EP1252267A1 - Gasoline composition - Google Patents

Gasoline composition

Info

Publication number
EP1252267A1
EP1252267A1 EP01942375A EP01942375A EP1252267A1 EP 1252267 A1 EP1252267 A1 EP 1252267A1 EP 01942375 A EP01942375 A EP 01942375A EP 01942375 A EP01942375 A EP 01942375A EP 1252267 A1 EP1252267 A1 EP 1252267A1
Authority
EP
European Patent Office
Prior art keywords
composition according
friction reducing
reducing additive
gasoline
fatty acid
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.)
Granted
Application number
EP01942375A
Other languages
German (de)
French (fr)
Other versions
EP1252267B1 (en
Inventor
Robert Howie Barbour
Gideon Freeman
Alan Mark Schilowitz
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.)
ExxonMobil Technology and Engineering Co
Original Assignee
ExxonMobil Research and Engineering Co
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 ExxonMobil Research and Engineering Co filed Critical ExxonMobil Research and Engineering Co
Publication of EP1252267A1 publication Critical patent/EP1252267A1/en
Application granted granted Critical
Publication of EP1252267B1 publication Critical patent/EP1252267B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L10/00Use of additives to fuels or fires for particular purposes
    • C10L10/08Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/188Carboxylic acids; metal salts thereof
    • C10L1/1881Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/188Carboxylic acids; metal salts thereof
    • C10L1/1881Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
    • C10L1/1883Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom polycarboxylic acid
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/188Carboxylic acids; metal salts thereof
    • C10L1/1888Carboxylic acids; metal salts thereof tall oil
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/19Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/222Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/2222(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/222Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224Amides; Imides carboxylic acid amides, imides

Definitions

  • This invention relates to low sulphur gasoline compositions which have improved response to friction reducing additives.
  • Fuels such as gasolines and diesels are used rather widely in automotive transport and for providing power for heavy duty equipment, especially diesels due to their high fuel economy.
  • one of the problems when such fuels are burned in internal combustion engines is their low lubricity. This reduction in lubricity arises because as the sulphur content in the fuel is reduced eg by hydrodesulphurisation, this process also incidentally removes the lubricity providing polar or friction reducing molecules such as eg the nitrogenous compounds present in such fuels.
  • SAE Paper No. 962010 by Wei Dan Ping et al entitled “Comparison of the Lubricity of Gasoline and Diesel Fuels” (1996) describes the effects of various additives on such fuels including low sulphur fuels.
  • EP-A-0860494, EP-A-0739970 and EP-A-0635558 relate to low sulphur diesel, gas oils and gas oils (diesel fuels) respectively containing esters derived by transesterification of vegetable oils, glycerol/fatty acid esters and lower alkyl esters of a mixture of saturated and unsaturated fatty acids derived from oleaginous seeds respectively as a lubricity improving agent.
  • low sulphur gasolines especially gasolines having a sulphur content of ⁇ 30 ppm.
  • WO99/00467 describes a fuel composition of improved lubricity comprising a spark ignition fuel and an alkanolamide of a fatty acid or a modified fatty acid having a maximum sulphur content of 0.05% based on mass.
  • gasolines are mentioned and all of the examples relate to diesels, especially Swedish Class I low sulphur diesel fuel.
  • bromine number or UV absorbance of the fuels tested or claimed is also no reference to the bromine number or UV absorbance of the fuels tested or claimed. It has now been found that the efficacy of the friction reducing additives can be significantly improved by mixing the same with fuels of specific, predetermined characteristics.
  • the present invention is a composition
  • a low sulphur gasoline having a sulphur content of less than 30 ppm, a bromine number of less than about 10 and an ultraviolet absorbance at 319 nm below 0.15 and (ii) an effective amount of an ashless friction reducing additive which is a fatty acid having 10-30 carbon atoms or a derivative thereof.
  • the gasoline should have a bromine number (which is related to the amount of olefins in the fuel) below 10, suitably below 5 and preferably below 4.5. Furthermore, the gasoline should have a sulphur content below 30 ppm, suitably below 20 ppm and preferably below 10 ppm. Again the UV absorbance of the fuel at 319 nm should be below 0.1 , suitably below 0.07 and preferably below 0.05.
  • the ashless friction reducing additive in the composition is suitably a liquid at room temperature and pressure and is selected from C10-C30 fatty acids, preferably a C10-C24 fatty acid, or a derivative thereof and mixtures thereof.
  • Such ashless friction reducing additives are suitably derived from naturally occurring fats and oils and the preferred derivatives are suitably selected from the alkylamine salts, alkyl amides and alkyl esters of such acids and oligomers thereof.
  • An example of an alkyl amine carboxylate salt is n- butylamine oleate or a derivative thereof and an example of a naturally occurring fatty acid is a substance comprising a fatty acid, a tall oil fatty acid or derivatives thereof.
  • n-Butylamine oleate has the formula:
  • n-butylamine oleate is commercially sold as a friction modifier as RS124 by Bitrez Ltd.
  • the substance comprising fatty acids may be either 100% fatty acids, or substantially 100% fatty acids, or may be a mixture of fatty acids and/or tall oil acids or derivatives thereof. Such a mixture suitably contains at least 30% w/w, preferably at least 50% w/w of fatty acids.
  • An example of a suitable commercially available substance containing fatty acids is TOLAD® 9103 (ex Baker-Petrolite Ltd).
  • the friction reducing additive is used in an amount sufficient to provide effective lubricity to the composition.
  • the friction reducing additive is suitably used in an amount of less than 1000 mg per kilogram of base fuel in the composition, preferably from 1 to 500 mg and more preferably from about 5 to 100 mg per kg of base fuel in the composition.
  • the ashless friction reducing additive may be part of an additive concentrate comprising a number of additives.
  • the amount of the friction reducing additive is suitably from 0.2-25% w/w, preferably from 0.5-20% w/w and more preferably from 3 to 15% w/w.
  • the treat level of the friction reducing additive in the gasoline is suitably from 4-200 ppm, preferably from 10-100 ppm and more preferably from 25-75 ppm.
  • ⁇ FC Mean FC (base fuel)- Mean FC (additised fuel)
  • % ⁇ FC [Mean FC (base fuel)- Mean FC (additised fuel)] x 100/ Mean FC (base fuel)

Landscapes

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

Abstract

This invention relates to a fuel composition comprising (i) a low sulphur fuel having a sulphur content of less than 30 ppm, a bromine number of less than 10 and an ultraviolet absorbance at 319 nm is below 0.15 and (ii) an effective amount of an ashless friction reducing additive which is a fatty acid having 10-30 carbon atoms or a derivative thereof. The fuel of the specified characteristics shown improved response to the friction reducing additive in respect of its lubricity performance.

Description

GASOLINE COMPOSITION
This invention relates to low sulphur gasoline compositions which have improved response to friction reducing additives.
Fuels such as gasolines and diesels are used rather widely in automotive transport and for providing power for heavy duty equipment, especially diesels due to their high fuel economy. However, one of the problems when such fuels are burned in internal combustion engines is their low lubricity. This reduction in lubricity arises because as the sulphur content in the fuel is reduced eg by hydrodesulphurisation, this process also incidentally removes the lubricity providing polar or friction reducing molecules such as eg the nitrogenous compounds present in such fuels. A prior published SAE Paper No. 962010 by Wei Dan Ping et al entitled "Comparison of the Lubricity of Gasoline and Diesel Fuels" (1996) describes the effects of various additives on such fuels including low sulphur fuels. Whilst efforts hitherto have been devoted to the addition of such friction reducing nitrogenous compounds into the fuels after hydrodesulphurisation to restore the lubricity of the fuel, little attention has been paid to the nature of the fuel itself in order to improve the efficiency of such fuels.
Prior published GB-A-2306246 and GB-A-2307247 relate to the use of carboxylic acid derivatives as an additive for improving the lubricity of low sulphur-content fuels which are primarily middle distillate fuels such as eg diesel, jet and biodiesel fuels. However, there is no mention of gasolines or fuels having a sulphur content of less than 30 ppm in these documents.
Similarly, EP-A-0860494, EP-A-0739970 and EP-A-0635558 relate to low sulphur diesel, gas oils and gas oils (diesel fuels) respectively containing esters derived by transesterification of vegetable oils, glycerol/fatty acid esters and lower alkyl esters of a mixture of saturated and unsaturated fatty acids derived from oleaginous seeds respectively as a lubricity improving agent. In each case there is no mention of low sulphur gasolines, especially gasolines having a sulphur content of < 30 ppm.
WO99/00467 describes a fuel composition of improved lubricity comprising a spark ignition fuel and an alkanolamide of a fatty acid or a modified fatty acid having a maximum sulphur content of 0.05% based on mass. However, no gasolines are mentioned and all of the examples relate to diesels, especially Swedish Class I low sulphur diesel fuel. There is also no reference to the bromine number or UV absorbance of the fuels tested or claimed. It has now been found that the efficacy of the friction reducing additives can be significantly improved by mixing the same with fuels of specific, predetermined characteristics.
Accordingly, the present invention is a composition comprising (i) a low sulphur gasoline having a sulphur content of less than 30 ppm, a bromine number of less than about 10 and an ultraviolet absorbance at 319 nm below 0.15 and (ii) an effective amount of an ashless friction reducing additive which is a fatty acid having 10-30 carbon atoms or a derivative thereof.
The gasoline should have a bromine number (which is related to the amount of olefins in the fuel) below 10, suitably below 5 and preferably below 4.5. Furthermore, the gasoline should have a sulphur content below 30 ppm, suitably below 20 ppm and preferably below 10 ppm. Again the UV absorbance of the fuel at 319 nm should be below 0.1 , suitably below 0.07 and preferably below 0.05.
The ashless friction reducing additive in the composition is suitably a liquid at room temperature and pressure and is selected from C10-C30 fatty acids, preferably a C10-C24 fatty acid, or a derivative thereof and mixtures thereof. Such ashless friction reducing additives are suitably derived from naturally occurring fats and oils and the preferred derivatives are suitably selected from the alkylamine salts, alkyl amides and alkyl esters of such acids and oligomers thereof. An example of an alkyl amine carboxylate salt is n- butylamine oleate or a derivative thereof and an example of a naturally occurring fatty acid is a substance comprising a fatty acid, a tall oil fatty acid or derivatives thereof.
n-Butylamine oleate has the formula:
CH3-(CH2)7-CH:CH-(CH2)7-C(O)O" +NH3C4H9
One such n-butylamine oleate is commercially sold as a friction modifier as RS124 by Bitrez Ltd.
The substance comprising fatty acids may be either 100% fatty acids, or substantially 100% fatty acids, or may be a mixture of fatty acids and/or tall oil acids or derivatives thereof. Such a mixture suitably contains at least 30% w/w, preferably at least 50% w/w of fatty acids. An example of a suitable commercially available substance containing fatty acids is TOLAD® 9103 (ex Baker-Petrolite Ltd). The friction reducing additive is used in an amount sufficient to provide effective lubricity to the composition. The friction reducing additive is suitably used in an amount of less than 1000 mg per kilogram of base fuel in the composition, preferably from 1 to 500 mg and more preferably from about 5 to 100 mg per kg of base fuel in the composition. It has been found that a gasoline with these characteristics is much more responsive to the amount of the ashless friction reducing agent specified above added than conventional fuels which do not possess these characteristics. A typical example of such a gasoline is the so called "Rotterdam gasoline" which suitably has a final boiling point below 200°C, preferably about 185°C. The ashless friction reducing additive may be part of an additive concentrate comprising a number of additives. In the additive concentrate, the amount of the friction reducing additive is suitably from 0.2-25% w/w, preferably from 0.5-20% w/w and more preferably from 3 to 15% w/w. On the basis of the total concentrate, the treat level of the friction reducing additive in the gasoline is suitably from 4-200 ppm, preferably from 10-100 ppm and more preferably from 25-75 ppm.
The present invention is further illustrated with reference to the following Examples and comparative tests:
EXAMPLES:
The following fuels with varying degrees of bromine numbers, sulphur content and UV absorbance at 319 nm were tested for their responsiveness to a lubricity additive. Of these, both the Rotterdam and the Neste 95UL base gasolines show comparable sulphur contents, yet the Rotterdam fuel (which has a final boiling point of 186.2°C) is more responsive to lubricity additive. This responsiveness, as measured by the percentage reduction in friction relative to base fuel (Table 2) is linked to the fuel's substantially lower bromine number and UV absorption at 319 nm. (Table 1) (Note: the measure of UV absorbance and bromine number are both dimensionless quantities).
TABLE 1
*Indicates a test fuel not according to the invention. The above fuels were tested at various treat rates to determine the change in coefficient of friction and the mean friction values and the results are tabulated in Tables 2 and 3 below:
TABLE 2
Mean FC= mean friction coefficient
ΔFC= Mean FC (base fuel)- Mean FC (additised fuel)
%ΔFC= [Mean FC (base fuel)- Mean FC (additised fuel)] x 100/ Mean FC (base fuel)
*These are by weight ie mg/Kg
#Fuels according to the invention.
TABLE 3
n-BAO - n-butylamine oleate; Tolad® FC-Friction Coefficient

Claims

CLAIMS:
1. A composition comprising (i) a low sulphur gasoline having a sulphur content of less than 30 ppm, a bromine number of less than 10 and an ultraviolet absorbance at 319 nm below 0.15 and (ii) an effective amount of an ashless friction reducing additive which is a fatty acid having 10-30 carbon atoms or a derivative thereof.
2. A composition according to Claim 1 wherein the gasoline has a bromine number below 5 ppm.
3. A composition according to any one of the preceding Claims wherein the gasoline has a sulphur content below 20 ppm.
4. A composition according to any one of the preceding Claims wherein the gasoline has an UV absorbance at 319 nm of below 0.07
5. A composition according to any one of the preceding Claims wherein the ashless friction reducing additive is selected from one or more C10-C30 fatty acids or derivatives thereof.
6. A composition according to Claim 5 wherein the fatty acid is derived from naturally occurring fats and oils and oligomers thereof.
7. A composition according to any one of the preceding Claims 1-5 wherein the ashless friction reducing additive is an alkylamine salts of a fatty acid derived from naturally occurring fats and oils and oligomers thereof.
8. A composition according to any one of the preceding Claims 1-5 wherein the ashless friction reducing additive is an alkyl amides of a fatty acid derived from naturally occurring fats and oils and oligomers thereof.
9. A composition according to any one of the preceding Claims 1-5 wherein the ashless friction reducing additive is an alkyl ester of a fatty acid derived from naturally occurring fats and oils and oligomers thereof.
10. A composition according to Claim 7 wherein the alkyl amine carboxylate salt is n-butylamine oleate as shown in the formula below or a derivative thereof
CH3-(CH2)7-CH:CH-(CH2)7-C(O)O" ^ H3C4H 9
11. A composition according to Claim 6 wherein the long chain fatty acid or a derivative thereof is a substance comprising tall oil acid or derivatives thereof.
12. A composition according to Claim 1 1 wherein the substance containing fatty acid is TOLAD® 9103 (ex Petrolite Ltd).
13. A composition according to any one of the preceding Claims wherein the friction reducing additive is present in said composition in an amount sufficient to provide effective lubricity to the composition.
14. A composition according to any one f the preceding Claims wherein the friction reducing additive is present in said composition in an amount of less than 1000 mg per kilogram of base fuel in the composition.
15. A composition according to any one of the preceding Claims wherein the treat level of the friction reducing additive is from 4-200 ppm based on the gasoline.
16. A composition according to any one of the preceding Claims wherein the treat level of the friction reducing additive is from 10-100 ppm based on the gasoline.
17. A composition according to any one of the preceding Claims wherein the treat level of the friction reducng additive is from 25-75 ppm based on the gasoline.
EP01942375A 2000-01-14 2001-01-12 Gasoline composition Expired - Lifetime EP1252267B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB0000915A GB2358192A (en) 2000-01-14 2000-01-14 Fatty acids or derivatives thereof as lubricity enhancers in low sulphur fuels
GB0000915 2000-01-14
PCT/EP2001/000331 WO2001051592A1 (en) 2000-01-14 2001-01-12 Gasoline composition

Publications (2)

Publication Number Publication Date
EP1252267A1 true EP1252267A1 (en) 2002-10-30
EP1252267B1 EP1252267B1 (en) 2006-04-26

Family

ID=9883747

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01942375A Expired - Lifetime EP1252267B1 (en) 2000-01-14 2001-01-12 Gasoline composition

Country Status (11)

Country Link
US (1) US20030154650A1 (en)
EP (1) EP1252267B1 (en)
JP (1) JP2003519718A (en)
AT (1) ATE324425T1 (en)
CA (1) CA2396425A1 (en)
DE (1) DE60119078T2 (en)
DK (1) DK1252267T3 (en)
ES (1) ES2263627T3 (en)
GB (1) GB2358192A (en)
PT (1) PT1252267E (en)
WO (1) WO2001051592A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004210984A (en) * 2003-01-06 2004-07-29 Chevron Texaco Japan Ltd Fuel oil composition and fuel additive
JP7495942B2 (en) 2019-02-07 2024-06-05 シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ Fuel Composition Having Lubricity Additive
EP4105301A1 (en) 2021-06-15 2022-12-21 Basf Se New gasoline additive packages

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7713482A (en) * 1977-12-06 1979-06-08 Beverolfabrieken PROCESS FOR THE PREPARATION OF A HYDROCARBON FUEL WITH LUBRICATING ACTION.
CA2045455C (en) * 1990-07-13 2002-04-02 John Vincent Hanlon Motor fuels of enhanced properties
US5113803A (en) * 1991-04-01 1992-05-19 Ethyl Petroleum Additives, Inc. Reduction of Nox emissions from gasoline engines
GB9301119D0 (en) * 1993-01-21 1993-03-10 Exxon Chemical Patents Inc Fuel composition
IT1270954B (en) * 1993-07-21 1997-05-26 Euron Spa DIESEL COMPOSITION
CA2194572A1 (en) * 1994-05-31 1995-12-07 William C. Orr Vapor phase combustion methods and compositions
GB9514480D0 (en) * 1995-07-14 1995-09-13 Exxon Chemical Patents Inc Additives and fuel oil compositions
JP3379866B2 (en) * 1995-04-24 2003-02-24 花王株式会社 Gas oil additive and gas oil composition
GB2307246B (en) * 1995-11-13 2000-04-12 Ethyl Petroleum Additives Ltd Fuel additive
GB2307247B (en) * 1995-11-13 1999-12-29 Ethyl Petroleum Additives Ltd Fuel additive
ATE202595T1 (en) * 1995-12-22 2001-07-15 Exxonmobil Res & Eng Co PETROL ADDITIVE CONCENTRATE
JPH09255973A (en) * 1996-03-25 1997-09-30 Oronaito Japan Kk Additive for gas oil and gas oil composition
EP0829527A1 (en) * 1996-09-12 1998-03-18 Exxon Research And Engineering Company Additive concentrate for fuel compositions
US5730029A (en) * 1997-02-26 1998-03-24 The Lubrizol Corporation Esters derived from vegetable oils used as additives for fuels
US6562086B1 (en) * 1997-06-26 2003-05-13 Baker Hughes Inc. Fatty acid amide lubricity aids and related methods for improvement of lubricity of fuels
JP4383660B2 (en) * 1998-01-13 2009-12-16 ベイカー ヒューズ インコーポレイテッド Compositions and methods for improving the lubricity of fuels
US6132479A (en) * 1998-05-04 2000-10-17 Chevron U.S.A. Inc. Low emission, non-oxygenated fuel composition
US6511519B1 (en) * 2000-09-29 2003-01-28 Chevron Oronite Company Llc Fuel additive compositions containing a mannich condensation product, a poly(oxyalkylene) monool, and a carboxylic acid

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0151592A1 *

Also Published As

Publication number Publication date
GB2358192A (en) 2001-07-18
WO2001051592A1 (en) 2001-07-19
PT1252267E (en) 2006-09-29
US20030154650A1 (en) 2003-08-21
EP1252267B1 (en) 2006-04-26
ATE324425T1 (en) 2006-05-15
DE60119078D1 (en) 2006-06-01
CA2396425A1 (en) 2001-07-19
DE60119078T2 (en) 2006-11-30
DK1252267T3 (en) 2006-08-28
GB0000915D0 (en) 2000-03-08
ES2263627T3 (en) 2006-12-16
JP2003519718A (en) 2003-06-24

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