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WO2007012585A1 - Compositions combustibles - Google Patents

Compositions combustibles Download PDF

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Publication number
WO2007012585A1
WO2007012585A1 PCT/EP2006/064396 EP2006064396W WO2007012585A1 WO 2007012585 A1 WO2007012585 A1 WO 2007012585A1 EP 2006064396 W EP2006064396 W EP 2006064396W WO 2007012585 A1 WO2007012585 A1 WO 2007012585A1
Authority
WO
WIPO (PCT)
Prior art keywords
levulinate
fuel
fuel composition
alkyl
additional components
Prior art date
Application number
PCT/EP2006/064396
Other languages
English (en)
Inventor
Johannes Pieter Haan
Jurgen Jacobus Johannes Louis
Paul Anthony Stevenson
Original Assignee
Shell Internationale Research Maatschappij B.V.
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
Application filed by Shell Internationale Research Maatschappij B.V. filed Critical Shell Internationale Research Maatschappij B.V.
Priority to EP06792524A priority Critical patent/EP1907513A1/fr
Priority to AU2006274057A priority patent/AU2006274057A1/en
Priority to CA002616080A priority patent/CA2616080A1/fr
Priority to BRPI0613897A priority patent/BRPI0613897A2/pt
Priority to JP2008523321A priority patent/JP2009503173A/ja
Publication of WO2007012585A1 publication Critical patent/WO2007012585A1/fr
Priority to NO20080958A priority patent/NO20080958L/no

Links

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
    • 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
    • C10L1/19Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • 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
    • C10L1/16Hydrocarbons
    • C10L1/1608Well defined compounds, e.g. hexane, benzene
    • 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
    • C10L1/16Hydrocarbons
    • C10L1/1616Hydrocarbons fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine

Definitions

  • the present invention relates to fuel compositions comprising a gas oil base fuel, particularly to such compositions containing a levulinate ester, and to their preparation and use.
  • diesel fuel components include the so-called “biofuels” which derive from biological materials. Examples include levulinate esters.
  • Levulinate esters esters of lev ⁇ linic acid
  • their preparation by reaction of the appropriate alcohol with furfuryl acetate are described in Zh. Prikl. Khim. (Leningrad) (1969) 42(4), 958-9, and in particular the methyl, ethyl, propyl, butyl, pentyl and hexyl esters.
  • WO-A-94/21753 discloses fuels for internal combustion engines, including both gasoline and diesel fuel, containing proportions (e.g. 1 to 90%v, 1 to 50%v, preferably 1 to 20%v) of esters of 04.-5 keto-carbonic acids, preferably levulinic acid, with C ⁇ -22 alcohols.
  • Esters with C]__8 alcohols are described as being particularly suitable for inclusion in gasolines, and esters with C9-.22 alcohols are described as being particularly suitable for inclusion in diesel fuels.
  • the temperature at which this occurs is termed the "Phase separation temperature”.
  • Diesel fuel specifications such as ASTM D975-02 (USA) and EN590 (Europe) include limits on Cloud Point temperature in order to ensure that diesel fuel remains fluid at the lowest anticipated service temperature and that blocking of fuel filters by wax is prevented.
  • any diesel fuel blend it is desirable for any diesel fuel blend to have an overall specification as close as possible to that of the standard commercially available diesel base fuels for which engines tend to be optimised.
  • the phase separation temperature of the fuel composition is dependent upon the level of aromatic constituents in the base fuel.
  • the phase separation temperature is lowered when the level of aromatic constituents is increased.
  • the amount of alkyl levulinate that can be incorporated in a homogeneous mixture is increased.
  • a fuel composition comprising a gas oil base fuel, an alkyl levulinate and one or more additional components, each of which components contains one or more aromatic constituents.
  • a method of reducing the phase separation temperature of a fuel composition comprising a gas oil base fuel and an alkyl levulinate, which method comprises increasing the level of aromatic constituents in the fuel composition, preferably by incorporating in the fuel composition one or more additional components, each of which components contains one or more aromatic constituents .
  • a fuel composition comprising a gas oil base fuel and an alkyl levulinate of one or more additional components, each of which components contains one or more aromatic constituents, for the purpose of reducing the phase separation temperature of the fuel composition
  • a method of operating a heating appliance provided with a burner comprises supplying to said burner a fuel composition according to the present invention.
  • a process for the preparation of a fuel composition which process involves blending a gas oil base fuel, an alkyl levulinate and one or more additional components, each of which components contains one or more aromatic constituents.
  • said alkyl levulinate is selected from C2-8 alkyl levulinates, more preferably ethyl levulinate, n-propyl levulinate, n-butyl levulinate, n-pentyl levulinate, 2-hexyl levulinate and 2-ethyl hexyl levulinate, still more preferably ethyl levulinate, n-butyl levulinate or n-pentyl levulinate, most preferably ethyl levulinate.
  • said additional components are selected from materials which are suitable to be blended with fuel compositions, such as for example (i) a refinery product stream with an aromatic content higher than that of the base fuel, or (ii) an aromatic solvent, e.g. SHELLSOL AB (available ex. Shell companies) , boiling in the normal temperature range of gas oil.
  • fuel compositions such as for example (i) a refinery product stream with an aromatic content higher than that of the base fuel, or (ii) an aromatic solvent, e.g. SHELLSOL AB (available ex. Shell companies) , boiling in the normal temperature range of gas oil.
  • the concentration of aromatic constituents in the fuel composition containing said additional component (s) accords with one or more of the following parameters :-
  • phase separation temperature of said fuel composition is reduced by at least 3°C, more preferably by at least 5°C, still more preferably by at least 1O 0 C, and most preferably by at least 2O 0 C.
  • said phase separation temperature of said fuel composition is below -5 0 C, more preferably below -10 0 C, still more preferably below -20°C, and most preferably below -30 0 C.
  • blends of two or more of the alkyl levulinates may be included in the fuel composition.
  • selection of the particular components of said blends and their proportions is dependent upon one or more desired characteristics of the fuel composition.
  • the present invention may be used tc formulate fuel blends which are expected to be of particular use in modern commercially available diesel engines as alternatives to the standard diesel base fuels, for instance as commercial and legislative pressures favour the use of increasing quantities of organically derived "biofuels".
  • a fuel component in a fuel composition means incorporating the component into the composition, typically as a blend (i.e. a physical mixture) with one or more other fuel components, conveniently before the composition is introduced into an engine.
  • the fuel composition will typically contain a major proportion of the base fuel, such as from 50 to 99%v, preferably from 50 to 98%v, more preferably from 80 to 98%v, most preferably from 90 to 98%v.
  • the proportions of the alkyl levulinates will be chosen to achieve the desired degree of miscibility, i.e. phase separation temperature, and may also be influenced by other properties required of the overall composition.
  • the fuel compositions to which the present invention relates include diesel fuels for use in automotive compression ignition engines, as well as in other types of engine such as for example marine, railroad and stationary engines, and industrial gas oils for use in heating applications (e.g. boilers).
  • the base fuel may itself comprise a mixture of two or more different diesel fuel components, and/or be additivated as described below.
  • Such diesel fuels will contain a base fuel which may typically comprise liquid hydrocarbon middle distillate gas oil(s), for instance petroleum derived gas oils.
  • a base fuel which may typically comprise liquid hydrocarbon middle distillate gas oil(s), for instance petroleum derived gas oils.
  • Such fuels will typically have boiling points within the usual diesel range of 150 to 400 0 C, depending on grade and use. They will typically have a density from 750 to
  • 900 kg/m 3 preferably from 800 to 860 kg/m 3 , at 15 0 C (e.g. ASTM D4502 or IP 365) and a cetane number (ASTM D613) of from 35 to 80, more preferably from 40 to 75. They will typically have an initial boiling point in the range 150 to 23O 0 C and a final boiling pc:.nt in the range 290 to 400 0 C. Their kinematic viscosity at 40°C (ASTM
  • D445) might suitably be from 1.5 to 4.5 rrm2/s.
  • Such industrial gas oils will contain a base fuel which may comprise fuel fractions such as the kerosene or gas oil fractions obtained in traditional refinery processes, which upgrade crude petroleum feedstock to useful products.
  • a base fuel which may comprise fuel fractions such as the kerosene or gas oil fractions obtained in traditional refinery processes, which upgrade crude petroleum feedstock to useful products.
  • fuel fractions such as the kerosene or gas oil fractions obtained in traditional refinery processes, which upgrade crude petroleum feedstock to useful products.
  • such fractions contain components having carbon numbers in the range 5 to 40, more preferably 5 to 31, yet more preferably 6 to 25, most preferably 9 to 25, and such fractions have a density at 15°C of 650 to 1000 kg/m 3 , a kinematic viscosity at 20 0 C of 1 to 80 mm 2 /s, and a boiling range of 150 to 400 0 C.
  • non-mineral oil based fuels such as bio-fuels or Fischer-Tropsch derived fuels
  • Fischer-Tropsch fuels may for example be derived from natural gas, natural gas liquids, petroleum or shale oil, petroleum or shale oil processing residues, coal or biomass .
  • the amount of Fischer-Tropsch derived fuel used in a diesel fuel composition may be from 0.5 to 100%v of the overall diesel fuel composition, preferably from 5 to 75%v. It may be desirable for the composition to contain 10%v or greater, more preferably 20%v or ⁇ rreater, still more preferably 30%v or greater, of the Fischer-Tropsch derived fuel. It is particularly preferred for the composition to contain 30 to 75%v, and particularly 30 or 70%v, of the Fischer-Tropsch derived fuel. The balance of the fuel composition is made up of one or more other fuels .
  • An industrial gas oil composition will preferably comprise more than 50 wt%, more preferably more than 70 wt%, of a Fischer-Tropsch derived fuel component.
  • Such a Fischer-Tropsch derived fuel component is any fraction of the middle distillate fuel range, which can be isolated from the (hydrocracked) Fischer-Tropsch synthesis product. Typical fractions will boil in the naphtha, kerosene or gas oil range. Preferably, a Fischer-Tropsch product boiling in the kerosene or gas oil range is used because these products are easier to handle in for example domestic environments. Such products will suitably comprise a fraction larger than 90 wt% which boils between 160 and 400 0 C, preferably to about 37O 0 C.
  • detergents suitable for use in fuel additives for the present purpose include polyolefin substituted succinimides or succinamides of polyamines, for instance polyisobutylene succinimides or polyisobutylene amine succinamides, aliphatic amines, Mannich bases or amines and polyolefin (e.g. polyisobutylene) maleic anhydrides.
  • Succinimide dispersant additives are described for example in GB-A-960493, EP-A-0147240, EP-A-0482253, EP-A-0613938, EP-A-0557516 and WO-A-98/42808.
  • Particularly preferred are polyolefin substituted succinimides such as polyisobutylene succinimides.
  • the additive include a lubricity enhancer, especially when the fuel composition has a low (e.g. 500 ppmw or less) sulphur content.
  • the lubricity enhancer is conveniently present at a concentration of less than 1000 ppmw, preferably between 50 and 1000 ppmw, more preferably between 100 and 1000 ppmw.
  • Suitable commercially available lubricity enhancers include ester- and acid-based additives.
  • Other lubricity enhancers are described in the patent literature, in particular in connection with their use in low sulphur content diesel fuels, for example in:
  • the additive components may be co-mixed, preferably together with suitable diluent (s), in an additive concentrate, and the additive concentrate may be dispersed into the fuel, in suitable quantity to result in a composition of the present invention.
  • LINEVOL LINEVOL 79 alcohol which is a mixture of 07-9 primary alcohols, or a

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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)

Abstract

L'invention concerne une composition combustible comprenant un combustible de base au gasoil, un lévulinate d'alkyle et un ou plusieurs composants supplémentaires contenant chacun un ou plusieurs constituants aromatiques. L'invention concerne également un procédé permettant de réduire la température de séparation en phases d'une composition combustible.
PCT/EP2006/064396 2005-07-25 2006-07-19 Compositions combustibles WO2007012585A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
EP06792524A EP1907513A1 (fr) 2005-07-25 2006-07-19 Compositions combustibles
AU2006274057A AU2006274057A1 (en) 2005-07-25 2006-07-19 Fuel compositions
CA002616080A CA2616080A1 (fr) 2005-07-25 2006-07-19 Compositions combustibles
BRPI0613897A BRPI0613897A2 (pt) 2005-07-25 2006-07-19 composição combustível, método para reduzir a temperatura de separação de fases de uma composição combustível, uso de um ou mais componentes adicionais, método para operar um motor de ignição por compressão e/ou um veículo que é acionado por um tal motor, método para operar um utensílio de aquecimento proporcionado com um queimador, e, processo para a preparação de uma composiçao combustível
JP2008523321A JP2009503173A (ja) 2005-07-25 2006-07-19 燃料組成物
NO20080958A NO20080958L (no) 2005-07-25 2008-02-22 Brennstoffblandinger

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP05016070.4 2005-07-25
EP05016070 2005-07-25

Publications (1)

Publication Number Publication Date
WO2007012585A1 true WO2007012585A1 (fr) 2007-02-01

Family

ID=35464110

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2006/064396 WO2007012585A1 (fr) 2005-07-25 2006-07-19 Compositions combustibles

Country Status (11)

Country Link
US (1) US20070175090A1 (fr)
EP (1) EP1907513A1 (fr)
JP (1) JP2009503173A (fr)
CN (1) CN101233216A (fr)
AR (1) AR055994A1 (fr)
AU (1) AU2006274057A1 (fr)
BR (1) BRPI0613897A2 (fr)
CA (1) CA2616080A1 (fr)
NO (1) NO20080958L (fr)
WO (1) WO2007012585A1 (fr)
ZA (1) ZA200800473B (fr)

Cited By (1)

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WO2013122686A3 (fr) * 2012-02-16 2013-10-17 Seck Karl A Bioraffinerie pour la conversion de glucides et de matières lignocellulosiques par l'intermédiaire d'un cmf hydrolysat primaire en combustibles liquides

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WO2009083490A1 (fr) * 2007-12-28 2009-07-09 Shell Internationale Research Maatschappij B.V. Utilisation d'un composant augmentant la viscosité dans un carburant diesel
CN105062582A (zh) * 2008-03-26 2015-11-18 国际壳牌研究有限公司 汽车燃料组合物
CN101633855B (zh) * 2008-07-25 2013-04-03 湖南金悦世纪能源有限公司 高清洁环保节能汽油
CA2759224A1 (fr) * 2009-06-05 2010-12-09 Energy & Environmental Research Center Foundation Bioraffinerie multiproduits pour la synthese de composants de type carburant et de produits chimiques a partir de lignocellulosiques par des condensations du levulinate
JP2011140642A (ja) * 2009-12-10 2011-07-21 Showa Shell Sekiyu Kk 潤滑油組成物
US9663739B2 (en) * 2013-05-10 2017-05-30 Chevron U.S.A. Inc. Method for increasing the maximum operating speed of an internal combustion engine operated in a low temperature combustion mode
US10760019B2 (en) * 2016-12-29 2020-09-01 Exxonmobil Research And Engineering Company Advanced combustion fuel compositions
BR112021009273A2 (pt) 2018-11-26 2021-08-10 Shell Internationale Research Maatschappij B.V. composição de combustível, uso de um aditivo de melhoria de índice de viscosidade em uma composição de combustível automotivo, e, método para operar um motor de combustão interna e/ou um veículo que é movido por tal motor
CN111171884A (zh) * 2020-03-11 2020-05-19 中国科学院兰州化学物理研究所 一种戊酸酯类汽油混合燃料
CN111171883A (zh) * 2020-03-11 2020-05-19 中国科学院兰州化学物理研究所 一种戊酸酯类柴油混合燃料

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WO1994021753A1 (fr) * 1993-03-13 1994-09-29 Veba Oel Aktiengesellschaft Carburants liquides
WO2004035713A1 (fr) * 2002-10-18 2004-04-29 Shell Internationale Research Maatschappij B.V. Compositions pour carburant
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013122686A3 (fr) * 2012-02-16 2013-10-17 Seck Karl A Bioraffinerie pour la conversion de glucides et de matières lignocellulosiques par l'intermédiaire d'un cmf hydrolysat primaire en combustibles liquides
GB2511671A (en) * 2012-02-16 2014-09-10 Karl A Seck Process for the production of fuels from carbohydrate via aldol condensation hy-droxymethylfurfural and levulinic acid or levulinic acid esters
GB2511671B (en) * 2012-02-16 2015-06-03 Karl A Seck Method of making an alkane liquid fuel
US10174262B2 (en) 2012-02-16 2019-01-08 Karl A. Seck Biorefinery for conversion of carbohydrates and lignocellulosics via primary hydrolysate CMF to liquid fuels

Also Published As

Publication number Publication date
AU2006274057A1 (en) 2007-02-01
EP1907513A1 (fr) 2008-04-09
AR055994A1 (es) 2007-09-12
CN101233216A (zh) 2008-07-30
US20070175090A1 (en) 2007-08-02
BRPI0613897A2 (pt) 2016-11-16
CA2616080A1 (fr) 2007-02-01
ZA200800473B (en) 2009-09-30
JP2009503173A (ja) 2009-01-29
NO20080958L (no) 2008-02-22

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