US20110308140A1 - Fuel composition and its use - Google Patents

Fuel composition and its use Download PDF

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Publication number
US20110308140A1
US20110308140A1 US13/164,202 US201113164202A US2011308140A1 US 20110308140 A1 US20110308140 A1 US 20110308140A1 US 201113164202 A US201113164202 A US 201113164202A US 2011308140 A1 US2011308140 A1 US 2011308140A1
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United States
Prior art keywords
fuel
carbon atoms
fuel composition
group
gasoline
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Abandoned
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US13/164,202
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English (en)
Inventor
Roger Francis Cracknell
Yajnanarayana Halmuthur Jois
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Shell USA Inc
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Shell Oil Co
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Priority to US13/164,202 priority Critical patent/US20110308140A1/en
Assigned to SHELL OIL COMPANY reassignment SHELL OIL COMPANY ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CRACKNELL, ROGER FRANCIS, JOIS, YAJNANARAYANA HALMUTHUR
Publication of US20110308140A1 publication Critical patent/US20110308140A1/en
Abandoned legal-status Critical Current

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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.
  • a gasoline composition comprising (a) a major amount of a mixture of hydrocarbons in the gasoline boiling range and (b) a minor amount of at least one hydrocarbon having 5 to 12 carbon atoms and containing at least one cyclopropyl group and at least one acetylenic group.
  • the present invention provides a method of improving the flame speed of a gasoline which comprises adding to a major portion of a gasoline mixture, minor amount of the additive described above.
  • the present invention provides a method for operating a spark ignition engine which comprises burning in said engine such fuel composition described above.
  • FIG. 1 represents the Schlieren images of single combustion event 30 ms after ignition of Base Fuel-1 plus 20% Cyclopropylacetylene.
  • FIG. 2 represents the Schlieren images of single combustion event 30 ms after ignition of Base Fuel-1 only.
  • FIG. 3 represents improvement in Hyundai Acceleration Performance of the Faster Flame Speed fuel blends versus Base Fuel-2 (reference fuel); all additive concentrations in ppmw.
  • 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 at least one hydrocarbon having 5 to 12 carbon atoms and containing at least one cyclopropyl group and at least one acetylenic group.
  • acetylenic group refers to unsaturated hydrocarbons that have carbon atoms in chains linked by one or more triple bonds.
  • the component (b) can be a compound having the formula:
  • n is an integer from 0 to 7;
  • R 1 to R 6 are independently 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 atome, with the proviso that the total number of carbon atoms in the compound are from 5 to 12.
  • n is an integer from 0 to 5, more preferably 0 to 3.
  • R 1 to R 6 are independently hydrogen, alkyl group having 1 to 5, more preferably 1 to 3 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 org. base in a chlorinated hydrocarbon with dehydrochlorination of the mixt. of alpha,-alpha dichlorocyclopropane and alpha-chlorovinylcyclopropane (with base at reflux in a solvent) and simultaneous distillation.
  • Cyclopropyl 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 Best). 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.
  • the preferred cyclopropyl group-containing acetylenic compounds maybe, 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.
  • An effective amount of one or more compounds of component (b), more particularly Formula I, are 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 one or more compounds of component (b) to the fuel.
  • one or more compounds of 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.
  • each compound of 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, each compound of 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 one or more compounds 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 one or more compounds of component (b), or blended with one or more compounds of component (b) and one or more carriers before being added to the hydrocarbon.
  • the compounds 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.
  • 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
  • Cyclopropylacetylene, 1-Pentyne were blended at 0.5% and 1.0% into Base Fuel-2. Each fuel blend was tested in a single day along with the reference fuel (base fuel without the additive) in an A-B-A-B . . . type test design on the chassis dynamometer. A Hyundai Coupe was used for the testing. As this vehicle has shown to be insensitive to changes in fuel octane the improvements in acceleration performance achieved between the test and reference fuel are attributed to changes in the laminar flame speed of the fuel. A standard chassis dynamometer power and acceleration test procedure on a Hyundai Coupe was used to obtain these results as shown in FIG. 3 . The figure shows over 0.2% acceleration performance improvements with 1% cyclopropylacetylene as an additive as compared to the base fuel without the additive.

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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)
US13/164,202 2010-06-21 2011-06-20 Fuel composition and its use Abandoned US20110308140A1 (en)

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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)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2641960A1 (fr) * 2012-03-21 2013-09-25 Shell Internationale Research Maatschappij B.V. Composition de carburant et son utilisation
WO2015059206A1 (fr) * 2013-10-24 2015-04-30 Shell Internationale Research Maatschappij B.V. Compositions de carburant liquide
WO2022228990A1 (fr) * 2021-04-26 2022-11-03 Shell Internationale Research Maatschappij B.V. Compositions de carburant
WO2022228989A1 (fr) * 2021-04-26 2022-11-03 Shell Internationale Research Maatschappij B.V. Compositions de combustible

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103484173B (zh) * 2013-09-16 2015-05-27 上海交通大学 自点火燃料
EP2949733A1 (fr) * 2014-05-28 2015-12-02 Shell Internationale Research Maatschappij B.V. Compositions d'essence contenant d'absorbants uv de type oxanilide

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US6287351B1 (en) * 1999-02-25 2001-09-11 Go Tec, Inc. Dual fuel composition including acetylene for use with diesel and other internal combustion engines
US20030015268A1 (en) * 2001-07-03 2003-01-23 Dobbins Thomas A. Catalyst system for rendering organic propellants hypergolic with hydrogen peroxide
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US6858048B1 (en) * 2001-04-18 2005-02-22 Standard Alcohol Company Of America, Inc. Fuels for internal combustion engines
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Publication number Priority date Publication date Assignee Title
GB419690A (en) * 1933-02-23 1934-11-16 Standard Oil Dev Co Improvements relating to motor fuels
US2869320A (en) * 1954-07-06 1959-01-20 Phillips Petroleum Co Hypergolic fuel and its method of use in developing thrust
GB1495509A (en) * 1973-11-26 1977-12-21 Trustag Bv Engine fuels and their preparation
US4372753A (en) * 1980-04-23 1983-02-08 Source Technology, Inc. Liquid fuel for use in internal combustion engines
US5771847A (en) * 1996-06-24 1998-06-30 The United States Of America As Represented By The Secretary Of The Navy Fuel oxidizer emulsion injection system
US6287351B1 (en) * 1999-02-25 2001-09-11 Go Tec, Inc. Dual fuel composition including acetylene for use with diesel and other internal combustion engines
US6858048B1 (en) * 2001-04-18 2005-02-22 Standard Alcohol Company Of America, Inc. Fuels for internal combustion engines
US20030015268A1 (en) * 2001-07-03 2003-01-23 Dobbins Thomas A. Catalyst system for rendering organic propellants hypergolic with hydrogen peroxide
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US7217851B1 (en) * 2004-03-31 2007-05-15 United States Of America As Represented By The Secretary Of The Air Force Synthesis of butadiynes

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2641960A1 (fr) * 2012-03-21 2013-09-25 Shell Internationale Research Maatschappij B.V. Composition de carburant et son utilisation
CN103320181A (zh) * 2012-03-21 2013-09-25 国际壳牌研究有限公司 燃料组合物及其用途
WO2015059206A1 (fr) * 2013-10-24 2015-04-30 Shell Internationale Research Maatschappij B.V. Compositions de carburant liquide
WO2022228990A1 (fr) * 2021-04-26 2022-11-03 Shell Internationale Research Maatschappij B.V. Compositions de carburant
WO2022228989A1 (fr) * 2021-04-26 2022-11-03 Shell Internationale Research Maatschappij B.V. Compositions de combustible

Also Published As

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CN103025853B (zh) 2015-04-08
WO2011163122A1 (fr) 2011-12-29
EP2582777B1 (fr) 2016-03-23
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

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