EP0961820B1 - Additif d'onctuosite pour carburant - Google Patents

Additif d'onctuosite pour carburant Download PDF

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Publication number
EP0961820B1
EP0961820B1 EP98963589A EP98963589A EP0961820B1 EP 0961820 B1 EP0961820 B1 EP 0961820B1 EP 98963589 A EP98963589 A EP 98963589A EP 98963589 A EP98963589 A EP 98963589A EP 0961820 B1 EP0961820 B1 EP 0961820B1
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EP
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Prior art keywords
carbon atoms
acid
additive
chosen
formula
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.)
Revoked
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EP98963589A
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German (de)
English (en)
French (fr)
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EP0961820A1 (fr
Inventor
Danièle Eber
Laurent Germanaud
Paul Maldonado
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TotalEnergies Marketing Services SA
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Total France SA
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Priority claimed from FR9716538A external-priority patent/FR2772783A1/fr
Application filed by Total France SA filed Critical Total France SA
Priority to EP05000389A priority Critical patent/EP1522570A3/fr
Priority to DK98963589T priority patent/DK0961820T3/da
Publication of EP0961820A1 publication Critical patent/EP0961820A1/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols
    • 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
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/1802—Organic compounds containing oxygen natural products, e.g. waxes, extracts, fatty oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
    • C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • 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
    • 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
    • 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
    • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • 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
    • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • C10L1/233—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring containing nitrogen and oxygen in the ring, e.g. oxazoles
    • C10L1/2335—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring containing nitrogen and oxygen in the ring, e.g. oxazoles morpholino, and derivatives thereof
    • 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
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds

Definitions

  • the present invention relates to a fuel containing a lubricity additive to improve the properties lubricating fuels, whether it is engine fuel (diesel) or aviation fuel (jet fuel), and more particularly low-grade diesel fuels sulfur.
  • the gas oils have been added to anti-wear additives, known to some in the field of lubricants, of the type of fatty acid esters and dimers unsaturated fatty acids, aliphatic amines, esters of fatty acids and diethanolamine, and acids aliphatic monocarboxylic long chain as described in US Patents 2,527,889, US 4,185,594, US 4,204,481 and US 4208190.
  • anti-wear additives known to some in the field of lubricants, of the type of fatty acid esters and dimers unsaturated fatty acids, aliphatic amines, esters of fatty acids and diethanolamine, and acids aliphatic monocarboxylic long chain as described in US Patents 2,527,889, US 4,185,594, US 4,204,481 and US 4208190.
  • Most of these additives have power sufficient lubricant but at concentrations far too much high which is very economically unfavorable to purchase.
  • additives containing dimer acids can not be used in fuels fueling vehicles in which the fuel may be in contact with the lubricating oil, because these acids form by chemical reaction with detergents usually used in lubricants, deposits that can accelerate the wear process.
  • US Patent 4,609,376 advocates the use of anti-wear additives obtained from mono- and polycarboxylic and polyhydric alcohols in fuels containing alcohols in their composition.
  • Another chosen route is to introduce oils plants or their esters in fuels to improve their lubricity or lubricity.
  • oils plants or their esters can be found in rapeseed, flax, soybean, sunflower or their esters (see EP 635.558 and EP 605.857).
  • one of the major disadvantages of these esters is their low lubricity at a concentration of less than 0.5 % by weight in fuels.
  • EP-A-0 773 278 discloses compositions to improve the smoothness of fuels.
  • the present invention aims to solve the problems encountered with the additives proposed by the prior art, that is to say to improve the lubricating power of the fuels desulphurized and partially deflavored, while remaining compatible with other additives, including detergents, lubricating oils, in particular by not forming deposits and by reducing the cost price, in particular by less additive content, well below 0.5%.
  • the monoesters and di esters obtained from the oils are preferred. of the group consisting of lauric oils, from coconut or palm, rich in saturated alkyl chains of 12 to 14 carbon atoms, palmitic oils from palm, lard or tallow, containing a major amount of saturated alkyl chains.
  • linoleic oils derived from sunflower, maize or rapeseed containing a high content of linoleic acid
  • linolenic linseed oils comprising significant contents of tri-unsaturated alkyl chains containing from 1 to 18 carbon atoms
  • ricinoleic oils derived from castor oil derived from castor oil.
  • the preferred monoesters and diesters of glycerol obtained from polycyclic acids comprise an R 1 or R 3 and / or R 4 consisting of at least two rings each of 5 to 6 atoms of which at most one is optionally a heteroatom such as nitrogen or oxygen and the others are carbon atoms, these two rings having in addition two carbon atoms in common, preferably vicinal, said cycles being saturated or unsaturated .
  • They are preferably monoesters of glycerol of natural resin acids obtained from the distillation residues of natural oils extracted from coniferous trees, in particular coniferous conifers.
  • abietic acid acid esters are preferred. dihydroabietic, tetrahydroabietic acid, acid dehydroabietic, neoabietic acid, pimaric acid, of levopimaric acid and parastrinic acid.
  • Esters and amides of formula (II) can be easily obtained by reaction of an alcohol compound, amine and / or alkanolamine with an organic acid such as oleic acid or a simple ester such as methyl oleate operating in the conditions known per se by the man of the esterification and amidation processes.
  • the alcohols used to obtain the compound (II) are chosen from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, isobutanol, pentanol or else ethyl 2 hexanol, and / or oxyalkylated alcohols of formula R (O-CH 2 -CHR ') n -OH wherein R is an alkyl group of 1 to 6 carbon atoms, R' is hydrogen or an alkyl group of 1 to 4 carbon atoms and n an integer ranging from 1 to 5 such as methylcellosolve, butylcellosolve, butyldiglycol and 1-butoxy-propanol.
  • the primary amines or secondary compounds used to obtain the compound (II) are selected from the group consisting of methylamine, ethylamine, propylamine, butylamine, isobutylamine, ethyl-2-hexylamine, decylamine, dodecylamine, stearylamine and oleylamine, N, N-diethylamine, N, N-dipropylamine, N, N-dibutylamine, N, N-di (ethyl-2-hexyl) amine, methyldecylamine, N-methyldodecylamine, N-methyloleylamine.
  • alkanolamines selected from amines of 1 to 18 carbon atoms substituted by at least one hydroxyl, -hydroxymethyl, hydroxyethyl or hydroxypropyl such as ethanolamine, diethanolamine, triethanolamine, isopropanolamine, diisopropanolamine, triisopropanolamine, N-methylethanolamine, tris (hydroxymethyl) aminomethane, (N-hydroxyethyl) methylimidazoline, (N-hydroxyethyl) heptadecenylimidazoline.
  • hydroxyl, -hydroxymethyl, hydroxyethyl or hydroxypropyl such as ethanolamine, diethanolamine, triethanolamine, isopropanolamine, diisopropanolamine, triisopropanolamine, N-methylethanolamine, tris (hydroxymethyl) aminomethane, (N-hydroxyethyl) methylimidazoline, (N-hydroxyethyl) heptadecen
  • Additives obtained by physical mixing according to the invention are used to improve the lubricity Diesel fuels for land-based engines, possibly in mixture with at least one oxygenated compound selected from the group formed alcohols, ethers and esters, as well as with any additive used to improve fuel quality, such as as detergent, dispersant, antioxidant and antifoam or even biofuel.
  • a second object of the invention corresponds to fuels containing between 25 and 2500 ppm, and preferably 100 to 1000 ppm by weight of at least one additive used according to the invention dispersed in a diesel fuel defined by the ASTM D-975.
  • the purpose of this example is to compare the power lubricant additives lubricity according to the invention to that known lubricity additives with regard to wear in the conditions of the HFRR (High Frequency Reciprocating Rig) test as described by the standard procedure CEC-F06-A96 in SAE article 932692 by J. W. HADLEY of the University of Liverpool.
  • HFRR High Frequency Reciprocating Rig
  • the additives according to the invention will be referenced X i while the comparative additives will be referenced T i .
  • a first additive T 1 is the product of the reaction of oleic acid with diethanolamine. This reaction is carried out in a 500 ml tetracol flask into which 84.6 g of oleic acid and 105.3 g of xylene and then 31.5 g of diethanolamine are first introduced over a period of 10 minutes. The whole is then maintained under reflux of xylene for 6 hours to remove 6.4 ml of water. The final product obtained contains 50% of active ingredient, of yellow-orange color.
  • the infrared spectroscopic analysis shows absorption bands at 3500 cm -1 at 1730 cm -1 and 1650 cm -1, corresponding to the hydroxyl, ester and amide functions, respectively.
  • the second additive T 2 is the product of the reaction of a tall oil acid and diethanol amine.
  • the tall oil acid used is a combination of 70% of a mixture of fatty acids (55% oleic acid, 38% linoleic acid, 5% palmitic acid and 2% linolenic acid) and 30% % of resin acids, having an acid value of 185 mg KOH per gram.
  • the procedure is as for T 1 by introducing 80 g of tall oil acid, 28.2 g of diethanolamine and 98.6 g of xylene successively into the flask and maintaining a reflux of xylene for 6 hours.
  • the final reaction product is a yellow-orange, clear and viscous liquid having a residual acid number of 0.21 mg KOH per gram.
  • the third additive T 3 is a mixture of alkyl esters, mono, di and trialkyl esters, glycerol mainly comprising glycerol monooleate.
  • the first additive according to the invention X 1 is a physical mixture of 2 g of the additive T 2 and 1 g of the additive T 3 .
  • the second additive according to the invention X 2 is a physical mixture of 2 g of the additive T 1 and 1 g of the additive T 3 .
  • the additive T 4 is the glycerol trioleate sold by the company FLUKA.
  • the third additive according to the invention X 3 is the product of the reaction of glycerol trioleate T 4 with diethanolamine. Operation in a tetracol flask as for T 1 by mixing 80 g of glycerol trioleate and 18.5 g of diethanolamine, and then heating the whole at 150 ° C for 4 hours.
  • the additive T 5 is a soybean triglyceride oil with an average molecular weight of about 870, composed of 28% oleic acid, 50% linoleic acid, 8% linolenic acid, 3% stearic acid, 10% palmitic acid and 1% arachidic acid.
  • the fourth additive according to the invention X 4 is the product of the reaction of 87 g of T 4 with 21 g of diethanolamine, the mixture being stirred at 150 ° C. for 6 hours.
  • the additive X 4 is a fluid, yellow-orange liquid, having infrared spectroscopy absorption bands characteristic of alcohol, ester and amide functions.
  • the fifth additive according to the invention, X 5 is obtained under the same conditions as the additive X 4 , but using 87 g of T 4 and 15.75 g of diethanolamine.
  • the sixth additive according to the invention X 6 is obtained under the same conditions as the additive X 4 but using 27 g of the additive T 5 and 26 g of diethanolamine.
  • the seventh additive according to the invention, X 7 is obtained under the same conditions as the additive X 4 but replacing the diethanolamine with 24 g of tris (hydroxymethyl) aminomethane.
  • the eighth additive according to the invention X 8 is obtained under the same conditions as the additive X 4 , but using as triglyceride castor oil, with an average molecular weight of about 927, composed of 87% of ricinoleic acid, 7% oleic acid and 3% stearic acid.
  • the gas oils A, B and C thus additivated were subjected to the HFRR test, which consists of imposing, together with a steel ball in contact with a stationary metal plate, a pressure corresponding to a weight of 200 g and an alternating displacement of 1 mm. at a frequency of 50Hz.
  • the ball in motion is lubricated by the test composition.
  • the temperature is maintained at 60 ° C throughout the duration of the test, ie 75mn.
  • the lubricating power is expressed by the average value of the diameters of the wear impression of the ball on the plate.
  • a small wear diameter indicates good lubricity; conversely, a large wear diameter reflects a power all the more insufficient that the wear diameter is high.
  • X 1 and X 2 have lower wear characteristics, which are therefore much better than those of T 1 , T 2 and T 3 , which reflects the synergistic effect of lubricity according to the invention.
  • X 3 corresponds to the reaction product obtained according to the process of the invention, diethanolamine on glycerol trioleate. It is noted as before the interest of the additive thus obtained with regard to the wear characteristics obtained by T 4 .

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Combustion & Propulsion (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)
  • Lubricants (AREA)
EP98963589A 1997-12-24 1998-12-22 Additif d'onctuosite pour carburant Revoked EP0961820B1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP05000389A EP1522570A3 (fr) 1997-12-24 1998-12-22 Additif d'onctuosite pour carburant
DK98963589T DK0961820T3 (da) 1997-12-24 1998-12-22 Olieagtigt tilsætningsstof til motorbrændstof

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
FR9716538 1997-12-24
FR9716538A FR2772783A1 (fr) 1997-12-24 1997-12-24 Additif d'onctuosite pour carburant
FR9803225A FR2772784B1 (fr) 1997-12-24 1998-03-17 Additif d'onctuosite pour carburant
FR9803225 1998-03-17
PCT/FR1998/002823 WO1999033938A1 (fr) 1997-12-24 1998-12-22 Additif d'onctuosite pour carburant

Related Child Applications (1)

Application Number Title Priority Date Filing Date
EP05000389A Division EP1522570A3 (fr) 1997-12-24 1998-12-22 Additif d'onctuosite pour carburant

Publications (2)

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EP0961820A1 EP0961820A1 (fr) 1999-12-08
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EP98963589A Revoked EP0961820B1 (fr) 1997-12-24 1998-12-22 Additif d'onctuosite pour carburant
EP05000389A Withdrawn EP1522570A3 (fr) 1997-12-24 1998-12-22 Additif d'onctuosite pour carburant

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EP (2) EP0961820B1 (id)
JP (1) JP3226497B2 (id)
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AR (1) AR014163A1 (id)
AT (1) ATE290057T1 (id)
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CA (1) CA2281635C (id)
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Publication number Publication date
ES2242310T3 (es) 2005-11-01
CA2281635C (fr) 2009-02-17
CA2281635A1 (fr) 1999-07-08
WO1999033938A1 (fr) 1999-07-08
US6511520B1 (en) 2003-01-28
PL335330A1 (en) 2000-04-25
EP1522570A3 (fr) 2005-11-30
RU2167919C1 (ru) 2001-05-27
HU222537B1 (hu) 2003-08-28
KR20000071202A (ko) 2000-11-25
DE69829167D1 (de) 2005-04-07
HUP0001251A2 (hu) 2000-08-28
PT961820E (pt) 2005-07-29
PL189103B1 (pl) 2005-06-30
EP1522570A2 (fr) 2005-04-13
MY121333A (en) 2006-01-28
FR2772784A1 (fr) 1999-06-25
AR014163A1 (es) 2001-02-07
FR2772784B1 (fr) 2004-09-10
NO994055D0 (no) 1999-08-23
ID23178A (id) 2000-03-23
EP0961820A1 (fr) 1999-12-08
JP3226497B2 (ja) 2001-11-05
KR100598227B1 (ko) 2006-07-07
NO994055L (no) 1999-10-20
JPH11209766A (ja) 1999-08-03
ATE290057T1 (de) 2005-03-15
DE69829167T2 (de) 2006-04-13
HUP0001251A3 (en) 2001-02-28
BR9807728B1 (pt) 2010-05-18
BR9807728A (pt) 2000-02-15

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