EP0859040B1 - L'utilisation d'additifs lubrifiants pour diminuer le mousse dans les fuels - Google Patents

L'utilisation d'additifs lubrifiants pour diminuer le mousse dans les fuels Download PDF

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Publication number
EP0859040B1
EP0859040B1 EP19980301109 EP98301109A EP0859040B1 EP 0859040 B1 EP0859040 B1 EP 0859040B1 EP 19980301109 EP19980301109 EP 19980301109 EP 98301109 A EP98301109 A EP 98301109A EP 0859040 B1 EP0859040 B1 EP 0859040B1
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EP
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Prior art keywords
fuel
additive
acid
composition
group
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Expired - Lifetime
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EP19980301109
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German (de)
English (en)
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EP0859040A1 (fr
Inventor
Gareth Charles Jeffrey
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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
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
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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
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/30—Organic compounds compounds not mentioned before (complexes)
    • C10L1/305—Organic compounds compounds not mentioned before (complexes) organo-metallic compounds (containing a metal to carbon bond)

Definitions

  • Foam control is a highly important consideration in the preparation of additive compositions for use in fuels of the middle distillate boiling range, such as gas oils, diesel fuels, gas turbine fuels, burner fuels and the like. If a fuel foams during transfer from one tank to another, it becomes difficult to control flow rates and volumes. Similarly, foaming during the filling of fuel tanks can pose various other problems, such as delivery of inadequate amounts of fuel to the tanks or conversely, overflowing and spillage of fuel at the filling site.
  • foam inhibitors such as polyacrylates and polysiloxanes have been proposed for use in diesel fuels and additive packages to be used in formulating finished diesel fuels.
  • European Patent Application No. 0 681 023 discloses fuel additive which comprise an overbased alkali or alkaline earth metal-containing detergent and a water-soluble polyether-polysiloxane copolymer as a foam inhibitor.
  • the additive may further comprise a corrosion inhibitor, a hydrocarbon-soluble ashless dispersant, a diluent and other conventional additives.
  • European Patent Application No. 0 476 196 relates to fuels and additive compositions which possess improved combustion characteristics, and form products with reduced acidity.
  • the additives may contain metal-containing basic detergent salts, fuel-soluble manganese carbonyl compounds, ashless dispersants and other conventional fuel additive components.
  • a lubricity additive can substantially improve the foam behaviour of fuels containing colloidally dispersed metal containing materials, such as overbased metal detergents or metal based emissions improving additives, in the presence of a wide range of antifoam agents.
  • a fuel additive composition which comprises as components thereof (i) a lubricity additive, (ii) at least one overbased metal detergent, and (iii) a siloxane antifoam agent which is insoluble in water at 25°C, and wherein components (i), (ii), and (iii) are present in amounts such that, when the composition is diluted with a base oil, the following amount of each component is present: component (i) 10-400 ppm component (ii) 1-100 ppm of the metal component component (iii) 1-30 ppm.
  • a fuel additive composition as above which further comprises (iv) a dispersant and/or (v) a metal based emissions improving additive, the weight ratio of (iv) to (iii) on an active ingredient basis is normally in the range of about 0.25 to about 300 parts by weight of (iv) per part by weight of (iii).
  • liquid hydrocarbon diluent especially a liquid highly aromatic hydrocarbon diluent
  • liquid alcohol diluent especially a liquid alcohol diluent
  • demulsifying agent or a corrosion inhibitor especially a liquid alcohol diluent
  • Still other embodiments include liquid fuel compositions, such as fuels boiling in the middle distillate boiling range, containing the components in accordance with any of the foregoing additive concentrates.
  • the lubricity additives of the present invention are preferably carboxylic acids, optionally substituted with at least one hydroxy group, or derivatives thereof.
  • the preferred carboxylic acid derivatives are carboxylic acid amides and carboxylic acid esters.
  • the hydroxy-substituted carboxylic acid or acid derivative may be used alone or in combination with any other hydroxy-substituted acid and/or acid derivative.
  • the hydroxy-substituted acid used in the present invention typically contains up to 60 carbon atoms.
  • the hydroxy-substituted acid may be a mono- or poly-carboxylic acid or a dimerized acid.
  • the preferred acid of this type is the fatty acid, ricinoleic acid.
  • hydroxy-substituted 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 hydroxy-substituted poly-carboxylic acid include ricinoleic, malic, tartaric and citric acids.
  • dimerized acids such compounds are referred to as dimer and trimer acids.
  • the dimerized acid typically contains 10 to 60, preferably 20 to 60 and most preferably 30 to 60, carbon atoms.
  • Such acids are prepared by dimerizing unsaturated acids and introducing a hydroxyl functionality.
  • Such acids typically consist of a mixture of monomer, dimer and trimer acid.
  • the acid is a hydroxy-substituted dimerized fatty acid, for example 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 adaptation of known techniques.
  • the lubricity additive compound(s) used may be in the form of a carboxylic acid derivative.
  • One kind of derivative which may be used is an ester of the acid with a polyhydric alcohol.
  • the polyhydric alcohol from which the ester may be derived typically contains from 2 to 7 carbon atoms.
  • suitable alcohols include alkylene glycols such as ethylene glycol, diethylene glycol, triethylene glycol and dipropylene glycol, glycerol, arabitol, sorbitol, mannitol, pentaerythritol, sorbitan, 1,2-butanediol, 2,3-hexanediol, 2,4-hexanediol, pinacol and 1,2-cyclohexanediol. These alcohols are readily available. Of the alcohols mentioned it is preferred to use glycerol or sorbitan.
  • the ester has at least one free hydroxyl group in the moiety derived from the polyhydric alcohol, i.e. not all of the hydroxyl groups of the polyhydric alcohol are esterified.
  • the use of glycerol monoricinoleate is particularly preferred.
  • Another carboxylic acid derivative which may be used is the ester of the hydroxy-substituted acid with an alkanolamine 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 alkyl groups having from 1 to 6 carbon atoms and a group of formula: -(R 2 O) r R 3 in which r is 0 to 10, R 2 is an alkylene group having 2 to 6 carbon atoms and R 3 is an hydroxyalkyl group having 2 to 6 carbon atoms, provided at least one group R 1 is -(R 2 O) r R 3 .
  • 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 acid.
  • the alkanolamines which may be used are commercially available or may be made by the application or adaptation of known methods.
  • Y is -N(R 1 ) 2 , p is 2 and q is 0 to 3. It is further preferred that each R 1 is a C 2-4 hydroxyalkyl group, C 2 or C 3 hydroxyalkyl being particularly preferred.
  • Specific examples of such compounds include triethanolamine, triisopropylamine and ethylene diamine and diethylene triamine in which each nitrogen atom is substituted by hydroxyethyl or hydroxypropyl groups.
  • alkanolamine Y is 4-morpholinyl or substituted 1-piperazinyl, q is 0 or 1 and p is from 2 to 6.
  • alkanolamines include aminoethylpiperazine, bis-(aminoethyl)piperazine and morpholine, N-substituted by an hydroxypropyl group.
  • alkanolamines are commercially available or may be made by the application or adaptation of known techniques.
  • an amide such as that formed by reaction of a hydroxy substituted carboxylic acid with ammonia or a nitrogen-containing compound 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 optionally 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 hydrogen and alkyl groups having 1 to 6 carbon atoms and a group of formula: -(R 2 O) r R 3 in which r is 0 to 15, R 2 is an alkylene group having 2 to 6 carbon atoms and R 3 is an hydroxyalkyl group having 2 to 6 carbon atoms, provided that at least one group
  • nitrogen- containing compound Y is -N(R 1 ) 2
  • p is 2 and q is 0 to 3.
  • examples of such compounds include diethanolamine, tris(hydroxymethyl)aminomethane, triethylene tetramine or diethylene triamine optionally N-substituted by two hydroxypropyl groups.
  • Y is 4-morpholinyl or optionally N-substituted 1-piperazinyl
  • p is 2 to 6
  • q is 0 or 1
  • each R 1 is hydrogen.
  • examples of such compounds include aminoethylpiperazine, bis-(aminoethyl)piperazine or morpholine.
  • the compounds used to form the acid amides are commercially available or may be made by the application or adaptation of known techniques.
  • alkanolamines and nitrogen-containing compounds of the above formulae in which r is 1 or more, i.e. those containing an ether or 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.
  • R 1 is alkyl the moiety 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 hydroxyl 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 preferred carboxylic acid amides are oleyl ethanolamide and oleyl diethanolamide.
  • the acid used in the present invention which does not contain any hydroxy-substitution in the acid backbone typically contains up to 60 carbon atoms.
  • the acid may be a mono- or poly-carboxylic acid or a dimerized acid.
  • mono-carboxylic acids 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.
  • dimerized acids it is also possible to use as the acid containing no hydroxy substitution in the backbone, dimerized acids.
  • dimer and trimer acids When used the dimerized acid typically contains 10 to 60, preferably 20 to 60 and most preferably 30 to 60, carbon atoms.
  • Such acids are prepared by dimerizing unsaturated acids and typically consist of a mixture of monomer, dimer and trimer acid.
  • the acid is a dimerized fatty acid, for example of oleic and linoleic acids. Typically 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 adaptation of known techniques.
  • the carboxylic acids containing no hydroxy substitution can be derivatized by reaction with an alkanolamine.
  • the alkanolamine is typically of formula: R 1 [N(R 1 )(CH 2 ) p ] q Y in which p is 2 to 10, preferably 2 or 3, q is 0 to 10, preferably 0 to 5, 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 alkyl groups having from 1 to 6 carbon atoms, preferably 2 to 4 carbon atoms, and a group of formula: (R 2 O) r R 3 in which r is 0 to 15, preferably 0 to 10, R 2 is an alkylene group having from 2 to 6 carbon atoms, preferably 2 to 4 carbon atom
  • 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 alkanolamine is one which does not contain any hydrogen-bearing nitrogen atoms. The presence of such free hydrogen atoms on the nitrogen would be expected to lead to the formation of an amide on reaction with the fatty acid.
  • 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 or 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 triisopropylamine 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 hydyroxypropyl group.
  • esters described may be made by the application or adaptation of known techniques, or are commercially available ready for use.
  • the lubricity enhancing additive compound is a derivative of the hydroxy-substituted acid and contains at least one free carboxylic group in the acid-derived moiety.
  • This kind of compound may be formed using as the starting hydroxy-substituted acid a polycarboxylic acid, for example a dicarboxylic acid or a dimer or trimer acid.
  • the number of moles of the acid and compound used to form the acid derivative which are reacted is controlled such that the resulting compound contains at least one free carboxylic functional group in the acid-derived moiety.
  • an acid having two carboxylic functions such as a dicarboxylic or dimer acid, the mole ratio should be about 1:1.
  • the ester contains at least one free carboxylic group in the acid-derived moiety and no hydroxy substitution in the acid backbone.
  • 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 acid derivative 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 do this usually depends upon the kind of acid used initially and the properties of the acid derivative it is desired to influence.
  • it is possible to increase the fuel solubility of the acid derivative by introducing into its molecule a fuel-solubilizing species.
  • long-chain alkyl or alkenyl may be mentioned.
  • the acid derivative 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.
  • the number of carbon atoms in the alkyl or alkenyl group may depend upon the number of carbon atoms in the acid derivative itself.
  • These compounds react with the free carboxylic functional group(s) of the acid derivative to form a further ester linkage or an amide linkage.
  • Examples of particular alcohols and amides which may be used include oleyl alcohols and oleyl amine.
  • Examples of compounds which may be used to introduce one or more polar head groups include polyamines (e.g. ethylene diamine and diethylene triamine), monohydric alcohols (e.g., ethanol and propanol) and alkanolamines and polyhydric alcohols such as those described above.
  • the carboxylic acid derivative is one derived from a dimer or trimer acid
  • the derivative is further reacted to introduce fuel-solubilising species.
  • Dimer and trimer acid derivatives tend already to contain in the acid backbone long chain alkyl or alkenyl moieties sufficient to provide adequate fuel-solubility.
  • the metal containing detergents are exemplified by oil-soluble overbased salts of alkali or alkaline earth metals with one or more of the following acidic substances (or mixtures thereof): (1) sulfonic acids, (2) carboxylic acids, (3) alkylphenols, (4) sulfurized alkylphenols, and (5) organic phosphorus acids characterized by at least one direct carbon-to-phosphorus linkage.
  • Such organic phosphorus acids include those prepared by the treatment of an olefin polymer (e.g., polyisobutylene) with a phosphorizing agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pentasulfide, phosphorus trichloride and sulfur, white phosphorus and a sulfur halide, or phosphorothioic chloride.
  • a phosphorizing agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pentasulfide, phosphorus trichloride and sulfur, white phosphorus and a sulfur halide, or phosphorothioic chloride.
  • phosphorizing agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pentasulfide, phosphorus trichloride and sulfur, white phosphorus and a sulfur halide, or phospho
  • the metal additives are preferably oil-soluble overbased salts of alkali or alkaline earth metals.
  • the overbased salts are preferred as a means to add metals in a concentrated, hence cost effective, form but the metals need not be added in this form.
  • the term "overbased” is used to designate metal salts wherein the metal is present in stoichiometrically larger amounts than the organic acid radical. This includes low base detergents (i.e., those having a TBN of about 6 to 40), as well as high base (i.e., those having a TBN of about 250 to 500) materials.
  • the commonly employed methods for preparing the overbased salts involve heating a mineral oil solution of an acid with a stoichiometric excess of a metal neutralizing agent such metal oxide, hydroxide, carbonate, bicarbonate, or sulfide, carbonating the mixture in the presence of a promoter, and filtering the resulting mass.
  • a metal neutralizing agent such metal oxide, hydroxide, carbonate, bicarbonate, or sulfide
  • Examples of compounds useful as the promoter include phenolic substances such as phenol, naphthol, alkylphenol, thiophenol, sulfurized alkylphenol, and condensation products of formaldehyde with a phenolic substance; alcohols such as methanol, 2-propanol, octyl alcohol, cellosolve, carbitol, ethylene glycol, stearyl alcohol, and cyclohexyl alcohol; amines such as aniline, phenylenediamine, phenothiazine, phenyl- ⁇ -naphthylamine, and dodecylamine.
  • a particularly effective method for preparing the overbased salts comprises mixing an acid with an excess of a basic alkaline earth metal neutralizing agent and at least one suitable promoter, and carbonating the mixture at an elevated temperature such as 60°-200°C.
  • overbased sulfonates include overbased lithium sulfonates, sodium sulfonates, potassium sulfonates, calcium sulfonates, and magnesium sulfonates wherein each sulfonate moiety is attached to an aromatic nucleus which in turn usually contains one or more aliphatic substituents to impart hydrocarbon solubility.
  • the metal carboxylates may be derived from any organic carboxylic acid.
  • the metal carboxylates are preferably those of a monocarboxylic acid such as that having from about 4 to 30 carbon atoms.
  • Such acids can be hydrocarbon aliphatic, alicyclic, or aromatic carboxylic acids.
  • Monocarboxylic acids such as those of aliphatic acids having about 4 to 18 carbon atoms are preferred, particularly those having an alkyl group of about 6 to 18 carbon atoms.
  • the alicyclic acids may generally contain from 4 to 12 carbon atoms.
  • the aromatic acids may generally contain one or two fused rings and contain from 7 to 14 carbon atoms wherein the carboxyl group may or may not be attached to the ring.
  • the carboxylic acid can be a saturated or unsaturated fatty acid having from about 4 to 18 carbon atoms.
  • carboxylic acids that may be used to prepare the metal carboxylates include: butyric acid; valeric acid; caproic acid; heptanoic acid; cyclohexanecarboxylic acid; cyclodecanoic acid; naphthenic acid; phenyl acetic acid; 2-methylhexanoic acid; 2-ethylhexanoic acid; suberic acid; octanoic acid; nonanoic acid; decanoic acid; undecanoic acid; lauric acid; tridecanoic acid; myristic acid; pentadecanoic acid; palmitic acid; linolenic acid; heptadecanoic acid; stearic acid; oleic acid; nonadecanoic acid; eicosanoic acid; heneicosanoic acid; docosanoi
  • carboxylic acids for preparing the oil-soluble salts of the present invention, are salicylic acids.
  • Overbased salicylate are exemplified by lithium salicylates, sodium salicylates, potassium salicylates, calcium salicylates, and magnesium salicylates wherein the aromatic moiety is usually substituted by one or more aliphatic substituents to impart hydrocarbon solubility.
  • overbased metal-containing phenate detergents include, but are not limited to, such substances as overbased lithium phenates, sodium phenates, potassium phenates, calcium phenates, magnesium phenates, sulfurized lithium phenates, sulfurized sodium phenates, sulfurized potassium phenates, sulfurized calcium phenates, and sulfurized magnesium phenates wherein each aromatic group has one or more aliphatic groups to impart hydrocarbon solubility.
  • overbased metal detergents are often referred to as "overbased phenates" or "overbased sulfurized phenates”.
  • overbased lithium, sodium, potassium, calcium, and magnesium salts of hydrolyzed phospho-sulfurized olefins having 10 to 2000 carbon atoms or of hydrolyzed phospho-sulfurized alcohols and/or aliphatic-substituted phenolic compounds having 10 to 2000 carbon atoms.
  • Other similar overbased alkali and alkaline earth metal salts of oil-soluble organic acids are suitable, such as the overbased aliphatic sulfonate salts, often referred to as "petroleum sulfonates”. Mixtures of salts of two or more different overbased alkali and/or alkaline earth metals can be used.
  • salts of mixtures of two or more different acids or two or more different types of acids can also be used. While rubidium, cesium and strontium salts are feasible, their expense renders them impractical for most uses. Likewise, while barium salts are effective, the status of barium as a heavy metal under a toxicological cloud renders barium salts less preferred for present day usage.
  • the metal containing detergent may be of the low base or high base type or mixtures thereof.
  • Low base detergents have a total base number of greater than about 8, but less than about 200.
  • Preferred metal containing detergents are high base calcium and magnesium sulfonates, sulfurized phenates and salicylates having a total base number (TBN) per ASTM D 2896-88 of at least 200, and preferably above 250.
  • the foam inhibitors useful in the present invention include those antifoam additives conventionally used in fuel compositions, such as silicone antifoam agents.
  • the advantages of the present invention are particularly evident when the antifoam used is one which exhibits a serious incompatibility with the overbased metal detergents. Incompatibility with the overbased metal detergents is evidenced by severe foaming upon combining the antifoam and the detergent. This incompatibility is most often seen where the antifoam agent is one that is largely insoluble in water at 25°C. This problem is solved by the addition of a lubricity additive of the type described above.
  • Preferred antifoam agents are polyether polysiloxane copolymers of the formula wherein R is independently selected from the group consisting of H, OH, C 1-3 alkyl, polyalkoxy, poly-(alkoxy)-X (wherein X is OH, methyl or an ester), and polyalkoxy derivatives, in which aromatic, phenolic or phenol derivatives are grafted to the alkoxy or polyether chain.
  • Polyalkoxy chains typically contain ethoxy or propoxy units, or mixtures of the two.
  • the polyether polysiloxane copolymers may be organosilicone terpolymers, such as those containing alkyl phenol or modified alkyl phenol derivatives and polyethers grafted onto a polysiloxane copolymer. Preferred are the antifoams which are substantially insoluble in water at 25°C.
  • Suitable polyether polysiloxane copolymers for use in the present invention include S911 antifoam, a polyether polydimethylsiloxane commercially available from Wacker Chemie GmbH; Dow Corning® Q2-2600 antifoam, a polyether polysiloxane copolymer commercially available from Dow Corning; and TP325 antifoam, an organosilicone terpolymer commercially available from OSi Specialties Inc.
  • Polyether polysiloxane copolymer antifoams which are not part of this invention include those which are water soluble at 25°C and do not exhibit serious incompatibility with overbased metal detergents.
  • these types of copolymers include TEGOPREN® 5851 silicone surfactant commercially available from T.H. Goldschmidt AG, Essen, Germany. Antifoams of this specific class do not cause the foam stabilization effect for which the lubricity additives of the present invention are required as a means of controlling.
  • compositions of at least one hydrocarbon-soluble dispersant comprise long chain succinimides, long chain succinic esters, long chain succinic ester-amides, long chain polyamines and long chain Mannich bases.
  • the long chain of these detergent-dispersants contains an average of at least 20 carbon atoms, e.g., an average of 30 to 200 or more carbon atoms.
  • Such long chain substituents are usually derived from polyolefin oligomers or polymers of suitable number average molecular weights such as about 800, 950, 1200, 1350, 1500, 1700, 2100 or 2300 which in turn are formed by polymerization or copolymerization of olefin monomers such as propylene, butylenes, isobutylene, amylenes, mixtures of ethylene and propylene, and the like.
  • One preferred group of dispersant-detergents for use in this invention are succinimides formed by reaction of a polyisobutenyl succinic anhydride and a polyamine, especially an ethylene polyamine having an average of 2 to 6 nitrogen atoms per molecule such as ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine, and N-[2-hydroxyethyl)ethylene diamine.
  • the polyisobutenyl group preferably has a GPC number average molecular weight in the range of 750 to 2300, more preferably 800 to 1350.
  • Mannich base dispersants formed by reaction of (i) an alkylphenol in which the alkyl group is derived from a olefin polymer that has a number average molecular weight in the range of 750 to 2300, preferably 800 to 1350 and most preferably 800 to 1100, (ii) polyalkylene polyamine and (iii) formaldehyde or a formaldehyde precursor.
  • the alkyl group of the alkylphenol is derived from polypropene having a number average molecular weight in the range of 800 to 1100
  • the polyalkylene polyamine is diethylene triamine.
  • Other useful dispersants are referred to, for example, in EP 476,196 B1.
  • Additional materials which can be included in the compositions of this invention are metal based emissions improving additives such as cyclopentadienyl manganese tricarbonyl compounds. Such compounds, when present in the finished fuels, may contribute to reduction of exhaust emissions, particularly emission of particulates and smoke.
  • use of the cyclopentadienyl manganese tricarbonyl compounds in the compositions of this invention results in further improvements in induction system cleanliness, particularly cleanliness of inlet valves.
  • Cyclopentadienyl manganese tricarbonyl compounds which can be used in the practice of this invention include cyclopentadienyl manganese tricarbonyl, methylcyclopentadienyl manganese tricarbonyl, dimethylcyclopentadienyl manganese tricarbonyl, trimethylcyclopentadienyl manganese tricarbonyl, tetramethylcyclopentadienyl manganese tricarbonyl, pentamethylcyclopentadienyl manganese tricarbonyl, ethylcyclopentadienyl manganese tricarbonyl, diethylcyclopentadienyl manganese tricarbonyl, propylcyclopentadienyl manganese tricarbonyl, isopropylcyclopentadienyl manganese tricarbonyl, tert-butylcyclopentadienyl manganese tricarbonyl, octylcyclopenta
  • cyclopentadienyl manganese tricarbonyls which are liquid at room temperature such as methylcyclopentadienyl manganese tricarbonyl, ethylcyclopentadienyl manganese tricarbonyl, liquid mixtures of cyclopentadienyl manganese tricarbonyl and methylcyclopentadienyl manganese tricarbonyl, mixtures of methylcyclopentadienyl manganese tricarbonyl and ethylcyclopentadienyl manganese tricarbonyl, etc. Preparation of such compounds is described in the literature, for example, U.S. 2,818,417.
  • manganese oleate manganese naphthenates
  • manganese octylacetoacetate manganese ethylene diamine tetracetate
  • the advantages of this invention may be achieved in any liquid fuel derived from petroleum, biomass, coal, shale and/or tar sands.
  • the base fuels will be derived primarily, if not exclusively, from petroleum.
  • the invention is thus applicable to such fuels as kerosene, jet fuel, aviation fuel, diesel fuel, home heating oil, light cycle oil, heavy cycle oil, light gas oil, heavy gas oil, bunker fuels, residual fuel oils, ultra heavy fuel oils, and in general, any liquid (or flowable) product suitable for combustion either in an engine (e.g., diesel fuel, gas turbine fuels, etc.) or in a burner apparatus.
  • suitable fuels include liquid fuels derived from biomass, such as vegetable oils (e.g., rapeseed oil, jojoba oil, cottonseed oil, etc.) or refuse-derived liquid fuels such as fuels derived from municipal and/or industrial wastes.
  • the components of the additive compositions are employed in the fuels in minor amounts sufficient to improve the combustion characteristics and properties of the base fuel in which they are employed.
  • the amounts will thus vary in accordance with such factors as base fuel type and service conditions for which the finished fuel is intended.
  • concentrations (ppm) of the components (active ingredients) in the base fuels are illustrative: General Range Preferred Range Particularly Preferred Range Component (i) Lubricity Additive 10 to 400 15 to 200 20 to 100 Component (ii) Metal Detergent 1 to 100 ppm of the metal component 5 to 50 ppm of the metal component 10 to 30 ppm of the metal component Component (iii) Antifoam Agent 1 to 30 2 to 15 3 to 8
  • the individual components (i), (ii), and (iii), and also (iv) and/or (v), if used, can be separately blended into the fuel or can be blended therein in various subcombinations, if desired.
  • the particular sequence of such blending steps is not critical.
  • such components can be blended in the form of a solution or diluent. It is preferable, however, to blend the components used in the form of an additive concentrate of this invention, as this simplifies the blending operations, reduces the likelihood of blending errors, and takes advantage of the compatibility and solubility characteristics afforded by the overall concentrate.
  • Such a concentrate forms part of the present invention and 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 fuel itself.
  • examples of other solvents or diluents include white spirit, kerosene, alcohols (e.g., 2-ethyl hexanol, isopropanol and isodecanol), aromatic solvents (e.g., toluene and xylene) and cetane improvers (e.g., 2-ethyl hexylnitrate). These may be used alone or as mixtures.
  • compositions of the present invention may further contain optional components conventionally used in fuel compositions such as fuel stabilizers, cetane number improvers, anti-icers, combustion modifiers, cold flow improvers, antistatic additives, biocides, antioxidants, corrosion inhibitors, wax antisettling additives and metal deactivators.
  • fuel stabilizers such as fuel stabilizers, cetane number improvers, anti-icers, combustion modifiers, cold flow improvers, antistatic additives, biocides, antioxidants, corrosion inhibitors, wax antisettling additives and metal deactivators.
  • the various optional components that can be included in the fuel compositions of this invention are used in conventional amounts. Thus, the amounts of such optional components are not critical to the practice of the present invention. The amounts used in any particular case are sufficient to provide the desired functional property to the fuel composition, and such amounts are well known to those skilled in the art.
  • the base fuel used in the present examples is a low sulfur ( ⁇ 0.05% by weight of sulfur) diesel fuel.
  • the cylinders were filled to the 100 mL mark with fuel. They were then stoppered and shaken for 1 minute at 2-3 strokes per second, each stroke being 15 to 30 cm long and in a vertical plane. The shaken cylinders were then placed on a level surface, free from vibration, and the maximum foam volume (ml of foam), and the time for the first clear point of fuel to form (time (sec) to first spot) were recorded.
  • Example 2 The results in Table 2 indicate that the fuel additive compositions of the present invention (Examples 1 and 2) provide fuel compositions which exhibit significantly reduced foam volume and time to first spot compared to compositions containing only base fuel (Comparative Example 5), or fuel compositions containing additive mixtures outside the scope of the present invention (Comparative Examples 1-4) as is evidenced by the significantly lower values for the foam volume and time to first spot tests obtained in Examples 1 and 2.
  • Table 3 demonstrates the beneficial effects on foam properties obtained by the addition of a fatty acid lubricity additive to a system containing an antifoam and an overbased detergent.
  • Example 3 The results in Table 3 indicate that the fuel additive compositions of the present invention (Example 3) provide fuel compositions which exhibit significantly reduced foam volume and time to first spot compared to compositions containing additive mixtures outside Components
  • Example 3 Comparative Example 6 Solvent 1 24.4g 20.83g Metal Detergent 4 17.86g 20.3g Antifoam 8 1.63g 1.87g Lubricity Additive 6.09g --- Treat rate: volume added to fuel 0.41 ml of formulation per 1000 ml of fuel 0.36 ml of formulation per 1000 ml of fuel Foam Decay Time to first spot(s) 25.7 sec >11 minutes Foam volume/ml 8.7 ml 30 ml the scope of the present invention (Comparative Example 6) as is evidenced by the significantly lower values for the foam volume and time to first spot tests obtained in Example 3.

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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)
  • Combustion & Propulsion (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Lubricants (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)

Claims (14)

  1. Composition d'additif pour carburant qui comprend (i) un additif lubrifiant, (ii) un détergent métallique suralcalinisé ou surbasique, et (iii) un agent antimoussant à base de siloxane qui est insoluble dans l'eau à 25°C, et dans laquelle les composants (i), (ii) et (iii) sont présents en quantités telles, qu'une fois la composition diluée avec un hydrocarbure
    ou une huile de base, chaque composant est présent selon la concentration suivante : composant (i) 10 - 400 ppm composant (ii) 1 - 100 ppm de composant métallique composant (iii) 1 - 30 ppm
  2. Composition d'additif pour carburant selon la revendication 1, dans laquelle l'additif lubrifiant est un acide carboxylique, un amide d'acide carboxylique ou un ester d'acide carboxylique.
  3. Composition d'additif pour carburant selon la revendication 1 ou la revendication 2, dans laquelle l'additif lubrifiant est choisi dans le groupe consistant en l'oléyl éthanolamide et l'oléyl diéthanolamide.
  4. Composition d'additif pour carburant selon l'une quelconque des revendications précédentes, dans laquelle le détergent métallique suralcalinisé ou surbasique est choisi dans le groupe consistant en des sulfonates de calcium, des sulfonates de magnésium, des phénates sulfurisés de calcium, des phénates sulfurisés de magnésium, des salicylates de calcium, et des salicylates de magnésium, où le détergent possède un indice d'alcalinité total (TBN) selon la norme ASTM D 2896-88 au moins égal à 200.
  5. Composition d'additif pour carburant selon l'une quelconque des revendications précédentes, dans laquelle l'agent antimoussant est un agent antimoussant à base de silicone.
  6. Composition d'additif pour carburant selon la revendication 5, dans laquelle l'agent antimoussant à base de silicone est un copolymère de polyéther-polysiloxane.
  7. Composition d'additif pour carburant selon l'une quelconque des revendications précédentes, qui comprend en outre au moins un ingrédient choisi dans le groupe consistant en des agents dispersants, des additifs de réduction des émissions à base de métaux, des agents desemulsionnants et des agents anticorrosion.
  8. Composition d'additif pour carburant selon la revendication 7, dans laquelle l'agent dispersant est un agent dispersant soluble dans les hydrocarbures choisi dans le groupe consistant en les dérivés succinimidiques à longue chaíne, les esters succiniques à longue chaíne, les ester succiniques-amides à longue chaíne, les polyamines à longue chaíne, et les bases de Mannich à longue chaíne.
  9. Composition d'additif pour carburant selon la revendication 7, dans laquelle l'additif de réduction des émissions à base de métaux est un dérivé de tricarbonyl cyclopentadiényl manganèse.
  10. Concentré d'additif comprenant de 99% à 1% en poids d'additif selon l'une quelconque des revendications précédentes et de 1 à 99% en poids de solvant ou diluant pour additif, lequel solvant ou diluant est miscible et/ou soluble dans le carburant devant être traité par le concentré.
  11. Composition de carburant comprenant (a) une fraction majeure de carburant de base et (b) une fraction mineure de l'additif pour carburant selon l'une quelconque des revendications 1 à 9, dans laquelle l'additif pour carburant est présent en quantité suffisante pour améliorer le profil moussant du carburant.
  12. Procédé de réduction du taux de mousse dans une composition de carburant contenant un détergent métallique suralcalinisé ou surbasique et un agent antimoussant à base de siloxane qui est insoluble dans l'eau à 25°C, dans lequel un additif lubrifiant est combiné à ladite composition de carburant.
  13. Procédé selon la revendication 12, dans lequel l'additif lubrifiant est un acide carboxylique, un amide d'acide carboxylique ou un ester d'acide carboxylique.
  14. Procédé selon la revendication 12, dans lequel l'agent antimoussant à base de siloxane est un copolymère de polyéther-polysiloxane.
EP19980301109 1997-02-17 1998-02-16 L'utilisation d'additifs lubrifiants pour diminuer le mousse dans les fuels Expired - Lifetime EP0859040B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9703266A GB2322138A (en) 1997-02-17 1997-02-17 Foam reducing fuel additive
GB9703266 1997-02-17

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EP0859040A1 EP0859040A1 (fr) 1998-08-19
EP0859040B1 true EP0859040B1 (fr) 2002-05-08

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EP (1) EP0859040B1 (fr)
CN (1) CN1090230C (fr)
CA (1) CA2228989A1 (fr)
DE (1) DE69805225T2 (fr)
GB (1) GB2322138A (fr)
ID (1) ID19923A (fr)
SG (1) SG79226A1 (fr)

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US6200359B1 (en) * 1998-12-23 2001-03-13 Shell Oil Company Fuel oil composition
AU2001248679A1 (en) 2000-03-31 2001-10-08 Texaco Development Corporation Fuel additive composition for improving delivery of friction modifier
DE10251312A1 (de) * 2002-11-04 2004-05-19 Basf Ag Kraftstoffe mit verbesserter Additivwirkung
US20050005506A1 (en) * 2003-07-08 2005-01-13 Henly Timothy J. Distillate fuel compositions for improved combustion and engine cleanliness
US7696136B2 (en) 2004-03-11 2010-04-13 Crompton Corporation Lubricant compositions containing hydroxy carboxylic acid and hydroxy polycarboxylic acid esters
AR069052A1 (es) 2007-10-30 2009-12-23 Shell Int Research Mezclas para utilizar en composiciones de combustible
US20120222348A1 (en) * 2011-03-01 2012-09-06 Basf Se Medium-chain alkanols in additive concentrates for improving foam reduction in fuel oils
WO2012117004A2 (fr) * 2011-03-01 2012-09-07 Basf Se Alcanols à chaîne moyenne dans des concentrés d'additif servant à améliorer la réduction de mousse dans les huiles combustibles

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ES2060058T3 (es) * 1990-09-20 1994-11-16 Ethyl Petroleum Additives Ltd Composiciones de combustible hidrocarbonado y aditivos para las mismas.
GB9315205D0 (en) * 1993-07-22 1993-09-08 Exxon Chemical Patents Inc Additives and fuel compositions
DE69418152T2 (de) * 1993-11-19 1999-10-14 Dow Corning Corp. Mitteldestillatskohlenwasserstoffsschaumkontrollemittel, von Alkylmethylsiloxanen
DE4343235C1 (de) * 1993-12-17 1994-12-22 Goldschmidt Ag Th Verwendung von organofunktionell modifizierten Polysiloxanen zum Entschäumen von Dieselkraftstoff
GB9410820D0 (en) * 1994-05-31 1994-07-20 Exxon Chemical Patents Inc Oil additives and compositions
GB2289287A (en) * 1994-05-04 1995-11-15 Ethyl Petroleum Additives Ltd Fuel foam control additive
EP0698656B1 (fr) * 1994-08-24 2000-10-18 Shell Internationale Researchmaatschappij B.V. Produits de réaction de polyènes solubles dans l'huile

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ID19923A (id) 1998-08-20
SG79226A1 (en) 2001-03-20
CN1199771A (zh) 1998-11-25
CA2228989A1 (fr) 1998-08-17
DE69805225D1 (de) 2002-06-13
EP0859040A1 (fr) 1998-08-19
CN1090230C (zh) 2002-09-04
GB9703266D0 (en) 1997-04-09
DE69805225T2 (de) 2002-12-05
GB2322138A (en) 1998-08-19

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