EP0923628B1 - Composition de carburant comprenant des composes oxygenes pour moteurs diesel - Google Patents

Composition de carburant comprenant des composes oxygenes pour moteurs diesel Download PDF

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Publication number
EP0923628B1
EP0923628B1 EP98929517A EP98929517A EP0923628B1 EP 0923628 B1 EP0923628 B1 EP 0923628B1 EP 98929517 A EP98929517 A EP 98929517A EP 98929517 A EP98929517 A EP 98929517A EP 0923628 B1 EP0923628 B1 EP 0923628B1
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
fuel composition
composition according
formula
atoms
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.)
Expired - Lifetime
Application number
EP98929517A
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German (de)
English (en)
French (fr)
Other versions
EP0923628A1 (fr
Inventor
Laurent Germanaud
Paul Maldonado
Paul Bourdauducq
Jean-Luc Couturier
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
TotalEnergies Marketing Services SA
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TotalFinaElf France SA
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Publication date
Application filed by TotalFinaElf France SA filed Critical TotalFinaElf France SA
Publication of EP0923628A1 publication Critical patent/EP0923628A1/fr
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Anticipated expiration legal-status Critical
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Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/185Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852Ethers; Acetals; Ketals; Orthoesters
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/02Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
    • C10L1/026Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for compression ignition
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/185Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852Ethers; Acetals; Ketals; Orthoesters
    • C10L1/1855Cyclic ethers, e.g. epoxides, lactides, lactones
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/192Macromolecular compounds
    • C10L1/198Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
    • C10L1/1985Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters

Definitions

  • the present invention relates to a new fuel composition
  • a new fuel composition comprising oxygenated compounds improving fuel combustion, especially compounds that can improve the cetane number of bases fuels such as middle distillates used in the composition of diesel for diesel engines.
  • a fuel base generally consists of a physical mixture of several middle or cut distillates petroleum products from the refining of crude oils from from all walks of the world. These oil cuts are from a large number of separations by distillation atmospheric or vacuum and chemical transformations of some of these cuts distilled by hydrodesulfurization and or catalytic cracking. By an appropriate mixture of these different refined cuts, we get a wide variety fuel bases with physico-chemical properties relatively different. Finally, diesel fuels or diesel fuels usable in combustion engines are prepared by a complex mixture of these bases. However, to obtain fuels meeting the specifications legal requirements, refiners must develop increasingly complicated formulations which favor crude oils highly concentrated in distillates and fuel bases with a high cetane number.
  • additives i.e. the compounds introduced at low levels in refined cuts
  • nitrates or peroxides organic which are known to have limited effectiveness in fuel bases or diesel fuel with naturally a low cetane number.
  • organic peroxides are irreversibly broken down into function of time which leads to a degradation of characteristics of diesel stored both in quality and in cetane number.
  • Refiners have long sought others sources of compounds that can improve the index of cetane from fuel bases and gas oils, in particular among oxygenated compounds such as ethers, polyethers or acetals. Addition of compounds oxygenated in diesel, reduces emissions of pollutants, in particular particle emissions (EP 14 992).
  • US patent 5308365 claims the addition of 1 to 30% by weight of dialkylated and trialkylated derivatives of glycerin, obtained by adding an olefin such as isobutene on glycerol, in a diesel having a range of use between 160 ° C and 370 ° C and a sulfur content less than or equal to 500 ppm.
  • Patent JP 0725 8661 claims a formulation comprising 20 to 94% of a diesel cut having a distillation range between 130 ° C and 400 ° C, 5 to 40% of a hydrocracked diesel cut commonly called LCO and 1 to 40 % of a monoether of formula R 1 OR 2 in which R 1 and R 2 are alkyl chains of 3 to 12 carbon atoms.
  • Patent JP 0701 8271 claims gas oils containing glycol ethers of formula R 1 - (OA) n -R 2 in which R 1 is an alkyl chain of 1 to 10 carbon atoms, R 2 represents the hydrogen atom or an alkyl chain comprising from 1 to 10 carbon atoms, A is of ethylene or trimethylene structure optionally substituted and n is an integer varying from 1 to 10.
  • Patent JP 0634 0886 claims the addition to a diesel of 0.05% to 20% by weight of a compound of general formula R 1 -O- (EO) n - (PO) m -R 2 in which R 1 and R 2 represent separately the hydrogen atom or an alkyl chain comprising from 1 to 20 carbon atoms, EO and PO respectively representing the oxyethylene and oxyisopropylene groups, and, m and n are whole numbers between 0 and 15.
  • patent FR 2,544,738 claims, as a component of diesel fuels, acetals of formula C 4 H 9 -O-CR 1 R 2 -OC 4 H 9 , R 1 and R 2 which may be hydrogen or one, alkyl group.
  • the present invention relates to the use of a new family of oxygenated compounds in fuels Diesel, which increase the cetane number, provide greater flexibility in the formulation of Diesel fuels for a lower cost and allow in besides limiting aromatic and sulfur compounds responsible for the emission of particles.
  • this fuel composition contains 60 to 99.95% by weight at least one fuel base and from 0.05 to 40% by weight of trialkoxyalkane of formula (I).
  • fuel base any petroleum cut after refining, either by distillation or by treatment of these distilled cups.
  • R 2 , R 3 , R 4 and R ' 4 are the hydrogen atom.
  • R 1 , R ' 1 and R'' 1 are identical and are chosen from alkyl groups comprising from 1 to 4 carbon atoms.
  • trialkoxyalkane compounds thus obtained from the invention are chosen from the group consisting of trimethoxypropane, triethoxypropane, tripropoxypropane, tributoxypropane.
  • R 1 , R ' 1 and R'' 1 comprise from 1 to 4 carbons and at least one oxygen atom.
  • R 1 is an alkyl group comprising from 1 to 4 carbon atoms and R ' 1 and R'' 1 are linked and constitute a chain of 2 to 3 carbons so as to form with the two oxygen atoms a heterocycle of 5 to 6 atoms.
  • R ' 1 and R'' 1 are linked and constitute a chain of 2 to 3 carbons so as to form with the two oxygen atoms a heterocycle of 5 to 6 atoms.
  • 2- (2-hydroxyethyl) ethoxy-1,3-dioxolane is preferred.
  • R 4 is an alkyl group of 1 to 4 carbon atoms
  • R 2 , R 3 and R ' 4 are hydrogen atoms
  • R 1 , R ' 1 and R''1 are alkyl groups comprising from 1 to 5 carbon atoms.
  • R 2 or R 3 is an alkyl group comprising 1 to 4 carbon atoms
  • R 4 , R ' 4 and, R 2 or R 3 are atoms of hydrogen
  • R 1 , R ' 1 and R'' 1 are alkyl groups comprising from 1 to 5 carbon atoms.
  • the 1,1,3-triethoxy-2-methylpropane and 1,3,3-triethoxybutane are preferred.
  • R 3 and R 4 are hydrogen atoms
  • R 2 and R ' 4 are linked to form a saturated ring comprising from 5 to 6 atoms carbon
  • R 1 , R ' 1 and R'' 1 are alkyl groups comprising from 1 to 5 carbon atoms.
  • 1,1,3-triethoxycyclohexane is preferred.
  • the basics fuels are chosen from refined cuts distilling between 170 and 370 ° C containing at most 50% by weight aromatics, and less than 0.2% by weight of compounds sulfur.
  • the cetane number of 1,1,3-triethoxypropane prepared according to example 1 was measured according to standard ASTM D613, in a 20% mixture in two gas oils whose characteristics are indicated below:
  • a compound having a cetane number higher than 70, and a boiling point of at least 160 ° C and a very low solubility in water can be considered as an ideal component usable in a diesel.
  • Ethylene ether glycol 135 miscible 38 Ethyl, ethylene glycol butyl ether 140 # 4 51 Diethylene glycol ethyl ether 202 miscible 54

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)
EP98929517A 1997-06-09 1998-06-08 Composition de carburant comprenant des composes oxygenes pour moteurs diesel Expired - Lifetime EP0923628B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9707119A FR2764301B1 (fr) 1997-06-09 1997-06-09 Composition de carburant comprenant des composes oxygenes pour moteurs diesel
FR9707119 1997-06-09
PCT/FR1998/001168 WO1998056879A1 (fr) 1997-06-09 1998-06-08 Composition de carburant comprenant des composes oxygenes pour moteurs diesel

Publications (2)

Publication Number Publication Date
EP0923628A1 EP0923628A1 (fr) 1999-06-23
EP0923628B1 true EP0923628B1 (fr) 2003-01-15

Family

ID=9507765

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98929517A Expired - Lifetime EP0923628B1 (fr) 1997-06-09 1998-06-08 Composition de carburant comprenant des composes oxygenes pour moteurs diesel

Country Status (10)

Country Link
US (1) US6113661A (da)
EP (1) EP0923628B1 (da)
JP (1) JP2000516991A (da)
AT (1) ATE231179T1 (da)
DE (1) DE69810746T2 (da)
DK (1) DK0923628T3 (da)
ES (1) ES2189188T3 (da)
FR (1) FR2764301B1 (da)
NO (1) NO990578L (da)
WO (1) WO1998056879A1 (da)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2764301B1 (fr) * 1997-06-09 1999-07-30 Elf Antar France Composition de carburant comprenant des composes oxygenes pour moteurs diesel
US6843813B1 (en) * 2000-06-07 2005-01-18 Hugh Frederick Collins Rejuvenation and/or cleaning of catalysts
GB2368594A (en) * 2000-08-17 2002-05-08 Shell Int Research Fuel compositions with reduced soot emissions
US6514299B1 (en) * 2000-11-09 2003-02-04 Millennium Fuels Usa, Llc Fuel additive and method therefor
WO2003025100A2 (en) * 2001-09-18 2003-03-27 Southwest Research Institute Fuels for homogeneous charge compression ignition engines
FR2833607B1 (fr) * 2001-12-19 2005-02-04 Inst Francais Du Petrole Compositions de carburants diesel contenant des acetals de glycerol
BRPI0411849A (pt) * 2003-06-24 2006-08-08 Michiel Arjaan Kousemaker processo para a fabricação de um composto contendo oxigênio como aditivo em combustìveis, em particular, em combustìveis a diesel, gasolina e ester metìlico de colza
US20090090048A1 (en) * 2007-10-05 2009-04-09 Board Of Trustees Of Michigan State University Fuel compositions with mono- or di- butyl succinate and method of use thereof
CA2729659C (en) * 2008-07-16 2015-11-24 Michio Ikura Conversion of glycerol to naphtha-range oxygenates
DE102009055928A1 (de) * 2009-11-27 2011-06-01 Technische Universität Dortmund Verfahren zur kontinuierlichen Herstellung von Glycerintertiärbutylethern
AU2011269085B2 (en) * 2010-06-22 2014-09-18 Shell Internationale Research Maatschappij B.V. Diesel fuel formulation
EP2514804A1 (de) * 2011-04-19 2012-10-24 Top-Biofuel GmbH & Co. KG Verwendung von 1,1-Dialkoxyalkanen zur Erhöhung der Klopffestigkeit von Motorenbenzin
US8679202B2 (en) 2011-05-27 2014-03-25 Seachange Group Llc Glycerol containing fuel mixture for direct injection engines
FI20110300A0 (fi) 2011-09-11 2011-09-11 Neste Oil Oyj Bensiinikoostumukset ja menetelmä niiden valmistamiseksi
CA2948363C (en) 2014-05-15 2024-01-02 Seachange Group Llc Biodiesel glycerol emulsion fuel mixtures
CN116536091A (zh) * 2022-06-15 2023-08-04 浙江吉利控股集团有限公司 一种汽油甲醇灵活燃料互溶防腐剂

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR868233A (fr) * 1940-12-20 1941-12-24 Carburants pour moteurs à combustion interne à injection
US2842432A (en) * 1953-12-07 1958-07-08 Texas Co Supplementary fuel mixture for cold starting diesel engines
US2897068A (en) * 1955-07-21 1959-07-28 Gulf Research Development Co Motor fuel
BR8000889A (pt) * 1979-02-21 1980-10-21 Basf Ag Composicoes carburantes para motores diesel
DE2911411C2 (de) * 1979-03-23 1983-10-20 Chemische Werke Hüls AG, 4370 Marl Verwendung vov 1,1-Di-n-ethoxiethan als Dieselkraftstoff
US4541837A (en) * 1979-12-11 1985-09-17 Aeci Limited Fuels
US4395267A (en) * 1980-03-26 1983-07-26 Texaco, Inc. Novel method of extending a hydrocarbon fuel heavier than gasoline
DE3231498A1 (de) * 1982-08-25 1984-03-01 Basf Ag, 6700 Ludwigshafen Verfahren zur herstellung von harten, bruchfesten katalysatoren aus zeolith-pulver
US5268008A (en) * 1982-12-27 1993-12-07 Union Oil Company Of California Hydrocarbon fuel composition
FR2544738B1 (fr) * 1983-04-21 1986-02-28 Inst Francais Du Petrole Nouveaux constituants de carburants pour moteurs automobile ou diesel
IT1177380B (it) * 1984-12-11 1987-08-26 Anic Spa Estensori di gasolio per autotrazione e loro metodo di produzione
US5262550A (en) * 1992-04-30 1993-11-16 Arco Chemical Technology, L.P. Epoxidation process using titanium-rich silicalite catalysts
JP3200149B2 (ja) * 1992-05-08 2001-08-20 三菱レイヨン株式会社 メタクリル酸合成用触媒の製造法
US5308365A (en) * 1993-08-31 1994-05-03 Arco Chemical Technology, L.P. Diesel fuel
FR2764301B1 (fr) * 1997-06-09 1999-07-30 Elf Antar France Composition de carburant comprenant des composes oxygenes pour moteurs diesel
US5746785A (en) * 1997-07-07 1998-05-05 Southwest Research Institute Diesel fuel having improved qualities and method of forming

Also Published As

Publication number Publication date
DK0923628T3 (da) 2003-05-05
EP0923628A1 (fr) 1999-06-23
FR2764301B1 (fr) 1999-07-30
NO990578L (no) 1999-04-06
FR2764301A1 (fr) 1998-12-11
DE69810746D1 (de) 2003-02-20
US6113661A (en) 2000-09-05
ES2189188T3 (es) 2003-07-01
NO990578D0 (no) 1999-02-08
DE69810746T2 (de) 2003-11-20
WO1998056879A1 (fr) 1998-12-17
JP2000516991A (ja) 2000-12-19
ATE231179T1 (de) 2003-02-15

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