EP0398100B1 - Compositions de combustible contenant des produits d'alkoxylation - Google Patents

Compositions de combustible contenant des produits d'alkoxylation Download PDF

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Publication number
EP0398100B1
EP0398100B1 EP90108498A EP90108498A EP0398100B1 EP 0398100 B1 EP0398100 B1 EP 0398100B1 EP 90108498 A EP90108498 A EP 90108498A EP 90108498 A EP90108498 A EP 90108498A EP 0398100 B1 EP0398100 B1 EP 0398100B1
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EP
European Patent Office
Prior art keywords
oxo
oils
fuel
alkoxylation products
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.)
Expired - Lifetime
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EP90108498A
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German (de)
English (en)
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EP0398100A1 (fr
Inventor
Hans Peter Dr. Rath
Herwig Dr. Hoffmann
Volker Dr. Vogt
Hans Dr. Horler
Helmut Dr. Mach
Jürgen Dr. Thomas
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BASF SE
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BASF SE
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
    • C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/146—Macromolecular compounds according to different macromolecular groups, mixtures thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)

Definitions

  • the invention relates to fuels for internal combustion engines with improved properties, containing alkoxylation products, by the reaction of oxo oils, fractions of these oxo oils or partially esterified carboxylic acids with oxo oils or oxo oil fractions, with alkylene oxides with 2 to 4 carbon atoms, in particular with propene oxide and / or butene oxides and / or be obtained in minor amounts of ethene oxide.
  • the invention relates to fuel compositions for gasoline engines.
  • additive packages are added to gasoline in amounts of up to 2,500 mg / kg. These mostly consist of fuel detergents, corrosion inhibitors, oxidation inhibitors, anti-icing agents, carrier oils and solvents.
  • Carrier oils primarily have the task of preventing the so-called valve plugging and ensuring a better distribution of the detergents.
  • polyethers and esters as carrier oils should reduce the increase in the octane requirement of engines with increasing number of operating hours and ultimately set the lowest possible level of octane requirement.
  • esters as a gasoline additive has long been known and is described, for example, in DE-OS 21 29 461, DE-OS 19 64 785, DE-OS 23 16 535 or GB 21 17 468.
  • Esters with more than 35 carbon atoms have a particularly good effect, particularly when the alcohol component is highly branched, ie has been prepared by oxidizing oligomers of propene and butenes, in particular of n-butenes.
  • aromatic tri- and tetracarboxylic acids are used, relatively short-chain alcohols can be used to achieve the desired molecular weight in acceptable condensation times and with normal catalyst removal.
  • the high price of these poorly accessible acids is a serious economic disadvantage.
  • aromatic dicarboxylic acids such as phthalic acid is far more economical, but long-chain alcohols which are difficult to access are then required for the preparation of effective esters. High condensation temperatures give acceptable condensation times, but processing is very difficult and time-consuming.
  • alkene oxide-based polyethers have also been known for a long time and e.g. described in DE-OS 21 29 461. Alkene oxides such as propene oxide and butene oxides are preferred here. However, only special polyethers containing predominantly butene oxides are infinitely miscible with polyisobutene and polyisobutene derivatives. Butene oxides are only available to a limited extent and the market price is correspondingly high.
  • the task was therefore to synthesize a highly effective, at least equivalent carrier oil at significantly lower costs and to avoid the disadvantages of ester synthesis with complete esterification or polyether production with an excess of alkoxide.
  • alkoxylation products from reaction products of alkene oxides with oxo oils, oxo oil fractions and carboxylic acids partially esterified with oxo oils combine all the advantages of esters and / or polyethers, and the cost of starting materials can be drastically reduced.
  • the products are excellent carrier oils with partly high molecular weight, whereby up to 30% of the usual detergents can be saved without the gasoline quality, i.e. the purifying effect in the intake and mixture formation system deteriorates.
  • the invention relates to fuel compositions which contain small amounts, e.g. Contain 0.005 to 0.2% by weight of alkoxylation products, obtainable by reacting alkylene oxides with 2 to 4 carbon atoms, in particular propene oxide and / or butene oxides and / or in minor amounts of ethene oxide with oxo oils, oxo oil fractions or carboxylic acids partially esterified with oxo oils or oxo oil fractions, where the oxo oils are distillation residues from the production of oxo alcohols with more than 8 carbon atoms and the molar ratio of the alkylene oxides to the OH groups and free carboxyl groups in the oxo oil or ester is preferably from 0.2 to 30.
  • the amount of alkoxides must be at least so large that all free carboxyl groups are alkoxylated, i.e. a molar ratio of alkene oxide to carboxyl groups of at least 2.
  • alkene oxides In the preparation of the alkoxylation products, propene oxide and butene oxides, in particular 1,2-butene oxide, are preferred as alkene oxides.
  • ethene oxide can also be incorporated in minor amounts, for example up to 50 mol%, based on the total amount of carboxyl and hydroxyl groups, as long as this does not impair the compatibility of the components of gasoline additive packages. This is the case in particular in the case of production according to Example D.
  • the use of pure ethylene oxide may even be economical here.
  • the reaction with alkene oxides takes place in a manner known per se and is described, for example, in DE patent application P 38 26 608.3, preparation example 1.
  • the oxo oils or fractions used are distillation residues from the production of oxo alcohols with more than 8 carbon atoms.
  • the oxo alcohols on which the oxo oils are based should in particular be branched with 13, 17, 21, 25, 29 and 33 carbon atoms and derive from oligomers of propene and from butenes, in particular from n-butenes, in order to ensure that the oxo oils are in a liquid state at room temperature.
  • a low melting point well below zero ° C is an advantage, since the oxo oil behaves largely like its alcohol in this respect.
  • the oxo oils are mixtures of substances with far more than 20 compounds, some of which are only isomers.
  • the oxo oil of a di-butene contains acids, nonanols, decanediols, di-isononyl ethers, isononanoic acid nyl esters and large amounts of ether alcohols of the empirical formula C19H40O2.
  • the ether alcohols of the oxo oils have the general formula C 2n + 1 H 4n + 2 O2, where n stands for the number of carbon atoms of the oxo alcohol.
  • ether alcohols are probably produced by etherification of a diol with an alcohol, ie in the case of dibutene from decanediol and nonanol. This leads to the presumed general formula of ether alcohol: where n has the aforementioned meaning and generally means the numbers 9 to 33.
  • ether alcohols are usually present in the oxo oils in amounts of 30-60% and can optionally be separated off by distillation. For economic reasons, however, isolation of the ether alcohols with subsequent esterification and / or etherification is not recommended for the present application, unless there are qualitative reasons for this.
  • the partial esterification of the previously characterized oxo oils or oxo oil fractions can be carried out according to conventional esterification processes with aliphatic and aromatic carboxylic acids.
  • Suitable aliphatic carboxylic acids are isononanoic acid, succinic acid, maleic acid and adipic acid, but also carboxylic acid mixtures, such as the dicarboxylic acid mixture of the production of adipic acid (mixture of adipic acid, succinic acid and glutaric acid) or the stripping acid of cyclohexane oxidation (mixture of adipic acid) and hydroxyapronic acid and hydroxyapronic acid.
  • Aromatic di-, tri- or tetracarboxylic acids are o-phthalic acid, isophthalic acid, terephthalic acid, trimesic acid, trimellitic acid, pyromellitic acid and benzene tetracarboxylic acid.
  • Esterification with acid anhydrides is particularly preferred.
  • the acids or acid anhydrides are generally added during the esterification in amounts of 0.5 to 1.3 equivalents based on the hydroxyl number and with acid catalysts, such as titanium acid esters, but also without a catalyst at temperatures of 150 to 250 ° C. under vacuum or with Fumigation with nitrogen esterified.
  • Processing by neutralization and washing is carried out according to conventional methods.
  • the oxo oils are preferably esterified in the presence of KOH with 0.4 to 0.6 mol of phthalic anhydride, based on the OH number, and the condensation is terminated at acid numbers between 10 and 50 and, as described above, with alkene oxides without further KOH addition or drainage. In this way, time and cost-intensive neutralization and washing steps are avoided and alkene oxide consumption is minimized.
  • Fuels for internal combustion engines are organic, mostly hydrocarbon-containing liquids that are suitable for the operation of Otto, Wankel and diesel engines.
  • hydrocarbons from coal hydrogenation hydrocarbons from coal hydrogenation, alcohols of various origins and compositions and ethers such as Methyl tertiary butyl ether contained therein.
  • the admissible mixtures are mostly nationally defined worldwide.
  • the alkoxylation products to be used according to the invention are usually the fuels together with fuel detergents, such as amines of oleic acid or ethylenediaminetetraacetic acid according to EP-A-6527, or the polyisobutenylsuccinic acid furthermore polyether polyamine carbamates, and in particular polybutenamines, obtained by reacting the alcohols or the corresponding halogen compounds with NH3 , Aminoethylethanolamine, dimethylaminopropylamine, triethylene tetramine or tetraethylene pentamine, as described in US Pat. No.
  • fuel detergents such as amines of oleic acid or ethylenediaminetetraacetic acid according to EP-A-6527
  • polyisobutenylsuccinic acid furthermore polyether polyamine carbamates, and in particular polybutenamines, obtained by reacting the alcohols or the corresponding halogen compounds with NH3 , Aminoethylethanolamine
  • corrosion inhibitors which are mostly low molecular weight compounds with amide and / or ammonium and / or amine and / or acid groups or triazole and imidazole derivatives, furthermore phenolic or aminic antioxidants, such as di-tert-butylphenol or para-phenylenediamine, and finally freezing inhibitors, such as alcohols or diols.
  • the combination of the alkoxylation products to be used according to the invention with polybutenamines is preferred, the quantitative ratio of the alkoxylation products to the polybutenamines generally being 1: 2 to 3: 1.
  • a carrier oil combination with polyethers or mineral oil is also possible; this enables a reduction in the proportion of the alkoxylation products in relation to the polybutenamines, polyetherpolyamine carbamates or amides.
  • the distillation residue of a C9-oxo alcohol, obtained from the cobalt-catalyzed oxidation of dibutene, is used to produce the alkoxylation product.
  • the dibutene is produced from the so-called raffinate II, a mixture of approximately 30% butanes, 45% butene-1 and 25% cis and trans-butene-2.
  • 1,000 g of this distillation residue which has an OH number of 132, an acid number of 10, a density of 0.872 g / cm3 at 20 ° C and a viscosity of 27 mm2 / s at 20 ° C, are in a stirred tank with 5 g of KOH flakes are added, the reaction vessel is flushed with nitrogen, evacuated to 10 mbar and heated to 120 ° C. under vacuum and the mixture is stirred for 2 hours. At 1.1 bar nitrogen pressure, the mixture is heated to 160 to 170 ° C. and 1,000 g of 1,2-butene oxide are gassed in so slowly that a pressure of 4.5 bar is not exceeded.
  • the polyether-containing mixture obtained has an OH number of 75, a density of 0.917 g / cm3 at 20 ° C and a viscosity of 71 mm2 / s at 20 ° C.
  • the procedure is as in Preparation A, but 400 g of distillation residue, 2 g of KOH flakes and 1,600 g of 1,2-butene oxide are used.
  • the product has an OH number of 37, a density of 0.948 g / cm3 at 20 ° C and a viscosity of 385 mm2 / s at 20 ° C.
  • an ether alcohol C21H44O2 is isolated by distillation and analogous to Preparation A with a mixture of 1,2-propene oxide and 1,2-butene oxide implemented.
  • the OH number of the alcohol is 171, its density at 20 ° C 0.87 g / cm3 and its viscosity at 20 ° C 75 mm2 / s.
  • 500 g of the ether alcohol, 2.5 g of KOH, 500 g of 1,2-propene oxide and 1,000 g of 1,2-butene oxide are used for the reaction.
  • the OH number of the reaction product is 48, its viscosity at 20 ° C was 320 mm2 / s.
  • the following table shows the effect of known carrier oils and the alkoxylation products to be used according to the invention in combination with known detergents in gasoline for internal combustion engines.
  • the quantities shown in the table were added unleaded premium petrol (RON 95; DIN 51 607) and tested in test bench tests with a 1.2 Opel Kadett engine in accordance with CEC-F-02-T-79.
  • the reference oil RL 51 was used as engine oil.
  • the table shows a significantly better effect of the alkoxylation products according to the invention compared to the prior art, i.e. less deposits on the intake valves of the 1.2 l Opel Kadett engine.
  • the carrier oils to be used according to the invention were combined with commercially available polybutenamine, produced from polybutene MG 1300 and aminoethylethanolamine, active substance content 50%.
  • the recommended dosage of the commercial polybutenamine for formulations with mineral oil is 350 mg / kg.
  • the carrier oils according to the invention enable a saving of about 30% in polymeric detergents. Results with other higher viscosity detergents are comparable.
  • Another advantage of the new carrier oils is their compatibility with polyisobutene with a molecular weight of 800 to 2,000, which is contained in most of the detergents used for gasoline additives.
  • Propene oxide-based polyethers are not very compatible; i.e. higher amounts of solvent are required to produce an additive package.
  • the carrier oils according to the invention are significantly cheaper to produce than polyethers, especially if the latter are produced on the basis of butene oxide based on polyisobutene. Since the substance mixtures contain a number of low molecular weight compounds, particularly in the case of partial esterification, they are more suitable for combating valve plugging than pure polyethers with higher molecular weights.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lubricants (AREA)
  • Liquid Carbonaceous Fuels (AREA)

Claims (11)

1. Carburants pour moteurs à combustion interne, contenant de petites quantités de produits d'alcoxylation, pouvant être obtenus par réaction d'oxydes d'alkylène à 2-4 atomes de carbone avec des huiles oxo, des fractions des huiles oxo ou des acides carboxyliques partiellement estérifiés avec des huiles oxo au des fractions des huiles oxo, les huiles oxo étant des résidus de distillation de la préparation d'alcools oxo contenant plus de 8 atomes de carbone.
2. Carburants pour moteurs à combustion interne, contenant de petites quantités de produits d'alcoxylation, selon la revendication 1, pouvant être obtenus par réaction d'oxyde de propylène et/ou d'oxyde de butylène et/ou, en faibles quantités, d'oxyde d'ethylène avec des huiles oxo, des fractions d'huiles axa au des acides carboxyliques partiellement estérifiés avec des huiles oxo ou des fractions d'huiles oxo, les huiles oxo étant des résidus de distillation de la préparation d'alcools oxo contenant plus de 8 atomes de carbone.
3. Carburants selon la revendication 1, caractérisés en ce qu'ils contiennent de 0,002 à 0,2% en poids des produits d'alcoxylation.
4. Carburants selon la revendication 1, caractérisés en ce que le rapport molaire des oxydes d'alkylène aux groupements OH et aux groupements carboxyle libres dans l'ester au l'huile oxo peut aller jusqu'à 30, et en ce qu'il est, aux groupements carboxyle libres, d'au moins 2.
5. Carburants selon la revendication 1, caractérisés en ce que les huiles oxo se composent, pour plus de 50% en poids, d'un éther-alcool qui comporte un groupement éther et un groupement alcool et renferme 2 n + 1 atomes de carbone, n désignant le nombre des atomes de carbone de l'alcool oxo et étant cOmpris entre 9 et 33.
6. Carburants selon la revendication 1, caractérisés en ce que les huiles oxo sont des résidus de distillation de la préparation d'alcools oxo à partir d'oligomères du propylène et/ou de butylènes.
7. Carburants selon la revendication 1, caractérisés en ce que les huiles oxo sont des résidus de distillation d'alcools oxo d'oligomères des n-butylènes.
8. Carburants selon la revendication 1, caractérisés en ce que les fractions d'huiles oxo sont des éther-alcools isolés de l'huile oxo.
9. Carburants selon la revendication 1, caractérisés en ce que les produits d'alcoxylation sont ceux d'acides carboxyliques partiellement estérifiés avec des huiles oxo ou avec des éther-alcools obtenus à partir de celles-ci.
10. Carburants selon la revendication 8, caractérisés en ce que des mélanges d'acide carboxyliques sont utilisés pour l'estérification partielle.
11. Carburants selon la revendication 1, caractérisés en ce qu'ils contiennent, en dehors des produits d'alcoxylation, des détergents, des produits antigivrage, des inhibiteurs de corrosion et des antioxydants.
EP90108498A 1989-05-19 1990-05-07 Compositions de combustible contenant des produits d'alkoxylation Expired - Lifetime EP0398100B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3916365A DE3916365A1 (de) 1989-05-19 1989-05-19 Kraftstoffzusammensetzungen mit einem gehalt an alkoxylierungsprodukten
DE3916365 1989-05-19

Publications (2)

Publication Number Publication Date
EP0398100A1 EP0398100A1 (fr) 1990-11-22
EP0398100B1 true EP0398100B1 (fr) 1992-08-19

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EP90108498A Expired - Lifetime EP0398100B1 (fr) 1989-05-19 1990-05-07 Compositions de combustible contenant des produits d'alkoxylation

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US (1) US5123932A (fr)
EP (1) EP0398100B1 (fr)
CA (1) CA2016885A1 (fr)
DE (2) DE3916365A1 (fr)

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DE59000262D1 (de) 1992-09-24
US5123932A (en) 1992-06-23
EP0398100A1 (fr) 1990-11-22
CA2016885A1 (fr) 1990-11-19
DE3916365A1 (de) 1990-11-22

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