Classifications

• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
  • C10L1/223—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
  • C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
  • C10L1/1832—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom mono-hydroxy
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/192—Macromolecular compounds
  • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
  • C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L10/00—Use of additives to fuels or fires for particular purposes
  • C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
• • 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
  • C10L2200/00—Components of fuel compositions
  • C10L2200/04—Organic compounds
  • C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
  • C10L2200/0415—Light distillates, e.g. LPG, naphtha
  • C10L2200/0423—Gasoline
• • 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
  • C10L2270/00—Specifically adapted fuels
  • C10L2270/02—Specifically adapted fuels for internal combustion engines
  • C10L2270/023—Specifically adapted fuels for internal combustion engines for gasoline engines

Definitions

• diarylamines to reduce and/or eliminate deposits on intake valves of spark ignition engines, a method of operating them and methods of reducing intake valve deposits.
• Diarylamines have long been known as fuel additives.
• WO 2018/041710 A1 describes the use of diarylamines in direct-injection gasoline engines to reduce combustion chamber deposits or the injection nozzle. Thus, only the reduction of coking on components that are in contact with combustion gases is described.
• the present invention relates to the reduction and/or elimination of deposits that are on the intake valves of indirect injection gasoline engines, so-called intake valve deposits (IVD): These deposits are on the inside of the intake valves on the intake manifold side Area of the intake valve that comes into contact with a fuel-air mixture.
• the valves are thermally connected to the combustion chamber, so that they have a higher wall temperature than when stored in the tank or conveyed in the fuel system, to which the fuel-air mixture is exposed.
• the insides of the valves are not exposed to the combustion process, so that the problem of deposits is different here than according to the WO 2018/041710 A1 .
• the object of the present invention was to provide gasoline additives with which the deposits on the intake valves of indirect-injection Otto engines can be reduced or eliminated.
• the object was achieved by using at least one diarylamine in a fuel or fuel additive to reduce and/or eliminate deposits on the intake valves (IVD) in Otto engines with indirect injection.
• Another object of the present invention is a method for operating a gasoline engine with indirect injection using a gasoline containing at least one diarylamine to reduce and/or eliminate deposits on the intake valves (IVD).
• Diarylamines are generally those amines in which the amine nitrogen atom is directly attached to two aromatic rings. The aromatic rings can be unsubstituted or substituted with one or more substituents.
• alkyl radical having 1 to 20 carbon atoms for example methyl, ethyl, isopropyl , n-propyl, n-butyl, isobutyl , sec-butyl, tert-butyl, n-hexyl, n-heptyl, n-octyl, 2- ethylhexyl, n-decyl, 2-propylheptyl n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl or n-eicosyl.
• Methyl, ethyl, iso -propyl, iso -butyl, tert-butyl, n-hexyl, n-octyl, 2-ethylhexyl, n-decyl, 2-propylheptyl, n-dodecyl, n-tetradecyl or n-hexadecyl are particularly preferred methyl, isopropyl , tert-butyl and 2-ethylhexyl are preferred.
• Alkenyl radicals having 2 to 20 carbon atoms are vinyl, allyl, isopropenyl, octenyl, decenyl, dodecenyl, tetradecenyl, hexadecenyl and octadecenyl.
• hydroxyalkyl radicals having 1 to 4 carbon atoms are hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxypropyl and 2-hydroxyprop-2-yl.
• R 1 and R 2 are preferably, independently of one another, hydrogen, methyl, isopropyl, tert. butyl, 2-ethylhexyl, hydroxymethyl or 2-hydroxyprop-2-yl.
• R 1 and R 2 are the same.
• Preferred diphenylamines are diphenylamine, dinaphthylamine, 4,4'-di(dimethylbenzyl)diphenylamine ( CAS 10081-67-1 ), 4-hydroxydiphenylamine ( CAS 122-37-2 ), 4-Methoxy-2-methyldiphenylamine ( CAS 41317-15-1 ), alkylated diphenylamines, reaction product of diphenylamine with 2,4,4-trimethylpentene ( CAS 68411-46-1 , Irganox ® L57), reaction product of styrene with diphenylmethane ( CAS 68442-68-2 ), p-aminodiphenylamine ( CAS 101-54 -), 4-isopropylaminodiphenylamine ( CAS 101-72-4 ), bis(nonyl)diphenylamine (reaction product of diphenylamine with nonene, bis(4-(1,1,3,3-tetramethylbuty
• diphenylamine or N-phenyl-naphthylamine can be reacted with isobutene, diisobutene, nonene, styrene, ⁇ -methylstyrene or propylene tetramer using suitable catalysts to give mixtures of mono- and disubstituted products as particularly preferred dipjenylamines.
• Reaction products from the reaction of diphenylamine with mixtures of the olefins mentioned can also be used.
• reaction product of diphenylamine with 2,4,4-trimethylpentene (CAS 68411-46-1 , Irganox ® L57) and butylated, octylated diphenylamine (Naugalube ® 640).
• the above identified diphenylamine is used in a fuel additive package together with at least one sterically hindered phenol and/or aminophenol, preferably at least one sterically hindered phenol.
• Preferred sterically hindered phenols have the formula
• alkyl radicals having 1 to 20 carbon atoms alkenyl radicals having 2 to 20 carbon atoms and alkyl radicals having 4 to 16 carbon atoms correspond to the definitions and individuals given for the diphenylamines.
• Preferred radicals R 10 , R 11 and R 12 are, independently of one another, methyl, ethyl, isopropyl , isobutyl , tert -butyl, n-hexyl, n-octyl, 2-ethylhexyl, n-decyl, 2-propylheptyl n- Dodecyl, n-tetradecyl or n-hexadecyl, particular preference is given to methyl, isopropyl , tert -butyl and 2-ethylhexyl and very particular preference to methyl and tert. butyl.
• R 12 can additionally preferably be hydrogen, 2-(methoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl, 2-(n-butyloxycarbonyl)ethyl, 2-(tert-butyloxycarbonyl)ethyl, 2-(n-octyloxycarbonyl)ethyl or 2- (2'-ethylhexyloxycarbonyl)ethyl.
• Preferred sterically hindered phenols are 2,6-di tert. butyl phenol, 2-tert-butyl-4-methylphenol, 6-tert-butyl-2,4-dimethyl-phenol, 2,6-di-tert-butyl-4-methylphenol, 2-tert-butylphenol, 4- tert-butylphenol, 2,4-di-tert-butylphenol, 2-methyl-4-tert-butylphenol, 4-tert-butyl-2,6-dimethylphenol, 2-tert-butyl-6-methylphenol, 2,4,6-Tris-tert-butylphenol, 2,6-di-tert-butylphenol, 2,4-di-tert-butylphenol, 2,6-dimethylphenol, 2,6-di-tert-butyl- p-cresol, 3-(3',5'-di- tert -butyl-4'-hydroxyphenyl)propionic acid octadec
• the amino and the phenolic hydroxy group can be in the ortho, meta or para position to one another, preferably ortho or para.
• the amino group can be unsubstituted in the form of an -NH 2 group, or mono. or disubstituted, preferably disubstituted.
• the substituents can be the same or different, and are preferably C 1 -C 4 -alkyl or hydroxy-C 1 -C 4 -alkyl.
• the preparation route by hydroformylation and subsequent amination under reductive (hydrogenating) conditions is an option.
• Amines such as ammonia, monoamines or polyamines such as dimethylaminopropylamine, ethylenediamine, diethylenetriamine, triethylenetetramine or tetraethylenepentamine can be used for the amination.
• Corresponding additives based on polypropylene are in particular in the WO-A-94/24231 described.
• additives containing monoamino groups are the compounds obtainable from polyisobutene epoxides by reaction with amines and subsequent dehydration and reduction of the amino alcohols, as they are particularly DE-A-196 20 262 are described.
• Additives containing groups produced by Mannich reaction of substituted phenols with aldehydes and mono- or polyamines are preferably reaction products of polyisobutene-substituted phenols with formaldehyde and mono- or polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine or especially dimethylaminopropylamine.
• Such "polyisobutene Mannich bases" are particularly in the EP-A-831 141 described.
• the anion can have multiple negative charges, for example in the case of anions of dicarboxylic acids.
• the stoichiometric ratio of ammonium ions to anions corresponds to the ratio of the respective positive and negative charges.
• the detergent additives mentioned are usually added to the fuel in an amount of 10 to 5000 ppm by weight, in particular 50 to 1000 ppm by weight.
• the other components and additives mentioned are added, if desired, in amounts customary for this purpose.
• the diphenylamine described above is used in a fuel additive package which additionally contains at least one carrier oil, preferably a polyalkoxylate.
• Carrier oils do not normally exhibit pronounced detergency.
• Suitable mineral carrier oils are fractions obtained during petroleum processing, such as bright stock or base oils with viscosities such as those from the class SN 500-2000; but also aromatic hydrocarbons, paraffinic hydrocarbons and alkoxyalkanols. Also usable is a fraction known as "hydrocrack oil” and obtained in the refining of mineral oil (vacuum distillate cut having a boiling range of about 360 to 500°C, obtainable from natural mineral oil which has been catalytically hydrogenated and isomerized and dewaxed under high pressure). Mixtures of the mineral carrier oils mentioned above are also suitable.
• Examples of synthetic carrier oils that can be used according to the invention are selected from: polyolefins (polyalphaolefins or polyinternal olefins), (poly)esters, (poly)alkoxylates, polyethers, alkanol- or alkylphenol-started polyethers (polyalkoxylates), alkylphenol- or alkanol-started polyetheramines (polyethers, in in which at least one hydroxy group is replaced by an amino group) and carboxylic acid esters of long-chain alkanols.
• polyolefins polyalphaolefins or polyinternal olefins
• (poly)esters poly)alkoxylates
• polyethers alkanol- or alkylphenol-started polyethers (polyalkoxylates)
• alkylphenol- or alkanol-started polyetheramines polyethers, in in which at least one hydroxy group is replaced by
• polyethers or polyetheramines are preferably compounds containing polyoxy-C 2 -C 4 -alkylene groups, which are obtained by reacting C 2 -C 60 -alkanols, C 6 -C 30 -alkanediols, mono- or di-C 2 -C 30 -alkylamines, C 1 -C 30 -alkylcyclohexanols or C 1 -C 30 -alkylphenols with 1 to 30 mol of ethylene oxide and/or propylene oxide and/or butylene oxide per hydroxyl group or amino group and, in the case of polyetheramines, by subsequent reductive amination with ammonia , monoamines or polyamines are available.
• poly-C 2 -C 6 -alkylene oxide amines or functional derivatives thereof can be used as polyetheramines.
• Preferred examples of polyalkoxylates are tridecanol or isotridecanol butoxylates, isoheptadecanol butoxylates, isononylphenol butoxylates and polyisobutenol butoxylates and propoxylates and the corresponding reaction products with ammonia.
• carboxylic acid esters of long-chain alkanols are, in particular, esters of mono-, di- or tricarboxylic acids with long-chain alkanols or polyols, such as those in particular DE-A-38 38 918 are described.
• Aliphatic or aromatic acids can be used as mono-, di- or tricarboxylic acids, and long-chain representatives having, for example, 6 to 24 carbon atoms are particularly suitable as ester alcohols or ester polyols.
• esters are adipates, phthalates, isophthalates, terephthalates and trimellitates of isooctanol, isononanol, isodecanol and isotridecanol, such as di-(n- or isotridecyl)phthalate.
• suitable synthetic carrier oils are alcohol-started polyethers having about 5 to 35, such as about 5 to 30, C 3 -C 6 -alkylene oxide units, such as selected from propylene oxide, n-butylene oxide and i-butylene oxide units, or mixtures of that.
• suitable starter alcohols are long-chain alkanols or phenols substituted with long-chain alkyl, where the long-chain alkyl radical is in particular a straight-chain or branched C 6 -C 18 -alkyl radical.
• Preferred examples are tridecanol, heptadecanol and nonylphenol.
• the additive packages according to the invention often contain at least one solvent to reduce the viscosity and/or improve formulatability.
• Suitable are, for example, non-polar organic solvents such as aromatic and aliphatic hydrocarbons, for example toluene, xylenes, "white spirit” and products sold under the trade names SHELLSOL (Royal Dutch/Shell Group) and EXXSOL (ExxonMobil), as well as polar organic solvents, for example Alcohols such as 2-ethylhexanol, decanol and isotridecanol.
• solvents usually get into the fuel together with the aforementioned additives and co-additives, which they are supposed to dissolve or dilute for better handling.
• customary additives are corrosion inhibitors, for example based on film-forming ammonium salts of organic carboxylic acids or on heterocyclic aromatics in the case of non-ferrous metal corrosion protection;
• Antioxidants or stabilizers for example based on amines such as p-phenylenediamine, dicyclohexylamine or derivatives thereof, or on phenols such as 2,4-di-tert-butylphenol or 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid; demulsifiers; antistatic agents; lubricity improvers, such as certain fatty acids, alkenyl succinic acid esters, bis(hydroxyalkyl) fatty amines, hydroxyacetamides or castor oil; and dyes (markers). If necessary, amines are also added to lower the pH of the fuel.
• the components or additives can be added to the fuel individually or as a previously prepared concentrate (additive package) together with the diphenylamine according to the invention.
• Such additive packages contain at least one diphenylamine and optionally at least one of the other additives specified above.
• preferred additive packages also contain at least one sterically hindered phenol and optionally at least one of the other additives specified above.
• At least one diphenylamine, at least one sterically hindered phenol, and the at least one detergent particularly preferred additive packages also contain at least one carrier oil, preferably selected from the group consisting of polyalkoxylates and polyetheramines, particularly preferably at least one polyalkoxylate, and optionally at least one of the above other additives.
• the additive packages are usually added to the gasoline in amounts of 100 to 3000 ppm by weight, preferably in amounts of 200 to 2500, particularly preferably 500 to 2000 ppm by weight.
• Another object of the present invention is the use of such additive packages in a fuel to reduce and/or eliminate deposits on the intake valves (IVD) in indirect injection spark-ignition engines.
• IVD intake valves
• a further object of the present invention is a method for operating a gasoline engine with indirect injection with a gasoline containing at least one such additive package for reducing and/or eliminating deposits on the intake valves (IVD).
• additive compositions listed can be used in all conventional gasoline fuels, as described, for example, in Ullmann's Encyclopedia of Industrial Chemistry, 5th edition 1990, Volume A16, p. 719 et seq.
• a gasoline with an aromatics content of no more than 60 such as no more than 42 or no more than 35% by volume and/or a sulfur content of no more than 2000, such as no more than 150 or no more than 10 ppm by weight, is possible.
• the aromatics content of petrol is, for example, 10 to 50% by volume, such as 30 to 42% by volume, in particular 32 to 40% by volume, or a maximum of 35% by volume.
• the sulfur content of petrol is, for example, 2 to 500, such as 5 to 100 ppm by weight, or a maximum of 10 ppm by weight.
• the gasoline can, for example, have an olefin content of up to 50% by volume, such as from 6 to 21% by volume, in particular 7 to 18% by volume; a benzene content of up to 5% by volume, such as 0.5 to 1.0% by volume, in particular 0.6 to 0.9% by volume, and/or an oxygen content of up to 25% by volume , such as up to 10% by weight or 1.0 to 2.7% by weight, in particular from 1.2 to 2.0% by weight.
• an olefin content of up to 50% by volume, such as from 6 to 21% by volume, in particular 7 to 18% by volume
• a benzene content of up to 5% by volume, such as 0.5 to 1.0% by volume, in particular 0.6 to 0.9% by volume
• an oxygen content of up to 25% by volume such as up to 10% by weight or 1.0 to 2.7% by weight, in particular from 1.2 to 2.0% by weight.
• petrol fuels that can be mentioned by way of example have an aromatic content of no more than 38 or 35% by volume, an olefin content of no more than 21% by volume, a sulfur content of no more than 50 or 10 ppm by weight, a benzene content of no more than 1, 0% by volume and an oxygen content of 1.0 to 2.7% by weight.
• the gasoline can contain up to 85% by volume, preferably up to 65% by volume, particularly preferably up to 50% by volume, very particularly preferably up to 25% by volume and in particular up to 10% by volume of at least one C 1 -C 4 alkanol contain methanol, ethanol or n-butanol, particularly preferably methanol or ethanol and very particularly preferably ethanol.
• the content of alcohols and ethers in petrol can vary over a wide range. Examples of typical maximum contents are 15% by volume for methanol, 85% by volume for ethanol, 20% by volume for isopropanol, 15% by volume for tert-butanol, 20% by volume for isobutanol and ether with 5 or more carbon atoms in the molecule, 30% by volume. Pure alkanols, especially pure methanol or ethanol, are also conceivable.
• the summer vapor pressure of petrol is usually a maximum of 70 kPa, in particular 60 kPa (each at 37° C.).
• the RON of petrol is usually 75 to 105.
• a typical range for the corresponding MON is 65 to 95.
• the subject of the present invention is a method for operating a vehicle with a spark-ignition engine, in which the spark-ignition fuel used for operation contains at least one diphenylamine to reduce and/or eliminate deposits on the intake valves (IVD).

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• 2021
  • 2021-10-06 EP EP21201213.2A patent/EP4163353A1/fr not_active Withdrawn

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