EP1252267B1 - Benzinzusammensetzung - Google Patents

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Publication number
EP1252267B1
EP1252267B1 EP01942375A EP01942375A EP1252267B1 EP 1252267 B1 EP1252267 B1 EP 1252267B1 EP 01942375 A EP01942375 A EP 01942375A EP 01942375 A EP01942375 A EP 01942375A EP 1252267 B1 EP1252267 B1 EP 1252267B1
Authority
EP
European Patent Office
Prior art keywords
gasoline
composition according
friction reducing
reducing additive
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.)
Expired - Lifetime
Application number
EP01942375A
Other languages
English (en)
French (fr)
Other versions
EP1252267A1 (de
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/de
Application granted granted Critical
Publication of EP1252267B1 publication Critical patent/EP1252267B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • 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
    • 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
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic 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
    • 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
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224—Amides; 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.
  • EP-A-0 829 527 discloses additives for gasolines containing ashless friction modifiers among other constituents.
  • 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.
  • the present invention as disclosed in the wording of independent claim 1 is a composition
  • 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) less than 1000 mg per kg of the low sulphur gasoline of an ashless friction reducing additive which is a fatty acid having 10-30 carbon atoms derived from naturally occurring fats and oils or a derivative thereof selected from the alkylamine salts, alkylamides and alkylesters of such acids and oligomers thereof.
  • the gasoline has 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 has 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 can preferably be below 0.1, suitably below 0.07 and more 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 derived from naturally occurring fats and oils and the derivatives 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 and an example of another naturally occurring fatty acid is a substance comprising a fatty acid, a tall oil fatty acid.
  • n-Butylamine oleate has the formula: CH 3 -(CH 2 ) 7 -CH:CH-(CH 2 ) 7 -C(O)O - + NH 3 C 4 H 9
  • 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 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.
  • 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.
  • 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.

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)

Claims (15)

  1. Zusammensetzung, die (i) schwefelarmes Benzin mit einem Schwefelgehalt von weniger als 30 ppm, einer Bromzahl von weniger als 10 und einer Ultraviolett-Extinktion bei 319 nm unter 0,15 und (ii) weniger als 1000 mg aschefreies Reibungsverminderungsadditiv pro kg des schwefelarmen Benzins umfasst, welches eine Fettsäure mit 10 bis 30 Kohlenstoffatomen, die von natürlich vorkommenden Fetten oder Ölen abgeleitet ist, oder ein Derivat davon ausgewählt aus den Alkylaminsalzen, Alkylamiden und Alkylestern derartiger Säuren und Oligomeren davon ist.
  2. Zusammensetzung nach Anspruch 1, bei der das Benzin eine Bromzahl unter 5 ppm hat.
  3. Zusammensetzung nach einem der vorhergehenden Ansprüche, bei der das Benzin einen Schwefelgehalt unter 20 ppm hat.
  4. Zusammensetzung nach einem der vorhergehenden Ansprüche, bei der das Benzin eine UV-Extinktion bei 319 nm von unter 0,07 hat.
  5. Zusammensetzung nach einem der vorhergehenden Ansprüche, bei der die Fettsäure von natürlich vorkommenden Fetten und Ölen und Oligomeren davon abgeleitet ist.
  6. Zusammensetzung nach einem der vorhergehenden Ansprüche, bei der das aschefreie Reibungsverminderungsadditiv Alkylaminsalz von Fettsäure, die von natürlich vorkommenden Fetten und Ölen abgeleitet ist, und Oligomeren davon ist.
  7. Zusammensetzung nach einem der Ansprüche 1 bis 4, bei der das aschefreie Reibungsverminderungsadditiv Alkylamid von Fettsäure, die von natürlich vorkommenden Fetten und Ölen abgeleitet ist, und Oligomeren davon ist.
  8. Zusammensetzung nach einem der vorhergehenden Ansprüche 1 bis 4, bei der das aschefreie Reibungsverminderungsadditiv Alkylester von Fettsäure, die von natürlich vorkommenden Fetten und Ölen abgeleitet ist, und Oligomeren davon ist.
  9. Zusammensetzung nach Anspruch 6, bei der das Alkylamincarboxylatsalz n-Butylaminoleat wie in der folgenden Formel gezeigt oder ein Derivat davon ist:

            CH3-(CH2)7-CH:CH-(CH2)7-C(O)O- +NH3C4H9

  10. Zusammensetzung nach einem der Ansprüche 1 bis 4, bei der die langkettige Fettsäure oder ein Derivat davon eine Substanz ist, die Tallölsäure oder Derivate davon umfasst.
  11. Zusammensetzung nach einem der vorhergehenden Ansprüche, wobei die Behandlungskonzentration des Reibungsverminderungsadditivs 1 bis 500 mg pro kg Benzin beträgt.
  12. Zusammensetzung nach einem der vorhergehenden Ansprüche, bei der die Behandlungskonzentration des Reibungsverminderungsadditivs 4 bis 200 ppm ist, bezogen auf Benzin.
  13. Zusammensetzung nach einem der vorhergehenden Ansprüche, bei der die Behandlungskonzentration des Reibungsverminderungsadditivs 10 bis 100 ppm ist, bezogen auf Benzin.
  14. Zusammensetzung nach einem der vorhergehenden Ansprüche, bei der die Behandlungskonzentration des Reibungsverminderungsadditivs 25 bis 75 ppm ist, bezogen auf Benzin.
  15. Verfahren zur Verbesserung der Effizienz von in schwefelarmem Benzin verwendetem aschefreiem Reibungsverminderungsadditiv, bei dem Reibungsverminderungsadditiv, das Fettsäure mit 10 bis 30 Kohlenstoffatomen, die von natürlich vorkommenden Fetten und Ölen abgeleitet ist, oder ein Derivat davon ausgewählt aus den Alkylaminsalzen, Alkylamiden und Alkylestern dieser Säuren und Oligomeren davon ist, in einer Behandlungskonzentration von weniger als 1000 mg pro kg Benzin mit Benzin mit einem Schwefelgehalt von weniger als 30 ppm, einer Bromzahl von weniger als 10 und einer Ultraviolett-Extinktion bei 319 nm unter 0,15 kombiniert wird.
EP01942375A 2000-01-14 2001-01-12 Benzinzusammensetzung Expired - Lifetime EP1252267B1 (de)

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 EP1252267A1 (de) 2002-10-30
EP1252267B1 true EP1252267B1 (de) 2006-04-26

Family

ID=9883747

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01942375A Expired - Lifetime EP1252267B1 (de) 2000-01-14 2001-01-12 Benzinzusammensetzung

Country Status (11)

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

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4105301A1 (de) 2021-06-15 2022-12-21 Basf Se Neue benzinadditivpaket

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004210984A (ja) * 2003-01-06 2004-07-29 Chevron Texaco Japan Ltd 燃料油組成物および燃料添加剤
WO2020161265A1 (en) * 2019-02-07 2020-08-13 Shell Internationale Research Maatschappij B.V. Fuel composition with lubricity additives

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4105301A1 (de) 2021-06-15 2022-12-21 Basf Se Neue benzinadditivpaket
WO2022263254A1 (en) 2021-06-15 2022-12-22 Basf Se New gasoline additive packages

Also Published As

Publication number Publication date
US20030154650A1 (en) 2003-08-21
CA2396425A1 (en) 2001-07-19
DK1252267T3 (da) 2006-08-28
ES2263627T3 (es) 2006-12-16
DE60119078D1 (de) 2006-06-01
WO2001051592A1 (en) 2001-07-19
GB2358192A (en) 2001-07-18
EP1252267A1 (de) 2002-10-30
DE60119078T2 (de) 2006-11-30
JP2003519718A (ja) 2003-06-24
GB0000915D0 (en) 2000-03-08
ATE324425T1 (de) 2006-05-15
PT1252267E (pt) 2006-09-29

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