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US20150033617A1 - Additive compositions for improving the lacquering resistance of higher grade fuels of the diesel or biodiesel type - Google Patents

Additive compositions for improving the lacquering resistance of higher grade fuels of the diesel or biodiesel type Download PDF

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Publication number
US20150033617A1
US20150033617A1 US14/365,033 US201214365033A US2015033617A1 US 20150033617 A1 US20150033617 A1 US 20150033617A1 US 201214365033 A US201214365033 A US 201214365033A US 2015033617 A1 US2015033617 A1 US 2015033617A1
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US
United States
Prior art keywords
bis
tert
thiadiazole
methyl
diesel
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US14/365,033
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English (en)
Inventor
Mathieu Arondel
Bernardé Dequenne
Hèléne Rodeschini
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TotalEnergies Marketing Services SA
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Total Marketing Services SA
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Assigned to TOTAL MARKETING SERVICES reassignment TOTAL MARKETING SERVICES ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: ARONDEL, Mathieu, DEQUENNE, BERNARD, RODESCHINI, HELENE
Publication of US20150033617A1 publication Critical patent/US20150033617A1/en
Abandoned legal-status Critical Current

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    • C10L10/06—Use of additives to fuels or fires for particular purposes for facilitating soot removal
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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/10—Biofuels, e.g. bio-diesel

Definitions

  • the present invention relates to the use of additive compositions for higher grade fuels of the diesel or biodiesel type (Bx) for improving lacquering resistance.
  • Diesel or biodiesel fuels are fuels which can be used for supplying compression ignition engines or diesel engines in automobiles (private cars, commercial vehicles, lorries, etc.).
  • additives chemical compounds incorporated in fuels to improve their properties, for example additives for improving cold resistance
  • the oil companies and the distributors are free to add or not add additives to their fuels.
  • higher-grade fuel of the diesel or biodiesel type is meant any diesel or biodiesel fuel to which at least 50 ppm w/w of deposit reducer(s)/dispersant(s) has been added.
  • the lacquering phenomenon can be localized on the end of the injector needles, both on the head and on the body of the needles of the fuel injection system but also throughout the system controlling the needle lift (valves) of the injection system, for vehicle engines operating on diesel or biodiesel fuel, and can eventually generate a loss of flow rate of fuel injected and therefore a loss of engine power.
  • Another possible source of sodium can be from the corrosion inhibitors used when petroleum products are conveyed in certain pipes, such as sodium nitrite;
  • DDSA dodecenylsuccinic anhydride
  • HDSA hexadecenylsuccinic anhydride
  • these salts are insoluble in low-sulphur diesel fuels, and as they are in the form of fine particles they pass through diesel fuel filters and are deposited inside the injectors.
  • diesel fuel filters and are deposited inside the injectors.
  • This publication emphasizes that only the diacids generate deposits, in contrast to monocarboxylic acids or the neutral esters of organic acids.
  • the deposits due to the lacquering phenomenon are insoluble in low-sulphur diesel fuels and in biodiesel fuels. These deposits are in the form of fine particles and can pass through diesel fuel filters and can then be deposited inside the injectors.
  • the vehicle could have great difficulty starting, or even not start of all, since the needle permitting injection would be blocked.
  • the present invention makes it possible to overcome the problems indicated above.
  • the present invention proposes additive compositions that can tangibly improve the lacquering resistance of higher-grade diesel and biodiesel fuels, i.e. with the addition of at least 50 ppm by weight of deposit reducer(s)/dispersant(s).
  • the deposit reducer or reducer(s)/dispersants used in higher-grade fuels are generally selected from:
  • substituted amines such as N-polyisobutene amine R1-NH 2 , N-polyisobutene-ethylenediamine R1-NH—R2-NH 2 ,
  • R represents a polyisobutene group of molecular weight between 140 and 5000 and preferably between 500 and 2000 or preferably between 750 and 1250; or their bissuccinimide, succinnamic, succinamide structural equivalents, and where R2 represents at least one of the following segments —CH 2 —CH 2 —, CH 2 —CH 2 —CH 2 , —CH—CH(CH 3 )— and x represents an integer between 1 and 6.
  • polyethylenamines are particularly effective. They are described for example in detail in the reference “Ethylene Amines,” Encyclopedia of Chemical Technology, Kirk and Othmer, Vol. 5, pp. 898-905, Interscience Publishers, New York (1950).
  • R is an alkyl or aryl group having from 1 to 30 carbon atoms
  • R1 and R2 are each independently a hydrogen atom, an alkyl chain with 1 to 6 carbon atoms or —O—CHR1-CHR2-
  • A is an amine or N-alkylamine with 1 to 20 carbon atoms in the alkyl chain, an N,N-dialkylamine having from 1 to 20 carbon atoms in each alkyl group, or a polyamine with 2 to 12 nitrogen atoms and from 2 to 40 carbon atoms and x is in the range from 5 to 30.
  • Such polyetheramines are marketed for example by the companies BASF, HUNSTMAN or CHEVRON.
  • the alkyl group of the alkylated phenol can comprise from 10 to 110 carbon atoms. This alkyl group can be obtained by polymerization of olefinic monomer containing from 1 to 10 carbon atoms (ethylene; propylene; 1-butene, isobutylene and 1-decene).
  • the polyolefins that are used in particular are polyisobutene and/or polypropylene.
  • the polyolefins generally have a weight-average molecular weight Mw between 140 and 5000 and preferably between 500 and 2000 or preferably between 750 and 1250.
  • the alkyl phenols can be prepared by an alkylation reaction between a phenol and an olefin or a polyolefin such as polyisobutylene or polypropylene.
  • the aldehyde used can contain from 1 to 10 carbon atoms, generally formaldehyde or paraformaldehyde.
  • the amine used can be an amine or a polyamine including the alkanolamines having one or more hydroxyl groups.
  • the amines used are generally selected from ethanolamine, diethanolamines, methylamine, dimethylamine, ethylenediamine, dimethylaminopropylamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine and/or 2-(2-aminoethylamino)ethanol.
  • This dispersant can be prepared by a Mannich reaction by reacting an alkylphenol, an aldehyde and an amine as described in patent U.S. Pat. No. 5,697,988.
  • carboxylic dispersants such as those described in U.S. Pat. No. 3,219,666;
  • polymeric dispersants obtained by polymerization of alkyl acrylates or alkyl methacrylates (C8 to C30 alkyl chains), aminoalkyl acrylates or acrylamides and acrylates substituted with poly(oxyethylene) groups. Examples of polymeric dispersants are described for example in U.S. Pat. No. 3,329,658 and U.S. Pat. No. 3,702,300;
  • dispersants containing at least one aminotriazole group such as described for example in U.S. Patent Publication No. 2009/0282731 resulting from reaction of a dicarboyxlic acid or anhydride substituted with a hydrocarbyl and an amine compound or salt of the (amino)guanidine type;
  • oligomers of PIBSA and/or of DDSA and of hydrazine monohydrate such as those described in EP 1,887,074;
  • oligomers of ethoxylated naphthol and of PIBSA such as those described in EP 1,884,556;
  • Mannich bases for example dodecylphenol/ethylenediamine/formaldehyde
  • PIBSI such as those described in WO2010/097624 and WO 2009/040582
  • the present invention relates to the use of additive compositions for improving the lacquering resistance of higher-grade diesel and biodiesel fuels, said compositions comprising at least one antioxidant of the hindered phenol type (alkylphenol) at and at least one metal passivator b/.
  • the additive compositions for fuels, in particular of the diesel or biodiesel type, used in the invention for improving lacquering resistance comprise:
  • At least one antioxidant of the hindered phenol type (alkylphenol) at and
  • the improvement in lacquering resistance provided by the additive compositions of the present invention is totally different from the improvement in the oxidation resistance of biodiesels as described for example in EP 2,087,074, EP 2,132,285 or EP 2,173,838.
  • the oxidation phenomenon described in these documents takes place under the action in particular of light and air.
  • the deposits due to the lacquering phenomenon are produced actually inside the engine, on the injector, i.e. in an environment away from the light.
  • the lacquering phenomenon causes the appearance of deposits that appear specifically on the injectors and that result in particular from the chemical reaction of an acidic friction modifier and a deposit reducer/dispersant forming notably salts.
  • the antioxidant or antioxidants a/ of the hindered phenol type can be selected from molecules comprising at least one hindered phenol group (alkylphenols).
  • antioxidants of the hindered phenol type there may be mentioned di-t-butyl-2,6-methyl-4-phenol (BHT), t-butyl hydroquinone (TBHQ), 2,6- and 2,4-di-t-butyl phenol, 2,4-dimethyl-6-t-butyl phenol, pyrogallol, tocopherol, 4,4′-methylene bis(2,6-di-t-butyl phenol) (CAS No. 118-82-1), alone or in a mixture.
  • BHT di-t-butyl-2,6-methyl-4-phenol
  • TBHQ t-butyl hydroquinone
  • 2,6- and 2,4-di-t-butyl phenol 2,4-dimethyl-6-t-butyl phenol
  • pyrogallol tocopherol
  • the preferred antioxidants of the hindered phenol type a/ comprise one or more of the following molecules comprising at least one hindered phenol group, alone or in a mixture: di-t-butyl-2,6-methyl-4-phenol (BHT), t-butyl hydroquinone (TBHQ), 2,6- or 2,4-di-t-butyl phenol, 2,4-dimethyl-6-t-butyl phenol alone or in a mixture.
  • BHT di-t-butyl-2,6-methyl-4-phenol
  • TBHQ t-butyl hydroquinone
  • 2,6- or 2,4-di-t-butyl phenol 2,4-dimethyl-6-t-butyl phenol alone or in a mixture.
  • the metal passivator or passivators b/ can be selected from amines substituted with triazole groups (benzotriazole, toluoyltriazole, etc.) such as N,N-bis(2-ethylhexyl)-1,2,4-triazol-1-ylmethanamine (CAS 91273-04-0), N,N′-bis(2 ethylhexyl)-4-methyl-1H-benzotriazol-1-methyl-amine (CAS 80584-90-3), N,N-bis(heptyl)-ar-methyl-1H-benzotriazole-1-methanamine, N,N-bis(nonyl)-ar-methyl-1H-benzotriazole-1-methanamine, N,N-bis(decyl)-ar-methyl-1H-benzotriazole-1-methanamine, N,N-bis(undecyl)-ar-methyl-1H-benzotriazole-1-methanamine, N,N-bis(d
  • the metal passivator or passivators b/ are selected from N,N-bis(2-ethylhexyl)-1,2,4-triazol-1-ylmethanamine (CAS 91273-04-0) and/or N,N′-bis(2-ethylhexyl)-4-methyl-1H-benzotriazol-1-methyl-amine (CAS 80584-90-3), alone, or in a mixture with other known metal passivators usually encountered in engines, in particular passivators of copper, of zinc.
  • the additive compositions according to the invention comprise:
  • a/ at least one antioxidant of the hindered phenol type (alkylphenol) containing one or more alkylphenols selected from di-t-butyl-2,6-methyl-4-phenol (BHT), t-butyl hydroquinone (TBHQ), 2,6- or 2,4-di-t-butyl phenol, 2,4-dimethyl-6-t-butyl phenol, alone or in a mixture,
  • alkylphenol containing one or more alkylphenols selected from di-t-butyl-2,6-methyl-4-phenol (BHT), t-butyl hydroquinone (TBHQ), 2,6- or 2,4-di-t-butyl phenol, 2,4-dimethyl-6-t-butyl phenol, alone or in a mixture
  • b/ at least one metal passivator preferably comprising N,N-bis(2-ethylhexyl)-1,2,4-triazol-1-ylmethanamine (CAS 91273-04-0) and/or N,N′-bis(2 ethylhexyl)-4-methyl-1H-benzotriazol-1-methyl-amine (CAS 80584-90-3), alone or in a mixture with other metal passivators.
  • the additive compositions comprise a passivator/antioxidant with a weight ratio in the range from 1/10 to 2, preferably in the range from 1/6 to 1, advantageously from 1/5 to 1/2.
  • the additive compositions used in the invention comprise di-t-butyl-2,6-methyl-4-phenol (BHT) and N,N-bis(2-ethylhexyl)-1,2,4-triazol-1-ylmethanamine (CAS 91273-04-0).
  • the additive compositions used comprise t-butyl hydroquinone (TBHQ) and N,N-bis(2-ethylhexyl)-1,2,4-triazol-1-ylmethanamine (CAS 91273-04-0).
  • the additive compositions used comprise di-t-butyl-2,6-methyl-4-phenol (BHT) and N,N′-bis(2-ethylhexyl)-4-methyl-1H-benzotriazol-1-methyl-amine (CAS 80584-90-3).
  • the additive compositions comprise t-butyl hydroquinone (TBHQ) and N,N′-bis(2-ethylhexyl)-4-methyl-1H-benzotriazol-1-methyl-amine (CAS 80584-90-3).
  • the additive compositions according to the invention can also contain other additives, of a different chemical nature and/or with different functionality or functionalities.
  • the compositions according to the invention can contain, non-exhaustively:
  • the additive compositions according to the invention comprise:
  • At least one antioxidant of the hindered phenol type (alkylphenol)
  • At least one conventional deposit reducer/dispersant at least one conventional deposit reducer/dispersant.
  • the additive compositions comprise:
  • At least one conventional deposit reducer/dispersant preferably in a quantity of up to 80% by weight, more preferably in the range from 30 to 70% by weight.
  • substituted amines such as N-polyisobutene amine R1-NH 2 , N-polyisobutene-ethylenediamine R1-NH—R2-NH 2 ,
  • R represents a polyisobutene group of molecular weight between 140 and 5000 and preferably between 500 and 2000 or preferably between 750 and 1250; or their bissuccinimide, succinnamic, succinamide structural equivalents, and where R2 represents at least one of the following segments —CH 2 —CH 2 —, CH 2 —CH 2 —CH 2 , —CH—CH(CH 3 )— and x represents an integer between 1 and 6.
  • R is an alkyl or aryl group having from 1 to 30 carbon atoms
  • R1 and R2 are each independently a hydrogen atom, an alkyl chain with 1 to 6 carbon atoms or —O—CHR1-CHR2-
  • A is an amine or N-alkylamine with 1 to 20 carbon atoms in the alkyl chain, an N,N-dialkylamine having from 1 to 20 carbon atoms in each alkyl group, or a polyamine with 2 to 12 nitrogen atoms and from 2 to 40 carbon atoms and x is in the range from 5 to 30,
  • the deposit reducer/dispersant is selected from PIBSI (polyisobutene succinimide) and EDTA/DDSA (ethylenediaminetetraacetic acid/dodecenylsuccinic anhydride).
  • the additive composition can also contain one or more hydrocarbon organic solvents and optionally at least one compatibilizing agent or co-solvent.
  • the additive composition further comprises at least one hydrocarbon organic solvent and/or at least one compatibilizing agent or co-solvent.
  • the cold resistance additive or additives can be selected from additives for improving the pour point, additives for improving the cold filter-plugging point (CFPP), additives for improving the cloud point and/or anti-sedimentation additives and/or wax dispersants.
  • additives for improving the pour point and filterability CFI
  • copolymers of ethylene and vinyl acetate (EVA) and/or copolymers of ethylene and vinyl propionate (EVP) may be mentioned.
  • additives for improving CFPP cold operability polyfunctional additives in particular selected from the group comprising polymers based on olefin and alkenyl nitrate such as those described in EP 573 490 may be mentioned.
  • additives for improving the cloud point there may be mentioned, non-limitatively, compounds selected from the group consisting of the long-chain olefin/(meth)acrylic ester/maleimide terpolymers, and the polymers of fumaric/maleic acid esters.
  • examples of such additives are given in EP 71 513, EP 100 248, FR 2 528 051, FR 2 528 423, EP1 12 195, EP 1 727 58, EP 271 385, EP 291367.
  • anti-sedimentation additives and/or wax dispersants it is in particular possible to use the anti-sedimentation additives selected (but not limitatively) from the group consisting of the copolymers of (meth)acrylic acid/alkyl (meth)acrylate amidated by a polyamine, polyamine alkenyl succinimides, derivatives of phthalamic acid and of double-chain fatty amine; alkyl phenol/aldehyde resins; examples of such additives are given in EP 261 959, EP593 331, EP 674 689, EP 327 423, EP 512 889, EP 832 172; U.S. Patent Publication No. 2005/0223631; U.S. Pat. No.
  • the additive compositions according to the invention contain at least one cold resistance additive selected from ethylene/vinyl acetate copolymers (EVA) and/or ethylene/vinyl acetate/vinyl versatate terpolymers (VEOVA) and/or ethylene/vinyl acetate/acrylic ester (2-ethylhexyl acrylate) terpolymers as a cold resistance additive.
  • EVA ethylene/vinyl acetate copolymers
  • VEOVA ethylene/vinyl acetate/vinyl versatate terpolymers
  • ethylene/vinyl acetate/acrylic ester (2-ethylhexyl acrylate) terpolymers as a cold resistance additive.
  • the optional perfuming and/or odour-masking and/or reodorizing agent or agents can in particular be selected from the following aliphatic or cycloaliphatic esters:
  • the optional perfuming and/or odour-masking and/or reodorizing agent or agents can be selected from:
  • R1, R2, R3, which may be identical or different, are selected from hydrogen and hydrocarbon radicals comprising 1 to 10 carbon atoms and optionally having one or more heteroatoms as well as
  • biocide or biocides can be selected from:
  • oxazolidines 3,3′-methylene bis[5-methyloxazolidine] (CAS: 66204-44-2);
  • quaternary ammonium salts in the form of chlorides obtained from C12-C18 alkyl benzene or from alkyl dimethyl benzene.
  • the metal deactivator or deactivators or chelating agents can be selected from amines substituted with N,N′-disalicylidene groups, such as N,N′-disalicylidene 1,2-diaminopropane (MDA).
  • N,N′-disalicylidene 1,2-diaminopropane (MDA) N,N′-disalicylidene 1,2-diaminopropane
  • compositions according to the invention can have several functionalities, typically marker and perfuming agent: one component can be both a marker and a perfuming agent.
  • one component can be both a marker and a perfuming agent.
  • the additive compositions for fuels according to the invention can contain other additives such as those required by the regulations (markers, demulsifiers, anti-static additives or additives improving conductivity, lubricity additives, anti-wear agents and/or friction modifiers, combustion improving additives and in particular additives for improving the cetane index), anti-foaming additives etc.
  • the invention relates to a method of preparing the additive compositions as defined above, by mixing, preferably at room temperature, components a/ and b/ and optionally other additives and/or the solvent or solvents, co-solvents, in one or more steps by any suitable mixing means.
  • the invention relates to the use of at least one additive composition according to the invention incorporated in a fuel of the higher-grade diesel or biodiesel type for improving the lacquering resistance, i.e. fouling on the head and/or on the body of the needles of the fuel injection system but also in the whole needle lift control system (valves) of the injection system, in particular for engines equipped with fuel injection systems of the Euro 4 to Euro 6 type.
  • the invention also relates to a method of improving lacquering resistance, comprising the incorporation of an additive composition in a diesel or biodiesel fuel, said additive composition comprising:
  • the additive composition is as described in the several variants presented above.
  • the method of improving lacquering resistance according to the invention makes it possible to avoid and/or reduce and/or delay:
  • the invention further relates to higher-grade diesel or biodiesel fuels with improved lacquering resistance, with the addition of at least 50 ppm w/w of deposit reducer(s)/dispersants and at least one composition comprising at least one antioxidant of the hindered phenol type (alkylphenol) a/ and at least one metal passivator b/ selected from amines substituted with triazole groups.
  • concentration of additives a/ and b/ respectively in the final fuel with additives is between 2 and 200 ppm w/w and advantageously between 10 and 50 ppm w/w, i.e. ppmw relative to the total weight of the fuel with additives.
  • the composition of liquid fuel of the (bio)diesel type according to the invention comprises from 100 to 2000 ppm w/w and advantageously from 500 to 1500 ppm w/w of additive composition(s) according to the invention as defined above.
  • the diesel or biodiesel fuel according to the invention comprises:
  • ppm w/w from 2 to 200 ppm w/w, preferably from 10 to 100 ppm w/w, more preferably from 30 to 80 ppm w/w, advantageously from 10 to 50 ppm w/w, of antioxidant of the hindered phenol type a/, and
  • metal passivator b/ selected from amines substituted with triazole groups
  • At least 50 ppm w/w preferably from 50 to 1000 ppm w/w, advantageously from 50 to 500 ppm w/w, ideally from 50 to 250 ppm w/w of at least one conventional deposit reducer/dispersant.
  • additive composition(s) according to the invention in relation to the concentration of additives a/ and b/, which may for example depend on the viscosity of additives a/ and b/, and on that of any other additives; in the case when the additive composition according to the invention contains solvents or co-solvents, on the solubility of the additives in these solvents.
  • the optional other additives are generally incorporated in quantities in the range from 50 to 1500 ppm w/w, i.e. ppmw relative to the total weight of the fuel with additives.
  • diesel or biodiesel fuels mixtures based on liquid hydrocarbons having distillation temperatures comprised between 140 and 380° C., preferably between 180 and 360° C.; these mixtures are in general derived from cuts of the middle distillate type, originating from refineries and/or from agrofuels and/or from biofuels and/or from biomass and/or from synthetic fuels, and in particular from cuts rich in paraffins and isoparaffins, with a proportion of naphthenes, or also aromatic molecules such as those contained in gas oils resulting from the pyrolysis of biomass, preferably corresponding to the local specifications for diesel fuels, for example EN 590 in the European Union.
  • the (bio)diesel fuels incorporating at least one additive composition improving lacquering according to the invention can be prepared by doping the hydrocarbon mixture, with the additive composition or compositions according to the invention and with the optional other additive or additives, in one or more steps, generally at room temperature.
  • Additives a/ and b/ optionally the other additives, the solvent(s) and/or co-solvent(s)), with the (bio)diesel fuel, also falls within the scope of the invention.
  • the inventors have also developed a new method that is reliable and robust for evaluating the sensitivity of (bio)diesel fuels, in particular those of higher grade, to lacquering.
  • This method in contrast to the methods described in the publications cited above, is not a laboratory method but is based on real engine tests and is therefore of industrial interest and makes it possible to quantify the effectiveness of the additives or of the additive compositions against lacquering.
  • the method of measuring lacquering developed by the inventors is detailed below:
  • the engine used is a four-cylinder, 16-valve, high-pressure injection common rail diesel engine with a cylinder capacity of 1500 cm 3 and a power of 80 hp: regulation of the fuel injection pressure takes place in the high-pressure part of the pump.
  • the power point is 40 h at 4000 rpm; the position of the injector in the chamber has been lowered by 1 mm relative to its nominal position, which on the one hand promotes the release of thermal energy from combustion, and on the other hand brings the injector closer to the combustion chamber.
  • the flow rate of fuel injected is adjusted so as to obtain an exhaust temperature of 750° C. at the start of the test.
  • the injection advance was increased by 1.5° crankshaft relative to the nominal setting (changing from +12.5° to +14° crankshaft) still with the aim of increasing the thermal stresses to which the injector nozzle is subjected.
  • the injection pressure was increased by 10 MPa relative to the nominal pressure (i.e. changing from 140 MPa to 150 MPa) and the temperature is set at 65° C. at the inlet of the high-pressure pump.
  • the technology used for the injectors requires high fuel return, which promotes degradation of the fuel since it can be subjected to several cycles in the high-pressure pump and the common rail before being injected into the combustion chamber.
  • the smoke values allow the combustion timing to be monitored at the start of the test (target value 3FSN) and ensure that it is properly repeatable from one test to the next.
  • the injectors are dismantled at the end of the test in order to inspect and assess the deposits formed along the needles.
  • the scoring procedure adopted for assessing the needles is as follows:
  • the scale of scores varies from ⁇ 2.5 (for a heavy deposit) to 10 (for a new needle without any deposit).
  • the final score is a weighted average of the scores for all the needle surfaces assessed.
  • the fuels B0 (without VOME) and B7#1 and B7#2 are standard diesel fuels, complying with standard EN 590, and have a sulphur content less than or equal to 10 ppm. Unless stated otherwise, the quantities of the additives shown are expressed in ppm w/w: weight of additive in ppmw per total weight of fuel with additives.
  • the fuels H to L incorporating an additive composition according to the invention show good, or even excellent, lacquering resistance, in contrast to the comparative fuels with additives C to G.

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9340742B1 (en) 2015-05-05 2016-05-17 Afton Chemical Corporation Fuel additive for improved injector performance
WO2018077621A1 (en) 2016-10-25 2018-05-03 Chevron Oronite Technology B.V. Lubricating oil compositions comprising a biodiesel fuel and a dispersant
WO2018080789A1 (en) 2016-10-25 2018-05-03 Chevron Oronite Technology B.V. Lubricating oil compositions comprising a biodiesel fuel and a mannich condensation product
WO2021105268A1 (fr) * 2019-11-29 2021-06-03 Total Marketing Services Utilisation de composés alkyl phénol comme additifs de détergence pour essences
US11390821B2 (en) 2019-01-31 2022-07-19 Afton Chemical Corporation Fuel additive mixture providing rapid injector clean-up in high pressure gasoline engines
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US12134742B2 (en) 2022-09-30 2024-11-05 Afton Chemical Corporation Fuel composition

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8974551B1 (en) 2014-02-19 2015-03-10 Afton Chemical Corporation Fuel additive for improved performance in fuel injected engines
CN107815307B (zh) * 2017-10-26 2019-09-17 天津悦泰石化科技有限公司 一种燃料标识剂
EP3599297A1 (en) * 2018-07-25 2020-01-29 Nanuntio s.r.o. Composite system based on functionalized nanofibers for protection of active substances in lacquers
US12043808B2 (en) 2021-12-28 2024-07-23 Afton Chemical Corporation Quaternary ammonium salt combinations for injector cleanliness

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4810397A (en) * 1986-03-26 1989-03-07 Union Oil Company Of California Antifoulant additives for high temperature hydrocarbon processing
EP0482253A1 (en) * 1990-10-23 1992-04-29 Ethyl Petroleum Additives Limited Environmentally friendly fuel compositions and additives therefor
EP1887074A1 (en) * 2006-08-04 2008-02-13 Infineum International Limited Method and use for the prevention of fuel injector deposits
US20080127550A1 (en) * 2006-11-27 2008-06-05 Natalie Li Stabilized biodiesel fuel compositions
WO2009060057A2 (de) * 2007-11-09 2009-05-14 Basf Se Ether als wirkungsverbesserer für biozide
CN101768481A (zh) * 2008-12-29 2010-07-07 中国石油化工股份有限公司 一种柴油组合物
CN101768484A (zh) * 2008-12-26 2010-07-07 中国石油化工股份有限公司 一种柴油组合物
US20100293844A1 (en) * 2007-09-27 2010-11-25 Macmillan John Alexander Additives for Diesel Engines
WO2011006734A2 (en) * 2009-07-13 2011-01-20 L'air Liquide Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Additive mixture for the bactericidal and anticorrosive additization of fuels

Family Cites Families (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1248643B (de) 1959-03-30 1967-08-31 The Lubrizol Corporation, Cleveland, Ohio (V. St. A.) Verfahren zur Herstellung von öllöslichen aeylierten Aminen
US3329658A (en) 1962-05-14 1967-07-04 Monsanto Co Dispersency oil additives
US3574576A (en) 1965-08-23 1971-04-13 Chevron Res Distillate fuel compositions having a hydrocarbon substituted alkylene polyamine
US3702300A (en) 1968-12-20 1972-11-07 Lubrizol Corp Lubricant containing nitrogen-containing ester
FR2510598A1 (fr) 1981-07-30 1983-02-04 Inst Francais Du Petrole Utilisation d'additifs azotes comme agents d'abaissement du point de trouble des distillats moyens d'hydrocarbures et compositions de distillats moyens d'hydrocarbures renfermant lesdits additifs
FR2528066A1 (fr) 1982-06-04 1983-12-09 Inst Francais Du Petrole Additifs azotes utilisables comme agents d'abaissement du point de trouble des distillats moyens d'hydrocarbures et compositions de distillats moyens d'hydrocarbures renfermant lesdits additifs
FR2528051B1 (fr) 1982-06-08 1986-05-02 Inst Francais Du Petrole Additifs azotes utilisables comme agents d'abaissement du point de trouble des distillats moyens d'hydrocarbures et compositions de distillats moyens d'hydrocarbures renfermant lesdits additifs
FR2528423B1 (fr) 1982-06-10 1987-07-24 Inst Francais Du Petrole Additifs azotes utilisables comme agents d'abaissement du point de trouble des distillats moyens d'hydrocarbures et compositions de distillats moyens d'hydrocarbures renfermant lesdits additifs
FR2535723A1 (fr) 1982-11-09 1984-05-11 Inst Francais Du Petrole Additifs azotes utilisables comme agents d'abaissement du point de trouble des distillats moyens d'hydrocarbures et compositions de distillats moyens d'hydrocarbures renfermant lesdits additifs
FR2567536B1 (fr) 1984-07-10 1986-12-26 Inst Francais Du Petrole Compositions d'additifs destinees notamment a ameliorer les proprietes de filtrabilite a froid des distillats moyens de petrole
EP0261959B1 (en) 1986-09-24 1995-07-12 Exxon Chemical Patents Inc. Improved fuel additives
FR2607139B1 (fr) 1986-11-21 1989-08-18 Inst Francais Du Petrole Polymeres a fonctions azotees derives de polyesters insatures et leur utilisation comme additifs d'abaissement du point d'ecoulement des distillats moyens d'hydrocarbures
FR2613371B1 (fr) 1987-04-01 1989-07-07 Inst Francais Du Petrole Copolymeres azotes, leur preparation et leur utilisation comme additifs pour ameliorer les proprietes d'ecoulement des distillats moyens d'hydrocarbures
FR2626578B1 (fr) 1988-02-03 1992-02-21 Inst Francais Du Petrole Polymeres amino-substitues et leur utilisation comme additifs de modification des proprietes a froid de distillats moyens d'hydrocarbures
GB9104138D0 (en) 1991-02-27 1991-04-17 Exxon Chemical Patents Inc Polymeric additives
FR2676062B1 (fr) 1991-05-02 1993-08-20 Inst Francais Du Petrole Polymere amino-substitues et leur utilisation comme additifs de modification des proprietes a froid de distillats moyens d'hydrocarbures.
US5697988A (en) 1991-11-18 1997-12-16 Ethyl Corporation Fuel compositions
GB9200694D0 (en) 1992-01-14 1992-03-11 Exxon Chemical Patents Inc Additives and fuel compositions
DE69309842T2 (de) 1992-10-09 1997-10-16 Elf Antar France Aminephosphate mit einem Imid Endring, deren Herstellung, und deren Verwendung als Zusätze für Motorkraftstoffe
FR2699550B1 (fr) 1992-12-17 1995-01-27 Inst Francais Du Petrole Composition de distillat moyen de pétrole contenant des additifs azotés utilisables comme agents limitant la vitesse de sédimentation des paraffines.
FR2735494B1 (fr) 1995-06-13 1997-10-10 Elf Antar France Additif bifonctionnel de tenue a froid et composition de carburant
ES2183073T5 (es) 1997-01-07 2007-10-16 Clariant Produkte (Deutschland) Gmbh Mejoramiento de la fluidez de aceites minerales y destilados de aceites minerales mediando utilizacion de resinas de alquil-fenoles y aldehidos.
FR2839315B1 (fr) * 2002-05-03 2006-04-28 Totalfinaelf France Additif pour ameliorer la stabilite thermique de compositions d'hydrocarbures
US20050223631A1 (en) 2004-04-07 2005-10-13 Graham Jackson Fuel oil compositions
FR2869621B1 (fr) 2004-04-30 2008-10-17 Total France Sa Utilisation d'additifs pour ameliorer l'odeur de compositions d'hydrocarbures et compositions d'hydrocarbures comprenant de tels additifs
EP1884556A3 (en) 2006-08-04 2011-09-14 Infineum International Limited Diesel fuel compositions containing metallic species and detergent additives
EP2132285A2 (en) 2007-04-04 2009-12-16 The Lubrizol Corporation A synergistic combination of a hindered phenol and nitrogen containing detergent for biodiesel fuel to improve oxidative stability
SG183026A1 (en) * 2007-07-16 2012-08-30 Basf Se Synergistic mixture
GB0714725D0 (en) 2007-07-28 2007-09-05 Innospec Ltd Fuel oil compositions and additives therefor
CA2700497C (en) 2007-09-27 2016-08-09 Innospec Limited Diesel fuel compositions comprising low molecular weight-mannich product additives
US8623105B2 (en) 2008-05-13 2014-01-07 Afton Chemical Corporation Fuel additives to maintain optimum injector performance
FR2934276B1 (fr) * 2008-07-25 2012-12-21 Total France Additif pour combustible liquide, combustible liquide le contenant et son utilisation pour les appareils de production d'energie et/ou de chauffage et/ou de cuisson
GB0903165D0 (en) 2009-02-25 2009-04-08 Innospec Ltd Methods and uses relating to fuel compositions
CA2762069C (en) 2009-05-15 2018-03-20 The Lubrizol Corporation Quaternary ammonium amide and/or ester salts
CN102051239B (zh) * 2009-10-28 2013-11-06 中国石油化工股份有限公司 生物柴油组合物及提高生物柴油氧化安定性的方法
KR20130060205A (ko) 2010-04-27 2013-06-07 바스프 에스이 4급화 삼원중합체
FR2977895B1 (fr) * 2011-07-12 2015-04-10 Total Raffinage Marketing Compositions d'additifs ameliorant la stabilite et les performances moteur des gazoles non routiers

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4810397A (en) * 1986-03-26 1989-03-07 Union Oil Company Of California Antifoulant additives for high temperature hydrocarbon processing
EP0482253A1 (en) * 1990-10-23 1992-04-29 Ethyl Petroleum Additives Limited Environmentally friendly fuel compositions and additives therefor
EP1887074A1 (en) * 2006-08-04 2008-02-13 Infineum International Limited Method and use for the prevention of fuel injector deposits
US20080127550A1 (en) * 2006-11-27 2008-06-05 Natalie Li Stabilized biodiesel fuel compositions
US20100293844A1 (en) * 2007-09-27 2010-11-25 Macmillan John Alexander Additives for Diesel Engines
WO2009060057A2 (de) * 2007-11-09 2009-05-14 Basf Se Ether als wirkungsverbesserer für biozide
CN101768484A (zh) * 2008-12-26 2010-07-07 中国石油化工股份有限公司 一种柴油组合物
CN101768481A (zh) * 2008-12-29 2010-07-07 中国石油化工股份有限公司 一种柴油组合物
WO2011006734A2 (en) * 2009-07-13 2011-01-20 L'air Liquide Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Additive mixture for the bactericidal and anticorrosive additization of fuels
US8864853B2 (en) * 2009-07-13 2014-10-21 L'air Liquide Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Additive mixture for the bactericidal and anticorrosive additization of fuels

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
Proquest Machine Translation WP2009060057A2 (6/17/16 )(43 pps ) *
PROQUEST Machine Translation WP2009060057A2 (6/17/2016 - run 6/17/2016 43 pps)) *
Stabilization of Blended Diesel Fuel with Addtive Combinations by IA Bolubea EV Klinaeva, VN Koshlev VI kelarev and IA Goldsher Chemistry and Technology of Fuels and Oils Vol 33 No 1 1977pp23-26 *
Stabilization of Blended Diewsel Fuel with Additive Combinations by IA Bolube”a, EV Klinaeva, VN Koshlev, VI Kelarev and IA Goldsher Chemistry and Technology of Fuels and Oils Vol 33 No. 1 1977 pp 23-26 *

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* Cited by examiner, † Cited by third party
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US9340742B1 (en) 2015-05-05 2016-05-17 Afton Chemical Corporation Fuel additive for improved injector performance
WO2018077621A1 (en) 2016-10-25 2018-05-03 Chevron Oronite Technology B.V. Lubricating oil compositions comprising a biodiesel fuel and a dispersant
WO2018080789A1 (en) 2016-10-25 2018-05-03 Chevron Oronite Technology B.V. Lubricating oil compositions comprising a biodiesel fuel and a mannich condensation product
US10344245B2 (en) 2016-10-25 2019-07-09 Chevron Oronite Technology B.V. Lubricating oil compositions comprising a biodiesel fuel and a dispersant
US10781394B2 (en) 2016-10-25 2020-09-22 Chevron Oronite Technology B.V. Lubricating oil compositions comprising a biodiesel fuel and a Mannich condensation product
US11390821B2 (en) 2019-01-31 2022-07-19 Afton Chemical Corporation Fuel additive mixture providing rapid injector clean-up in high pressure gasoline engines
WO2021105268A1 (fr) * 2019-11-29 2021-06-03 Total Marketing Services Utilisation de composés alkyl phénol comme additifs de détergence pour essences
FR3103812A1 (fr) * 2019-11-29 2021-06-04 Total Marketing Services Utilisation de composés alkyl phénol comme additifs de détergence
US11873461B1 (en) 2022-09-22 2024-01-16 Afton Chemical Corporation Extreme pressure additives with improved copper corrosion
US12024686B2 (en) 2022-09-30 2024-07-02 Afton Chemical Corporation Gasoline additive composition for improved engine performance
US12134742B2 (en) 2022-09-30 2024-11-05 Afton Chemical Corporation Fuel composition
US11795412B1 (en) 2023-03-03 2023-10-24 Afton Chemical Corporation Lubricating composition for industrial gear fluids

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AR089385A1 (es) 2014-08-20
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PH12014501374A1 (en) 2014-09-22
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