EP0773279B1 - Kraftstoffzusatz - Google Patents

Kraftstoffzusatz Download PDF

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Publication number
EP0773279B1
EP0773279B1 EP19960308194 EP96308194A EP0773279B1 EP 0773279 B1 EP0773279 B1 EP 0773279B1 EP 19960308194 EP19960308194 EP 19960308194 EP 96308194 A EP96308194 A EP 96308194A EP 0773279 B1 EP0773279 B1 EP 0773279B1
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fuel
ester
acid
use according
group
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EP0773279A1 (de
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Robert Quigley
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Afton Chemical Ltd
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Afton Chemical Ltd
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    • 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
    • C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • 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
    • C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
    • 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
    • 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
    • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • 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
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • 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
    • C10L1/16—Hydrocarbons
    • C10L1/1608—Well defined compounds, e.g. hexane, benzene
    • 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
    • C10L1/16—Hydrocarbons
    • C10L1/1616—Hydrocarbons fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine
    • 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
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
    • C10L1/1824—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms mono-hydroxy
    • 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
    • C10L1/23—Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites
    • C10L1/231—Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites nitro compounds; nitrates; nitrites
    • 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
    • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • C10L1/233—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring containing nitrogen and oxygen in the ring, e.g. oxazoles
    • C10L1/2335—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring containing nitrogen and oxygen in the ring, e.g. oxazoles morpholino, and derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
    • C10L1/2387—Polyoxyalkyleneamines (poly)oxyalkylene amines and derivatives thereof (substituted by a macromolecular group containing 30C)

Definitions

  • the present invention relates to the use of certain compounds to improve the lubricating properties of low sulfur-content fuels and to fuels containing the compounds.
  • Sulfur contained in fuel for example middle distillate fuels such as diesel fuel and jet fuel, is said to constitute a serious environmental hazard.
  • middle distillate fuels such as diesel fuel and jet fuel
  • strict regulations limiting the amount of sulfur which may be present in such fuels have been introduced.
  • fuels having a suitably low sulfur content exhibit very poor inherent lubricity and this can lead to problems when the fuel is used.
  • the use of low sulfur fuel in diesel engines frequently results in damage to the fuel injector pump which relies on the natural lubricating properties of the fuel to prevent component failure. There is therefore a need to improve the lubricating properties of low sulphur fuels.
  • GB-A-1074232 discloses reaction products of polyamines and dicarboxylic acid esters and mixtures of a polyamine or hydroxyamine and a dicarboxylic acid ester in improving the lubricity of jet fuels.
  • WO 95/33805 teaches that the lubricity of low sulphur fuels is enhanced by incorporation of a cold flow improver.
  • US-A-5352377 relates to reaction products of hydrocarbyl substituted succinic anhydrides and aminoalcohols as antiwear, antirust and corrosion inhibiting additives in hydrocarbonaeous media.
  • low sulfur-content fuel is intended to mean fuels having a sulfur content of 0.05% by weight or less and, more especially, 0.005% by weight or less.
  • the present invention provides the use, as an additive for improving the lubricity of a fuel having a sulphur content of 0.05% by weight or less, of a carboxylic acid ester of an alkanolamine, which does not contain any hydroxy-substitution in the acid backbone, wherein the alkanolamine is of formula: R 1 [N(R 1 ) (CH 2 ) p ] q Y in which p is 2 to 10, q is 0 to 10, Y is -N(R 1 ) 2 , 4-morpholinyl or 1-piperazinyl N-substituted by a group R 1 or a group - [(CH 2 ) p N(R 1 )] q R 1 in which p and q are as defined above, and each substituent R 1 is independently selected from a groups of formula: -(R 2 O) r R 3 in which r is 0 to 10, R 2 is an alkylene group having from 2 to 6 carbon atoms and R 3
  • Examples of fuels in which the additive compounds may be used include low sulfur middle distillate fuels such as diesel and jet fuels and bio-diesel fuel.
  • middle distillate fuels such as diesel and jet fuels and bio-diesel fuel.
  • the latter is derived from a petroleum or vegetable source or mixture thereof and typically contains vegetable oils or their derivatives, such as esters produced by saponification and re-esterification or transesterification.
  • Middle distillate fuels are usually characterised as having a boiling range of 100 to 500°C, more typically from 150 to 400°C.
  • ester used in the present invention may be used alone or in combination with other esters as described herein.
  • the acid used in the present invention is one which does not contain any hydroxy-substitution in the acid backbone.
  • the acid typically contains up to 60 carbon atoms. More typically, it has from 10 to 60 carbon atoms.
  • the acid may be a mono- or poly-carboxylic acid or a dimerized acid. When mono-carboxylic acids are used they typically contain 10 to 40 carbon atoms, more commonly 10 to 30 and especially 12 to 24 carbon atoms. Examples of such include aliphatic fatty acids such as lauric, myristic, heptadecanoic, palmitic, stearic, oleic, linoleic, linolenic, nonadecanoic, arachic or behenic acid.
  • poly-carboxylic acids such as di- or tri-carboxylic acids, they typically contain 3 to 40 carbon atoms, more commonly 3 to 30 and especially 3 to 24 carbon atoms.
  • examples of this kind of poly-carboxylic acid include dicarboxylic acids such as succinic, glutaric, adipic, suberic, azelaic or sebacic acid, and tricarboxylic acids such as 1,3,5-cyclohexane tricarboxylic acid and tetracarboxylic acids such as 1,2,3,4-butane tetracarboxylic acid.
  • the acid is a dimerized fatty acid, for example a dimer acid of oleic and linoleic acids.
  • this dimer exists as a mixture of 2% by weight monomer, 83% by weight dimer and 15% by weight of trimer and possibly higher acids.
  • the preferred dimer acid, as well as the other acids described above, are commercially available or may be prepared by the application or adaption of known techniques.
  • the alkanolamine used to form the ester used in the present invention has the formula gives above.
  • the alkanolamine is one which does not contain any hydrogen-bearing nitrogen atoms. The presence of free hydrogen atoms would be expected to lead to the formation of an amide on reaction with the fatty acid.
  • R 1 is alkyl it contains from 1 to 6 carbon atoms, preferably 2 to 4 carbon atoms.
  • R 2 is an alkylene group having 2 to 6 carbon atoms, preferably 2 to 4 carbon atoms.
  • R 3 is an hydroxyalkyl group having 2 to 6 carbon atoms, preferably 2 to 4 carbon atoms. The hydroxyalkyl group typically contains 1 to 3 hydroxy groups.
  • R 3 is typically a mono-hydroxyalkyl group, for example hydroxyethyl or hydroxypropyl.
  • R 3 is typically a mono- or poly-hydroxyalkyl group having up to 4 hydroxy groups, for example hydroxyethyl, hydroxypropyl or a 1-hydroxy-2,2-bis(hydroxymethyl)ethyl group.
  • the values p, q and r take are selected independently. This means for example that when q is greater than zero, p may take different values in each repeat unit. Also, when r is greater than zero, R 2 may be the same or different in each ether repeat unit.
  • the alkanolamines which may be used to form the ester are commercially available or may be made by the application or adaptation of known techniques.
  • the alkanolamines in which r is 1 or more i.e. those containing an ether of polyether linkage, can be prepared by reaction of a suitable amine, morpholine or piperazine compound with a molar excess of one or more alkylene oxides.
  • R 2 and R 3 contain the same alkylene moiety.
  • R 2 and R 3 may contain the same or different alkylene groups.
  • alkanolamines of the above formula are used in which Y is -N(R 1 ) 2 , p is 2 and q is 0 to 3.
  • the alkanolamine is triethanolamine or triisopropanolamine or ethylene diamine or diethylene triamine in which each nitrogen atom is substituted by hydroxyethyl or hydroxypropyl groups.
  • Y is 4-morpholinyl or substituted 1-piperazinyl
  • p is 2 to 6
  • q is 0 or 1.
  • alkanolamines include aminoethylpiperazine, bis-(aminoethyl)piperazine or morpholine, N-substituted by an hdyroxypropyl group.
  • esters described may be made by the application or adaptation of known techniques, or are commercially available ready for use.
  • the ester contains at least one free carboxylic group in the acid-derived moiety.
  • This kind of compound may be formed using as the starting acid a polycarboxylic acid, for example a dicarboxylic acid or a dimer or trimer acid.
  • the number of moles of acid and alkanolamine which are reacted is controlled such that the resulting ester contains at least one free carboxylic functional group in the acid derived-moiety.
  • an acid having two carboxyl functions such as a dicarboxylic or dimer acid, the mole ratio could be about 1:1.
  • the ester contains at least one free carboxylic group in the acid moiety, it may be used as is or it may be derivatised further to enhance its properties.
  • the kind of compound used to derivatise the ester further usually depends upon the kind of acid used initially to form the ester and the properties of the ester it is desired to influence. For example, it is possible to increase the fuel-solubility of the ester by introducing into the ester molecule a fuel-solubilizing species. As an example of such, long-chain alkyl or alkenyl groups may be mentioned.
  • ester may be reacted with an alcohol, ROH or an amine, RNH 2 in which R is alkyl or alkenyl having up to 30 carbon atoms, for example 4 to 30 carbon atoms.
  • R is alkyl or alkenyl having up to 30 carbon atoms, for example 4 to 30 carbon atoms.
  • the number of carbon atoms in the alkyl or alkenyl group may depend upon the number of carbon atoms in the ester itself.
  • These compounds react with the free carboxylic functional group(s) of the ester to form a further ester linkage or an amide linkage.
  • Examples of particular alcohols and amides which may be used include oleyl alcohol and oleyl amine.
  • ester it is possible to further derivatise the ester to introduce one or more polar head groups.
  • compounds which may be used to introduce one or more polar head groups include polyamines (e.g. ethylene diamine and diethylene triamine), alkanolamines such as those described above, monohydric alcohols (e.g.
  • ethanol and propanol and polyhydric alcohols
  • polyhydric alcohols e.g.ethylene glycol, diethylene glycol, triethylene glycol, dipropylene glycol, glycerol, arabitol, sorbitol, mannitol, pentaerythritol, sorbitan, 1,2-butanediol, 2,3-hexanediol, 2,4-hexanediol, pinacol and 1,2-cyclohexanediol).
  • polyhydric alcohols e.g.ethylene glycol, diethylene glycol, triethylene glycol, dipropylene glycol, glycerol, arabitol, sorbitol, mannitol, pentaerythritol, sorbitan, 1,2-butanediol, 2,3-hexanediol, 2,4-hexanediol, pinacol and 1,2-cyclohexanedi
  • the ester is one derived from a dimer or trimer acid
  • the ester is further derivatised to introduce fuel-solubilising species.
  • Dimer and trimer acid esters tend already to contain in the acid backbone long chain alkyl or alkenyl moieties sufficient to provide adequate fuel-solubility.
  • ester which is derivatised further
  • the same final species can be formed by first reacting free carboxyl functional group(s) of a polycarboxylic acid to introduce oil-solubilising or polar head groups and then reacting the resultant product with the kind of alkanolamine described above to form the ester.
  • the product formed after being derivatised contains at least one free carboxylic group in the acid-derived moiety such that ester formation with the alkanolamine is still possible.
  • the further derivatives are commercially available or may be made by the application or adaptation of known techniques.
  • the ester is present in the fuel at a concentration of from 10 to 1000 ppm, preferably 50 to 500 ppm, more preferably still from 100 to 400 ppm.
  • concentration falls within the typical range quoted.
  • the present invention further provides a fuel having a sulfur content of 0.05% by weight or less, comprising a carboxylic acid ester as defined above.
  • the base fuel may be a middle distillate fuel or a bio-diesel fuel as described above.
  • the additive may be provided as a concentrate for dilution with fuel.
  • a concentrate typically comprises from 99 to 1% by weight additive and from 1 to 99% by weight of solvent or diluent for the additive which solvent or diluent is miscible and/or capable of dissolving in the fuel in which the concentrate is to be used.
  • the solvent or diluent may, of course, be the low sulfur fuel itself.
  • examples of other solvents or diluents include white spirit, kerosene, alcohols (e.g.
  • 2-ethyl hexanol, isopropanol and isodecanol high boiling point aromatic solvents (e.g. toluene and xylene) and cetane improvers (e.g. 2-ethyl hexylnitrate).
  • high boiling point aromatic solvents e.g. toluene and xylene
  • cetane improvers e.g. 2-ethyl hexylnitrate
  • the concentrate or fuel may also contain other fuel additives in the appropriate proportions thereby providing a multifunctional fuel additive package.
  • fuel additives which may be used include fuel stabilisers, dispersants, detergents, antifoams, cold flow improvers, cetane number improvers, antioxidants, corrosion inhibitors, antistatic additives, biocides, dyes, smoke reducers, catalyst life enhancers and demulcifiers.
  • the total treat rate for multifunctional formulations containing the lubricity enhancing additive compounds described is typically 200 to 2000 ppm, more usually 300 to 1200 ppm.
  • the invention also provides a method of reducing fuel pump wear in an engine which operates on a fuel having a sulphur content of 0.05% by weight or less, which method comprises using a fuel described herein.
  • the fuel may be used to reduce wear in rotary and in-line fuel pumps, for example as found in diesel engines, or in fuel transfer pumps. The latter are positioned between the fuel tank and the high pressure fuel pump.
  • the fuel is particularly well suited for reducing wear in fuel injector pumps.
  • the fuel may also be used to reduce wear in the latest fuel injector units which combine fuel pump and injector mechanisms.
  • the invention is particularly well-suited to the operation of diesel and jet engines.
  • the present invention is illustrated in the following Example.
  • the efficacy of a number of diesel fuels was assessed using the Scuffing BOCLE (ball-on- cylinder lubricity evaluator) test.
  • This test is a modification of the standard aviation BOCLE test (ASTM method D5001: "Standard Test Method for Measurement of Lubricity of Aviation Turbine Fuels by the Ball-on-Cylinder Lubricity Evaluator (BOCLE)", ASTM Standards, Section 5, Vol 3, 1993) in which a load of 1 kg is applied to a fixed ball in contact with a rotating cylinder lubricated by the test fuel.
  • fuel lubricity is assessed by measuring the size of the wear scar on the fixed ball resulting from the constant load contact with the cylinder.
  • the standard BOCLE test suffers the disadvantage that the applied load is not high enough to model the type of severe wear failure that occurs in the field, for example in fuel injector pumps.
  • the Scuffing BOCLE test offers the advantage over the standard test of allowing discrimination and ranking of fuels of differing lubricity.
  • the Scuffing test also simulates more closely the severe modes of wear failure encountered in fuel pumps than other fuel lubricity tests which run under mild wear conditions.
  • the Scuffing BOCLE test therefore provides results which are more representative of how the fuel would behave in service.
  • the load at which wear failure occurs is referred to as the scuffing load and is a measure of the inherent lubricity of the fuel.
  • the scuffing load is primarily identified by the size and appearance of the wear scar on the ball, which is considerably different in appearance to that found under milder non-scuffing conditions. Fuels giving a high scuffing load on failure have better lubricating properties than fuels giving a low scuffing load on failure.
  • the base fuel used was a Class 2 Scandinavian diesel fuel. This is a diesel fuel having a sulfur content of 0.005% by weight.
  • the composition and distillation profile of this fuel are shown below. Density at 15°C (IP 160), g/ml 0.8160 Paraffins, %vol 89.6 Olefins, %vol 0.7 Aromatics, %vol 9.7 Distillation Characteristics (IP 123)
  • IP 160 Density at 15°C
  • IP 160 g/ml 0.8160 Paraffins
  • %vol 89.6 Olefins %vol 0.7 Aromatics
  • %vol 9.7 Distillation Characteristics IP 123
  • Initial B.P. °C 184 5% 200 10% 204 20% 212 30% 217 40% 223 50% 228 60% 235 70% 243 80% 251 90 % 263 95% 269
  • the dimer acid used is formed from oleic and linoleic acids and is commercially available from Union Camp under the name Unidyme RTM 22. In the table above:

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  • 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)
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  • Liquid Carbonaceous Fuels (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)

Claims (11)

  1. Verwendung eines Carbonsäure esters eines Alkanolamins, der keine Fiydroxysubstitution in der Säurehauptkette aufweist, als Additiv zur Verbesserung der Schinierfähigkeit eines Treibstoffs mit einem Schwefelgehalt von 0,05 Gew.-% oder weniger, wobei das Alkanolamin die Formel

            R1[N(R1)(CH2)p]qY

    hat, in der p 2 bis 10 ist, q 0 bis 10 ist, Y -N(R1)2, 4-Morpholinyl oder 1-Piperazinyl ist, N-substituiert durch eine Gruppe R1 oder eine Gruppe -[(CH2)pN(R1)qR1, in der p und q wie vorstehend definiert sind, und jeder Substituent R1 unabhängig ausgewählt ist aus Gruppen der Formel

            -(R2O)rR3,

    in der r 0 bis 10 ist, R2 eine Alkylengruppe mit 2 bis 6 Kohlenstoffatomen ist und R3 eine Hydroxyalkylgruppe mit 2 bis 6 Kohlenstoffatomen ist.
  2. Verwendung nach Anspruch 1, bei der der Treibstoff ein Dieseltriebstoff, Düsentreibstoff oder Biodieseltreibstoff ist.
  3. Verwendung nach Anspruch 1 oder 2, bei der die Säure 14 bis 60 Kohlenstoffatome aufweist.
  4. Verwendung nach einem der Ansprüche 1 bis 3, bei der die Säure eine Dimersäure von Olein- und Linolsäure ist.
  5. Verwendung nach einem der vorstehenden Ansprüche, bei der das Alkanolamin Triethanolamin oder Triisopropanolamin oder Ethylendiamin oder Diethylentriamin ist, in dem jedes Stickstoffatom durch Hydroxyethyl- oder Hydroxypropylgruppen substituiert ist.
  6. Verwendung nach einem der Ansprüche 1 bis 4, bei der das Alkanolamin Aminoethylpiperazin, bis-(Aminoethyl)piperazin oder Morpholin ist, das jeweils durch eine Hydroxypropylgruppe N-substituiert ist.
  7. Verwendung nach einem der vorstehenden Ansprüche, bei der der Ester mindestens eine freie carboxylfunktionelle Gruppe in der von der Säure abgeleiteten Komponente enthält.
  8. Verwendung nach Anspruch 7, bei der der Ester außerdem durch die Reaktion mit einer Verbindung, die eine Treibstoff solubilisierende Spezies in das Estermolekül einführt, oder durch die Reaktion mit einer Verbindung, die eine polare Kopfgruppe in das Estermolekül einfuhrt, derivatisiert wird.
  9. Verwendung nach einem der vorstehenden Ansprüche, bei der der Ester im Treibstoff in einer Konzentration von 10 bis 1000 ppm vorliegt.
  10. Treibstoff mit einem Schwefelgehalt von 0,05 Gew.-% oder weniger, der einen wie in Anspruch 1 oder einem der Ansprüche 3 bis 8 definierten Carbonsäureester umfasst,
  11. Verfahren zur Verringerung des Verschleißes der Treibstoffpumpe in einem Motor, der mit Treibstoff mit einem Schwefelgehalt von 0,05 Gew.-% oder weniger betrieben wird, wobei das Verfahren die Verwendung eines Treibstoffs wie in Anspruch 10 definiert umfasst.
EP19960308194 1995-11-13 1996-11-13 Kraftstoffzusatz Expired - Lifetime EP0773279B1 (de)

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Application Number Priority Date Filing Date Title
GB9523164A GB2307246B (en) 1995-11-13 1995-11-13 Fuel additive
GB9523164 1995-11-13

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EP0773279A1 EP0773279A1 (de) 1997-05-14
EP0773279B1 true EP0773279B1 (de) 2006-08-09

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GB9523164D0 (en) 1996-01-17
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GB2307246B (en) 2000-04-12

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