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
  • C10L1/22—Organic compounds containing nitrogen
• • 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
• • 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

• This invention relates to an improved motor fuel composition for an internal combustion engine. More particularly, the invention relates to a motor fuel composition effective to inhibit the formation of harmful deposits, for example, on the carburetor of an internal combustion engine.
• Gasoline fuels containing oxygenates have recently become more prevalent and these gasoline fuels can require new compositions as carburetor detergents to obtain optimum results.
• the present invention is aimed at providing compositions especially useful as carburetor detergents for gasoline fuels containing oxygenates and especially to provide gasoline fuel compositions containing oxygenates with a decreased tendency to form deposits in carburetors.
• this invention provides a detergent composition comprising two essential components wherein:
• carboxylic dispersant means known hydrocarbon-soluble dispersants whose molecular structure is highlighted by the presence of a substantially saturated hydrocarbon-based radical containing at least about 30 aliphatic carbon atoms and at least 1 acyl or acyloxy attached to said hydrocarbon-based radical and also through nitrogen to a polar group.
• the carboxylic dispersants are the reaction products of carboxylic acids or derivatives thereof with polar reagents, including organic nitrogen-containing compounds having at least one >NH group such as polyamines.
• Component A employed in the compositions of this invention are known amides having the formula:
• these amides are formed by reacting fatty acids having the formula:
• Component B employed in the compositions of this invention is a hydrocarbon-soluble "carboxyl. " dispersant”.
• carboxylic dispersant means known hydrocarbon-soluble dispersants whose molecular structure is characterized by the presence of a substantially saturated hydrocarbon-based radical containing at least about 30 aliphatic carbon atoms and at least 1 acyl or acyloxy attached to said hydrocarbon-based radical and also through nitrogen to a polar group.
• the carboxylic dispersants are the reaction products of carboxylic acids or derivatives thereof with polar reagents, including organic nitrogen-containing compounds having at least one >N H group such as polyamines.
• the preferred carboxylic dispersants for use as Component B are those in which the acidic moiety is a substituted succinic acid. Dispersants of this type are most often prepared by the reaction of one of the above-identified polar reagents with the appropriate substituted succinic acylating agent.
• suitable acylating agents include the acids, anhydrides, esters and acyl hadlides, with the acids and anhydrides being preferred.
• the substituted succinic acylating agent may be prepared by the alkylation of maleic acid, fumaric acid, maleic anhydride or the like with a source of the desired hydrocarbon-based radical, which is a known reaction described in the patents incorporated by reference hereinabove.
• hydrocarbon-based radical denotes a radical having a carbon atom directly attached to the remainder of the molecule and having predominantly hydrocarbon character within the context of this invention. Such radicals include the following:
• the hydrocarbon-based radicals in Component B are free from acetylenic unsaturation and have about 30 to about 5000 carbon atoms, desirably about 5C to about 300 carbon atoms.
• the radicals are usually hydrocarbon or chloro-substituted hydrocarbon.
• the source of the hydrocarbon-based radical is generally a homopolymer or interpolymer of polymerizable olefin monomers containing about two to sixteen and usually about two to six carbon atoms.
• Illustrative monomers of this type are ethylene, propylene, 1-butene, 2-butene, isobutene, I-octene and 1-decene.
• the polymer may also contain units derived from polyenes, including conjugated dienes such as 1,3-butadiene and isoprene; nonconjugated dienes such as 1,4-hexadiene, 1,4-cyclohexadiene, 5-ethylidene-2-norbornene and 1,6-octadiene; and trienes such as 1-isopropylidene-3a,4,7,7a-tetrahydroindene, 1-isopropylidenecyclopentadiene and 2-(2-methylene-4-methyl-3-pentenyl)[2.2.1]bicyclo-5-heptene.
• conjugated dienes such as 1,3-butadiene and isoprene
• nonconjugated dienes such as 1,4-hexadiene, 1,4-cyclohexadiene, 5-ethylidene-2-norbornene and 1,6-octadiene
• trienes such as 1-iso
• a first preferred class of polymers comprises those of terminal olefins such as propylene, 1-butene, isobutene and 1-hexene. Especially preferred within this class are polybutenes comprising predominantly isobutene units.
• a second preferred class comprises terpolymers of ethylene, a C 3-8 a-monoolefin and a polyene selected from the group consisting of nonconjugated dienes (which are especially preferred) and trienes. Illustrative of these terpolymers is "Ortholeum 2052" manufactured by E. I.
• duPont de Nemours & Company which is a olymer containing about 48 mole percent ethylene groups, 48 mole percent propylene groups, and 4 mole percent 1,4-hexadiene groups, and having an inherent viscosity of 1.35 (8.2 grams of polymer in 100 ml. of carbon tetrachloride at 30°C.).
• the source of the hydrocarbon-based radical contains at least about 30 and preferably at least about 50 carbon atoms.
• the olefin polymers those having a number average molecular weight (as determined by gel permeation chromatography) of about 700-5000 are preferred, although higher polymers having number average molecular weights from about 10,000 to about 100,000 or higher may sometimes be used.
• At least one mole of unsaturated acid or acid derivative is normally used per mole of hydrocarbon-based radical source. Particularly when said source contains a substantial number of olefinic bonds, more than one mole of unsaturated acid or acid derivative may be used per mole thereof.
• the hydrocarbon-based radical in the resulting acylating agent should be substantially saturated; that is, at least about 95% of the carbon-carbon bonds therein should be single bonds.
• the carboxylic dispersant is prepared by reacting the substituted succinic acid, anhydride or other acrylating agent with at least one of the above-identified polar reagents.
• Suitable nitrogen compounds are those characterized by a radical of the structure >NH wherein the two remaining valences of nitrogen are satisfied by hydrogen, in particular, polyamines.
• the polyamines for preparing Component B are alkylene polyamines (and mixtures thereof), including those having the formula: wherein n is an integer between about 1 and 10, preferably between 2 and 8; each A is independently hydrogen or a hydrocarbon or hydroxy-substituted hydrocarbon radical having up to about 30 atoms; and R 2 is a divalent hydrocarbon radical having about 1-18 carbons.
• A is an aliphatic radical of up to about 10 carbon atoms which may be substituted with one or two hydroxy groups, and R i is a lower alkylene radical having 1-10, preferably 2-6, carbon atoms.
• the alkylene polyamines where each A is hydrogen.
• alkylene polyamines include methylene polyamines, ethylene polyamines, butylene polyamines, propylene polyamines, pentylene polyamines, hexylene polyamines and heptylene polyamines. The higher homologs of such amines and related aminoalkyl-substituted piperazines are also included. Specific examples of such polyamines include ethylene diamine, triethylene tetramine, tris(2-aminoethyl)amine, propylene diamine, trimethylene diamine, hexamethylene diamine, decamethylene diamine, octamethylene.
• ethylene polyamines examples of which are mentioned above, are especially useful for reasons of cost and effectiveness.
• Such polyamines are described in detail under the heading "Diamines and Higher Amines, Aliphatic” in Kirk-Othmer, Encyclopedia- of Chemical Technology, Third Edition, Vol. 7, pp. 580-602. They are prepared most conveniently by the reaction of an alkylene chloride with ammonia or by reaction of an ethylene imine with a ring-opening reagent such as ammonia. These reactions result in the production of the somewhat complex mixtures of alkylene polyamines, including cyclic condensation products such as piperazines. Because of their availability, these mixtures are particularly useful in preparing the compositions of this invention. Satisfactory products can also be obtained by the use of pure alkylene polyamines.
• Hydroxy polyamines e.g., alkylene polyamines having one or more hydroxyalkyl substituents on the nitrogen atoms, are also useful in preparing Component B.
• Preferred hydroxyalkyl-substituted alkylene polyamines are those in which the hydroxyalkyl group has less than about 10 carbon atoms.
• hydroxyalkyl-substituted polyamines include N-(2-hydroxyethyl)ethylene, diamine, N,N'-bis(2-hydroxyethyl)ethylene diamine, 1-(2-hydroxyethyl)-piperazine, monohydroxypropyldiethylene trimine, dihydroxy-propyltetraethylene pentamine and N-(3-hydroxybutyl)tetramethylene diamine.
• Higher homologs obtained by condensation of the above-illustrated hydroxyalkyl-substituted alkylene amines through amino radicals or through hydroxy radicals are likewise useful.
• a substantially inert, normally liquid organic diluent such as benzene, toluene, xylene or naphtha.
• Typical carboxylic dispersants suitable for use as Component B are listed in Table I by reactants and diluent.
• the detergent compositions of this invention generally contain equal parts by weight of Component A and Component B. Most often, the weight ratio of Component A to Component B is between about 0.2:1 and.about 5:1, and preferably between about 1: 1 and about 3:1.
• compositions of this invention are principally useful as carburetor detergent additives for gasoline fuel compositions, especially gasoline fuel compositions containing from about 1 volume percent to about 15 volume percent, preferably from about 2 volume percent to about 10 volume percent, oxygenate additives such as alcohols, ethers, and the like, e.g., methanol, ethanol, tertiary butyl alcohol, diethyl ether, methyl ethyl ether, and mixtures thereof.
• oxygenate additives such as alcohols, ethers, and the like, e.g., methanol, ethanol, tertiary butyl alcohol, diethyl ether, methyl ethyl ether, and mixtures thereof.
• these fuel compositions contain an amount of the composition of this invention sufficient to provide carburetor and engine detergency; usually, this amount is about 10-1000 parts by weight, preferably about 25-250 parts, of the composition of this invention per million parts of fuel.
• the fuel compositions can contain, in addition to the compositions of this invention, other additives which are well known to those of skill in the art.
• additives such as tetraethyl lead, dyes, antioxidants such as 2,6-di-tertiary-butyl-4-methylphenol, rust inhibitors such as alkylated succinic acids and anhydrides, bacteriostatic agents, gum inhibitors, metal deactivators, demulsifiers, upper cylinder lubricants and anti-icing agents.
• compositions of this invention can be added directly to the fuel, or they can be diluted with a substantially inert, normally liquid organic diluent such as naphtha, benzene, toluene, xylene or a normally liquid fuel as described above, to form an additive concentrate.
• a substantially inert, normally liquid organic diluent such as naphtha, benzene, toluene, xylene or a normally liquid fuel as described above
• These concentrates generally contain about 20-90% by weight of the composition of this invention and may contain, in addition, one or more other conventional additives known in the art or described hereinabove.
• Example I An. illustrative detergent composition of this invention is present in Example I below.
• An example of the detergent compositions of this invention is a mixture of equal parts by weight of Component A and Component B.
• An example of a gasoline composition of this invention is unleaded base gasoline containing 5 volume percent methanol, 5 volume percent tertiary butyl alcohol, and 250 ppm of the detergent composition of Example I.
• compositions which contain only Component A or Component B can provide improved inhibition to deposit formation as opposed to compositions which contain only Component A or Component B.

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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)
• Detergent Compositions (AREA)
• Liquid Carbonaceous Fuels (AREA)

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Cited By (9)

Citations (2)

• 1985
  • 1985-01-14 EP EP85100316A patent/EP0149486A3/de not_active Withdrawn

Patent Citations (2)

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