FR2772783A1 - New additives compositions for improving the lubricating power of low sulfur petrol, diesel and jet fuels - Google Patents

New additives compositions for improving the lubricating power of low sulfur petrol, diesel and jet fuels Download PDF

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FR2772783A1
FR2772783A1 FR9716538A FR9716538A FR2772783A1 FR 2772783 A1 FR2772783 A1 FR 2772783A1 FR 9716538 A FR9716538 A FR 9716538A FR 9716538 A FR9716538 A FR 9716538A FR 2772783 A1 FR2772783 A1 FR 2772783A1
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Daniele Eber
Laurent Germanaud
Paul Maldonado
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Elf Antar France
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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L10/00Use of additives to fuels or fires for particular purposes
    • C10L10/08Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
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    • C10L1/19Esters ester radical containing compounds; ester ethers; carbonic acid esters
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/19Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • C10L1/191Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/222Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224Amides; Imides carboxylic acid amides, imides
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/1802Organic compounds containing oxygen natural products, e.g. waxes, extracts, fatty oils
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/192Macromolecular compounds
    • C10L1/198Macromolecular 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
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    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/192Macromolecular compounds
    • C10L1/198Macromolecular 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
    • C10L1/1985Macromolecular 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
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/222Organic 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
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/232Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
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    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/232Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • C10L1/233Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring containing nitrogen and oxygen in the ring, e.g. oxazoles
    • C10L1/2335Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring containing nitrogen and oxygen in the ring, e.g. oxazoles morpholino, and derivatives thereof
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    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/234Macromolecular compounds
    • C10L1/238Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds

Abstract

<P> Productivity additive for motor fuels, in particular with a low sulfur content of less than or equal to 500 ppm, composed mainly of a combination comprising from 5 to 95% by weight of a glycerol monoester R1 -C (O ) -O-CH 2 -CHOHC-CH 2 OH or R 1 -C (O) -O-CH (CH 2 OH) 2 R 1 being an alkyl chain comprising from 8 to 24 carbon atoms, or a mono or polycyclic group comprising from 8 to 60 carbon atoms, and from 5 to 95% by weight of a compound of formula R2 -C (O) -X, R2 being an alkyl chain comprising from 8 to 24 carbon atoms, or a mono or polycyclic group comprising from 8 to 60 carbon atoms, and X being selected from the group consisting of mono and polyalcohols ester functions comprising from 1 to 8 carbon atoms, the primary amines, secondary amines, alkanolamines and aliphatic carbon chain polyamines, comprising from 1 to at 18 carbon atoms. </ P>

Description

 The present invention relates to a fuel containing a lubricity additive to improve the lubricating properties of fuels, whether it is ground motor fuel (gasoline or diesel) or aviation fuel (jet fuel), and more particularly diesel fuels. low sulfur content.

 It is well known that diesel fuels and aviation fuels must have lubrication capabilities for the protection of pumps, injection systems and all moving parts with which these products come into contact in an internal combustion engine. . With the desire to use more and more pure and non-polluting products, especially those without sulfur, the refining industry has been led to improve its sulfur compound removal treatment processes. However, it has been observed that by losing the sulfur compounds, the aromatic and polar compounds often associated with them are also lost, which causes a loss of the lubricating power of these fuels. Thus, below certain levels, the removal of sulfur compounds in the composition of these products very substantially promotes the phenomena of wear and rupture of moving parts at pumps and injection systems. As many countries have imposed the requirement to limit the acceptable upper sulfur content in fuels to 0.05% by weight to reduce emissions of cars, trucks or buses from polluting combustion gases, particularly in urban areas, it is it is necessary to replace these lubricant compounds with other non-polluting compounds with regard to the environment but having sufficient lubricating power to avoid the risk of wear.

 It is also mentioned in the literature that low-sulfur gasoline fuels have a lubricating power that may be insufficient to ensure good lubrication of the injection systems of new vehicles and may result in premature wear risk.

 To solve this problem, several types of additives have already been proposed. Thus, anti-wear additives, known for certain in the field of lubricants, of the type of fatty acid esters and unsaturated dimer fatty acids, aliphatic amines, esters of fatty acids and of diethanolamine, and long-chain aliphatic monocarboxylic acids as described in US Patents 2,252,889, US 4,185,594, US 4,204,481, US 4,208,190, US 4,428,182. Most of these additives have sufficient lubricity but at concentrations far too high which is very economically unfavorable to purchase. In addition, additives containing dimer acids, such as those containing trimeric acids, can not be used in fuels supplying vehicles in which the fuel can 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.

 No. 4,609,376 recommends the use of anti-wear additives obtained from esters of polycarboxylic monoet acids and polyhydroxy alcohols in fuels containing alcohols in their composition.

 In patent GB 2,307,246, the product resulting from the reaction of a carboxylic acid of 10 to 60 carbon atoms chosen from fatty acids or fatty acid dimers with an alkanolamine obtained by condensation of an amine or amine. A polyamine with an alkylene oxide is preferred to them as an additive of onctusity.

 In GB 2,307,247, it is preferred to use an acid derivative substituted with at least one hydroxyl group or a polyol ester derivative or an amide of this acid.

Another chosen route is to introduce vegetable oils or their esters into the fuels to improve their lubricity or lubricity. Among these are rapeseed, flax, soya, sunflower or their esters (see EP 635.558 and EP 605.857)
However, one of the major drawbacks of these esters is their low lubricating power at a concentration of less than 0.5 W by weight in 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 lubricity of desulfurized fuels and deflavored, while remaining compatible with other additives, including detergents, and lubricating oils, in particular by not forming a deposit and by reducing the cost of the additive, in particular by a lower additive content, substantially less than 0.5 W.

The subject of the present invention is a lubricity additive for improving the lubricating power of motor fuels, in particular fuels with a low sulfur content, that is to say less than or equal to 500 ppm, characterized in that it is compound consisting mainly of a combination comprising from 5 to 95 W by weight of at least one glycerol monoester of formula (IA) or (1B) below

Figure img00030001

with R1 chosen from linear or weakly branched, saturated or unsaturated alkyl chains containing from 8 to 24 carbon atoms, and cyclic and polycyclic groups comprising from 8 to 60 carbon atoms,
and from 5 to 95 W by weight of a compound of formula II below

Figure img00030002

wherein R2 is a straight or weakly branched, saturated or unsaturated alkyl chain comprising from 8 to 24 carbon atoms or a cyclic or polycyclic group comprising from 8 to 60 carbon atoms, and X is selected from the group consisting of esters of monoalcohol and linear or branched polyalcohols comprising from 1 to 8 carbon atoms, and linear or branched aliphatic, linear or branched, aliphatic carbon chain primary amine functional groups containing from 1 to 18 carbon atoms.

 In a preferred embodiment of the invention, the additive will comprise at least 70% by weight of said combination which will preferably contain from 10 to 40% by weight of at least one compound of formula (IA) and / or (zig) and from 60 to 90% of at least one compound of formula (II).

The additive according to the invention advantageously comprises up to 30% by weight of at least one glycerol diester of formulas (IIIA) and / or (IIIB)

Figure img00040001

in which R3 and R4, which are identical or different, are chosen from linear or weakly branched, saturated or unsaturated alkyl chains comprising from 8 to 24 carbon atoms, and cyclic and polycyclic groups comprising from 8 to 60 carbon atoms,
and preferably from 5 to 20% by weight of this glycerol diester.

 Among the glycerol monoesters of formula (I) with R 1 consisting of an alkyl chain, the monoesters of the group consisting of lauric oils, derived from coconut or palm, rich in saturated alkyl chains of 12 to 14 carbon atoms, are preferred. palmitic oils derived from palm, lard or tallow, containing a major quantity of saturated alkyl chains containing 16 carbon atoms, 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, and ricinoleic oils derived from castor oil.

Among the glycerol monoesters obtained from polycyclic acids, the preferred monoesters comprise a
R1 consists of at least two rings each consisting 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. These are preferably glycerol monoesters of natural resin acids obtained from the distillation residues of natural oils extracted from coniferous trees, in particular coniferous conifers, as well as the alkali metal and alkaline earth metal carboxylates, the amine carboxylates and the amides.

 Among these resinous acid esters according to the invention, the esters of abietic acid, dihydroabietic acid, tetrahydroabietic acid, dehydroabietic acid, neoabietic acid, pimaric acid and levopimaric acid are preferred. and parastrinic acid.

 By adjusting the partial hydrolysis operating conditions of these oils, it is possible to directly obtain the mixture of monoalkyl esters / dialkyl esters of glycerol.

 According to another embodiment of the invention, it is possible to prepare the glycerol alkyl esters by esterification reaction between the carboxylic acids described above and glycerol.

 The esters and amides of formula (II) can be easily obtained by reacting an alcohol or a polyol, an amine or a polyamine with an organic acid such as oleic acid or a simple ester such as methyl oleate operating under the conditions known per se by those skilled in the art, esterification and amidation processes.

The subject of the present invention is also a process for preparing said additive, characterized in that it is obtained by reaction in a molar ratio ranging from 0.1 to 3 of at least one compound from the group consisting of monoalcohols, polyalcohols, alkanolamines, primary and secondary amines and polyamines comprising from 1 to 18 carbon atoms on a triglyceride of formula (Iv) below

Figure img00060001

 in which R'1, R'2 and R'3 are identical or different and correspond to groups chosen from linear or weakly branched, saturated or unsaturated alkyl chains comprising from 8 to 24 carbon atoms, the reaction being carried out at a temperature between room temperature and 2500C, preferably between 80 and 2000C, for a period of between 0.5 and 10 hours, preferably between 2 and 4 hours at atmospheric pressure.

 Depending on the case, it may be useful to operate in an aromatic solvent at a content between 25 and 75 W by weight of the reagents used in the process of the invention, this solvent being selected from xylenes, ethylbenzene and commercial hydrocarbon cuts for example those distilling between 190 and 2090C and containing 99% by weight of aromatic compounds.

 For the process employing an alcohol or a polyol, it is advantageous to operate in the presence of a catalyst chosen from mineral acids such as sulfuric acid or acetic acid or hydrochloric acid, and organic acids. such as methanesulfonic acid, trifluoromethanesulfonic acid or para-toluenesulphonic acid, the catalyst content not exceeding 5% by weight of the reactants used. One can still operate in the presence of ion exchange resins and metal derivatives such as tetrabutyl tin.

 Advantageously from 0.5 to 2.8 moles, and preferably from 1.5 to 2.5 moles of an alcohol, polyol, amine, polyamine or alkanolamine compound per mole of triglyceride will be used.

 As starting triglycerides in the process which is the subject of the invention, triglycerides of monocarboxylic fatty acids comprising from 8 to 24 carbon atoms, which may be chosen for example from 2-ethylhexanoic acid, lauric acid, are preferred. , myristic acid, hexadecanoic acid, palmlitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, nonadecanoic acid, arachidic acid, behenic acid or erucic acid and ricinoleic acid.

 Since these triglycerides are mainly present in vegetable oils and animal oils, it is easy to understand the technical and commercial advantage that can be represented by a lubricity additive prepared from these readily available oils on the market on which compounds are also reacted. easily available and therefore relatively inexpensive.

 Of the vegetable and animal oils comprising these triglycerides, the vegetable oils of the group consisting of corn, rapeseed, sunflower, soybean and castor oil are preferred.

 In a first embodiment of the preparation process, at least one alcohol chosen from alkanols, including methanol, ethanol, propanol, isopropanol, butanol, isobutanol, pentanol and the like, is reacted with triglycerides. still 2-ethyl hexanol, and / or oxyalkylated alcohols of formula R (O-CH 2 -CHR ') n-OH in which R is an alkyl group of 1 to 6 carbon atoms, R' an alkyl group of 1 to 4 carbon atoms and n an integer ranging from 1 to 5 such as methylcellosolve, butylcellosolve and butyldiglycol.

 In a second embodiment, the polyols of the group preferably consisting of ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, arabitol, sorbitol, mannitol, trimethylolpropane or trimethylolhexane are controlled on the triglycerides. , pentaerythritol, 1,2-butanediol, 2,4-hexanediol, pinacol, 1,2-cyclohexanediol.

In a third embodiment, primary or secondary amines selected from the group consisting of methylamine, ethylamine, propylamine, butylamine, isobutylamine, ethyl-2-hexylamine, hexamethylamine, propylamine and amine are selected from the triglycerides. decylamine, dodecylamine, stearylamine and oleylamine, N, N-diethylamine, N, N-dipropylamine, N, N-dibutylamine, N, N-di (2-ethyl) hexylamine, methyldecylamine, N-methyldodecylamine, the
N-méthyloléylamine.

The polyamines used according to a fourth mode according to the invention are chosen from compounds having from 2 to 8 carbon atoms per amino chain and from 2 to 5 nitrogen atoms, the preferred polyamines being ethylenediamine, propylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, N (aminoethyl) morpholine, N- (aminopropyl) morpholine, N (aminoethyl) piperazine, N-methylpropanediamine or else
N- (butyl) propanediamine, and the polymers resulting from the hydrogenation of fatty amine adducts of 8 to 18 carbon atoms with acrylonitrile such as N-oleylpropane diamine.

 In a fifth embodiment of the invention, the alkanolamines are chosen from amines of 1 to 18 carbon atoms substituted with at least one hydroxymethyl, hydroxyethyl or hydroxypropyl group such as ethanolamine, diethanolamine, triethanolamine, isopropanolamine, diisopropanolamine, triisopropanolamine, N-methylethanolamine, N-hydroxyethylethylenediamine, tris (hydroxymethyl) aminomethane, N-hydroxyethylmethylimidazoline, N-hydroxyethylheptadecenylimidazoline.

In a preferred embodiment of the invention, the preparation process according to the invention results in a mixture of compounds comprising
from 5 to 25% by weight of at least one monoester of
glycerol of formulas (IA) and or (1B) hereinafter

Figure img00080001

with R1 chosen from linear or weakly branched, saturated or unsaturated alkyl chains containing from 8 to 24 carbon atoms,
from 35 to 75 W by weight of at least one compound of
formula (II) below
Figure img00090001

in which R2 is a linear or weakly branched, saturated or unsaturated alkyl chain comprising from 8 to 24 carbon atoms, and X is chosen from the group consisting of monoalcohol esters and polyalcohols linear or branched comprising from 1 to 8 atoms of carbon, and primary, secondary amine functional groups, alkanolamines and polyamines of aliphatic carbon chain, linear or branched, comprising from 1 to 18 carbon atoms,
from 0.1 to 20 W by weight of at least one diester of
glycerol of formula (IIIA) and / or (IIIB)
Figure img00090002

in which R3 and R4, identical or different,
are chosen from linear alkyl chains or
weakly branched, saturated or unsaturated,
comprising from 8 to 24 carbon atoms,
and optionally a residue of at least one triglyceride
of formula (IV) unreacted.

 The additives obtained by physical mixing or as reaction products according to the invention are used to improve the lubricity of hydrocarbon ground motor fuels, optionally mixed with at least one oxygenated compound selected from the group consisting of alcohols, ethers and esters.

A third subject of the invention are the fuels containing between 25 and 2500 ppm, and preferably from 100 to 1000 ppm by weight of at least one additive according to the invention consisting of the species defined by the ASTM D-439 standard containing optionally at least one oxygenated compound for supplying spark ignition engines and fuels
Diesel defined by the standard ASTM D-975, intended to supply diesel engines.

 The examples below are given as an illustration of the invention but not limiting its scope.

EXAMPLE I
The purpose of the present example is to compare the lubricating power of the lubricity additives according to the invention with that of the lubricity additives known from the point of view of wear under the conditions of the HFRR test (High Frequency Reciprocating Rig) as described. in SAE 932692 by JW HADLEY of the University of Liverpool.

 The additives according to the invention will be referenced X while the comparative additives will be referenced Ti.

 A first additive T1 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 are first introduced, followed by 31.5 g of diethanolamine 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 aborption bands at 3500 cm -1, 1730 cm -1 and 1650 cm -1, corresponding to the hydroxyl, ester and amide functions, respectively.

 The second additive T2 is the product of the reaction of tall oil acid and diethanolamine. Talloil acid used is a combination of 70 W of a mixture of fatty acids (55 W oleic acid, 38% linoleic acid, 5% palmitic acid and 2 W linoleic acid) and 30% d resin acids having an acid value of 185 mg KOH per gram. The procedure is as for T1 introducing 80 g of tall oil acid, 28.2 g of diethanolamine and 98.6 g of xylene successively in the flask refluxing xylene for 6 hours. The final reaction product is a clear, yellow, orange-yellow liquid having a residual acid number of 0.21 mg KOH per gram.

 The third additive T3 is a mixture of alkyl esters, mono, di and trialkyl esters, glycerol comprising mainly glycerol monooleate.

 The first additive according to the invention X1 is a physical mixture of 2 g of the additive T2 and 1 g of the additive T3.

 The second additive according to the invention X2 is a physical mixture of 2 g of the additive T1 and 1 g of the additive T3.

 The additive T4 is the glycerol trioleate sold by the company FLUKA.

 The third additive according to the invention X3 is the product of the reaction of the glycerol trioleate T4 with diethanolamine. It operates in a tetracol balloon as for T1 by mixing 80 g of glycerol trioleate and 18.5 g of diethanolamine, and then heating all at 1500C for 4 hours.

 The T5 additive is a soybean triglyceride oil with an average molecular weight of about 870, composed of 28 W oleic acid, 50% linoleic acid, 8 W linolenic acid, 3 W stearic acid, 10 % palmitic acid and 1 W arachidic acid.

 The fourth additive according to the invention X4 is the product of the reaction of 87 g of T4 with 21 g of diethanolamine, the mixture being stirred at 1500 ° C. for 6 hours. The X4 additive is a fluid, yellow-orange liquid, exhibiting infrared spectrometry characteristic absorption bands of alcohol, ester and amide functions.

 The fifth additive according to the invention, X5, is obtained under the same conditions as the additive X4, but using 87 g of T4 and 15.75 g of diethanolamine.

 The sixth additive according to the invention X6 is obtained under the same conditions as the additive X4 but using 27 g of the additive T5 and 26 g of diethanolamine.

 The seventh additive according to the invention, X7, is obtained under the same conditions as the additive X4 but replacing the diethanolamine with 24 g of tris- (hydroxymethyl) aminomethane.

 The eighth additive according to the invention X8 is the product of the reaction of a sunflower triglyceride oil, with an average molecular weight of about 880, composed of 6.5 k of palmitic acid, 3.8 w of stearic acid, 28 wt. % of oleic acid, and 60% of linoleic acid, with diethylenetriamine. At 88 g of this oil, 20.6 g of diethylenetriamine and 99 g of xylene are successively added. The whole is heated to xylene reflux for 3 hours 30 minutes. The final product obtained is pasty in appearance and light brown in color.

The ninth additive according to the invention Xg is the product of the reaction of a rapeseed oil of triglyceride oil, of average molecular weight of about 972, composed of 4, 8k of palmitic acid, 1.5% of stearic acid, 60.5% oleic acid, 21.5% linoleic acid and 7.6% linolenic acid with dihydroxymethyl-2,2-propanol. 97 g of this oil are added successively 37 g of dihydroxymethyl-2,2-propanol, 115 g of xylene and 0.5 g of para-toluenesulfonic acid. The whole is heated to xylene reflux for 24 hours. The final product obtained is a viscous liquid of dark color presenting in infrared spectroscopy the adsorption bands of the functions -i -i alcohol and ester, respectively at 3500 cm and 1730 cm.
The tenth additive according to the invention X10 is obtained under the same conditions as the additive X4, but using as triglyceride castor oil, with an average molecular weight of about 927 composed of 87% of ricinoleic acid, 7% of oleic acid and 3% of stearic acid.

 Each of the additives described above are introduced into three different gas oils, A, B and C whose characteristics are given in Table I below, at a content of 100 ppm of active ingredient.

TABLE I

Figure img00130001

<tb><SEP> Gas Oil <SEP> A <SEP> Gas Oil <SEP> B <SEP> Gas Oil <SEP> C
<tb> Distillation <SEP> (NFM <SEP> 07-022)
<tb> Initial <SEP> Point <SEP> 183 <SEP> 165 <SEP> 168.5
<tb> Point <SEP> to <SEP> 10% <SEP> volume <SEP> 227 <SEP> 208.5 <SEP> 208
<tb><SEP> 20% <SEP> volume <SEP> 247 <SEP> 227.5 <SEP> 226
<tb><SEP> 50% <SEP> volume <SEP> 290 <SEP> 276 <SEP> 274.5
<tb><SEP> 80% <SEP> volume <SEP> 334 <SEP> 317.5 <SEP> 317
<tb><SEP> 90% <SEP> volume <SEP> 354 <SEP> 334 <SEP> 336
<tb> Point <SEP> final <SEP> 373 <SEP> 357.5 <SEP> 364
<tb> Mass <SEP> volume <SEP> to <SEP> 15 <SEP> OC <SEP> 0.8508 <SEP> 0.8360 <SEQ> 0.8364
<tb><SEP> (NFT <SEP> 60-172)
<tb><SEP><SEP> Cetane <SEP> Index <calculated>SEP> 51.3 <SEP> 50 <SEP> 53
<tb><SEP> (ASTM <SEP> D4737)
<tb> W <SEP> sulfur <SEP> (ppm) <SEP> 480 <SEP> 270 <SEP> 455
<tb> Power <SEP> Lubricant <SEP> HFRR <SEP> 425 <SEP> 772 <SEP> 550
<tb><SEP> (CEC <SEP> F06A96) <SEP> (pm) <SEP>
<Tb>
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 600C for 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.

TABLE II

Figure img00140001

<tb><SEP> GAS <SEP> 1 <SEP> GAS <SEP> 2 <SEP> GAS <SEP> 3
<tb> ADDITIVES <SEP> Diameter <SEP> Gain <SEP> (%) <SEP> Diameter <SEP> Gain <SEP> (%) <SEP> Diameter <SEP> Gain <SEP> (%)
<tb><SEP> wear <SEP> wear <SEP> wear
<tb><SEP> (m) <SEP> (m) <SEP> (,)
<tb><SEP> without <SEP> 425 <SEP> 712 <SEP> 550
<tb><SEP> additive
<tb><SEP> T1 <SEP> 335 <SEP><SEP> 21 <SEP> 618 <SEP> 20 <SEP> 456 <SEP> 17
<tb><SEP> T2 <SEP> 320 <SEP> 25 <SEP> 695 <SEP> 10 <SEP> 470 <SEP> 15
<tb><SEP> 360 <SEP> 15 <SEP> 633 <SEP> 18 <SEP> 430 <SEP> 22
<tb> T3
<tb><SEP> 301 <SEP> 29 <SEP> 525 <SEP> 32 <SEP> 396 <SEP> 28
<tb><SEP> X1
<tb><SEP> 299 <SEP> 30 <SEP> 553 <SEP> 28 <SEQ> 439 <SEP> 20
<tb><SEP> T4 <SEP> 420 <SEP> 1 <SEP> 820 <SEP> -6 <SEP>
<SEP> X3 <SEP> 304 <SEP> 28 <SEP> 526 <SEP> 32 <SEP> 435 <SEP> 21
<tb><SEP> T5 <SEP> 410 <SEP> 4 <SEP> 750 <SEP> 3 <SEP> 545
<tb><SEP> X4 <SEP> 291 <SEP> 32 <SEP> 501 <SEP> 35 <SEP> 405 <SEP> 26
<tb><SEP> X5 <SEP> 308 <SEP> 28 <SEP> - <SEP> 442 <SEP> 20
<tb><SEP> 258 <SEP> 39 <SEP> 562 <SEP> 27 <SEP> 409 <SEP> 26
<tb><SEP> X7 <SEP> 331 <SEP> 22 <SEP> 444 <SEP> 42 <SEP> 440 <SEP> 20
<tb><SEP> X8 <SEP> 330 <SEP> 22 <SEP> 555 <SEP> 28 <SE> 446 <SEP> 19
<tb><SEP> X9 <SEP> 360 <SEP> 15 <SEP> 681 <SEP> 12 <SEP> 433 <SEP> 21
<tb><SEP> X10 <SEP> 300 <SEP> 30 <SEP> 526 <SEP> 32 <SEP> 404 <SEP> 26
<Tb>
It can be seen from Table II that the physical mixtures according to the invention, such as 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 obtained by combination of the majority components of the lubricity additive 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 respect to the wear characteristics obtained by T4.

 The performance of the additives X4, Xg, X6 and X7 are to be compared with those of the starting oil Tg. As previously, the combination of the reaction products limits the wear phenomena observed in the case of the oil alone.

Claims (6)

    pF.VFNr) T CTTONS 1. Additive lubricity for motor fuels, especially low sulfur content less than or equal to 500 ppm, characterized in that it is composed mainly of a combination comprising from 5 to 95 W in weight of a glycerol monoester of formula IA or IB following with R1 chosen from linear or weakly branched, saturated or unsaturated alkyl chains comprising from 8 to 24 carbon atoms, and cyclic and polycyclic groups comprising from 8 to 60 atoms of carbon, and 5 to 95 W by weight of a compound of formula II below wherein R2 is a linear or weakly branched, saturated or unsaturated alkyl chain comprising from 8 to
  1.  24 carbon atoms, or a cyclic group or
     polycyclic comprising from 8 to 60 carbon atoms, and X
     is selected from the group consisting of the functions
     esters of monoalcohol and linear polyalcohols or
     branched from 1 to 8 carbon atoms, and
     primary amines, secondary functions, alkanolamines and
     aliphatic carbon chain polyamines, linear or
     branched, comprising from 1 to 18 carbon atoms.
    2. Additive according to claim 1 characterized in that
     comprises at least 70 W by weight of said combination
     which consists of 10 to 40 W by weight of at least one
     glycerol monoester of formula (IA) and / or (zig) and from 60 to
     90% of at least one compound of formula (II).
    3. Additive according to one of claims 1 or 2 characterized
     in that it contains at most 30% by weight of at least one
     glycerol diester of formulas (IIIA) and / or (IIIB)
    Figure img00170001
     in which R3 and R4 are identical or different and are chosen from linear or weakly branched, saturated or unsaturated alkyl chains comprising from 8 to 24 carbon atoms, and cyclic and polycyclic groups comprising from 8 to 60 carbon atoms, and preferably 5 to 20 wt.% of said glycerol diester.
    4. Additive according to one of claims 1 to 3 characterized in
     what the glycerol monoesters of formula (I) with R1
     consisting of an alkyl chain are selected from the group
     consisting of lauric oils derived from copra or
     palm, rich in saturated alkyl chains of 12 to 14 atoms
     palmitic oils from palm,
     lard or tallow, containing a major amount of
     saturated alkyl chains with 16 carbon atoms, the oils
     linoleum from sunflower, maize or rapeseed,
     containing a high content of linoleic acid, the oils
     linolenic linseed, including significant levels of
     tri-unsaturated alkyl chains of 1 to 18 carbon atoms,
     and ricinoleic oils derived from castor oil.
    5. Additive according to one of claims 1 to 3 characterized in
     what the glycerol monoesters of formula (I) are
     obtained by reacting glycerol with acids
     polycyclic compounds comprising at least two cycles each formed
     from 5 to 6 atoms of which at most one is possibly a
     heteroatom such as nitrogen or oxygen and the others are
     carbon atoms, these two cycles having in addition two
     carbon atoms in common, preferably vicinal, these
     said cycles being saturated or unsaturated.
    6. Additive according to claim 5 characterized in that the
     glycerol monoesters are obtained from acids
     natural resources contained in the residues of
     Distillation of natural oils extracted from trees
     conifers, in particular coniferous conifers, as well as
     alkali and alkaline earth metal carboxylates,
     carboxylates of amines and the corresponding amides.
    7. Additive according to claim 6 characterized in that the
     resin acid esters are selected from the group
     constituted by the esters of abietic acid, of
     dihydroabietic, tetrahydroabietic acid, acid
     dehydroabietic, neoabietic acid, pimaric acid,
     of levopimaric acid and parastrinic acid.
    8. Additive according to one of claims 1 to 7 characterized in
     the esters and amides of formula (II) are
     obtained by reaction of an alcohol, polyol, amine compound,
     polyamine and / or alkanolamine on a carboxylic acid such
     than oleic acid or methyl oleate.
    9. Process for preparing the additive described according to one
     any of claims 1 to 8 characterized in that
     involves reacting at least one compound of the group
     consisting of monoalcohols, polyalcohols,
     alkanolamines, primary and secondary amines and
     polyamines on a triglyceride of formula (IV) below,
     in a molar ratio compound on triglyceride varying from
     0.1 to 3
    Figure img00190001
     in which R'1, R'2 and R'3 are identical or different
     and correspond to groups chosen from
     linear or weakly branched, saturated alkyl chains
     or unsaturated, comprising from 8 to 24 carbon atoms, the
     reaction occurring at a temperature between
     room temperature and 2500C, preferably between
  2.  80 and 2000C, for a period between 0.5 and 10
     hours, preferably between 2 and 4 hours under pressure
     atmospheric, possibly in the presence of 25 to 75%
     weight of a solvent selected from xylenes, ethylbenzene
     and commercial cuts of hydrocarbons for example those
     distilling between 190 and 2090C and containing 99% by weight of
     aromatic compounds.
    10. Process according to claim 9, characterized in that
     reacted from 0.5 to 2.8 moles, and preferably from 1.5 to
     2.5 moles of an alcohol, polyol, amine, polyamine or
     alkanolamine per mole of triglyceride.
    11. Method according to one of claims 9 and 10 characterized
     in that the triglycerides of formula (IV) are
     triglycerides of monocarboxylic fatty acids comprising
  3.  8 to 24 carbon atoms, chosen from 2-ethyl-acid
     hexanoic acid, lauric acid, myristic acid, acid
     hexadecanoic acid, palmlitic acid, stearic acid,
     oleic acid, linoleic acid, linolenic acid,
     nonadecanoic acid, arachidic acid, acid
     Behenic acid, erucic acid and ricinoleic acid.
  4. Process according to one of Claims 8 to 11, characterized
     in that the triglycerides are selected from the group
     consisting of vegetable and animal oils, in particular
     corn, rapeseed, sunflower, soybean and
     Castor.
    13. Method according to one of claims 8 to 12 characterized
     in that the alcohols are selected from the alkanols of
     group consisting of methanol, methanol, propanol,
     isopropanol, butanol, isobutanol, pentanol or
     still 2-ethyl hexanol, and / or oxyalkylated alcohols of
     R (0-CH2-CHR ') n-OH formula wherein R is a grouping
     alkyl of 1 to 6 carbon atoms, R 'an alkyl group
     from 1 to 4 carbon atoms and n an integer varying from
  5.  1 to 5 such as methylcellosolve, butylcellosolve and
     butyldiglycol.
    14. Method according to one of claims 8 to 12 characterized
     in that the polyols are selected from the group consisting of
     by ethylene glycol, diethylene glycol,
     triethylene glycol, propylene glycol,
     dipropylene glycol, arabitol, sorbitol, mannitol,
     trimethylolpropane, trimethylolhexane,
     pentaerythritol, butanediol-1,2, 2,4-hexanediol,
     pinacol, cyclohexanediol-1,2.
  6. Process according to one of Claims 8 to 12, characterized
     in that the primary and secondary amines are selected
     in 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 (2-ethyl) hexylamine, N
     methyldecylamine, N-methyldodecylamine, N
     méthyloléylamine.
    16. Method according to one of claims 8 to 12 characterized
     in that the polyamines are chosen from the compounds
     having 2 to 8 carbon atoms per amino chain and 2
     with 5 nitrogen atoms, the preferred polyamines being
     ethylenediamine, propylenediamine,
     diethylenetriamine, triethylenetetramine,
     tetraethylenepentamine, N- (aminoethyl) morpholine, N
     (aminopropyl) morpholine, N- (aminoethyl) piperazine, N
     methylpropanediamine or else N- (butyl) propanediamine,
     and the polymers resulting from the hydrogenation of the products
     of fatty amine addition having from 8 to 18 carbon atoms
     carbon with acrylonitrile such as N
     oléylpropanediamine.
    17. Method according to one of claims 8 to 12 characterized
     in that the alkanolamines are chosen from amines
     from 1 to 18 carbon atoms substituted by at least one
     Hydroxymethyl, hydroxyethyl or hydroxypropyl group
     such as ethanolamine, diethanolamine,
     triethanolamine, isopropanolamine,
     diisopropanolamine, triisopropanolamine, N
     methylethanolamine, N-hydroxyethylethylenediamine,
     tris- (hydroxymethyl) -aminomethane, N
     hydroxyethylmethylimidazoline, N
     hydroxyéthylheptadécénylimidazoline.
    18. Method according to one of claims 8 to 17 characterized
     in that the reaction product contains a mixture of
     compounds comprising
     from 5 to 25% by weight of at least one monoester of
     glycerol of formulas (IA) and or (1B) hereinafter
    Figure img00210001
     with R1 chosen from linear or weakly branched, saturated or unsaturated alkyl chains containing from 8 to 24 carbon atoms,
     from 20 to 60% by weight of at least one compound of
     formula (II) below
    Figure img00220001
     in which R2 is a linear or weakly branched, saturated or unsaturated alkyl chain comprising from 8 to 24 carbon atoms, and X is chosen from the group consisting of monoalcohol ester functions and linear or branched polyalcohols comprising from 1 to 8 carbon atoms, and the primary, secondary, alkanolamine and polyamine functional groups of aliphatic carbon chain, linear or branched, comprising from 1 to 18 carbon atoms,
     from 0.1 to 20 W by weight of at least one diester of
     glycerol of formula (IIIA) and / or (IIIB)
    Figure img00220002
     in which R3 and R4, identical or different,
     are chosen from linear alkyl chains or
     weakly branched, saturated or unsaturated,
     comprising from 8 to 24 carbon atoms,
     and possibly a remainder of at least one
     triglyceride of formula IV unreacted.
    19. Fuel for low sulfur land motor
     containing from 25 to 2500 ppm and preferably from 100 to 1000
     ppm by weight of at least one additive defined by one of the
     Claims 1 to 7 constituted by the defined species
     by ASTM D-439 possibly containing at least
     an oxygen compound or diesel fuels defined by the
     ASTM D-975.
FR9716538A 1997-12-24 1997-12-24 New additives compositions for improving the lubricating power of low sulfur petrol, diesel and jet fuels Withdrawn FR2772783A1 (en)

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Application Number Priority Date Filing Date Title
FR9716538A FR2772783A1 (en) 1997-12-24 1997-12-24 New additives compositions for improving the lubricating power of low sulfur petrol, diesel and jet fuels
FR9803225A FR2772784B1 (en) 1997-12-24 1998-03-17 Lubricity additive for fuel
JP20235798A JP3226497B2 (en) 1997-12-24 1998-07-16 Fuel for lubrication additives
RU99120297A RU2167919C1 (en) 1997-12-24 1998-12-22 Oily additive for combustibles
DE1998629167 DE69829167T2 (en) 1997-12-24 1998-12-22 Fuel lubricity additive
CA 2281635 CA2281635C (en) 1997-12-24 1998-12-22 Additive for fuel oiliness
PL98335330A PL189103B1 (en) 1997-12-24 1998-12-22 Lubricating additive to fuels
ES98963589T ES2242310T3 (en) 1997-12-24 1998-12-22 Lubricity additive for fuel.
DK98963589T DK0961820T3 (en) 1997-12-24 1998-12-22 Oily additive for motor fuel
HU0001251A HU222537B1 (en) 1997-12-24 1998-12-22 Lubricating additives for fuels Impact improver
EP19980963589 EP0961820B1 (en) 1997-12-24 1998-12-22 Additive for fuel oiliness
BR9807728A BR9807728B1 (en) 1997-12-24 1998-12-22 Lubricity fuel additive.
PT98963589T PT961820E (en) 1997-12-24 1998-12-22 Fuel untility additive
AT98963589T AT290057T (en) 1997-12-24 1998-12-22 Fuel lubricity additive
EP05000389A EP1522570A3 (en) 1997-12-24 1998-12-22 Fuel oiliness addtive
US09/355,992 US6511520B1 (en) 1997-12-24 1998-12-22 Additive for fuel oiliness
IDW990919A ID23178A (en) 1997-12-24 1998-12-22 Lubricant additives fuel
PCT/FR1998/002823 WO1999033938A1 (en) 1997-12-24 1998-12-22 Additive for fuel oiliness
KR1019997007492A KR100598227B1 (en) 1997-12-24 1998-12-22 Additive for fuel oilness and fuel for engine containing the same
MYPI9805849 MY121333A (en) 1997-12-24 1998-12-23 Fuel lubricity additive
ARP980106647 AR014163A1 (en) 1997-12-24 1998-12-23 Use of a lubricious additive to motor fuel, diesel and aviation, a tenor exceeding 500 ppm and engine fuel terrestrial low sulfur sulfur.
NO19994055A NO994055L (en) 1997-12-24 1999-08-23 Fuel with lubricating additive

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