WO2021225734A1 - Essence automobile à indice d'octane amélioré et procédé d'utilisation - Google Patents

Essence automobile à indice d'octane amélioré et procédé d'utilisation Download PDF

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Publication number
WO2021225734A1
WO2021225734A1 PCT/US2021/026323 US2021026323W WO2021225734A1 WO 2021225734 A1 WO2021225734 A1 WO 2021225734A1 US 2021026323 W US2021026323 W US 2021026323W WO 2021225734 A1 WO2021225734 A1 WO 2021225734A1
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WIPO (PCT)
Prior art keywords
liquid fuel
fuel composition
octane
enhancing additive
indoline compound
Prior art date
Application number
PCT/US2021/026323
Other languages
English (en)
Inventor
David J. Abdallah
Krystal B. Wrigley
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Exxonmobil Research And Engineering Company
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Filing date
Publication date
Priority claimed from US16/869,849 external-priority patent/US11136516B2/en
Application filed by Exxonmobil Research And Engineering Company filed Critical Exxonmobil Research And Engineering Company
Publication of WO2021225734A1 publication Critical patent/WO2021225734A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • 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
    • 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
    • C10L2200/00—Components of fuel compositions
    • C10L2200/04—Organic compounds
    • C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
    • C10L2200/0415—Light distillates, e.g. LPG, naphtha
    • C10L2200/0423—Gasoline
    • 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
    • C10L2200/00—Components of fuel compositions
    • C10L2200/04—Organic compounds
    • C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
    • C10L2200/043—Kerosene, jet fuel
    • 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
    • C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
    • C10L2230/22—Function and purpose of a components of a fuel or the composition as a whole for improving fuel economy or fuel efficiency
    • 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
    • C10L2270/00—Specifically adapted fuels
    • C10L2270/02—Specifically adapted fuels for internal combustion engines
    • 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
    • C10L2270/00—Specifically adapted fuels
    • C10L2270/02—Specifically adapted fuels for internal combustion engines
    • C10L2270/023—Specifically adapted fuels for internal combustion engines for gasoline engines

Definitions

  • This application relates to octane enhancing additives for liquid fuels, and, more particularly, embodiments relate to octane enhancing additives including an indoline compound that improves a liquid fuel’s octane rating.
  • Spark ignition engines can have improved operation when operated with a fuel that provides a sufficient octane rating so that the start of combustion is substantially controlled by the introduction of a spark into the combustion chamber. Fuels that do not have a sufficient octane rating can cause "knocking" in the engine, where at least part of the combustion in the engine is not dependent on the introduction of the spark into the combustion chamber.
  • Organic compounds based on aromatic nitrogen compounds can be effective at less than 1 wt. %.
  • Relevant organic octane enhancing additives based on aromatic nitrogen compounds references include; Jerome E. Brown, Francis X. Markley, Hymin Shapiro, Mechanism of Aromatic Amine Antiknock Action, Industrial & Engineering Chemistry, 1955, 47, 10, p. 2141 and Robert MacKinven, Search for Ash-Free Compounds to Replace Lead Alkyls in Gasoline, Dtsch. Ges. fuer Mineraloelwiss und Kohlechem, 24th Symp. Compend. 74/75, Hamburg, Sep. 30-Oct.
  • NMA N-methyl aniline
  • IOB 3000 - Metal free octane enhancer from Innospec, Inc.
  • tolui dines that have been shown to increase octane in aviation gasoline
  • CVCC constant volume combustion chamber
  • AFIDA Advanced Fuel Ignition Delay Analyzer
  • NMA N-Methyl Analine
  • the example liquid fuel composition may include a liquid fuel and an octane enhancing additive.
  • the octane enhancing additive may include an indoline compound with a bicyclic ring structure, wherein the indoline compound includes a six-membered aromatic ring having two adjacent aromatic carbon atoms with a five membered unsubstituted saturated heterocyclic ring, the five membered saturated heterocyclic ring comprising a nitrogen atom directly bonded to one of the shared carbon atoms, alpha position to the six-membered aromatic ring, to form a secondary amine.
  • the exemplary liquid fuel composition may include a liquid fuel in an amount of about 50 wt.% or greater and an octane enhancing additive.
  • the octane enhancing additive may include an indoline compound having the following structure: wherein Ri, R2, R3, and R4 are individually selected from hydrogen, an alkyl group, an alkenyl group, a heteroatom substituted alkyl group, or a heteroatom substituted alkenyl group.
  • An exemplary method may include combusting in an internal combustion engine a fuel composition including the liquid fuel and an octane enhancing additive.
  • the octane enhancing additive may include an indoline compound with a bicyclic ring structure.
  • the indoline compound may include a six-membered aromatic ring and a five-membered aliphatic ring that share a carbon- carbon aromatic bond.
  • the five-membered aliphatic ring may be heterocyclic and includes a nitrogen positioned in an alpha position to the six-membered aromatic ring.
  • liquid fuel composition comprising: a major amount of a liquid fuel; and a minor amount of an octane enhancing additive comprising an indoline compound with a bicyclic ring structure, wherein the indoline compound comprises a six-membered aromatic ring and a five-membered aliphatic ring that share a carbon-carbon aromatic bond, wherein the five-membered unsubstituted aliphatic ring is heterocyclic and comprises a nitrogen positioned in an alpha position to the six-membered aromatic ring.
  • liquid fuel composition comprising: a liquid fuel in an amount of about 95 wt.% or greater; and from 0.1 wt.% to 5 wt.% of an octane enhancing additive comprising an indoline compound having the following structure: wherein Ri, R2, R3, and R4 are individually selected from hydrogen, an alkyl group, an alkenyl group, a heteroatom substituted alkyl group, or a heteroatom substituted alkenyl group.
  • a method for improving the auto-ignition characteristics of a liquid fuel combusted at high compression ratios comprising: blending a minor amount of an octane enhancing additive into a major amount of liquid fuel to form a liquid fuel composition
  • the octane enhancing additive comprises an indoline compound with a bicyclic ring structure, wherein the indoline compound comprises a six-membered aromatic ring and a five- membered aliphatic ring that share a carbon-carbon aromatic bond, wherein the five-membered aliphatic ring is heterocyclic and comprises a nitrogen positioned in an alpha position to the six- membered aromatic ring, and combusting in an internal combustion engine a fuel composition comprising the liquid fuel and an octane enhancing additive, wherein the octane enhancing additive comprises an indoline compound with a bicyclic ring structure, wherein the indoline compound comprises a six
  • FIG. 1 shows a dP/dt curve from AFIDA testing apparatus for determining combustion ignition delay based on the heat release curves for isooctane and also isooctane with octane enhancing additives.
  • FIG. 2 shows a dP/dt curve from AFIDA testing apparatus for determining combustion ignition delay based on the heat release curves for isooctane and also isooctane with octane enhancing additives 7-methylindoline, 5-methylindoline, and 5 -methoxy indoline.
  • “Major amount” as it relates to components included within the liquid fuel compositions of the specification and the claims means greater than or equal to 50 wt.%, or greater than or equal to 60 wt.%, or greater than or equal to 70 wt.%, or greater than or equal to 80 wt.%, or greater than or equal to 90 wt.%, based on the total weight of the liquid fuel composition.
  • Minor amount as it relates to components included within the liquid fuel compositions of the specification and the claims means less than 50 wt.%, or less than or equal to 40 wt.%, or less than or equal to 30 wt.%, or greater than or equal to 20 wt.%, or less than or equal to 10 wt.%, or less than or equal to 5 wt.%, or less than or equal to 2 wt.%, or less than or equal to 1 wt.%, based on the total weight of the liquid fuel composition.
  • “Essentially free” as it relates to components included within the liquid fuel compositions of the specification and the claims means that the particular component is at 0 weight % within the liquid fuel composition, or alternatively is at impurity type levels within the liquid fuel composition (less than 100 ppm, or less than 20 ppm, or less than 10 ppm, or less than 1 ppm). [0020] All percentages in describing liquid fuel compositions herein are by weight unless specified otherwise. “Wt.%” means percent by weight.
  • the present application discloses a new nitrogen containing organic octane enhancing additive.
  • Indoline has been found to increase octane rating as much as NMA in ethanol free gasoline (E0) and gasoline containing 10% ethanol (E10).
  • E0 ethanol free gasoline
  • E10 10% ethanol
  • indoline may also improve the thermal stability of the fuel which is especially important when using additives at the relatively high levels (more than ppm levels) necessary for organic octane enhancers.
  • This application relates to octane enhancing additives for liquid fuels, and, more particularly, embodiments relate to octane enhancing additives including an indoline compound and methods that improve a liquid fuel composition’s octane rating.
  • the octane enhancing additives improve a liquid fuel composition’s octane rating.
  • the octane enhancing additive should extend the combustion ignition delay of the vaporized fuel composition.
  • the combustion ignition delay is the time between liquid fuel injection and combustion of the fuel vapors in the combustion chamber. By extending the ignition delay, spark timing can be advanced to improve engine efficiency.
  • Suitable octane enhancing additives may include an indoline compound.
  • Indoline compounds have a bicyclic ring structure and include a six-membered aromatic ring and a five- membered aliphatic ring sharing a carbon-carbon aromatic bond.
  • the aliphatic ring is heterocyclic and includes nitrogen positioned alpha (i.e., adjacent) to the aromatic ring.
  • the aromatic ring may be heterocyclic or carbocyclic.
  • the aromatic ring may be substituted.
  • Exemplary substituents may include, but are not limited to, alkyl groups, alkenyl groups, heteroatom substituted alkyl groups, or heteroatom substituted alkenyl groups.
  • Suitable heteroatoms that may be substituted may include, but are not limited to, nitrogen, oxygen, and sulfur, among others.
  • 2-methylindoline additive may find application in diesel fuels for compression ignition combustion engines, which are typically diesel engines. Because of this property, 2-methylindoline would not be a suitable additive for use in a spark-ignition engine as it would lower the octane rating of the fuel.
  • Suitable octane enhancing additives including an indoline compound may include, but are not limited to, a bicyclic ring structure of Formula (1) as follows: wherein Ri, R2, R3, and R4 are individually selected from hydrogen, an alkyl group, an alkenyl group, a heteroatom substituted alkyl group, or a heteroatom substituted alkenyl group.
  • Suitable heteroatoms that may be substituted may include, but are not limited to, nitrogen, oxygen, and sulfur, among others.
  • the alkyl or alkenyl (or heteroatom substituted) groups of Ri, R2, R3, and R4 may be the same or different and, in some embodiments, may include 1 carbon atom to 18 carbon atoms, or, more particularly, include 1 carbon atom to 2 carbon atoms.
  • Ri, R2, R3, and R4 are each hydrogen.
  • a suitable octane enhancing additive including an indoline compound may include, but are not limited to, a bicyclic ring structure of Formula (2) as follows: present in the liquid fuel composition in an amount ranging from about 0.01 wt. % to about 50 wt.% and, more particularly, ranging from about 0.1 wt. % to about 10 wt.%, or about 0.2 wt. % to about 9 wt.%, or about 0.3 wt. % to about 8 wt.%, or about 0.4 wt. % to about 7 wt.%, or about 0.5 wt. % to about 6 wt.%, or about 0.6 wt.
  • Formula (2) as follows: present in the liquid fuel composition in an amount ranging from about 0.01 wt. % to about 50 wt.% and, more particularly, ranging from about 0.1 wt. % to about 10 wt.%, or about 0.2 wt. % to
  • the appropriate amount of the octane enhancing additive may be based on a number of factors, including, but not limited to, fuel system operating conditions, the particular aromatic carbocycbc ring and substituents thereon, and the liquid fuel’s hydrocarbon components, among others.
  • the octane enhancing additive including an indobne compound may be included in a liquid fuel composition to extend an octane rating of the liquid fuel composition, which should result in improved combustion.
  • the octane rating may be extended as compared to the liquid fuel composition without the octane enhancing additive, for example, from about 0.5 to 10, or 0.7 to 8, or 0.9 to 6, or 1.0 to 8, or 1.2 to 6, or 1.4 to 4, or 1.6 to 3, or 1.8 to 2.5, or 2.0 to 2.4 octane ratings than the fuel without the additive.
  • the octane enhancing is determined using the RON and MON rating tests methods.
  • the octane enhancing additive including an indobne compound may be included in a liquid fuel composition to extend the ignition delay of the liquid fuel composition, which should result in improved turbine combustion.
  • the ignition delay may be extended as compared to the liquid fuel composition without the octane enhancing additive. Delaying the ignition of the fuel allows an increase premixing of the fuel sprayed into a combustion chamber with the compressed air in a turbine engine. Increase premixing lowers emissions and avoids fuel ignition in close proximity of the nozzle that can cause nozzle coking.
  • the octane enhancing additive may be introduced into a fuel system of an internal combustion engine.
  • the octane enhancing combination may be combined with the liquid fuel composition in the internal combustion engine.
  • the octane enhancing composition may be introduced into the internal combustion engine as a component of the liquid fuel composition.
  • the liquid fuel composition may be burned.
  • Suitable internal combustion engines may include, but are not limited to, rotary, turbine, spark ignition, 2-stroke, or 4-stroke engines.
  • the internal combustion engines include, aviation piston and turbine engines, aviation supersonic turbine engines, and automobile and truck engines.
  • the internal combustion engine may comprise a direct injection engine.
  • the liquid fuel composition may further include a liquid fuel.
  • the liquid fuel may include, but are not limited to, motor gasoline, aviation gasoline, aviation turbine fuel, and supersonic fuel. Combinations of different liquid fuels may also be used.
  • Motor gasoline includes a complex mixture of relatively volatile hydrocarbons blended to form a fuel suitable for use in spark-ignition engines. Motor gasoline, as defined in ASTM Specification D4814, is characterized as having a boiling range of 50 °C to 70 °C at the 10-percent recovery point to 185 °C to 190 °C at the 90-percent recovery point.
  • the aviation turbine fuels can be a petroleum distillate as defined by ASTM specification D1655.
  • the aviation gasoline can be mixture of various isooctanes, isoalkanes and aromatics compounds as defined by ASTM specification D910.
  • the supersonic fuel can be a compound mixture composed primarily of hydrocarbons; including alkanes, cycloalkanes, alkylbenzenes, indanes/tetrabns, and naphthalenes.
  • a supersonic fuel is a fuel that meets the specification for propellant, rocket grade kerosene (either RP-1 or RP-2) in MIL-DTL-25576, dated April 14, 2006.
  • Supersonic fuels are typically capable of standing up to higher heats (without undesirable breakdown) from air friction on the aircraft at speeds greater than the speed of sound.
  • Fuel that breaks down can cause deposits that potentially restrict fuel flow in fuel lines.
  • suitable liquid fuels may include, but are not limited to, an alcohol, an ether, or combinations thereof.
  • the alternative fuels may include, but are not limited to, methanol, ethanol, diethyl ether, and methyl t-butyl ether.
  • the liquid fuel may include a mixture of a motor gasoline and ethanol.
  • the liquid fuel may be present in the liquid fuel composition with the octane enhancing additive in any suitable amount.
  • the liquid fuel may include any suitable liquid fuel, including a combination of two or more different fuels.
  • the liquid fuel may be present in the liquid fuel composition in an amount ranging from about 0.01 wt.
  • % to about 99.9 wt.% or from 0.05 wt.% to about 99.5 wt.%, or from 0.1 wt.% to about 99 wt.%, or from 0.5 wt.% to about 98 wt.%, or from 1 wt.% to about 97 wt.%, or from 3 wt.% to about 95 wt.%, or from 5 wt.% to about 90 wt.%, or from 10 wt.% to about 85 wt.%, or from 15 wt.% to about 80 wt.%, or from 20 wt.% to about 70 wt.%, or from 30 wt.% to about 60 wt.%, or from 40 wt.% to about 50 wt.%.
  • One of ordinary skill in the art should be able to select an appropriate liquid fuel and amount thereof to include in the liquid fuel composition for a particular application.
  • additional additives can be included in the liquid fuel composition as desired by one of ordinary skill in the art for a particular application.
  • additional additives include, but are not limited to, detergents, rust inhibitors, corrosion inhibitors, lubricants, antifoaming agents, demulsifiers, conductivity improvers, metal deactivators, cold-flow improvers, cetane improvers and fluidizers, among others.
  • detergents rust inhibitors, corrosion inhibitors, lubricants, antifoaming agents, demulsifiers, conductivity improvers, metal deactivators, cold-flow improvers, cetane improvers and fluidizers, among others.
  • the effect of octane-boosting indoline on the octane number of two different base fuels for a spark-ignition internal combustion engine was measured.
  • the additive was added to the fuels at a relatively low treat rate of 0.6 wt.% (weight additive / weight base fuel).
  • the first fuel was a base gasoline with 0 vol.% ethanol (E0).
  • the second fuel was a base gasoline containing 10 vol.% ethanol (E10).
  • the RON and MON of the base fuels, as well as the blends of base fuel and octane enhancing additive, were determined according to ASTM D2699 and ASTM D2700, respectively.
  • the octane enhancing additive was an indoline compound of Formula 2 above. For comparative purposes, the octane rating for the same motor gasoline was also tested with NMA, a commercial octane enhancing additive.
  • FIG. 1 shows the dP/dt trace used for determining the combustion ignition delay for these tests.
  • octane enhancing additive extended the combustion ignition delay for isooctane by 1.9 msec.
  • a comparative commercially available octane enhancer additive, NMA shows a similar combustion ignition delay of 2.0 msec in isooctane.
  • indoline additives with substitutions on the 6 member aromatic ring.
  • An octane enhancing additive was added to isooctane in an amount of 0.3 wt%.
  • the ignition delay was then measured for isooctane and isooctane with 0.3 wt % additive using an AFIDA 2805 - Advanced Fuel Ignition Delay Analyzer. AFIDA conditions are highlighted in the Table 2 above.
  • FIG. 2 shows the dP/dt trace used for determining the combustion ignition delay for these tests.
  • compositions, methods, and processes are described herein in terms of “comprising,” “containing,” “having,” or “including” various components or steps, the compositions and methods can also “consist essentially of’ or “consist of’ the various components and steps.
  • ranges from any lower limit may be combined with any upper limit to recite a range not explicitly recited, as well as, ranges from any lower limit may be combined with any other lower limit to recite a range not explicitly recited, in the same way, ranges from any upper limit may be combined with any other upper limit to recite a range not explicitly recited.

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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)

Abstract

L'invention concerne des additifs améliorant l'indice d'octane et des procédés qui améliorent l'indice d'octane d'une composition de carburant liquide. Une composition de carburant liquide peut comprendre un carburant liquide et un additif améliorant l'indice d'octane. L'additif améliorant l'indice d'octane peut comprendre un composé indoline présentant une structure cyclique bicyclique, le composé indoline comprenant un cycle aromatique à six chaînons et un cycle aliphatique à cinq chaînons qui partagent une liaison aromatique carbone-carbone. Le cycle aliphatique à cinq chaînons peut être hétérocyclique et peut comprendre un azote positionné dans une position alpha par rapport au cycle aromatique à six chaînons.
PCT/US2021/026323 2020-05-08 2021-04-08 Essence automobile à indice d'octane amélioré et procédé d'utilisation WO2021225734A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US16/869,849 US11136516B2 (en) 2018-12-07 2020-05-08 Motor gasoline with improved octane and method of use
US16/869,849 2020-05-08

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WO2021225734A1 true WO2021225734A1 (fr) 2021-11-11

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2881061A (en) * 1956-03-12 1959-04-07 Socony Mobil Oil Co Inc Anti-knock gasoline containing hydrogenated quinolines and indoles
US5470358A (en) 1993-05-04 1995-11-28 Exxon Research & Engineering Co. Unleaded aviation gasoline
US20030110684A1 (en) * 2001-12-18 2003-06-19 Henly Timothy J. Extremely stable diesel fuel compositions
US20090107555A1 (en) 2007-10-31 2009-04-30 Aradi Allen A Dual Function Fuel Atomizing and Ignition Additives
US20120024751A1 (en) * 2010-07-30 2012-02-02 Chevron U.S.A., Inc. Denitrification of a hydrocarbon feed
WO2020117522A1 (fr) * 2018-12-07 2020-06-11 Exxonmobil Research And Engineering Company Additif antioxydant à haute température pour carburant

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2881061A (en) * 1956-03-12 1959-04-07 Socony Mobil Oil Co Inc Anti-knock gasoline containing hydrogenated quinolines and indoles
US5470358A (en) 1993-05-04 1995-11-28 Exxon Research & Engineering Co. Unleaded aviation gasoline
US20030110684A1 (en) * 2001-12-18 2003-06-19 Henly Timothy J. Extremely stable diesel fuel compositions
US20090107555A1 (en) 2007-10-31 2009-04-30 Aradi Allen A Dual Function Fuel Atomizing and Ignition Additives
US20120024751A1 (en) * 2010-07-30 2012-02-02 Chevron U.S.A., Inc. Denitrification of a hydrocarbon feed
WO2020117522A1 (fr) * 2018-12-07 2020-06-11 Exxonmobil Research And Engineering Company Additif antioxydant à haute température pour carburant

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
JEROME E. BROWNFRANCIS X. MARKLEYHYMIN SHAPIRO: "Mechanism of Aromatic Amine Antiknock Action", INDUSTRIAL & ENGINEERING CHEMISTRY, vol. 47, no. 10, 1955, pages 2141
KUNO SCHÄDLICH1 ET AL: "Octane Enhancers", ULLMANN'S ENCYCLOPEDIA OF INDUSTRIAL CHEMISTRY, XX, XX, 1 January 2005 (2005-01-01), pages 1 - 15, XP007908552, DOI: 10.1002/14356007.A18 037 *
ROBERT MACKINVEN: "Search for Ash-Free Compounds to Replace Lead Alkyls in Gasoline", DTSCH. GES. FUER MINERALOELWISS UND KOHLECHEM, 24TH SYMP. COMPEND. 74/75, vol. 2, 30 September 1974 (1974-09-30), pages 687

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