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
  • C10L1/18—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
  • 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
  • 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

• the subject of the present invention is the use of novel polyoxygenated compounds, more specifically cyclic carbonates derivatives, as anti-soot additives for a fuel, in particular for an aviation fuel.
• soot formation is related to a local oxygen deficiency during fuel combustion.
• the mechanisms leading to the formation of these soot particles are still poorly known. They involve complex reactions of nucleation, particle surface growth and coagulation. More specifically, macromolecules formed by pyrolysis or oxidation of hydrocarbons condense to give carbon cores less than 2 nm in diameter. On this core are then adsorbed particles from the gas phase, such as polycylic aromatic compounds or dioxins. Finally, the agglomeration of these primary carbon cores forms a set of particles of size between 10 and 300 nm at the exhaust outlet.
• soot particles are one of the causes of the degradation of air quality, and that they contribute to the phenomenon of global warming. It has also been suggested that soot particles are harmful to health, and more particularly that they are carcinogenic to humans.
• DMC dimethyl carbonate
• DEC diethyl carbonate
• Guo et al. propose the addition, in diesel fuels, of di (2-ethoxyethyl) carbonate ([3], [4]) or methyl 2-ethoxyethyl carbonate [5], to reduce the formation of smoke particles.
• soot emission problem is also encountered in the field of fuels used in aeronautics, mainly during take-off of aircraft (maximum thrust).
• WO 2010/061223 proposes the use of an organic compound, in particular propylene carbonate, to improve the solubilization of a solid ferric compound in a fuel composition.
• these additives do not lower the calorific value of the fuels.
• the purpose of the present invention is precisely to provide new polyoxygenated compounds as additives with anti-soot properties for a fuel, and advantageously for an aviation fuel, in particular a "jet fuel”.
• anti-soot additive is understood to mean a compound which, used in a fuel, for example an aviation fuel, makes it possible to reduce the formation of soot during the combustion of the fuel.
• the anti-soot effectiveness of these polyoxygenated compounds is due to their ability to easily trap the first radical species resulting from the thermal degradation of fuels, which are involved in the formation of soot. More specifically, the polyoxygenated compounds according to the invention are able to rapidly create thermodynamically stable radicals, mainly by stabilizing the radicals in the alpha position of the oxygen atoms.
• cyclic carbonate derivatives according to the invention can be added to automotive fuels, for example gasoline, diesel or diesel fuel, or to aviation fuels.
• Cyclic carbonates derivatives are particularly effective anti-soot additives for aviation fuels for turbine engines used in aeronautics, as detailed more precisely in the following text.
• the invention also relates, in another of its aspects, to a fuel composition, in particular aviation fuel, comprising at least one compound of formula (I) according to the invention.
• a 5-membered heterocycloalkyl group substituted with an oxo group may especially be 1,3-dioxolan-2-one (better known as ethylene carbonate).
• R 4 is chosen from a hydroxyl group, an oxo group and a 4- to 6-membered cyclic carbonate group, in particular ethylene carbonate (1,3-dioxolan-2-one), cyclic carbonate being optionally substituted with one or more C 1-6 -alkyl groups, in particular C 1-4 -alkyl.
• a subgroup of compounds consists of compounds for which represents a single link.
• At least one of R 1 and R 2 advantageously has a conjugated double bond with the double bond of the 1,3-dioxol-2-one ring (conjugated system ⁇ - ⁇ - ⁇ ).
• R 1 and R 2 may represent a C 2-4 -alkenyl group, in particular an ethylene group.
• the cyclic carbonate derivatives used according to the invention have the aforementioned formula (I) in which at least one of R 1 and R 2 comprises a linear, preferably saturated, chain of at least 6 carbon atoms, in particular at least 8 carbon atoms, more particularly at least 10 carbon atoms and preferably 10 to 15 carbon atoms, said sequence being interrupted by one or more oxygen atoms.
• such compounds give the fuel in which they are used, in addition to good anti-soot properties, hot lubrication properties.
• At least one of R 1 and R 2 comprises at least one polyether unit.
• At least one of R 1 and R 2 may, for example, comprise at least one polyethylene glycol unit (X represents a - (CH 2 ) 2 - group) and / or a polypropylene glycol unit (X represents a group - (CH 2 -CH (CH 3 )) -).
• a subgroup of compounds is composed of compounds for which R 1 and R 2 are identical.
• R 1 and R 2 both represent a hydrogen atom or a C 1-4 alkyl group, in particular a methyl group.
• ethylene carbonate 1,3-dioxolan-2-one
• vinylene carbonate named IUPAC: 1,3-dioxol-2-one
• 4,5-dimethyl-1,3-dioxolan-2-one mention may be made of ethylene carbonate (IUPAC name: 1,3-dioxolan-2-one
• ethylene carbonate IUPAC name: 1,3-dioxolan-2-one
• vinylene carbonate named IUPAC: 1,3-dioxol-2-one
• 4,5-dimethyl-1,3-dioxolan-2-one 4,5-dimethyl-1,3-dioxolan-2-one.
• R 1 and R 2 can be defined, independently of one another, according to any one of the above definitions.
• one of R 1 and R 2 represents a hydrogen atom
• the other of R 1 and R 2 represents a group, different from a hydrogen atom, from the groups previously defined.
• R 3 in formula (Ia) above represents a hydrogen atom.
• R 3 in the formula (Ia) above represents a C 1-4 -alkyl group, in particular a methyl group, optionally substituted by a cyclic carbonate of 4 to 6 members, in particular the carbonate of 'ethylene.
• R 3 in formula (Ia) above represents a -C (O) -OR 7 group , with R 7 representing a C 1-4 alkyl group, in particular methyl or ethyl.
• R 3 in the above formula (Ia) represents a C 3 -C 12 -alkyl, in particular C 4-7 -alkyl, linear group, interrupted by one or more oxygen atoms, said alkyl group being optionally substituted by one or more groups selected from a group -OC (O) OR 8 , with R 8 representing a C 1-4 alkyl group, in particular methyl, and a cyclic carbonate group of 4 to 6 members, in particular ethylene carbonate.
• R 3 in formula (Ia) above incorporates at least one polyether unit.
• R 3 may for example comprise at least one polyethylene glycol unit (X represents a - (CH 2 ) 2 - group) and / or a polypropylene glycol unit (X represents a group - (CH 2 -CH (CH 3 )) -) .
• Y in the formula (Ia-i) above represents a C 1-4 -alkyl group, in particular methyl or ethyl.
• Y in formula (Ia-i) above represents a methyl bearing a cyclic carbonate group of 4 to 6 members, in particular ethylene carbonate.
• Another subgroup of compounds is more particularly composed of compounds of formula (Ia-ii) below: in which B represents a covalent bond or a C 1-10 alkylene group, in particular C 1-7 -alkylene, linear or branched, optionally interrupted by one or more oxygen atoms, one or more -OC (O) groups - O- and / or one or more -C (O) O- groups.
• B represents a covalent bond or a C 1-10 alkylene group, in particular C 1-7 -alkylene, linear or branched, optionally interrupted by one or more oxygen atoms, one or more -OC (O) groups - O- and / or one or more -C (O) O- groups.
• B represents a covalent bond
• B represents a C 3-8 -alkylene, in particular C 3-7 -alkylene, linear group, interrupted by one or more oxygen atoms and optionally substituted by one or more -OC groups ( O) OR 8 with R 8 representing a C 1-4 alkyl group, in particular methyl.
• B represents a polyether unit is of type ( ⁇ X-O-) ⁇ n with X and n being as defined above.
• R 7 in formula (Ib) above represents an ethylene carbonate group, optionally substituted with one or more methyl groups.
• cyclic carbonate derivatives may be commercially available or prepared according to synthetic methods described in the literature and known to those skilled in the art.
• the compounds of formula (I) according to the invention may be used as anti-soot additives in a fuel formulation, in particular a diesel fuel, diesel or gasoline for the automobile, or an aviation fuel.
• the invention thus relates to a fuel composition
• a fuel composition comprising at least one compound of formula (I) as defined above.
• the present invention further relates, according to another of its aspects, to a receptacle, in particular a fuel tank of an overhead or land vehicle, containing a fuel supplemented with at least one compound of formula (I) as defined above. .
• the invention also relates to an aircraft or land vehicle, in particular an aircraft, comprising a fuel tank supplemented with at least one compound of formula (I) as defined above.
• a compound of formula (I) according to the invention may be added to a fuel formulation, alone or in combination with one or more other compounds of formula (I).
• the said compound (s) of general formula (I) according to the invention are more particularly introduced into a fuel formulation in a content such that they are soluble in the fuel formulation.
• the said compounds of formula (I) can be used in a conventional formulation of fuel, in particular an aviation fuel, in a proportion of 1 to 40%, in particular from 1 to 20% , relative to the total volume of the fuel composition.
• the fuel composition is an aviation fuel composition.
• Aviation fuel means a fuel intended for use in an aircraft, in particular an airplane, and meeting the international specifications established for aviation fuels as set forth below.
• the aviation fuel composition according to the invention may be a fuel intended for the operation of turbine engine engines (turbojet, turboprop engine), commonly known as “jet fuel” or “jet fuel” in English and, as such, can more particularly meet the standards required for jet fuels, for example those of Jet A-1 jet fuel.
• said one or more compounds of formula (I) may be added to a conventional fuel, for example an aviation fuel.
• a conventional fuel can be supplemented with one or more compounds of formula (I) according to the invention by adding, for example, the compound (s) of formula (I) directly within the tank previously filled with fuel.
• JP-4 MIL-T-5624
• JP-5 JP-7
• JP -8 MIL-T-83133
• ASTM-D Jet A and Jet A-1
• Aviation fuels are based on kerosene, alone or mixed with gasoline (eg 50% kerosene-50% gasoline for JP-4, 99.5% kerosene for JP-5 and JP-8, 100% kerosene for Jet A-1) and include additives adjusted for specific uses of the fuel, such as, for example, antioxidants, corrosion inhibitors, metal catalysis inhibitors, icing inhibitors, in limited quantities.
• gasoline eg 50% kerosene-50% gasoline for JP-4, 99.5% kerosene for JP-5 and JP-8, 100% kerosene for Jet A-1
• additives adjusted for specific uses of the fuel such as, for example, antioxidants, corrosion inhibitors, metal catalysis inhibitors, icing inhibitors, in limited quantities.
• jet fuels are produced from a fraction of kerosene derived directly from the atmospheric distillation of crude oil and whose distillation points are between 140 and 300 ° C, and from carbon chains of 9 to 16 carbon atoms. .
• Aviation fuels have the particularity of having to meet the same levels of specifications worldwide, resulting directly from the particular conditions, in particular extreme temperature variations, in which they are used.
• the properties and specifications of these aviation fuels are more particularly detailed in the document: "Kerosene / Jet Fuel Category Assessment Document", submitted to the US EPA by the American Petroleum Institute, September 21, 2010 .
• Particularly advantageous aviation fuels are, for example, those conforming to the AFQRJOS specification ( "Fuel Fuel Quality Requirements for Jointly Operated Systems") Issue 18 for November 1999 Jet A-1 (this specification incorporates the most stringent criteria of ASTM Specification D 1655 and the British Specification DEF STAN 91-91).
• Jet A1 jet fuel In civil aviation, the most common fuel is Jet A1 jet fuel. This must have a defrost point below -47 ° C (typical value of -50 ° C). Jet-A with a defrost point of -40 ° C is of inferior quality to Jet A-1 and mainly used in the United States; Jet B with a defrost point below -50 ° C, the trade name for JP-4, is only used in very cold climates.
• Jet A-1 must imperatively have a sulfur content of less than 0.30% by weight, and an aromatic content of less than 22% by volume.
• the one or more compounds of formula (I) are added to the conventional fuel, for example a Jet A-1 fuel, in an amount such that they do not affect the specifications to which this fuel must meet.
• an aviation fuel composition according to the invention has a freezing point below -40 ° C, in particular between -60 and -40 ° C, preferably below -47 ° C. ° C, and can thus be adapted to its potential use in cold conditions, for example in the context of use in civil aviation or military.
• an aviation fuel composition according to the invention has a good calorific value, in particular greater than 40 MJ / kg, in particular greater than 42.5 MJ / kg.

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Citations (11)

• 2014
  • 2014-07-24 EP EP14178406.6A patent/EP2977435A1/de not_active Ceased
• 2015
  • 2015-07-16 WO PCT/EP2015/066303 patent/WO2016012343A1/fr active Application Filing

Patent Citations (11)

Non-Patent Citations (8)

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