DE4404742A1 - Prepn. of high mol. wt. alkenyl carboxylic acids or their ester(s) - Google Patents

Prepn. of high mol. wt. alkenyl carboxylic acids or their ester(s)

Info

Publication number
DE4404742A1
DE4404742A1 DE4404742A DE4404742A DE4404742A1 DE 4404742 A1 DE4404742 A1 DE 4404742A1 DE 4404742 A DE4404742 A DE 4404742A DE 4404742 A DE4404742 A DE 4404742A DE 4404742 A1 DE4404742 A1 DE 4404742A1
Authority
DE
Germany
Prior art keywords
carbon
reaction
carboxylic acids
ester
alcohols
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.)
Withdrawn
Application number
DE4404742A
Other languages
German (de)
Inventor
Hans Dr Funke
Arthur Dr Hoehn
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to DE4404742A priority Critical patent/DE4404742A1/en
Priority to AU17058/95A priority patent/AU1705895A/en
Priority to ES95908911T priority patent/ES2146747T3/en
Priority to DE59508321T priority patent/DE59508321D1/en
Priority to AT95908911T priority patent/ATE192777T1/en
Priority to PCT/EP1995/000429 priority patent/WO1995021904A1/en
Priority to US08/687,582 priority patent/US5876467A/en
Priority to JP7520952A priority patent/JPH09509439A/en
Priority to DK95908911T priority patent/DK0745115T3/en
Priority to EP95908911A priority patent/EP0745115B1/en
Publication of DE4404742A1 publication Critical patent/DE4404742A1/en
Priority to NO19963398A priority patent/NO316276B1/en
Priority to FI963187A priority patent/FI963187A/en
Withdrawn legal-status Critical Current

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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
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    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
    • C07C51/14—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on a carbon-to-carbon unsaturated bond in organic compounds
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    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
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    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
    • 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
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Abstract

Carboxylic acids or their esters are prepd. by reacting C-contg. polymers with at least one C-C double bond with carbon monoxide and water or alcohols in the presence of a catalytic amt. of a Gp. 8-10 metal (cpd.) at 50-600 bar.

Description

Die vorliegende Erfindung betrifft ein verbessertes Verfahren zur Herstellung von Carbonsäuren oder Carbonsäureestern durch Umset­ zung von Polymeren mit mindestens 30 Kohlenstoffatomen, welche mindestens eine Kohlenstoff-Kohlenstoff-Doppelbindung tragen, mit Kohlenmonoxid und mit Wasser bzw. Alkoholen in Gegenwart kataly­ tischer Mengen eines Metalls oder einer Metallverbindung der Gruppen 8 bis 10 des Periodensystems.The present invention relates to an improved method for Production of carboxylic acids or carboxylic acid esters by conversion tion of polymers with at least 30 carbon atoms, which carry at least one carbon-carbon double bond, with Carbon monoxide and catalyzed with water or alcohols in the presence amounts of a metal or a metal compound Groups 8 to 10 of the periodic table.

Die EP-A-148 592 betrifft die Herstellung von Carbonsäureestern aus Polymeren, welche eine Kohlenstoff-Kohlenstoff-Doppelbindung tragen, mit Kohlenmonoxid und einem Alkohol in Gegenwart einer Protonensäure und eines Katalysators, der mindestens eines der Metalle Palladium, Rhodium, Ruthenium, Iridium und Cobalt sowie Kupfer enthält. Der Nachweis der Produkte erfolgte durch IR-Spek­ troskopie. Umsatz oder Selektivität dieser Reaktion läßt sich aus den Angaben der Druckschrift nicht entnehmen. Ein Nachstellen der beschriebenen Versuche ergab, daß der Umsatz zu den gewünschten Produkten weniger als 10% beträgt. Eine solche Ausbeute ist wirtschaftlich jedoch nicht akzeptabel.EP-A-148 592 relates to the production of carboxylic acid esters from polymers that have a carbon-carbon double bond wear, with carbon monoxide and an alcohol in the presence of a Protonic acid and a catalyst that at least one of the Metals palladium, rhodium, ruthenium, iridium and cobalt as well Contains copper. The products were verified by IR spec microscopy. The conversion or selectivity of this reaction can be determined do not refer to the information in the publication. A re-enactment of the described experiments showed that the conversion to the desired Products is less than 10%. Such a yield is economically not acceptable.

Die DE-A 29 12 489 beschreibt die Herstellung von Carbonsäure­ estern durch Hydroformylierung innenständiger Olefine, die maxi­ mal 20 Kohlenstoffatome tragen, in Gegenwart eines Kobaltkataly­ sators unter Drücken von 150 bis 300 bar.DE-A 29 12 489 describes the production of carboxylic acid esters by hydroformylation of internal olefins, the maxi times carry 20 carbon atoms, in the presence of a cobalt catalyst sators under pressures from 150 to 300 bar.

Es bestand die Aufgabe, ein Verfahren für die Herstellung von Carbonsäuren und Carbonsäureestern aus Polymeren, welche noch eine Kohlenstoff-Kohlenstoff-Doppelbindung tragen, bereitzustel­ len. Ein solches Verfahren soll es ermöglichen, die gewünschten Verfahrensprodukte bei gutem Umsatz in hoher Selektivität zu ge­ winnen.The task was to develop a process for the production of Carboxylic acids and carboxylic acid esters from polymers, which still carry a carbon-carbon double bond len. Such a process should enable the desired Process products with good sales in high selectivity win.

Demgemäß wurde das oben beschriebene Verfahren gefunden, das da­ durch gekennzeichnet ist, daß der Druck bei der Reaktion 50 bis 600 bar beträgt.We have found that this object is achieved by the process described above is characterized in that the pressure in the reaction 50 to Is 600 bar.

Als Katalysatoren im erfindungsgemäßen Verfahren dienen Metalle oder Metallverbindungen der Gruppen 8 bis 10 des Periodensystems. Diese können als Heterogen- oder bevorzugt als Homogenkataly­ satoren eingesetzt werden. Als Metallverbindungen kommen z. B. die Chloride, Acetate und Nitrate der genannten Metalle in Betracht, die Metalle können aber auch elementar eingesetzt werden. Bevor­ zugt werden Cobalt, Palladium und Rhodium sowie deren Verbindungen. Besonders bevorzugt sind Cobaltcarbonylverbindungen sowie Cobaltsalze.Metals serve as catalysts in the process according to the invention or metal compounds of groups 8 to 10 of the periodic table. These can be heterogeneous or preferably homogeneous sensors are used. As metal compounds such. B. the Chlorides, acetates and nitrates of the metals mentioned, the metals can also be used elementarily. Before  Cobalt, palladium and rhodium and their are added Links. Cobalt carbonyl compounds are particularly preferred and cobalt salts.

Die als Ausgangsmaterial zu verwendenden Polymeren tragen minde­ stens 30 Kohlenstoffatome sowie mindestens eine Kohlenstoff-Koh­ lenstoff-Doppelbindung. Bevorzugt sind Polymere mit einer Kohlen­ stoff-Kohlenstoff-Doppelbindung. Bevorzugt sind hiervon Kohlen­ wasserstoffpolymere, die aus aliphatischen Monoolefinen wie Ethylen, Propylen, n-Buten, iso-Buten, Hexen oder Mischungen die­ ser Monomeren aufgebaut sind. Die Molmassen betragen in der Regel 300 bis 7000. Besonders bevorzugt sind Polypropene und Polyisobu­ tene, die im allgemeinen Molmassen von 300 bis 3000, vorzugsweise 700 bis 1200 haben. Solche Verbindungen sind z. B. nach der EP-A-481 297 erhältlich. Propenoligomere können z. B. nach Chem. Lett., 1525 (1991) erhalten werden.The polymers to be used as starting material carry at least at least 30 carbon atoms and at least one carbon carbon lenstoff double bond. Polymers with a carbon are preferred fabric-carbon double bond. Coals are preferred hydrogen polymers made from aliphatic monoolefins such as Ethylene, propylene, n-butene, isobutene, hexene or mixtures of the these monomers are constructed. The molecular weights are usually 300 to 7000. Polypropenes and Polyisobu are particularly preferred tene, the generally molecular weights of 300 to 3000, preferably Have 700 to 1200. Such connections are e.g. B. after the EP-A-481 297 available. Propene oligomers can e.g. B. according to Chem. Lett., 1525 (1991).

Kohlenmonoxid wird in der Reaktion im Überschuß eingesetzt. Dabei wird das Verhältnis von Kohlenmonoxid zum Polymeren über den Partialdruck des Kohlenmonoxids eingestellt.Carbon monoxide is used in excess in the reaction. Here the ratio of carbon monoxide to the polymer over the Partial pressure of carbon monoxide set.

Das Polymer wird mit Kohlenmonoxid sowie mit Wasser bzw. einem Alkohol umgesetzt. Bei diesen Alkoholen handelt es sich in der Regel um primäre oder sekundäre aliphatische C₁- bis C₂₀-Alkohole wie Methanol, Ethanol, Isopropanol, n-Propanol, n-Butanol und 2-Ethylhexanol, weiterhin um C₂-C₃₀-Aminoalkohole wie 2-Dimethyl­ aminoethanol, 2-Diethylaminoethanol, 2-Di-iso-propylaminoethanol, 3-Dimethylamino-1-propanol, 3-Diethylamino-1-propanol, 3-Di-iso­ propylamino-1-propanol, 1-Dimethylamino-2-propanol, 1-Diethyl­ amino-2-propanol, 1-Di-iso-propylamino-2-propanol, 3-Dimethyl­ amino-1,2-propandiol, um araliphatische C₇-C₁₂-Alkohole wie Benzylalkohol, um aromatische C₆-C₁₀-Alkohole wie Phenol und um C₂-C₂₀-Mono- und Polyalkylenoxidglykole und -monoether wie Ethylenglykol, Ethylenglykolmonomethylether, Diethylenglykol, Diethylenglykolmonomethylether, Triethylenglykol, Triethylengly­ kolmonomethylether, Tetraethylenglykol und Tetraethylenglykolmo­ nomethylether. Im allgemeinen werden 1 bis 30 mol Wasser bzw. Alkohol, vorzugsweise 10 bis 25 mol pro Mol Polymerverbindung eingesetzt. Eine Umsetzung mit Wasser führt zur entsprechenden Säure, eine Umsetzung mit Alkoholen zu den Estern.The polymer is mixed with carbon monoxide and water or a Alcohol implemented. These alcohols are in the Rule around primary or secondary aliphatic C₁ to C₂₀ alcohols such as methanol, ethanol, isopropanol, n-propanol, n-butanol and 2-ethylhexanol, further C₂-C₃₀ amino alcohols such as 2-dimethyl aminoethanol, 2-diethylaminoethanol, 2-di-iso-propylaminoethanol, 3-dimethylamino-1-propanol, 3-diethylamino-1-propanol, 3-di-iso propylamino-1-propanol, 1-dimethylamino-2-propanol, 1-diethyl amino-2-propanol, 1-di-iso-propylamino-2-propanol, 3-dimethyl amino-1,2-propanediol, to araliphatic C₇-C₁₂ alcohols such as Benzyl alcohol, to aromatic C₆-C₁₀ alcohols such as phenol and um C₂-C₂₀ mono- and polyalkylene oxide glycols and monoethers such as Ethylene glycol, ethylene glycol monomethyl ether, diethylene glycol, Diethylene glycol monomethyl ether, triethylene glycol, triethylene glycol colmonomethyl ether, tetraethylene glycol and tetraethylene glycol mo nomethyl ether. In general, 1 to 30 mol of water or Alcohol, preferably 10 to 25 moles per mole of polymer compound used. A reaction with water leads to the corresponding one Acid, a reaction with alcohols to the esters.

Vorzugsweise wird das erfindungsgemäße Verfahren in Gegenwart stickstoffhaltiger Basen durchgeführt. Als besonders geeignet ha­ ben sich dabei tertiäre aromatische Amine wie Pyridin oder Pico­ line herausgestellt. Diese Basen können im molaren Verhältnis von 1 : 1 bis 50 : 1, vorzugsweise 2 : 1 bis 15 : 1, bezogen auf das kataly­ tisch aktive Metall, verwendet werden.The process according to the invention is preferably carried out in the presence nitrogenous bases performed. As particularly suitable ha there are tertiary aromatic amines such as pyridine or pico line exposed. These bases can be in a molar ratio of  1: 1 to 50: 1, preferably 2: 1 to 15: 1, based on the kataly table active metal.

In der Regel beträgt das molare Verhältnis des Polymeren zum ka­ talytisch aktiven Metall 2 : 1 bis 50 : 1, vorzugsweise 4 : 1 bis 15 : 1. Die Reaktion kann in einem Lösungsmittel ausgeführt werden. Dabei handelt es sich im allgemeinen um polare Lösungsmittel wie Ace­ ton, Ether wie Tetrahydrofuran, aber auch um die in der Reaktion als Reaktionspartner auftretenden Alkohole oder Wasser. Diese Lö­ sungmittel können auch im Gemisch mit Kohlenwasserstoffen wie Alkanen verwendet werden. Die Menge des Lösungsmittels liegt im allgemeinen bei 10 bis 90 Gew.-%, bezogen auf den Gesamtansatz.As a rule, the molar ratio of polymer to ka is analytically active metal 2: 1 to 50: 1, preferably 4: 1 to 15: 1. The reaction can be carried out in a solvent. Here they are generally polar solvents such as Ace clay, ethers such as tetrahydrofuran, but also those in the reaction alcohols or water occurring as reactants. This Lö Solvents can also be mixed with hydrocarbons such as Alkanes can be used. The amount of solvent is generally at 10 to 90 wt .-%, based on the total batch.

Die Reaktion kann bei Temperaturen von 20 bis 300°C, vorzugsweise bei 100 bis 200°C durchgeführt werden. Der Reaktionsdruck beträgt 50 bis 600 bar, bevorzugt ist der Bereich von 100 bis 300 bar ab­ soluten Drucks. Die Reaktionszeiten betragen im allgemeinen 5 bis 48 Stunden. Zur Durchführung der Reaktionen werden die Reaktions­ partner vermischt und anschließend unter CO-Druck auf die Reakti­ onstemperatur gebracht. Die Aufarbeitung kann in an sich bekann­ ter Weise durch Abtrennung des Katalysators, Abdestillieren des Lösungsmittels sowie chromatographische Reinigung des Reaktions­ produktes erfolgen.The reaction can be carried out at temperatures of 20 to 300 ° C, preferably be carried out at 100 to 200 ° C. The reaction pressure is 50 to 600 bar, the range from 100 to 300 bar is preferred soluten Drucks. The reaction times are generally 5 to 48 hours. To carry out the reactions, the reaction partner mixed and then under CO pressure on the reacti brought on temperature. The processing can be known in itself ter way by separating the catalyst, distilling off the Solvent and chromatographic purification of the reaction product.

Die Reaktion kann kontinuierlich oder diskontinuierlich ausge­ führt werden.The reaction can be carried out continuously or batchwise leads.

Das erfindungsgemäße Verfahren erlaubt die Herstellung der Verfahrensprodukte mit hoher Selektivität bei gutem Umsatz.The inventive method allows the production of Process products with high selectivity and good sales.

Die Verfahrensprodukte finden als Zusätze zu Schmierstoffen und Kraftstoffen für Diesel- und Ottomotoren Verwendung.The process products are found as additives to lubricants and Fuels for diesel and petrol engines use.

Beispielexample Herstellung von PolyisobutylcarbonsäuremethylesterProduction of polyisobutylcarboxylic acid methyl ester

In einem Autoklaven wurden 900 g Polyisobuten (Molmasse 1100; 0,82 mol), 19,2 g Dicobaltoktacarbonyl (56 mmol), 168 g 3-Picolin (1,8 mol), 600 g Methanol (18,8 mol) und 900 g eines C₁₀- bis C₁₃-Alkangemisches vorgelegt. Es wurde ein Druck von 50 bar CO aufgepreßt. Der Autoklav wurde auf 180°C erhitzt und der CO-Druck auf 270 bar gesteigert. Nach 24 Stunden wurde Luft eingeleitet, um den Katalysator zu entfernen, das Lösungsmittel sowie das Pi­ colin wurden destillativ abgetrennt und es verblieben 920 g eines viskosen Produktes, das 71% Polyisobutylcarbonsäuremethylester enthielt. Der Umsatz betrug 80%, die Selektivität 89%. Mit Pentan als Lösungsmittel ließ sich der Ester chromatographisch an Kieselgel vom nichtumgesetzten Edukt abtrennen.900 g of polyisobutene (molar mass 1100; 0.82 mol), 19.2 g dicobalt octacarbonyl (56 mmol), 168 g 3-picoline (1.8 mol), 600 g of methanol (18.8 mol) and 900 g of a C₁₀ bis C₁₃-alkane mixture submitted. A pressure of 50 bar CO pressed on. The autoclave was heated to 180 ° C and the CO pressure increased to 270 bar. Air was introduced after 24 hours, to remove the catalyst, the solvent and the Pi colin was separated off by distillation and 920 g of one remained viscous product, the 71% polyisobutylcarboxylic acid methyl ester  contained. The conversion was 80%, the selectivity 89%. With The ester was chromatographed on pentane as solvent Separate silica gel from the unreacted starting material.

Claims (4)

1. Verfahren zur Herstellung von Carbonsäuren oder Carbonsäure­ estern durch Umsetzung von Polymeren mit mindestens Kohlenstoffatomen, welche mindestens eine Kohlenstoff-Koh­ lenstoff-Doppelbindung tragen, mit Kohlenmonoxid und mit Was­ ser bzw. Alkoholen in Gegenwart katalytischer Mengen eines Metalls oder einer Metallverbindung der Gruppen 8 bis 10 des Periodensystems, dadurch gekennzeichnet, daß der Druck bei der Reaktion 50 bis 600 bar beträgt.1. A process for the preparation of carboxylic acids or carboxylic esters by reacting polymers having at least carbon atoms which carry at least one carbon-carbon len double bond with carbon monoxide and with water or alcohols in the presence of catalytic amounts of a metal or a metal compound of groups 8 to 10 of the periodic table, characterized in that the pressure during the reaction is 50 to 600 bar. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man Cobalt-, Palladium- oder Rhodiumkatalysatoren verwendet.2. The method according to claim 1, characterized in that one Cobalt, palladium or rhodium catalysts are used. 3. Verfahren nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß man Polyisobuten als Polymerkomponente verwendet.3. The method according to claim 1 or 2, characterized in that to use polyisobutene as the polymer component. 4. Verfahren nach den Ansprüchen 1 bis 3, dadurch gekennzeich­ net, daß man die Reaktion in Gegenwart einer stickstoffhalti­ gen Base vornimmt.4. The method according to claims 1 to 3, characterized in net that the reaction in the presence of a nitrogen-containing base.
DE4404742A 1994-02-15 1994-02-15 Prepn. of high mol. wt. alkenyl carboxylic acids or their ester(s) Withdrawn DE4404742A1 (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
DE4404742A DE4404742A1 (en) 1994-02-15 1994-02-15 Prepn. of high mol. wt. alkenyl carboxylic acids or their ester(s)
PCT/EP1995/000429 WO1995021904A1 (en) 1994-02-15 1995-02-07 Use of carboxylic acid esters as fuel or lubricant additives and process for preparing the same
ES95908911T ES2146747T3 (en) 1994-02-15 1995-02-07 USE OF CARBOXYL ACID ESTERS AS FUEL OR LUBRICANT ADDITIVES AND A PROCEDURE FOR THEIR PREPARATION.
DE59508321T DE59508321D1 (en) 1994-02-15 1995-02-07 USE OF CARBONIC ACID ESTERS AS A FUEL OR LUBRICANT ADDITIVE AND A METHOD FOR THE PRODUCTION THEREOF
AT95908911T ATE192777T1 (en) 1994-02-15 1995-02-07 USE OF CARBOXIC ACID ESTERS AS FUEL OR LUBRICANT ADDITIVES AND A METHOD FOR THE PRODUCTION THEREOF
AU17058/95A AU1705895A (en) 1994-02-15 1995-02-07 Use of carboxylic acid esters as fuel or lubricant additives and process for preparing the same
US08/687,582 US5876467A (en) 1994-02-15 1995-02-07 Use of carboxylic esters as fuel additives or lubricant additives and their preparation
JP7520952A JPH09509439A (en) 1994-02-15 1995-02-07 Use of Carboxylic Acid Ester as Fuel Additive or Lubricating Oil Additive and Process for Producing the Same
DK95908911T DK0745115T3 (en) 1994-02-15 1995-02-07 Use of carboxylic acid esters as fuel or lubricant additives and a process for their preparation
EP95908911A EP0745115B1 (en) 1994-02-15 1995-02-07 Use of carboxylic acid esters as fuel or lubricant additives and process for preparing the same
NO19963398A NO316276B1 (en) 1994-02-15 1996-08-14 Use of carboxylic acid esters as fuel or lubricant additives, as well as lubricant and fuel compositions
FI963187A FI963187A (en) 1994-02-15 1996-08-14 Use of carboxylic acid esters as additives in fuels or lubricants and method for their preparation

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997048738A1 (en) * 1996-06-17 1997-12-24 Exxon Chemical Patents Inc. Carboxylic amide-containing polymers for use as fuel or lubricating oil additives and processes for their preparation
WO1998012235A1 (en) * 1996-09-20 1998-03-26 Basf Aktiengesellschaft Hydroformylation process

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997048738A1 (en) * 1996-06-17 1997-12-24 Exxon Chemical Patents Inc. Carboxylic amide-containing polymers for use as fuel or lubricating oil additives and processes for their preparation
WO1998012235A1 (en) * 1996-09-20 1998-03-26 Basf Aktiengesellschaft Hydroformylation process
US6331656B1 (en) 1996-09-20 2001-12-18 Basf Aktiengesellschaft Hydroformylation process

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