EP0874039B1 - Diesel fuel compositions - Google Patents

Diesel fuel compositions Download PDF

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Publication number
EP0874039B1
EP0874039B1 EP98303110A EP98303110A EP0874039B1 EP 0874039 B1 EP0874039 B1 EP 0874039B1 EP 98303110 A EP98303110 A EP 98303110A EP 98303110 A EP98303110 A EP 98303110A EP 0874039 B1 EP0874039 B1 EP 0874039B1
Authority
EP
European Patent Office
Prior art keywords
acid
carbon atoms
composition
hydrocarbyl
diesel fuel
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.)
Revoked
Application number
EP98303110A
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German (de)
English (en)
French (fr)
Other versions
EP0874039A1 (en
Inventor
William J. Dimitrakis
Shigeru Sugimoto
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lubrizol Corp
Original Assignee
Lubrizol Corp
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Publication date
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Application filed by Lubrizol Corp filed Critical Lubrizol Corp
Publication of EP0874039A1 publication Critical patent/EP0874039A1/en
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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
    • C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
    • 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
    • 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
    • C10L1/1881—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
    • 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
    • C10L1/1881—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
    • C10L1/1883—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom polycarboxylic acid
    • 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
    • C10L1/1888—Carboxylic acids; metal salts thereof tall oil
    • 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
    • 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
    • C10L1/192—Macromolecular compounds
    • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid

Definitions

  • This invention relates to diesel fuels and, more particularly, to diesel fuels containing carboxylic acid mixtures.
  • Low sulfur diesel fuel defined as having up to 0.05% by weight sulfur content, has been required by law in the U.S. for on-highway use since October 1993 and in Europe since October 1996. Other nations in the Americas and Asia have timetables in place to follow suit.
  • the driving force to low sulfur diesel fuel is the desire to minimize harmful emissions from diesel vehicles.
  • Diesel fuel sulfur level is reduced by hydrotreatment of various distillate streams at the refinery. Hydrotreatment not only removes sulfur, but also removes other polar compounds and polycyclic aromatic compounds normally present in the diesel fuel. These compounds contribute to the natural lubricity of diesel fuel. When these compounds are removed during the hydrotreatment process, the final low sulfur diesel fuel tends to have poor natural lubricity.
  • Light duty diesel engines are usually fitted with rotary type fuel injection pumps. These pumps are lubricated only by the diesel fuel. Low sulfur fuels having poor natural lubricity have been shown to cause wear in these pumps leading to troublesome operation and premature pump failure. The use of lubricity additives in low sulfur diesel fuels has been shown to reduce or prevent pump wear.
  • Certain types of lubricity additives used in low sulfur diesel fuel have been found to contribute to fuel filter blockage and to pump plunger sticking. Lubricity additives having poor compatibility with engine oil have been shown to cause these problems. Compatibility is defined as the tendency for the diesel fuel containing the lubricity additive to form fuel insoluble deposits, gels, or heavy sticky residues when in contact with engine oil. These deposits, gels or residues have been shown to cause fuel filter blockage and injection pump sticking.
  • PCT International Publication No. WO 94/17160 discloses a fuel oil composition comprising a major proportion of a liquid hydrocarbon middle distillate fuel oil having a sulphur concentration of 0.2% by weight or less, and a minor proportion of an additive comprising an ester of a carboxylic acid and an alcohol wherein the acid has from 2 to 50 carbon atoms and the alcohol has one or more carbon atoms.
  • EP-A-0 488 747 describes alternative fuels for use in diesel powered vehicles, particularly fuels based on the use of short chain alcohols as a replacement for a hydrocarbon based diesel fuel.
  • the document describes a fuel additive essentially containing (a) an alkylene oxide condensate or the reaction product thereof and an alcohol, together with one or more of (b) a monocarboxylic fatty acid, (c) the reaction product of a hydrocarbyl substituted amine and formaldehyde, (d) a hydrocarbyl amine or the reaction product thereof with an alkylene oxide, or (e) a hydrocarbyl substituted dicarboxylic acid.
  • the hydrocarbyl substituted dicarboxylic acid may be as described in US-A-4 234 435 .
  • WO-A-96 23855 describes low sulfur diesel fuel oils and an additive composition comprising (a) an ashless dispersant comprising an acylated nitrogen compound, and (b) a carboxylic acid or an ester of the carboxylic acid and an alcohol wherein the acid has from 2 to 50 carbon atoms and the alcohol has one or more carbon atoms.
  • the additive is stated to improve the lubricity of the fuel oils and exhibit improved solubility in the fuel oil.
  • This invention relates to a diesel fuel composition, comprising a major amount of a diesel fuel having a 90% point distillation temperature in the range of 300°C to 390°C, and a minor amount of a combination of:
  • hydrocarbyl and “hydrocarbon based” denote a group having a carbon atom directly attached to the remainder of the molecule and having a hydrocarbon or predominantly hydrocarbon character within the context of this invention.
  • hydrocarbon based denote a group having a carbon atom directly attached to the remainder of the molecule and having a hydrocarbon or predominantly hydrocarbon character within the context of this invention.
  • groups include the following:
  • lower as used herein in conjunction with terms such as hydrocarbyl, alkyl, alkenyl, and the like, is intended to describe such groups which contain a total of up to 7 carbon atoms.
  • oil-soluble refers to a material that is soluble in mineral oil to the extent of at least about one gram per liter at 25°C.
  • the acid producing compounds of both components (A) and (B) are independently the anhydrides or partial esters (or partial acids) of such acids.
  • the partial esters are typically half ester and half acid.
  • a partial ester of a substituted succinic acid can be represented by the formula wherein: R is a hydrocarbyl group; and R' is a hydrocarbyl group, typically a lower alkyl group.
  • the first carboxylic acids and acid producing compounds (A) include oil soluble hydrocarbyl substituted mono- and polycarboxylic acids wherein the hydrocarbyl substituent has up to about 24 carbon atoms per molecule, and in one embodiment about 8 to about 24 carbon atoms, and in one embodiment about 8 to about 22 carbon atoms per molecule, and in one embodiment about 10 to about 18 carbon atoms.
  • These include fatty acids of up to about 24 carbon atoms, and especially fatty acids having about 10 to about 18 carbon atoms.
  • saturated and unsaturated fatty acids such as palmitic acid, lauric acid, stearic acid, oleic acid, myristic acid, linoleic acid, linolenic acid, decenoic acid, octadecenoic acid, octadecadienoic acid, 2-ethylhexanoic acid, isooctanoic acid, isodecanoic acid, neodecanoic acid, tall oil acid, and the like.
  • (A) is cis-9-octadecenoic acid, 9,12-octadecadienoic acid or a mixture thereof.
  • the acid producing compounds that are useful include the corresponding anhydrides.
  • the first carboxylic acid is a polycarboxylic acid, partial esters of such polycarboxylic acids can be used.
  • the first carboxylic acids and acid producing compounds (A) include hydrocarbyl substituted succinic acids and anhydrides. These can be represented by the formulae: wherein in each of Formulae (A-I), R is a hydrocarbyl group of about 8 to about 24 carbon atoms, and in one embodiment about 8 to about 20 carbon atoms, and in one embodiment about 10 to bout 18 carbon atoms. These include tetrapropenyl-substituted succinic acid and anhydride.
  • R is a hydrocarbyl group of about 8 to about 24 carbon atoms, and in one embodiment about 8 to about 20 carbon atoms, and in one embodiment about 10 to bout 18 carbon atoms.
  • Partial esters of the succinic acids or anhydrides represented by Formulae (A-l) can be prepared simply by the reaction of the acid or anhydride with an alcohol or phenolic compound. Particularly useful are the lower alkyl and alkenyl alcohols such as methanol, ethanol, allyl alcohol, propanol, cyclohexanol, etc. Esterification reactions are usually promoted by the use of alkaline catalysts such as sodium hydroxide or alkoxide, or an acidic catalyst such as sulfuric acid or toluene sulfonic acid.
  • alkaline catalysts such as sodium hydroxide or alkoxide
  • an acidic catalyst such as sulfuric acid or toluene sulfonic acid.
  • the second hydrocarbyl-substituted carboxylic acids and acid producing compounds (B) are described, for example, in the following U.S. patents: 3,219,666 ; 3,254,025 ; 3,271,310 ; 3,272,743 ; 3,272,746 ; 3,278,550 ; 3,288,714 ; 3,307,928 ; 3,346,354 ; 3,373,111 ; 3,374,174 ; 3,381,022 ; and 3,394,179 .
  • the second hydrocarbyl-substituted carboxylic acids (B) of formulae (A-1) are substituted carboxylic acids made by reacting one or more alpha-beta olefinically unsaturated carboxylic acid reagents containing on average from two to about 20 carbon atoms, exclusive of the carboxyl-based groups, with one or more olefin polymers or chlorinated analogs thereof.
  • Exemplary polybasic acids include maleic acid, fumaric acid, mesaconic acid, itaconic acid and citraconic acid.
  • the alpha-beta olefinically unsaturated carboxylic reagents can also be anhydrides or partial esters of the foregoing acids.
  • a useful alpha-beta olefinically unsaturated carboxylic acid reagent is maleic anhydride.
  • Methods of preparing the partial esters are well known to those of ordinary skill in the art and they can be satisfactorily described by noting the reactants used to produce them.
  • partial esters for use in the present invention can be made by esterifying monohydric or polyhydric alcohols or epoxides with any of the polycarboxylic acids or acid reagents referred to above.
  • the hydrocarbyl substituents of the second carboxylic acids (B) may be derived from olefin polymers or chlorinated analogs thereof. These substituents can be straight chained or branched chained. They typically have an average of at least about 30 carbon atoms per molecule, and in one embodiment an average of at least about 40 carbon atoms, and in one embodiment an average of at least about 50 carbon atoms. In one embodiment, these substituents have an average of from about 30 to about 500 carbon atoms per molecule, and in one embodiment about 40 to about 500 carbon atoms, and in one embodiment about 50 to about 500 carbon atoms.
  • the hydrocarbyl substituents may also include aromatic groups (especially phenyl groups and lower alkyl and/or lower alkoxy-substituted phenyl groups such as para(tertiarybutyl)-phenyl groups) and alicyclic groups such as would be obtained from polymerizable cyclic olefins or alicyclic-substituted polymerizable cyclic olefins, the hydrocarbyl-based substituents are usually free from such groups.
  • olefin polymers derived from such interpolymers of both 1,3-dienes and styrenes such as butadiene-1,3 and styrene or para-(tertiary butyl) styrene are exceptions to this general rule.
  • the olefin polymers are homo- or interpolymers of terminal hydrocarbyl olefins of about 2 to about 30 carbon atoms, and in one embodiment about 2 to about 16 carbon atoms.
  • a more typical class of olefin polymers is selected from that group consisting of homo- and interpolymers of terminal olefins of 2 to about 6 carbon atoms, and in one embodiment 2 to about 4 carbon atoms.
  • terminal and medial olefin monomers which can be used to prepare the olefin polymers from which the hydrocarbyl-based substituents are derived include ethylene, propylene, butene-1, butene-2, isobutene, pentene-1, hexene-1, heptene-1, octene-1, nonene-1, decene-1, pentene-2, propylene tetramer, diisobutylene, isobutylene trimer, butadiene-1,2, butadiene-1,3, pentadiene-1,2, pentadiene-1,3, isoprene, hexadiene-1,5, 2-chlorobutadiene-1,3, 2-methylheptene-1, 3-cyclohexylbutene-1, 3,3-dimethylpentene-1, styrenedivinylbenzene, vinyl-acetate allyl alcohol, 1-methylvinylacetate, acrylonitrile
  • the olefin polymers are polyisobutylenes such as those obtained by polymerization of a C 4 refinery stream having a butene content of about 35 to about 75% by weight and an isobutene content of about 30 to about 60% by weight in the presence of a Lewis acid catalyst such as aluminum chloride or boron trifluoride.
  • a Lewis acid catalyst such as aluminum chloride or boron trifluoride.
  • the hydrocarbyl substituent in the carboxylic acid or acid producing compound (B) as used in the present invention is an alkyl or alkenyl group.
  • the carboxylic acid or acid producing compound (B) is a hydrocarbyl substituted succinic acid or anhydride wherein the hydrocarbyl substituent contains on average about 30 to about 500 carbon atoms, and in one embodiment about 40 to about 500 carbon atoms, and in one embodiment about 50 to about 500 carbon atoms.
  • the diesel fuel has a sulfur content of up to about 0.05% by weight
  • component (B) is at least one polyisobutylene substituted succinic acid, the polyisobutylene group of said succinic acid having an average of at least about 50 carbon atoms per molecule.
  • the weight ratio of component (A) to component (B) is generally in the range of about 1:99 to about 99:1, and in one embodiment about 30:70 to about 70:30.
  • the inventive combination of (A) and (B) is comprised of about 50% to about 99% by weight of (A) and about 50% to about 1 % by weight of (B).
  • the diesel fuels that are useful with this invention have a 90% point distillation temperature in the range of about 300°C to about 390°C.
  • the diesel fuel has a sulfur content of up to about 0.05% by weight as determined by the test method specified in ASTM D 2622-87 entitled "Standard Test Method for Sulfur in Petroleum Products by X-Ray Spectrometry".
  • the fuels have a 90% point distillation temperature in the range of about 330°C to about 350°C.
  • the viscosity for these fuels typically ranges from about 1.3 to about 24 centistokes at 40 °C.
  • These diesel fuels can be classified as any of Grade Nos. 1-D, 2-D or 4-D as specified in ASTM D 975 entitled "Standard Specification for Diesel Fuel Oils”.
  • These diesel fuels can contain alcohols and esters.
  • the inventive diesel fuel compositions contain an effective amount of the combination of components (A) and (B) to improve the lubricity of such diesel fuels and, in one embodiment to improve the compatibility of such diesel fuels with engine oils.
  • concentration of the combination of (A) and (B) in the inventive diesel fuels is generally in the range of about 10 to about 1000 parts of such combination per million parts of diesel fuel, and in one embodiment about 10 to about 300 parts of such combination per million parts of diesel fuel.
  • inventive diesel fuel compositions can contain, in addition to the above-indicated carboxylic acids, other additives which are well known to those of skill in the art. These include dispersants, antioxidants, dyes, cetane improvers, rust inhibitors trialkylamines, bacteriostatic agents, gum inhibitors, metal deactivators, demulsifiers, upper cylinder lubricants and anti-icing agents.
  • Components (A) and (B) can be added directly to the fuel, or they can be diluted with a substantially inert, normally liquid organic diluent such as naphtha, benzene, toluene, xylene or a normally liquid fuel, to form an additive concentrate.
  • a substantially inert, normally liquid organic diluent such as naphtha, benzene, toluene, xylene or a normally liquid fuel
  • These concentrates generally contain from about 1 % to about 90% by weight of the combination of components (A) and (B).
  • These concentrates may also contain one or more other conventional additives known in the art or described hereinabove.
  • Ball on Cylinder Lubricity Evaluator (BOCLE) Test This test measures the adhesive wear aspects (scuffing) of the boundary lubrication properties of diesel fuels on rubbing surfaces. The test is performed using a nonrotating steel ball that is held in a vertically mounted chuck in loaded contact of 7,000 grams with a steel ring rotating axially at 300 rpm. The ring is partially immersed in a sample of the test fluid held at 25°C and in an atmosphere of 50% relative humidity. The mean wear scar diameter on the steel ball after 2 minutes running is used to assess the resistance of the fluid to adhesive wear or its lubricity. The fuel used in each test is kerosene. The results are as follows:
  • Sample 1 2 3 Acid A-1, ppm 0 100 100 Acid B-1, ppm 0 5 0 Mean wear scar diameter, mm 0.61 0.41 0.61
  • Sample 1 2 3 Acid A-1, ppm 0 60 60 Acid B-1, ppm 0 4 0 Mean wear scar diameter, mm 0.63 0.53 0.57
  • HFRR High Frequency Reciprocating Rig
  • Lubricity Improver Compatibility Test This test is performed using the following procedure: (1) A mixture of 50 grams of the combination of Acid A-1 and Acid B-1 (Sample 1) or 50 grams of Acid A-1 (Sample 2), 49 grams of diesel engine oil, and 1 gram of water is prepared. (2) The mixture from step (1) is stored for 7 days at 80°C. (3) The mixture from step (2) is centrifuged for 1 hour at 2000 rpm. (4) The sediment formed during step (3) is collected and dissolved in 100 ml of low sulfur diesel fuel.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Liquid Carbonaceous Fuels (AREA)
EP98303110A 1997-04-23 1998-04-22 Diesel fuel compositions Revoked EP0874039B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US84217097A 1997-04-23 1997-04-23
US842170 1997-04-23

Publications (2)

Publication Number Publication Date
EP0874039A1 EP0874039A1 (en) 1998-10-28
EP0874039B1 true EP0874039B1 (en) 2008-01-02

Family

ID=25286694

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98303110A Revoked EP0874039B1 (en) 1997-04-23 1998-04-22 Diesel fuel compositions

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Country Link
EP (1) EP0874039B1 (ja)
JP (1) JP4620814B2 (ja)
DE (1) DE69838925T2 (ja)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6051039A (en) * 1998-09-14 2000-04-18 The Lubrizol Corporation Diesel fuel compositions
GB2354254A (en) * 1999-09-20 2001-03-21 Exxon Research Engineering Co Fuel composition with improved lubricity performance
GB2357296A (en) * 1999-12-16 2001-06-20 Exxon Research Engineering Co Low sulphur fuel composition with enhanced lubricity
GB0217056D0 (en) * 2002-07-23 2002-08-28 Ass Octel Use
ES2257220A1 (es) * 2003-07-23 2006-07-16 The Associated Octel Company Limited Composicion.
CN105542884B (zh) 2010-05-18 2018-01-23 路博润公司 提供去污力的方法和组合物
SG10201810691XA (en) * 2014-05-30 2018-12-28 Lubrizol Corp Concentrated multi-functional fuel additive packages
US9873848B2 (en) 2015-12-04 2018-01-23 Afton Chemical Corporation Fuel additives for treating internal deposits of fuel injectors

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Publication number Priority date Publication date Assignee Title
FR1405551A (fr) * 1963-07-16 1965-07-09 Exxon Research Engineering Co Additifs anti-usure destinés à améliorer l'onctuosité d'hydrocarbures liquides
US4032303A (en) * 1975-10-01 1977-06-28 The Lubrizol Corporation Fuel compositions containing esters and ester-type dispersants
CA1085154A (en) * 1976-02-12 1980-09-09 Bruce H. Garth Corrosion inhibitor compositions
DE69004692T2 (de) * 1990-09-20 1994-03-10 Ethyl Petroleum Additives Ltd Kohlenwasserstoffzusammensetzungen und Zusätze dafür.
US5197997A (en) * 1990-11-29 1993-03-30 The Lubrizol Corporation Composition for use in diesel powered vehicles
GB9301119D0 (en) * 1993-01-21 1993-03-10 Exxon Chemical Patents Inc Fuel composition
GB2285057B (en) * 1993-12-23 1997-12-10 Ethyl Petroleum Additives Ltd Evaporative burner fuels and additives therefor
EP0743974B1 (en) * 1994-12-13 2000-08-16 Infineum USA L.P. FUEL OIL COMPOSITIONS comprising petroleum based fuel oils, ethylene-unsaturated ester copolymers and esters of polyhydric alcohols with carboxylic acids
GB9502041D0 (en) * 1995-02-02 1995-03-22 Exxon Chemical Patents Inc Additives and fuel oil compositions
JP3829948B2 (ja) * 1995-03-24 2006-10-04 出光興産株式会社 ディーゼル軽油組成物
JP3379866B2 (ja) * 1995-04-24 2003-02-24 花王株式会社 軽油添加剤および軽油組成物

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Publication number Publication date
JP4620814B2 (ja) 2011-01-26
DE69838925D1 (de) 2008-02-14
EP0874039A1 (en) 1998-10-28
DE69838925T2 (de) 2008-12-11
JPH10330769A (ja) 1998-12-15

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