EP0613938B1 - Stickstoff enthaltende Dispergiermittel umfassende Kohlenwasserstoffkraftstoffszusammensetzungen - Google Patents

Stickstoff enthaltende Dispergiermittel umfassende Kohlenwasserstoffkraftstoffszusammensetzungen Download PDF

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EP0613938B1
EP0613938B1 EP94301303A EP94301303A EP0613938B1 EP 0613938 B1 EP0613938 B1 EP 0613938B1 EP 94301303 A EP94301303 A EP 94301303A EP 94301303 A EP94301303 A EP 94301303A EP 0613938 B1 EP0613938 B1 EP 0613938B1
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hydrocarbon fuel
hydrocarbyl
composition according
fuel composition
diamide
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EP0613938A1 (de
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Michael John Clarke
David Anthony Duncan
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Lubrizol Adibis Holdings UK Ltd
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BP Chemicals Additives 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
    • 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)
    • 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
    • C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular 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
    • C10L1/22—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)
    • C10L1/2387—Polyoxyalkyleneamines (poly)oxyalkylene amines and derivatives thereof (substituted by a macromolecular group containing 30C)
    • 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
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/18—Use of additives to fuels or fires for particular purposes use of detergents or dispersants for purposes not provided for in groups C10L10/02 - C10L10/16
    • 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
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
    • C10L1/1832—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom mono-hydroxy
    • 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
    • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/197—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid
    • C10L1/1973—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid mono-carboxylic
    • 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
    • C10L1/23—Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites
    • C10L1/231—Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites nitro compounds; nitrates; nitrites
    • 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
    • C10L1/30—Organic compounds compounds not mentioned before (complexes)
    • C10L1/305—Organic compounds compounds not mentioned before (complexes) organo-metallic compounds (containing a metal to carbon bond)
    • 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
    • C10L1/30—Organic compounds compounds not mentioned before (complexes)
    • C10L1/305—Organic compounds compounds not mentioned before (complexes) organo-metallic compounds (containing a metal to carbon bond)
    • C10L1/306—Organic compounds compounds not mentioned before (complexes) organo-metallic compounds (containing a metal to carbon bond) organo Pb compounds

Definitions

  • the present invention relates in general to internal combustion engine fuel compositions.
  • the invention relates to the use of nitrogen-containing compounds as dispersants in the aforesaid fuel compositions.
  • Nitrogen-containing compounds which have long been used as dispersant/detergent additives in lubricating oils include the hydrocarbyl-substituted succinimides.
  • the preparation of succinimides and their use as lubricating oil additives is described in, for example, US-A-3,024,237; US-A-3,202,678; US-A-3,219,666 and US-A-3,275,554.
  • Hydrocarbon fuels generally contain numerous deposit-forming substances. When used in internal combustion engines, deposits tend to form on and around constricted areas of the engine in contact with the fuel. In diesel engines, deposits tend to accumulate in the fuel injection system, thereby hampering good performance of the engine. In automobile engines deposits can build up on engine intake valves leading to progressive restriction of gaseous fuel mixture flow into the combustion chamber and also to valve sticking. It is common practice to incorporate a detergent in the fuel composition for the purpose of inhibiting the formation, and facilitating the removal, of engine deposits, thereby improving engine performance. Nitrogen-containing compounds commonly used as additives in hydrocarbon fuels include polyisobutene amines.
  • US-A-3,236,613 discloses petroleum distillate hydrocarbon fuels containing from between about 1 to about 100 pounds, per thousand barrels of fuel, of a compound of the following formula: wherein R is the aliphatic residue of an aliphatic dicarboxylic acid, R' is an aliphatic hydrocarbon group, R'' is a member from the group consisting of and x is an integer from 1 to 6.
  • Such compounds can be prepared by heating at 75 to 100oC for about 2 hours a mole to mole mixture of an aliphatic dicarboxylic acid anhydride and aliphatic primary amine to form the amic acid, ie subjecting the amic acid (A) to condensation reaction at 95oC to 150oC for 2 to 5 hours with a polyamine of the following formula: (R'') x NH 2 in substantially molar amounts to provide the following condensation reaction product: and further condensing product (B) in mole to mole ratio with salicyladehyde at 125 to 175oC for 2 to 5 hours.
  • the compounds function as anti-screen clogging and sediment stabilising addiion agents for petroleum hydrocarbon distillate fuel oils and, as antioxidants and metal deactivators in both fuel oils and gasolines.
  • Other publications, eg US-A-4,698,169 and EP-A-191967 disclose a reaction product useful as either a fuel or lubricant additive which is obtained by the reaction of an alkenyl succinic anhydride or acid with an aromatic secondary amine to form an intermediate product and thereafter reacting the intermediate product with either an alkanolamine, an aminomethane or a hindered alcohol.
  • hydrocarbyl-substituted succinic diamides obtainable as described hereinafter are particularly useful as dispersants in fuel compositions.
  • the present invention provides a hydrocarbon fuel composition
  • a hydrocarbon fuel composition comprising a hydrocarbon fuel and an amount sufficient to provide dispersancy of a hydrocarbyl-substituted succinic diamide, wherein the hydrocarbyl substituent is of a size sufficient to render the diamide soluble in the fuel, the diamide being obtainable by reacting at elevated temperature a secondary amine with either a hydrocarbyl-substituted succinic acid or an anhydride, ester or monoamide derivative thereof.
  • the hydrocarbyl substituent of the succinic diamide is of a size sufficient to render the diamide soluble in the hydrocarbon fuel. Typically this may be achieved with a hydrocarbyl substituent having at least 25 carbon atoms, preferably greater than 35 carbon atoms, and up to about 500 carbon atoms, preferably up to about 300 carbon atoms.
  • the hydrocarbyl substituent may be derived from a suitable polyalkene or mixture of polyalkenes selected from, for example, polyethylene, polypropylene and polybutenes.
  • a preferred hydrocarbyl substituent is derived from a polyisobutene.
  • Polyisobutene succinic anhydrides (PIBSAs) suitable for use in the reaction may be obtained commercially.
  • Polyisobutene succinic acids suitable for use in the reaction may be obtained by hydrolysis of PIBSAs, suitably using water as the hydrolysing agent, and at elevated temperature.
  • Polyisobutene succinic acid esters may suitably be obtained by esterification of either a PIBSA or a polyisobutene succinic acid.
  • Polyisobutene succinic monoamides may suitably be obtained by reacting a PIBSA or a polyisobutene succinic acid salt with up to 1 mole per mole of a secondary amine.
  • the secondary amine there may be used a secondary mono-, di- or poly-amine.
  • a secondary mono-amine having the formula:- wherein R 1 and R 2 are independently C 1 -C 15 hydrocarbyl groups, suitably alkyl groups, preferably C 1 to C 4 alkyl groups.
  • a secondary diamine having the formula:- wherein X is a divalent hydrocarbyl group, suitably an alkylene group, having up to 15 carbon atoms, preferably up to 6 carbon atoms; and R 1 and R 2 are independently C 1 to C 15 hydrocarbyl groups, suitably alkyl groups, preferably C 1 to C 4 alkyl groups.
  • a secondary polyamine having the formula:- wherein X is a C 1 to C 15 divalent hydrocarbyl group, suitably a C 1 to C 6 alkylene group, preferably an ethylene or propylene group, which may be substituted with, for example, hydroxyl groups; R 1 and R 2 are independently C 1 to C 15 hydrocarbyl groups, suitably alkyl groups, preferably C 1 to C 4 alkyl groups; and n is an integer in the range from 1 to 6, preferably from 1 to 4.
  • N-alkyl piperazines are preferred because they eliminate the possibility of the diamide product being contaminated with esters, unlike compounds of the formulae (IV) and (V).
  • a preferred secondary amine reactant is N-methyl piperazine.
  • the hydrocarbyl-sutstituted succinic diamide is obtainable by reacting at elevated temperature a hydrocarbyl-substituted succinic acid or an anhydride, ester or monoamide derivative thereof with a secondary amine. The reactants are reacted in proportions such that there is formed a diamide. Using a hydrocarbyl-substituted succinic acid or anhydride it is preferred to react at least 2 moles of the secondary amine for each mole of acid or anhydride. Using a hydrocarbyl-substituted succinic acid monoamide it is preferred to react at least 1 mole of the secondary amine for each mole of monoamide.
  • hydrocarbyl substituted succinic acid or anhydride it is preferred to react a hydrocarbyl substituted succinic acid or anhydride with at least 2 moles of the secondary amine for each mole of acid or anhydride.
  • a hydrocarbyl-substituted succinic acid monoamide as the starting material for the reaction with the secondary amine it is possible to produce diamides having different amido substituents by employing a secondary amine different to that used in the formation of the monoamide. Otherwise mixtures of diamides may be obtainable by using mixtures of at least two secondary amines in the diamide forming reaction.
  • the reaction may be accomplished in the presence or absence of a solvent.
  • Suitable solvents include liquid hydrocarbons, for example xylene or cyclohexane.
  • reaction of the acid or derivative thereof with the secondary amine may suitably be effected at elevated temperatures, suitably below 250°C, for example from about 90 to 180°C.
  • reaction of a PIBSA with diethanolamine for example, may suitably be represented as follows:-
  • reaction of a polyisobutene succinic acid with N-methyl piperazine may suitably be represented as follows:
  • the hydrocarbon fuel may suitably comprise a hydrocarbon fraction boiling in the gasoline range or a hydrocarbon fraction boiling in the diesel range.
  • Such gasolines may comprise mixtures of saturated, olefinic and aromatic hydrocarbons. They may be derived from straight-run gasoline, synthetically produced aromatic hydrocarbon mixtures, thermally or catalytically cracked hydrocarbon feedstocks, hydrocracked petroleum fractions or catalytically reformed hydrocarbons.
  • the octane number of the base fuel is not critical and will generally be above 65.
  • hydrocarbons may be replaced in part by alcohols, ethers, ketones or esters, typically in an amount up to 20% by weight.
  • liquid hydrocarbon fuel there may be used any fuel suitable for operating spark compression engines, such as those which may be found in road vehicles, ships and the like.
  • a diesel fuel will boil in the range from about 140°C to about 400°C (at atmospheric pressure), particularly in the range from about 150 to 390°C, especially from about 175 to 370°C.
  • Such fuels may be obtained directly from crude oil (straight-run) or from a catalytically or thermally cracked product or a hydrotreated product, or from a mixture of the aforesaid.
  • a biofuel for example rape seed methyl ester.
  • the cetane number will typically be in the range from 25 to 60.
  • the fuel composition contains the hydrocarbyl substituted succinic diamide in an amount sufficient to provide dispersancy. Typically in a gasoline fuel this amount will be in the range from 20 to 1000 ppm w/w based on the total weight of the composition. Typically in a diesel fuel this amount will be in the range from 10 to 500 ppm w/w based on the total weight of the composition.
  • the fuel composition may suitably be prepared by blending a concentrate composition comprising a fuel compatible hydrocarbon solvent and the hydrocarbyl-substituted succinic diamide with the hydrocarbon fuel.
  • the fuel composition in addition to the hydrocarbyl-substituted succinic diamide may contain known additives.
  • the nature of the additives will depend to some extent on the end-use of the fuel composition.
  • Diesel fuel compositions may contain nitrates or nitrites as a cetane improver, or copolymers of ethylene and/or vinylesters, eg vinylacetate, as a pour point depressant.
  • Gasoline fuel compositions may contain a lead compound as an anti-knock additive and/or an antioxidant, eg 2,6-di-tert-butyl phenol, and/or an anti-knock compound other than a lead compound, and/or an additional dispersant, for example a PIB polyamine.
  • the other additives (if any) may be blended directly into the fuel composition or may be incorporated by way of a concentrate composition.
  • PIBSA polyisobutene (PIB) of number average molecular weight (M n ) of about 1000)
  • M n number average molecular weight
  • n-heptane was subsequently removed on a rotary evaporator at 110oC/28 inches Hg over one hour.
  • N-methyl piperazine (NMP)(25 g), the "clean” PIBSA of Example A (200 g) and xylene (100 g) were mixed and the mixture heated to reflux at 165-170oC. The mixture was held at the reflux temperature for 3 hours. Water Evolution Up to 3 hours about 1.0 ml. End of reaction about 1.2 ml. Solvent Removal Charged 312.7 g. Product wt. 207.9 g.
  • Example 2 was repeated except that instead of using xylene (100 g) there was used cyclohexane (100 g). In this preparation vigorous reflux occurred initially. A temperature of 107oC was attained. After removal of 16.8 g cyclohexane a reflux temperature of 140oC was attained. Water Removal Time Elapsed Water Removed 65 minutes (107oC) 1.5 ml 345 minutes (end) 4.6 ml Solvent Strip Charge 271.3 g. Product wt 206.2 g.
  • a "clean" PIBSA derived from a commercially available more reactive, ie higher vinylidene content (about 60%) PIB of M n about 1300 was obtained by blending the PIBSA (715 g) and n-heptane (185 g) followed by filtering through a diatomaceous earth filter aid and removing the n-heptane solvent by rotary evaporation at 130oC/28 inches Hg (425 g blend charged; 400.1 g product recovered).
  • NMP N-methylpiperazine
  • 60 g (b.pt. 138oC) was added dropwise to a solution of commercially available PIBSA (75% solution derived from PIB of M n about 1000 in an aromatic solvent)(400 g) in xylene (100 g) at 90-120oC over 15 minutes.
  • An extra 100 g of xylene was added to stimulate reflux.
  • Water (10 g) was added to hydrolyse the PIBSA. The temperature was then increased to reflux. Solvent was removed at 28 inches Hg/150oC.
  • Analysis of Product Observed Total nitrogen 2.2% Basic nitrogen 1.2% Alkalinity value 45.9
  • Example 5 A mixture of a PIBSA identical to that used in Example 5 (400 g), xylene (230 g) and water (6.2 g) was charged to a one litre 5-necked flange pot reactor equipped with Eurotherm, agitator and Dean and Stark trap. The contents were then heated to 95oC to effect hydrolysis. Subsequently N-methyl piperazine (NMP) (64.8 g; b.pt. 138oC) was added.
  • NMP N-methyl piperazine
  • the product was stripped at 150oC/28.5 inches Hg to remove solvents. Analysis of product Total nitrogen 2.4%. Basic nitrogen 1.5%. Alkalinity value 59.5 mg KOH/g.
  • Results were generated in an Opel Kadett engine test run on fuel treated with either 500 or 1000 ppm w/w of an additive package.
  • the additive package was based on a commercial formulation modified in the respect that the customary dispersant actives component was replaced on a weight/weight basis in turn by a dispersant according to the invention and prior art succinimide dispersants as indicated in Table 2 below.
  • succinimides 1 and 2 These materials are characterised as follows:-

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Claims (10)

  1. Kraftstoffzusammensetzung, umfassend einen Kohlenwasserstoffkraftstoff und eine zur Bereitstellung von Dispergiervermögen ausreichende Menge eines Kohlenwasserstoff-substituierten Bernsteinsäurediamids, wobei der Kohlenwasserstoffsubstituent von ausreichender Größe ist, um das Diamid in dem Kraftstoff löslich zu machen, wobei das Diamid durch Umsetzen eines sekundären Amins mit entweder einer Kohlenwasserstoff-substituierten Bernsteinsäure oder einem Anhydrid, Ester oder Monoamidderivat davon bei hoher Temperatur erhältlich ist.
  2. Kohlenwasserstoff-Kraftstoffzusammensetzung nach Anspruch 1, wobei der Kohlenwasserstoffsubstituent 35 bis 300 Kohlenstoffatome aufweist.
  3. Kohlenwasserstoff-Kraftstoffzusammensetzung nach entweder Anspruch 1 oder Anspruch 2, wobei der Kohlenwasserstoffsubstituent von einem Polyisobuten abgeleitet ist.
  4. Kohlenwasserstoff-Kraftstoffzusammensetzung nach einem der vorangehenden Ansprüche, wobei das sekundäre Amin, das mit der Kohlenwasserstoff-substituierten Bernsteinsäure oder einem Derivat davon umgesetzt wird, ein Dialkanolamin der Formel: (HOR1)2NH    worin R1 eine C1- bis C6-Alkylengruppe darstellt, ist.
  5. Kohlenwasserstoff-Kraftstoffzusammensetzung nach einem der Ansprüche 1 bis 3, wobei das sekundäre Amin, das mit der Kohlenwasserstoff-substituierten Bernsteinsäure oder einem Derivat davon umgesetzt wird, die Formel: (HOR1 [NHR2]n)2NH    worin R1 und R2 unabhängig C1- bis C6-Alkylengruppen darstellen und n eine ganze Zahl im Bereich von 1 bis 6 ist, aufweist.
  6. Kohlenwasserstoff-Kraftstoffzusammensetzung nach einem der Ansprüche 1 bis 3, wobei das sekundäre Amin, das mit der Kohlenwasserstoff-substituierten Bernsteinsäure oder einem Derivat davon umgesetzt wird, ein N-Alkylpiperazin der Formel:
    Figure 00160001
       worin R2 eine C1- bis C10-Alkylgruppe darstellt, ist.
  7. Kohlenwasserstoff-Kraftstoffzusammensetzung nach Anspruch 6, wobei das N-Alkylpiperazin N-Methylpiperazin ist.
  8. Kohlenwasserstoff-Kraftstoffzusammensetzung nach einem der Ansprüche 1 bis 7, wobei die Kohlenwasserstoff-substituierte Bernsteinsäure oder das Derivat davon mit dem sekundären Amin bei einer Temperatur im Bereich von 90 bis 180°C umgesetzt wird.
  9. Kohlenwasserstoff-Kraftstoffzusammensetzung nach einem der vorangehenden Ansprüche, wobei der Kohlenwasserstoffkraftstoff eine Kohlenwasserstofffraktion, die im Benzinbereich siedet, umfaßt.
  10. Kohlenwasserstoff-Kraftstoffzusammensetzung nach einem der Ansprüche 1 bis 9, wobei der Kohlenwasserstoffkraftstoff eine Kohlenwasserstofffraktion, die im Dieselbereich siedet, umfaßt.
EP94301303A 1993-03-03 1994-02-24 Stickstoff enthaltende Dispergiermittel umfassende Kohlenwasserstoffkraftstoffszusammensetzungen Expired - Lifetime EP0613938B1 (de)

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GB9304350 1993-03-03
GB939304350A GB9304350D0 (en) 1993-03-03 1993-03-03 Fuel and lubricating oil compositions

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EP0613938A1 EP0613938A1 (de) 1994-09-07
EP0613938B1 true EP0613938B1 (de) 1998-07-22

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Cited By (2)

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US7807046B2 (en) 2003-12-19 2010-10-05 Shell Oil Company Systems, methods, and catalysts for producing a crude product
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DE69411784T2 (de) 1998-12-03
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GB9304350D0 (en) 1993-04-21
DE69411784D1 (de) 1998-08-27

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