EP0115110B1 - Flüssige Brennstoffe und Korrosionsinhibitoren enthaltende Konzentrate - Google Patents

Flüssige Brennstoffe und Korrosionsinhibitoren enthaltende Konzentrate Download PDF

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Publication number
EP0115110B1
EP0115110B1 EP19830300440 EP83300440A EP0115110B1 EP 0115110 B1 EP0115110 B1 EP 0115110B1 EP 19830300440 EP19830300440 EP 19830300440 EP 83300440 A EP83300440 A EP 83300440A EP 0115110 B1 EP0115110 B1 EP 0115110B1
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Prior art keywords
aliphatic monocarboxylic
acid
component
liquid fuel
concentrate
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EP19830300440
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French (fr)
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EP0115110A1 (de
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Aubrey Lincoln Burrows
Paul Barry Mabley
Steven John Field
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Afton Chemical Ltd
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Afton Chemical Ltd
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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
    • 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
    • C10L1/188—Carboxylic acids; metal salts thereof
    • C10L1/1881—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
    • C10L1/1883—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom polycarboxylic acid
    • 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
    • C10L1/221—Organic compounds containing nitrogen compounds of uncertain formula; reaction products where mixtures of compounds are obtained
    • 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
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224—Amides; Imides carboxylic acid amides, imides

Definitions

  • metal corrosion caused by alcohol-type motor fuels is inhibited by adding to the fuel a combination of (A) polymerized polyunsaturated aliphatic monocarboxylic acid and (B) the reaction product of a polyalkylenepolyamine, a monounsaturated aliphatic monocarboxylic acid and, optionally, an alkenyl succinic anhydride.
  • the invention provides a liquid fuel adapted for use in an internal combustion engine said fuel comprising from 5 to 100 weight percent alcohol, from 0 to 95 weight percent gasoline and a corrosion inhibiting amount of a combination of (A) a polymer of one or more C 16 to C 18 , preferably a mainly C, 8 polyunsaturated aliphatic monocarboxylic acids and (B) a reaction product of (i) about one mole part of one or more polyalkylene polyaniihes having the formula wherein n is an integer from 1 to 8 the average value of n in a mixture of such polyamines preferably being from 2 to 5, and R is a divalent hydrocarbon group containing 2 to 4 carbon atoms, (ii) about 0.1 to 5 mole parts of one or more C 10 to C 24 , eg.
  • the 'combination' may be a simple mixture or as explained further hereafter, components A and B may react together.
  • the additive combination is useful in any alcohol-type motor fuel including gasoline- alcohol mixtures (e.g. "gasohol") as well as straight-alcohol type fuels.
  • Useful alcohols include methanol, ethanol, n-propanol, isopropanol, isobutanol and the like including alcohol mixtures.
  • Gasohol usually contains about 2 to 30 volume percent alcohol. At concentrations above 10 volume percent phase separation is a problem especially in the presence of water which is difficult to avoid. Phase separation can be minimized by including other oxygenates as co-solvents such as ethers, ketones, esters and the like.
  • An especially useful co-solvent is methyl tert-butyl ether (MTBE) which also increases octane value.
  • MTBE methyl tert-butyl ether
  • the additive combination may be used at a concentration which provides the required amount of corrosion protection.
  • a useful range is about 1 to 5000 p.p.m.
  • a more preferred range is about 5 to 2000 p.p.m. and the most preferred concentration is 10 to 500 p.p.m.
  • Component A is preferably a polymer of a polyunsaturated aliphatic monocarboxylic acid chiefly consisting of C 18 acid units. Examples of these are linoleic acid and linolenic acid including mixtures thereof.
  • the polymers comprise mainly dimers and trimers of the polyunsaturated acids. Suitable polymers of linoleic acid are available commercially. Mixtures high in trimer content are most preferred.
  • Component B is a reaction product of two or three reactants.
  • the first reactant is a polyalkylene polyamine.
  • These compounds have the structure in which n is an integer from 1-8 preferably with an average value in mixtures of 2-5.
  • R is a divalent hydrocarbon group containing 2-4 carbon atoms.
  • Examples of these reactants are ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine, propylene diamine, dipropylene triamine, tetrapropylene pentamine, butylene diamine and the like including mixtures thereof.
  • the more preferred alkylene polyamines are the polyethylene polyamines especially those in which n is an integer of 1-6 and most preferably mixtures of such polyethylene polyamines in which n has an average value of 2-4.
  • the second is a monounsaturated aliphatic monocarboxylic acid.
  • such acids containing 10-24 carbons have some utility, it has been found that superior results are achieved using 18 carbon acids or mixtures of acids mainly composed of C 18 acids, especially oleic acid, or commercial products high in oleic acid content such as tall oil fatty acids.
  • These acids can also be used in the form of their lower alkyl esters (e.g. methyl, ethyl, propyl, butyl) in which case the alcohol is displaced and distilled out during reaction.
  • the third reactant which is optional is an alkenyl succinic acid or anhydride, preferably an anhydride.
  • alkenyl succinic acid or anhydride preferably an anhydride.
  • the alkenyl group can vary over a wide range from 8-30 carbon atoms. Examples of these are octenyl, decenyl, dodecenyl, tetradecenyl, hexadecenyl, octadecenyl, eicosenyl, docosenyl, tetracosenyl, tri- acoulenyl and the like. More preferably, the alkenyl substituent contain 10-14 carbon atoms.
  • the alkenyl succinic reactant can also be used in the form of its lower alkyl ester but this is not the preferred mode.
  • the B component is made by reacting the above reactants in the ratio of one mole of polyalkylene polyamine: 0.1 to 5 moles of monounsaturated aliphatic monocarboxylic acid: 0 to 4 moles of alkenyl succinic anhydride; preferably the alkenyl succinic anhydride is used at a mole ratio of 0.5 to 3.5.
  • the reactants can be mixed altogether to provide a product formed in a single stage.
  • a preferred method of making the (B) component is in a first stage to react the monounsaturated aliphatic monocarboxylic acid with the polyalkylene polyamine; this reaction may preferably be carried out in an inert solvent such as hexane, benzene, xylene and the like at an elevated temperature. On completion of the first stage reaction, any remaining solvent is removed and the resultant product is a substance useful as the B component.
  • the first stage product is then further reacted in a second stage with the alkenyl succinic anhydride; this second stage reaction may be carried out in another or the same inert solvent, preferably in mineral oil, to yield a solution of a further product useful as the B component.
  • the reaction temperature in making the B component can vary over a wide range.
  • a useful range is about 40 to 200°C.
  • the reaction temperature in the first stage is high enough to distill out any water or alcohol displaced in the reaction.
  • a more preferred range in the first stage is 100 to 190°C.
  • component B is as follows: in a first stage of react 1 mole of triethylene tetramine with between 1 and 2 moles of commercial oleic acid in hexane at between 100 and 160°C to form primarily the amide. The water formed during the reaction is continually removed together with the hexane. On completion of the reaction, the product is cooled and reacted in a second stage with between 1.5 and 3 moles, of alkenyl succinic anhydride at between 75 and 100°C and at less than 150 mm Hg pressure for at least 1 hour; this second stage is preferably carried out using between 25 and 75 percent by weight of mineral oil as solvent.
  • a preferred method of forming the fuel compositions is to formulate the co-additives as a concentrate and then simply add the proper amount of the concentrate to the alcohol-type motor fuel.
  • the concentrate comprises a suitable inert solvent such as alcohols, ethers, esters, aromatic hydrocarbons and the like, and most preferably, aromatic hydrocarbons, such as toluene, xylene and the like, containing about 1 to 50 weight percent of the additive combination.
  • the two active components, A & B are preferably present in the ratios of between 1 part by weight of A to 10 parts by weight of B and 10 parts by weight of A to 1 part by weight of B. More preferably they are present in the ratios of between 1 part of A to 5 parts of B and 5 parts of A to 1 part of B.
  • any excess amine function and carboxylic acid function in the additive combination will probably exist as an amine salt. This is not detrimental and is considered as part of the invention as long as any such salt results from mixing the A and B components or from adding the A and B components to the fuel.
  • admixture of the additives may be in a refluxing solvent with the elimination of water so as to form a reaction product.
  • the coupons were removed from the fuel; after loose deposits were removed with a light brush, the coupons were washed and dried as at the start of the test and were then reweighed. Any change in coupon weight was recorded.
  • the corrosion was characterised by two modes, either weight loss by loss of metal or weight gain due to deposition of corrosion products, in the tests carried out below, visual examination of the coupons after test indicated that the two modes were mutually exclusive.
  • component A a polymer of a C 18 polyunsaturated aliphatic monocarboxylic acid which essentially comprised a trimer of linoleic acid and as component B, either component B1, a two stage reaction product of triethylene tetramine with oleic acid and C 12 alkenyl succinic anhydride or component B2, a ⁇ one stage reaction product of triethylene tetramine with oleic acid containing 6.0% nitrogen and having an acid value of 265 mg KOH/g (IP1 method).
  • component B1 a polymer of a C 18 polyunsaturated aliphatic monocarboxylic acid which essentially comprised a trimer of linoleic acid and as component B, either component B1, a two stage reaction product of triethylene tetramine with oleic acid and C 12 alkenyl succinic anhydride or component B2, a ⁇ one stage reaction product of triethylene tetramine with oleic acid containing 6.0% nitrogen and having an
  • component B1 was made as a 50% concentrate in mineral oil, which concentrate contained 2.5 percent nitrogen and had an acid value of 56 mg KOH/g (lPl method). The components were mixed together and added to the fuel as a concentrate in xylene.

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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)
  • Liquid Carbonaceous Fuels (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)

Claims (22)

1. Flüssiger Brennstoff, angepaßt an die Verwendung in einem Verbrennungsmotor, enthaltend von 5 bis 100 Gew.-% einen oder mehrere Alkohole, von 0 bis 95 Gew.-% Benzin und eine, die Korrosion inhibierende Menge einer Kombination aus (A), einem Polymer aus einer oder mehreren C16 bis C18 poly-ungesättigten aliphatischen Monocarbonsäuren und (B) ein Reaktionsprodukt aus (i) etwa einem Molteil aus einem oder mehreren Polyalkylenpolyaminen mit der Formel
Figure imgb0007
wobei n eine ganze Zahl zwischen 1 und 8 und R eine divalente Kohlenwasserstoffgruppe, enthaltend 2 bis 4 Kohlenstoffatome, bedeutet, (ii) etwa 0,1 bis 5 Molteile aus einer oder mehreren Cm bis C24 einfach ungesättigten aliphatischen Monocarbonsäuren oder deren niedrigere Alkyl- . ester und (iii) 0 bis etwa 4 Molteile von einem Alkenylsuccinanhydrid, wobei die Alkenylgrüppe 8 bis 30 Kohlenstoffatome aufweist.
2. Flüssiger Brennstoff nach Anspruch 1, worin die einfach ungesättigten aliphatischen Monocarbonsäuren oder ihre niedrigeren Alkylester, die zur Herstellung der Komponente B verwendet werden, in einer Menge von 0,5 bis 5 Molteilen vorliegen.
3. Flüssiger Brennstoff nach Anspruch 1 oder 2, worin die monoungesättigten aliphatischen Monocarbonsäuren oder ihre niedrigeren Ester, die zur Herstellung der Komponente B verwendet werden, 10 bis 20 Kohlenstoffatome aufweisen.
4. Flüssiger Brennstoff nach Anspruch 1 bis 3, worin in der Komponente (B) des Kombinationsreaktionsmittel (ii) eine Mischung der Polyalkylenpolyamine darstellt, so daß der durchschnittliche Wert von n 2 bis 5 beträgt.
5. Flüssiger Brennstoff nach Anspruch 1 bis 4, worin die Komponente (A) ein Polymer aus einer oder mehreren C,8 poly-ungesättigten aliphatischen Monocarbonsäuren ist.
6. Flüssiger Brennstoff nach Anspruch 1 bis 5, worin das Polymer hauptsächlich aus den Dimeren oder den Trimeren der poly-ungesättigten aliphatischen Monocarbonsäure oder Säuren oder Mischungen davon besteht.
7. Flüssiger Brennstoff nach Anspruch 1 bis 6, worin die aliphatische Monocarbonsäure, die zur Herstellung der Komponente (B) verwendet wird, eine C18 aliphatische Monocarbonsäure ist.
8. Flüssiger Brennstoff nach Anspruch 7, worin die poly-ungesättigte aliphatische Monocarbonsäure Linolsäure und die mono-ungesättigte aliphatische Säure Oleinsäure oder Tallölfettsäure ist.
9. Flüssiger Brennstoff nach Anspruch 1 bis 8, worin die Komponente (B) der Kombination ein Reaktionsprodukt aus (i), (ii) und von 0,5 bis 3,5 Molteilen der Alkenylsuccinsäure ist.
10. Flüssiger Brennstoff nach Anspruch 9, worin das Alkenylsuccinanhydrid, das zur Herstellung der Komponente (B) verwendet wird, ein C10-14 Alkenyl substituiertes Succinanhydrid ist.
11. Flüssiger Brennstoff nach Anspruch 10, worin das Alkenylsuccinanhydrid, das zur Herstellung der Komponente (B) verwendet wird, ein C12 Alkenyl-substituiertes Anhydrid ist.
12. Flüssiger Brennstoff nach Anspruch 1 bis 11, worin das zur Herstellung der Komponente (B) verwendete Polyalkylenpolyamin Polyethylenpolyamin ist.
13. Flüssiger Brennstoff nach Anspruch 9, worin man die Komponente (B) durch Reaktion in einem ersten Schritt bei einer Temperatur, die hoch genug ist, um das Wasser (i) zu verdrängen, von etwa 1 Molteil des Polyalkylenpolyamins und (ii) etwa 0,1 bis 5 Molteile der mono-ungesättigten aliphatischen Monocarbonsäure oder den niedrigeren Alkylestern über die Bildung eines Zwischenproduktes hergestellt und worin man anschließend in einem zweiten Schritt das Zwischenprodukt mit (iii) etwa 0,5 bis 3,5 Molteile Alkenylsuccinanhydrid umsetzt.
14. Korrosionsinhibitorkonzentrat, bestehend aus einem inerten Lösungsmittel, enthaltend 1 bis 50 Gew.-% einer Kombination aus (A), einem Polymer aus einer oder mehreren C16―C18 poly-ungesättigten aliphatischen Monocarbonsäuren und (B), einem Reaktionsprodukt aus (i) etwa einem Molteil aus einem oder mehreren Polyalkylenpolyamin mit der Formel
Figure imgb0008
wobei n eine ganze Zahl von 1 bis 8 und R eine divalente Kohlenwasserstoffgruppe mit 2 bis 4 Kohlenstoffatomen bedeutet, (ii) etwa 0,1 bis 5 Molteile von einer oder mehreren C10―C24 mono-ungesättigten aliphatischen Monocarbonsäuren oder den niedrigeren Alkylester davon und (iii) 0 bis etwa 4 Mol-Teile eines Alkenylsuccinanhydrids, wobei die Alkenylgruppe 8 bis 30 Kohlenstoffatome enthält-und worin das Gewichtsverhältnis von A:B von 1:10 bis 10:1 beträgt.
15. Konzentrat nach Anspruch 14, worin die mono-ungesättigten aliphatischen Monocarbonsäuren oder die niedrigeren Alkylester davon, die zur Herstellung der Komponente B verwendet werden, in einer Konzentration von 0,5 bis 5 Molteilen vorliegen.
16. Konzentrat nach Anspruch 14 oder 15, worin die mono-ungesättigten aliphatischen Monocarbonsäuren oder niedrigeren Alkylester davon, die zur Herstellung der Komponente B verwendet werden, 10 bis 20 C-Atome aufweisen.
17. Konzentrat nach Anspruch 14 bis 16, worin die Komponente (A) ein Polymer aus einer oder mehreren C,8 poly-ungesättigten aliphatischen Monocarbonsäuren ist.
18. Konzentrat nach Anspruch 14 bis 17, worin das Polymer hauptsächlich Dimere oder Trimere der poly-ungesättigten aliphatischen Monocarbonsäure oder Säuren oder Mischungen davon enthält.
19. Konzentrat nach Anspruch 14 bis 18, worin die aliphatische Monocarbonsäure, die zur Herstellung der Komponente (B) verwendet wird, eine C18 aliphatische Monocarbonsäure ist.
20. Konzentrat nach Anspruch 19, worin die poly-ungesättigte aliphatische Monocarbonsäure Linolsäure ist und die mono-ungsättigte aliphatische Säure Oleinsäure oder Tallölsäure ist.
21. Konzentrat nach Anspruch 14 bis 20, worin die Komponente (B) der Kombination ein Reaktionsprodukt aus (i), (ii) und 0,5 bis 3,5 Molteile eines C10-14 Alkenyl-substituierten Succinanhydrids darstellt.
22. Konzentrat nach Anspruch 14 bis 21, worin das Polyalkylenpolyamin Polyethylenpolyamin ist.
EP19830300440 1983-01-27 1983-01-27 Flüssige Brennstoffe und Korrosionsinhibitoren enthaltende Konzentrate Expired EP0115110B1 (de)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DE8383300440T DE3365202D1 (en) 1983-01-27 1983-01-27 Liquid fuels and concentrates containing corrosion inhibitors
EP19830300440 EP0115110B1 (de) 1983-01-27 1983-01-27 Flüssige Brennstoffe und Korrosionsinhibitoren enthaltende Konzentrate

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Application Number Priority Date Filing Date Title
EP19830300440 EP0115110B1 (de) 1983-01-27 1983-01-27 Flüssige Brennstoffe und Korrosionsinhibitoren enthaltende Konzentrate

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EP0115110B1 true EP0115110B1 (de) 1986-08-13

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US4780111A (en) * 1985-11-08 1988-10-25 The Lubrizol Corporation Fuel compositions
US20080086935A1 (en) * 2006-10-16 2008-04-17 Lawrence J Cunningham Method and compositions for reducing corrosion in engines combusting ethanol-containing fuels

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3304162A (en) * 1963-06-25 1967-02-14 Du Pont Stabilized fuel oil compositions
FR1483412A (fr) * 1965-06-15 1967-06-02 Basf Ag Procédé pour la production de dérivés d'acides organiques
FR2044305A5 (en) * 1969-05-14 1971-02-19 Inst Francais Du Petrole Nitrogen contng comps useful as fuel additivs
US4263014A (en) * 1978-06-23 1981-04-21 Texaco Inc. Anti-rust fuel composition
US4305730A (en) * 1980-02-19 1981-12-15 Texaco Inc. Corrosion-inhibited alcohol motor fuel composition

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EP0115110A1 (de) 1984-08-08

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