EP2867348B1 - Compositions d'additifs et leur utilisation pour ameliorer les proprietes a froid de carburants et combustibles - Google Patents

Compositions d'additifs et leur utilisation pour ameliorer les proprietes a froid de carburants et combustibles Download PDF

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Publication number
EP2867348B1
EP2867348B1 EP13730207.1A EP13730207A EP2867348B1 EP 2867348 B1 EP2867348 B1 EP 2867348B1 EP 13730207 A EP13730207 A EP 13730207A EP 2867348 B1 EP2867348 B1 EP 2867348B1
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Prior art keywords
fuels
carbon atoms
resin
aldehyde
alkylphenol
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German (de)
English (en)
French (fr)
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EP2867348A1 (fr
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Géraldine PAPIN
Nelly Dolmazon
Frédéric Tort
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TotalEnergies Marketing Services SA
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Total Marketing Services SA
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    • C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
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    • C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
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    • C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
    • C10L1/1963—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof mono-carboxylic
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    • C10L1/14—Organic compounds
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    • C10L1/192—Macromolecular compounds
    • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/197—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid
    • C10L1/1973—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid mono-carboxylic
    • 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
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • 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
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    • 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
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
    • 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
    • C10L1/22—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
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    • C10L1/00—Liquid carbonaceous fuels
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    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
    • C10L1/2364—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amide and/or imide groups
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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
    • C10L1/234—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)
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    • 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
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    • C10L2250/00—Structural features of fuel components or fuel compositions, either in solid, liquid or gaseous state
    • C10L2250/04—Additive or component is a polymer

Definitions

  • the present invention relates to additive compositions and their use in liquid hydrocarbon fuels and fuels to improve their cold properties.
  • the present invention relates to additive compositions and their use as filterability additives for liquid hydrocarbon fuels and fuels.
  • Crude oils or crude oils and middle distillates obtained from crude oils of petroleum origin by distillation such as diesel, diesel fuel or heating oil, contain, depending on the source of these crude oils or crude oils, different quantities n-alkanes or n-paraffins which, by lowering the temperature, typically below 0 ° C, crystallize as crystals in the form of platelets which tend to agglomerate. There is a deterioration in the flow characteristics of oils and distillates. There are difficulties in transporting and / or storing the oil or fuel. Wax crystals have a tendency to clog and plug pipes, pipes, pumps and filters, for example in motor vehicle fuel systems.
  • the usual flow improvers for crude oils and middle distillates are copolymers and terpolymers of ethylene and vinyl ester (s) and / or acrylic ester (s), alone or in mixing with low molecular weight oil soluble compounds or polymers which contain one or more ester, amide, imide, ammonium groups substituted by at least one alkyl chain.
  • Another purpose of the flow enhancement additives is to ensure the dispersion of the paraffin crystals, so as to delay or prevent the sedimentation of the crystals of the crystals.
  • paraffins and thus the formation of a paraffin-rich layer in the bottom of containers, tanks or storage tanks.
  • WASA cronym for the term wax anti-settling additive
  • Alkylphenol-aldehyde resins derived from the condensation of alkylphenol and aldehyde have long been known as flow improvers for mineral oils: see for example EP 311,452 which discloses condensation products of at least 80 mol% of dialkylphenols and aldehydes having 1 to 30 carbon atoms; EP0857776 which describes the use of alkylphenol-aldehyde resins in which the alkyl groups of the alkylphenol have from 4 to 12 carbon atoms and the aldehyde of 1 to 4 carbon atoms and not containing more than 10 mol% of alkylphenols having more than one alkyl group, in combination with ethylene / vinyl ester copolymers or terpolymers for improving the fluidity of mineral oils; EP1584673 which describes Mn alkylphenol-aldehyde resins between 1000 and 3000 from the condensation of a C1-C4 aldehyde and a mixture of predominantly alkyl phenols to monoalkylphenol
  • EP1767610 discloses alkylphenol resins whose condensation reaction with the aldehydes is conducted in the presence of fatty acids having from 2 to 50 carbon atoms, or derivatives thereof, such as esters.
  • the applicant company has discovered that a specific combination of such alkylphenol-aldehyde resins modified with at least one specific filterability additive makes it possible to further improve the cold properties, in particular the cold-holding properties. fuels and liquid fuels hydrocarbon.
  • the applicant company has, in particular, discovered an additive composition that makes it possible to reduce the filterability limit temperature while maintaining the dispersing and / or anti-sedimentation effect of the modified alkylphenol-aldehyde resins described in the patent applications. FR2010 / 61193 and PCT / IB2011 / 055863 .
  • the object of the present invention is to provide additive compositions for improving the cold carrying capacity of fuels and hydrocarbon liquid fuels, in particular, whose boiling point range is between 100 and 500 ° C., or even at above 500 ° C.
  • Another object of the present invention is to provide improved additive compositions for lowering the filterability limit temperature while limiting the sedimentation of paraffins.
  • the present invention also provides an additive composition suitable for being added to fuels and liquid hydrocarbon fuels comprising at least one additional filterability additive to reduce the filterability limit temperature without affecting the effectiveness of the modified alkylphenol-aldehyde resin on dispersion and / or sedimentation of paraffins.
  • the present invention is aimed in particular at a composition of fuels and liquid hydrocarbon fuels having a low filterability temperature (according to the NF EN 116 standard), advantageously less than or equal to -25 ° C., preferably less than or equal to 27 ° C, more preferably less than or equal to -28 ° C and even more preferably less than or equal to -29 ° C.
  • the present invention also aims at a composition of fuels and liquid hydrocarbon fuels having a sedimentation volume according to the ARAL test of less than 10 mL and / or a TLF delta before / after sedimentation (according to standard NF EN 116) less than or equal to 1 ° C and / or PTR delta before / after sedimentation (according to standard NF EN 23015) less than or equal to 1 ° C.
  • the ammonium salts are mono or polycarboxylic acid ammonium salts comprising at least one linear or branched, saturated or unsaturated hydrocarbon-based chain, having between 4 and 30 carbon atoms, and fatty amine and or fatty amine ethoxylated.
  • the modified alkylphenol-aldehyde resin can be obtained from at least one para-substituted alkylphenol, preferably from p-nonylphenol.
  • the modified alkylphenol-aldehyde resin can be obtained from at least one aldehyde and / or a ketone chosen from formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, 2-ethylhexanal, benzaldehyde, acetone, and preferably from at least formaldehyde.
  • the modified alkylphenol-aldehyde resin can be obtained from at least one alkylamine having at least one amine group. primary, and preferably at least one compound in which all their amine groups are primary amines.
  • the modified alkylphenol-aldehyde resin can be obtained from p-nonylphenol, formaldehyde and at least one hydrocarbon compound having at least one alkylmonoamine or alkylpolyamine group.
  • the modified alkylphenol-aldehyde resin can be obtained from at least one fatty-chain alkylamine or a mixture of fatty-chain alkylamines, and preferably alkylamine (s) having a number carbon atoms between 12 and 24, preferably between 12 and 22.
  • the modified alkylphenol-aldehyde resin has a viscosity at 50 ° C., measured using a dynamic rheometer at a shear rate of 100 s -1, on a solution of said resin diluted with 30% by mass.
  • an aromatic solvent of between 1000 and 10 000 mPa.s, preferably 1500 and 6000 mPa.s and advantageously between 2500 and 5000 mPa.s.
  • Another subject of the invention relates to an additive composition
  • an additive composition comprising in addition at least one additional filterability additive chosen from copolymers and terpolymers of ethylene and of vinyl ester and / or of acrylic ester (EVA and / or TEU).
  • the additional filterability additive is selected from copolymers of ethylene and vinyl ester (EVA).
  • Another object of the invention also relates to the use of an additive composition according to the invention, in a fuel or a hydrocarbon liquid fuel to improve the cold properties, in particular to reduce the filterability temperature (TLF). measured according to standard NF EN 116, without affecting the effectiveness of the modified alkylphenol-aldehyde resin on the dispersion and / or sedimentation of paraffins.
  • TEZ filterability temperature
  • Another object of the invention relates to the use of a composition according to the invention, in hydrocarbon liquid fuels and fuels, for improving the cold properties of hydrocarbon liquid fuels and fuels.
  • the fuels and / or fuels have a boiling range ranging from 120 to 500 ° C., preferably 140 to 400 ° C., and advantageously, are chosen from jet fuels, gas oils, diesel fuels, domestic fuel oil and heavy fuel oil.
  • an additive composition comprises at least one modified alkylphenol-aldehyde resin and at least one filterability additive.
  • filterability additive is understood to mean an additive facilitating germination, limiting the growth of paraffin crystals and thus improving the flow of liquid hydrocarbon fuels and in particular by reducing their filterability temperature (TLF). These filterability additives are also referred to as TLF additives or CFI additive ( Cold Flow Improver ).
  • the modified alkylphenol-aldehyde resin according to the invention is advantageously obtained from at least one para-substituted alkylphenol.
  • Nonylphenol will preferably be used.
  • the average number of phenol nuclei per molecule of nonylphenol-aldehyde resin preferred is preferably greater than 6 and less than or equal to 25 and more preferably between 8 and 17, and even more preferably between 9 and 16, phenolic rings per molecule.
  • the number of phenolic nuclei can be determined by nuclear magnetic resonance (NMR) or gel permeation chromatography (GPC).
  • the modified alkylphenol-aldehyde resin may be obtained from at least one aldehyde and / or a ketone chosen from formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, 2-ethylhexanal and benzaldehyde. acetone, preferably at least formaldehyde.
  • the modified alkylphenol-aldehyde resin is obtained from at least one alkylamine having at least one primary amine group.
  • the modified alkylphenol-aldehyde resin can advantageously be obtained from at least one alkylamine having at least one primary amine group and at least one compound all of whose amine groups are primary amines.
  • the alkylamine is preferably a fatty chain alkylamine having 12 to 24 carbon atoms, preferably 12 to 22 carbon atoms.
  • the modified alkylphenol-aldehyde resin is obtained from at least one alkylamine having at least one primary amine group and comprising a fatty chain having between 12 and 24 carbon atoms, preferably between 12 and 20 atoms. of carbon.
  • alkylamines are generally not pure compounds but mixtures.
  • fatty-chain alkylamines which are suitable, mention may especially be made of the fatty-chain alkylamines marketed under the names: Noram®, Trinoram®, Duomeen®, Dinoram®, Trinoram®, Triameen®, Armeen®, Polyram®, Lilamin® and Cemulcat® .
  • Trinoram S which is a dipropylenetriamine of tallow, also known under the name N- (Tallowalkyl) dipropylenetriamine.
  • the viscosity of the modified alkylphenol-aldehyde condensation resin is preferably range between 1000 and 10,000 mPa.s, preferably between 1500 and 6000 mPa.s, and advantageously between 2500 and 5000 mPa.s.
  • the filterability additive is, for example, a random terpolymer of stearyl methacrylate, C 20 -C 24 alpha-olefin and N-tallow maleimide (density at 15 ° C: 890-930 kg / m3 - point flash:> 55 ° C (NF EN ISO 22719), self-ignition temperature:> 450 ° C, marketed by the company Total Additives & Special Fuels under the name TP.
  • the alkyl (meth) acrylate homopolymers preferably have a weight average molecular weight Mw between 5,000 and 20,000, preferably between 7,000 and 19,000, and even more preferably between 10,000 and 19,000.
  • the average molecular weight can conventionally be measured with a viscometric detector or by calibration with a standard, for example polymethyl methacrylate or polystyrene.
  • ammonium salts are advantageously ammonium salts of mono or polycarboxylic acids comprising at least one hydrocarbon chain, linear or branched, saturated or unsaturated, having from 4 to 30 carbon atoms, preferably from 10 to 24 atoms of carbon and fatty amine and / or ethoxylated fatty amine.
  • the fatty amines may optionally be hydrogenated and / or contain one or more units of ethylene oxide (ethoxylated amine).
  • the fatty amines generally have a saturated or unsaturated hydrocarbon chain length ranging from 4 to 30 carbon atoms, optionally hydrogenated.
  • tallow fatty amines predominantly C 16 -C 18 , which are optionally hydrogenated and which may contain from 3 to 8 ethylene oxide units, preferably from 5 to 7 oxide units. ethylene.
  • the modified alkylphenol-aldehyde resin mass ratio: filterability additive is between 1:99 and 99: 1, preferably between 90:10 and 10:90, more preferably between 70:30 and 30:70.
  • the additive composition may also include one or more solvents or dispersants.
  • the solvent or dispersing agent is chosen from aliphatic and / or aromatic hydrocarbons or hydrocarbon mixtures, for example gasoline fractions, kerosene, decane, pentadecane, toluene, xylene, ethylbenzene, commercial solvent mixtures such as Solvarex 10, Solvarex 10 LN, Solvent Naphtha, Shellsol AB, Shellsol D, Solvesso 150, Solvesso 150 ND, Solvesso 200, Exxsol, ISOPAR.
  • the mass concentration of the modified alkylphenol-aldehyde resin in the additive composition may advantageously vary from 1 to 99.5%, preferably from 5 to 95%, more preferably 10 to 90% and even more preferably 30 to 90%.
  • the mass concentration of the filterability additive in the additive composition can advantageously vary from 0.5 to 99%, preferably from 1 to 70% and, more preferably, from 1 to 50% and more preferably from 1 to 30%. %.
  • Polar dissolution adjuvants such as 2-ethylhexanol, decanol, isodecanol and / or isotridecanol can also be added to the additive composition.
  • additives mentioned above namely the modified alkylphenol-aldehyde resins and the filterability additive
  • other additives may also be added in the additive composition such as corrosion inhibitors, detergency additives, anti-haze agents, additives improving conductivity, dyes, deodorants, lubricity additives or lubricity additives ...
  • the additive compositions are, for example, prepared by solubilizing or dispersing each component, separately or in admixture, with one or more solvents or dispersants described above.
  • the second particular embodiment is identical to the first particular embodiment, except that the composition comprises at least the first filterability additive and at least the second filterability additive.
  • modified alkylphenol-aldehyde resins, terpolymers of (meth) acrylate and the ammonium salts are as described in the first particular embodiment.
  • the modified alkylphenol-aldehyde resin mass ratio : first and second filterability additives is advantageously between 1:99 and 99: 1, preferably between 10:90 and 90:10 and, more preferably, between 30:70 and 70: 30.
  • the first filterability additive mass ratio: second filterability additive is advantageously between 1:99 and 99: 1, preferably between 10:90 and 90:10 and, more preferably, between 70:30 and 30: 70.
  • the mass concentration of the modified alkylphenol-aldehyde resin in the additive composition may advantageously vary from 1 to 99%, preferably from 5 to 95%, more preferably from 10 to 90% and even more preferably from 30 to 90%. .
  • the mass concentration of the first filterability additive in the additive composition can advantageously vary from 0.5 to 99%, preferably from 1 to 70% and, more preferably, from 1 to 50% and more preferably from 1 to 30%. %.
  • the mass concentration of the second filterability additive in the additive composition can advantageously vary from 0.5 to 99%, preferably from 1 to 70%, more preferably from 1 to 50% and more preferably from 1 to 30%. .
  • the additive composition according to the first and second particular embodiments may be used in a fuel or liquid hydrocarbon fuel preferably comprising at least one additional filterability additive selected from ethylene and polyethylene copolymers and terpolymers.
  • additional filterability additive selected from ethylene and polyethylene copolymers and terpolymers.
  • vinyl ester and / or acrylic to improve the cold properties, in particular the filterability temperature (TLF) measured according to standard NF EN 116, without affecting the effectiveness of the modified alkylphenol-aldehyde resin on the dispersion and / or the sedimentation of paraffins.
  • the additional filterability additive is preferably selected from copolymers or terpolymers of ethylene and vinyl acetate and / or vinyl propionate and / or vinyl versatate; ethylene and / or (alkyl) acrylates and / or (alkyl) methacrylates, it being understood that the alkyl group of the (alkyl) acrylates and (alkyl) methacrylates advantageously contains from 1 to 40 carbon atoms, from preferably from 16 to 24 carbon atoms, taken alone or as a mixture.
  • Copolymers and terpolymers of ethylene and vinyl ester and / or acrylic ester advantageously have average molecular weights M w ranging from 1000 to 20 000 g / mol, preferably from 2000 to 10 000 g / mol.
  • copolymer-type additional filterability additives By way of example of copolymer-type additional filterability additives, mention may be made of copolymers of ethylene and of vinyl acetate (EVA) preferably having weight average molecular weights M w ranging from 1000 to 20 000 g / mol, of preferably from 2000 to 10,000 g / mol.
  • EVA vinyl acetate
  • terpolymers mention may be made of those which are described in EP 1 692 196 , WO09 / 106743 and WO09 / 106744 .
  • the additional filterability additive may be present in the liquid hydrocarbon fuel or fuel in an amount advantageously ranging from 1 to 1000 ppm, preferably from 5 to 500 ppm, more preferably from 5 to 150 ppm and even more preferably from 5 to 135 ppm.
  • the additive composition as described above in the first and second embodiments further comprises at least one filtering dispersant improving cold flow, in particular an additive.
  • additional filterability selected from copolymers and terpolymers of ethylene and vinyl ester and / or acrylic ester.
  • the additional filterability additive is as described above.
  • the additive composition according to the third embodiment can be used in liquid hydrocarbon fuels to improve the cold properties of hydrocarbon liquid fuels and fuels, particularly those as described above.
  • the additive composition according to the third embodiment is particularly suitable for reducing both the filterability limit temperature (TLF) and the paraffin dispersion and / or to limit the sedimentation of paraffins in liquid hydrocarbon fuels.
  • TLF filterability limit temperature
  • the additive composition according to the third embodiment can be used as additives for improving the cold properties of fuel oils and petroleum distillates of petroleum origin and / or of renewable origin, and more particularly middle distillates. whose boiling temperature range is mainly between 100 and 500 ° C.
  • the middle distillates targeted by the invention have in particular a TLF according to EN 116 between -30 ° C and + 15 ° C, preferably between -30 ° C and 0 ° C and more preferably between -30 ° C and -20 ° C.
  • This additive composition is particularly effective for fuels and / or fuels which have a boiling range of from 120 to 500 ° C., preferably from 140 to 400 ° C., and advantageously chosen from jet fuels and gas oils. , diesel fuels, heating oil and heavy fuel oil.
  • Another subject of the invention relates to a composition of liquid hydrocarbon fuels or fuels whose boiling temperature range is mainly between 100 and 500 ° C, preferably between 120 and 500 ° C, more preferably between 140 and 400 ° C. C, and advantageously, selected from jet fuels, gas oils, diesel fuels, domestic fuel oil and heavy fuel oil.
  • majority proportion a mass proportion advantageously greater than or equal to 97%, preferably greater than or equal to 98%, more preferably greater than or equal to 99%.
  • minority proportion is meant a proportion advantageously between 5 and 5000 ppm by weight, preferably between 5 and 1000 ppm, more preferably between 50 and 3000 ppm and even more preferentially between 5 and 500 ppm.
  • composition of liquid hydrocarbon fuels or fuels comprises a minority proportion of at least one composition as described in the third embodiment, that is to say with the additional filterability additive.
  • the modified alkylphenol-aldehyde resin is advantageously present in the liquid hydrocarbon fuel or fuel in an amount ranging from 0.5 to 2000 ppm, preferably from 0.5 to 500 ppm, more preferably from 0.5 to 100 ppm, and even more preferably from 1 to 70 ppm
  • the filterability additive or the first and second filterability additives are advantageously present in the liquid hydrocarbon fuel or fuel in an amount ranging, respectively, from 0.5 to 2000 ppm, preferably from 0.5 to 500 ppm, more preferably from 0.5 to 100 ppm and even more preferably from 1 to 70 ppm.
  • the additional filterability additive is advantageously present in the liquid hydrocarbon fuel or fuel in an amount ranging from 1 to 1000 ppm, preferably from 50 to 500 ppm, more preferably from 100 to 400 ppm and even more preferably from 50 to 400 ppm.
  • Each of the other additives described above may be present in the fuel or liquid hydrocarbon fuel in an amount ranging from 0.5 to 1000 ppm, preferably from 1 to 500 ppm, even more preferably from 1 to 400 ppm.
  • T cc of the liquid hydrocarbon fuel or fuel measured by Differential Calorimetric Analysis is often greater than or equal to -20 ° C, generally between -15 ° C and + 10 ° C.
  • distillates may, for example, be chosen from distillates obtained by direct distillation of crude hydrocarbons, vacuum distillates, hydrotreated distillates, distillates obtained from catalytic cracking and / or hydrocracking of distillates under vacuum, distillates resulting from ARDS (by atmospheric residue desulphurisation) and / or visbreaking conversion processes, distillates from the valuation of Fischer Tropsch cuts, distillates resulting from BTL ( biomass to liquid ) conversion of biomass plant and / or animal, and / or mixtures thereof.
  • Hydrocarbon liquid fuels may also contain distillates from more complex refining operations than those derived from the direct distillation of hydrocarbons.
  • the distillates may, for example, be derived from cracking, hydrocracking and / or catalytic cracking processes and visbreaking processes.
  • These new fuels and fuel bases can be used alone or mixed with conventional petroleum distillates as conventional diesel fuel base and / or domestic fuel base. They generally comprise long paraffinic chains greater than or equal to 10 carbon atoms and preferably C 14 to C 30 .
  • the sulfur content of the liquid hydrocarbon fuel and fuel compositions is less than 5000 ppm, preferably less than 500 ppm, and more preferably less than 50 ppm, or even less than 10 ppm, and advantageous without sulfur, especially for diesel type fuels.
  • alkylphenol-aldehyde resins are prepared by condensation of para-nonylphenol and formaldehyde (for example according to the procedure described in US Pat. EP 857 776 ) viscosities at 50 ° C (measured at 50 ° C using a dynamic rheometer with a shear rate of 10 s -1 on the resin diluted with 30% by mass of aromatic solvent (Solvesso 150) between 1800 and 4800 mPa.s.
  • the alkylphenol-aldehyde resins derived from the first step are modified by reaction of Mannich by addition of formaldehyde and primary alkyl (poly) amine (for example an alkylpolyamine having a C12 alkyl chain (marketed under the name Noram® C) for the resin (1 A).
  • formaldehyde and primary alkyl (poly) amine for example an alkylpolyamine having a C12 alkyl chain (marketed under the name Noram® C) for the resin (1 A).
  • Each of the modified alkylphenol aldehyde resins of Example 1 is evaluated as an anti-sedimentation additive or WASA alone (ie not associated with another dispersant component WASA) in a diesel fuel (GOM 1) additive with 300 ppm by weight of a TLF additive which is an EVA, in solution at 70% by weight in an aromatic solvent (Solvesso 150 type), marketed under the name CP7936C .
  • Each modified alkyl phenol resin is incorporated into the gas oil at a concentration of 70 ppm by weight (the resin being dissolved with 30% by weight of solvent, 100 ppm by weight of 70% solution of active material are used).
  • GOM 1 additivated gas oil with 300 ppm of the TLF additive described above and the unmodified alkyl phenol aldehyde resin are also evaluated.
  • the anti-settling properties of the additives are evaluated by the following ARAL sedimentation test: 500mL of additive middle distillates are cooled in 500mL specimens in a climatic chamber at -13 ° C according to the following temperature cycle: + 10 ° C to -13 ° C in 4h then isothermal at -13 ° C for 16h.
  • ARAL sedimentation test 500mL of additive middle distillates are cooled in 500mL specimens in a climatic chamber at -13 ° C according to the following temperature cycle: + 10 ° C to -13 ° C in 4h then isothermal at -13 ° C for 16h.
  • NF EN 23015 characterization in PTR cloud point
  • TLF NF EN 116
  • the unmodified conventional alkylphenol resin (comparative resin 1) does not perform well in anti-sedimentation when it is used alone (ie without addition of dispersant) while the alkylphenol resins modified according to the invention are more efficient being the resin 2C, containing dipropylenetriamine tallow, particularly preferred.
  • the additive mixture contains 20% by weight of resin 1 and 80% by weight of dodecenylsuccinic anhydride amidated polar dispersion dispersant with a tallow dipropylenetriamine.
  • Table 3 WASA additive (s) used Resin added (ppm of 70% solution of active ingredient) Visual Rating Test specimen (volume of sediment in mL over 500 mL of sample) TLF measurement (° C) PTR measurement (° C) NF EN 116 NF EN 23015 Before After difference Before After difference No WASA 0 -16
  • Resin 2C 75 ⁇ 5 homogeneous -20 -17 -3 -6 -6 0 Comparative resin + dispersant 75 ⁇ 10 homogeneous -18 -17 -1 -7 -6 -1 Resin 2C 50 10 -19 -17 -2 -6 -6 0
  • GOM 2 gasolines B5 type gas oil, ie containing 5% volume of EMHV
  • GOM 3 B0 type gasoil without EMHV
  • Table 6 The characteristics of the GOM 2 and GOM 3 gas oils are shown in Table 6 below.
  • Additive compositions referenced A 1 to A 6 as well as five control additive compositions T 1 and T 2 and A 0 1 to A 0 3 are obtained either by mixing the unmodified alkylphenol-aldehyde resin Resin 1 in the solvent. or Resin 2C-modified alkylphenol-aldehyde resin in the solvent and, optionally, one or more filterability additives in the proportions defined in Table 7.
  • PA TP SA PA: TP: SA T 1 0 20 0 0 0 100: 0: 0: 0 - A 0 1 0 20 6 0 0 76.9: 23.1: 0: 0 100: 0: 0 A 0 2 0 20 3 5 0 71.4: 10.7: 17.9: 0 37.5: 62.5: 0 A 0 3 0 20 0 0 10 66.7: 0: 0: 33.3 0: 0: 100 T 2 20 0 0 0 0 0 100: 0: 0: 0 - A 1 20 0 6 0 0 76.9: 23.1: 0: 0 100: 0: 0 A 2 20 0 3 5 0 71.4: 10.7: 17.9: 0 37.5: 62.5: 0 A 3 20 0 0 0 0 10 66.7: 0: 0: 33.3 0: 0: 100 T 2 20 0 0 0 0 0 100:
  • a control composition C 0 is obtained from a diesel engine GOM 4 additive with 300 ppm by weight of an additional filterability additive which is a mixture of ethylene / vinyl acetate copolymers (EVA) in solution at 70% by weight in an aromatic solvent Solvesso 150, noted EVA1, marketed by the company Total Additives & Special Fuels under the name CP7870C.
  • EVA ethylene / vinyl acetate copolymers
  • C 1 to C 6 liquid hydrocarbon fuels or hydrocarbon fuels as well as five control compositions C T1 and C T5 are obtained from a GOM 4 or 5 additive gas oil with 300 ppm by weight of the additional filterability additive EVA1 and a additive composition selected from T 1 , T 2 , A 0 1 , A 0 2 , A 0 3 , or A 1 to A 6 .
  • the anti-sedimentation properties of the additive compositions for each of the liquid hydrocarbon fuel compositions or liquid hydrocarbon fuels C 1 to C 6 and for the six control compositions C 0 , C T1 to C T5 are evaluated according to an ARAL sedimentation test. identical to that of Example 2.
  • the test on the control composition C 0 makes it possible to evaluate the effect on sedimentation and TLF of the additional filterability additive EVA1 alone.
  • the test on the control composition C T5 makes it possible to evaluate the effect on the sedimentation and TLF of the additional filterability additive EVA1 in combination with a modified alkylphenol-aldehyde resin (Resin 2C) compared to the test on the control composition C T1 made with the unmodified resin (Resin 1).
  • the tests of control compositions C 1 to C 6 make it possible to evaluate the effect on sedimentation and TLF of the additional filterability additive EVA1 in combination with a modified alkylphenol-aldehyde resin (Resin 2C) formulated with the filterability additives. PA, TP and / or SA compared to the tests of control compositions C T2 to C T4 , carried out with the unmodified resin (Resin 1).
  • compositions C 1 to C 6 have a lower TLF and improved anti-sedimentation properties compared to compositions C 0 , C T1 and C T5 .
  • a combined effect on TLF and anti-sedimentation performance is observed, with a TLF of up to -30 ° C (C 1 ), a difference of TLF and / or PTR before / after sedimentation of 0 or 1 ° C maximum.
  • the addition of the filterability additive PA, TP or SA to the modified alkylphenol-aldehyde resin (Resin 2C) makes it possible to lower the TLF by about 5 ° C. with respect to the TLF of the composition C T5 , without affect the anti-sedimentation performance provided by the modified alkylphenol-aldehyde resin (Resin 2C).

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Publication number Publication date
EP2867348A1 (fr) 2015-05-06
PT2867348T (pt) 2018-11-15
BR112014032022A2 (pt) 2017-06-27
US9534183B2 (en) 2017-01-03
WO2013189868A1 (fr) 2013-12-27
US20150113863A1 (en) 2015-04-30
FR2991992B1 (fr) 2015-07-03
CA2874572A1 (fr) 2013-12-27
CN104508092B (zh) 2017-03-01
JP6143855B2 (ja) 2017-06-07
CA2874572C (fr) 2020-04-14
TR201816251T4 (tr) 2018-11-21
ES2693569T3 (es) 2018-12-12
KR20150023280A (ko) 2015-03-05
CN104508092A (zh) 2015-04-08
JP2015520284A (ja) 2015-07-16
EA201590046A1 (ru) 2015-03-31
EA026728B1 (ru) 2017-05-31
PL2867348T3 (pl) 2019-02-28
FR2991992A1 (fr) 2013-12-20
KR102063572B1 (ko) 2020-01-09
AR092016A1 (es) 2015-03-18

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