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
  • C10L1/16—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
• Fuel blenders have to design products which perform well under such diverse conditions. This naturally requires compromise, as often times fuel properties or engine
• thermodynamic efficiency A faster burn velocity also serves to maximize conversion of the fuel, thereby increasing the overall fuel economy and reducing emissions.
• the flame speed (related to burning velocity) of combustible fuel plays an important role in fuels chemistry and in the performance of engines (power) and emissions from spark-ignition engines.
• 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.
• Fig. 1 represents the Schlieren images of single
• Fig. 2 represents the Schlieren images of single
• 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).
• 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 x to R6 are
• n is an integer from 0 to 5, more preferably 0 to 3.
• Ri to ]3 ⁇ 4 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 PCI5 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, (see Dolgii, I. E .
• Dicyclopropylacetylenic derivatives can be prepared using Favorskii reaction and common organic systhesis procedure (Nefedov, 0. M. ; Dolgii, I. E . ; Shvedova, I. B . ;
• Cycopropyl Cyanide can be prepared by the reaction of sodium amide with
• the preferred cyclopropyl group-containing acetylenic compounds maybe, for example, cyclopropyl acetylene; 1-cyclopropyl-l- propyne; l-cyclopropyl-2-propyne ; 1-methyl-l-ethynyl- cyclopropane ; 2-methyl-l-ethynyl-cyclopropane ; 1,1- (3- methylene-l-propyne-1 , 3-diyl ) bis- ; 1 , 1-bicyclopropyl , 2,2- diethynyl-; 1-cyclopropylpenta-l , 3-diyne ; cyclopropane, 1,1- ( 1 , 3-butadiyne-l , 4-diyl ) bis- ; cyclopropane, 1 , 1- ( 3-methyl-l- propyne-1 , 3-diyl ) bis- ; and 1 , 4-dic
• 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) the term "minor amount” means less than 50% by weight of the total fuel composition, preferably less than 30% by weight of the total fuel composition.
• minor amount will contain at least some amount, preferably at least 0.001% by weight of the total fuel composition.
• component (b) 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 20% by weight, especially from 0.005% by weight, more preferably from 0.05% by weight, even more preferably from 0.5% by weight, most preferably from 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 25°C to 232°C and comprise mixtures of
• saturated hydrocarbons olefinic hydrocarbons and aromatic hydrocarbons.
• the base fuel is derived from straight run gasoline, polymer gasoline, natural gasoline, dimer and trimerized olefins, synthetically produced aromatic hydrocarbon
• hydrocarbon composition and octane level of the base fuel are not
• the octane level, (R+M)/2 will generally be above 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 0.1% by volume to 15% by volume of the base fuel, although larger amounts may be utilized.
• the fuels can also contain
• antioxidants such as
• phenolics e.g., 2 , 6-di-tertbutylphenol or phenylenediamines , e.g., N, ' -di-sec-butyl-p-phenylenediamine, dyes, metal deactivators, dehazers such as polyester-type ethoxylated alkylphenol-formaldehyde resins.
• Corrosion inhibitors such as a polyhydric alcohol ester of a succinic acid derivative having on at least one of its alpha-carbon atoms an
• pentaerythritol diester of polyisobutylene-substituted succinic acid the polyisobutylene group having an average molecular weight of about 950, in an amount from 1 ppm (parts per million) by weight to 1000 ppm by weight, may also be present.
• the fuel compositions of the present invention may also contain one or more detergents.
• detergents are used to prepare for 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
• detergents means less than 10% by weight of the total fuel composition, preferably less than 1% by weight of the total fuel
• 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
• component (b) or blended with one or more compounds of component (b) and one or more carriers before being added to the
• 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 0.007 weight percent to 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.
• combustion vessel a stainless sphere of 30 liter volume and with extensive optical access.
• 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.
• acetylenic group significantly enhanced the flame speed of the given fuel composition.
• 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 as an additive as compared to the base fuel without the additive.
• the benefit of this increase in flame speed is best utilized in performance a applications such as racing fuel and premium fuel. Addition of such molecules in fuels typically results in less pollution, more power and better efficiency. Faster burning fuels allow engines to run on lean mixtures of gasoline and air, potentially reducing nitrogen oxide and hydrocarbon emissions.
• the flame speed of the cyclopropyl acetylene in gasoline is greatly increased without lowering the RON value.
• the fuel composition of the invention increases fuel sensitivity. There are industry reports that indicate fuel with higher sensitivity (lower MON) has better anti-knock quality.

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

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• 2011
  • 2011-06-20 CN CN201180036755.1A patent/CN103025853B/zh not_active Expired - Fee Related
  • 2011-06-20 WO PCT/US2011/041063 patent/WO2011163122A1/en active Application Filing
  • 2011-06-20 EP EP11729238.3A patent/EP2582777B1/de active Active
  • 2011-06-20 US US13/164,202 patent/US20110308140A1/en not_active Abandoned
  • 2011-06-20 AU AU2011271224A patent/AU2011271224B2/en not_active Ceased
  • 2011-06-20 MY MYPI2012701216A patent/MY160962A/en unknown

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