EP2977433A1 - Zyklische Acetalderivate als Antirußzusätze für einen Flugzeug-Treibstoff - Google Patents

Zyklische Acetalderivate als Antirußzusätze für einen Flugzeug-Treibstoff Download PDF

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Publication number
EP2977433A1
EP2977433A1 EP14178407.4A EP14178407A EP2977433A1 EP 2977433 A1 EP2977433 A1 EP 2977433A1 EP 14178407 A EP14178407 A EP 14178407A EP 2977433 A1 EP2977433 A1 EP 2977433A1
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EP
European Patent Office
Prior art keywords
group
groups
alkyl
formula
fuel
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
EP14178407.4A
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English (en)
French (fr)
Inventor
désignation de l'inventeur n'a pas encore été déposée La
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Rhodia Operations SAS
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Rhodia Operations SAS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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Priority to EP14178407.4A priority Critical patent/EP2977433A1/de
Priority to PCT/EP2015/066305 priority patent/WO2016012345A1/fr
Publication of EP2977433A1 publication Critical patent/EP2977433A1/de
Ceased legal-status Critical Current

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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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
    • 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
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • 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
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
    • C10L1/1855—Cyclic ethers, e.g. epoxides, lactides, lactones
    • 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 of cyclic acetal derivatives, as anti-soot additives for aviation fuels, in particular fuels intended for turbine engine engines. better known as "jet-fuels" in English.
  • 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.
  • 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 referred to later in the text.
  • Jet fuel Aviation fuels, in particular fuels intended for the operation of turbine engine engines (turbojet engine, turboprop engine), commonly known as “jet fuel”, and better known by the English-language names “jet-fuels” or “Aviation Turbine” Fuels “(ATF), are kerosene-based blends, alone or mixed with gasoline, distinct from diesel fuels used in the automotive field. They must meet very strict specifications because of their particular constraints of use. In particular, the performance of the fuel under very low temperature conditions is one of the major concerns in the field of jet-fuels, in particular to reduce the risk of clogging related to the precipitation of compounds at low temperatures.
  • the present invention aims precisely to provide new additives, suitable for use in aviation fuels, and to reduce the formation of soot.
  • these additives do not lower the calorific value of the fuels.
  • R 4 is C 1-20 -alkyl, in particular C 1-12 -alkyl, linear or branched, optionally interrupted by one or more oxygen atoms, one or more groups -OC (O) -O- and / or one or more -C (O) O- groups; and optionally substituted by one or more heterocycloalkyl groups of 3 to 6 members and containing 1 to 3 oxygen atoms, in particular a dioxolane or dioxane group, said heterocycloalkyl groups possibly being substituted with one or more C 1-6 groups; alkyl and / or oxo; as an anti-soot additive for aviation fuel.
  • anti-soot additive is meant a compound which, used in a fuel, in particular an aviation fuel, reduces the formation of soot during the combustion of the fuel.
  • the invention also relates, in another of its aspects, to an aviation fuel composition, in particular fuel for aircraft engines to turbine ("jet fuel”), comprising at least one compound of formula (I) according to the invention.
  • aviation fuel composition in particular fuel for aircraft engines to turbine (“jet fuel”), comprising at least one compound of formula (I) according to the invention.
  • a subgroup of compounds is composed of compounds for which m is 0, that is to say compounds of formula (I ') below: wherein R 1 , R 2 and R 3 are as defined above.
  • R 1 and R 2 in formula (I) or (I ') above, represent, independently of one another, a group chosen from a hydrogen atom; a C 1-4 alkyl group, in particular methyl; or phenyl.
  • R 1 and R 2 are both methyl.
  • R 3 represents a C 1-4 -alkyl group, in particular methyl, optionally substituted by one or more heterocycloalkyl groups of 4 to 6 members and containing 1 to 3 oxygen atoms, said heterocycloalkyl groups which may be optionally substituted by one or more C 1-4 -alkyl groups.
  • R 3 represents a C 3-12 -alkyl group, in particular C 4-7 -alkyl, interrupted by one or more oxygen atoms, and optionally substituted by one or more heterocycloalkyl groups of 4 6-membered ring and containing 1 to 3 oxygen atoms, said heterocycloalkyl groups may be optionally substituted with one or more C 1-4 -alkyl groups.
  • said heterocycloalkyl group is chosen from 1,3-dioxane, 1,3-dioxolane, 2,2-dimethyl-1,3-dioxane and 2,2-dimethyl-1,3-dioxolane.
  • At least one of R 1 , R 2 and R 3 , in particular R 3 comprises a linear, preferably saturated, chain of at least 6 carbon atoms, in particular from less 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.
  • R 3 in the above general formula (I) or (I ') is different from the group -C (O) -OC 2 H 5 .
  • R 3 comprises 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 - (CH 2 -CH (CH 3 ) group ) -).
  • Y represents a C 1-4 alkyl group, in particular methyl or ethyl.
  • Y represents a methyl bearing a 1,3-dioxane, 1,3-dioxolane, 2,2-dimethyl-1,3-dioxane or 2,2-dimethyl-1,3-dioxolane group.
  • m and p in the aforementioned formula (Ib) are identical, and preferably are 0.
  • 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.
  • B represents a polyether unit of the type ( ⁇ X-O) ⁇ n , with X and n being as defined previously.
  • a subgroup of compounds is constituted by the compounds of general formula (I) in which both m and / or R 1 and / or R 2 and / or R 3 are such defined in the subgroups and specific modes above.
  • Cyclic acetal derivatives may be commercially available or prepared according to synthetic methods described in the literature and known to those skilled in the art.
  • cyclic acetals according to the invention can be prepared from glycerol acetals of general structure:
  • glycerol acetals may themselves be prepared according to synthetic methods known to those skilled in the art, in particular by reaction, generally in acidic medium, of an aldehyde or a ketone on glycerol or by transacetalization reaction. , as for example described in the document EP 1 321 503 .
  • the cyclic acetals of formula (I) according to the invention may be used as anti-soot additives in an aviation fuel formulation.
  • the invention thus relates to an aviation fuel composition
  • an aviation fuel composition comprising at least one compound of formula (I) as defined above.
  • the present invention further relates, in another of its aspects, a fuel tank for an aircraft, in particular an aircraft, containing a fuel supplemented with at least one compound of formula (I) as defined above.
  • the invention also relates to an aircraft, 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) may be used in a conventional formulation of aviation fuel, in a proportion of 1 to 40%, in particular from 1 to 20%, relative to the volume total fuel composition.
  • the aviation fuel composition according to the invention may be a fuel intended for the operation of turbine engine engines (turbojet engine, 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.
  • the one or more compounds of formula (I) can be added to a conventional aviation fuel.
  • a conventional aviation fuel can be supplemented with one or more compounds of formula (I) according to the invention by adding, for example, the compound or compounds of formula (I) directly within the reservoir of the aircraft 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 worldwide the same levels of specifications, resulting directly from the conditions particular, 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 fuels for aircraft are, for example, those conforming to the specification AFQRJOS ("Aviation Fuel Quality Requirements for Jointly Operated Systems") Issue 18 for the November 1999 Jet A-1 (This specification incorporates the most stringent requirements of ASTM Specification D 1655 and 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 compound or compounds of formula (I) are added to the conventional aviation 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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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Liquid Carbonaceous Fuels (AREA)
EP14178407.4A 2014-07-24 2014-07-24 Zyklische Acetalderivate als Antirußzusätze für einen Flugzeug-Treibstoff Ceased EP2977433A1 (de)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP14178407.4A EP2977433A1 (de) 2014-07-24 2014-07-24 Zyklische Acetalderivate als Antirußzusätze für einen Flugzeug-Treibstoff
PCT/EP2015/066305 WO2016012345A1 (fr) 2014-07-24 2015-07-16 Dérivés acétals cycliques à titre d'additifs anti-suies pour un carburant d'aviation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP14178407.4A EP2977433A1 (de) 2014-07-24 2014-07-24 Zyklische Acetalderivate als Antirußzusätze für einen Flugzeug-Treibstoff

Publications (1)

Publication Number Publication Date
EP2977433A1 true EP2977433A1 (de) 2016-01-27

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EP14178407.4A Ceased EP2977433A1 (de) 2014-07-24 2014-07-24 Zyklische Acetalderivate als Antirußzusätze für einen Flugzeug-Treibstoff

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WO (1) WO2016012345A1 (de)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017006142A1 (en) * 2015-07-06 2017-01-12 Rodhia Poliamida E Especialidades Ltda Gasoline compositions with improved octane number

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3594136A (en) 1968-11-26 1971-07-20 Cities Service Oil Co Smoke suppressant additives
GB1246853A (en) 1968-01-02 1971-09-22 Cities Service Oil Co Ethers as smoke suppressants
US6458176B2 (en) * 1999-12-21 2002-10-01 Exxonmobil Research And Engineering Company Diesel fuel composition
EP1321502A1 (de) * 2001-12-19 2003-06-25 Institut Francais Du Petrole Glycerolacetale enthaltende Dieselkraftstoffzusammensetzungen
EP1321503A1 (de) 2001-12-19 2003-06-25 Institut Francais Du Petrole Glycerolacetalcarbonate enthaltende Dieselkraftstoffzusammensetzungen
US20100005707A1 (en) 2008-07-09 2010-01-14 Eberhard Jacob Low-soot diesel fuels comprising a fuel additive, use thereof and the use of the fuel additive for producing low-soot diesel fuels
US20110131871A1 (en) 2009-07-31 2011-06-09 Man Nutzfahrzeuge Ag Use of polyoxymethylene di (alkyl polyglycol) ethers as additives to diesel fuels to reduce the particulate emission in self-ignition engines

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1246853A (en) 1968-01-02 1971-09-22 Cities Service Oil Co Ethers as smoke suppressants
US3594136A (en) 1968-11-26 1971-07-20 Cities Service Oil Co Smoke suppressant additives
US6458176B2 (en) * 1999-12-21 2002-10-01 Exxonmobil Research And Engineering Company Diesel fuel composition
EP1321502A1 (de) * 2001-12-19 2003-06-25 Institut Francais Du Petrole Glycerolacetale enthaltende Dieselkraftstoffzusammensetzungen
EP1321503A1 (de) 2001-12-19 2003-06-25 Institut Francais Du Petrole Glycerolacetalcarbonate enthaltende Dieselkraftstoffzusammensetzungen
US20100005707A1 (en) 2008-07-09 2010-01-14 Eberhard Jacob Low-soot diesel fuels comprising a fuel additive, use thereof and the use of the fuel additive for producing low-soot diesel fuels
US20110131871A1 (en) 2009-07-31 2011-06-09 Man Nutzfahrzeuge Ag Use of polyoxymethylene di (alkyl polyglycol) ethers as additives to diesel fuels to reduce the particulate emission in self-ignition engines

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
"Kerosene/Jet fuel category assessment document", 21 September 2010, AMERICAN PETROLEUM INSTITUTE
CHEUNG ET AL.: "Performance of diesel engine using diesel fuel blended with dimethyl carbonate", SOUTHEAST UNIVERSITY PRESS
GUO ET AL.: "Development of di(2-ethoxyethyl)carbonate as a clean diesel fuel additive", 2006, AMERICAN CHEMICAL SOCIETY, pages: 270943
GUO ET AL.: "Development of di(2-ethoxyethyl)carbonate used as a clean diesel fuel additive", vol. 2006, AMERICAN CHEMICAL SOCIETY, pages: 249481
GUO ET AL.: "Investigation of a novel oxygenate, methyl 2-ethoxyethyl carbonate, as a clean diesel fuel additive", 2005, AMERICAN CHEMICAL SOCIETY, pages: 190024
ROUNCE ET AL.: "Comparison of Diesel and Biodiesel Emissions Using Dimethyl Carbonate as an Oxygenated Additive", UK. ENERGY & FUELS, vol. 24, no. 9, 2010, pages 4812 - 4819
STEVE HANSEN: "Diesel Emerging As New Technology of Choice for General Aviation | Diesel Technology Forum", 26 July 2012 (2012-07-26), XP055151051, Retrieved from the Internet <URL:http://www.dieselforum.org/news/diesel-emerging-as-new-technology-of-choice-for-general-aviation> [retrieved on 20141105] *

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