EP0596769A1 - Stickstoffhaltige Produkte mit zwei Imideringen umfassende Motorbrennstoffzusätzezusammensetzungen und diese enthaltende Motorbrennstoffe - Google Patents

Stickstoffhaltige Produkte mit zwei Imideringen umfassende Motorbrennstoffzusätzezusammensetzungen und diese enthaltende Motorbrennstoffe Download PDF

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Publication number
EP0596769A1
EP0596769A1 EP93402614A EP93402614A EP0596769A1 EP 0596769 A1 EP0596769 A1 EP 0596769A1 EP 93402614 A EP93402614 A EP 93402614A EP 93402614 A EP93402614 A EP 93402614A EP 0596769 A1 EP0596769 A1 EP 0596769A1
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EP
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Prior art keywords
group
integer
carbon atoms
constituent
chosen
Prior art date
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EP93402614A
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English (en)
French (fr)
Inventor
Jacques Garapon
Alain Forestière
Philippe Mulard
Yvan Labruyère
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Elf Antar France
IFP Energies Nouvelles IFPEN
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Elf Antar France
IFP Energies Nouvelles IFPEN
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Publication of EP0596769A1 publication Critical patent/EP0596769A1/de
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/146—Macromolecular compounds according to different macromolecular groups, mixtures thereof
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    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
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    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
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    • C10L1/14—Organic compounds
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    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
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    • C10L1/00—Liquid carbonaceous fuels
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    • 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
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    • C10L1/00—Liquid carbonaceous fuels
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    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/221—Organic compounds containing nitrogen compounds of uncertain formula; reaction products where mixtures of compounds are obtained
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    • C10L1/14—Organic compounds
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    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224—Amides; Imides carboxylic acid amides, imides
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    • C10L1/00—Liquid carbonaceous fuels
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Definitions

  • the present invention relates to additive compositions, in particular for fuels, comprising at least one nitrogenous product comprising two terminal imide rings and at least one polyglycol soluble in said fuel, as well as preferably at least one detergent-dispersant.
  • additive compositions in particular for fuels, comprising at least one nitrogenous product comprising two terminal imide rings and at least one polyglycol soluble in said fuel, as well as preferably at least one detergent-dispersant.
  • the accumulation of these deposits in the combustion chambers can lead to a reduction in the volume of the combustion zone, which then results in an increase in the compression ratio of the engine. This phenomenon also promotes the appearance of rattling.
  • the deposits which form in the various parts of the engine in contact with the fuel can partially absorb a part of this fuel, thus contributing to a modification of the oxidizer-fuel mixture with a fuel depletion phase during absorption and an enrichment phase in the event of a desorption of this fuel. The modification of the richness of the fuel-air mixture no longer allows the engine to work in optimal conditions.
  • the accumulation of deposits in the engines and in particular on the intake valves can also be reduced by the use of fuels containing certain additives, for example detergent-type additives possibly combined for example with anticorrosion or anti-deposit additives for rooms combustion.
  • fuels containing certain additives for example detergent-type additives possibly combined for example with anticorrosion or anti-deposit additives for rooms combustion.
  • Additives well known in the trade, for example those of the polyisobutene-amine type, are usually associated with a mineral or synthetic oil and are capable of causing increased fouling of the combustion chambers and therefore an increase in the octane requirement of the motor with greater sensitivity to the rattling phenomenon.
  • Contamination of the combustion chambers occurs gradually during engine operation.
  • the latter is characterized by its octane requirement which corresponds to the minimum octane level of fuel necessary for the engine in order to operate without rattling.
  • the value of the engine octane requirement exceeds, in particular as a result of fouling of the combustion chambers, the value of the octane number of the fuel used to supply this engine, the rattling phenomenon.
  • the increase in engine octane requirements conventionally constitutes, for those skilled in the art, the ORI phenomenon according to the Anglo-Saxon abbreviation of "Octane Requirement Increase".
  • compositions which can be used in particular in motor fuels.
  • the compositions such as those described for example in patent application EP-A-327097 have good anti-ORI properties but relatively limited detergent properties. Furthermore, these compositions are not described as having good anticorrosion properties.
  • additive compositions as described below, which can be used in particular as multifunctional additives for engine fuels, in particular for fuels used in spark ignition engines, in which they make it possible in particular to limit the 'increase in octane requirement (ORI) of these engines and therefore limit, delay or even avoid, the appearance of the rattling phenomenon.
  • ORI octane requirement
  • the additive compositions according to the present invention combine their anti-ORI action with a detergent action both at the carburetor level, at the injectors level and at the intake valve level. They largely inhibit or reduce the formation of deposits on the intake valves, as well as clogging of carburetors or injectors.
  • additive compositions retain their anti-corrosion properties with respect to the parts with which the fuel comes into contact, both in the case of the fuels used for spark-ignition engines and in those used in spark-ignition engines. by self-ignition (Diesel engine).
  • the subject of the present invention is an additive composition, in particular for fuels, which comprises at least one constituent (A) and at least one constituent (B), said constituent (A) consisting of at least one polyazotated compound, comprising two rings imide type terminals, corresponding to the general formula (I): in which R1 and R2, identical or different, each represent a hydrocarbon group having from 1 to 120 carbon atoms or a group of formula R5 - (- O-R6-) a - (- O-R7-) b - in which R6 and R7, identical or different, each represent a divalent hydrocarbon group having from 2 to 6 carbon atoms, R5 represents a monovalent hydrocarbon group having from 1 to 60 carbon atoms a is zero or an integer from 1 to 100 and b is an integer from 1 to 100; R3 is a divalent hydrocarbon group having from 2 to 60 carbon atoms or a divalent group of formula -R8 - (- X-R9-) c - (- X
  • the additive compositions of the present invention can also be added to a non-hydrocarbon fuel such as, for example, an alcohol or a mixture of alcohols.
  • the constituent (A) is preferably chosen from the compounds of general formula (I) above in which R1 and R2, identical or different, each most often represent an aliphatic group, saturated or unsaturated, linear or branched having from 1 with 60 carbon atoms and for example an alkyl group, linear or branched having from 1 to 30 carbon atoms or a group of formula R5 - (- O-R6-) a - (- OR7-) b - in which R6 and R7, identical or different, each most often represent a divalent aliphatic group, saturated or unsaturated, linear or branched having 2 to 4 carbon atoms and for example an alkylene group, linear or branched having 2 to 4 carbon atoms such that for example an ethylene, trimethylene, propylene, tetramethylene and isobutylene group, R5 most often represents a monovalent, saturated or unsaturated, linear or branched aliphatic group having from 1 to 20 carbon atoms and for example an alkyl
  • polyazotated compounds (A) which can be used in particular in the compositions of multifunctional additives for engine fuel according to the invention, those in which the group R4 comprises at least 6 and preferably at least 12 carbon atoms are usually used.
  • the polyazotated compounds (A) used in the present invention can be manufactured by any methods known to those skilled in the art. By way of nonlimiting examples of methods making it possible to prepare the compounds of general formula (I) above, the following two methods will be mentioned.
  • esters of succinosuccinic acids which are most often used are commercial compounds or can be easily obtained by conventional methods of synthesis well known to those skilled in the art. These esters can for example be obtained by transesterification from dimethylsuccinosuccinate (DMSS).
  • DMSS dimethylsuccinosuccinate
  • alkyl group of these products most often contains at least 5 carbon atoms and is most often linear.
  • alkyl groups mention may be made of n-pentyl and n-heptyl groups.
  • These oxyalkylated products are commercial products sold by the company SHELL under the generic name OXYLUBE or by the company ICI. These compounds usually have a molecular mass of approximately 500 to approximately 2500 and most often approximately 600 to approximately 2000.
  • alpha-omega biprimary diamines which are usually used are compounds well known to those skilled in the art. As specific compounds, mention may be made, by way of nonlimiting examples, of: ethylenediamine, propylenediamine, diethylenetriamine, dipropylenetriamine, triethylenetetramine, tripropylenetetramine, tetraethylenepentamine, tetrapropylenepentamine, hexamethylenediamine, di (trimethylene) -triamine, 2,2-dimethyl-1,3-propanediamine, N, N'-bis (3-amino-propyl) -ethylenediamine, (2-aminoethyl) -amino- 3 propylamine, trimethyl-hexamethylenediamines for the case of amines not containing oxygen atoms in their formula.
  • amines containing oxygen atoms in their formula mention may be made of the polyamines of formula: NH2-R8 - (- O-R9-) c - (- O-R10-) d - (- O-R11-) e -NH2 in which preferably R8, R9 R10 and R11, identical or different, each represent an alkylidene group having from 2 to 4 carbon atoms for example ethylidene, propylidene, isopropylidene, butylidene, isobutylidene, preferably c is an integer from 1 to 60 and d and e are equal to zero or c is an integer from 1 to 59, e is zero or an integer such that the sum c + e is from 1 to 59 and d is an integer from 1 to 50, with in each case the sum c + d + e equal to an integer from 1 to 60.
  • diamines mention may be made of those corresponding to the formulas in which c is 2, 3, 5, 6 or about 33, or of formula: where d is approximately equal to 8, 9, 15, 16 or 40 and c + e is approximately 2 or 3.
  • the acid or acid derivative usually used in the context of the present invention is a succinic compound or an alkylsuccinic or alkenylsuccinic compound, preferably a succinic anhydride. It is also possible to use a phthalic derivative, preferably phthalic anhydride or a phthalic anhydride having an alkyl group on one of the carbon atoms of the nucleus.
  • succinic type compounds include succinic anhydride, methylsuccinic anhydride often called citraconic anhydride, and alkylsuccinic or alkenylsuccinic anhydrides usually having a number average molecular weight of about 200 to 3000, preferably 500 to 2000 and most often 700 to 1500.
  • succinic derivatives are widely described in the prior art; they are for example obtained by the action of at least one alpha olefin or of a chlorinated hydrocarbon on maleic acid or anhydride.
  • the alpha olefin or the chlorinated hydrocarbon used in this synthesis can be linear or branched, and usually contain from 10 to 150 carbon atoms, preferably from 15 to 80 carbon atoms and most often from 20 to 75 carbon atoms in their molecule.
  • This olefin can also be an oligomer, for example a dimer, a trimer or a tetramer, or a polymer of a lower olefin, for example having 2 to 10 carbon atoms, such as ethylene, propylene, n -butene-1, isobutene, n-hexene-1, n-octene-1, methyl-2-heptene-1 or methyl-2-propyl-5-hexene-1. It is possible to use mixtures of olefins or mixtures of chlorinated hydrocarbons.
  • succinic anhydrides mention may be made of n-octadecenylsuccinic anhydride, dodecenylsuccinic anhydride and polyisobutenyl succinic anhydrides, often called PIBSA, having a number-average molecular mass as defined above.
  • one or more biprimary diamines can be used for the synthesis of the products of formula (I), (II) or (IV).
  • the additive compositions of the invention also contain at least one constituent (B) chosen from fuel-soluble polyglycols preferably having a number average molecular weight of 480 to 2,100 and of general formula (VII): wherein each of the R groups independently represents a hydrocarbon group having 2 to 6 carbon atoms and x represents the average degree of polymerization.
  • constituent (B) chosen from fuel-soluble polyglycols preferably having a number average molecular weight of 480 to 2,100 and of general formula (VII): wherein each of the R groups independently represents a hydrocarbon group having 2 to 6 carbon atoms and x represents the average degree of polymerization.
  • the constituent (B) is a polyglycol having a polydispersity index of approximately 1 to approximately 1.25 and preferably approximately 1 to 1.15, of general formula (VII) in which each R groups independently represent an alkylene group, linear or branched, having from 2 to 4 carbon atoms, preferably an ethylene or propylene group.
  • each of the groups R represents a propylene group of formula:
  • the polyglycol used is preferably a polyglycol of number average molecular weight from 600 to 1,800 and most often from 650 to 1,250.
  • the additive compositions further comprise at least one component (C) selected from the group formed by detergent-dispersant products.
  • This constituent (C) is usually chosen from the group formed by polyolefins, preferably polyisobutenes, polyisobuten-amines, mixtures of these types of compounds and the products which are in particular described in European patent application EP-A -349369 in the name of the plaintiff, as well as those described in patent US-A-4375974.
  • the products described in application EP-A-349 369 result from the reaction in a first step of at least one succinic derivative chosen from the group formed by alkenylsuccinic acids and anhydrides and polyalkenylsuccinic acids and anhydrides on at least one 1 - (2-hydroxyethyl-) imidazoline substituted in position 2 by an alkyl or alkenyl radical, linear or branched, having from 1 to 25 carbon atoms, the imidazoline / succinic derivative molar ratio being from 0.1: 1 to 0.9 : 1, preferably from 0.2: 1 to 0.8: 1 and most often from 0.3: 1 to 0.7: 1, said step being carried out under conditions such that one forms and that the 'at least 0.15 mole of water is eliminated per mole of imidazoline used; and in a second stage of the reaction of the product resulting from the first stage with at least one polyamine corresponding to one of the following general formulas: in which R13 represents a hydrogen atom or a hydrocarbon
  • the succinic acid or anhydride used in the context of the present invention to prepare the constituent (C) is usually chosen from those defined above in the context of the preparation of the compounds of general formula (I).
  • (2-hydroxyethyl -) - imidazolines substituted in position 2 by an alkyl or alkenyl radical having from 1 to 25 carbon atoms used in the context of the present invention to prepare component (C), are usually commercial compounds or which can be synthesized for example by reaction of at least one organic acid with N- (2-hydroxyethyl) -ethylenediamine. The reaction proceeds by a first amidation step followed by cyclization.
  • the organic acids used usually have from 2 to 26 carbon atoms; they are preferably aliphatic monocarboxylic acids.
  • the first stage of preparation of component (C) is usually carried out by progressive addition of the imidazoline derivative to a solution of the succinic derivative in an organic solvent, at ordinary temperature, then heating to a temperature usually between 65 ° C and 250 ° C and preferably between 80 ° C and 200 ° C.
  • the organic solvent used in this preparation has a boiling point between 65 ° C and 250 ° C and is usually chosen so as to be able to allow the elimination of the water formed during the condensation of imidazoline on the derivative succinic, preferably in the form of a water-organic solvent azeotrope.
  • an organic solvent such as benzene, toluene, xylenes, ethylbenzene or a cut of hydrocarbons such as for example the commercial cut SOLVESSO 150 (190-209 ° C) containing 99% by weight of aromatic compounds. It is possible to use mixtures of solvents, for example a mixture of xylenes.
  • the duration of heating after the end of the addition of imidazoline is usually 0.5 to 7 hours, preferably 1 to 5 hours. This first step will preferably be continued at the chosen temperature until the end of the evolution of the water formed during the reaction.
  • the amount of water removed during this first step is usually about 0.15 to 0.6 moles and most often about 0.5 moles per mole of imidazoline involved in the reaction.
  • At least one polyamine, preferably diluted in an organic solvent is gradually added to the product or mixture resulting from this first step, after optional cooling, and then usually heated to a temperature between 65 ° C. and 250 ° C. and preferably between 80 ° C and 200 ° C.
  • the solvent used in the second step is preferably the same as that in the first step and the temperature is also the same during these two steps.
  • the reactions are usually carried out at a temperature corresponding to the reflux temperature.
  • the duration of this heating during this second step is usually 0.1 to 7 hours and preferably 0.2 to 5 hours.
  • the amount of polyamine used is at least 0.1 mole per mole of succinic anhydride introduced during the first step and it is preferably such that the total amount of imidazoline substituted and of polyamine used in the preparation is 0.8 to 1.2 moles, preferably 0.9 to 1.1 moles per mole of succinic derivative.
  • the substituted imidazoline to polyamine molar ratio is preferably from 1: 1 to 7: 1 and most preferably from 1: 1 to 3: 1.
  • the amount of water removed during this second step is usually such that the amount of total water removed during the two successive reactions represents from 0.2 to 0.7 mole per mole of succinic derivative.
  • the polyamines of formula (V) are preferably those in which R13 is a hydrogen atom or a hydrocarbon group having from 1 to 30 carbon atoms, Z is preferably a group -NR15- in which R15 preferably represents an atom of hydrogen or a hydrocarbon group having 1 to 30 carbon atoms, each of R14 independently preferably represents a hydrogen atom or a methyl group, p is an integer from 2 to 4 and when Z is a group -NR15- m is preferably an integer from 1 to 5.
  • Z is -NR15-, R13, R14 and R15 each represent a hydrogen atom, p is equal to 2 and m is an integer from 1 to 5 or those in which R13 represents a hydrocarbon group preferably having from 5 to 24 carbon atoms, Z represents a group -NR15- in which R15 is a hydrogen atom, R14 represents a hydrogen atom, p is a number integer from 2 to 4, preferably 3, and m is an integer from 1 to 5, preferably 1.
  • the hydrocarbon groups R13 and R15 are usually alkyl, alkenyl, linear or branched, aryl, aryl-alkyl (aralkyl), alkyl-aryl (alkaryl) or cycloaliphatic groups.
  • the R13 and R15 groups are preferably alkyl or alkenyl groups, linear or branched.
  • the hydrocarbon group R14 is usually a preferably linear alkyl group, for example methyl, ethyl, n-propyl or n-butyl.
  • N-alkyl diamino-1,3 propane for example N-dodecyldiamino-1,3 propane, N-tetradecyldiamino-1,3 propane, N-hexadecyldiamino-1,3 propane, N-octadecyldiamino-1,3 propane, N-eicosyldiamino-1,3 propane and N-docosyldiamino-1,3 propane; mention may also be made of N-alkyldipropylene triamines, for example N-hexadecyldipropylene triamine, N-octadecyldipropylene triamine, N-eicosyldipropylene triamine and N-docosyldiprop;
  • disubstituted diamines N, N there may be mentioned N, N-diethyl-1,2-diamino ethane, N, N-diisopropyl-1,2-diamino ethane, N, N-dibutyl diamino-1, 2 ethane, N, N-diethyl diamino-1,4-butane, N, N-dimethyl diamino-1,3 propane, N, N-diethyl diamino-1,3 propane, N, N-dioctyl diamino-1,3 propane, N, N-didécyl diamino-1,3 propane, N, N-didodécyl diamino-1,3 propane, N, N-dissetradécyl diamino-1,3 propane, N, N-dihexadecyl diamino-1,3 propane, N, N-dioctadécyl diamin
  • etheramines examples include N- (3-octyloxy-propyl) 1,3-diamino propane, N- (3-decyloxy-propyl) 1,3-diamino propane, N- [(trimethyl- 2,4,6 decyl) 3-oxy propyl] diamino-1,3 propane.
  • the polyamines of formulas (VI) are preferably those in which R13 and R15 each represent a hydrogen atom, D, E, F and G, identical or different, each represent an alkylene group having 2 to 4 carbon atoms per example ethylene, trimethylene, methylethylene, tetramethylene, methyltrimethylene, methyl-1 trimethylene and methyl-2 trimethylene, f is an integer from 1 to 60 and g and h are equal to zero or f is an integer from 1 to 59, h is zero or an integer such that the sum f + h is from 1 to 59 and g is an integer from 1 to 50, with in each case the sum f + g + h equal to an integer from 1 to 60.
  • the products described by the applicant in patent US-A-4375974 and which can be used, in the context of the present invention as component (C), are those resulting from the reaction of at least one polyamine, having at least one primary amino group and corresponding to the general formula (V) above, on at least one succinic derivative such as those described above, said reaction being carried out under conditions of formation and elimination of the water of reaction. Most often the reaction is carried out at a temperature of about 120 ° C to about 200 ° C with an amine to succinic derivative molar ratio of about 0.9: 1 to about 1.2: 1. This reaction can be carried out in the absence of solvent or in the presence of a solvent such as for example an aromatic hydrocarbon, a cut of hydrocarbons having a boiling point of about 70 ° C to about 250 ° C.
  • a solvent such as for example an aromatic hydrocarbon, a cut of hydrocarbons having a boiling point of about 70 ° C to about 250 ° C.
  • the constituent (C) which can be used in the context of the present invention can also be chosen from the group formed by polyisobutenes, polyisobuten-amines, mixtures of these two types of compounds.
  • the polyolefins used can be polymers or copolymers or the corresponding amino or hydrogenated derivatives formed from hydrocarbons having from 2 to 10 carbon atoms in their molecule.
  • These polymeric compounds are usually prepared from monoolefinic or diolefinic compounds and usually have a number average molecular weight of about 500 to 10,000, often about 500 to 3500 and preferably about 650 to 2600.
  • the starting compounds used to manufacture these polymers are olefins having from 2 to 6 carbon atoms in their molecule, such as for example ethylene, propylene, isopropylene, butene, isobutene, amylene, hexylene, butadiene and isoprene.
  • Propylene, isopropylene, butene and isobutene are very frequently used.
  • the other polyolefins which can also be used are those obtained by cracking of high molecular weight olefin polymers or copolymers into compounds having a molecular weight in the molecular weight range mentioned above.
  • polypropylenes of number average molecular mass of approximately 750 to 1000 and for example of approximately 800 polyisobutenes of number average molecular mass from about 1000 to 1500 and for example from about 1300.
  • the constituent (C) is a mixture comprising a majority proportion of polyisobutene-ethylenediamine and a minority proportion of polyisobutene.
  • This mixture is most often used dissolved in a hydrocarbon solvent so as to facilitate its incorporation into the fuel.
  • the proportion of amino polymer in this mixture is usually from about 50% to about 80% by weight and for example from about 60% by weight and the proportion of hydrocarbon polymer is usually from about 5% to about 30% by weight and preferably from about 10% to about 25% by weight.
  • Polyisobutene ethylene diamine is a compound of general formula: in which z is a number from approximately 10 to approximately 40, preferably from approximately 30 to approximately 35 and for example approximately 33.
  • Polyisobutene is a compound of general formula: in which t is a number from approximately 10 to approximately 40, preferably from approximately 30 to approximately 35 and for example approximately 33.
  • the solvent used to dissolve the polymeric compounds and facilitate their incorporation into the fuel is most often a light aromatic distillate.
  • Can be used as component (C) comprising, dissolved in a light aromatic distillate, a polyisobutene and a polyisobutene-ethylene diamine as described above, the product sold by the company CHEVRON CHEMICAL COMPANY under the trade name ORONITE OGA -472.
  • ORONITE OGA-472 is a composition comprising approximately 60% by weight of polyisobutene-ethylene diamine, approximately 27% by weight of polyisobutene and approximately 13% by weight of light aromatic distillate comprising xylene and C9 alkylbenzenes.
  • the additive compositions according to the invention can in particular be used as an additive having good anti-corrosion activity for a fuel based on hydrocarbons or on a mixture of hydrocarbons and at least one oxygenated compound chosen from the group formed by alcohols and ethers.
  • These compositions can also be used as a multifunctional additive having in particular good anti-ORI and detergent-dispersant properties for an engine fuel, for a spark-ignition engine, based on hydrocarbons or a mixture of hydrocarbons and minus an oxygenated compound chosen from the group formed by alcohols and ethers.
  • these additive compositions are added to the fuel so as to obtain a mass concentration, of the additive composition in the engine fuel, of 10 to 10,000 ppm, often from 100 to 5,000 ppm and preferably of 100 at 2000 ppm.
  • the weight ratio of component (A) to component (B) [(A) / (B)] is usually from about 0.05: 1 to about 5: 1 ,. This ratio is often from approximately 0.05: 1 to approximately 2: 1 and preferably from approximately 0.1: 1 to approximately 2: 1.
  • the weight ratio of the constituent ( B) to component (C) [(B) / (C)] is usually from about 0.1: 1 to about 50: 1 and preferably from about 0.2: 1 to about 20: 1.
  • a 2 liter double-jacketed reactor equipped with a stirring system, a dip tube allowing the introduction of argon, a thermometer and a coolant, 182.4 g ( 0.8 mole) of dimethylsuccinosuccinate (DMSS) and 2512 g (2.29 moles) of a polyoxypropylated and ethoxylated monoalcohol (sold by the company ICI) with 70% of primary alcohol function and whose molecular mass is 1097 (i.e. 30% excess).
  • the temperature is brought to 135 ° C and then 11.6 g (3.4x10 ⁇ 2 mole) of butyl titanate Ti- (OC4H9) 4 are introduced, and the temperature is then raised to 145 ° C while maintaining the stirring.
  • the temperature is kept stirring at 145 ° C for one hour and thirty minutes.
  • a first fraction of methanol is collected at atmospheric pressure, then the pressure is gradually reduced using a water pump to a value equal to 27 KiloPascals (KPa) and it is collected, (the temperature of the flask being maintained at 145 ° C) after condensation, an alcoholic phase.
  • KPa KiloPascals
  • Analysis by gas chromatography shows that the alcoholic phase thus recovered contains methanol, polyoxyalkylated alcohol and butanol.
  • the total amount of methanol recovered (51.2 g) corresponds to the expected amount.
  • the reactor contains 1811 g of products, which, according to analysis by gel permeation chromatography, contain 89.4% of polyoxyalkylated alcohol succinosuccinate, ie 1619 g (0.76 moles), which corresponds to a molar conversion of the 95% DMSS.
  • polyoxyalkylated alcohol succinosuccinate ie 1619 g (0.76 moles)
  • the residual alcohols are removed.
  • the product obtained is dissolved in xylene with a weight ratio of 1: 1.
  • the solution thus obtained is called solution No. 1.
  • an amount of solution No. 1 prepared during the first step is introduced corresponding to 0.1 mole of the diester of succinosuccinic acid and of polyoxyalkylated alcohol
  • the solution No. 2 obtained during the second stage is added dropwise.
  • the temperature is gradually raised to 120 ° C. and 3.5 milliliters (ml) of water are collected, ie 97% of the theoretical amount for the formation of a product of formula (I) (2 moles of water per mole diester).
  • n 0. 568 g of a 50% by weight solution of product in xylene are recovered. This solution is called additive 2.
  • Additive 2 was analyzed after evaporation of the solvent.
  • 0.1 mol of the methyl diester of succinosuccinic acid is introduced into a reactor identical to that used in the first stage, in the form of a 50% by weight solution in xylene, with stirring, and the mixture is added dropwise. drop solution No. 3 obtained during the first step.
  • the temperature is gradually raised to 120 ° C. and 3.5 milliliters (ml) of water are collected, ie 97% of the theoretical amount for the formation of a product of formula (I) (2 moles of water per mole diester).
  • n 0.
  • Additive 2 was analyzed after evaporation of the solvent. Its number average molecular mass, measured by tonometry, is 5800.
  • the infrared spectrum shows the following characteristic bands: 1610 cm ⁇ 1 attributable to the enamine double bond, 1660 cm ⁇ 1 attributable to the carbonyl bond of the l ester 'succinosuccinic acid, and the characteristic doublet of aliphatic succinimides at 1710 cm ⁇ 1 and 1770 cm ⁇ 1.
  • PIBSA polyisobutenyl succinic anhydride
  • PIBSA polyisobutenyl succinic anhydride
  • maleic anhydride the assay of the anhydride functions of this product shows that one has 0, 7 anhydride function per kilogram
  • 1018 g of xylene are loaded into a 2 liter reactor fitted with mechanical stirring, a Dean-Stark separator and a temperature regulation system.
  • the reactor temperature is lowered to 50 ° C. and then maintained at this value during the time of the gradual addition (dropwise) of 56 g (0.297 mole) of tetraethylenepentamine diluted in 49 g of xylene. At the end of this addition the mixture is again brought to reflux for 15 minutes. Water elimination again occurs. The total amount of water collected during these two reaction stages is 7.2 ml.
  • the infrared spectrum shows two absorption bands (1710 cm ⁇ 1 and 1770 cm ⁇ 1) characteristic of the succinimide function with a shoulder ( 1740 cm ⁇ 1) characteristic of the ester function.
  • compositions F1 to F5 comprising various weight quantities of the constituents (A), (B) and (C) defined below.
  • Component (A) is formed by one of the compositions obtained in Examples 1 and 2.
  • Component (C) is formed by the composition obtained in Example 3.
  • composition F1 according to the present invention contains the constituent (A) formed by the composition obtained in Example 1, the constituent (B) formed by the polypropylene glycol described above and the constituent (C) formed by the composition obtained in Example 3. These constituents are used in a weight ratio, in terms of active material, A: B: C of 1: 5: 5.
  • Composition F2 contains the constituent (A) formed by the composition obtained in Example 2, the constituent (B) formed by the polypropylene glycol described above and the constituent (C) formed by the composition obtained in l 'example 3. These constituents are used in a weight ratio, in terms of active material, A: B: C of 1: 5: 5.
  • Composition F3 (comparison composition) contains the constituent (B) formed by the polypropylene glycol described above as well as the constituent (C) formed by the composition obtained in Example 3, but no constituent (A).
  • Composition F4 (comparison composition) contains the constituent (A) formed by the composition obtained in Example 1 and the constituent (C) formed by the composition obtained in Example 3, but no constituent (B).
  • the active matter weight ratio A: C is 1: 5.
  • Composition F5 according to the present invention contains component (A) formed by the composition obtained in Example 1 and component (B) formed by the polypropylene glycol described above, but no component (C).
  • the active matter weight ratio A: B is 1: 5.
  • the advance values corresponding to the appearance of rattling, and expressed in crankshaft degrees and very often designated by the initials KLSA are determined 1 time at 0 and 150 hours at different engine speeds. The results obtained are expressed in KLSA at 150 hours for seven different engine speeds: 1500 rpm, 2000 rpm, 2500 rpm, 3000 rpm, 3500 rpm, 4000 t / min. and 4500 rpm. These results are presented in Table II below. The overall weight (expressed in grams (g)) of the deposits on the 4 intake valves was also measured and the results are given in Table II.
  • compositions according to the invention give lower values of KLSA, limit the increase in the octane requirement of the engine and delay the appearance of unstable idling; and that on the other hand with the additive compositions according to the invention the weight of deposits on the intake valves is greatly reduced compared to that obtained with the fuel alone or with the fuel containing the compositions of comparison additives.
  • the composition F5 according to the invention (but which is not part of the preferred compositions according to the invention) is effective in limiting the increase in the octane requirement of the engine and delays the appearance of unstable idling but is not very effective in limiting the weight of deposits on the intake valves
  • the “carburetor” detergency properties of the additive compositions prepared in Example 4 are evaluated.
  • the engine test procedure is carried out according to European standard R5-CEC-F03-T-81.
  • the results are expressed in terms of merit from zero to ten.
  • a merit 10 corresponds to a clean carburetor and a merit 0 to a very dirty carburetor.
  • the additive compositions are added to the fuel so as to obtain a concentration by weight of active material in the additive fuel specified for each example in Table III below which gives the results obtained:
  • the fuel used in these assessments is an unleaded premium fuel with an engine octane rating of 85.3 and a research octane rating of 96.7.
  • This premium fuel has an initial distillation point of 36 ° C and a final distillation point of 203 ° C.
  • This fuel has an engine octane number of 86 and a research octane number of 96.
  • the additive compositions are added to the fuel so as to obtain a concentration, by weight of active material in the additive fuel, specified for each example in table IV below which gives the results obtained:
  • the flow rate of each injector is measured at the start and end of the test in order to assess the percentage of flow restriction induced by fouling of the injectors.
  • This fuel has an engine octane number of 85.7 and a research octane number of 97.5.
  • compositions are added to the fuel so as to obtain a concentration, by weight of active material in the additive fuel, specified for each example in Table V below which gives the results obtained:
  • the tests are carried out on a Hyundai generator set equipped with a generator (240 Volt, 5500 Watt) driven by a 359 cc 4-stroke twin-cylinder engine with tumbled valves.
  • the engine is conditioned with new valves that are weighed.
  • the valves are dismantled, washed with hexane, dried, then weighed after physical removal (by scraping) of the deposits formed on the valve on the combustion chamber side.
  • the results presented below give the average of the deposits by weight relative to a valve, calculated from the weight of deposits measured, on the tulip of each intake valve, by difference between the weight of said new valve and the weight of said valve at the end of each test after removal of deposits on the combustion chamber side.
  • the fuel used in these assessments is an unleaded premium fuel identical to that described in Example 5.
  • the additive compositions are added to the fuel so as to obtain a concentration, by weight of active material in the additive fuel, specified for each example in Table VI below, also giving the results obtained.
  • the anti-corrosion properties of the additive compositions prepared in Example 4 are evaluated.
  • the tests consist in determining the extent of the corrosion produced on samples of polished ordinary steel, in the presence of water, by following standard ASTM D 665 modified (temperature 32.2 ° C, duration 20 hours). The results are expressed as a percentage (%) of the surface of the corroded test piece after 20 hours.
  • the fuel is the same as that used in Example 5.
  • the amount of composition is added to the fuel so as to obtain a concentration, by weight of active material in the additive fuel, specified for each example in Table VII below. , also giving the results obtained:
  • composition is added to the fuel so as to obtain a concentration, by weight of active material in the additive fuel, specified for each example in Table VIII below, further summarizing the results obtained:
  • compositions according to the present invention make it possible to very significantly limit the increase in octane requirement of spark-ignition engines and has the qualities of detergent additives for the intake system as well than anticorrosion.

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US5425788A (en) 1995-06-20
FR2697533A1 (fr) 1994-05-06
JPH0726277A (ja) 1995-01-27

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