EP2582777B1 - Composition de carburant et son utilisation - Google Patents

Composition de carburant et son utilisation Download PDF

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Publication number
EP2582777B1
EP2582777B1 EP11729238.3A EP11729238A EP2582777B1 EP 2582777 B1 EP2582777 B1 EP 2582777B1 EP 11729238 A EP11729238 A EP 11729238A EP 2582777 B1 EP2582777 B1 EP 2582777B1
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EP
European Patent Office
Prior art keywords
fuel
gasoline
weight
composition
engine
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Active
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EP11729238.3A
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German (de)
English (en)
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EP2582777A1 (fr
Inventor
Roger Francis Cracknell
Yajnanarayana Jois
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Shell Internationale Research Maatschappij BV
Shell USA Inc
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Shell Internationale Research Maatschappij BV
Shell Oil Co
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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
    • C10L1/16—Hydrocarbons
    • C10L1/1608—Well defined compounds, e.g. hexane, benzene
    • 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
    • C10L1/04—Liquid carbonaceous fuels essentially based on blends of hydrocarbons
    • C10L1/06—Liquid carbonaceous fuels essentially based on blends of hydrocarbons 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
    • C10L1/04—Liquid carbonaceous fuels essentially based on blends of hydrocarbons
    • C10L1/08—Liquid carbonaceous fuels essentially based on blends of hydrocarbons for compression 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
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • 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
    • 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

Definitions

  • the present invention relates to a gasoline composition and its use, particularly, in combustion engines.
  • Spark initiated internal combustion gasoline engines require fuel of a minimum octane level which depends upon the design of the engine. Petroleum refineries are constantly faced with the challenge of continually improving their products to meet increasingly severe governmental efficiency and emission requirements, and consumers' desires for enhanced performance. For example, in producing a fuel suitable for use in an internal combustion engine, petroleum producers blend a plurality of hydrocarbon containing streams to produce a product that will meet governmental combustion emission regulations and the engine manufacturers performance fuel criteria, such as research octane number (RON). Similarly, engine manufacturers conventionally design spark ignition type internal combustion engines around the properties of the fuel. For example, engine manufacturers endeavor to inhibit to the maximum extent possible the phenomenon of auto-ignition which typically results in knocking and, potentially engine damage, when a fuel with insufficient knock-resistance is combusted in the engine.
  • US 7517215 B1 describes a method for distributed ignition wherein a combustion fuel and an ignition mixture are combined.
  • the ignition mixture comprises ignition agents and fuel and where ignition agents can be nano-metallic particles in combination with single-walled carbon nano-tubes (SWCNTs).
  • US 5354344 A describes a fuel oil composition for use in a spark ignition engine, which comprises conventional gasoline for spark ignition engine use and a compound selected from the group consisting of an alkynyl alcohol, alkynyl ether, alkynyl ketone, alkenyl aldehyde or an acetal thereof, furan or a furan compound, and an alkenyl ether.
  • WO 2008/071628 A1 describes a method of increasing the sensitivity (RON - MON) of a gasoline composition comprising admixing with a gasoline base fuel from 1 to 20 vol.%, based on total volume of the gasoline composition, of a nitroalkane selected from the group consisting of nitroethane, nitropropane and mixtures thereof; and use of such a gasoline composition for improved operation of a homogeneous charge compression ignition (HCCI) engine over a range of load conditions.
  • HCCI homogeneous charge compression ignition
  • the present invention provides a gasoline composition
  • a gasoline composition comprising (a) a major amount of a mixture of hydrocarbons in the gasoline boiling range and (b) a minor amount of cyclopropyl acetylene, wherein the term 'minor amount' means less than 50% by weight of the total fuel composition.
  • the present invention provides a method of (i) improving the flame speed of a gasoline and/or (ii) increasing sensitivity of a gasoline, which method comprises adding to a major portion of a gasoline mixture minor amounts of cyclopropyl acetylene, wherein the term 'minor amount' means less than 50% by weight of the total fuel composition.
  • flame speed is the measured rate of expansion of the flame front, generally measured in meters/second (m/s).
  • flame speed depends on gas pressure, temperature, and density change as a result of changes in volume due to piston motion (see Internal Combustion Engine Fundamentals, John B. Heywood. McGraw-Hill Book Co., 1988 ).
  • rate of expansion of the flame front can also be measured by the increase in the pressure.
  • Early pressure rise after spark (at 0 seconds) is also a measure of high burning velocity.
  • the gasoline composition of the present invention contains component (b) of a minor amount of cyclopropyl acetylene, wherein the term 'minor amount' means less than 50% by weight of the total fuel composition.
  • Cyclopropyl acetylene includes an acetylenic group and the term "acetylenic group” refers to unsaturated hydrocarbons that have carbon atoms in chains linked by one or more triple bonds.
  • the component (b) is a compound having the formula: wherein n is 0 and R 1 to R 6 are independently hydrogen.
  • n could be an integer from 0 to 7;
  • R 1 to R 6 could independently be hydrogen, alkyl group having 1 to 7 carbon atoms, alkenyl group having 1 to 7 carbon atoms, alkynyl group having 1 to 7 carbon atoms, cyclic group having 1 to 7 carbon atoms, with the proviso that the total number of carbon atoms in the compound are from 5 to 12.
  • cyclopropylacetylene can be prepared by chlorination of acetylcyclopropane with PCl 5 in the presence of an organic base in a chlorinated hydrocarbon with dehydrochlorination of the mixture of alpha,-alpha dichlorocyclopropane and alpha-chlorovinylcyclopropane (with base at reflux in a solvent) and simultaneous distillation.
  • Cycopropyl Cyanide can be prepared by the reaction of sodium amide with chlorobutyronitrile ( Organic Syntheses, Volume 3, page 223. John Wiley & Sons, Inc. Submitted by M. J. Schlatter and checked by R. L.shriner and Chris B est). Other methods can be used to prepare the cyclopropyl group-containing acetylenic compounds useful in the invention as are known to one who is skilled in the art of organic synthesis.
  • cyclopropyl group-containing acetylenic compounds include, for example, cyclopropyl acetylene; 1-cyclopropyl-1-propyne; 1-cyclopropyl-2-propyne; 1-methyl-1-ethynyl-cyclopropane; 2-methyl-1-ethynyl-cyclopropane; 1,1-(3-methylene-1-propyne-1,3-diyl)bis-; 1,1-bicyclopropyl, 2,2-diethynyl-; 1-cyclopropylpenta-1,3-diyne; cyclopropane, 1,1-(1,3-butadiyne-1,4-diyl)bis-; cyclopropane, 1,1-(3-methyl-1-propyne-1,3-diyl)bis-; and 1,4-dicyclopropylbuta-1,3-diyne.
  • the fuel composition of the present invention comprises a major amount of a mixture of hydrocarbons in the gasoline boiling range and a minor amount of component (b).
  • component (b) means less than 50% by weight of the total fuel composition, preferably less than about 30% by weight of the total fuel composition. However, the term “minor amount” will contain at least some amount, preferably at least 0.001% by weight of the total fuel composition.
  • component (b) is introduced into the combustion zone of the engine in a variety of ways to improve flame speed.
  • a preferred method is to add a minor amount of component (b) to the fuel.
  • component (b) may be added directly to the fuel or blended with one or more carriers to form an additive concentrate which may then be added at a later date to the fuel.
  • component (b) used will depend on the particular variation of Formula I used, the engine, the fuel, and the presence or absence of carriers and additional detergents. Generally, component (b) is added in an amount up to about 20% by weight, especially from about 0.005% by weight, more preferably from about 0.05% by weight, even more preferably from about 0.5% by weight, most preferably from about 1% by weight, based on the total weight of the fuel composition.
  • Suitable liquid hydrocarbon fuels of the gasoline boiling range are mixtures of hydrocarbons having a boiling range of from about 25°C to about 232°C and comprise mixtures of saturated hydrocarbons, olefinic hydrocarbons and aromatic hydrocarbons.
  • Preferred are gasoline mixtures having a saturated hydrocarbon content ranging from about 40% to about 80% by volume, an olefinic hydrocarbon content from 0% to about 30% by volume and an aromatic hydrocarbon content from about 10% to about 60% by volume.
  • the base fuel is derived from straight run gasoline, polymer gasoline, natural gasoline, dimer and trimerized olefins, synthetically produced aromatic hydrocarbon mixtures, or from catalytically cracked or thermally cracked petroleum stocks, and mixtures of these.
  • the hydrocarbon composition and octane level of the base fuel are not critical.
  • the octane level, (R+M)/2, will generally be above about 85.
  • Any conventional motor fuel base can be employed in the practice of the present invention.
  • hydrocarbons in the gasoline can be replaced by up to a substantial amount of conventional alcohols or ethers, conventionally known for use in fuels.
  • the base fuels are desirably substantially free of water since water could impede a smooth combustion.
  • the word major amount is used herein because the amount of hydrocarbons in the gasoline boiling range is often 50 weight or volume percent or more.
  • the hydrocarbon fuel mixtures to which the invention is applied are substantially lead-free, but may contain minor amounts of blending agents such as methanol, ethanol, ethyl tertiary butyl ether, methyl tertiary butyl ether,tert-amyl methyl ether and the like, at from about 0.1% by volume to about 15% by volume of the base fuel, although larger amounts may be utilized.
  • blending agents such as methanol, ethanol, ethyl tertiary butyl ether, methyl tertiary butyl ether,tert-amyl methyl ether and the like, at from about 0.1% by volume to about 15% by volume of the base fuel, although larger amounts may be utilized.
  • the fuels can also contain conventional additives including antioxidants such as phenolics, e.g., 2,6-di-tertbutylphenol or phenylenediamines, e.g., N,N'-di-sec-butyl-p-phenylenediamine, dyes, metal deactivators, dehazers such as polyester-type ethoxylated alkylphenol-formaldehyde resins.
  • antioxidants such as phenolics, e.g., 2,6-di-tertbutylphenol or phenylenediamines, e.g., N,N'-di-sec-butyl-p-phenylenediamine
  • dyes e.g., N,N'-di-sec-butyl-p-phenylenediamine
  • metal deactivators e.g., N,N'-di-sec-butyl-p-phenylenediamine
  • dehazers such as polyester-
  • Corrosion inhibitors such as a polyhydric alcohol ester of a succinic acid derivative having on at least one of its alpha-carbon atoms an unsubstituted or substituted aliphatic hydrocarbon group having from 20 to 50 carbon atoms, for example, pentaerythritol diester of polyisobutylene-substituted succinic acid, the polyisobutylene group having an average molecular weight of about 950, in an amount from about 1 ppm (parts per million) by weight to about 1000 ppm by weight, may also be present.
  • a polyhydric alcohol ester of a succinic acid derivative having on at least one of its alpha-carbon atoms an unsubstituted or substituted aliphatic hydrocarbon group having from 20 to 50 carbon atoms, for example, pentaerythritol diester of polyisobutylene-substituted succinic acid, the polyisobutylene group having an average molecular weight
  • the fuel compositions of the present invention may also contain one or more detergents.
  • the fuel composition will comprise a mixture of a major amount of hydrocarbons in the gasoline boiling range as described hereinbefore, a minor amount of component (b) as described hereinbefore and a minor amount of one or more detergents.
  • a carrier as described hereinbefore may also be included.
  • the term "minor amount” means less than about 10% by weight of the total fuel composition, preferably less than about 1% by weight of the total fuel composition and more preferably less than about 0.1% by weight of the total fuel composition.
  • the one or more detergents are added directly to the hydrocarbons, blended with one or more carriers, blended with component (b), or blended with component (b) and one or more carriers before being added to the hydrocarbon.
  • the compound of component (b) can be added at the refinery, at a terminal, at a depot, at a retail site, or by the consumer.
  • the treat rate of the fuel additive detergent packages that contains one or more detergents in the final fuel composition is generally in the range of from about 0.007 weight percent to about 0.76 weight percent based on the final fuel composition.
  • the fuel additive detergent package may contain one or more detergents, dehazer, corrosion inhibitor and solvent.
  • a carrier fluidizer may sometimes be added to help in preventing intake valve sticking at low temperature.
  • the Research Octane Number (RON) (ASTM D2699) and Motor Octane Number (MON) (ASTM D2700) will be the techniques used in determining the R+M/2 octane of the fuel.
  • the RON and MON of a spark-ignition engine fuel is determined using a standard test engine and operating conditions to compare its knock characteristic with those of primary reference fuel blends of known octane number. Compression ratio and fuel-air ratio are adjusted to produce standard knock intensity for the sample fuel, as measured by a specific electronic detonation meter instrument system.
  • a standard knock intensity guide table relates engine compression ratio to octane number level for this specific method.
  • the specific procedure for the RON can be found in ASTM D-2699 and the MON can be found in ASTM D-2700.
  • Table I contains the engine conditions necessary in determine the RON and MON of a fuel.
  • the fuels were injected into the bomb and allowed to vaporize fully, than a stoichiometric amount of air was added.
  • the gases were mixed with stirring fans inside the vessel and the contents were heated to the desired temperature. The fans were turned off prior to ignition. Mixtures were ignited using a spark plug. Pressure transducers were flush mounted inside the bob and recorded the pressure rise as a function of time.
  • the base fuel physical properties used in the tests can be found in Table II.
  • Table II Base Fuel Physical Properties Parameter Method Units Base Fuel-1 Base Fuel-2 RON ASTM D2699 95.4 95.3 MON ASTM D2700 86.6 86.4 Density @ 15 °C IP 365 g cm -3 0.7300 0.7293 Oxidation Stability (induction) IP 40 mins > 1440 Unwashed gum IP 131 mg/100ml 6 8 Distillation IP 123 IBP °C 34.9 35.7 10% rec °C 51.8 54.9 20% rec °C 59.9 62.5 30% rec °C 68.1 70.6 40% rec °C 77.8 80.6 50% rec °C 89.7 92.7 60% rec °C 103.1 105.7 70% rec °C 115.6 118.4 80% rec °C 126.7 129.6 90% rec °C 139.6 141.3 95% rec °C 146.9 147.9 FBP °C 167.1 171.4 Residue % vol 1.0 1.0
  • Cyclopropylacetylene in the Base Fuel-1 shows the pressure increase in the combustion chamber 0.1 seconds after ignition of the homogeneous charge is statistically (>95%) significantly greater than the Base Fuel-1 (reference fuel).
  • Base Fuel-1 reference fuel

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Combustion & Propulsion (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Claims (5)

  1. Composition d'essence comprenant (a) une grande quantité d'un mélange d'hydrocarbures dans l'intervalle de distillation de l'essence et (b) une petite quantité de cyclopropylacétylène, le terme « petite quantité » signifiant une quantité inférieure à 50 % en poids de la composition de carburant totale.
  2. Composition de carburant selon la revendication 1, dans laquelle le composant (b) est présent dans une quantité allant de 0,005 % en poids à 20 % en poids sur la base du poids total du carburant.
  3. Composition de carburant selon la revendication 1 ou la revendication 2, comprenant en outre (c) une petite quantité d'un détergent de carburant.
  4. Procédé pour (i) améliorer la vitesse de flamme d'une essence et/ou (ii) augmenter la sensibilité d'une essence, ledit procédé comprenant l'étape consistant à ajouter à une grande quantité d'un mélange d'hydrocarbures dans l'intervalle de distillation de l'essence de petites quantités de cyclopropylacétylène, le terme « petite quantité » signifiant une quantité inférieure à 50 % en poids de la composition de carburant totale.
  5. Utilisation d'une composition d'essence selon la revendication 1 afin d'améliorer la vitesse de flamme d'un moteur à combustion interne dans lequel est introduite la composition d'essence.
EP11729238.3A 2010-06-21 2011-06-20 Composition de carburant et son utilisation Active EP2582777B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US35692210P 2010-06-21 2010-06-21
PCT/US2011/041063 WO2011163122A1 (fr) 2010-06-21 2011-06-20 Composition de carburant et son utilisation

Publications (2)

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EP2582777A1 EP2582777A1 (fr) 2013-04-24
EP2582777B1 true EP2582777B1 (fr) 2016-03-23

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Country Status (6)

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US (1) US20110308140A1 (fr)
EP (1) EP2582777B1 (fr)
CN (1) CN103025853B (fr)
AU (1) AU2011271224B2 (fr)
MY (1) MY160962A (fr)
WO (1) WO2011163122A1 (fr)

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Publication number Priority date Publication date Assignee Title
US20130247856A1 (en) * 2012-03-21 2013-09-26 Shell Oil Company Fuel composition and its use
CN103484173B (zh) * 2013-09-16 2015-05-27 上海交通大学 自点火燃料
WO2015059206A1 (fr) * 2013-10-24 2015-04-30 Shell Internationale Research Maatschappij B.V. Compositions de carburant liquide
EP2949733A1 (fr) * 2014-05-28 2015-12-02 Shell Internationale Research Maatschappij B.V. Compositions d'essence contenant d'absorbants uv de type oxanilide
US20240199965A1 (en) * 2021-04-26 2024-06-20 Shell Usa Inc. Fuel compositions
WO2022228989A1 (fr) * 2021-04-26 2022-11-03 Shell Internationale Research Maatschappij B.V. Compositions de combustible

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Also Published As

Publication number Publication date
CN103025853B (zh) 2015-04-08
WO2011163122A1 (fr) 2011-12-29
AU2011271224B2 (en) 2014-07-03
MY160962A (en) 2017-03-31
AU2011271224A1 (en) 2013-01-10
EP2582777A1 (fr) 2013-04-24
CN103025853A (zh) 2013-04-03
US20110308140A1 (en) 2011-12-22

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