WO1998011177A1 - Additif pour combustibles a base d'ester de polyalcool - Google Patents

Additif pour combustibles a base d'ester de polyalcool Download PDF

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Publication number
WO1998011177A1
WO1998011177A1 PCT/US1997/016329 US9716329W WO9811177A1 WO 1998011177 A1 WO1998011177 A1 WO 1998011177A1 US 9716329 W US9716329 W US 9716329W WO 9811177 A1 WO9811177 A1 WO 9811177A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
fuel composition
branched
ester
composition according
Prior art date
Application number
PCT/US1997/016329
Other languages
English (en)
Inventor
Elisavet P. Vrahopoulou
John E. Johnston
Richard H. Schlosberg
Simon R. Kelemen
Michael Siskin
Original Assignee
Exxon Research And Engineering Company
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Exxon Research And Engineering Company filed Critical Exxon Research And Engineering Company
Priority to AU44166/97A priority Critical patent/AU734585B2/en
Priority to JP10513954A priority patent/JP2001501231A/ja
Priority to CA002264707A priority patent/CA2264707A1/fr
Priority to EP97942478A priority patent/EP0948586A4/fr
Priority to BR9711783A priority patent/BR9711783A/pt
Publication of WO1998011177A1 publication Critical patent/WO1998011177A1/fr

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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
    • 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
    • C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols
    • 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
    • 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

Definitions

  • the present invention relates generally to a polyol ester additive for fuels applications and more particularly to a fuels additive comprising a partially esterified polyol ester which exhibits reduced engine deposits including reduced intake valve deposits (“IVD”) and combustion chamber deposits (“CCD”) and improves the wear and frictional performance of the materials it contacts including the crankcase oil.
  • the polyol ester fuels additives of this invention have unconverted hydroxyl groups from the reaction product of a polyol with a branched acid, linear saturated acid or mixtures thereof.
  • Esters have generally excellent thermal and oxidative stability characteristics, and have been widely used in synthetic or partially synthetic crankcase lubricants. The art has recently recognized the potential role esters may serve as fuel additives. For example U.S. 5,427,591 discloses the use of certain hydroxylaromatic esters as fuels additives to reduce engine deposits. U.S. 5,21 1,721 discloses the use of polyalkylene esters as fuels additives to control engine deposits and improve fuel hazing. U.S.
  • 5,089,028 teaches the use of a combination of a polyalkenyl succinimide, an olefinic hydrocarbon polymer, an ester and a polyether to provide engine intake valve, port fuel injector, and carburetor detergency as well as corrosion inhibitors.
  • 4,920,691 teaches a combination of a low molecular weight straight chain carboxylic acid ester, i.e., molecular weight less than 200, and a high molecular weight straight chain carboxylic acid ester, i.e., molecular weight ranging from 300 to 1000 to achieve both detergency benefits and cylinder wall lubrication.
  • a low molecular weight straight chain carboxylic acid ester i.e., molecular weight less than 200
  • a high molecular weight straight chain carboxylic acid ester i.e., molecular weight ranging from 300 to 1000 to achieve both detergency benefits and cylinder wall lubrication.
  • the amount of detergent additives needs be minimized because of the deleterious effects of the by-products such additives have on crankcase lubricants; see, for example, U.S. 5,044,478. Small amounts of the by-product of these additives, upon breakdown in the combustion chamber, wind up in the crankcase lubricant and contribute
  • the present inventors have developed a unique fuels additive which employs a polyol ester synthesized from a polyol and branched acid, saturated linear acid, or mixtures thereof, in such a manner that the resulting ester has unconverted hydroxyl groups.
  • the resultant fuel composition displays enhanced control of intake valve deposits ("IVD”), combustion chamber deposits (“CCD”), and reduced wear and friction in both the fuel line, combustion chamber and piston/cylinder assembly.
  • IVD intake valve deposits
  • CCD combustion chamber deposits
  • Improved IVD and CCD are achieved without the crankcase lubricant deficits normally associated with detergent additives.
  • the fuel additive of this invention which may survive the combustion chamber, improves the wear and friction performance of the crankcase oil.
  • the ester comprises the reaction product of an alcohol having the general formula R(OH) n where R is an aliphatic group, cyclo-aliphatic group, or a combination thereof having from about 2 to 20 carbon atoms and n is at least two where the said aliphatic group is branched or linear.
  • the ester is characterized as having a hydroxyl number ranging from greater than about 5 to about 180.
  • the fuels referred to in this invention generally comprise distillate fuels, and typically comprise a major amount of gasoline.
  • the ester additive comprises a minor amount of the fuel, ranging from about 10 to about 10,000 wppm.
  • Figure 1 exhibits friction coefficients under varying load, speed and temperature conditions.
  • Figure 2 exhibits wear rate data under varying load, speed and temperature conditions.
  • the fuel composition of the present invention employs a polyol ester which comprises a compound represented by the general formula R(OOCR') n and at least one of the following compounds:
  • n is an integer having a value of at least 2
  • R is an aliphatic group, cycloaliphatic group, or combinations thereof containing from about 2 to about 20 or more carbon atoms where the said alphatic group is branched or linear
  • R' is a branched or linear hydrocarbyl group having a carbon number in the range between about C2 to C20
  • (i) is an integer having a value in the range of 0 to n.
  • the polyol ester composition may also include excess R(OH) n .
  • the ester is preferably formed by reacting a polyhydroxyl compound (i.e., polyol) with at least one branched, saturated linear acid or mixtures thereof.
  • a polyhydroxyl compound i.e., polyol
  • the composition of the feed polyol and acid are adjusted so as to provide the desired composition of the product ester.
  • the esterification reaction is preferably conducted, with or without a catalyst, at a temperature in the range of about 140°C to about 250°C and a pressure ranging from about 30 mm Hg to 760 mm Hg for about 0.1 to 12 hours, preferably 1 to 8 hours.
  • the reactor apparatus may vacuum strip acid to provide the preferred final composition.
  • the product may then be treated in a contact process step by contacting it with a solid such as alumina, zeolite activated carbon, or clay, for example.
  • R is an aliphatic group, cycloaliphatic group or combinations thereof where the aliphatic group is branched or linear, and n is at least 2.
  • the hydrocarbyl group may contain from about 2 to about 20 or more carbon atoms and is preferably an alkyl group.
  • the hydroxyl groups may be separated by one or more carbon atoms.
  • the polyhydroxyl compounds generally may contain one or more oxyethylene groups and accordingly include compounds such as polyether polyols.
  • alcohols are particularly useful as polyols in the practice of the present invention: neopentyl glycol, 2,2-dimethanoI butane, trimethylol ethane, trimethylol butane, mono-pentaerythritol, technical grade pentaerythritol, di- pentaerythritol, tri-pentaerythritol, ethylene glycol, propylene glycol and poiyalkylene glycols (e.g., polyethylene glycols, polypropylene glycols, 1,4-butanediol, sorbitol and the like, 2-methylpropanediol, polybutylene glycols, etc., and blends thereof such as an oligomerized mixture of ethylene glycol and propylene glycol).
  • polyethylene glycols polypropylene glycols, 1,4-butanediol, sorbitol and the like, 2-methylpropanediol
  • the most preferred alcohols are technical grade (e.g., approximately 88% mono-, 10% di- and 1-2% tri- pentaerythritol) pentaerythritol, monopentaerythritol, di-pentaerythritol, neopentyl glycol and trimethylol propane.
  • the branched acid is preferably a mono-carboxylic acid which has a carbon number in the range between about C to C20 > ore preferably about C5 to C JQ wherein methyl or ethyl branches are preferred.
  • the mono-carboxylic acid is preferably at least one acid selected from the group consisting of: 2,2- dimethyl propionic acid (neopentanoic acid), neoheptanoic acid, neooctanoic acid, neononanoic acid, iso- hexanoic acid, neodecanoic acid, 2-ethyl hexanoic acid (2EH), 3,5,5-trimethyl hexanoic acid (TMH), isoheptanoic acid, isooctanoic acid, isononanoic acid and isodecanoic acid.
  • 2,2- dimethyl propionic acid neopentanoic acid
  • neoheptanoic acid ne
  • branched acid is 3,5,5-trimethyl hexanoic acid.
  • the term "neo" as used herein refers to a trialkyl acetic acid, i.e., an acid which is triply substituted at the alpha carbon with alkyl groups. These alkyl groups are equal to or greater than CH3 as shown in the general structure set forth herebelow:
  • the branched oxo acid is preferably a mono-carboxylic oxo acid which has a carbon number in the range between about C5 to Cio, preferably C 7 ' to Cio, wherein methyl branches are preferred.
  • the mono-carboxylic oxo acid is at least one acid selected from the group consisting of: isopentanoic acids, isohexanoic acids, isoheptanoic acids, isooctanoic acids, isononanoic acids, and isodecanoic acids.
  • One particularly preferred branched oxo acid is an isooctanoic acid known under the tradename Cekanoic ® 8 acid, commercially available from Exxon Chemical Company.
  • branched oxo acid is 3,5,5 trimethylhexanoic acid, a form of which is also commercially available from Exxon Chemical Company under the tradename Cekanoic ® 9 or Ck ® 9.
  • the term "iso" is meant to convey a multiple isomer product made by the oxo process. It is desirable to have a branched oxo acid comprising multiple isomers, preferably more than 3 isomers, most preferably more than 5 isomers.
  • Branched oxo acids may be produced in the so-called "oxo" process by hydroformylation of commercial C4-C 9 olefin fractions to a corresponding branched C 5 - C10 aldehyde-containing oxonation product.
  • oxo branched C 5 - C10 aldehyde-containing oxonation product.
  • the hydroformylation process is adjusted to maximize oxo aldehyde formation. This can be accomplished by controlling the temperature, pressure, catalyst concentration, and/or reaction time. Thereafter, the demetalled crude aldehyde product is distilled to removed oxo alcohols from the oxo aldehyde which is then oxidized according to the reaction below to produce the desired oxo acid:
  • R is a branched alkyl group.
  • oxo acids can be formed by reacting the demetalled crude aldehyde product with water in the presence of an acid-forming catalyst and in the absence of hydrogen, at a temperature in the range between about 93 to 205°C and a pressure of between about 0.1 to 6.99 Mpa, thereby converting the concentrated aldehyde-rich product to a crude acid product and separating the crude acid product into an acid-rich product and an acid-poor product.
  • the production of branched oxo acids from the cobalt catalyzed hydroformylation of an olefinic feedstream preferably comprises the following steps:
  • the olefinic feedstream is preferably any C 4 to C 9 olefin, more preferably a branched C 7 olefin. Moreover, the olefinic feedstream is preferably a branched olefin, although a linear olefin which is capable of producing all branched oxo acids are also contemplated herein.
  • the hydroformylation and subsequent reaction of the crude hydroformylation product with either (i) oxygen (e.g., air), or (ii) water in the presence of an acid-forming catalyst, is capable of producing branched Cs to Cio acids, more preferably branched Cg acid (i.e., Cekanoic ® 8 acid).
  • Each of the branched oxo C 5 to Cio acids formed by the conversion of branched oxo aldehydes typically comprises, for example, a mixture of branched oxo acid isomers, e.g., Cekanoic ® 8 acid comprises a mixture of 26 wt% 3,5-dimethyl hexanoic acid, 19 wt% 4,5-dimethyl hexanoic acid, 17 wt% 3,4-dimethyl hexanoic acid, 1 1 wt% 5-methyl heptanoic acid, 5 wt% 4-methyl heptanoic acid, and 22 wt% of mixed methyl heptanoic acids and dimethyl hexanoic acids.
  • Cekanoic ® 8 acid comprises a mixture of 26 wt% 3,5-dimethyl hexanoic acid, 19 wt% 4,5-dimethyl hexanoic acid, 17 wt% 3,4-dimethyl he
  • any type of catalyst known to one of ordinary skill in the art which is capable of converting oxo aldehydes to oxo acids is contemplated by the present invention.
  • Preferred acid-forming catalysts are disclosed in co-pending and commonly assigned U.S. Patent Application, Serial No. 08/269,420 (Vargas et al.), filed on June 30, 1994, and which is incorporated herein by reference. It is preferable if the acid- forming catalyst is a supported metallic or bimetallic catalyst.
  • One such catalyst is a bimetallic nickel-molybdenum catalyst supported on alumina or silica alumina which catalyst has a phosphorous content of about 0.1 wt% to 1.0 wt%, based on the total weight of the catalyst.
  • Another catalyst can be prepared by using phosphoric acid as the solvent for the molybdenum salts which are impregnated onto the alumina support.
  • Still other bimetallic, phosphorous-free Ni/Mo catalyst may be used to convert oxo aldehydes to oxo acids.
  • the preferred mono-and/or di-carboxylic linear acids are any linear saturated alkyl carboxylic acid having a carbon number in the range between about C2 to C20, preferably C2 to Cjo
  • linear saturated acids include acitic, propionic, n- pentanoic, n-heptanoic, n-octanoic, n-nonanoic, and n-decanoic acids.
  • the "high hydroxyl" ester employed in the present invention has from about 1% to about 35% unconverted hydroxyl groups, based upon the total amount of hydroxyl groups in the alcohol.
  • a common technique for characterizing the conversion of hydroxyl groups is hydroxyl number.
  • a standard method for measuring hydroxyl number is detailed by the American Oil Chemists Society as A.O.C.S., Cd 13-60.
  • the ester of the present invention is characterized as having hydroxyl numbers ranging for about greater than 5 to about 180.
  • the term "high hydroxyl,” as used herein, refers to partially esterified esters characterized as having a hydroxyl number greater than about 5.
  • the high hydroxyl ester product of this invention can be used as a fuels additive by itself or in conjunction with other fuels additives such as detergents or dispersants, anti-oxidants, corrosion inhibitors, pourpoint depressants, color stabilizers, carrier fluids, solvents, and the like.
  • fuels additives such as detergents or dispersants, anti-oxidants, corrosion inhibitors, pourpoint depressants, color stabilizers, carrier fluids, solvents, and the like.
  • the foregoing additives may provide a multiplicity of effects and are included herein to illustrate that the high hydroxyl ester of the present invention may be complimented by such additives. This approach is well known in the relevant art.
  • the high hydroxyl ester is suitable as an additive or admixture to a wide variety of motor fuels generally identified as hydrocarbons which boil in the gasoline boiling range of 80°-450°F. This includes straight or branched chain paraffins, cyclo- paraffins, olefins, oxygenates (including MTBE, ETBE, TAME and the like), aromatic hydrocarbons, alcohols (including methanol and ethanol), or mixtures thereof.
  • the present invention is preferably suitable as a gasoline additive wherein gasoline is referred to in a general sense as comprising a mixture of liquid hydrocarbons or hydrocarbon oxygenates having an initial boiling point in the range from about 70 to 135°F and a final boiling point in the range from about 250 to 450°F as determined by the ASTM D86 distillation method.
  • a polyol ester illustrative of the present invention was prepared in the following manner:
  • Cekanoic ® 8 acid (4 moles, 576 g) and glycerol (2 moles, 184 g) were charged to an esterifi cation reactor under a slight positive nitrogen flow. The mixture was heated for about three hours to a maximum temperature of 220°C during which time about 69cc of H 2 O were collected in a Dean-Stark Trap. At this time a vacuum was applied to strip any residual Cekanoic ® 8 acid. After about two hours of stripping, the reaction mixture was cooled and a sample was taken and analyzed by gas chromatography. This analysis indicated the absence of glycerol and of Cekanoic ® 8 acid. A total of 525 g of product were obtained. The sample exhibited a hydroxyl number of 79.
  • One of the important aspects of this invention is its reduction of IVD and CCD in internal combustion engines.
  • Two types of bench tests as well as testing in internal combustion engines were utilized to determine and compare intake valve deposits and combustion chamber deposits.
  • the STRIDE (Surrogate Test Related to Intake Deposits in Engines) and the TORID test are both bench tests which emulate the effects of fuels composition on intake valve deposits and combustion chamber deposits, respectively.
  • the STRIDE test is described in detail in U.S. patent 5,492,005.
  • the TORID test was developed by Exxon Research and Engineering Company and is used to emulate the effects of fuel additives on combustion chamber deposits.
  • the TORID test differs from the STRIDE test inasmuch as the sample, which is controllably heated as in the STRIDE testing, is also subjected to a controlled flash flame to simulate combustion chamber conditions.
  • the results of the STRIDE tests may be used to predict the effect of fuel additives on intake valve deposits; the TORID tests may be used to predict the effect of fuel additives on combustion chamber deposits.
  • the sample fuel was delivered at a rate of 10 ml/hour to a 0.3 cm ⁇ stainless steel nub surface.
  • the surface temperature was cycled from about 150°C to about 300°C. Cycle time was approximately 8 minutes. Total time of tests was approximately four hours.
  • Hercolube F is a tradename of Hercules Inc.; this commercially available ester additive has a hydroxyl number of ⁇ 5.
  • Priolube 3970 is a trade name of Unichema; this commercially available ester additive has a hydroxyl number of ⁇ 5.
  • Parabar 9440 is a trade name of a mixture of glycerol oleatcs commercially available from Exxon Chemical Company; it has a hydroxyl number of 223.
  • Table 1 Certain specified compounds identified in Table 1 were added to gasoline (base fuel) and subjected to actual internal combustion engine testing.
  • Tables 2 and 3 show engine test results for IVD and CCD relative to the base fuel. These data evidence a reduction of IVD and CCD in the percentages shown relative to the base fuel.
  • Another feature of the present invention is improved wear and friction performance, both in the fuel delivery system (such as fuel pump and fuel injection system) and within the combustion chamber and piston/cylinder assembly by surficial coating of the operating surfaces.
  • Yet another aspect of the present invention is that the high hydroxyl ester additive does not deteriorate the crankcase lubricant when amounts of the fuel additive reach the engine's crankcase lubricant.
  • the high hydroxyl ester of the present invention is understood to survive the combustion chamber conditions and, upon passing into the crankcase improves the wear and frictional performance of the crankcase oil.
  • the Falex Block-on-Ring tribometer was also equipped with a proprietary eddy current sensor to measure the wear rate of the block during the test.
  • Figure 2 exhibits wear rates of the "used" engine oils and shows improved performance in the case of the oil from the engine run with the fuel containing the high hydroxyl ester.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Combustion & Propulsion (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)

Abstract

Cet additif pour combustible à base d'ester de polyalcool permet de réduire les dépôts se formant sur les soupapes d'admission ainsi que dans la chambre d'explosion. Cet ester, qui comporte entre environ 1 et environ 35 % de groupes hydroxyles non convertis, se caractérise par le fait que son nombre hydroxyle est compris entre environ 5 et environ 180.
PCT/US1997/016329 1996-09-13 1997-09-11 Additif pour combustibles a base d'ester de polyalcool WO1998011177A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
AU44166/97A AU734585B2 (en) 1996-09-13 1997-09-11 Polyol ester fuels additive
JP10513954A JP2001501231A (ja) 1996-09-13 1997-09-11 ポリオールエステル燃料添加剤
CA002264707A CA2264707A1 (fr) 1996-09-13 1997-09-11 Additif pour combustibles a base d'ester de polyalcool
EP97942478A EP0948586A4 (fr) 1996-09-13 1997-09-11 Additif pour combustibles a base d'ester de polyalcool
BR9711783A BR9711783A (pt) 1996-09-13 1997-09-11 Composi-Æo de combust¡vel para uso em motores de combustÆo interna

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US71299196A 1996-09-13 1996-09-13
US08/712,991 1996-09-13

Publications (1)

Publication Number Publication Date
WO1998011177A1 true WO1998011177A1 (fr) 1998-03-19

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PCT/US1997/016329 WO1998011177A1 (fr) 1996-09-13 1997-09-11 Additif pour combustibles a base d'ester de polyalcool

Country Status (7)

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EP (1) EP0948586A4 (fr)
JP (1) JP2001501231A (fr)
CN (1) CN1230210A (fr)
AU (1) AU734585B2 (fr)
BR (1) BR9711783A (fr)
CA (1) CA2264707A1 (fr)
WO (1) WO1998011177A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL1036154C (en) * 2008-11-05 2010-05-06 Criss Cross Technology B V A motor fuel additive with enhanced properties, and processes for the production thereof.
WO2012163935A2 (fr) 2011-05-30 2012-12-06 Shell Internationale Research Maatschappij B.V. Compositions de carburants liquides

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6125246B2 (ja) * 2013-01-30 2017-05-10 日野自動車株式会社 燃料デポジット単体試験装置
CN106318484A (zh) * 2016-10-10 2017-01-11 熊炳辉 一种用地沟油生产的环保清洁生物汽油及其制备方法
CN109810736A (zh) * 2019-02-25 2019-05-28 山东大学 一类化合物作为汽油润滑剂在汽油上的应用
FR3103815B1 (fr) * 2019-11-29 2021-12-17 Total Marketing Services Utilisation de diols comme additifs de détergence

Citations (1)

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Publication number Priority date Publication date Assignee Title
US4617026A (en) * 1983-03-28 1986-10-14 Exxon Research And Engineering Company Method for improving the fuel economy of an internal combustion engine using fuel having hydroxyl-containing ester additive

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Publication number Priority date Publication date Assignee Title
US2868629A (en) * 1956-11-13 1959-01-13 Pure Oil Co Motor fuel
US3377149A (en) * 1959-02-04 1968-04-09 Texaco Inc Motor fuel containing an octane appreciator
US3672854A (en) * 1969-12-03 1972-06-27 Universal Oil Prod Co Middle distillate

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4617026A (en) * 1983-03-28 1986-10-14 Exxon Research And Engineering Company Method for improving the fuel economy of an internal combustion engine using fuel having hydroxyl-containing ester additive

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP0948586A4 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL1036154C (en) * 2008-11-05 2010-05-06 Criss Cross Technology B V A motor fuel additive with enhanced properties, and processes for the production thereof.
WO2010053354A2 (fr) * 2008-11-05 2010-05-14 Criss Cross Technology Bv Additif de carburant moteur ayant des propriétés améliorées et procédés de fabrication de cet additif
WO2010053354A3 (fr) * 2008-11-05 2010-11-04 Criss Cross Technology Bv Additif de carburant moteur ayant des propriétés améliorées et procédés de fabrication de cet additif
WO2012163935A2 (fr) 2011-05-30 2012-12-06 Shell Internationale Research Maatschappij B.V. Compositions de carburants liquides

Also Published As

Publication number Publication date
CA2264707A1 (fr) 1998-03-19
JP2001501231A (ja) 2001-01-30
EP0948586A4 (fr) 2000-02-23
EP0948586A1 (fr) 1999-10-13
AU4416697A (en) 1998-04-02
BR9711783A (pt) 1999-08-24
AU734585B2 (en) 2001-06-14
CN1230210A (zh) 1999-09-29

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