EP4373903B1 - Verwendung einer additivzusammensetzung zur reduktion der emissionen von dieselfahrzeugen - Google Patents

Verwendung einer additivzusammensetzung zur reduktion der emissionen von dieselfahrzeugen

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Publication number
EP4373903B1
EP4373903B1 EP22754467.3A EP22754467A EP4373903B1 EP 4373903 B1 EP4373903 B1 EP 4373903B1 EP 22754467 A EP22754467 A EP 22754467A EP 4373903 B1 EP4373903 B1 EP 4373903B1
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use according
additive
additives
carbon atoms
group
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English (en)
French (fr)
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EP4373903A1 (de
Inventor
Bernard Dequenne
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TotalEnergies Onetech SAS
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TotalEnergies Onetech SAS
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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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/04—Liquid carbonaceous fuels essentially based on blends of hydrocarbons
    • C10L1/08—Liquid carbonaceous fuels essentially based on blends of hydrocarbons for compression ignition
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
    • C—CHEMISTRY; METALLURGY
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/1811—Organic compounds containing oxygen peroxides; ozonides
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/23—Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites
    • C10L1/231—Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites nitro compounds; nitrates; nitrites
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    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/02—Use of additives to fuels or fires for particular purposes for reducing smoke development
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    • 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
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    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
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    • 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
    • C10L1/1835—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom having at least two hydroxy substituted non condensed benzene rings
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • 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
    • C10L1/1981—Condensation polymers of aldehydes or ketones
    • C—CHEMISTRY; METALLURGY
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    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L2200/00—Components of fuel compositions
    • C10L2200/02—Inorganic or organic compounds containing atoms other than C, H or O, e.g. organic compounds containing heteroatoms or metal organic complexes
    • C10L2200/0254—Oxygen containing 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L2200/00—Components of fuel compositions
    • C10L2200/02—Inorganic or organic compounds containing atoms other than C, H or O, e.g. organic compounds containing heteroatoms or metal organic complexes
    • C10L2200/0259—Nitrogen containing 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L2200/00—Components of fuel compositions
    • C10L2200/04—Organic compounds
    • C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
    • C10L2200/0438—Middle or heavy distillates, heating oil, gasoil, marine fuels, residua
    • C10L2200/0446—Diesel
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L2200/00—Components of fuel compositions
    • C10L2200/04—Organic compounds
    • C10L2200/0461—Fractions defined by their origin
    • C10L2200/0469—Renewables or materials of biological origin
    • C10L2200/0476—Biodiesel, i.e. defined lower alkyl esters of fatty acids first generation biodiesel
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L2270/00—Specifically adapted fuels
    • C10L2270/02—Specifically adapted fuels for internal combustion engines
    • C10L2270/026—Specifically adapted fuels for internal combustion engines for diesel engines, e.g. automobiles, stationary, marine

Definitions

  • the present invention relates to the use of a composition of particular additives for reducing pollutant emissions from vehicles equipped with compression ignition engines or Diesel engines.
  • the present invention also relates to a process or method for reducing pollutant emissions from vehicles equipped with compression ignition engines or diesel engines, using this composition of additives in a fuel.
  • additives are chemical compounds that are incorporated in small quantities into fuels in order to improve their intrinsic performance. Examples include cold-holding additives (aimed at improving fuel performance at low temperatures), deposit-reducing additives (aimed at reducing the fouling effect of fuels in engines during combustion), procetane additives (aimed at increasing the cetane number and therefore the energy performance of fuels), etc.
  • additive manufacturers have done little to address the issue of controlling pollutant emissions.
  • additives are generally considered to have little or no impact on pollutant emissions.
  • pollutants are often treated individually, meaning that a given technology can only reduce one type of pollutant, for example NOx, and not others (for example carbon monoxide, particles, unburned hydrocarbons, etc.). Different technologies must therefore be juxtaposed to meet regulatory requirements.
  • SAE 2000-01-1853 provides information on the benefit in CO and HC linked to the use of procetane but reveals a slight increase in NOx.
  • SAE publication 2009-01-2697 studies the impact of cetane index on a Cummins 6.7L engine and confirms an increase in NOx linked to high cetane indexes (adjusted by the use of procetane).
  • US 5976201 A describes a diesel fuel composition that produces low levels of emissions, particularly such as CO, NOx, unburned hydrocarbons and particulates.
  • this additive composition into a diesel engine fuel makes it possible to obtain a significant reduction in the levels of pollutant emissions compared to the same fuel not containing these additives. Particularly unexpectedly, the reduction is obtained simultaneously for several types of pollutant agents including at least nitrogen oxides, carbon monoxide and/or unburned hydrocarbons.
  • the invention makes it possible to simultaneously reduce emissions of nitrogen oxides, carbon monoxide and unburned hydrocarbons.
  • the invention makes it possible to further reduce emissions of solid particles.
  • the additive composition according to the invention is effective in the different types of fuels intended for diesel engines, also called gas oils, whether of petroleum origin or not, including fuels derived in whole or in part from biomass.
  • the invention also relates to a process or method for reducing emissions of nitrogen oxides and at least one type of polluting agent chosen from carbon monoxide and unburned hydrocarbons during the combustion of a liquid fuel in a compression-ignition internal combustion engine, comprising the addition to said fuel of an additive composition as defined above.
  • C N compound or group denotes a compound or group containing N carbon atoms in its chemical structure.
  • the invention uses as additive (i) one or more compound(s) having in their structure at least one alkyl-phenol group.
  • this or these compounds have in their formula at least one phenolic nucleus (i.e. a benzene nucleus substituted by one or more hydroxyl -OH groups) substituted by one or more alkyl groups.
  • the additive(s) (i) are chosen from compounds (i)a) comprising one or two phenolic nuclei substituted by one or more alkyl groups chosen from methyl and t-butyl (or tert-butyl) groups.
  • These compounds (i)a) may more particularly be chosen from methyl-t-butyl phenols, dimethyl-t-butyl phenols, ethyl-t-butyl phenols, t-butyl phenols, di-t-butyl phenols, tri-t-butyl phenols, di-t-butyl-di-methyl phenols, and mixtures thereof.
  • Preferred compounds are selected from 2,6-di-t-butyl-4-methylphenol (BHT), 4,6-di-tert-butyl-2-methylphenol, t-butyl hydroquinone (TBHQ), 2,6 and 2,4 di-t-butyl phenol, 2,4-dimethyl-6-t-butyl phenol, 2,4,6-tri-t-butyl phenol, 2,3,6-trimethyl phenol, 2,4,6- trimethyl phenol, 4,4'- methylene bis (2,6-di-t-butyl phenol) (No. CASE 1 18-82-1 ), alone or in a mixture.
  • BHT 2,6-di-t-butyl-4-methylphenol
  • TBHQ t-butyl hydroquinone
  • 2,6 and 2,4 di-t-butyl phenol 2,4-dimethyl-6-t-butyl phenol
  • 2,4,6-tri-t-butyl phenol 2,3,6-trimethyl phenol
  • Particularly preferred compounds are chosen from (di)tert-butyl phenols, methyl-tert-butylphenols and di-methyl-tert-butylphenols, their mixtures, and their two-by-two condensation products, such as in particular 2,6-di-t-butyl-4-methyl phenol (BHT), 2,4-dimethyl-6-t-butyl phenol, 2,5-dimethyl-4-t-butyl phenol, 2,6 and 2,4 di-t-butyl phenol, 2,4,6-tri-t-butyl phenol, their mixtures, and their two-by-two condensation products.
  • BHT 2,6-di-t-butyl-4-methyl phenol
  • BHT 2,4-dimethyl-6-t-butyl phenol
  • 2,5-dimethyl-4-t-butyl phenol 2,6 and 2,4 di-t-butyl phenol
  • 2,4,6-tri-t-butyl phenol 2,4,6-tri-t-buty
  • the alkylphenol-aldehyde condensation resin can be chosen from any resin of this type already known and in particular those described in the documents EP857776 , EP1584673 .
  • modified alkylphenol-aldehyde resins according to the invention are advantageously obtained from at least one alkylphenol substituted in the para position.
  • Nonylphenol is preferably used.
  • the average number of phenolic nuclei per molecule of nonylphenol-aldehyde resin is advantageously within the range ranging from 6 to 25, preferably from 8 to 17, and more preferably from 9 to 16.
  • the number of phenolic nuclei can be determined by nuclear magnetic resonance (NMR) or gel permeation chromatography (GPC).
  • the modified alkylphenol-aldehyde resins are obtained by using the same aldehyde or the same ketone in both stages of its preparation.
  • the modified alkylphenol-aldehyde resins may be obtained from at least one aldehyde and/or ketone selected from formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, 2-ethyl-hexanal, benzaldehyde and/or acetone.
  • the modified alkylphenol-aldehyde resin is obtained from at least one aldehyde, preferably at least formaldehyde (or methanal).
  • the modified alkylphenol-aldehyde resins are capable of being obtained from p-nonylphenol, formaldehyde and at least one hydrocarbon compound comprising at least one alkylpolyamine group.
  • Said hydrocarbon compound may be an alkylpolyamine having at least two primary and/or secondary amine groups.
  • the alkylpolyamine is advantageously chosen from primary or secondary polyamines substituted by, respectively, one or two alkyl groups preferably comprising from 12 to 24 carbon atoms, more preferably from 12 to 22 carbon atoms.
  • the modified alkylphenol-aldehyde resin is obtained from at least one alkylpolyamine having at least two primary amine groups, preferably three primary amine groups.
  • the modified alkylphenol-aldehyde resin can advantageously be obtained from at least one alkylpolyamine in which all the amine groups are primary amines.
  • the modified alkylphenol-aldehyde resin is obtained from at least one alkylpolyamine comprising at least a fatty chain having from 12 to 24 carbon atoms, preferably from 12 to 22 carbon atoms.
  • a particularly preferred alkylpolyamine is tallow dipropylenetriamine.
  • alkylpolyamines are generally not pure compounds but mixtures. Suitable commercially available alkylpolyamines include fatty chain alkylpolyamines marketed under the names Trinoram ® , Duomeen ® , Dinoram ® , Triameen ® , Armeen ® , Polyram ® , Lilamin ® and Cemulcat ® .
  • Trinoram ® S which is a tallow dipropylenetriamine, also known as N-(Tallowalkyl)dipropylenetriamine ( CAS 61791-57-9 ).
  • the additive composition comprises one or more compounds (i)a) comprising one or two phenolic nuclei substituted by one or more alkyl groups chosen from methyl and t-butyl groups, and one or more modified alkylphenol-aldehyde resins (i)b).
  • the invention uses as additives (ii) one or more cetane index improving additives, also known as procetane additives or cetane booster additives.
  • the additive(s) (ii) are chosen from alkyl nitrates and aryl or alkyl peroxides.
  • Aryl peroxides include benzyl peroxide.
  • Alkyl peroxides include tert-butyl peroxide.
  • the additive(s) (ii) are preferably chosen from alkyl nitrates, and more preferably those of formula R-NO 3 with R a alkyl radical comprising from 2 to 12 carbon atoms, preferably from 4 to 8 carbon atoms.
  • a particularly preferred additive (ii) is ethyl hexyl nitrate.
  • the additive composition used in accordance with the present invention is characterized in that the mass ratio of the quantity of additive(s) (i) to the quantity of additive(s) (ii) is in the range from 1:3 to 3:1.
  • the mass ratio of the quantity of additive(s) (i) to the quantity of additive(s) (ii) is in the range from 1:2.5 to 2.5:1, preferably from 1:2 to 2:1 and more preferably from 1:1 to 1.5:1.
  • the additive composition used in accordance with the present invention comprises one or more detergency additive(s) (iii), also called deposit reducing additive(s), different from the compounds (i) having in their structure at least one alkyl-phenol group and the cetane number improving additives (ii) described above, and which may be chosen from the detergency additives for diesel fuels commonly used.
  • detergency additive(s) iii
  • deposit reducing additive(s) also called deposit reducing additive(s)
  • the latter are compounds well known to those skilled in the art.
  • the deposit-reducing additives may be chosen in particular (but not limited to) from the group consisting of amines, succinimides, alkenylsuccinimides, polyalkylamines, polyalkyl polyamines, polyetheramines, quaternary ammonium salts, and triazole derivatives, and more preferably from quaternary ammonium salts, and polyisobutylene mono- or polyamines (or PIB-amines), even more preferably from polyisobutylene succinimides (substituted or not by a triazole group), or quaternary ammonium salts and even better from polyisobutylene succinimides functionalized by a quaternary ammonium group, fatty acid amides functionalized by a quaternary ammonium group and their dimers such as the di-(alkylamido-propyl-quaternary ammonium) compounds described for example in the patent application European No.
  • fatty chain alkylamidoalkyl betaines and triazole derivatives.
  • Particularly preferred are polyisobutylene succinimides functionalized with a quaternary ammonium group and polyisobutylene succinimides functionalized with a triazole group.
  • Block copolymers formed from at least one polar unit and one apolar unit can also be used.
  • FR 1761700 on behalf of the Applicant.
  • the additive composition comprises at least one deposit-reducing additive consisting of a quaternary ammonium salt, obtained by reaction with a quaternization agent of a nitrogen compound comprising a tertiary amine function, this nitrogen compound being the product of the reaction of an acylating agent substituted by a hydrocarbon group and of a compound comprising at least one tertiary amine group and at least one group chosen from primary amines, secondary amines and alcohols.
  • a deposit-reducing additive consisting of a quaternary ammonium salt, obtained by reaction with a quaternization agent of a nitrogen compound comprising a tertiary amine function, this nitrogen compound being the product of the reaction of an acylating agent substituted by a hydrocarbon group and of a compound comprising at least one tertiary amine group and at least one group chosen from primary amines, secondary amines and alcohols.
  • said nitrogen compound is the reaction product of a succinic acid derivative substituted by a hydrocarbon group, preferably a polyisobutenyl succinic anhydride, and of an alcohol or of a primary or secondary amine also comprising a tertiary amine group.
  • a succinic acid derivative substituted by a hydrocarbon group preferably a polyisobutenyl succinic anhydride
  • an alcohol or of a primary or secondary amine also comprising a tertiary amine group.
  • the additive composition contains one or more deposit-reducing additive(s), preferably the ratio between the total weight content of compounds (i) having in their structure at least one alkyl-phenol group on the one hand and the total weight content of deposit-reducing additive(s) (iii) on the other hand ranges from 1:60 to 1:2, preferably from 1:20 to 1:3.
  • the total content of deposit reducing additive(s) (iii) in the fuel ranges from 5 to 5,000 ppm by weight, preferably from 10 to 1,000 ppm by weight, and more preferably from 20 to 500 ppm by weight, relative to the total weight of the fuel.
  • the additive composition may also comprise other additives, in addition to the compound(s) (i) having in their structure at least one alkyl-phenol group, the cetane index improving additives (ii) described above, and the deposit reducing additive(s) (iii) described above.
  • additives may be chosen, for example, in a non-limiting manner, from anti-corrosion additives, dispersant additives, demulsifying additives, anti-foaming agents, biocides, reodorants, friction modifiers, lubricity additives or smoothness additives, combustion aid agents (catalytic combustion and soot promoters), cold resistance additives and in particular agents improving the cloud point, the pour point, the TLF (“Filtrability Limit Temperature”), anti-sedimentation agents, anti-wear agents, tracers, solvents/carrier oils and conductivity modifying agents.
  • anti-corrosion additives dispersant additives, demulsifying additives, anti-foaming agents, biocides, reodorants, friction modifiers, lubricity additives or smoothness additives
  • combustion aid agents catalytic combustion and soot promoters
  • cold resistance additives and in particular agents improving the cloud point, the pour point, the TLF (“Filtrability Limit Temperature”), anti-sedi
  • additional additives may be present in an amount ranging from 5 to 1,000 ppm (each), preferably from 50 to 500 ppm by weight, relative to the total weight of the fuel.
  • the additive composition may advantageously comprise an organic solvent, which may for example be chosen from aromatic hydrocarbon solvents such as the solvent sold under the name “SOLVESSO”, alcohols, ethers and other oxygenated compounds, and paraffinic solvents such as hexane, pentane or isoparaffins, including hydrotreated vegetable oils known as HVO, alone or as a mixture.
  • aromatic hydrocarbon solvents such as the solvent sold under the name “SOLVESSO”
  • alcohols, ethers and other oxygenated compounds such as hexane, pentane or isoparaffins
  • hydrotreated vegetable oils known as HVO alone or as a mixture.
  • the additive composition comprises at least one solvent chosen from alcohols.
  • the additive composition contains at least one C1 to C8 monoalcohol, and preferably chosen from ethanol and ethyl-2-hexanol.
  • the use of the additive composition according to the invention applies to a fuel in liquid form at room temperature (20°C) and atmospheric pressure (1,013.10 5 Pa). This fuel is intended to power a Diesel engine.
  • Such a fuel typically comprises at least one liquid hydrocarbon cut from one or more sources selected from the group consisting of mineral sources, animal, vegetable and synthetic sources.
  • the fuel is advantageously chosen from hydrocarbon fuels and non-essentially hydrocarbon fuels, and mixtures thereof.
  • Hydrocarbon fuel means a fuel consisting of one or more compounds consisting solely of carbon and hydrogen.
  • a non-essentially hydrocarbon fuel is understood to mean a fuel consisting of one or more compounds consisting not essentially of carbon and hydrogen, i.e. which also contain other atoms, in particular oxygen atoms.
  • Hydrocarbon fuels include in particular middle distillates with boiling temperatures ranging from 100 to 500°C. These distillates may, for example, be chosen from distillates obtained by direct distillation of crude hydrocarbons, vacuum distillates, hydrotreated distillates, distillates resulting from catalytic cracking and/or hydrocracking of vacuum distillates, distillates resulting from ARDS (atmospheric residue desulfurization) and/or visbreaking conversion processes, distillates resulting from the recovery of Fischer Tropsch cuts, biodiesels such as distillates resulting from BTL (biomass to liquid) conversion of plant and/or animal biomass and vegetable oils. hydrotreated known to those skilled in the art under the name HVO (from the English “hydrotreated vegetable oil”) or HDRD (from the English “hydrogenation-derived renewable diesel”). Hydrocarbon fuels are typically diesel fuels (also called diesel fuels).
  • Diesel fuels include, in particular, all commercially available diesel engine fuel compositions. Examples include diesel fuels meeting the NF EN 590 standard.
  • Non-essentially hydrocarbon fuels include in particular vegetable and/or animal oils and/or esters of oils.
  • Mixtures of hydrocarbon fuel and non-primarily hydrocarbon fuel are typically type B x diesel fuels.
  • Diesel fuel type B x is defined as diesel fuel containing x% (v/v) of esters of vegetable or animal oils (including used cooking oils) converted by a chemical process called transesterification, obtained by reacting this oil with an alcohol to obtain fatty acid esters (FAEs). With methanol and ethanol, fatty acid methyl esters (FAMEs) and fatty acid ethyl esters (FAEs) are obtained, respectively.
  • FAMEs fatty acid methyl esters
  • FAMEs fatty acid methyl esters
  • FAEs fatty acid ethyl esters
  • the letter “B” is followed by a number x greater than zero and less than or equal to 100, which indicates the percentage of FAEs contained in the diesel fuel.
  • a B99 contains 99% EAG and 1% middle distillates of fossil origin (mineral source), B20, 20% EAG and 80% middle distillates of fossil origin etc....
  • B 0 type diesels which do not contain oxygenated compounds
  • Bx type diesels which contain x% (v/v) of vegetable oil or fatty acid esters, most often methyl esters (EMHV or EMAG), x designating a number ranging from 0 to 100.
  • EAG methyl esters
  • B 100 the fuel is designated by the term B 100 .
  • the fuel is chosen from diesel fuels, biodiesels, type B diesel fuels x containing x% (v/v) of vegetable or animal oil esters with x a number greater than zero and less than or equal to 100, hydrotreated vegetable oils (HVO), and their mixtures.
  • the fuel is chosen from type B diesels x containing x% (v/v) of vegetable or animal oil esters with x a number greater than zero and less than or equal to 100.
  • the vegetable oil esters are particularly chosen from fatty acid methyl esters (FAME) and fatty acid ethyl esters (FAE).
  • the additive composition according to the invention is used to reduce the emissions of nitrogen oxides as well as carbon monoxide and/or unburned hydrocarbons during the combustion of a liquid fuel in a compression-ignition internal combustion engine.
  • the use is also aimed at reducing particulate emissions.
  • the incorporation of the additive composition according to the invention into the liquid fuel produces an effect of reducing the emissions of nitrogen oxides as well as carbon monoxide and/or unburned hydrocarbons at the outlet of compression ignition engines powered by said fuel, compared to the same fuel not comprising the composition according to the invention.
  • the reducing effect is produced for the three types of emissions, namely nitrogen oxides, carbon monoxide and unburned hydrocarbons.
  • the reducing effect is also produced for particulate emissions.
  • the compression ignition engine or Diesel engine is a hybrid Diesel engine or a direct injection Diesel engine, preferably a direct injection Diesel engine and in particular a Diesel engine with a Common-Rail injection system (CRDI in English "Common Rail Direct Injection”).
  • the compression ignition engine or diesel engine is a marine engine.
  • This regulation defines a harmonized test procedure for vehicle approval in Europe and the measurement of different types of emissions.
  • This regulation is defined with reference to a standardized test called WLTP (World Harmonized Light Duty Test Procedure), which is a globally harmonized test procedure.
  • WLTP World Harmonized Light Duty Test Procedure
  • This test involves measuring the emissions of a standardized vehicle (Euro 6) during a defined test cycle called WLTC (World Harmonized Light Duty Test Cycle), using high-precision emissions analyzers.
  • the use according to the invention is compatible with existing exhaust gas post-treatment devices, and makes it possible to further reduce the levels of pollutants emitted by vehicles equipped with such devices and/or to extend the service life of this equipment and/or to space out maintenance operations on this equipment.
  • the compression ignition engine is equipped with one or more exhaust gas post-treatment devices, preferably chosen from selective catalytic reduction devices known as SCR, exhaust gas recirculation devices known as EGR, particulate filter type devices commonly called FAP, and devices known as SCRoF (SCR on Filter) or SCRF or SDPF which combine, within the same device, the functions of selective catalytic reduction and particle filtration.
  • SCR selective catalytic reduction devices
  • EGR exhaust gas recirculation devices
  • FAP particulate filter type devices
  • SCRoF SCR on Filter
  • SCRF SDPF
  • the process or method for reducing emissions of nitrogen oxides and at least one type of polluting agent chosen from carbon monoxide and unburned hydrocarbons during the combustion of a liquid fuel in a compression-ignition internal combustion engine consists of adding to said fuel composition an additive composition as described above.
  • the method is a method for reducing emissions of nitrogen oxides, carbon monoxide and unburned hydrocarbons. According to a particularly preferred embodiment, it further reduces emissions of solid particles.
  • the additives constituting the additive composition may be incorporated into the liquid fuel within a refinery and/or be incorporated downstream of the refinery, either separately or as a mixture, and in this case possibly in dispersion in an organic solvent, in particular in the form of an additive package.
  • This virgin fuel is called G0.
  • a second fuel composition G2 was prepared by adding to fuel composition G1 a mixture of alkyl phenol type compounds (consisting of 15% by mass of 2,6-di-t-butyl-4-methyl phenol, and 85% by mass of the condensation product of 2,4-dimethyl-6-t-butyl phenol and 2,5-dimethyl-4-t-butyl phenol) at a content of 350 ppm by mass in fuel G2.
  • the WLTP protocol driving cycle consists of driving the vehicle on a rolling test bench over a defined profile of 23 kilometres over a period of 1800 seconds (30 minutes) with an initial cold start.
  • the driving profile alternates between variable driving speeds over four main phases, separated by stops (zero speed).
  • the three tests differ only in the nature of the fuel supplying the engine (G0, G1 and G2 respectively).
  • the composition G2 makes it possible to reduce emissions by 95% compared to the comparative diesel G1 and by 88% compared to the virgin reference diesel G0.

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  • General Chemical & Material Sciences (AREA)
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Claims (17)

  1. Verwendung einer Additivzusammensetzung zur Reduzierung der Emissionen von Stickoxiden und mindestens eines aus Kohlenmonoxid und unverbrannten Kohlenwasserstoffen ausgewählten Schadstofftyps bei der Verbrennung eines flüssigen Kraftstoffs in einem Verbrennungsmotor mit Selbstzündung, die Folgendes umfasst:
    (i) ein oder mehrere Additive, die aus Verbindungen ausgewählt sind, die in ihrer Struktur mindestens eine Alkylphenolgruppe aufweisen;
    (ii) ein oder mehrere die Cetanzahl verbessernde Additive, die aus Alkylnitraten, Arylperoxiden und Alkylperoxiden ausgewählt sind; und
    (iii) ein oder mehrere Ablagerungen reduzierende Additive, die von den Verbindungen (i) und (ii) verschieden sind;
    wobei das Gewichtsverhältnis der Menge des Additivs (der Additive) (i) zur Menge des Additivs (der Additive) (ii) im Bereich von 1:3 bis 3:1 liegt.
  2. Verwendung nach dem vorhergehenden Anspruch, dadurch gekennzeichnet, dass das oder die Additive (i) aus den Verbindungen (i)a) ausgewählt sind, die einen oder zwei Phenolringe umfassen, die durch eine oder mehrere Alkylgruppen substituiert sind, die ausgewählt sind aus Methyl- und t-Butylgruppen und vorzugsweise aus Methyl-t-butylphenolen, Dimethyl-t-butylphenolen, Ethylt-butylphenolen, t-Butylphenolen, Di-t-butylphenolen, Tri-t-butylphenolen, Di-t-butyldimethylphenolen und deren Mischungen.
  3. Verwendung nach dem vorhergehenden Anspruch, dadurch gekennzeichnet, dass die Verbindung(en) (i)a) ausgewählt sind aus (Di)tert-Butylphenolen, Methyl-tert-butylphenolen und Dimethyl-tert-butylphenolen, deren Mischungen und deren Produkten einer paarweisen Kondensation, wie insbesondere 2,6-Di-t-butyl-4-methylphenol (BHT), 2,4-Dimethyl-6-t-butylphenol, 2,5-Dimethyl-4-t-butylphenol, 2,6- und 2,4-Di-t-butylphenol, 2,4,6-Tri-t-butylphenol, deren Mischungen und deren Produkten einer paarweisen Kondensation.
  4. Verwendung nach Anspruch 1, dadurch gekennzeichnet, dass das oder die Additive (i) aus modifizierten Alkylphenol-Aldehyd-Harzen (i)b) ausgewählt sind, die durch eine Mannich-Reaktion eines Alkylphenol-Aldehyd-Kondensationsharzes:
    • mit mindestens einem Aldehyd und/oder einem Keton mit 1 bis 8 Kohlenstoffatomen, vorzugsweise 1 bis 4 Kohlenstoffatomen;
    • und mindestens einer Kohlenwasserstoffverbindung mit mindestens einer Alkylpolyamin-Gruppe, die zwischen 1 und 30 Kohlenstoffatome, vorzugsweise zwischen 4 und 30 Kohlenstoffatome, aufweist,
    erhältlich sind, wobei das Alkylphenol-Aldehyd-Kondensationsharz selbst durch eine Kondensation:
    • mindestens eines Alkylphenols, das durch mindestens eine geradkettige oder verzweigte Alkylgruppe mit 1 bis 30 Kohlenstoffatomen substituiert ist, vorzugsweise einem Monoalkylphenol,
    • mit mindestens einem Aldehyd und/oder einem Keton mit 1 bis 8 Kohlenstoffatomen, vorzugsweise 1 bis 4 Kohlenstoffatomen,
    erhältlich ist.
  5. Verwendung nach dem vorhergehenden Anspruch, dadurch gekennzeichnet, dass die modifizierten Alkylphenol-Aldehyd-Harze aus p-Nonylphenol, Formaldehyd und mindestens einer Kohlenwasserstoffverbindung erhältlich sind, die mindestens eine Alkylpolyamin-Gruppe umfasst.
  6. Verwendung nach einem der Ansprüche 4 und 5, dadurch gekennzeichnet, dass die modifizierten Alkylphenol-Aldehyd-Harze aus mindestens einem Alkylpolyamin mit mindestens zwei primären Amingruppen und mindestens einer Fettkette mit 12 bis 24 Kohlenstoffatomen, vorzugsweise 12 bis 22 Kohlenstoffatomen, erhältlich sind.
  7. Verwendung nach einem der vorhergehenden Ansprüche, dadurch gekennzeichnet, dass die Additivzusammensetzung eine oder mehrere Verbindungen (i)a), die einen oder zwei Phenolringe umfassen, die durch eine oder mehrere Alkylgruppen substituiert sind, die ausgewählt sind aus Methyl- und t-Butylgruppen, und ein oder mehrere modifizierte Alkylphenol-Aldehyd-Harze (i)b) umfasst.
  8. Verwendung nach einem der vorhergehenden Ansprüche, dadurch gekennzeichnet, dass das oder die Additive (ii) aus Alkylnitraten der Formel R-NO3 ausgewählt sind, wobei R ein Alkylrest ist, der 2 bis 12 Kohlenstoffatome, stärker bevorzugt 4 bis 8 Kohlenstoffatome, umfasst, und das Additiv (ii) noch stärker bevorzugt Ethylhexylnitrat ist.
  9. Verwendung nach einem der vorhergehenden Ansprüche, dadurch gekennzeichnet, dass das Gewichtsverhältnis der Menge des Additivs (der Additive) (i) zur Menge des Additivs (der Additive) (ii) im Bereich von 1:2,5 bis 2,5:1, vorzugsweise von 1:2 bis 2:1 und stärker bevorzugt von 1:1 bis 1,5:1, liegt.
  10. Verwendung nach einem der vorhergehenden Ansprüche, dadurch gekennzeichnet, dass das oder die Ablagerungen reduzierenden Additive aus der Gruppe bestehend aus Aminen, Succinimiden, Alkenylsuccinimiden, Polyalkylaminen, Polyalkylpolyaminen, Polyetheraminen, quaternären Ammoniumsalzen und Triazolderivaten; stärker bevorzugt aus durch eine quaternäre Ammoniumgruppe funktionalisierten Polyisobutylensuccinimiden, durch eine quaternäre Ammoniumgruppe funktionalisierten Fettsäureamiden und deren Dimeren, wie Di(quaternäresalkylamidopropylammonium)-Verbindungen, Alkylamidoalkylbetainen mit einer Fettkette und Triazolderivaten; und noch stärker bevorzugt aus durch eine quaternäre Ammoniumgruppe funktionalisierten Polyisobutylensuccinimiden und durch eine Triazolgruppe funktionalisierten Polyisobutylensuccinimiden ausgewählt sind.
  11. Verwendung nach dem vorhergehenden Anspruch, dadurch gekennzeichnet, dass das Verhältnis zwischen einerseits dem Gesamtgewichtsgehalt an den Verbindungen (i), die in ihrer Struktur mindestens eine Alkylphenolgruppe aufweisen, und andererseits dem Gesamtgewichtsgehalt an (einem) Ablagerungen reduzierenden Additiv(en) von 1:60 bis 1:2, vorzugsweise von 1:20 bis 1:3, beträgt.
  12. Verwendung nach einem der vorhergehenden Ansprüche, dadurch gekennzeichnet, dass der Kraftstoff aus Dieselkraftstoffen, Biodieseln, Dieselkraftstoffen vom Bx-Typ, die x Vol.-% Ester von pflanzlichen oder tierischen Ölen enthalten, wobei x eine Zahl größer Null und kleiner oder gleich 100 ist, hydrierten Pflanzenölen (HVO) und Mischungen davon und vorzugsweise aus Dieselkraftstoffen vom Bx-Typ, die x Vol.-% Ester von pflanzlichen oder tierischen Ölen enthalten, wobei x eine Zahl größer Null und kleiner oder gleich 100 ist, ausgewählt ist, wobei die Ester von pflanzlichen Ölen vorzugsweise aus Fettsäuremethylestern und Fettsäureethylestern ausgewählt sind.
  13. Verwendung nach einem der vorhergehenden Ansprüche zur gleichzeitigen Reduzierung von Stickoxid-, Kohlenmonoxid- und unverbrannten Kohlenwasserstoff-Emissionen.
  14. Verwendung nach einem der vorhergehenden Ansprüche, um außerdem feste Partikelemissionen zu reduzieren.
  15. Verwendung nach einem der vorhergehenden Ansprüche, dadurch gekennzeichnet, dass es sich bei dem Verbrennungsmotor mit Selbstzündung um einen Hybrid-Dieselmotor oder einen Dieselmotor mit Direkteinspritzung, vorzugsweise einen Dieselmotor mit Direkteinspritzung und noch stärker bevorzugt um einen Dieselmotor mit Common-Rail-Einspritzsystem, handelt.
  16. Verwendung nach einem der Ansprüche 1 bis 14, dadurch gekennzeichnet, dass es sich bei dem Verbrennungsmotor mit Selbstzündung um einen Schiffsmotor handelt.
  17. Verfahren zur Reduzierung von Emissionen von Stickoxiden und mindestens eines aus Kohlenmonoxid und unverbrannten Kohlenwasserstoffen ausgewählten Schadstofftyps bei der Verbrennung eines flüssigen Kraftstoffs in einem Verbrennungsmotor mit Selbstzündung, das die Zugabe einer Additivzusammensetzung gemäß der Definition in einem der Ansprüche 1 bis 11 zu dem Kraftstoff umfasst.
EP22754467.3A 2021-07-19 2022-07-12 Verwendung einer additivzusammensetzung zur reduktion der emissionen von dieselfahrzeugen Active EP4373903B1 (de)

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