EP0277345B1 - Composition de carburant ou de lubrifiant, contenant des dérivés de polybutyl ou polyisobutyl - Google Patents

Composition de carburant ou de lubrifiant, contenant des dérivés de polybutyl ou polyisobutyl Download PDF

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Publication number
EP0277345B1
EP0277345B1 EP87119004A EP87119004A EP0277345B1 EP 0277345 B1 EP0277345 B1 EP 0277345B1 EP 87119004 A EP87119004 A EP 87119004A EP 87119004 A EP87119004 A EP 87119004A EP 0277345 B1 EP0277345 B1 EP 0277345B1
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EP
European Patent Office
Prior art keywords
polybutyl
acid
polyisobutyl
radical
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.)
Expired - Lifetime
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EP87119004A
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German (de)
English (en)
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EP0277345A1 (fr
Inventor
Dieter Dr. Franz
Rudolf Dr. Kummer
Helmut Dr. Mach
Hans Peter Dr. Rath
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BASF SE
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BASF SE
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    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • 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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    • C10L1/00—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
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
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    • 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
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
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    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/86—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of 30 or more atoms
    • C10M129/88—Hydroxy compounds
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    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
    • C10M133/56—Amides; Imides
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    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/06—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic nitrogen-containing compound
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2215/28—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
    • C10M2215/30—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/251—Alcohol-fuelled engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/28—Rotary engines

Definitions

  • the invention relates to a fuel or lubricant composition, the use of polybutyl or polyisobutyl derivatives in such compositions, and to esters and (poly) alkoxylates of polybutyl or polyisobutyl alcohol.
  • Polyisobutene derivatives have been widely described in the literature and are widely used worldwide as lubricants and fuel additives.
  • the intermediate products for the production of such additives are polybutent chloride, polybutenyl succinic anhydride and polybutylphenols. They are used almost exclusively to make detergents.
  • these are generally calculated as “ashless dispersants", in the case of polybutylphenols occasionally also as Mannich dispersants.
  • These dispersants have the function of oil-insoluble combustion residues, which can make up to 10% by weight of the lubricating oil in diesel engines (e.g. soot, coke, lead compounds and on organic salts) and their caking to form solid particles with a size of 0.6 to 1.5 ⁇ m of resin and asphalt-like oxidation products in the lubricating oil is favored to keep in suspension and thereby prevent deposits on metal surfaces, oil thickening and sludge excretions in the engine as well as corrosive wear by neutralizing acidic combustion products.
  • the secondary products are usually referred to as carburetor or valve detergents. Your job is to free the entire inlet system of deposits, prevent further deposits and protect the system from corrosion.
  • the deposits are mostly the result of unstable fuel such as unhydrogenated or partially hydrogenated cracked petrol or pyrolysis petrol or of impurities from pipelines, storage and transport containers.
  • the alcohols disclosed in FR-A-1 432 974 - used as additives in lubricants after reaction with alkylene oxides - are produced in a complex process by oxonolysis of olefins.
  • the double bonds in the olefin are cleaved in oxonolysis, so that, according to D1, a large number of different cleavage fragments, even with a low molecular weight, are formed.
  • polybutenes are used according to the invention in which more than 10% of the double bonds are ⁇ -permanent.
  • the alcohols thus differ significantly from the alcohols known from FR-A-1 432 974.
  • the object of the invention is to provide fuel or lubricant compositions which contain carrier substances which are inexpensive to produce, have increased stability and, moreover, are practically halogen-free, i.e. are free of chlorine and bromine. These carrier substances should also have a detergent effect, if appropriate.
  • a fuel or lubricant composition which, in an amount effective as a detergent, contains at least one polybutyl or polyisobutyl alcohol of the general formula (I) R - CH2 - OH (I), wherein R is a polybutyl or polyisobutyl radical with a molecular weight derived from isobutene and up to 20% by weight of n-butene M N is from 324 to 3000, or a (poly) alkoxylate of the polybutyl or polyisobutyl alcohol of the formula I or a corresponding carboxylic acid ester of the polybutyl or polyisobuthyl alcohol, the polybutyl or polyisobuthyl alcohol being obtained by hydroformylation of reactive polybutenes or polyisobutenes, in which more than one 10% of the double bonds are ⁇ -permanent, is obtained.
  • R is a polybutyl or polyisobutyl radical with a molecular weight derived from is
  • the (poly) alkoxylate of polybutyl or polyisobutyl alcohol is one of the general formula (II) wherein R has the meanings given above, n is an integer from 2 to 8 and m is an integer from 1 to 200.
  • the (poly) alkoxylate of polybutyl or polyisobutyl alcohol is particularly preferably one which is derived from ethylene oxide, propylene oxide or butylene oxide or mixtures thereof.
  • the term (poly) alkoxylate should include alkoxylates and polyalkoxylates of polybutyl or polyisobutyl alcohol.
  • this is expressed by the index m, which stands for 1 in the case of alkoxylates and stands for a number> 1 in the case of (poly) alkoxylates.
  • the index n has the meanings 2 to 8, preferably 2 to 4.
  • the index m stands for an integer between 1 and 200, preferably between 5 and 100, particularly preferably between 10 and 50.
  • Mixtures of the (poly) alkoxylates can of course also be used. These result, for example, from the use of mixed oxides of ethylene, propylene and butylene oxide. Ethylene oxide and propylene oxide are particularly preferred as the starting component.
  • the acid group forming the ester can be one which is saturated and unsaturated, aliphatic or aromatic, acyclic or cyclic Mono- or polycarboxylic acids is derived.
  • the monocarboxylic acid residue preferably has 2 to 9 carbon atoms.
  • the acid residue can also be derived from hydroxycarboxylic acids, for example from citric acid.
  • the di-, tri- and tetracarboxylic acids from which the acid group is derived can also be saturated and unsaturated, aliphatic or aromatic, acyclic or cyclic carboxylic acids, in particular those with 4 to 9 carbon atoms.
  • the carboxylic acid groups can optionally also have basic functions. These basic functions result from the reaction of the acid group in the ester with, for example, NH3, mono-, di-, tri-, tetra- or polyamines or amides. The corresponding ammonium or amine salts, amides or imides, or mixtures thereof are formed. Such esters with basic functions are particularly preferred.
  • carboxylic acids are acetic acid, propionic acid, ethylhexanoic acid, isononanoic acid, succinic acid, adipic acid, maleic acid, phthalic acid, terephthalic acid, trimellitic acid, trimesic acid, pyrromellitic acid and butanetetracarboxylic acid.
  • Combinations of the polybutyl or polyisobutyl alcohol of the general formula (I) with the corresponding (poly) alkoxylates or esters of the polybutyl or polyisobutyl alcohols can also be present in the fuel and lubricant compositions according to the invention.
  • the invention also relates to the esters and (poly) alkoxylates of polybutyl or polyisobutyl alcohol of the general formula VII as new substances R-CH2-O-R ⁇ (VII) wherein R has the above meanings and R ⁇ is an acyl radical or together with the oxygen is a (poly) alkoxilate radical.
  • the acyl radical R ⁇ is one which is derived from a saturated or unsaturated, aliphatic or aromatic, acyclic or cyclic mono- or polycarboxylic acid, in particular with the above possible meanings.
  • the (poly) alkoxylate group -O-R ⁇ corresponds to the following formula: wherein n and m have the meanings mentioned at the beginning.
  • the polybutyl or polyisobutyl alcohol used to form the esters and (poly) alkoxylates is obtained by hydroformylation of reactive polybutenes or polyisobutenes in which more than 10% of the double bonds are ⁇ -permanent.
  • the fuel or lubricant compositions according to the invention also contain nitrogen-containing additives in addition to the polybutyl or polyisobutyl alcohol of the general formula (I) or its (poly) alkoxylates or esters.
  • R has the definition given above and R1 and R2, which may be the same or different, represent hydrogen, aliphatic or aromatic hydrocarbon radicals, primary or secondary, aromatic or aliphatic aminoalkylene radicals or polyaminoalkylene radicals, polyoxyalkylene radicals, heteroaryl or heterocyclyl radicals, or together with that Nitrogen atom to which they are attached form a ring in which further heteroatoms may be present.
  • the radicals R 1 and R 2 in the general formula (III) are identical or different and each represents hydrogen, alkyl, aryl, hydroxyalkyl, an aminoalkylene radical of the general formula (IV) wherein R3 represents an alkylene radical and R4 and R5, which are identical or different, represent hydrogen, alkyl, aryl, hydroxyalkyl or polybutyl or polyisobutyl, a polyaminoalkylene radical of the general formula (V) wherein the radicals R3 are each the same or different and the radicals R4 are each identical or different and the radicals R3, R4 and R5 have the meanings given above, and m is an integer from 2 to 8, or a polyoxyalkylene radical of the general formula (VI) in which the R3 radicals can each be the same or different and have the above meaning, X represents alkyl or H and n represents an integer between 1 and 30, or wherein R1 and R2 together with the nitrogen atom to which they are attached represent a
  • the invention also relates to the use of polybutyl or polyisobutyl alcohols of the general formula (I) R - CH2 - OH (I) wherein R represents a polybutyl or polyisobutyl radical derived from isobutene and up to 20% by weight of n-butene, or the corresponding (poly) alkoxylates or esters of polybutyl or polyisobutyl alcohols in an amount effective as detergent in fuel or lubricant compositions, the Polybutyl or polyisobutyl alcohols are obtained by hydroformylation of reactive polybutenes or polyisobutenes in which more than 10% of the double bonds are ⁇ -permanent.
  • polybutyl or polyisobutyl alcohols to be used according to the invention and their (poly) alkoxylates or esters have excellent compatibility with detergents. They can be obtained in an extremely cost-effective manner by hydroformylation of polybutenes and hydrogenation of the oxo product. In contrast to the prior art, this gives products which are practically halogen-free (ie free of chlorine and bromine).
  • the relatively inexpensive functionalization of polybutene by means of the hydroformylation opens up a large number via the polybutyl alcohol of implementation options with the formation of valuable carrier substances which, especially in the case of (poly) alkoxylates and esters, also have detergent action.
  • the compounds in the fuel or lubricant compositions according to the invention are made from polybutenes, which preferably have a molecular weight M N from 324 to 3000, particularly advantageously from 378 to 1500.
  • the reactivity, ie the ⁇ - and ⁇ -olefin content of the polybutene, should be as high as possible.
  • Such polybutenes are generally obtained by polymerizing isobutene and isobutene-containing olefin cuts in the presence of BF3 and aluminum halides or alkylene. Low amounts of catalyst and short reaction times as described in DE-A-27 02 604 are preferred.
  • the hydroformylation can be carried out with conventional rhodium or cobalt catalysts at temperatures between 80 and 200 ° C, preferably 120 to 190 ° C, and CO / H2 pressures up to 600 bar, preferably 50 to 300 bar.
  • a two-step reaction is preferred, the first step being carried out at low temperatures, e.g. 120 ° C, and the second stage at high temperatures, e.g. 180 ° C, works.
  • the reactive double bonds are predominantly converted to aldehydes and ketones, while the hydrogenation only appears as a competitive reaction in the second stage.
  • With a sufficiently long reaction time a completely hydrogenated product with high proportions of polyisobutyl alcohol (70-90%) is obtained.
  • an inert solvent which can only absorb hydrogen to a limited extent and practically does not poison the hydroformylation catalyst.
  • Suitable solvents are e.g. Isoparaffins C8-C16.
  • the solvent is said to reduce the viscosity of the polyisobutene. It can be distilled off after the oxo reaction and the hydrogenation, but also only after further reactions such as alkoxylation or esterification, or in the case of the ashless dispersants against mineral oil, e.g. Solvent Neutral 100.
  • alkylene oxides to alcoholates in the presence of basic catalysts
  • ethylene oxide, propylene oxide or butylene oxide and mixtures thereof are technically important, but additions of compounds such as cyclohexene oxide are also conceivable.
  • What is particularly advantageous about this class of compounds is the good fuel and mineral oil compatibility due to the long, non-polar polyisobutyl residue.
  • the mineral oil compatibility which is only partially obtained with low molecular weight alcohols with butylene oxide, is of great interest.
  • the expensive butylene oxide can be replaced by cheaper ones Oxides can be substituted.
  • the amount of oxide added preferably depends on the compatibility with mineral oil, but should not exceed the molecular weight of the polyisobutene.
  • Another advantage of this polyisobutene modification is the drop in viscosity and thus, for example, a reduction in the tendency to "valve stick" when used as a fuel additive.
  • the esterification of polyisobutyl alcohol or alkoxylates is also carried out according to common methods. The end of the reaction is indicated by a falling OH number.
  • tri- and tetracarboxylic acids are of particular interest. When choosing the acid, the viscosity is generally taken into account by using an appropriate polyisobutyl alcohol.
  • Mono- and dicarboxylic acids permit the use of higher polyisobutyl alcohols or alkoxylates than tri- and tetracarboxylic acids.
  • the acids can also be used for synthesis in the form of their esters or anhydrides.
  • Suitable acids for the synthesis of ashless dispersants are di-, tri- and tetracarboxylic acids, which may only be partially esterified in order to introduce further polar groups with the aid of ammonia, amine and amide. Depending on the reaction conditions, the resulting amides, imides, ammonium or amine salts sometimes have excellent dispersing properties.
  • phthalic anhydride or trimellitic anhydride is reacted with polyisobutyl alcohol. The molar ratio is 1: 1. This process leads to products with high chemical uniformity.
  • the still free carboxylic acid groups e.g.
  • the polybutyl or polyisobutylamines of the general formula III proposed for combination in particular with the polyisobutyl alcohol can be prepared by using a corresponding polybutene or polyisobutene with a rhodium or cobalt catalyst in the presence of CO and H2 at temperatures between 80 and 200 ° C. and CO / H2 pressures of up to 600 bar hydroformylated and then a Mannich reaction or hydrogenating amination of the oxo product is carried out.
  • the amination reaction is expediently carried out at temperatures from 0 to 200 ° C. and pressures up to 600 bar, preferably 80 to 300 bar.
  • a suitable, inert solvent is expediently used in the production process in order to reduce the viscosity of the reaction mixture.
  • Low-sulfur aliphatic, cycloaliphatic and aromatic hydrocarbons are particularly suitable as solvents.
  • Aliphatic solvents which are free from sulfur compounds and contain less than 1% aromatics are particularly preferred.
  • So-called reactive polybutenes in particular polybutene A, B or C, are used.
  • a reactive polybutene is an unsaturated polymer with high chemical uniformity, with more than 10% of the double bonds being ⁇ -permanent.
  • DE-A-27 02 604 describes a way of producing such polybutenes.
  • a polymer prepared in this way contains approximately 60% ⁇ -olefin and 30% ⁇ -olefin, trisubstituted.
  • Medium-reactive polybutenes are usually obtained by polymerizing isobutene or isobutene-containing C4 sections with aluminum-containing catalysts, are chemically less uniform and contain only small amounts of ⁇ -olefin, usually below 10%.
  • the signals in C13 NMR show the difference.
  • the ⁇ -permanent, trisubstituted, chemically uniform proportion in polybutene B is approximately 40%, the ⁇ -olefin proportion approximately 10%.
  • polybutene A can be described as not very reactive and no longer has any notable chemically uniform proportions.
  • Particularly suitable polybutenes and polyisobutenes for the preparation of the polyamines according to the invention of the general formula I and the alcohols according to the invention of the general formula V are those which have an average degree of polymerization P of 10 to 100 and in which the proportion E of double bonds which are capable of reacting with maleic anhydride , Is 60 to 90%.
  • a value E 100% corresponds to the calculated theoretical value in the event that each molecule of the butene or isobutene polymer contains such a reactive double bond.
  • the value E is calculated for a reaction of the polyisobutene with maleic anhydride in a weight ratio of 5: 1 and for heating the mixture for 4 hours with stirring to 200 ° C. Further details can be found in GB-A-1 592 016, the disclosure of which is expressly incorporated herein by reference.
  • the polybutenes are commercial products.
  • the oxo product formed in the hydroformylation is normally in the form of an aldehyde / alcohol mixture. It can be further processed as a mixture or can be hydrated beforehand for reasons of storage stability. Hydrated products are less reactive.
  • polybutyl or polyisobutyl amines of the general formula III, in which the radicals R2 and R3 each represent hydrogen, are for the fuel sector, i.e. in the fuel compositions according to the invention, particularly suitable as a valve-cleaning or valve-cleaning additive in combination with the polyisobutyl alcohol and its derivatives.
  • the compounds to be used according to the invention are added to the fuels or lubricants in small amounts, generally in amounts of 0.005 to 0.5% by weight, preferably 0.01 to 0.1% by weight, based on the fuels or lubricants .
  • the rating is 714, which is in the range of good Mannich dispersants or those based on polyisobutenyl succinic anhydride.
  • the table shows that the combination of polybutyl alcohol and polybutylamine leads to excellent valve deposition values.
  • the polybutene used in this example is a highly reactive polybutene C which was produced in accordance with DE-A 2 702 604.

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (12)

  1. Composition de carburant ou de lubrifiant, caractérisée en ce qu'elle contient, en une quantité efficace en tant que détergent, au moins un alcool polybutylique ou polyisobutylique de formule générale (I)



            R - CH₂ - OH   (I)



    dans laquelle R représente un reste polybutyle ou polyisobutyle ayant un poids moléculaire M N de 324 à 3000, dérivé d'isobutène et, dans une proportion allant jusqu'à 20% en poids, de n-butène, ou un (poly)alcoxylate correspondant ou un ester carboxylique correspondant de l'alcool polybutylique ou polyisobutylique, l'alcool polybutylique ou polyisobutylique étant obtenu par hydroformylation de polybutènes ou polyisobutènes réactifs, dans lesquels plus de 10% des doubles liaisons sont en position α.
  2. Composition de carburant ou de lubrifiant selon la revendication 1, caractérisée en ce que le (poly)alcoxylate de l'alcool polybutylique ou polyisobutylique est un composé de formule générale (II)
    Figure imgb0019
     dans laquelle R a les significations données dans la revendication 1, n est mis pour un nombre entier de 2 à 8 et m représente un nombre entier de 1 à 200.
  3. Composition de carburant ou de lubrifiant selon la revendication 1, caractérisée en ce que dans le cas de l'ester de l'alcool polybutylique ou polyisobutylique, le composant acide dérive d'un acide mono-, di-, tri- ou tétracarboxylique aliphatique ou aromatique, saturé ou insaturé.
  4. Composition de carburant ou de lubrifiant selon la revendication 2, caractérisée en ce que le poly(alcoxylate) de l'alcool polybutylique ou polyisobutylique est préparé par réaction avec de l'oxyde d'éthylène, de propylène ou de butylène ou avec des mélanges de ceux-ci.
  5. Composition de carburant ou de lubrifiant selon la revendication 3, caractérisée en ce que le composant acide de l'ester de l'alcool polybutylique ou polyisobutylique est dérivé d'acides di-, tri- ou tétracarboxyliques qui ont été mis en réaction avec de l'ammoniac, des mono-, di-, tri-, tétra- ou polyamines pour donner les sels d'ammonium ou d'amine, les amides ou les imides correspondants ou des mélanges de ceux-ci.
  6. Composition de carburant ou de lubrifiant selon la revendication 3 ou 5, caractérisée en ce que le composant acide de l'ester de l'alcool polybutylique ou polyisobutylique est dérivé d'acide acétique, d'acide propionique, d'acide éthylhexanoïque, d'acide isononanoïque, d'acide succinique, d'acide adipique, d'acide maléique, d'acide phtalique, d'acide téréphtalique, d'acide citrique, d'acide trimellitique, d'acide trimésique, d'acide pyromellitique ou d'acide butanetétracarboxylique.
  7. Composition de carburant ou de lubrifiant selon l'une quelconque des revendications 1 à 6, contenant en plus au moins un additif azoté.
  8. Composition de carburant ou de lubrifiant selon l'une quelconque des revendications 1 à 7, contenant en plus de petites quantités d'au moins une polybutyl- ou polyisobutylamine de formule générale (III)
    Figure imgb0020
     dans laquelle R a la définition indiquée dans la revendication 1, et R¹ et R², qui peuvent être identiques ou différents, sont mis pour des atomes d'hydrogène, pour des restes hydrocarbonés aliphatiques ou aromatiques, pour des restes aminoalkylène ou des restes polyaminoalkylène primaires ou secondaires, aromatiques ou aliphatiques, pour des restes polyoxyalkylène, pour des restes hétéroaryle ou hétérocycliques, ou peuvent former ensemble, avec l'atome d'azote auquel ils sont reliés, un noyau dans lequel d'autres hétéroatomes peuvent être encore présents.
  9. Composition de carburant ou de lubrifiant selon la revendication 8, caractérisée en ce que dans la formule III, les restes R¹ et R² sont identiques ou différents et représentent chacun un atome d'hydrogène, un radical alkyle, aryle, hydroxyalkyle, un reste aminoalkylène de formule générale (IV)
    Figure imgb0021
    - dans laquelle R³ est mis pour un reste alkylène et R⁴ et R⁵, qui sont identiques ou différents, sont mis chacun pour un atome d'hydrogène, un reste alkyle, aryle, hydroxyalkyle ou polybutyle ou polyisobutyle -, un reste polyaminoalkylène de formule générale (V)
    Figure imgb0022
    - dans laquelle les restes R³ sont identiques ou différents et les restes R⁴ sont identiques ou différents, les restes R³, R⁴ et R⁵ ayant les significations données précédemment, et m est mis pour un nombre entier de 2 à 8 - ou un reste polyoxyalkylène de formule générale (VI)
    Figure imgb0023
    - dans laquelle les restes R³ peuvent être identiques ou différents et ont la signification donnée précédemment, X est mis pour un radical alkyle ou un atome d'hydrogène et n est un nombre entier entre 1 et 30
    - ou dans laquelle R¹ et R² représentent ensemble, avec l'atome d'azote auquel ils sont reliés, un reste morpholinyle, un reste pyridyle, un reste pipéridyle, un reste pyrrolyle, un reste pyrimidinyle, un reste pyrrolinyle, un reste pyrrolidinyle, un reste pyrazinyle ou un reste pyridazinyle.
  10. Composition de carburant ou de lubrifiant selon la revendication 1, contenant de 0,005 à 0,5% en poids des composés de formule I.
  11. Utilisation d'alcools polybutyliques ou polyisobutyliques de formule générale (I)



            R - CH₂ - OH   (I)



    dans laquelle R représente un reste polybutyle ou polyisobutyle dérivé d'isobutène et, dans une proportion allant jusqu'à 20% en poids, de n-butène, ou les (poly)alcoxylates ou esters correspondants des alcools polybutyliques ou polyisobutyliques, en une quantité efficace en tant que détergent dans des compositions de carburant ou de lubrifiant, les alcools polybutyliques ou polyisobutyliques étant obtenus par hydroformylation de polybutènes ou polyisobutènes réactifs, dans lesquels plus de 10% des doubles liaisons sont en position α.
  12. Esters et poly(alcoxylates) de l'alcool polybutylique ou polyisobutylique de formule générale VII



            R - CH₂ - O - R'   VII



    dans laquelle R représente un reste polybutyle ou polyisobutyle ayant un poids moléculaire M N de 324 à 3000, dérivé d'isobutène et, dans une proportion allant jusqu'à 20% en poids, de n-butène, R' est mis pour un reste acyle d'un acide mono ou polycarboxylique saturé ou insaturé, aliphatique ou aromatique, acyclique ou cyclique, ou avec l'atome d'oxygène pour un reste poly(alcoxylate) de formule
    Figure imgb0024
     dans laquelle n et m ont les significations données dans la revendication 2, l'alcool polybutylique ou polyisobutylique utilisé dans la préparation de l'ester et du poly(alcoxylate) ayant été obtenu par hydroformylation de polybutènes ou de polyisobutènes réactifs dans lesquels plus de 10% des doubles liaisons sont situées en ∝.
EP87119004A 1987-01-08 1987-12-22 Composition de carburant ou de lubrifiant, contenant des dérivés de polybutyl ou polyisobutyl Expired - Lifetime EP0277345B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3700363 1987-01-08
DE19873700363 DE3700363A1 (de) 1987-01-08 1987-01-08 Kraft- oder schmierstoffzusammensetzung und verwendung von polybutyl- oder polyisobutylderivaten in denselben

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EP0277345A1 EP0277345A1 (fr) 1988-08-10
EP0277345B1 true EP0277345B1 (fr) 1992-05-06

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Application Number Title Priority Date Filing Date
EP87119004A Expired - Lifetime EP0277345B1 (fr) 1987-01-08 1987-12-22 Composition de carburant ou de lubrifiant, contenant des dérivés de polybutyl ou polyisobutyl

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US (1) US4859210A (fr)
EP (1) EP0277345B1 (fr)
JP (1) JPS63175096A (fr)
DE (2) DE3700363A1 (fr)

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Also Published As

Publication number Publication date
DE3778866D1 (de) 1992-06-11
US4859210A (en) 1989-08-22
DE3700363A1 (de) 1988-07-21
EP0277345A1 (fr) 1988-08-10
JPS63175096A (ja) 1988-07-19

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