EP3824050A1 - Novel sugar amide fuel additives - Google Patents
Novel sugar amide fuel additivesInfo
- Publication number
- EP3824050A1 EP3824050A1 EP19758430.3A EP19758430A EP3824050A1 EP 3824050 A1 EP3824050 A1 EP 3824050A1 EP 19758430 A EP19758430 A EP 19758430A EP 3824050 A1 EP3824050 A1 EP 3824050A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- formula
- group
- additives
- fuel
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/224—Amides; Imides carboxylic acid amides, imides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- 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
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/06—Use of additives to fuels or fires for particular purposes for facilitating soot removal
-
- 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
- C10L10/18—Use of additives to fuels or fires for particular purposes use of detergents or dispersants for purposes not provided for in groups C10L10/02 - C10L10/16
-
- 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
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- 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
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
- C10L2230/22—Function and purpose of a components of a fuel or the composition as a whole for improving fuel economy or fuel efficiency
-
- 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
-
- 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
- C10L2270/026—Specifically adapted fuels for internal combustion engines for diesel engines, e.g. automobiles, stationary, marine
Definitions
- the present invention relates to new additives for liquid fuel of an internal combustion engine.
- the present invention relates more specifically to the use of particular compounds of the sugar-amide type for improving the detergency properties of liquid fuel compositions intended to supply internal combustion engines.
- the present invention also relates to additive compositions (or "additive packages") containing these particular compounds, as well as fuel compositions additivated with such compounds.
- Liquid fuels for internal combustion engines contain components that can degrade during engine operation.
- the problem of deposits in the internal parts of combustion engines is well known to engine manufacturers. It has been shown that the formation of these deposits has consequences on engine performance and in particular has a negative impact on consumption and particle emissions. Advances in fuel additive technology have made it possible to deal with this problem.
- So-called detergent additives used in fuels have already been proposed to keep the engine clean by limiting deposits ("keep-clean” effect) or by reducing the deposits already present in the internal parts of the combustion engine (“effect”). clean-up ”.
- mention may be made of document US4171959 which describes a detergent additive for petrol fuel containing a quaternary ammonium function.
- Document WO2006135881 describes a detergent additive containing a quaternary ammonium salt used to reduce or clean the deposits, in particular on the intake valves.
- the technology engines are constantly evolving and fuel requirements must evolve to meet these technological advances in combustion engines.
- the new petrol or diesel direct injection systems expose the injectors to more severe pressure and temperature conditions, which favors the formation of deposits.
- these new injection systems have more complex geometries to optimize spraying, in particular, more numerous holes having smaller diameters but which, on the other hand, induce a greater sensitivity to deposits.
- the presence of deposits can affect combustion performance, in particular increasing polluting emissions and particulate emissions. Other consequences of the excessive presence of deposits have been reported in the literature, such as an increase in fuel consumption and handling problems.
- the compounds according to the invention make it possible to maintain the cleanliness of the engine, in particular, by limiting or avoiding the formation of deposits (“keep-clean” effect by English) or by reducing the deposits already present in the internal parts of the combustion engine (“clean-up” effect in English).
- the subject of the present invention is therefore a fuel composition
- a fuel composition comprising:
- n represents an integer ranging from 2 to 6
- R represents a branched non-cyclic hydrocarbon group containing at least 10 carbon atoms.
- the fuel composition according to the invention comprises the compound (s) of formula (I) in a minimum content of 5 ppm.
- the hydrocarbon fraction (1) is chosen from hydrocarbon fuels, non-essentially hydrocarbon fuels and their mixtures.
- the hydrocarbon fuel is chosen from gasoline and diesel, also called diesel fuel.
- the subject of the invention is also a composition of additives comprising such a compound of formula (I) in combination with at least one fuel additive other than this, as well as a concentrate of additives containing such a composition.
- the invention also relates to the use of a compound of formula (I) as an additive, preferably as a detergent additive, in liquid fuel for internal combustion engines.
- said compound is used in liquid fuel to maintain cleanliness and / or clean at least one of the internal parts of said internal combustion engine.
- said compound is used in liquid fuel to limit or avoid the formation of deposits in at least one of the internal parts of said engine and / or reduce the deposits existing in at least one of the internal parts of said engine.
- the deposits are located in at least one of the internal parts chosen from the engine intake system, the combustion chamber and the fuel injection system.
- the compound of formula (I) is used to avoid and / or reduce the formation of deposits linked to the coking phenomenon and / or deposits of the soap and / or varnish type.
- the compound according to the invention also makes it possible to reduce the fuel consumption of the internal combustion engine.
- the internal combustion engine is a spark-ignition engine.
- the internal combustion engine is a diesel engine, preferably a diesel engine with direct injection.
- the compound of formula (I) is used to avoid and / or reduce the formation of deposits in the injection system of the diesel engine.
- the invention also relates to a method of maintaining the cleanliness and / or cleaning of at least one of the internal parts of an internal combustion engine comprising at least the following steps:
- the invention finally relates to a compound of formula (IA) specific, particularly suitable for the implementation of the invention.
- CN compound or group denotes a compound or group containing in its chemical structure N carbon atoms.
- the invention uses one or more compound (s) of formula (I) below:
- n represents an integer ranging from 2 to 6
- R represents a branched non-cyclic hydrocarbon group containing at least 10 carbon atoms.
- n denotes 3 or 4, and more preferably n denotes 4.
- the hydrocarbon group R is branched, and not cyclic, that is to say that it does not contain a ring. It can be saturated or unsaturated, and contain or not contain one or more heteroatoms such as in particular oxygen and nitrogen atoms.
- the group R is aliphatic.
- the group R contains from 10 to 400 carbon atoms. More preferably, the group R contains from 20 to 300 carbon atoms, more preferably from 50 to 300 carbon atoms, even more preferably from 100 to 200 carbon atoms.
- the group R is a branched alkyl group, which can be optionally substituted by one or more oxygen and / or nitrogen groups.
- the group R is a branched C 10 -C 4 alkyl group, preferably C 20 to C 300, preferably C 50 to C 300, even more preferably C 1 00 to C 200, and more preferably still chosen from polyisobutylene groups.
- R is an amino group, and preferably a polyamine group, that is to say that it contains at least two nitrogen atoms.
- R more preferably represents a group of formula (B) below:
- R 1 represents a divalent hydrocarbon chain having from 1 to 4 carbon atoms
- R 2 represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms
- R 3 and R 4 independently represent one of the other, a hydrocarbon group having at least 8 carbon atoms
- p represents an integer ranging from 1 to 5.
- Ri represents a group - (C H2 -) k with k being
- R2 represents a hydrogen atom
- R3 and R 4 represent, independently of one another, a hydrocarbon group having 12 to 24 carbon atoms and p is 2 or 3, preferably 2.
- R represents a group of formula (A):
- n represents an integer ranging from 2 to 6
- R ’and R which may be identical or different, represent a hydrogen atom or a hydrocarbon group, at least one of the groups R ’and R” comprising at least 10 carbon atoms.
- n denotes 3 or 4, and more preferably m denotes 4.
- R 'and R " denote a hydrogen atom or a hydrocarbon group which may be linear or branched, cyclic or non-cyclic, saturated or unsaturated, aromatic or aliphatic, and may or may not contain one or more heteroatoms such as in particular oxygen and nitrogen atoms.
- At least one of the groups R ’and R" contains from 10 to 400 carbon atoms, more preferably from 50 to 300 carbon atoms, and even more preferably from 100 to 200 carbon atoms.
- At least one of the groups R ′ and R ′′ is a branched alkyl group, which can be optionally substituted by one or more oxygen and / or nitrogen groups.
- at least one of the groups R ′ and R ′′ is a branched C 10 -C 4 alkyl group, preferably C 20 to C 300, more preferably C 50 to C 300, more preferably still from C 1 00 to C 200, and more preferably still a polyisobutylene group.
- n represents an integer ranging from 2 to 6, preferably n denotes 3 or 4, and more preferably n denotes 4;
- n represents an integer ranging from 2 to 6, preferably m denotes 3 or 4, and more preferably m denotes 4;
- R ’and R which may be identical or different, represent a hydrogen atom or a hydrocarbon group, at least one of the groups R ’and R” comprising at least 10 carbon atoms.
- the hydrocarbon groups R ’and / or R" may be linear or branched, cyclic or non-cyclic, saturated or unsaturated, aromatic or aliphatic, and may or may not contain one or more heteroatoms such as in particular oxygen and nitrogen atoms.
- At least one of the groups R ′ and R ′′ contains from 10 to 400 carbon atoms, more preferably from 20 to 300 carbon atoms, more preferably from 50 to 300 carbon atoms. carbon, and more preferably still from 100 to 200 carbon atoms.
- At least one of the groups R ′ and R " is a branched alkyl group, which can be optionally substituted by one or more oxygen and / or nitrogen groups.
- At least one of the groups R ′ and R ′′ is a branched C 10 -C 4 alkyl group, preferably C 20 to C 300, more preferably C 50 to C 300, more preferably still from C 1 00 to C 200, more preferably still chosen from polyisobutylene groups.
- the compounds of formula (I) can be prepared by condensation of an amine substituted with at least one hydrocarbon-based group R containing at least 10 carbon atoms on a lactone carrying at least two hydroxyl functions.
- the compounds of formula (IA) can be prepared by condensation of a diamine containing groups R ’and R” as defined above on a lactone carrying at least two hydroxyl functions.
- the compounds of formula (I) described above are very particularly useful as additives for liquid fuels of an internal combustion engine.
- detergent additive for liquid fuel is understood to mean an additive which is incorporated in small quantity into the liquid fuel and has an effect on the cleanliness of said engine compared to said non-specially additive liquid fuel.
- the fuel composition is as described below and advantageously comprises at least one cut of hydrocarbons originating from one or more sources chosen from the group consisting of mineral sources, preferably petroleum, animal, vegetable and synthetic.
- the use of the compounds according to the invention in a liquid fuel makes it possible to maintain the cleanliness of at least one of the internal parts of the internal combustion engine and / or to clean at least one of the internal parts of the internal combustion engine .
- the use of said compound as an additive in liquid fuel makes it possible to observe both the effects, limitation (or prevention) and reduction of deposits (“keep-clean” and “clean-up” effects).
- the internal combustion engine is a spark-ignition engine, preferably with direct injection (DISI in English "Direct Injection Spark Ignition engine”).
- the targeted deposits are located in at least one of the internal parts of said positive-ignition engine.
- the internal part of the spark-ignition engine kept clean (keep-clean) and / or cleaned (clean-up) is advantageously chosen from the engine's intake system, in particular the intake valves (IVD in English).
- Intake Valve Deposit ”), the combustion chamber (CCD in English“ Combustion Chamber Deposit ”or TCD in English“ Total Chamber Deposit ”) and the fuel injection system, in particular the injectors of an injection system indirect (PFI in English "Port Fuel Injector") or the injectors of a direct injection system (DISI).
- PFI in English "Port Fuel Injector”
- DISI direct injection system
- the internal combustion engine is a diesel engine, preferably a direct injection diesel engine, in particular a diesel engine with common rail injection system (CRDI in English "Common Rail Direct Injection”) .
- the targeted deposits are located in at least one of the internal parts of said diesel engine.
- the targeted deposits are located in the injection system of the diesel engine, preferably located on an external part of an injector of said injection system, for example the nose of the injector and / or on an internal part.
- an injector of said injection system IDID in English "Internal Diesel Injector Deposits"
- an injector of said injection system for example on the surface of an injector needle.
- the deposits may consist of deposits linked to the phenomenon of coking (“coking” in English) and / or deposits of the soap and / or varnish type (in English “lacquering”).
- the compound (s) of formula (I) as described above can advantageously be used as additives in liquid fuel to reduce and / or avoid the loss of power due to the formation of deposits in the internal parts of an engine Diesel with direct injection, said loss of power being able to be determined according to the standard engine test method CEC F-98-08.
- Said compound (s) of formula (I) can advantageously be used in liquid fuel to reduce and / or avoid restriction of the flow of fuel emitted by the injector of a direct injection diesel engine during its operation, said flow restriction being able to be determined according to the standard engine test method CEC F-23-1-01.
- the use of said compound as a fuel additive makes it possible, compared to liquid fuel not specially additive, to limit or avoid the formation of deposits on at least one type of deposits described above and / or reduce the deposits existing on at least one type deposits previously described.
- the use of said compound of formula (I) as a fuel additive also makes it possible to reduce the fuel consumption of the internal combustion engine.
- the use of said compound of formula (I) as a fuel additive also makes it possible to reduce the emissions of pollutants, in particular, the emissions of particles from the internal combustion engine.
- the use of said compound as a fuel additive makes it possible to reduce both fuel consumption and pollutant emissions.
- the compound (s) of formula (I) as described above can be used alone or as a mixture with other additives, in particular in the form of an additive composition or a concentrate of additives as described below, also called according to usage "additive package”.
- Said compounds of formula (I) can be added to the liquid fuel within a refinery and / or be incorporated downstream from the refinery and / or possibly mixed with other additives in the form of an additive package.
- the compound (s) of formula (I) are advantageously used in fuel at a total content of at least 5 ppm by weight, relative to the total weight of the fuel composition.
- the content of said compound ranges from 5 to 10,000 ppm by weight, preferably from 10 to 1000 ppm by weight, and better still from 25 to 500 ppm by weight, relative to the total weight of the fuel composition.
- composition of additives is a composition of additives:
- the invention also relates to an additive composition
- an additive composition comprising a compound of formula (I) as described above, and one or more additive (s) different from said compounds of formula (I).
- additives different from the compounds of formula (I) can for example be chosen, without limitation, from detergent additives, anti-corrosion agents, dispersants, demulsifiers, anti-foaming agents, biocides, reodorants, procetane additives, friction modifiers, lubricant additives or oiliness additives, combustion aid agents (catalytic combustion and soot promoters), cold-keeping additives and in particular improving agents cloud point, pour point, TLF (“Filterability limit temperature”), anti-sedimentation agents, anti-wear agents and conductivity modifiers.
- detergent additives for example be chosen, without limitation, from detergent additives, anti-corrosion agents, dispersants, demulsifiers, anti-foaming agents, biocides, reodorants, procetane additives, friction modifiers, lubricant additives or oiliness additives, combustion aid agents (catalytic combustion and soot promoters), cold-keeping additives and in particular improving agents cloud point, pour point, TLF (“Filter
- procetane additives in particular (but not limited to) chosen from alkyl nitrates, preferably 2-ethyl hexyl nitrate, aryl peroxides, preferably benzyl peroxide, and alkyl peroxides, preferably ter-butyl peroxide;
- anti-foam additives in particular (but not limited to) chosen from polysiloxanes, oxyalkylated polysiloxanes, and fatty acid amides derived from vegetable oils or animal. Examples of such additives are given in EP861882, EP663000, EP736590;
- CFI Cold fluidizing additives
- EVA ethylene / vinyl acetate
- TEU ethylene / vinyl propionate
- EVE ethylene / vinyl ethanoate
- EMMA ethylene / methyl methacrylate
- alkyl fumarate described, for example, in US3048479, US3627838, US3790359, US3961961 and EP261957;
- cloud point additives in particular (but not limited to) chosen from the group consisting of long chain olefin terpolymers / (meth) acrylic ester / maleimide, and polymers of fumaric / maleic acid esters. Examples of such additives are given in FR252805 1, FR252805 1, FR2528423, EP 1 12195, EP 172758, EP271385, EP291367;
- detergent additives in particular (but not limited to) chosen from the group consisting of succinimides, polyetheramines and quaternary ammonium salts; for example those described in documents US4171959 and WO2006135881;
- the polyfunctional additives for cold operability chosen from the group consisting of polymers based on olefin and alkenyl nitrate as described in EP573490.
- the additive composition can advantageously comprise from 0.1 to 80% by weight of compound (s) of formula (I), preferably from 1 to 50% by weight, and better still from 5 to 30% by weight , based on the total weight of the additive composition.
- the present invention also relates to a concentrate of additives comprising an additive composition as described above, in admixture with an organic liquid.
- the organic liquid is advantageously inert with respect to the constituents of the additive composition, and miscible with liquid fuels, in particular those from one or more sources chosen from the group consisting of mineral sources, preferably petroleum. , animal, plant and synthetic.
- the organic liquid is preferably 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, only or mixed.
- aromatic hydrocarbon solvents such as the solvent sold under the name "SOLVESSO”
- alcohols, ethers and other oxygenated compounds such as hexane, pentane or isoparaffins, only or mixed.
- paraffinic solvents such as hexane, pentane or isoparaffins
- the present invention also relates to a fuel composition
- a fuel composition comprising:
- petroleum will be chosen as the mineral source.
- the cut of liquid hydrocarbons is advantageously chosen from hydrocarbon fuels and non-essentially hydrocarbon fuels, alone or as a mixture.
- Hydrocarbon fuel is understood to mean a fuel consisting of one or more compounds consisting solely of carbon and hydrogen.
- Non-essentially hydrocarbon fuel is understood to mean a fuel made up of one or more compounds made up not essentially of carbon and hydrogen, that is to say which also contain other atoms, in particular oxygen atoms.
- Hydrocarbon fuels include in particular middle distillates with a boiling point ranging from 100 to 500 ° C or lighter distillates with a boiling temperature in the range of essences. These distillates can for example be chosen from distillates obtained by direct distillation of crude hydrocarbons, vacuum distillates, hydrotreated distillates, distillates from catalytic cracking and / or hydrocracking of vacuum distillates, distillates resulting from ARDS-type conversion processes (in English "atmospheric residue desulfurization") and / or visbreaking, the distillates from the recovery of Fischer Tropsch cuts. Hydrocarbon fuels are typically petrol and diesel (also called diesel fuel).
- the cut of liquid hydrocarbons is chosen from gasolines and diesel fuels.
- the gasolines include, in particular, all fuel compositions for spark ignition engines commercially available.
- gasolines meeting the NF EN 228 standard Gasolines generally have octane numbers high enough to avoid the knocking phenomenon.
- gasoline-type fuels sold in Europe, conforming to standard NF EN 228 have an engine octane number (MON in English “Motor Octane Number”) greater than 85 and a research octane number (RON in English “ Research Octane Number ”) with a minimum of 95.
- Gasoline fuels generally have an RON ranging from 90 to 100 and a MON ranging from 80 to 90, the RON and MON being measured according to ASTM D 2699- 86 or D 2700-86.
- Diesel oils include, in particular, all fuel compositions for diesel engines commercially available. Mention may be made, as a representative example, of diesel oils meeting the standard NF EN 590.
- Fuels that are not essentially hydrocarbon-based include in particular oxygenates, for example distillates resulting from the BTL (in English "biomass to liquid") conversion of plant and / or animal biomass, taken alone or in combination; the biofuels, for example oils and / or esters of vegetable and / or animal oils; biodiesels of animal and / or vegetable origin and bioethanols.
- the mixtures of hydrocarbon fuel and non-essentially hydrocarbon fuel are typically gas oils of type B x or gasolines of type E x .
- diesel fuel type B x means a diesel fuel, a diesel fuel which contains x% (v / v) of vegetable or animal oil esters (including used cooking oils) transformed by a chemical process called transesterification, obtained by reacting this oil with an alcohol in order to obtain fatty acid esters (EAG). With methanol and ethanol, methyl esters of fatty acids (EMAG) and ethyl esters of fatty acids (EEAG) are obtained, respectively.
- EMAG methyl esters of fatty acids
- EEAG ethyl esters of fatty acids
- the letter "B” followed by a number indicates the percentage of EAG contained in the diesel.
- a B99 contains 99% of EAG and 1% of middle distillates of fossil origin (mineral source), B20, 20% of EAG and 80% of middle distillates of fossil origin, etc.
- gas oils of type Bo which do not contain oxygenated compounds
- gas oils of type Bx which contain x% (v / v) of vegetable oil esters or fatty acids, most often methyl esters (EMHV or EMAG), x denoting a number ranging from 0 to 100.
- EAG methyl esters
- Bioo the fuel is designated by the term Bioo.
- type E x petrol for positive ignition engine is understood to mean a petrol fuel which contains x% (v / v) of oxygenates, generally ethanol, bioethanol and / or ethyl tertiary butyl ether (ETBE), x denoting a number ranging from 0 to 100.
- x% (v / v) of oxygenates generally ethanol, bioethanol and / or ethyl tertiary butyl ether (ETBE), x denoting a number ranging from 0 to 100.
- the sulfur content of the liquid hydrocarbon fraction is preferably less than or equal to 5000 ppm, preferably less than or equal to 500 ppm, and more preferably less than or equal to 50 ppm, or even even less than 10 ppm and advantageously sulfur free.
- the compound or compounds of formula (I) are preferably present in small quantity in the fuel composition according to the invention, in a content sufficient to produce a detergent effect.
- the fuel composition comprises the compound (s) of formula (I) in a minimum content of 5 ppm.
- the content of said compound ranges from 5 to 10,000 ppm by weight, preferably from 10 to 1000 ppm by weight, and better still from 25 to 500 ppm by weight, relative to the total weight of the fuel composition.
- the fuel composition can also comprise one or more additional additive (s), different from said compounds of formula (I).
- This or these additional additive (s) can for example be chosen, without limitation, from: detergent additives, anti-corrosion agents, dispersants, demulsifiers, anti-foaming agents, biocides, reodorants, procetane additives, friction modifiers, lubricant additives or oiliness additives, combustion aid agents (catalytic combustion and soot promoters), cold-resistance additives and in particular agents improving the point of cloudiness, pour point, TLF (“Filterability limit temperature”), anti-sedimentation agents, anti-wear agents and agents modifying conductivity.
- detergent additives anti-corrosion agents, dispersants, demulsifiers, anti-foaming agents, biocides, reodorants, procetane additives, friction modifiers, lubricant additives or oiliness additives
- combustion aid agents catalytic combustion and soot promoters
- This or these additional additives are more preferably chosen from:
- procetane additives in particular (but not limited to) chosen from alkyl nitrates, preferably 2-ethyl hexyl nitrate, aryl peroxides, preferably benzyl peroxide, and alkyl peroxides, preferably ter-butyl peroxide;
- anti-foam additives in particular (but not limited to) chosen from polysiloxanes, oxyalkylated polysiloxanes, and fatty acid amides derived from vegetable or animal oils. Examples of such additives are given in EP861882, EP663000, EP736590;
- Cold fluidizing additives chosen from ethylene and unsaturated ester copolymers, such as ethylene / vinyl acetate copolymers (EVA), ethylene / vinyl propionate (TEU), ethylene / vinyl ethanoate (EVE), ethylene / methyl methacrylate (EMMA), and ethylene / alkyl fumarate described, for example, in US3048479, US3627838, US3790359, US3961961 and EP261957;
- EVA ethylene / vinyl acetate copolymers
- EVE ethylene / vinyl propionate
- EMMA ethylene / vinyl ethanoate
- EMMA ethylene / alkyl fumarate
- cloud point additives in particular (but not limited to) chosen from the group consisting of long chain olefin / (meth) acrylic ester / maleimide terpolymers, and polymers of fumaric / maleic acid esters. Examples of such additives are given in FR252805 1, FR252805 1, FR2528423, EP 1 12195, EP 172758, EP271385, EP291367;
- detergent additives in particular (but not limited to) chosen from the group consisting of succinimides, polyetheramines and quaternary ammonium salts; for example those described in documents US4171959 and WO2006135881;
- the polyfunctional additives for cold operability selected from the group consisting of polymers based on olefin and alkenyl nitrate as described in EP573490.
- These additional additives can be present in an amount ranging from 10 to 1000 ppm (each), preferably from 50 to 500 ppm by weight in the fuel composition.
- the fuel composition according to the invention can be prepared according to any known process, by adding a cut of liquid hydrocarbons as described above with at least one compound of formula (I) as described above.
- the combustion of the fuel composition comprising the compound of formula (I) according to the invention in an internal combustion engine also makes it possible to reduce the fuel consumption and / or the pollutant emissions.
- a method of maintaining cleanliness (keep-clean) and / or cleaning (clean-up) of at least one of the internal parts of an internal combustion engine comprises the preparation of a fuel composition as described above and the combustion of said fuel composition in the internal combustion engine.
- the internal combustion engine is a spark-ignition engine, preferably with direct injection (DISI).
- DISI direct injection
- the internal part kept clean and / or cleaned of the positive-ignition engine is preferably chosen from the intake system of the engine, in particular the intake valves (IVD), the combustion chamber (CCD or TCD) and the fuel injection system, in particular the injectors of an indirect injection system (PFI) or the injectors of a direct injection system (DISI).
- the intake system of the engine in particular the intake valves (IVD), the combustion chamber (CCD or TCD) and the fuel injection system, in particular the injectors of an indirect injection system (PFI) or the injectors of a direct injection system (DISI).
- the internal combustion engine is a diesel engine, preferably a direct injection diesel engine, in particular a diesel engine with common-rail injection systems (CRDI).
- a direct injection diesel engine in particular a diesel engine with common-rail injection systems (CRDI).
- CCDI common-rail injection systems
- the internal part kept clean (keep-clean) and / or cleaned (clean-up) of the diesel engine is preferably the injection system of the diesel engine, preferably an external part of an injector. of said injection system, for example the nose of the injector and / or one of the internal parts of an injector of said injection system, for example the surface of an injector needle.
- the keep-clean and / or clean-up process preferably comprises the following successive steps:
- step 2) the incorporation into the fuel of the compound (s) of formula (I) selected (s) at the content determined in step 1) and, optionally, of the other fuel additives.
- the compound of formula (I) according to the invention and the other additives if necessary can be used in the form of a concentrate or of a concentrate of additives as described above.
- Step 1) is carried out according to any known process and is part of current practice in the field of fuel additivation. This step involves defining at least one characteristic representative of the detergency properties of the fuel composition.
- the characteristic characteristic of the detergency properties of the fuel will depend on the type of internal combustion engine, for example Diesel or by positive ignition, on the direct or indirect injection system and on the location in the engine of the deposits targeted for cleaning and / or maintaining cleanliness.
- the characteristic representative of the detergency properties of the fuel may, for example, correspond to the loss of power due to the formation of deposits in the injectors or the restriction of the flow of fuel emitted by the injector at during the operation of said engine.
- the characteristic characteristic of detergency properties can also correspond to the appearance of lacquering-type deposits at the level of the injector needle (IDID).
- the quantity of compound (s) of formula (I) according to the invention to be added to the fuel composition to reach the specification (step 1 described above) will typically be determined by comparison with the fuel composition but without the compound (s) of formula (I), the given specification relating to the detergency can for example be a target value of power loss according to the DW10 method or a flow restriction value according to the XUD9 method mentioned above above.
- the amount of compound (s) of formula (I) according to the invention can in particular vary according to the nature and the origin of the fuel, for example according to the rate of compounds with n-alkyl, iso-alkyl or n substituents -alkenyl.
- the nature and origin of the fuel can be a factor to take into account for step 1).
- the keep-clean and / or clean-up process may also include an additional step 3) after step 2), verification of the target reached and / or adjustment of the target. additive rate with the compound (s) of formula (I) according to the invention as detergent additive.
- the compounds of formula (I) according to the invention have remarkable properties as detergent additives in a liquid fuel, in particular in a diesel or petrol fuel. These compounds are particularly remarkable in particular because they are effective for a wide range of liquid fuels and / or for one or more types of engines and / or against one or more types of deposits which form in the internal parts of internal combustion engines.
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Combustion & Propulsion (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Solid Fuels And Fuel-Associated Substances (AREA)
- Liquid Carbonaceous Fuels (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1856545A FR3083799B1 (en) | 2018-07-16 | 2018-07-16 | FUEL ADDITIVES, SUGAR-AMID TYPE |
PCT/FR2019/051751 WO2020016508A1 (en) | 2018-07-16 | 2019-07-12 | Novel sugar amide fuel additives |
Publications (1)
Publication Number | Publication Date |
---|---|
EP3824050A1 true EP3824050A1 (en) | 2021-05-26 |
Family
ID=63638075
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP19758430.3A Withdrawn EP3824050A1 (en) | 2018-07-16 | 2019-07-12 | Novel sugar amide fuel additives |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP3824050A1 (en) |
FR (1) | FR3083799B1 (en) |
WO (1) | WO2020016508A1 (en) |
Family Cites Families (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3048479A (en) | 1959-08-03 | 1962-08-07 | Exxon Research Engineering Co | Ethylene-vinyl ester pour depressant for middle distillates |
US3627838A (en) | 1964-12-11 | 1971-12-14 | Exxon Research Engineering Co | Process for manufacturing potent pour depressants |
US3790359A (en) | 1969-03-17 | 1974-02-05 | Exxon Research Engineering Co | Middle distillate fuel having increased low temperature flowability |
US3779724A (en) * | 1970-04-29 | 1973-12-18 | Cities Service Oil Co | Nitrogen-containing carbohydrate derivatives and hydrocarbon fuel compositions containing same |
US3961961A (en) | 1972-11-20 | 1976-06-08 | Minnesota Mining And Manufacturing Company | Positive or negative developable photosensitive composition |
US4171959A (en) | 1977-12-14 | 1979-10-23 | Texaco Inc. | Fuel composition containing quaternary ammonium salts of succinimides |
FR2528051B1 (en) | 1982-06-08 | 1986-05-02 | Inst Francais Du Petrole | NITROGEN ADDITIVES FOR USE AS DISORDERS TO REDUCE THE POINT OF MEDIUM HYDROCARBON DISTILLATES AND COMPOSITIONS OF MEDIUM HYDROCARBON DISTILLATES CONTAINING THE ADDITIVES |
FR2528423B1 (en) | 1982-06-10 | 1987-07-24 | Inst Francais Du Petrole | NITROGEN ADDITIVES FOR USE AS DISORDERS TO REDUCE THE POINT OF MEDIUM HYDROCARBON DISTILLATES AND COMPOSITIONS OF MEDIUM HYDROCARBON DISTILLATES CONTAINING THE ADDITIVES |
FR2535723A1 (en) | 1982-11-09 | 1984-05-11 | Inst Francais Du Petrole | NITROGEN ADDITIVES FOR USE AS HYDROCARBON MOISTURE DISTILLATE DISORDER DISORDERS AND HYDROCARBON MEAL DISTILLATE COMPOSITIONS COMPRISING THE SAME |
FR2567536B1 (en) | 1984-07-10 | 1986-12-26 | Inst Francais Du Petrole | ADDITIVE COMPOSITIONS, IN PARTICULAR FOR IMPROVING THE COLD FILTRABILITY PROPERTIES OF MEDIUM OIL DISTILLATES |
IN184481B (en) | 1986-09-24 | 2000-08-26 | Exxon Chemical Patents Inc | |
FR2607139B1 (en) | 1986-11-21 | 1989-08-18 | Inst Francais Du Petrole | POLYMERS WITH NITROGEN FUNCTIONS DERIVED FROM UNSATURATED POLYESTERS AND THEIR USE AS ADDITIVES FOR LOWERING THE FLOW POINT OF MEDIUM HYDROCARBON DISTILLATES |
FR2613371B1 (en) | 1987-04-01 | 1989-07-07 | Inst Francais Du Petrole | NITROGENATED COPOLYMERS, THEIR PREPARATION AND THEIR USE AS ADDITIVES FOR IMPROVING THE FLOW PROPERTIES OF MEDIUM HYDROCARBON DISTILLATES |
GB9104138D0 (en) | 1991-02-27 | 1991-04-17 | Exxon Chemical Patents Inc | Polymeric additives |
GB9219962D0 (en) | 1992-09-22 | 1992-11-04 | Exxon Chemical Patents Inc | Additives for organic liquids |
GB9301119D0 (en) | 1993-01-21 | 1993-03-10 | Exxon Chemical Patents Inc | Fuel composition |
FR2751982B1 (en) | 1996-07-31 | 2000-03-03 | Elf Antar France | ONCTUOSITY ADDITIVE FOR ENGINE FUEL AND FUEL COMPOSITION |
JPH10237467A (en) | 1997-02-26 | 1998-09-08 | Tonen Corp | Fuel oil composition for diesel engine |
US5730029A (en) | 1997-02-26 | 1998-03-24 | The Lubrizol Corporation | Esters derived from vegetable oils used as additives for fuels |
FR2772783A1 (en) | 1997-12-24 | 1999-06-25 | Elf Antar France | New additives compositions for improving the lubricating power of low sulfur petrol, diesel and jet fuels |
FR2772784B1 (en) | 1997-12-24 | 2004-09-10 | Elf Antar France | ONCTUOSITY ADDITIVE FOR FUEL |
PL2998384T3 (en) | 2005-06-16 | 2019-02-28 | The Lubrizol Corporation | Diesel fuel composition comprising a quaternary ammonium salt detergent |
KR20100131991A (en) * | 2008-02-01 | 2010-12-16 | 바스프 에스이 | Specific polyisobuteneamines and their use as detergents in fuels |
US20100132253A1 (en) * | 2008-12-03 | 2010-06-03 | Taconic Energy, Inc. | Fuel additives and fuel compositions and methods for making and using the same |
GB201007756D0 (en) | 2010-05-10 | 2010-06-23 | Innospec Ltd | Composition, method and use |
FR2994695B1 (en) | 2012-08-22 | 2015-10-16 | Total Raffinage Marketing | ADDITIVES ENHANCING WEAR AND LACQUERING RESISTANCE OF GASOLINE OR BIOGAZOLE FUEL |
-
2018
- 2018-07-16 FR FR1856545A patent/FR3083799B1/en active Active
-
2019
- 2019-07-12 WO PCT/FR2019/051751 patent/WO2020016508A1/en unknown
- 2019-07-12 EP EP19758430.3A patent/EP3824050A1/en not_active Withdrawn
Also Published As
Publication number | Publication date |
---|---|
WO2020016508A1 (en) | 2020-01-23 |
FR3083799B1 (en) | 2021-03-05 |
FR3083799A1 (en) | 2020-01-17 |
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