EP0923628B1 - Sauerstoffenthaltende produkte als dieselbrennstoff - Google Patents

Sauerstoffenthaltende produkte als dieselbrennstoff 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
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Prior art keywords
carbon atoms
fuel composition
composition according
formula
atoms
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EP98929517A
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French (fr)
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EP0923628A1 (de
Inventor
Laurent Germanaud
Paul Maldonado
Paul Bourdauducq
Jean-Luc Couturier
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TotalEnergies Marketing Services SA
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TotalFinaElf France SA
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    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
    • C10L1/026—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/198—Macromolecular 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
    • C10L1/1985—Macromolecular 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

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  • 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)

Claims (15)

  1. Kraftstoffzusammensetzung mit 60 bis 99,95 Gewichtsprozent wenigstens eines Grundkraftstoffs und mit 0,05 bis 40 Gewichtsprozent wenigstens eines Trialkoxyalkans der nachstehenden allgemeinen Formel (I):
    Figure 00130001
    in der:
    X einer zweiwertigen Kohlenwasserstoffgruppe CnH2n entspricht, mit n gleich 1, 2 oder 3, wobei jedes Wasserstoffatom eventuell durch einen Kohlenwasserstoffrest ersetzt ist;
    R1, R'1 und R"1 lineare oder verzweigte Alkylgruppen sind, die gleich oder unterschiedlich sind, mit 1 bis 10 Kohlenstoffatomen und eventuell wenigstens einem Sauerstoffatom, wobei zwei der Gruppen R1, R'1 und R"1 eventuell verbunden sind, um eine heterozyklische Verbindung von 5 bis 6 Atomen zu bilden; und
    R2 ein Wasserstoffatom oder ein lineares Alkylradikal mit 1 bis 4 Kohlenstoffatomen ist, wobei R2 durch Verbindung mit einem Kohlenwasserstoffrest von X selbst einen Ring mit 5 bis 6 Kohlenstoffatomen bilden kann.
  2. Kraftstoffzusammensetzung nach Anspruch 1, dadurch gekennzeichnet, dass der Trialkoxyalkan aus den Trialkoxypropanen der nachstehenden Formel (II) gewählt ist:
    Figure 00130002
    in der:
    R1, R'1 und R"1 lineare oder verzweigte Alkylgruppen sind, die gleich oder unterschiedlich sind, mit 1 bis 10 Kohlenstoffatomen und eventuell wenigstens einem Sauerstoffatom, wobei zwei der Gruppen R1, R'1 und R"1 eventuell verbunden sind, um eine heterozyklische Verbindung von 5 bis 6 Atomen zu bilden;
    R2, R3, R4 und R'4 gleiche oder unterschiedliche Gruppen sind, die Wasserstoff oder ein lineares Alkylradikal mit 1 bis 4 Kohlenstoffatomen darstellen, wobei R2 durch Verbindung mit R4 oder R'4 selbst einen Ring mit 5 bis 6 Kohlenstoffatomen bilden kann.
  3. Kraftstoffzusammensetzung nach Anspruch 2, dadurch gekennzeichnet, dass R2, R3, R4 und R'4 in der Formel (II) einem Wasserstoffatom entsprechen.
  4. Kraftstoffzusammensetzung nach einem der Ansprüche 2 und 3, dadurch gekennzeichnet, dass R1, R'1 und R"1 gleich sind und aus Alkylgruppen mit 1 bis 4 Kohlenstoffatomen gewählt sind.
  5. Kraftstoffzusammensetzung nach den Ansprüchen 2 bis 4, dadurch gekennzeichnet, dass die Verbindungen nach Formel (II) aus der Gruppe gewählt sind, die aus Trimethoxypropan, Triethoxypropan, Tripropoxypropan, Tributoxypropan besteht.
  6. Kraftstoffzusammensetzung nach den Ansprüchen 2 und 3, dadurch gekennzeichnet, dass R1, R'1 und R"1 1 bis 4 Kohlenstoffatome und wenigstens ein Sauerstoffatom enthalten.
  7. Kraftstoffzusammensetzung nach den Ansprüchen 2, 3 und 6, dadurch gekennzeichnet, dass die Verbindungen nach Formel (II) aus der Gruppe gewählt sind, die aus Tri(methoxyethoxy)propan und Tri(ethoxyethoxy)propan besteht.
  8. Kraftstoffzusammensetzung nach den Ansprüchen 2 und 3, dadurch gekennzeichnet, dass R1 eine Alkylgruppe mit 1 bis 4 Kohlenstoffatomen ist und R'1 und R"1 verbunden sind und einen Kettenabschnitt aus 2 bis 3 Kohlenstoffatomen bilden, so dass sie mit den zwei Sauerstoffatomen eine heterozyklische Verbindung aus 5 bis 6 Atomen bilden.
  9. Kraftstoffzusammensetzung nach den Ansprüchen 2, 3 und 8, dadurch gekennzeichnet, dass die Verbindung nach Formel (II) 2-(2-Hydroxyethyl)ethoxy-1,3-dioxolan ist.
  10. Kraftstoffzusammensetzung nach Anspruch 2, dadurch gekennzeichnet, dass in der Formel (II) R4 eine Alkylgruppe mit 1 bis 4 Kohlenstoffatomen ist und R2, R3 und R'4 Wasserstoffatome sind und R1, R'1 und R"1 Alkylgruppen mit 1 bis 5 Kohlenstoffatomen sind.
  11. Kraftstoffzusammensetzung nach den Ansprüchen 2 und 10, dadurch gekennzeichnet, dass die Verbindungen nach Formel (II) aus der Gruppe gewählt sind, die aus 1,1,3-Trimethoxybutan, 1,1,3-Triethoxybutan, 1,1,3-Tripropoxybutan und 1,1,3-Tributoxybutan besteht.
  12. Kraftstoffzusammensetzung nach Anspruch 2, dadurch gekennzeichnet, dass in der Formel (II) R2 oder R3 eine Alkylgruppe mit 1 bis 4 Kohlenstoffatomen ist, R4, R'4 und R2 oder R3 Wasserstoffatome sind und R1, R'1 und R"1 Alkylgruppen mit 1 bis 5 Kohlenstoffatomen sind.
  13. Kraftstoffzusammensetzung nach den Ansprüchen 2 und 12, dadurch gekennzeichnet, dass die Verbindungen nach Formel (II) aus der Gruppe gewählt sind, die aus 1,1,3-Triethoxy-2-methylpropan und 1,3,3-Triethoxybutan besteht.
  14. Kraftstoffzusammensetzung nach Anspruch 2, dadurch gekennzeichnet, dass in der Formel (II) R3 und R4 Wasserstoffatome sind, R2 und R'4 verbunden sind, um einen gesättigten Ring mit 5 bis 6 Kohlenstoffatomen zu bilden, und R1, R'1 und R"1 Alkylgruppen mit 1 bis 5 Kohlenstoffatomen sind.
  15. Kraftstoffzusammensetzung nach den Ansprüchen 2 und 14, dadurch gekennzeichnet, dass die Verbindung nach Formel (II) 1,1,3-Triethoxycyclohexan ist.
EP98929517A 1997-06-09 1998-06-08 Sauerstoffenthaltende produkte als dieselbrennstoff Expired - Lifetime EP0923628B1 (de)

Applications Claiming Priority (3)

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

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EP0923628A1 EP0923628A1 (de) 1999-06-23
EP0923628B1 true EP0923628B1 (de) 2003-01-15

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

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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
ATE376044T1 (de) * 2001-09-18 2007-11-15 Southwest Res Inst Brennstoffe für homogen geladene verdichtungsgezündete maschinen
FR2833607B1 (fr) * 2001-12-19 2005-02-04 Inst Francais Du Petrole Compositions de carburants diesel contenant des acetals de glycerol
ATE455834T1 (de) * 2003-06-24 2010-02-15 Biovalue Holding Bv Verwendung eines oxygenates als additiv zur verringerung der partikelemission in kraftstoffen,insbesondere in dieselkraftstoffen, ottokraftstoffen und rapsmethylester
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
JP5462258B2 (ja) * 2008-07-16 2014-04-02 ハー・マジェスティ・ザ・クイーン・イン・ライト・オブ・カナダ・アズ・リプリゼンテッド・バイ・ザ・ミニスター・オブ・ナチュラル・リソーシーズ・カナダ グリセロールの、ナフサの範囲の酸素化物への転換
DE102009055928A1 (de) * 2009-11-27 2011-06-01 Technische Universität Dortmund Verfahren zur kontinuierlichen Herstellung von Glycerintertiärbutylethern
EP2585562A1 (de) 2010-06-22 2013-05-01 Shell Internationale Research Maatschappij B.V. Formulierung für dieselkraftstoffe
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
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US9303228B2 (en) 2014-05-15 2016-04-05 Seachange Group Llc Biodiesel glycerol emulsion fuel mixtures
CN114958451B (zh) * 2022-06-15 2023-03-28 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

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

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