from a monohydroxy saturated aliphatic alcohol having from 1 to 20 carbon atoms in a proportion such as to supply to the reaction between 2 and 6 equivalents of metal alcoholate based on the equivalent of the acid-hydrogen content of the organic acid. The complex salts derived from organic acids other than sulphonic acids are novel. The reaction is conducted by heating together a solution of the organic acid in a solvent such as a mineral lubricating oil, light naphtha, kerosene, toluene or xylene, and an alcohol solution of the metal alcoholate at 50-200 DEG C., preferably 120-175 DEG C., for one to six hours, the temperature used being sufficient to effect the removal of the excess alcohol without removing the solvent. The organic acids include aliphatic carboxylic acids having 10-24 carbon atoms such as decanoic, lauric, stearic, oleic, linoleic and arachidic acids; the aromatic and naphthenic carboxylic acids having an aliphatic substituent containing 10-24 carbon atoms, such as alkyl-substituted benzoic, salicylic and phthalic acids, and abietic acid; phenolic acids, such as alkyl-substituted phenols, naphthols, resorcinols, catechols, hydroquinols and pyrogallols wherein the alkyl portion contains at least 10 carbon atoms, e.g. wax phenol, dinonyl catechol, and hexadecyl hydroquinone; organic phosphorus-containing acids, such as alkyl, alkaryl and aralkyl-substituted phosphoric, phosphonic and phosphinic acids, e.g. dodecyl phenyl phosphoric acid, octadecyl phosphonic acid and diamyl phosphinic acid; organic sulphur-containing acids, such as alkyl, alkaryl and aralkyl-substituted sulphonic acids and alkyl sulphuric acids, e.g. dodecyl phenyl sulphonic acid, wax benzene sulphonic acid, petroleum sulphonic acid and octadecyl sulphuric acid; organic phosphorus- and sulphur-containing acids, such as alkyl, alkaryl and aralkyl-substituted thiophosphoric, thiophosphonic and thiophosphinic acids, e.g. wax phenyl dithiophosphoric acid, didodecyl thiophosphonic acid and dihexadecyl phosphinic acid. The metal alcoholates used include those of potassium, sodium, calcium, strontium, barium, zinc and magnesium, such as sodium methylate, calcium methylate, barium methylate, magnesium methylate, calcium butylate, potassium caprylate, barium decylate, calcium dodecylate, magnesium tetradecylate, zinc hexadecylate, and magnesium octadecylate. Detailed examples are given of the preparation of complex magnesium methoxy salts of tall oil acid, a complex calcium methoxy salt of tall oil acid, complex zinc methoxy salts, a complex barium methoxy salt and a complex magnesium methoxy salt of naphthenic acid, a complex magnesium methoxy salt of wax phenol, a complex sodium butoxy salt of wax phenol, a complex magnesium methoxy salt of wax-b -naphthol, a complex barium methoxy salt of petroleum sulphonic acid, a complex barium methoxy, complex calcium methoxy, complex sodium methoxy, complex magnesium methoxy, and complex potassium butoxy salts of wax benzene sulphonic acids, a complex magnesium methoxy salt of dodecylphenyl phosphoric acid and a complex magnesium methoxy salt of wax phenyl dithiophosphoric acid. The complex salts may be used as additives for petroleum oil fractions (see Group III) and in the manufacture of detergents and dispersants. The preparation of the following intermediates is described in detail: Wax phenol. A C20-C24 paraffin wax is chlorinated and then reacted with phenol in the presence of aluminium chloride. Wax-benzene sulphonic acid. A C24 paraffin wax is chlorinated then reacted with benzene in the presence of aluminium chloride to form a wax-benzene which is then sulphonated with oleum and the product is blended with a mineral oil. Dodecylphenyl phosphoric acid. Dodecylphenol is heated with phosphorus pentoxide at 150 DEG C. for 3 hours. Wax phenyl dithiophosphoric acid. An oil blend containing a wax phenol and a mineral oil is stirred with phosphorus pentasulphide at 170 DEG C. for 5 hours.ALSO:Mineral oil compositions contain a minor proportion of a complex alkoxy metal salt prepared by heating an oil-soluble organic acid with an alcoholate of a metal of Group I or II derived from a monohydroxy saturated aliphatic alcohol having 1 to 20 carbon atoms, in a proportion such as to supply to the reaction between 2 and 6 equivalents of metal alcoholate based on the equivalent of the acid hydrogen of the organic acid. The mineral oil may be a lubricating oil, a fuel oil or a gasoline. Suitable organic acids are aliphatic carboxylic acids having 10-24 carbon atoms; aromatic or naphthenic carboxylic acids having an aliphatic substituent containing 10-24 carbon atoms; phenolic acids, such as alkyl-substituted phenols, naphthols, resorcinols, catechols, hydroquinols and pyrogallols wherein the alkyl position contains at least 10 carbon atoms; organic phosphorus-containing acids, such as alkyl, alkaryl-and aralkyl-substituted phosphoric, phosphonic and phosphinic acids; organic sulphur-containing acids such as alkyl, alkaryl- and aralkyl-substituted sulphonic acids and alkyl sulphuric acids; and organic phosphorus-and sulphur-containing acids, such as alkyl-, alkaryl- and aralkyl-substituted thiophosphoric, thiophosphonic and thiophosphinic acids. The metal may be sodium, potassium, calcium, strontium, barium, magnesium or zinc. Detailed examples describe the preparation of blends of kerosene or solvent-refined mineral oil containing magnesium methoxy salts or calcium methoxy salts of tall oil; zinc methoxy salts, barium methoxy salts, or magnesium methoxy salts of naphthenic acid; a magnesium methoxy salt or sodium butoxy salt of wax phenol; a magnesium methoxy salt of waxb -naphthol; a barium methoxy salt of petroleum sulphonic acid; a barium methoxy sodium methoxy salt, magnesium methoxy salt or potassium butoxy salt of wax-benzene sulphonic acid; a magnesium methoxy salt of dodecylphenyl phosphoric acid; or a magnesium methoxy salt of wax phenyl dithiophosphoric acid. Concentrates containing 20 to 50 per cent of complex alkoxy metal salt thus prepared are effective in concentrates ranging from 0.01 per cent as anti-rust agents in gasoline, and in concentrations ranging from 0.5 to 2.0 per cent as antioxidants and detergents in lubricating oils. The mineral oils may also contain viscosity index improvers, extreme pressure agents, and pour point depressants.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US348117A US2851417A (en) | 1953-04-10 | 1953-04-10 | Complex alkoxy metal salts of organic acids and lubricating and fuel compositions thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
GB774119A true GB774119A (en) | 1957-05-08 |
Family
ID=23366710
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB6896/54A Expired GB774119A (en) | 1953-04-10 | 1954-03-09 | Complex alkoxy metal salts of organic acids and lubricating and fuel compositions thereof |
Country Status (2)
Country | Link |
---|---|
US (1) | US2851417A (en) |
GB (1) | GB774119A (en) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3021280A (en) * | 1956-12-17 | 1962-02-13 | Continental Oil Co | Method of dispersing barium hydroxide in a non-volatile carrier |
US3088815A (en) * | 1958-03-27 | 1963-05-07 | Sinclair Research Inc | Fuel oil |
US3014868A (en) * | 1958-04-24 | 1961-12-26 | Socony Mobil Oil Co Inc | Lubricating oil compositions containing complex metal salts of alkylphenolaldehyde condensation products |
US3061419A (en) * | 1958-10-02 | 1962-10-30 | Continental Oil Co | Fuel additive for jet propulsion engines |
GB897672A (en) * | 1959-01-14 | 1962-05-30 | British Petroleum Co | Improvements relating to fuels for internal combustion piston engines and to the operation of such engines |
US3264075A (en) * | 1962-07-06 | 1966-08-02 | Mobil Oil Corp | Metal salts of succinamic acids in distillate fuel oil |
US3320042A (en) * | 1962-11-21 | 1967-05-16 | Sun Oil Co | Color stable fuel oil |
US3406115A (en) * | 1965-04-02 | 1968-10-15 | Dow Chemical Co | Method of lessening friction in moving oil-base liquids |
US3471403A (en) * | 1967-03-07 | 1969-10-07 | Lubrizol Corp | Basic metal carboxylate complex |
US3635686A (en) * | 1969-05-19 | 1972-01-18 | Mobil Oil Corp | Mineral oil compositions metal alkyl ester tetrapropenylsuccinates |
US3791804A (en) * | 1969-10-10 | 1974-02-12 | Standard Oil Co | Fuel and lubricating oil additives transition metal complexes |
US3791805A (en) * | 1969-10-10 | 1974-02-12 | Standard Oil Co | Transition metal complexes as fuel and motor oil additives |
US3856688A (en) * | 1972-07-25 | 1974-12-24 | Us Agriculture | Ether-containing dibasic fatty acid metal soap thickened greases |
US5290825A (en) * | 1985-05-17 | 1994-03-01 | Lazar Warren G | Composition and method for inhibiting the cure of cyanoacrylate adhesives and cure inhibited cyanoacrylate adhesive compositions |
US5266080A (en) * | 1989-10-11 | 1993-11-30 | The Standard Oil Company | Methanol fuel containing flame luminosity agent |
US5800731A (en) * | 1991-11-28 | 1998-09-01 | Rwe-Dea Aktiengesellschaft Fur Mineraloel Und Chemie | Homogeneous electroviscous fluids using aluminum compounds |
CN1368540A (en) * | 2001-02-01 | 2002-09-11 | 呼世滨 | Anti-explosion additive of gasoline and gasoline prepared from it |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2113243A (en) * | 1935-09-25 | 1938-04-05 | Du Pont | Production of abietic alcohol |
US2225197A (en) * | 1939-05-15 | 1940-12-17 | Stanger Bert Allen | Addition and stabilizer agent for lubricating oils and hydrocarbon liquids |
US2469041A (en) * | 1946-09-02 | 1949-05-03 | Standard Vacuum Oil Company | Methods for preparing aluminum soaps and certain classes of useful compositions containing aluminum soaps |
US2528803A (en) * | 1947-08-01 | 1950-11-07 | Harshaw Chem Corp | Preparation of metallic soaps |
US2585520A (en) * | 1948-12-03 | 1952-02-12 | Shell Dev | Lubricating compositions containing highly basic metal sulfonates |
US2610982A (en) * | 1950-02-11 | 1952-09-16 | Texas Co | Manufacture of magnesium salts of high molecular weight alkylated hydroxy aromatic copounds and their use in lubricating oils |
US2582833A (en) * | 1950-07-12 | 1952-01-15 | Sherwin Williams Co | Method for the preparation of aluminum and magnesium soaps |
-
1953
- 1953-04-10 US US348117A patent/US2851417A/en not_active Expired - Lifetime
-
1954
- 1954-03-09 GB GB6896/54A patent/GB774119A/en not_active Expired
Also Published As
Publication number | Publication date |
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US2851417A (en) | 1958-09-09 |
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