EP0476196A1 - Kohlenwasserstoffzusammensetzungen und Zusätze dafür - Google Patents
Kohlenwasserstoffzusammensetzungen und Zusätze dafür Download PDFInfo
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- EP0476196A1 EP0476196A1 EP90310322A EP90310322A EP0476196A1 EP 0476196 A1 EP0476196 A1 EP 0476196A1 EP 90310322 A EP90310322 A EP 90310322A EP 90310322 A EP90310322 A EP 90310322A EP 0476196 A1 EP0476196 A1 EP 0476196A1
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- fuel
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Definitions
- This invention relates to liquid fuel compositions of enhanced performance properties, particularly as regards combustion characteristics.
- Keszthelyi et al report in Period. Polytech., Chem. Eng., Volume 21 (1 pages 79-93 (1977) that in the combustion of light fuel oils in evaporating burners, 0.025% cyclopentadienyl manganese tricarbonyl was effective for soot reduction. And in Margantsevye Antidetonatory, edited by A. N. Nesmeyanov, Nauka, Moscow, 1971, at pages 192-199, Makhov et al report test work indicating that addition of cyclopentadienyl manganese tricarbonyl to diesel fuel reduces the level of smokiness of the exhaust gases.
- Canadian Patent No. 1,188,891 describes an additive for fuel oils and diesel fuels and other liquid combustibles and motor fuels designed to improve combustion, reduce soot formation and enhance storage stability.
- Such additive is composed of at least one oil-soluble or oil-dispersible organic compound of a transition metal or an alkaline earth metal; and at least one oxidation and polymerisation inhibitor for hydrocarbons stable at temperatures of at least 300 ° C.
- the presence in such fuels of compounds of transition metals such as copper, manganese, cobalt, nickel and iron accelerate fuel deterioration in accelerated stability tests conducted at 149°C in the presence of air.
- Such compounds as MMT, Ferrocene, copper naphthenate, iron naphthenate, and manganese naphthenate are indicated to cause such deterioration in the absence of a high temperature (e.g., 300 °C) stabiliser such as heat-stable alkyl phenols, amines, aminophenols, dithiophosphates, dithiocarbamates and imidazoles and inorganic inhibitors in the form of oxides or hydroxides of aluminum, magnesium or silicon.
- a high temperature (e.g. 300 °C) stabiliser such as heat-stable alkyl phenols, amines, aminophenols, dithiophosphates, dithiocarbamates and imidazoles and inorganic inhibitors in the form of oxides or hydroxides of aluminum, magnesium or silicon.
- a high temperature (e.g. 300 °C) stabiliser such as heat-stable alkyl phenols, amines, aminophenols, dithiophosphates, dithi
- G.B. Patent No. 1,413,323 describes a multi-component diesel fuel additive to avoid or reduce the formation of deposits on injector parts.
- the additive comprises, inter alia, an ester of oleic or naphthenic acid having an acid number below 200; a naphthenic acid ester of cresol; an alkoxyalkyl ester of an aliphatic carboxylic acid; an organometallic tricarbonyl cyclopentadiene compound such as cyclopentadienyl manganese tricarbonyl; an amide derivative of a polyolefin obtained by the reaction of a polyolefin substituted succinic acid or anhydride with a polyamine; a copolymer of ethylene and a vinyl (or hydrocarbyl-substituted vinyl) ester of a carboxylic acid wherein the copolymer has a number average molecular weight of more than 3000; a re-odoriser composed of a mixture of natural and synthetic alcohols, ketones
- compositions comprising the combination of a transition metal salt such as a manganese carboxylate, and an ashless hydrocarbon-soluble ashless dispersant.
- a transition metal salt such as a manganese carboxylate
- an ashless hydrocarbon-soluble ashless dispersant An optimum balance between beneficial and deleterious effects is said to be achieved in oils of lubricating viscosity and hydrocarbon fuels.
- additive composition which is capable of reducing or inhibiting the amount of noxious emissions (e.g., carbon monoxide, unburned hydrocarbons, polyaromatic hydrocarbons, and/or particulates) formed when using the fuels in an engine or in a burner or like combustion apparatus.
- noxious emissions e.g., carbon monoxide, unburned hydrocarbons, polyaromatic hydrocarbons, and/or particulates
- the provision of additive compositions capable of decreasing fuel consumption is also a most desirable objective.
- this invention provides an additive composition for hydrocarbonaceous fuels.
- Such additive composition comprises:
- this invention provides a fuel composition which comprises a major amount of a liquid hydrocarbonaceous fuel containing a minor combustion-improving amount of components a), b) and c) as just described.
- the additive compositions and fuel compositions are essentially halogen-free, that is, they contain no more than 10 ppm of halogen, if any.
- Preferred manganese carbonyl compounds -- component a) above -- are cyclopentadienyl manganese tricarbonyl compounds.
- the preferred component b) salts are the sodium, potassium, calcium and magnesium salts of sulphonic acids, of alkylphenols,of sulphurised alkylphenols, and of carboxylic acids, especially aromatic carboxylic acids.
- Preferred ashless dispersants for use as component c) are basic nitrogen-containing ashless dispersants, especially polyolefin-substituted succinimides of polyethylene polyamines such as polyethylene tetramines, polyethylene pentamines and polyethylene hexamines.
- compositions for use in heating gas oils and similar burner fuels contain, in addition to components a), b) and c) above, one or more of the following:
- compositions for use in road diesel fuels and similar middle distillate fuels contain, in addition to components a), b) and c) above, component d), namely, at least one fuel-soluble demulsifying agent.
- fuel-soluble means that the compound or component under discussion has sufficient solubility at ordinary ambient temperature in the hydrocarbonaceous fuel in which it is to be used to provide a homogeneous solution containing the compound or component in at least the lowest concentration of the concentration ranges specified herein for such compound or component.
- the manganese compounds -- component a) -- of the compositions of this invention are characterised by being fuel soluble and by having at least one carbonyl group bonded to a manganese atom.
- the most desirable general type of manganese carbonyl compounds utilised in accordance with this invention comprise organomanganese polycarbonyl compounds.
- organomanganese polycarbonyl compounds For best results, use should be made of a cyclopentadienyl manganese tricarbonyl compound of the type described in U. S. Pat. Nos. 2,818,417 and 3,127,351.
- cyclopentadienyl manganese tricarbonyl methylcyclopentadienyl manganese tricarbonyl, ethylcyclopentadienyl manganese tricarbonyl, dimethyl- cyclopentadienyl manganese tricarbonyl, trimethylcyclopentadienyl manganese tricarbonyl, propylcyclopen- tadienyl manganese tricarbonyl, isopropylcyclopentadienyl manganese tricarbonyl, butylcyclopentadienyl manganese tricarbonyl, pentylcyclopentadienyl manganese tricarbonyl, hexylcyclopentadienyl manganese tricarbonyl, ethylmethylcyclopentadienyl manganese tricarbonyl, dimethyloctylcyclopentadienyl manganese tricarbonyl, dodecyl
- a preferred organomanganese compound is cyclopentadienyl manganese tricarbonyl. Particularly preferred for use in the practise of this invention is methylcyclopentadienyl manganese tricarbonyl.
- organomanganese compounds which may be employed include the non-ionic diamine manganese tricarbonyl halide compounds such as bromo manganese dianiline tricarbonyl and bromo manganese dipyridine tricarbonyl, described in U. S. Pat. No. 2,902,489; the acyl manganese tricarbonyls such as methylacetyl cyclopentadienyl manganese tricarbonyl and benzoyl methyl cyclopentadienyl manganese tricarbonyl, described in U. S. Pat. No.
- cyclopentadienyl manganese dicarbonyl compounds of the formula RMn(CO) 2 L where R is a substituted or unsubstituted cyclopentadienyl group having 5 to 18 carbon atoms, and L is a ligand, such as an olefin, an amine, a phosphine, S0 2 , tetrahydrofuran, or the like.
- R is a substituted or unsubstituted cyclopentadienyl group having 5 to 18 carbon atoms
- L is a ligand, such as an olefin, an amine, a phosphine, S0 2 , tetrahydrofuran, or the like.
- Such compounds are referred to, for example in, Herberhold, M., Metal 1T -Complexes, Vol. II, Amsterdam, Elsevier, 1967 or Giordano, P. J. and Weighton, M.S., Inorg
- Metal-containing detergents are exemplified by oil-soluble neutral and basic salts of alkali or alkaline earth metals with one or more of the following acidic substances (or mixtures thereof): (1) sulphonic acids, (2) carboxylic acids, (3) salicylic acids, (4) alkylphenols, (5) sulphurised alkylphenols, (6) organic phosphorus acids characterised 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., polyisobutene having a molecular weight of 1000) with a phosphorising agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pentasulphide, phosphorus trichloride and sulphur, white phosphorus and a sulphur halide, or phosphorothioic chloride.
- a phosphorising agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pentasulphide, phosphorus trichloride and sulphur, white phosphorus and a sulphur halide, or phosphorothioic chloride.
- phosphorising agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pentasulphide, phosphorus trichloride
- basic salt is used to designate metal salts wherein the metal is present in stoichiometrically larger amounts than the organic acid radical.
- the commonly employed methods for preparing the basic salts involve heating a mineral oil solution of an acid with a stoichiometric excess of a metal neutralising agent such as the metal oxide, hydroxide, carbonate, bicarbonate, or sulphide at a temperature of about 50 °C, and filtering the resulting mass.
- a “promoter” in the neutralisation step to aid the incorporation of a large excess of metal likewise is known.
- Examples of compounds useful as the promoter include phenolic substances such as phenol, naphthol, alkylphenol, thiophenol, sulphurised 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; and amines such as aniline, phenylenediamine, phenothiazine, phenyl-beta-naphthylamine, and dodecylamine.
- a particularly effective method for preparing the basic salts comprises mixing an acid with an excess of a basic alkaline earth metal neutralising agent and at least one alcohol promoter, and carbonating the mixture at an elevated temperature such as 60 ° -200 ° C.
- suitable metal-containing detergents include, but are not limited to, such substances as lithium phenates, sodium phenates, potassium phenates, calcium phenates, magnesium phenates, sulphurised lithium phenates, sulphurised sodium phenates, sulphurised potassium phenates, sulphurised calcium phenates, and sulphurised magnesium phenates wherein each aromatic group has one or more aliphatic groups to impart hydrocarbon solubility; the basic salts of any of the foregoing phenols or sulphurised phenols (often referred to as "overbased" phenates or "overbased sulphurised phenates”); lithium sulphonates, sodium sulphonates, potassium sulphonates, calcium sulphonates, and magnesium sulphonates wherein each sulphonic acid moiety is attached to an aromatic nucleus which in turn usually contains one or more aliphatic substituents to impart hydrocarbon solubility; the basic salts of any of the foregoing
- salts of two or more different 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 e.g., one or more calcium phenates with one or more calcium sulphonates
- rubidium, cesium and strontium salts are feasible, their expense renders them impractical for most uses.
- 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.
- Ashless dispersants are described in numerous patent specifications, mainly as additives for use in lubricant compositions, but their use in hydrocarbon fuels has also been described. Ashless dispersants leave little or no metal-containing residue on combustion. They generally contain only carbon, hydrogen, oxygen and in most cases nitrogen, but sometimes contain in addition other non-metallic elements such as phosphorus, sulphur or boron.
- the preferred ashless dispersant is an alkenyl succinimide of an amine having at least one primary amino group capable of forming an imide group.
- alkenyl succinimides may be formed by conventional methods such as by heating an alkenyl succinic anhydride, acid, acid-ester, acid halide, or lower alkyl ester with an amine containing at least one primary amino group.
- the alkenyl succinic anhydride may be made readily by heating a mixture of olefin and maleic anhydride to about 180 *- 220 * C.
- the olefin is preferably a polymer or copolymer of a lower monoolefin such as ethylene, propylene, isobutene and the like.
- the more preferred source of alkenyl group is from polyisobutene having a molecular weight up to 10,000 or higher.
- the alkenyl group is a polyisobutene group having a molecular weight of about 500-5,000, and preferably about 900-2,000, especially 900-1,200.
- Amines which may be employed in forming the ashless dispersant include any that have at least one primary amino group which can react to form an imide group.
- a few representative examples are: methylamine, 2-ethylhexylamine, n-dodecylamine, stearylamine, N,N-dimethylpropanediamine, N-(3-aminopropyl)morpholine, N-dodecylpropanediamine, N-aminopropyl-piperazine, ethanolamine, N-ethanol- ethylenediamine and the like.
- the preferred amines are the alkylene polyamines such as propylene diamine, dipropylene triamine, di-(1,2-butylene)triamine, and tetra-(1,2-propylene)pentamine.
- the most preferred amines are the ethylene polyamines which can be depicted by the formula wherein n is an integer from one to about ten. These include: ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine, and the like, including mixtures thereof in which case n is the average value of the mixture. These ethylene polyamines have a primary amine group at each end so can form mono-alkenylsuccinimides and bis-alkenylsuccinimides.
- ethylene polyamine mixtures usually contain minor amounts of branched species and cyclic species such as N-aminoethyl piperazine, N,N'-bis(aminoethyl)piperazine, N,N'-bis(piperazinyl)ethane, and like compounds.
- the preferred commercial mixtures have approximate overall compositions falling in the range corresponding to diethylene triamine to tetraethylene pentamine, mixtures generally corresponding in overall makeup to tetraethylene pentamine being most preferred.
- especially preferred ashless dispersants for use in the present invention are the products of reaction of a polyethylene polyamine, e.g. triethylene tetramine or tetraethylene pentamine with a hydrocarbon substituted carboxylic acid or anhydride made by reaction of a polyolefin, preferably polyisobutene, having a number average molecular weight of 500 to 5,000, preferably 900 to 2,000 and especially 900 to 1,200, with an unsaturated polycarboxylic acid or anhydride, e.g., maleic anhydride, maleic acid, fumaric acid, or the like, including mixtures of two or more such substances.
- a polyethylene polyamine e.g. triethylene tetramine or tetraethylene pentamine
- a hydrocarbon substituted carboxylic acid or anhydride made by reaction of a polyolefin, preferably polyisobutene, having a number average molecular weight of 500 to 5,000, preferably 900 to 2,000 and
- alkenyl succinic acid esters and diesters of alcohols containing 1-20 carbon atoms and 1-6 hydroxyl groups Representative examples are described in U.S. Pat. Nos. 3,331,776; 3,381,022; and 3,522,179.
- the alkenyl succinic portion of these esters corresponds to the alkenyl succinic portion of the succinimides described above including the same preferred and most preferred subgenus, e.g., polyisobutenyl succinic acids wherein the polyisobutenyl group has a number average molecular weight of 500 to 5,000, preferably 900-2,000, especially 900 to 1,200.
- Alcohols useful in preparing the esters include methanol, ethanol, isobutanol, octadecanol, eicosanol, ethylene glycol, diethylene glycol, tetraethylene glycol, diethylene glycol monoethylether, propylene glycol, tripropylene glycol, glycerol, sorbitol, 1,1,1-trimethylol ethane, 1,1,1-trimethylol propane, 1,1,1-trimethylol butane, pentaerythritol, dipentaerythritol, and the like.
- the succinic esters are readily made by merely heating a mixture of alkenyl succinic acid, anhydrides or lower alkyl (e.g., C 1 -C 4 ) ester with the alcohol while distilling out water or lower alkanol. In the case of acid-esters less alcohol is used. In fact, acid-esters made from alkenyl succinic anhydrides do not evolve water. In another method the alkenyl succinic acid or anhydrides can be merely reacted with an appropriate alkylene oxide such as ethylene oxide, propylene oxide, and the like, including mixtures thereof.
- an appropriate alkylene oxide such as ethylene oxide, propylene oxide, and the like, including mixtures thereof.
- the ashless dispersant is an alkenyl succinic ester-amide mixture.
- alkenyl succinic ester-amide mixture may be made by heating the above-described alkenyl succinic acids, anhydrides or lower alkyl esters with an alcohol and an amine either sequentially or in a mixture.
- the alcohols and amines described above are also useful in this embodiment.
- amino alcohols can be used alone or with the alcohol and/or amine to form the ester-amide mixtures.
- the amino alcohol can contain 1-20 carbon atoms, 1-6 hydroxy groups and 1-4 amine nitrogen atoms. Examples are ethanolamine, diethanolamine, N-ethanol-diethylene triamine, and trimethylol aminomethane.
- ester-amide mixtures are described in U.S. Pat. Nos. 3,184,474; 3,576,743; 3,632,511; 3,804,763; 3,836,471; 3,862,981; 3,936,480; 3,948,800; 3,950,341; 3,957,854; 3,957,855; 3,991,098; 4,071,548; and 4,173,540.
- Such ashless dispersants containing alkenyl succinic residues may, and as is well known, be post- reacted with boron compounds, phosphorus derivatives and/or carboxylic acid acylating agents, e.g. maleic anhydride.
- Another useful class of ashless dispersants includes the Mannich condensates of hydrocarbyl-substituted phenols, formaldehyde or formaldehyde precursors (e.g. paraformaldehyde) and an amine having at least one primary amine group and containing 1-10 amine groups and 1-20 carbon atoms.
- Mannich condensates useful in this invention are described in U.S. Pat. Nos.
- Mannich condensates are those made by condensing a polyisobutenyl phenol wherein the polyisobutyl group has an average molecular weight of about 800-3,000 with formaldehyde or a formaldehyde precursor and an ethylene polyamine having the formula:
- a further type of ashless dispersants which can be used comprises interpolymers of oil-solubilising monomers such as decyl methacrylate, vinyl decyl ether and high molecular weight olefins with monomers containing polar substituents, e.g., aminoalkyl acrylates or acrylamides and poly(oxyethylene)-substituted acrylates.
- polar substituents e.g., aminoalkyl acrylates or acrylamides and poly(oxyethylene)-substituted acrylates.
- Another class of ashless dispersants which can advantageously be used in the fuel compositions of this invention are the imidazoline dispersants which can be represented by the formula: wherein R 1 represents a hydrocarbon group having 1 to 30 carbon atoms, e.g. an alkyl or alkenyl group having 7 to 22 carbon atoms, and R 2 represents a hydrogen atoms or a hydrocarbon radical of 1 to 22 carbon atoms, or an aminoalkyl, acylaminoalkyl or hydroxyalkyl radical having 2 to 50 carbon atoms.
- R 1 represents a hydrocarbon group having 1 to 30 carbon atoms, e.g. an alkyl or alkenyl group having 7 to 22 carbon atoms
- R 2 represents a hydrogen atoms or a hydrocarbon radical of 1 to 22 carbon atoms, or an aminoalkyl, acylaminoalkyl or hydroxyalkyl radical having 2 to 50 carbon atoms.
- Such long-chain alkyl (or long-chain alkenyl) imidazoline compounds may be made by reaction of a corresponding long-chain fatty acid (of formula Ri-COOH), for example oleic acid, with an appropriate polyamine.
- the imidazoline formed is then ordinarily called, for example, oleylimidazoline where the radical R 1 represents the oleyl residue of oleic acid.
- Other suitable alkyl substituents in the 2- position of these imidazolines include undecyl, heptadecyl, lauryl and erucyl.
- Suitable N-substituents of the imidazolines i.e.
- radicals R 2 include hydrocarbyl groups, hydroxyalkyl groups, aminoalkyl groups, and acylaminoalkyl groups. Examples of the foregoing groups include methyl, butyl, decyl, cyclohexyl, phenyl, benzyl, tolyl, hydroxyethyl, aminoethyl, oleylaminoethyl and stearylaminoethyl.
- polyamines examples include N-oleyl-1,3-propanediamine, N-stearyl-1,3-propanediamine, N-oleyl-1,3-butanediamine, N-oleyl-2-methyl-1,3-propanediamine, N-oleyl-1,3-pentanediamine, N-oleyl-2-ethyl-1,3-propanediamine, N-stearyl-1,3-butanediamine, N-stearyl-2-methyl-1,3-propanediamine, N-stearyl-1,3-pentanediamine, N-stearyl-2-ethyl-1,3-propanediamine, N-oleyl-dipropylenetriamine and N-stearyl- dipropylenetriamine.
- Such linear N-alkylpolyamines are condensed with, e.g., a succinic, maleic, phthalic or hexahydrophthalic acid anhydride which may be substituted by one or more radicals of up to 5 carbon atoms each.
- Another class of ashless dispersant which can be incorporated in the compositions of the present invention are the products of reaction of an ethoxylated amine made by reaction of ammonia with ethylene oxide with a carboxylic acid of 8 to 30 carbon atoms.
- the ethoxylated amine may be, for example, mono-, di- or tri-ethanolamine or a polyethoxylated derivative thereof, and the carboxylic acid may be, for example, a straight or branched chain fatty acid of 10 to 22 carbon atoms, a naphthenic acid, a resinic acid or an alkyl aryl carboxylic acid.
- Still another type or ashless dispersants which can be used in the practise of this invention are the a-olefin-maleimide copolymers such as are described in U.S. Pat. No. 3,909,215.
- Such copolymers are alternating copolymers of N-substituted maleimides and aliphatic a-olefins of from 8 to 30 carbon atoms.
- the copolymers may have an average of 4 to 20 maleimide groups per molecule.
- the substituents on the nitrogen of the maleimide may be the same or different and are organic radicals composed essentially of carbon, hydrogen and nitrogen having a total of 3 to 60 carbon atoms.
- a commercially available material which is highly suitable for use in this invention is Chevron OFA 425B, and this material is believed to be or comprise an a-olefin maleimide copolymer of the type described in U.S. Pat. No. 3,909,215. Whatever its composition, it works quite well.
- ashless dispersants which contain little, if any, halogen atoms such as chlorine atoms.
- the additive composition contains no detectable amount of halogen.
- Typical halogen (chlorine)-free ashless dispersants suitable for use in the compositions of this invention include, in addition to various types described hereinabove, those described in the following recently- published applications: WO 9003359 and EP 365288.
- Demulsifying agents A variety of materials are available for use in those preferred embodiments of this invention in which at least one demulsifying agent is employed as component d) along with components a), b) and c).
- the demulsifying agent improves the water tolerance level of the fuel compositions by minimizing or preventing excessive emulsion formation.
- Exemplary demulsifiers which may be employed in the practise of this invention include poly-(alkylphenol) formaldehyde condensates and the polyalkylenoxy modified reaction products thereof. These compounds are prepared by reacting an alkylphenol with formaldehyde and thereafter reacting the reaction product of the above with a C 2 to C 6 alkylene oxide such as ethylene oxide and propylene oxide.
- the demulsifiers have a generalized structural formula wherein U is an alkylene of 2 to 6 carbons; y is an integer averaging between 4 and 10; x is an integer averaging between 4 and 10; and R 5 is an alkyl having from 4 to 15 carbon atoms.
- Preferred demulsifiers described by the above formula are polyethyleneoxy modified methylene bridged poly(alkylphenol) polymers having a polyethyleneoxy chain of 8 to 20 carbons and preferably from 10 to 16 carbons and at least about 75 number percent of the polyethyleneoxy chains being within the range specified.
- the methylene bridged poly(alkylphenol) portion of the polymer has from 4 to 10 and preferably from 5 to 8 repeating methylene bridged alkylphenol units with 4 to 15 and preferably 6 to 12 carbons in the alkyl group.
- the alkyl groups are a mixture of alkyls having between 4 and 12 carbon atoms.
- Illustrative alkylphenols include p-isobutylphenol, p-diisobutylphenol, p-hexylphenol, p-heptylphenol, p-octylphenol, p-tripropylenephenol, and p-dipropylenephenol, etc.
- demulsifier component is an ammonia-neutralised sulphonated alkylphenol.
- R 1 is a hydrocarbyl group having from 4 to 15 carbon atoms, preferably from 6 to 12.
- These compounds are prepared by sulphonating an alkylated phenol and thereafter neutralising the sulphonated product with ammonia.
- demulsifier is an oxyalkylated glycol.
- These compounds are prepared by reacting a polyhydroxy alcohol such as ethylene glycol, trimethylene glycol, etc., with ethylene or propylene oxide.
- ethylene glycol trimethylene glycol, etc.
- propylene oxide ethylene or propylene oxide.
- Many of the compounds are commercially available from BASF-Wyandotte Chemical Company under the PLURONIC trademark. They are polyethers terminated by hydroxy groups and produced by the block copolymerisation of ethylene oxide and propylene oxide.
- the ethylene oxide blocks act as the hydrophiles and the propylene oxide blocks as the hydrophobes. They are available in a wide range of molecular weights and with varying ratios of ethylene oxide to propylene oxide.
- demulsifiers comprises a mixture of alkylaryl sulphonates, polyoxyalkylene glycols and oxyalkylated alkylphenolic resins.
- Such products are supplied by Petrolite Corporation under the TOLAD trademark.
- One such propriety product, identified as TOLAD 286K, is understood to be a mixture of these components dissolved in a solvent composed of alkyl benzenes. This product has been found efficacious for use in the compositions of this invention.
- a related product, TOLAD 286, is also suitable. In this case the product apparently contains the same kind of active ingredients dissolved in a solvent composed of heavy aromatic naphtha and isopropanol.
- other known demulsifiers can be used.
- Aliphatic or cycloaliphatic amine In the embodiments of this invention wherein component e) is used, a wide variety of suitable amines are available. This component contributes stability to the systems in which it is employed. Typically, component e) is a monoamine although polyamines can be used, if desired. Among the vast array of suitable amines are included the amines referred to in U.S. Pat. No. 3,909,215 such as tertiary alkyl primary amines including Primene 81 R and the like, and amines referred to in EP 188,042, namely alkyldimethylamines in which the alkyl group has 8 to 14 carbon atoms or mixtures thereof.
- mixed alkyl-cycloalkyl amines such as N-cyclohexyl-N-butyl amine, N-methylcyclohexyl-N-octyl amine, etc., as well as di- and tricycloalkyl amines such as N,N-dicyclohexyl amine, N,N-di-(ethylcyclohexyl)-amine, N,N,N-tricyclohexyl amine, and the like.
- Preferred amines include N-cycloalkyl-N,N-dialkyl amines and N-cycloalkenyl-N,N-dialkylamines such as N-cyclohexyl-N,N-diethyl amine, N-cyclohexyl-N,N-dibutyl amine, N-cycloheptyl-N,N-dimethyl amine, N-cyclooctyl-N,N-dilauryl amine, N-cyclohexenyl-N,N-dipropyl amine, and like compounds. Particularly preferred is N-cyclohexyl-N,N-dimethyl amine. Mixtures of various amines, such as those referred to above, are also suitable for use in accordance with this invention.
- Metal deactivators Generally speaking, metal deactivators fall into two broad categories. One category comprises the passivators which are considered to react with the metal surface and thereby passivate the surface. The other category comprises the chelators, i.e., substances which have the capability of reacting or complexing with dissolved metal and/or metal ions.
- An example of the passivator type is the thiadiazoles such as HITEC 314 additive (Ethyl Petroleum Additives, Ltd.; Ethyl Petroleum Additives, Inc.).
- Examples of the chelator type of metal deactivators include 8-hydroxyquinoline, ethylene diamine tetracarboxylic acid, ;8-diketones such as acetylacetone, (3-ketoesters such as octyl acetoacetate, and the like.
- the preferred metal deactivators which are generally regarded as chelators, are Schiff bases, such as N,N'-disalicylidene-1,2-ethanediamine, N,N'-disalicylidene-1,2-propanediamine, N,N'-disalicylidene-1,2-cyclohexanediamine, and N,N"-disalicylidene-N'-methyl-dipropylenetriamine.
- Schiff bases such as N,N'-disalicylidene-1,2-ethanediamine, N,N'-disalicylidene-1,2-propanediamine, N,N'-disalicylidene-1,2-cyclohexan
- a particular advantage associated with the use of the metal deactivators, especially of the Schiff base chelator type, is their ability to overcome instability caused in certain hydrocarbonaceous base fuels by the presence of typical manganese carbonyl compounds such as the cyclopentadienyl manganese tricarbonyls in combination with typical metal detergents.
- the most preferred metal deactivators of this type are N,N'- disalicylidene-1,2-alkanediamines and N,N'-disalicylidene-1,2-cycloalkanediamines, especially N,N'- disalicylidene-1,2-propanediamine. Mixtures of metal deactivators can be used.
- Hydrocarbonaceous fuels In principle, the advantages of this invention may be achieved in any liquid hydrocarbonaceous fuel derived from petroleum, coal, shale and/or tar sands. In most instances, at least under present circumstances, 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) hydrocarbonaceous product suitable for combustion either in an engine (e.g., diesel fuel, gas turbine fuels, etc.) or in a burner apparatus (e.g., gas oils, inland heavy fuel oil, residual fuel oils, visbreaker fuel oils, home heating oils, etc.).
- an engine e.g., diesel fuel, gas turbine fuels, etc.
- a burner apparatus e.g., gas oils, inland heavy fuel oil, residual fuel oils, visbreaker fuel oils, home heating oils, etc.
- suitable fuels may 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; or waste oils and/or liquid waste biomass and its derivatives; or mixtures of any of the foregoing substances.
- vegetable oils e.g., rapeseed oil, jojoba oil, cottonseed oil, etc.
- refuse-derived liquid fuels such as fuels derived from municipal and/or industrial wastes; or waste oils and/or liquid waste biomass and its derivatives; or mixtures of any of the foregoing substances.
- the additive compositions comprising components a), b), c) and at least one of components d), e) and f) --preferably two of components d), e) and f) and most preferably all three of components d), e) and f) -are especially useful in heating gas oils and like burner fuels and fuel oils for agricultural and industrial engines.
- Typical specifications for such fuel oils can be found, for example, in BS 2869 : Part 2 : 1988 of the British Standards Institution.
- a vast number of such specifications exist from country to country.
- 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 hydrocarbonaceous 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:
- the individual components a), b), and c), and also d), e), and/or f) (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 in a 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.
- the additive concentrates of this invention will contain components a), b), and c), and optionally, but preferably, one or more of components d), e), and f) in amounts proportioned to yield fuel blends consistent with the concentrations tabulated above.
- the additive concentrate will contain one or more diluents such as light mineral oils, to facilitate handling and blending of the concentrate.
- concentrates containing up to 90% by weight of one or more diluents or solvents are frequently used.
- the additive compositions and fuel compositions of this invention can also contain antioxidant, e.g., one or more phenolic antioxidants, aromatic amine antioxidants, sulphurised phenolic antioxidants, and organic phosphites, among others.
- antioxidant e.g., one or more phenolic antioxidants, aromatic amine antioxidants, sulphurised phenolic antioxidants, and organic phosphites, among others.
- Examples include 2,6-di-tert-butylphenol, liquid mixtures of tertiary butylated phenols, 2,6-di-tert-butyl-4-methylphenol, 4,4'-methy!enebis(2,6-di-tert-buty!pheno!), 2,2'-methylenebis(4-methyl-6-tert-butylphenol), mixed methylene- bridged polyalkyl phenols, 4,4'-thiobis(2-methyl-6-tert-butylphenol), N,N'-di-sec-butyl-p-phenylenediamine, 4-isopropylaminodiphenyl amine, phenyl-a-naphthyl amine, and phenyl-Q-naphthylamine.
- Corrosion inhibitors comprise another type of optional additive for use in this invention.
- dimer and trimer acids such as are produced from tall oil fatty acids, oleic acid, linoleic acid, or the like. Products of this type are currently available from various commercial sources, such as, for example, the dimer and trimer acids sold under the HYSTRENE trademark by the Humco Chemical Division of Witco Chemical Corporation and under the EMPOL trademark by Emery Chemicals.
- alkenyl succinic acid and alkenyl succinic anhydride corrosion inhibitors such as, for example, tetrapropenylsuccinic acid, tetrapropenylsuccinic anhydride, tetradecenylsuccinic acid, tetradecenylsuccinic anhydride, hexadecenylsuccinic acid, hexadecenylsuccinic anhydride, and the like.
- half esters of alkenyl succinic acids having 8 to 24 carbon atoms in the alkenyl group with alcohols such as the polyglycols.
- Preferred materials are the aminosuccinic acids or derivatives thereof represented by the formula: wherein each of R 1 , R 2 , R 5 , R 6 and R 7 is, independently, a hydrogen atom or a hydrocarbyl group containing 1 to 30 carbon atoms, and wherein each of R 3 and R 4 is, independently, a hydrogen atom, a hydrocarbyl group containing 1 to 30 carbon atoms, or an acyl group containing from 1 to 30 carbon atoms.
- R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 when in the form of a hydrocarbyl group, can be, for example, alkyl, cycloalkyl or aromatic containing groups.
- R 1 and R 5 are the same or different straight-chain or branched-chain hydrocarbon radicals containing 1-20 carbon atoms.
- R 1 and R 5 are saturated hydrocarbon radicals containing 3-6 carbon atoms.
- R 2 , either R 3 or R 4 , R 6 and R 7 when in the form of hydrocarbyl groups, are preferably the same or different straight-chain or branched-chain saturated hydrocarbon radicals.
- a dialkyl ester of an aminosuccinic acid is used in which R 1 and R 5 are the same or different alkyl groups containing 3-6 carbon atoms, R 2 is a hydrogen atom, and either R 3 or R 4 is an alkyl group containing 15-20 carbon atoms or an acyl group which is derived from a saturated or unsaturated carboxylic acid containing 2-10 carbon atoms.
- R 1 and R 5 are isobutyl
- R 2 is a hydrogen atom
- R 3 is octadecyl and/or octadecenyl
- R 4 is 3-carboxy-1-oxo-2-propenyl.
- R 6 and R 7 are most preferably hydrogen atoms.
- the heavier fuels of this invention may contain cold flow improvers and pour-point depressants, e.g., olefin/vinyl acetate copolymers such as ethylene/vinyl acetate copolymers and polymethacrylates. Antifoam agents such as silicones, and dyes can also be used in the compositions of this invention.
- the diesel fuels may contain cetane improvers such as peroxy compounds and organic nitrates (e.g., amyl nitrates, hexyl nitrates, heptyl nitrates, octyl nitrates, and other alkyl nitrates having about 4 to about 10 carbon atoms including mixtures thereof).
- alkyl nitrates are cyclohexyl nitrate, methoxypropyl nitrate, mixed nitrate esters made by nitration of fusel oil, 2-ethylhexyl nitrate, n-octyl nitrate, n-decyl nitrate, etc.
- Typical peroxy compounds include acetyl peroxide, benzoyl peroxide, tert-butylperox- yacetate, and cumene hydroperoxide.
- An additive composition is formed by blending together the following components in the amounts specified:
- This composition is well adapted for use in heating gas oil, for example at treat rates of 250 to 37,000 ppm, typically 500 ppm.
- An additive composition of this invention is formed using the following: 76.3% Heavy aromatic naphtha.
- This composition is useful, for example at treat rates of 250 to 37,000 ppm, typically 500 ppm, in heating gas oils.
- this additive concentrate When used, for example at a concentration in the range of 200 to 26,500 ppm, typically 400 ppm, this additive concentrate is especially adapted for improving combustion of road diesel fuels.
- An additive concentrate is formed using the following components:
- Examples 4 and 5 are repeated substituting in one case overbased potassium sulphonate and in another case overbased calcium phenate for the sulphonates of Examples 4 and 5.
- Examples 1 through 3 The procedures of Examples 1 through 3 are repeated except that in one case the overbased calcium sulphonate is replaced by an equivalent amount of overbased magnesium sulphonate, in another case by an equivalent amount of overbased sodium sulphonate, and in a third case by an equivalent amount of overbased potassium sulphonate.
- compositions of Examples 1 through 3 are formed with the exception that the methylcyclopentadienyl manganese tricarbonyl is replaced in one case by an equivalent amount of cyclopentadienyl manganese tricarbonyl, in another case by an equivalent amount of cyclopentadienyl manganese dicarboxyl triphenylphosphine, in a third case by an equivalent amount of indenyl manganese tricarbonyl, in a fourth case by an equivalent amount of dimanganese decacarbonyl, and in still another case by an equivalent amount of a mixture composed of 90% methylcyclopentadienyl manganese tricarbonyl and 10% cyclopentadienyl manganese tricarbonyl.
- compositions of Examples 1 and 2 are blended at concentrations of 300, 500 and 1,000 ppm in a heating gas oil having a specific gravity at 15 °C (DIN 51 757) of 0.845 g/mL, a kinematic viscosity at 20°C (DIN 51 562) of 5.3 mm 2 per second, a pour point (DIN ISO 3016) of -9°C, a sulphur content (DIN 51 400) of 0.19%, and a distillation profile (DIN 51 751) of 27 volume % boiling to 250 ° C and 92 volume % boiling to 350 °C.
- Example 9 is repeated except that the same amounts of the respective components of the respective compositions of Examples 1 and 2 are blended individually or in sub-combinations into the gas oil.
- Example 3 The composition of Example 3 is blended at concentrations of 300, 500, 1,000 and 1,500 ppm in a diesel fuel satisfying the requirements of DIN 51 601-DK (February 1986).
- Example 11 is repeated except that the same amounts of the respective components of the composition of Example 3 are blended individually or in sub-combinations into the diesel fuel.
- Examples 9 and 10 are repeated using as the fuels commercially-available heavy fuel oils and residual oils (e.g., industrial and refinery fuel oils) such as inland heavy fuel oils, and also hydrocarbonaceous marine fuels.
- the additive treat levels in these fuels are 500, 800 and 1,500 ppm.
- An additive composition is formed by blending together the following components in the amounts specified:
- This composition is well adapted for use in heating gas oil, for example at treat rates of 250 to 37,000 ppm, typically 500 ppm.
- Example 15 The procedure of Example 15 is repeated using the following proportions of the additive components: 75.0% Heavy aromatic naphtha.
- Example 15 The procedure of Example 15 is repeated using the following proportions of the additive components:
- Standard CFR engine tests (ASTM D613) were conducted using two different diesel fuels having cetane values of 52.7 (Fuel A) and 52.5 (Fuel B), respectively. Addition of 500 ppm of the composition of Example 1 to Fuel A caused no change in cetane rating. In Fuel B only a slight loss in cetane value (from 52.5 to 51.6) occurred by addition of 500 ppm of the composition of Example 1.
- the same fuels were subjected to thermal stability tests wherein the sample is heated at 150°C for 90 minutes, filtered through a filter and the reflectance of the deposit on the filter measured.
- the rating scale ranges from 0 (clean) to 20 (black). A rating of 7 or less is considered good.
- Thermal oxidative stability tests according to ASTM D 2274 were also performed on these fuels. The performance in these tests is expressed in terms of milligrams of deposit per 100 milliliters of fuel. The results were as follows:
- the fuels of this invention generally possess enhanced combustion properties (e.g., less smoke, lower soot acidity) and better thermal stability than the corresponding untreated fuels.
- use of the fuels of this invention results in the formation of reduced amounts of sludge deposits on critical engine or burner parts or surfaces. Further, such fuels tend to emit smaller amounts of noxious emissions than the corresponding untreated base fuels.
- this invention enables the provision of fuel compositions having enhanced demulsification properties and reduced corrosion tendencies with minimal interference with other desirable fuel properties.
- the results of the foregoing tests also indicate that the additive compositions of this invention can result in decreased fuel consumption in diesel engines.
- the data also indicate that all fuels do not necessarily respond to the same extent to treatment with the additive systems of this invention. Nonetheless, as a general proposition, the fuels of this invention do have significantly improved properties.
- Also included among the embodiments of this invention are methods of improving the combustion characteristics of an at least predominantly hydrocarbonaceous liquid fuel during combustion in an engine, burner, or other combustion apparatus which comprises operating said engine, burner or other combustion apparatus on an at least predominantly hydrocarbonaceous liquid fuel containing a minor combustion-improving amount of:
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Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE90310322T DE69004692T2 (de) | 1990-09-20 | 1990-09-20 | Kohlenwasserstoffzusammensetzungen und Zusätze dafür. |
ES90310322T ES2060058T3 (es) | 1990-09-20 | 1990-09-20 | Composiciones de combustible hidrocarbonado y aditivos para las mismas. |
EP90310322A EP0476196B1 (de) | 1990-09-20 | 1990-09-20 | Kohlenwasserstoffzusammensetzungen und Zusätze dafür |
CA002051452A CA2051452C (en) | 1990-09-20 | 1991-09-16 | Hydrocarbonaceous fuel compositions and additives therefor |
JP3265442A JPH04234489A (ja) | 1990-09-20 | 1991-09-18 | 炭化水素性燃料およびその添加剤 |
AU84650/91A AU635158B2 (en) | 1990-09-20 | 1991-09-20 | Hydrocarbonaceous fuel compositions and additives therefor |
US09/107,577 US5944858A (en) | 1990-09-20 | 1998-02-17 | Hydrocarbonaceous fuel compositions and additives therefor |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP90310322A EP0476196B1 (de) | 1990-09-20 | 1990-09-20 | Kohlenwasserstoffzusammensetzungen und Zusätze dafür |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0476196A1 true EP0476196A1 (de) | 1992-03-25 |
EP0476196B1 EP0476196B1 (de) | 1993-11-18 |
Family
ID=8205552
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP90310322A Expired - Lifetime EP0476196B1 (de) | 1990-09-20 | 1990-09-20 | Kohlenwasserstoffzusammensetzungen und Zusätze dafür |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0476196B1 (de) |
JP (1) | JPH04234489A (de) |
AU (1) | AU635158B2 (de) |
CA (1) | CA2051452C (de) |
DE (1) | DE69004692T2 (de) |
ES (1) | ES2060058T3 (de) |
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WO1993008244A1 (en) * | 1991-10-18 | 1993-04-29 | Exxon Chemical Patents Inc. | Fuel oil compositions |
EP0557516A4 (de) * | 1991-09-13 | 1993-07-06 | Chevron Res & Tech | Polyisobutenylsuccinimide enthaltende brennstoffzusammensetzungen. |
EP0569228A1 (de) * | 1992-05-06 | 1993-11-10 | Ethyl Petroleum Additives, Inc. | Inzufuhranlage für Niederschläge kontrollierende Zusammensetzungen |
EP0587552A1 (de) * | 1992-08-03 | 1994-03-16 | Loba Feinchemie Aktiengesellschaft | Zusatzstoff für Mineralöle und Mineralölprodukte, speziell elektroisolieröle |
EP0634472A1 (de) * | 1993-07-12 | 1995-01-18 | Ethyl Petroleum Additives Limited | Zusammensetzungen um Ablagerungen, Auspuffausströmungen und/oder Kraftstoffverbrauch in Innenverbrennungsmotoren zu Regeln |
WO1995003377A1 (en) * | 1993-07-22 | 1995-02-02 | Exxon Chemical Patents Inc. | Additives and fuel compositions |
WO1995004117A1 (en) * | 1993-08-03 | 1995-02-09 | Exxon Chemical Patents Inc. | Additive for hydrocarbon oils |
WO1995010582A1 (en) * | 1993-10-13 | 1995-04-20 | Exxon Chemical Patents Inc. | Fuel additives |
GB2285057A (en) * | 1993-12-23 | 1995-06-28 | Ethyl Petroleum Additives Ltd | Evaporative burner fuels and additives therefor |
EP0681023A1 (de) * | 1994-05-04 | 1995-11-08 | Ethyl Petroleum Additives Limited | Verträgliche Brennstoffzusatzkonzentrate |
WO1995033022A1 (en) * | 1994-05-31 | 1995-12-07 | Orr William C | Vapor phase combustion methods and compositions |
US5511517A (en) * | 1994-02-10 | 1996-04-30 | Ethyl Corporation | Reducing exhaust emissions from otto-cycle engines |
WO1996015209A1 (en) * | 1994-11-16 | 1996-05-23 | Bp Chemicals (Additives) Limited | Process for reducing liner lacquering in a marine diesel engine and fuel therefor |
WO1996025473A1 (en) * | 1995-02-17 | 1996-08-22 | Bp Chemicals (Additives) Limited | Diesel fuels |
US5551957A (en) * | 1992-05-06 | 1996-09-03 | Ethyl Corporation | Compostions for control of induction system deposits |
WO1996034074A1 (en) * | 1995-04-24 | 1996-10-31 | The Associated Octel Company Ltd. | Improved combustion |
WO1996040844A1 (en) * | 1995-06-07 | 1996-12-19 | Orr William C | Vapor phase combustion method and compositions ii |
AU677114B2 (en) * | 1993-12-23 | 1997-04-10 | Afton Chemical Limited | Evaporative burner fuels and additives therefor |
EP0807677A2 (de) * | 1996-05-14 | 1997-11-19 | Ethyl Corporation | Verbesserte Kohlenwasserstoffenbrennerkraftstoffeverbrennung |
WO1997044414A1 (en) * | 1996-05-20 | 1997-11-27 | Bp Chemicals (Additives) Limited | Marine diesel process and fuel therefor |
EP0829527A1 (de) * | 1996-09-12 | 1998-03-18 | Exxon Research And Engineering Company | Zusatzkonzentrat für Kraftstoffzusammensetzungen |
WO1998012282A1 (en) * | 1996-09-19 | 1998-03-26 | Texaco Development Corp. | Detergent additive compositions for diesel fuels |
EP0859040A1 (de) * | 1997-02-17 | 1998-08-19 | Ethyl Petroleum Additives Limited | Schmierzusatzverwendung zur Schaumverminderung in Brennstoffen |
EP0874039A1 (de) * | 1997-04-23 | 1998-10-28 | The Lubrizol Corporation | Dieselbrennstoffzusammensetzungen |
EP0894845A1 (de) * | 1997-08-01 | 1999-02-03 | Ethyl Corporation | Phosphorylierte und/oder borierte Dispergiermittel, als Destillatbrennstoffwärmebeständigkeitszusätze |
WO1999036489A1 (en) * | 1998-01-13 | 1999-07-22 | Baker Hughes Incorporated | Composition and method to improve lubricity in fuels |
US6070558A (en) * | 1994-11-16 | 2000-06-06 | The Lubrizol Corporation | Process for reducing liner lacquering in a marine diesel engine and fuel therefor |
WO2000058422A1 (en) * | 1999-03-26 | 2000-10-05 | Infineum International Limited | Fuel oil compositions |
EP1063276A1 (de) * | 1999-06-22 | 2000-12-27 | Ethyl Corporation | Phosphorylierte wärmebeständige Destillatbrennstoffzusätze |
WO2001038465A1 (en) * | 1999-11-24 | 2001-05-31 | The Lubrizol Corporation | Improved detergents for use in preventing formation of iron complexes in hydrocarbon fuels |
WO2001088362A1 (en) * | 2000-05-16 | 2001-11-22 | Infineum International Limited | Process for operating diesel engines |
WO2002012417A1 (en) * | 2000-08-03 | 2002-02-14 | Cesare Pedrazzini | Additive for reducing particulate in emissions deriving from the combustion of diesel oil |
US6361573B1 (en) * | 1999-08-31 | 2002-03-26 | Ethyl Corporation | Fuel dispersants with enhanced lubricity |
US6488724B1 (en) | 1996-10-30 | 2002-12-03 | Clariant Gmbh | Heavy oils having improved properties and an additive therefor |
EP1344809A1 (de) * | 2002-03-13 | 2003-09-17 | Infineum International Limited | Dieselkraftstoffzusatzzusammensetzungen zur Partikelfalleverbesserung |
WO2003106595A2 (en) * | 2002-06-14 | 2003-12-24 | The Lubrizol Corporation | Jet fuel additive concentrate composition and fuel composition and methods thereof |
US6790343B2 (en) | 1998-12-29 | 2004-09-14 | China Petro-Chemical Corporation | Sulfur transfer additive for catalytic cracking of hydrocarbons and a catalytic cracking process of hydrocarbons using the same |
EP1484388A1 (de) * | 2003-06-04 | 2004-12-08 | Shell Internationale Researchmaatschappij B.V. | Reduzierung von Korrosion in Boiler |
EP1484387A1 (de) * | 2003-06-04 | 2004-12-08 | Shell Internationale Researchmaatschappij B.V. | Reduzierung von Korrosion in Boiler |
EP1496100A1 (de) * | 2003-07-08 | 2005-01-12 | Ethyl Petroleum Additives, Inc. | Destillattreibstoffezusammensetzungen zur Verbesserung der Verbrennung und der Motorsauberkeit. |
WO2007042887A1 (en) * | 2005-10-12 | 2007-04-19 | Nalco Company | Composition and method for enhancing the stability of jet fuels |
EP1847583A2 (de) * | 2006-04-21 | 2007-10-24 | Infineum International Limited | Verbesserungen bei Biokraftstoff |
WO2008084251A1 (en) * | 2007-01-11 | 2008-07-17 | Innospec Limited | Composition, method and use |
US7402186B2 (en) | 2004-02-09 | 2008-07-22 | The Lubrizol Corporation | Fuel composition containing a medium substantially free of sulphur and process thereof |
US8211190B2 (en) | 1999-03-26 | 2012-07-03 | Infineum International Limited | Fuel oil compositions |
WO2013007738A1 (fr) * | 2011-07-12 | 2013-01-17 | Total Raffinage Marketing | Compositions d'additifs ameliorant la stabilite et les performances moteur des gazoles |
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AU661604B2 (en) * | 1992-08-17 | 1995-07-27 | General Electric Company | Endothermic fuel additive to inhibit catalyst coking |
JP2004035882A (ja) * | 2002-07-03 | 2004-02-05 | Infineum Internatl Ltd | 粒状物トラップ改良のための過塩基化金属塩ディーゼル燃料添加剤組成物 |
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US7094274B2 (en) * | 2003-04-17 | 2006-08-22 | Afton Chemical Intangibles Llc | Use of manganese compounds to improve the efficiency of and reduce back-corona discharge on electrostatic precipitators |
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ES2245872B2 (es) * | 2004-03-22 | 2006-12-01 | Repsol Ypf, S.A. | Composicion de gasoleo o combustible destilado medio estabilizado. |
DE102005032119A1 (de) * | 2005-07-07 | 2007-01-18 | Octel Deutschland Gmbh | Russarm verbrennendes Heizöl |
BRPI0706618A2 (pt) * | 2006-01-18 | 2011-04-05 | Basf Se | uso de misturas, e , concentrado de aditivo de combustìvel |
AU2009292637A1 (en) * | 2008-09-17 | 2010-03-25 | Exxonmobil Research And Engineering Company | Method for improving the oxidation stability of biodiesel as measured by the Rancimat Test |
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- 1990-09-20 EP EP90310322A patent/EP0476196B1/de not_active Expired - Lifetime
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EP0557516A4 (de) * | 1991-09-13 | 1993-07-06 | Chevron Res & Tech | Polyisobutenylsuccinimide enthaltende brennstoffzusammensetzungen. |
EP0557516A1 (de) * | 1991-09-13 | 1993-09-01 | Chevron Res & Tech | Polyisobutenylsuccinimide enthaltende brennstoffzusammensetzungen. |
US5393309A (en) * | 1991-09-13 | 1995-02-28 | Chevron Research And Technology Company | Fuel additive compositions containing polyisobutenyl succinimides |
WO1993008244A1 (en) * | 1991-10-18 | 1993-04-29 | Exxon Chemical Patents Inc. | Fuel oil compositions |
AU668151B2 (en) * | 1992-05-06 | 1996-04-26 | Afton Chemical Corporation | Composition for control of induction system deposits |
EP0569228A1 (de) * | 1992-05-06 | 1993-11-10 | Ethyl Petroleum Additives, Inc. | Inzufuhranlage für Niederschläge kontrollierende Zusammensetzungen |
US5551957A (en) * | 1992-05-06 | 1996-09-03 | Ethyl Corporation | Compostions for control of induction system deposits |
EP0587552A1 (de) * | 1992-08-03 | 1994-03-16 | Loba Feinchemie Aktiengesellschaft | Zusatzstoff für Mineralöle und Mineralölprodukte, speziell elektroisolieröle |
EP0634472A1 (de) * | 1993-07-12 | 1995-01-18 | Ethyl Petroleum Additives Limited | Zusammensetzungen um Ablagerungen, Auspuffausströmungen und/oder Kraftstoffverbrauch in Innenverbrennungsmotoren zu Regeln |
WO1995003377A1 (en) * | 1993-07-22 | 1995-02-02 | Exxon Chemical Patents Inc. | Additives and fuel compositions |
EP0908507A1 (de) * | 1993-07-22 | 1999-04-14 | Exxon Chemical Patents Inc. | Zusätze und Brennstoffzusammensetzungen |
WO1995004117A1 (en) * | 1993-08-03 | 1995-02-09 | Exxon Chemical Patents Inc. | Additive for hydrocarbon oils |
WO1995010582A1 (en) * | 1993-10-13 | 1995-04-20 | Exxon Chemical Patents Inc. | Fuel additives |
GB2285057B (en) * | 1993-12-23 | 1997-12-10 | Ethyl Petroleum Additives Ltd | Evaporative burner fuels and additives therefor |
GB2285057A (en) * | 1993-12-23 | 1995-06-28 | Ethyl Petroleum Additives Ltd | Evaporative burner fuels and additives therefor |
AU677114B2 (en) * | 1993-12-23 | 1997-04-10 | Afton Chemical Limited | Evaporative burner fuels and additives therefor |
US5525127A (en) * | 1993-12-23 | 1996-06-11 | Ethyl Petroleum Additives Limited | Evaporative burner fuels and additives therefor |
US5511517A (en) * | 1994-02-10 | 1996-04-30 | Ethyl Corporation | Reducing exhaust emissions from otto-cycle engines |
EP0681023A1 (de) * | 1994-05-04 | 1995-11-08 | Ethyl Petroleum Additives Limited | Verträgliche Brennstoffzusatzkonzentrate |
WO1995033022A1 (en) * | 1994-05-31 | 1995-12-07 | Orr William C | Vapor phase combustion methods and compositions |
US6070558A (en) * | 1994-11-16 | 2000-06-06 | The Lubrizol Corporation | Process for reducing liner lacquering in a marine diesel engine and fuel therefor |
WO1996015209A1 (en) * | 1994-11-16 | 1996-05-23 | Bp Chemicals (Additives) Limited | Process for reducing liner lacquering in a marine diesel engine and fuel therefor |
AU694809B2 (en) * | 1994-11-16 | 1998-07-30 | Lubrizol Adibis Holdings (Uk) Limited | Process for reducing liner lacquering in a marine diesel engine and fuel therefor |
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WO1996034074A1 (en) * | 1995-04-24 | 1996-10-31 | The Associated Octel Company Ltd. | Improved combustion |
US6056792A (en) * | 1995-04-24 | 2000-05-02 | The Associated Octel Company Limited | combustion |
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WO1996040844A1 (en) * | 1995-06-07 | 1996-12-19 | Orr William C | Vapor phase combustion method and compositions ii |
EP0807677A3 (de) * | 1996-05-14 | 1998-01-07 | Ethyl Corporation | Verbesserte Kohlenwasserstoffenbrennerkraftstoffeverbrennung |
EP0807677A2 (de) * | 1996-05-14 | 1997-11-19 | Ethyl Corporation | Verbesserte Kohlenwasserstoffenbrennerkraftstoffeverbrennung |
WO1997044414A1 (en) * | 1996-05-20 | 1997-11-27 | Bp Chemicals (Additives) Limited | Marine diesel process and fuel therefor |
WO1998011175A1 (en) * | 1996-09-12 | 1998-03-19 | Exxon Research And Engineering Company | Additive concentrate for fuel compositions |
EP0829527A1 (de) * | 1996-09-12 | 1998-03-18 | Exxon Research And Engineering Company | Zusatzkonzentrat für Kraftstoffzusammensetzungen |
US6277158B1 (en) | 1996-09-12 | 2001-08-21 | Exxon Research And Engineering Company | Additive concentrate for fuel compositions |
WO1998012282A1 (en) * | 1996-09-19 | 1998-03-26 | Texaco Development Corp. | Detergent additive compositions for diesel fuels |
US5925151A (en) * | 1996-09-19 | 1999-07-20 | Texaco Inc | Detergent additive compositions for diesel fuels |
US6488724B1 (en) | 1996-10-30 | 2002-12-03 | Clariant Gmbh | Heavy oils having improved properties and an additive therefor |
EP0859040A1 (de) * | 1997-02-17 | 1998-08-19 | Ethyl Petroleum Additives Limited | Schmierzusatzverwendung zur Schaumverminderung in Brennstoffen |
CN1090230C (zh) * | 1997-02-17 | 2002-09-04 | 英国乙基石油添加剂有限公司 | 减少泡沫的润滑性添加剂在燃料中的应用 |
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US6042626A (en) * | 1997-08-01 | 2000-03-28 | Ethyl Corporation | Phosphorylated and/or boronated dispersants as thermal stability additives for distillate fuels |
EP0894845A1 (de) * | 1997-08-01 | 1999-02-03 | Ethyl Corporation | Phosphorylierte und/oder borierte Dispergiermittel, als Destillatbrennstoffwärmebeständigkeitszusätze |
WO1999036489A1 (en) * | 1998-01-13 | 1999-07-22 | Baker Hughes Incorporated | Composition and method to improve lubricity in fuels |
US6129772A (en) * | 1998-01-13 | 2000-10-10 | Baker Hughes Incorporated | Composition and method to improve lubricity in fuels |
US6790343B2 (en) | 1998-12-29 | 2004-09-14 | China Petro-Chemical Corporation | Sulfur transfer additive for catalytic cracking of hydrocarbons and a catalytic cracking process of hydrocarbons using the same |
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US8211190B2 (en) | 1999-03-26 | 2012-07-03 | Infineum International Limited | Fuel oil compositions |
SG93866A1 (en) * | 1999-06-22 | 2003-01-21 | Ethyl Corp | Phosphorylated thermal stability additives for distillate fuels |
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US6361573B1 (en) * | 1999-08-31 | 2002-03-26 | Ethyl Corporation | Fuel dispersants with enhanced lubricity |
WO2001038465A1 (en) * | 1999-11-24 | 2001-05-31 | The Lubrizol Corporation | Improved detergents for use in preventing formation of iron complexes in hydrocarbon fuels |
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WO2001088362A1 (en) * | 2000-05-16 | 2001-11-22 | Infineum International Limited | Process for operating diesel engines |
KR100713447B1 (ko) * | 2000-05-16 | 2007-05-02 | 인피늄 인터내셔날 리미티드 | 디젤 엔진의 작동 방법 |
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WO2003106595A2 (en) * | 2002-06-14 | 2003-12-24 | The Lubrizol Corporation | Jet fuel additive concentrate composition and fuel composition and methods thereof |
WO2003106595A3 (en) * | 2002-06-14 | 2004-02-26 | Lubrizol Corp | AVIATION FUEL ADDITIVE CONCENTRATE COMPOSITION, FUEL COMPOSITION AND RELATED METHODS |
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EP1496100A1 (de) * | 2003-07-08 | 2005-01-12 | Ethyl Petroleum Additives, Inc. | Destillattreibstoffezusammensetzungen zur Verbesserung der Verbrennung und der Motorsauberkeit. |
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Also Published As
Publication number | Publication date |
---|---|
DE69004692T2 (de) | 1994-03-10 |
CA2051452A1 (en) | 1992-03-21 |
JPH04234489A (ja) | 1992-08-24 |
CA2051452C (en) | 2002-11-19 |
DE69004692D1 (de) | 1993-12-23 |
AU8465091A (en) | 1992-03-26 |
AU635158B2 (en) | 1993-03-11 |
ES2060058T3 (es) | 1994-11-16 |
EP0476196B1 (de) | 1993-11-18 |
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