EP1321503B1 - Glycerolacetalcarbonate enthaltende Dieselkraftstoffzusammensetzungen - Google Patents

Glycerolacetalcarbonate enthaltende Dieselkraftstoffzusammensetzungen Download PDF

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Publication number
EP1321503B1
EP1321503B1 EP02292949A EP02292949A EP1321503B1 EP 1321503 B1 EP1321503 B1 EP 1321503B1 EP 02292949 A EP02292949 A EP 02292949A EP 02292949 A EP02292949 A EP 02292949A EP 1321503 B1 EP1321503 B1 EP 1321503B1
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EP
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Prior art keywords
diesel fuel
glycerol acetal
fuel composition
radical
composition according
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English (en)
French (fr)
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EP1321503A1 (de
Inventor
Bruno Delfort
Isabelle Durand
Anne Jaecker
Thierry Lacome
Xavier Montagne
Fabrice Paille
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IFP Energies Nouvelles IFPEN
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IFP Energies Nouvelles IFPEN
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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
    • C10L1/19—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
    • 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, 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
    • C10L10/02—Use of additives to fuels or fires for particular purposes for reducing smoke development

Definitions

  • the invention relates to diesel fuel compositions containing oxygenated compounds consisting of glycerol acetal carbonates.
  • US Patent 4891049 discloses a diesel fuel comprising an additive based on alkyl carbonate.
  • R 1 and R 2 are each a hydrogen atom, a methyl, ethyl or propyl radical and R 3 is a methyl or ethyl radical.
  • R 1 and R 2 are each a hydrogen atom, a methyl, ethyl or propyl radical and R 3 is a methyl or ethyl radical.
  • the sum of the number of carbon atoms of R1, R2 and R3 is at least 2.
  • This reaction is generally carried out in a basic medium with a catalyst selected for example from hydroxides, carbonates, alkoxides and hydrides of alkali or alkaline earth metals or other metals.
  • a catalyst selected for example from hydroxides, carbonates, alkoxides and hydrides of alkali or alkaline earth metals or other metals.
  • This reaction can also be carried out by condensation of a urethane of general formula R 3 -CO-NH 2 on the free hydroxyl function of the glycerol acetals with release of ammonia, the urethane R 3 -CO-NH 2 which can itself be obtained easily by condensation of the alcohol R3-OH with urea.
  • the glycerol acetals are themselves prepared most often by reaction, generally in an acid medium of an aldehyde or a ketone on glycerol or by transacetalization reaction. These reactions, applied to an R-OH alcohol, are represented by the diagrams below: 2 R-OH + R'CHO ⁇ (RO) 2CH-R '+ H2O (3) 2 R-OH + (R "O) 2CH-R ' ⁇ (RO) 2CH-R' + 2R" OH (4)
  • the products used in the invention may consist of one or more compounds corresponding to the general formulas (1) and (2).
  • the diesel fuel in question may be of petroleum origin or a mixture of alkyl esters derived from vegetable oils.
  • the diesel fuel compositions of the invention may contain glycerol acetals in various proportions.
  • the glycerol acetal carbonate or each of the glycerol acetal carbonates will be introduced into the diesel fuel at a concentration such that it is soluble in said diesel fuel.
  • proportions of 1 to 40% by volume, usually 1 to 20% by volume, are used.
  • diesel fuel compositions of the invention are generally free of Group IIA metal compounds of the Periodic Table of Elements.
  • Example 1 the synthesis of glycerol acetal carbonates is described.
  • Example 3 describes tests for evaluating the performance of gas oil compositions closing the glycerol acetal carbonates prepared in Examples 1 and 2.
  • Example 1 is repeated replacing n-butyraldehyde with an equimolar amount of acetone.
  • the product of the reaction corresponds mainly to the following formula:
  • the particulate emissions measured with these fuels will be compared with those obtained with diesel alone.
  • the tests were conducted on a diesel vehicle equipped with a direct injection engine.
  • cycle MVEG-11s Euro 2000 The test results, expressed in gram of particles per kilometer, are presented on each phase of the cycle and on the complete cycle.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Combustion & Propulsion (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)

Claims (7)

  1. Dieselkraftstoffzussmmensetzung, dadurch gekennzeichnet, dass sie einen überwiegenden Anteil mindestens eines Dieselkraftstoffs und mindestens ein Glycerolacetelcarbonat umfasst, das einer dar folgenden allgemeinen Formeln entspricht:
    Figure imgb0014
     worin:
    - R1 und R2 jeweils für ein Wasserstoffatom, einen aliphatischen Kohlenwassarstoffrest mit 1 bis 20 Kohlenstoffatomen stehen,
    - R3 ein Rast ist, definiert wie R1 oder R2, abgesehen vorn Wasserstoffatom, oder ein Rest mit der folgenden allgemeinen Formel:
    Figure imgb0015
     worin R1 und R2 sind, wie oben definiert.
  2. Dieselkraftstoffzusammensetzung nach Anspruch 1, dadurch gekennzeichnet, dass in der Formel für das Glycerolacetalcarbonat R1 und R2 jeweils ein Wasserstoffatom, ein Methyl-, Ethyl- oder Propylrest und R3 ein Methyl- oder Ethylrest ist.
  3. Dieselkraftstoffzusammensetzung nach Anspruch 1 oder 2, dadurch gekennzeichnet, dass die Summe der Anzahl an Kohlenstoffatomen von R1, R2 und R3 mindestens 2 ist.
  4. Dieselkraftstoffzusammensetzung nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass sie einen Dieselkraftstoff und einen Anteil von 1 bis 40 Vat.-% mindestens eines Glycerolacetalcarbonats umfasst.
  5. Dleselkraftstoffzusammensetzung nach Anspruch 4, dadurch gekennzeichnet, dass der Anteil an Glycerolacetalcarbonat 1 bis; 20 Vol.-% beträgt.
  6. Diesalkraffstoffzusammensetzung nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass der Dieselkraftstoff einen Diessekraftstoff umfasst, der aus Erdöl hergestellt ist.
  7. Dieselkratfstoffzusammensetzung nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass der Dieselkraftstoff ein Gemisch aus Alkylestern umfasst, die von Pflanzenölen abgeleitet sind.
EP02292949A 2001-12-19 2002-11-29 Glycerolacetalcarbonate enthaltende Dieselkraftstoffzusammensetzungen Expired - Lifetime EP1321503B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0116448A FR2833606B1 (fr) 2001-12-19 2001-12-19 Compositions de carburants diesel contenant des carbonates d'acetals de glycerol
FR0116448 2001-12-19

Publications (2)

Publication Number Publication Date
EP1321503A1 EP1321503A1 (de) 2003-06-25
EP1321503B1 true EP1321503B1 (de) 2010-11-24

Family

ID=8870683

Family Applications (1)

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EP02292949A Expired - Lifetime EP1321503B1 (de) 2001-12-19 2002-11-29 Glycerolacetalcarbonate enthaltende Dieselkraftstoffzusammensetzungen

Country Status (6)

Country Link
US (1) US7097674B2 (de)
EP (1) EP1321503B1 (de)
AT (1) ATE489448T1 (de)
DE (1) DE60238380D1 (de)
ES (1) ES2354413T3 (de)
FR (1) FR2833606B1 (de)

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WO2006093896A1 (en) * 2005-03-01 2006-09-08 Michigan State University Process for production of a composition useful as a fuel
KR101344770B1 (ko) * 2006-07-12 2013-12-24 인스티투트 우니브. 데 치엔치아 아이 테크놀로지아, 에쎄.아. 글리세롤 포르말의 지방산 에스테르의 제조 방법 및 바이오연료로서의 이의 용도
WO2008013844A2 (en) * 2006-07-25 2008-01-31 General Vortex Energy, Inc. System, apparatus and method for combustion of metal and other fuels
FR2905703A1 (fr) * 2006-09-13 2008-03-14 Arkema France Compositions de carburants diesel contenant des esters d'acetals de glycerol
WO2009145674A1 (ru) 2008-05-28 2009-12-03 Учреждение Российской Академии Наук Институт Биохимической Физики Им. Н.М. Эмануэля Ран (Ибхф Ран) Средство для повышения октанового числа бензинового автомобильного топлива
US20100094027A1 (en) * 2008-08-20 2010-04-15 Todd Coleman Process for the Preparation of Glycerol Formal
US8663346B2 (en) 2009-11-24 2014-03-04 Shell Oil Company Fuel formulations
US20110162261A1 (en) * 2009-11-24 2011-07-07 Caroline Nicola Orlebar Fuel formulations
US8557001B2 (en) * 2009-11-24 2013-10-15 Shell Oil Company Fuel formulations
EP2409695B1 (de) 2010-07-05 2018-03-21 Beth Israel Deaconess Medical Center, Inc. Sn-2-monoacylglycerine und fett-malabsorption
EP2730567A1 (de) 2012-11-09 2014-05-14 Institut Univ. de Ciència i Tecnologia, S.A. Verfahren zur Herstellung von Biokraftstoffen
EP2757140A1 (de) 2013-01-17 2014-07-23 Institut Univ. de Ciència i Tecnologia, S.A. Formulierung, Herstellung und Verwendung eines glycerinbasierten Kraftstoffs
BR112015023720B1 (pt) 2013-03-15 2021-06-15 Hexion Inc Resina de amino-formaldeído, processo para preparação de uma resina de amino- formaldeído, e, artigo de fabricação
EP2977433A1 (de) 2014-07-24 2016-01-27 Rhodia Opérations Zyklische Acetalderivate als Antirußzusätze für einen Flugzeug-Treibstoff
EP2977435A1 (de) 2014-07-24 2016-01-27 Rhodia Opérations Zyklische Karbonatderivate als Antirußzusätze für einen Treibstoff
EP2977434A1 (de) 2014-07-24 2016-01-27 Rhodia Opérations Polyoxigenierte Verbindungen als Antirußzusätze für einen Treibstoff
US9574152B2 (en) * 2015-02-19 2017-02-21 Hexion Inc. Diesel fuel additive

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Publication number Priority date Publication date Assignee Title
US3036904A (en) * 1959-09-21 1962-05-29 Texaco Inc Motor fuel containing octane appreciator
GB1196610A (en) * 1966-10-11 1970-07-01 Lummus Co Purification of Gases
US3755171A (en) * 1971-06-18 1973-08-28 Universal Oil Prod Co Lubricant additive mixture
US4891049A (en) * 1985-12-20 1990-01-02 Union Oil Company Of California Hydrocarbon fuel composition containing carbonate additive
US5268007A (en) * 1986-12-29 1993-12-07 The Lubrizol Corporation Dioxolanes and thio analogs, derivatives thereof and lubricants and fuels containing same
US4904279A (en) * 1988-01-13 1990-02-27 Union Oil Company Of California Hydrocarbon fuel composition containing carbonate additive
CA2033462C (en) * 1990-12-31 1996-06-18 Sheldon Robar Engine system using refrigerant fluid
JP3003015B2 (ja) * 1992-08-11 2000-01-24 花王株式会社 冷凍機作動流体用組成物
CA2180617A1 (en) * 1995-07-07 1997-01-08 Barton White Explosive or fertiliser composition
US6172031B1 (en) * 1997-10-17 2001-01-09 Edwin Stevens Compositions and methods for use in cleaning textiles

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Publication number Publication date
ATE489448T1 (de) 2010-12-15
ES2354413T3 (es) 2011-03-14
DE60238380D1 (de) 2011-01-05
FR2833606B1 (fr) 2004-02-13
US7097674B2 (en) 2006-08-29
US20040025417A1 (en) 2004-02-12
FR2833606A1 (fr) 2003-06-20
EP1321503A1 (de) 2003-06-25

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