EP0466511B1 - Motor fuels of enhanced properties - Google Patents

Motor fuels of enhanced properties Download PDF

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Publication number
EP0466511B1
EP0466511B1 EP91306359A EP91306359A EP0466511B1 EP 0466511 B1 EP0466511 B1 EP 0466511B1 EP 91306359 A EP91306359 A EP 91306359A EP 91306359 A EP91306359 A EP 91306359A EP 0466511 B1 EP0466511 B1 EP 0466511B1
Authority
EP
European Patent Office
Prior art keywords
fuel
gasoline
composition
volume
amines
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.)
Revoked
Application number
EP91306359A
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German (de)
English (en)
French (fr)
Other versions
EP0466511A1 (en
Inventor
John Vincent Hanlon
William Maynard Hager
Lawrence Joseph Cunningham
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.)
Afton Chemical Corp
Original Assignee
Afton Chemical Corp
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Application filed by Afton Chemical Corp filed Critical Afton Chemical Corp
Publication of EP0466511A1 publication Critical patent/EP0466511A1/en
Application granted granted Critical
Publication of EP0466511B1 publication Critical patent/EP0466511B1/en
Anticipated expiration legal-status Critical
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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
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/02—Use of additives to fuels or fires for particular purposes for reducing smoke development
    • 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
    • C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
    • C10L1/023—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for spark ignition
    • 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
    • C10L1/30—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
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    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/10—Use of additives to fuels or fires for particular purposes for improving the octane number
    • C—CHEMISTRY; METALLURGY
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    • C10L1/00—Liquid carbonaceous fuels
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    • C10L1/14—Organic compounds
    • C10L1/16—Hydrocarbons
    • C10L1/1608—Well defined compounds, e.g. hexane, benzene
    • C—CHEMISTRY; METALLURGY
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    • C10L1/00—Liquid carbonaceous fuels
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    • C10L1/18—Organic compounds containing oxygen
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
    • C10L1/1824—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms mono-hydroxy
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    • 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
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    • 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
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    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
    • C—CHEMISTRY; METALLURGY
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    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
    • C10L1/1855—Cyclic ethers, e.g. epoxides, lactides, lactones
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • C10L1/14—Organic compounds
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    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1857—Aldehydes; Ketones
    • 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
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    • C10L1/18—Organic compounds containing oxygen
    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid 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
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    • 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
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    • 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
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • 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
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    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
    • 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
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    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/223—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • C10L1/228—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles
    • C10L1/2283—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles containing one or more carbon to nitrogen double bonds, e.g. guanidine, hydrazone, semi-carbazone, azomethine
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    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
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    • C10L1/2387—Polyoxyalkyleneamines (poly)oxyalkylene amines and derivatives thereof (substituted by a macromolecular group containing 30C)

Definitions

  • This invention relates to unleaded gasoline fuel compositions having superior environmental and performance properties.
  • United States Patent No. 4139349 describes lead-free gasoline compositions comprising a synergistic combination of dicyclopentadienyl iron and cyclopentadienyl manganese tricarbonyl antiknocks.
  • the unleaded gasoline fuel composition of this invention has a Reid vapor pressure (ASTM test method D-323) of 8.5 psi (58.6 kPa) or less, preferably 8.0 psi (55.2 kPa) or less, and contains no more than 25% by volume aromatic hydrocarbon components and up to 1/32 gram of manganese per gallon (0.008g/liter) as at least one fuel-soluble cyclopentadienyl manganese tricarbonyl compound.
  • cyclopentadienyl manganese tricarbonyls increases the octane quality of the low Reid vapor pressure gasoline without increasing its volatility and without requiring an increase in its aromatics content, and it has been found that these manganese compounds tend to exert a greater octane-improving effect in paraffinic and naphthenic hydrocarbons than they do in aromatic gasoline hydrocarbons.
  • the use of the fuels of the invention results in reduced emission of carbon monoxide and nitrogen oxides (NO x ) during engine operation while having little effect on the level of tailpipe hydrocarbon emissions; and they exhibit virtually no adverse effect upon exhaust gas catalysts and oxygen sensors of the type commonly used in present day vehicles.
  • the fuels of the invention are "environmentally friendly".
  • the aforementioned cyclopentadienyl manganese tricarbonyl and low Reid vapor pressure fuel are blended in any suitable manner, e.g., by (a) blending the fuel-soluble additive into the gasoline during or after completion of the gasoline blending procedures or (b) mixing the additive with one or more streams of gasoline hydrocarbons or other blending components, such as oxygenated fuel blending components, before the streams are blended together.
  • the octane-enriched gasoline thus obtained may then be stored in at least one storage tank in a tank farm, if desired, before being distributed for use in fueling motor vehicles; and it may then be dispensed to motor vehicles.
  • Use of the present invention lessens the amount of volatile hydrocarbons released into the atmosphere during storage and/or during fueling of a motor vehicle; and, in comparison with corresponding fuels containing no cyclopentadienyl manganese tricarbonyl, the amount of carbon monoxide and nitrogen oxides released into the atmosphere during operation of motor vehicles is reduced.
  • the unleaded gasolines utilized in the practice of this invention must have a Reid vapor pressure of 8.5 psi (58.6 kPa) or below, and preferably 8.0 psi (55.2 kPa) or below.
  • Reid vapor pressures are determined at 100°F (37.8°C).
  • Such gasolines are lead-free in the sense that no organolead antiknock agent is blended into the fuel, although they may contain trace amounts of lead contaminants.
  • the hydrocarbonaceous gasoline base stocks that are used in forming the gasoline blends include straight run stocks, light naphtha fractions, cracked gasoline stocks obtained from thermal or catalytic cracking, hydrocracking, or similar methods, reformate obtained by catalytic reformation or like processes, polymer gasolines formed via polymerization of olefins, alkylates obtained by addition of olefins to isobutane or other hydrocarbons by alkylation processes, isomerates formed by isomerization of lower straight chain paraffins such as n-hexane, n-heptane, and the like, and other hydrocarbons of the gasoline boiling range formed by suitable refinery processing operations.
  • Suitable amounts of appropriate hydrocarbons formed by other methods such as production from coal or shale can be included, if desired.
  • reformates based on liquid fuels formed by the Fischer-Tropsch process can be included in the blends.
  • the resultant gasoline must satisfy the Reid vapor pressure requirements of this invention and additionally will possess the distillation characteristics typical of conventional regular, midgrade, premium, or super-premium unleaded gasolines.
  • the motor gasolines are generally within the parameters of ASTM D 4814 and typically have initial boiling points in the range of 70-115°F (21.1-46.1°C) and final boiling points in the range of 370-440°F (187.8-226.7°C) as measured by the standard ASTM distillation procedure (ASTM D 86).
  • the hydrocarbon composition of gasolines according to volume percentages of saturates, olefins, and aromatics is typically determined by ASTM test procedure D 1319.
  • the base gasoline will be a blend of stocks obtained from several refinery processes.
  • the final blend may also contain hydrocarbons made by other procedures such as alkylates made by the reaction of C4 olefins and butanes using an acid catalyst such as sulfuric acid or hydrofluoric acid, and aromatics made from a reformer.
  • the saturated gasoline components comprise paraffins and naphthenates. These saturates are generally obtained from: (1) virgin gasoline by distillation (straight run gasoline), (2) alkylation processes (alkylates), and (3) isomerization procedures (conversion of normal paraffins to branched chain paraffins of greater octane quality). Saturated gasoline components also occur in so-called natural gasolines. In addition to the foregoing, thermally cracked stocks, catalytically cracked stocks and catalytic reformates contain some quantities of saturated components.
  • Olefinic gasoline components are usually formed by use of such procedures as thermal cracking, and catalytic cracking. Dehydrogenation of paraffins to olefins can supplement the gaseous olefins occurring in the refinery to produce feed material for either polymerization or alkylation processes.
  • the gasoline gasoline base stock blends with which the cyclopentadienyl manganese tricarbonyl additive is blended pursuant to this invention will generally contain 40 to 80 volume % of saturates, 1 to 30 volume % olefins, and up to 25 volume % aromatics.
  • Gasoline base stock blends for use in the practice of this invention contain no more than 25% by volume of aromatics.
  • the overall fuel blend will contain no more than 1% by volume and most preferably no more than 0.8% by volume of benzene.
  • Particularly preferred unleaded gasolines produced and/or utilized in the practice of this invention not only meet the Reid vapor pressure criteria set forth hereinabove but in addition, are characterized by having (1) a maximum sulfur content of 300 ppm, (2) a maximum bromine number of 20, (3) a maximum aromatic content of 20% by volume, (4) a maximum content of benzene of 1% by volume, and (5) a minimum content of contained oxygen of 1% by weight in the form of at least one monoether or polyether, such gasoline having dissolved therein up to 1/32 gram of manganese per gallon (3.8 liters) as methylcyclopentadienyl manganese tricarbonyl.
  • Gasolines of this type not containing the manganese additive are sometimes referred to as reformulated gasolines. See for example Oil & Gas Journal , April 9, 1990, pages 43-48.
  • the preferred gasoline base stock blends are those having an octane rating of (R + M)/2 ranging from 78-95.
  • cyclopentadienyl manganese tricarbonyl compounds e.g., those of U.S. Pat. No. 2,818,417
  • these manganese compounds include the cyclopentadienyl, methylcyclopentadienyl, dimethylcyclopentadienyl, trimethylcyclopentadienyl, tetramethylcyclopentadienyl, pentamethylcyclopentadienyl, ethylcyclopentadienyl, diethylcyclopentadienyl, propylcyclopentadienyl, isopropylcyclopentadienyl, tert-butylcyclopentadienyl, octylcyclopentadienyl, dodecylcyclopentadienyl, ethylmethylcyclopentadienyl, and inden
  • the preferred compounds or mixtures of compounds are those which are in the liquid state of aggregation at ordinary ambient temperatures, such as methylcyclopentadienyl manganese tricarbonyl, ethylcyclopentadienyl manganese tricarbonyl, liquid mixtures of cyclopentadienyl manganese tricarbonyl and methylcyclopentadienyl manganese tricarbonyl, and mixtures of methylcyclopentadienyl manganese tricarbonyl and ethylcyclopentadienyl manganese tricarbonyl.
  • the most preferred compound because of its commercial availability and its excellent combination of properties and effectiveness is methylcyclopentadienyl manganese tricarbonyl.
  • An unleaded motor gasoline blend is produced containing 58.9% saturated hydrocarbons, 17.5% olefinic hydrocarbons and 23.6% aromatic hydrocarbons, all of the gasoline boiling range.
  • the Reid vapor pressure of the blend is 8.5 psi (58.6 kPa).
  • This base fuel are blended methylcyclopentadienyl manganese tricarbonyl to a concentration of 1/32 gram of manganese per gallon (0.008 g/liter) and 4-methyl-2,6-di-tert-butylphenol to a concentration of 7.5 pounds per thousand barrels (21.4 g/m3).
  • the product After storing the motor gasoline over water in a field storage tank on a tank farm, the product is transported by tank trucks to gasoline filling stations where it is dispensed on demand to motor vehicles. The vehicles consume the same during their operation.
  • An unleaded motor gasoline of this invention is produced to contain 56.9 saturates, 20.0% olefins and 23.1% aromatics, all of the gasoline boiling range.
  • the components are selected such that the Reid vapor pressure of the blend is 8.4 psi (57.9 kPa).
  • a mixture of tertiary butylated phenolic antioxidants containing 85% by weight of 2,6-di-tert-butylphenol is blended into the fuel to a concentration of 6.5 pounds per thousand barrels (18.5 g/m3).
  • Methylcyclopentadienyl manganese tricarbonyl is blended into the resultant blend to a concentration of 1/32 gram of manganese per gallon (0.008 g/liter).
  • This fuel is stored, transported, and dispensed to and utilized in the operation of motor vehicles, the majority of which contain catalytic converters.
  • methylcyclopentadienyl manganese tricarbonyl and methyl tert-butyl ether in amounts such that the resultant fuel contains 1/32 gram of manganese per gallon (0.008 g/liter) and 2.7% by weight of oxygen as methyl tert-butyl ether.
  • the finished fuel which can contain, and preferably does contain, conventional amounts of antioxidant, metal deactivator, and carburetor detergent, is dispensed to and utilized in the operation of motor vehicles including passenger cars, buses, trucks, vans, and motorcycles.
  • Examples 1-3 are repeated except that in one case the respective motor fuels contain 1/40 gram of manganese per gallon (0.007 g/liter), in another the respective motor fuels contain 1/50 gram of manganese per gallon (0.005 g/liter), in a third case, 1/64 gram of manganese per gallon (0.004 g/liter) and in still another case, 1/100 gram of manganese per gallon (0.003 g/liter).
  • Examples 1-4 are repeated except that in each case the methylcyclopentadienyl manganese tricarbonyl is replaced by an equal concentration of manganese as cyclopentadienyl manganese tricarbonyl.
  • Examples 1-4 are repeated except that in one series of cases the respective fuels contain instead of methylcyclopentadienyl manganese tricarbonyl, a mixture of 90% by weight of methylcyclopentadienyl manganese tricarbonyl and 10% by weight of cyclopentadienyl manganese tricarbonyl in amounts such that the respective fuels contain the same respective concentrations of manganese as the fuels of Examples 1-4.
  • the respective fuels of Examples 1-4 contain the same respective concentrations of manganese in the form of dimethylcyclopentadienyl manganese tricarbonyl in lieu of the methylcyclopentadienyl manganese tricarbonyl.
  • the specified concentrations of manganese in the fuels of Examples 1-4 are supplied by tert-butylcyclopentadienyl manganese tricarbonyl.
  • the manganese additive used in forming the motor fuel compositions is indenylmanganese tricarbonyl instead of methylcyclopentadienyl manganese tricarbonyl.
  • An unleaded motor gasoline blend having a Reid vapor pressure of 7.8 psi (53.8 kPa) is formulated from 72.5% saturates, 4.0% olefins, and 23.5% aromatics (of which less than 3% by volume is benzene so that the fuel contains less than 1% by volume of benzene).
  • Methyl tert-butyl ether is blended into the base gasoline in amount sufficient to provide an oxygen content of 2.0% by weight in the fuel.
  • methylcyclopentadienyl manganese tricarbonyl is blended into the resultant motor fuel in an amount equivalent to 1/35 gram of manganese per gallon (0.008 g/liter).
  • Example 7 is repeated with the exceptions that (a) the initial gasoline blend has a Reid vapor pressure of 7.9 psi (54.5 kPa) and is composed of 75.7% saturates, 4.8% olefins, and 19.5% aromatics (of which aromatics, less than 3.5% by volume is benzene); and (b) a mixture of methyl tert-butyl ether and ethyl tert-butyl ether is blended into the fuel in an amount such that the content of the oxygenated fuel blend is equivalent to 2.5% by weight of oxygen.
  • the initial gasoline blend has a Reid vapor pressure of 7.9 psi (54.5 kPa) and is composed of 75.7% saturates, 4.8% olefins, and 19.5% aromatics (of which aromatics, less than 3.5% by volume is benzene); and (b) a mixture of methyl tert-butyl ether and ethyl tert-butyl ether is blended into the fuel in
  • Example 7 is again repeated except that (a) the initial gasoline blend has a Reid vapor pressure of 7.7 psi (53.1 kPa) and is composed of 78.6% saturates, 4.4% olefins and 17.0% aromatics (the entire fuel blend again containing less than 1% by volume of benzene); and (b) in lieu of methyl tert-butyl ether, tert-amyl methyl ether is blended into the gasoline in an amount equivalent to an oxygen content in the fuel of 2.7% by weight.
  • the initial gasoline blend has a Reid vapor pressure of 7.7 psi (53.1 kPa) and is composed of 78.6% saturates, 4.4% olefins and 17.0% aromatics (the entire fuel blend again containing less than 1% by volume of benzene); and (b) in lieu of methyl tert-butyl ether, tert-amyl methyl ether is blended into the gasoline in an amount equivalent to an oxygen content in the fuel of 2.
  • Blended with the respective fuels of Examples 7-9 at a concentration level of 100 pounds per thousand barrels, (285.3 g/m3) is a polyether amine deposit control additive available commercially from Oronite Chemical Co. as OGA-480.
  • Blended with the respective fuels of Examples 7-9 at a concentration of 100 pounds per thousand barrels (285.3 g/m3) is a polyalkenyl succinimide deposit control additive available commercially from Ethyl Petroleum Additives, Ltd. as HITEC 4450 additive.
  • Blended with the respective fuels of Example 7-9 at a concentration level of 100 pounds per thousand barrels (285.3 g/m3) is a polyisobutenyl amine deposit control additive available commercially from Oronite Chemical Co. as OGA-472.
  • the fuels of this invention can, and preferably do, contain additives in addition to the cyclopentadienyl manganese tricarbonyl compound or compounds.
  • additives include antioxidants, deposit-control additives (also known as induction system cleanliness additives or fuel detergents), and oxygenated materials such as dialkyl ethers, all with the proviso that the volatility of such materials does not cause the fuel to exceed the Reid vapor pressure limitations required pursuant to this invention.
  • additives that may be employed include supplemental antiknock additives such as aromatic amine antiknocks such as N-methyl aniline; iron antiknock compounds such as ferrocene, methylferrocene, and butadiene iron tricarbonyl; and nickel antiknock compounds such as cyclopentadienyl nickel nitrosyl.
  • supplemental antiknock additives such as aromatic amine antiknocks such as N-methyl aniline
  • iron antiknock compounds such as ferrocene, methylferrocene, and butadiene iron tricarbonyl
  • nickel antiknock compounds such as cyclopentadienyl nickel nitrosyl.
  • Corrosion inhibitors, metal deactivators, demulsifiers, and dyes comprise other types of additives that can be employed.
  • Preferred oxygenated materials that can be, and preferably are, blended into the fuels of this invention are ethers of suitable low volatility such as methyl tert-butyl ether, ethyl tert-butyl ether, tert-amyl methyl ether, and 2,2-diethyl-1,3-propanediol. Also useful are fuel-soluble esters and alcohols of suitably low volatility such as tert-butyl acetate, 1-hexanol, 2-hexanol, 3-hexanol, and polyethoxyethanols. Usually such oxygenated compounds are employed in amounts sufficient to provide up to 3 to 4 weight % oxygen in the fuel, provided such usage is consistent with existing or proposed legislation.
  • oxygen-containing blending agents include p-cresol, 2,4-xylene, 3-methoxyphenol, 2-methylfuran, cyclopentanone, isovaleraldehyde, 2,4-pentanedione and similar oxygen-containing substances.
  • Preferred antioxidants for the fuels of this invention are hindered phenolic antioxidants, such as 2,6-di-tert-butyl-phenol, 2,4-dimethyl-6-tert-butylphenol, 4-methyl-2,6-di-tert-butylphenol, 4-ethyl-2,6-di-tert-butylphenol, 4-butyl-2,6-di-tert-butylphenol, and mixtures of tertiary butylated phenols predominating in 2,6-di-tert-butylphenol.
  • aromatic amine antioxidants can prove useful either alone or in combination with a phenolic antioxidant.
  • Antioxidants are usually employed in amounts of up to 25 pounds per thousand barrels (71.3 g/m3), the amount used in any given case being dependent upon the stability (e.g., olefin content) of the gasoline.
  • additives preferably utilized in the fuels of this invention are ashless detergents such as polyether amines, polyalkenyl amines, alkenylsuccinimides, polyether amide amines, and the like.
  • ashless detergents such as polyether amines, polyalkenyl amines, alkenylsuccinimides, polyether amide amines, and the like.
  • Such materials can be used at treat levels of 50 to 500 pounds per thousand barrels (142.6-1426.4 g/m3), and more usually in the range of 100 to 200 pounds per thousand barrels (285.3-570.6 g/m3).
  • cyclopentadienyl manganese tricarbonyl compounds as well as the other supplemental additives or blending agents can be blended with the base fuels according to well known procedures utilizing conventional mixing equipment. This invention is directed to all such fuel compositions meeting the primary requisites of this invention.

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EP91306359A 1990-07-13 1991-07-12 Motor fuels of enhanced properties Revoked EP0466511B1 (en)

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CA2076302C (en) * 1991-08-23 2003-05-27 Thomas Albert Leeper Gasoline engine fuels of enhanced properties
US6187064B1 (en) 1991-10-28 2001-02-13 Ethyl Petroleum Additives, Inc. Unleaded aviation gasoline
CA2080193C (en) * 1991-10-28 2003-12-16 Douglas Harold Henderson Unleaded aviation gasoline
US5551957A (en) * 1992-05-06 1996-09-03 Ethyl Corporation Compostions for control of induction system deposits
KR100307417B1 (ko) * 1992-08-24 2001-11-30 윌리암씨.오 연료의경제성을증가시키는방법및이를위한연료조성물
US5511517A (en) * 1994-02-10 1996-04-30 Ethyl Corporation Reducing exhaust emissions from otto-cycle engines
EP0748364B1 (en) * 1994-03-02 2007-11-21 ORR, William C. Unleaded fuel compositions
AU1553402A (en) * 1994-03-02 2002-03-28 William C. Orr Advanced vapour phase combustion
CA2194572A1 (en) * 1994-05-31 1995-12-07 William C. Orr Vapor phase combustion methods and compositions
JPH11504974A (ja) * 1995-06-07 1999-05-11 オア，ウィリアム，シー． 蒸気相燃焼法および組成物ｉｉ
GB9827592D0 (en) * 1998-12-15 1999-02-10 Hamelin Holdings Limited Fuel composition
AU6360900A (en) * 1999-07-21 2001-02-13 Exxon Chemical Patents Inc. Hydrocarbon fuel composition containing an ester
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WO2002055636A1 (en) * 2001-01-12 2002-07-18 Exxonmobil Research And Engineering Company Gasoline composition
WO2005087901A2 (en) * 2004-03-09 2005-09-22 Innospec Limited Fuel additive composition having antiknock properties
JP5542840B2 (ja) * 2008-12-29 2014-07-09 シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー 燃料組成物
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AU8016791A (en) 1992-01-16
DE69106611D1 (de) 1995-02-23
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DE69106611T2 (de) 1995-05-18

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