US3594140A - Smoke suppressant fuel mixtures - Google Patents
Smoke suppressant fuel mixtures Download PDFInfo
- Publication number
- US3594140A US3594140A US779219A US3594140DA US3594140A US 3594140 A US3594140 A US 3594140A US 779219 A US779219 A US 779219A US 3594140D A US3594140D A US 3594140DA US 3594140 A US3594140 A US 3594140A
- Authority
- US
- United States
- Prior art keywords
- ether
- fuel
- smoke
- barium
- metal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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Classifications
-
- 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
-
- 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
- C10L10/02—Use of additives to fuels or fires for particular purposes for reducing smoke development
-
- 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
- C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
- C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
-
- 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
- C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
- C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
- C10L1/1855—Cyclic ethers, e.g. epoxides, lactides, lactones
-
- 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
- C10L1/188—Carboxylic acids; metal salts thereof
-
- 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
- C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
- C10L1/2431—Organic compounds containing sulfur, selenium and/or tellurium sulfur bond to oxygen, e.g. sulfones, sulfoxides
- C10L1/2437—Sulfonic acids; Derivatives thereof, e.g. sulfonamides, sulfosuccinic acid esters
Definitions
- a liquid fuel composition having reduced soot and smoking characteristics is formed by admixing a major proportion of a liquid hydrocarbon fuel and a minor proportion, respectively, of an ether and a Group II-A metal sulfonate wherein the concentration of Group II-A metal is from about 0.007 to 0.1% by weight.
- a preferred fuel composition comprises a diesel fuel admixed with a barium alkaryl sulfonate and an alkyl ether of an alkylene glycol, said glycol ether having from 3 to 10 carbon atoms, wherein the concentration of barium metal is from about 0.04 to 0.08% by weight.
- This invention relates to new liquid fuel compositions.
- it relates to new diesel fuel mixtures with reduced smoke and soot forming properties.
- the objects of this invention are met by dispersing or dissolving in liquid hydrocarbon fuels having a tendency decyl, eicosyl, pentacosyl, phenyl ice to form soot and smoke on combustion, a minor amount of an ether and a Group II-A metal sulfonate wherein the concentration of the Group IL-A metal is from about 0.007 to 0.1% by weight based on the total weight of the fuel mixture. Generally, the concentration of ether in the sulfonate-fuel mixture is from about 0.05 to 5% by weight.
- Mixtures of diesel fuel, an ether and a barium hydrocarbyl sulfonate have particularly significant reduced smoke and soot forming properties.
- Liquid hydrocarbon fuel mixtures having further reduced soot and smoke characteristics are obtained when glycol ethers, particularly mono or dialkyl ethers of ethylene glycol are employed.
- a particularly preferred fuel mixture is diesel fuel in admixture with from about 0.2 to 0.5% by weight of l-methoxy-Z-propanol and from about 0.04 to 0.08% by weight of barium metal present as a barium alkaryl sulfonate having a molecular weight of from about 900 to 1100.
- barium metal present as a barium alkaryl sulfonate having a molecular weight of from about 900 to 1100.
- Enhanced results are also obtained when the other is the dimethyl ether of ethylene glycol.
- a method for operating an internal combustion engine which comprises passing a liquid hydrocarbon fuel mixture of the invention through the fuel supply system to the combustion chamber of said engine and causing ignition of the fuel therein in normal fashion.
- This method of operation can be employed in operating a compression ignition engine utilizing the diesel fuel mixtures of this invention.
- the sulfonic acids from which the sulfonates employed in the present invention are formed are those having the following structural formula:
- R may be an alkyl, alkenyl, aryl, alkaryl, aralkyl or alicyclic radical.
- suitable R groups are: methyl, propyl, 2-ethylhexyl, neodecyl, dodecyl, octanaphthyl, benzyl, cresyl, ethylphenyl, phenylhexyl, cyclohexyl, cyclopropyl, butenyl, linoleyl, and the like.
- sulfonic acids employed as sulfonates are: methanesulfonic acid, decanesulfonic acid, Z-ethylhexanesulfonic acid, pentanesulfonic acid, phenylmethanesulfonic acid, decylbenzenesulfonic acid, naphthalenesulfonic acid, octenesulfonic acid, cyclohexanesulfonic acid, and the like, and mixtures thereof.
- Further mixed (unsymmetric) sulfonates may be employed to raise or lower the metal content of the fuel mixtures as desired. Mixtures of symmetric and unsymmetric sulfonates are also employed.
- Some specific sulfonates useful in this invention include:
- ethers employed in the present invention are, in general, those having the following structural formulas:
- R(OR'-)n OR" wherein n is an integer preferably between about 0 to 10 and especially between about 1 to 3; R is a hydrocarbyl radical, R" is hydrogen or hydrocarbyl radical, such that when n is a whole integer, R" is hydrogen or hydrocarbyl, and when n is zero, R" is hydrocarbyl, and R is a hydrocarbylene radical, such as methylene, ethylene or the like; and
- n is an integer preferably having the value of 1 or 2, and R and R' are hydrocarbylene radicals; Wherein the total number of carbon atoms in either molecule is preferably less than about 30.
- R and R" are hydrocarbyl radicals
- typical groups include, for instance: alkyl, alkenyl, aryl, alkaryl, aralkyl, or alicyclic radicals.
- suitable hydrocarbyl radicals are: methyl, ethyl, propyl, butyl, isohexyl, 2-ethylhexyl, neodecyl, dodecyl, octadecyl, eicosyl, nonacosyl, phenyl, naphthyl, benzyl, tolyl, ethylphenyl, phenylhexyl, cyclohexyl, cyclopropyl, cyclopentyl, butenyl, octenyl, linoleyl, etc.
- R and R' are hydrocarbylene radicals
- typical groups include, for example: alkylene, arylene, alkarylene, aralkylene, alkenylene or alicyclene radicals.
- Suitable hydrocarbylene radicals are: methylene, ethylene, propylene, isohexylene, decylene, phenylene, cyclohexylene, pentenylene, etc.
- Examples of simple ethers useful in this invention are: diethyl ether, diisopropyl ether, methyl tert-butyl ether, ethyl n-butyl ether, decyl butyl ether, nonacosyl methyl ether, allyl ethyl ether, vinyl isobutyl ether, cyclopropyl methyl ether, cyclobutyl ether, methyl ethyl ether, benzyl methyl ether, benzyl ethyl ether, phenyl ether, anisOle, bis(2-chloroisopropyl) ether, and the like.
- heterocyclic ethers useful in this invention are: such heterocyclic monoethers as tetrahydrofuran, ethylene oxide, propylene oxide, furan; such heterocyclic diethers as para-dioxane; meta-dioxane; dioxolanes; 2-(3-heptyl) 1,3-dioxolane; 2-(3-heptyl) 1,3-dioxan-5-ol; 2-(3-heptyl) l,3-dioxolane-4-methanol; and such heterocyclic triethers as symtrioxane; ethyltrioxane; and the like.
- Typical fuel mixtures of the invention include any ether, and any sulfonate, selected from the following examples, in admixture with a liquid hydrocarbon fuel.
- Ether Group II-A sulfonate Monophenyl ether of ethylene glycol.
- fuel-soluble sulfonic acids such as high molecular weight petroleum sulfonic acids, including mahogany acids.
- Naturally occurring alkaryl hydrocarbons such as those found in mixed kerosene fraction of petroleum, are suitable as the hydrocarbyl substituents of the sulfonic acids.
- These sulfonic acids may be prepared according to the processes disclosed in US. 2,395,713 and US. 2,388,677 and refined according to US. 2,387,866.
- each alkyl group of the mixed sulfonates is a linear group of from about 14 to 18 carbon atoms, said sulfonate having a molecular weight of from 800 to 1,500, preferably from 900 to 1,100.
- Examples of preferred sulfonates include:
- substituents must be essentially non-reactive to the fuel and include, for example, such polar groups as halogen, amino, nitro, nitrate, hydroxyl, and the like.
- the preferred ethers are those normally liquid mono or diethers of polyols, soluble in fuel.
- these ethers are: monomethyl ether of diethylene glycol, monoethyl ether of diethylene glycol, dimethyl ether of propylene glycol, monomethyl ether of triethylene glycol, diethyl ether of dipropylene glycol, and the like.
- Alkyl ethers of polyoxyalkylene glycols having from about 3 to 10 carbon atoms are particularly preferred.
- Especially suitable ethers are the monoalkyl ethers of glycols and in particular, of ethylene glycol such as: monoethyl ether of ethylene glycol, monopentyl ether of ethylene glycol, mono(2-ethylbutyl) ether of ethylene glycol, monopentyl ether of ethylene glycol and monopropyl ether of propylene glycol; and the dialkyl ethers of glycols and, particularly, of ethylene glycol, such as dipropyl ether of ethylene glycol, diethyl ether of ethylene glycol, and di-butyl ether of ethylene glycol.
- ethylene glycol such as: monoethyl ether of ethylene glycol, monopentyl ether of ethylene glycol, mono(2-ethylbutyl) ether of ethylene glycol, monopentyl ether of ethylene glycol and monopropyl ether of propylene glycol
- An ether producing unusually good soot and smoke reduction. in fuels in conjunction with the sulfonates of this invention is 1-methoxy-2-propanol.
- Preferred mixtures of the invention include:
- Group II-A metal sulfonates are employed in minor amounts, at least at about 0.007% by weight Group II-A metal, as a Group II-A metal sulfonate. When amounts of below about 0.007% by weight of Group II-A metal are employed, no practical smoke reductions are achieved.
- Group II-A metal present as a Group II-A metal sulfonate. If greater amounts are employed, no further substantial visible smoke and soot reductions are obtained. Also, if Group II-A metal, as sulfonate, is employed in excess of about 0.1% by weight, detrimental affects are observed in engine performance, characterized,
- Group II-A metal sulfonates especially barium alkaryl sulfonates, be employed to supply from about 0.04 to 0.08% by weight Group II-A metal.
- the ethers are utilized in amounts necessary to produce a significant reduction in the smoke and soot forming characteristics of the fuel mixture.
- generally at least about 0.05% by weight of ether is employed. Although amounts in excess of about 5% by weight may be employed, practical smoke reductions are achieved with lesser amounts.
- the ethers, and particularly allyl ethers of alkylene glycols having from about 3 to 11 carbon atoms are employed in amounts from about 0.1 to 1% by weight.
- the previous weight percents are based upon the weight of Group II-A metal or ether as compared to the total Weight of the fuel mixtures.
- the sulfonates can be dispersed in the fuel in finely divided form.
- the sulfonate is dissolved or dispersed in the fuel and thereafter the ether is added to the sulfonate-fuel mixture.
- the sulfonate may be initially dissolved or dispersed in the ether and the resulting sulfonate-ether concentrate combined with the liquid hydrocarbon fuel.
- any liquid hydrocarbon fuel including heating fuels, and particularly those fuels useful in internal combustion engines can be employed as the fuel component of the compositions of this invention. It is preferred that the liquid hydrocarbon fuel be a diesel fuel having an initial boiling point of about 300 F. and an end distillation point of about 750 F. Diesel fuels having a boiling range of from about 400 F. to about 675 R, such as No. 2 diesel fuel, are especially preferred.
- EXAMPLE I In order to evaluate the new smoke suppressant mixtures, 0.3% by weight of the dimethyl ether of ethylene glycol and 0.3% by weight of a barium alkaryl sulfonate (14.5 weight percent Ba; molecular weight about 1000) were sequentially dissolved in a diesel fuel at room temperature with mechanical stirring.
- Aromatics percent 31.0 Olefins, percent i 0 Saturates, percent 69.0
- the novel smoke suppressant mixtures were evaluated in a 4-cylinder John Deere Model 3020 tractor engine equipped with a Hartridge smoke meter. An exhaust probe was inserted in the exhaust pipe about 4 feet from the exhaust manifold. The probe was connected to a 2-way valve of the smoke meter.
- the engine was warmed up on the base fuel at a condition wherein no visible smoke was observed in the exhaust gases.
- the fuel flow was increased until it was about 22 pounds per hour, generally corresponding to the appearance of visible black smoke in the exhaust gases.
- the smoke suppressant fuel mixture of the invention was then substituted for the base fuel and the engine was run about 5 minutes to allow stabilization. The smoke meter reading was then recorded. The cycle of base fuel and additive fuel was repeated two additional times.
- results of the preceding example demonstrate the enhanced effectiveness of fuel mixtures of barium hydrocarbyl sulfonates and of alkyl ethers of ethylene glycol, and especially fuel mixtures of dimethyl ether of ethylene glycol and barium alkaryl sulfonates in reducing smoke and soot. Similar results are also obtained when other combinations of ethers and Group II-A metal sulfonates are substituted for the sulfonate and ether of the above example. Satisfactory results are obtained when other ethers such as methyl ethyl ether, diethyl ether of diethylene glycol, dioxane, and dibenzyl ether are substituted for the dimethyl ether of ethylene glycol.
- EXAMPLE II In order to further demonstrate visible smoke and soot reduction in mixtures of hydrocarbon fuels, selected quantities of the synthetic barium alkaryl sulfonate previously employed and l-methoxy-Z-propanol were admixed in the No. 2 diesel fuel of Example I and then tested in the John Deere 4 cylinder engine according to the procedure of Example I. The smoke reductions are reported in accordance with the equation of the previous example. The following table shows the results of the tests:
- the smoke reductions observed were significantly less than the above tested sulfonate-ether fuel mixtures having the same metal concentrations.
- the fuel compositions of this invention may additionally contain oxidation inhibitors, corrosion in- 8 hibitors, antifoam agents, other smoke suppressants, sludge inhibitors, color stabilizers and other additional agents adapted to improve the fuels in one or more respects.
- detergents such as metal salts of monoesters of sulfuric acid formed from aliphatic alcohols containing from 8 to 18 carbons, metal salts of di-(2-ethylhexyl)sulfosuccinic acid, and especially Group II-A salts, particularly barium salts, and mixtures thereof may be additionally incorporated to the additives.
- a fuel composition having reduced smoke and soot forming properties comprising a major proportion of a liquid hydrocarbon fuel and a minor proportion, respectively, of an alkyl ether of an alkylene glycol in which the glycol ether has up to 8 carbon atoms and a Group II-A metal sulfonate wherein the concentration of the Group II-A metal is from about 0.007 to 0.1% by weight based on the total weight of the fuel mixture.
- a fuel composition having reduced soot and smoke forming properties comprising a diesel fuel, a barium alkaryl sulfonate, and an alkyl ether of an alkylene glycol, the glycol ether having up to 8 carbon atoms, the concentration of the barium metal is from about 0.04 to 0.08% by weight, the concentration of the other is from 0.2 to 0.5% by weight and wherein the concentration of said barium and said ether are based on the total weight of the fuel mixture.
- composition of claim 6 in which the sulfonate is a barium alkaryl sulfonate having a molecular weight of from about 900 to 1100 and the ether is l-methoxy-Z- propanol.
- composition of claim 7 in which the dimethyl ether of ethylene glycol is substituted for 1-methoxy-2- propanol.
- the fuel mixture is a diesel fuel containing a barium alkaryl sulfonate having a molecular weight of from about 900 to 1100 and the ether is the dimethyl ether of ethylene glycol.
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Combustion & Propulsion (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Liquid Carbonaceous Fuels (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US77921968A | 1968-11-26 | 1968-11-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3594140A true US3594140A (en) | 1971-07-20 |
Family
ID=25115704
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US779219A Expired - Lifetime US3594140A (en) | 1968-11-26 | 1968-11-26 | Smoke suppressant fuel mixtures |
Country Status (2)
Country | Link |
---|---|
US (1) | US3594140A (de) |
GB (1) | GB1266756A (de) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4744800A (en) * | 1985-01-18 | 1988-05-17 | Nippon Oil Co., Ltd. | Gasoline compositions for automotive vehicles |
US5308365A (en) * | 1993-08-31 | 1994-05-03 | Arco Chemical Technology, L.P. | Diesel fuel |
US5314511A (en) * | 1992-12-23 | 1994-05-24 | Arco Chemical Technology, L.P. | Diesel fuel |
US5425790A (en) * | 1992-12-23 | 1995-06-20 | Arco Chemical Technology, L.P. | Diesel fuel |
WO1995025153A1 (en) * | 1994-03-16 | 1995-09-21 | Olah George A | Cleaner burning and cetane enhancing diesel fuel supplements |
US5520710A (en) * | 1993-09-29 | 1996-05-28 | George A. Olah | Cleaner burning and cetane enhancing diesel fuel supplements |
US6235068B1 (en) * | 1998-01-10 | 2001-05-22 | The Lubrizol Corporation | Fuel composition |
EP1178101A2 (de) * | 2000-08-04 | 2002-02-06 | Yoshiro Hamada | Umweltfreundlicher Brennstoff |
-
1968
- 1968-11-26 US US779219A patent/US3594140A/en not_active Expired - Lifetime
-
1969
- 1969-11-25 GB GB1266756D patent/GB1266756A/en not_active Expired
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4744800A (en) * | 1985-01-18 | 1988-05-17 | Nippon Oil Co., Ltd. | Gasoline compositions for automotive vehicles |
US5314511A (en) * | 1992-12-23 | 1994-05-24 | Arco Chemical Technology, L.P. | Diesel fuel |
US5425790A (en) * | 1992-12-23 | 1995-06-20 | Arco Chemical Technology, L.P. | Diesel fuel |
US5308365A (en) * | 1993-08-31 | 1994-05-03 | Arco Chemical Technology, L.P. | Diesel fuel |
US5520710A (en) * | 1993-09-29 | 1996-05-28 | George A. Olah | Cleaner burning and cetane enhancing diesel fuel supplements |
WO1995025153A1 (en) * | 1994-03-16 | 1995-09-21 | Olah George A | Cleaner burning and cetane enhancing diesel fuel supplements |
US6235068B1 (en) * | 1998-01-10 | 2001-05-22 | The Lubrizol Corporation | Fuel composition |
EP1178101A2 (de) * | 2000-08-04 | 2002-02-06 | Yoshiro Hamada | Umweltfreundlicher Brennstoff |
EP1178101A3 (de) * | 2000-08-04 | 2003-05-28 | Yoshiro Hamada | Umweltfreundlicher Brennstoff |
Also Published As
Publication number | Publication date |
---|---|
GB1266756A (de) | 1972-03-15 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: CITGO PETROLEUM CORPORATION, A CORP OF DE Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:CITIES SERVICE COMPANY;REEL/FRAME:004225/0709 Effective date: 19830830 |
|
AS | Assignment |
Owner name: CITIES SERVICE COMPANY A CORP. OF DE. Free format text: MERGER;ASSIGNOR:CITIES SERVICE OIL COMPANY;REEL/FRAME:004561/0817 Effective date: 19781220 |