EP1685217B1 - Brennstoffzusammensetzungen mit einem lävulinsäure-c4-c8-alkylester - Google Patents
Brennstoffzusammensetzungen mit einem lävulinsäure-c4-c8-alkylester Download PDFInfo
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- EP1685217B1 EP1685217B1 EP04818157A EP04818157A EP1685217B1 EP 1685217 B1 EP1685217 B1 EP 1685217B1 EP 04818157 A EP04818157 A EP 04818157A EP 04818157 A EP04818157 A EP 04818157A EP 1685217 B1 EP1685217 B1 EP 1685217B1
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- Prior art keywords
- fuel
- levulinate
- alkyl
- fuel composition
- diesel
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Classifications
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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, 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
Definitions
- the present invention relates to fuel compositions comprising a gas oil base fuel, particularly to such compositions containing a levulinate ester, more particularly a C 4-8 alkyl levulinate, 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 levulinic acid
- furfuryl acetate is 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 C 4-6 keto-carbonic acids, preferably levulinic acid, with C 1-22 alcohols.
- Esters with C 1-8 alcohols are described as being particularly suitable for inclusion in gasolines, and esters with C 9-22 alcohols are described as being particularly suitable for inclusion in diesel fuels.
- WO-A-03/002696 discloses a fuel composition incorporating levulinic acid, or a functional derivative thereof, with the object of providing more oxygen by volume than ethanol or traditional oxygenates such as MTBE or ETBE, giving little or no increase in fuel Reid vapour pressure and little or no effect on the flash point of the base fuel.
- the functional derivative is preferably an alkyl derivative, more preferably a C 1-10 alkyl derivative. Ethyl levulinate is said to be preferred, with methyl levulinate a preferred alternative.
- the levulinic acid or functional derivative is preferably used to form 0.1 to 5%v of the fuel.
- WO-A-03/085071 discloses the use of levulinic acid esters as fuel additives for gaseline fuel, diesel fuel and biofuel.
- a further complication can arise when an engine is run on a fuel blend instead of a standard base fuel.
- the fuel comes into contact with a range of elastomeric materials, in particular fuel pump seals.
- many of these elastomers swell on contact with diesel fuel to an extent which depends on the chemistry of the fuel, aromatic fuel components and oxygenates serving for instance to promote swelling.
- New elastomers in a fuel injection system tend to equilibrate with a uniform fuel diet and can thus provide with reasonable consistency the required level of sealing. They become vulnerable, however, if a change in fuel diet causes any significant change in the degree of elastomer swell. In the worst cases a mixed fuel diet can stress the elastomeric components of an engine to such an extent that fuel leakage results.
- 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.
- a fuel composition comprising a gas oil base fuel and an alkyl levulinate in a concentration of at least 1% v and up to 12% v, wherein said alkyl levulinate is a C 4-8 alkyl levulinate, and wherein the phase separation temperature of said fuel composition is below a predetermined level, said level being -10°C, more preferably -20°C, and most preferably -30°C.
- said alkyl levulinate is selected from C 4-6 alkyl levulinates, more preferably n-butyl levulinate, n-pentyl levulinate and 2-hexyl levulinate, or said alkyl levulinate is a C 5 alkyl levulinate.
- said alkyl levulinate preferably is n-pentyl levulinate.
- a fuel composition comprising a gas oil base fuel and an alkyl levulinate of a C 4-8 alkyl levulinate as said alkyl levulinate, for the purpose of ensuring a phase separation temperature of said fuel composition below -10°C, more preferably -20°C, and most preferably -30°C.
- said alkyl levulinate is selected from C 4-6 alkyl levulinates, more preferably n-butyl levulinate, n-pentyl levulinate and 2-hexyl levulinate, or more preferably said alkyl levulinate is a C 5 alkyl levulinate.
- said alkyl levulinate preferably is n-pentyl levulinate.
- phase separation temperature of a fuel composition comprising a gas oil base fuel and ethyl levulinate, by replacing at least partially said ethyl levulinate with a C 4-8 alkyl levulinate.
- This preferably comprises reducing the phase separation temperature below a predetermined level, said level preferably being -10°C, more preferably -20°C, and most preferably -30°C.
- a method of operating a compression ignition engine and/or a vehicle which is powered by such an engine which method involves introducing into a combustion chamber of the engine a fuel composition according to the present invention.
- 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 according to the present invention which process involves blending a gas oil base fuel and a C 4-8 alkyl levulinate in a concentration of at least 1% v and up to 12% v based on the final composition.
- said alkyl levulinate is selected from C 4-6 alkyl levulinates, more preferably n-butyl levulinate, n-pentyl levulinate and 2-hexyl levulinate, or said alkyl levulinate is a C 5 alkyl levulinate.
- said alkyl levulinate preferably is n-pentyl levulinate.
- blends of two or more of the C 4-8 alkyl levulinates may be included in the fuel composition, such as for example a blend n-butyl levulinate and n-pentyl levulinate.
- 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 to 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 C 4-8 alkyl levulinates will be chosen to achieve the desired degree of miscibility, i.e. phase separation temperature, and elastomer swell and hardness effects, and may also be influenced by other properties required of the overall composition.
- the effects on elastomeric engine components may include changes in the physical properties (e.g. volume, hardness and/or flexibility) of a given elastomeric material on contact with, suitably immersion in, the relevant fuel or fuel composition, for instance inside a diesel engine into which the relevant fuel is introduced.
- Tyically such changes include an increase in volume and/or a reduction in hardness. They may be measured using standard test procedures such as BS903, ASTM D471, D2240 or ISO 1817:1998, for instance as described in Example 2 below. They may be assessed in particular for nitrile (including hydrogenated nitrile) elastomers, or for fluorocarbon elastomers.
- the C 4-8 alkyl levulinates are included in the fuel composition at proportions such as to cause a change in volume of any given elastomeric material (for example a fluorocarbon type such as LR 6316 (ex. James Walker & Co. Ltd., UK)) which is not significantly different from that caused by the base fuel when tested under the same conditions.
- any given elastomeric material for example a fluorocarbon type such as LR 6316 (ex. James Walker & Co. Ltd., UK)
- LR 6316 ex. James Walker & Co. Ltd., UK
- the C 4-8 alkyl levulinates are included in the fuel composition at proportions such as to cause a change in hardness of any given elastomeric material (for example a fluorocarbon type such as LR 6316) which is not significantly different from that caused by the base fuel when tested under the same conditions.
- the proportions are such as to achieve a change in elastomer hardness which is no higher than that of the base fuel alone, ideally 95 % or 90 % or 85 % or less of that caused by the base fuel.
- 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 with the usual diesel range of 150 to 400°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°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 230°C and a final boiling point in the range 290 to 400°C. Their kinematic viscosity at 40°C (ASTM D445) might suitably be from 1.5 to 4.5 mm 2 /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 5-40, more preferably 5-31, yet more preferably 6-25, most preferably 9-25, and such fractions have a density at 15°C of 650-950 kg/m 3 , a kinematic viscosity at 20°C of 1-80 mm 2 /s, and a boiling range of 150-400°C.
- non-mineral oil based fuels such as bio-fuels or Fischer-Tropsch derived fuels, may also form or be present in the fuel composition.
- 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 greater, 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°C, preferably to about 370°C.
- Fischer-Tropsch derived kerosene and gas oils are described in EP-A-0583836 , WO-A-97/14768 , WO-A-97/14769 , WO-A-00/11116 , WO-A-00/11117 , WO-A-01/83406 , WO-A-01/83648 , WO-A-01/83647 , WO-A-01/83641 , WO-A-00/20535 , WO-A-00/20534 , EP-A-1101813 , US-A-5766274 , US-A-5378348 , US-A-5888376 and US-A-6204426 .
- the Fischer-Tropsch product will suitably contain more than 80 wt% and more suitably more than 95 wt% iso and normal paraffins and less than 1 wt% aromatics, the balance being naphthenics compounds.
- the content of sulphur and nitrogen will be very low and normally below the detection limits for such compounds. For this reason the sulphur content of a fuel composition containing a Fischer-Tropsch product may be very low.
- the fuel composition preferably contains no more than 5000ppmw sulphur, more preferably no more than 500ppmw, or no more than 350ppmw, or no more than 150ppmw, or no more than 100ppmw, or no more than 50ppmw, or most preferably no more than 10ppmw sulphur.
- the fuel composition of the present invention may, if required, contain one or more additives as described below.
- the base fuel may itself be additivated (additive-containing) or unadditivated (additive-free). If additivated, e.g. at the refinery, it will contain minor amounts of one or more additives selected for example from anti-static agents, pipeline drag reducers, flow improvers (e.g. ethylene/vinyl acetate copolymers or acrylate/maleic anhydride copolymers) and wax antisettling agents (e.g. those commercially available under the Trade Marks "PARAFLOW” (e.g. PARAFLOWTM 450, ex Infineum), "OCTEL” (e.g. OCTELTM W 5000, ex Octel) and "DODIFLOW” (e.g. DODIFLOWTM v 3958, ex Hoechst).
- additives selected for example from anti-static agents, pipeline drag reducers, flow improvers (e.g. ethylene/vinyl acetate copolymers or acrylate/maleic anhydride copo
- Detergent-containing diesel fuel additives are known and commercially available, for instance from Infineum (e.g. F7661 and F7685) and Octel (e.g. OMA 4130D). Such additives may be added to diesel fuels at relatively low levels (their "standard” treat rates providing typically less than 100 ppmw active matter detergent in the overall additivated fuel composition) intended merely to reduce or slow the build up of engine deposits.
- 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 may contain other components in addition to the detergent.
- lubricity enhancers e.g. alkoxylated phenol formaldehyde polymers such as those commercially available as NALCOTM EC5462A (formerly 7D07) (ex Nalco) and TOLADTM 2683 (ex Petrolite); anti-foaming agents (e.g. the polyether-modified polysiloxanes commercially available as TEGOPRENTM 5851 and Q 25907 (ex Dow Corning), SAGTM TP-325 (ex OSi) and RHODORSILTM (ex Rhone Poulenc)); ignition improvers (cetane improvers) (e.g.
- the pentaerythritol diester of polyisobutylene-substituted succinic acid corrosion inhibitors; reodorants; anti-wear additives; anti-oxidants (e.g. phenolics such as 2,6-di-tertbutylphenol, or phenylenediamines such as N,N'-di-sec-butyl-p-phenylenediamine); and metal deactivators.
- 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 between 50 and 1000 ppmw, preferably between 100 and 1000 ppmw.
- Suitable commercially available lubricity enhancers include EC 832 and PARADYNETM 655 (ex Infineum), HITECTM E580 (ex Ethyl Corporation), VEKTRONTM 6010 (ex Infineum) and amide-based additives such as those available from the Lubrizol Chemical Company, for instance LZ 539 C.
- 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 contain an anti-foaming agent, more preferably in combination with an anti-rust agent and/or a corrosion inhibitor and/or a lubricity additive.
- the (active matter) concentration of each such additional component in the additivated fuel composition is preferably up to 10000 ppmw, more preferably in the range from 5 to 1000 ppmw, advantageously from 75 to 300 ppmw, such as from 95 to 150 ppmw.
- the (active matter) concentration of any dehazer in the fuel composition will preferably be in the range from 1 to 20 ppmw, more preferably from 1 to 15 ppmw, still more preferably from 1 to 10 ppmw, advantageously from 1 to 5 ppmw.
- the (active matter) concentration of any ignition improver present will preferably be 600 ppmw or less, more preferably 500 ppmw or less, conveniently from 300 to 500 ppmw.
- 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.
- the additive will typically contain a detergent, optionally together with other components as described above, and a diesel fuel-compatible diluent, which may be a carrier oil (e.g. a mineral oil), a polyether, which may be capped or uncapped, a non-polar solvent such as toluene, xylene, white spirits and those sold by member companies of the Royal Dutch/Shell Group under the trade mark "SHELLSOL", and/or a polar solvent such as an ester and, in particular, an alcohol, e.g.
- a carrier oil e.g. a mineral oil
- a polyether which may be capped or uncapped
- a non-polar solvent such as toluene, xylene, white spirits and those sold by member companies of the Royal Dutch/Shell Group under the trade mark "SHELLSOL”
- a polar solvent such as an ester and, in particular, an alcohol, e.g.
- hexanol 2-ethylhexanol, decanol, isotridecanol and alcohol mixtures such as those sold by member companies of the Royal Dutch/Shell Group under the trade mark "LINEVOL”, especially LINEVOLTM 79 alcohol which is a mixture of C 7-9 primary alcohols, or the C 12-14 alcohol mixture commercially available from Sidobre Sinnova, France under the trade mark "SIPOL”.
- LINEVOL especially LINEVOLTM 79 alcohol which is a mixture of C 7-9 primary alcohols, or the C 12-14 alcohol mixture commercially available from Sidobre Sinnova, France under the trade mark "SIPOL”.
- the total content of the additives may be suitably between 0 and 10000 ppmw and preferably below 5000 ppmw.
- the C 4-8 alkyl levulinate concentration in the fuel composition accords with one or more of the following parameters:-
- amounts (concentrations, %v, ppmw, wt%) of components are of active matter, i.e. exclusive of volatile solvents/diluent materials.
- the present invention is particularly applicable where the fuel composition is used or intended to be used in a direct injection diesel engine, for example of the rotary pump, in-line pump, unit pump, electronic unit injector or common rail type, or in an indirect injection diesel engine. It may be of particular value for rotary pump engines, and in other diesel engines which rely on mechanical actuation of the fuel injectors and/or a low pressure pilot injection system.
- the fuel composition may be suitable for use in heavy and/or light duty diesel engines.
- the fuel composition is used in heating applications, such as boilers, including standard boilers, low temperature boilers and condensing boilers.
- boilers are typically used for heating water for commercial or domestic applications such as space heating and water heating.
- the present invention may lead to any of a number of advantageous effects, including good engine low temperature performance.
- ethyl levulinate available ex. Avocado
- n-butyl levulinate available ex. Aldrich
- n-pentyl levulinate available ex. City Chemical or by the reaction of 1-pentanol (available ex. Aldrich) with levulinic acid (available ex. Aldrich)
- 2-hexyl levulinate prepared by the reaction of 1-hexene (available ex. Fluka) or of 2-hexanol (available ex. Aldrich) with levulinic acid).
- Fuel A was an ultra low sulphur diesel (ULSD), which is typical of a 2005 specification European diesel fuel, with a cloud point of -8°C and an aromatics content of 25%m;
- Fuel B was a Dreyfuss ULSD, which is a hydrotreated AGO having a lower cloud point (-27°C) and a similar aromatics content to Fuel A (22%m), which complied with European specification EN590;
- Fuel C was a Swedish Class 1 AGO, which is a low density, low aromatics (4%m) diesel fuel with the lowest cloud point of the three base fuels (-38°C).
- Fuels A, B and C are given in Table 1.
- Table 1 Fuel A Fuel B Fuel C Density @ 15°C, kg/m 3 834 822 815 Distillation T50, °C 280 242 235 Distillation T95, °C 343 304 272 Cetane Number 56 54 54 Viscosity @40°C, mm 2 /s 2.91 2.10 2.03 Sulphur, mg/kg 38 10 ⁇ 5 Cloud Point, °C -8 -27 -38 Aromatics, %m 25 22 4
- the effect of various alkyl levulinate compounds on elastomer seals was assessed using a test procedure based on ISO 1817:1998.
- the volume and average Shore hardness of elastomer samples were measured both before and after immersion in 100ml of test fuel at ambient temperature (20°C) for 168 hours. Thereafter, the samples were removed from the test fluid, quickly surface dried, weighed in air and in water and their new volume and hardness measured within 8 hours of their removal from the test medium. Hardness was measured at ambient temperature using a Type A Shore TM Durometer (Shore Instruments, USA). The percentage changes in volume and in average hardness, due to exposure to the test fuel, were then reported for each sample.
- Tests were conducted to compare the effects on elastomers of: ethyl levulinate, n-butyl levulinate, n-pentyl levulinate and 2-hexyl levulinate. Each of these compounds was blended at 5%v concentration into a base fuel, Fuel D, which was a conventional diesel fuel sample. The properties of Fuel D and of a blend of 5%v n-pentyl levulinate in Fuel D are shown in Table 5. Table 5 Property EN 590:2000 spec.
- the elastomer material was chosen to be representative of the seals (O-rings, etc.) used in modern diesel fuel systems: LR 6316 (a fluorocarbon tetrapolymer also known as Viton (trade mark) (ex. James Walker & Co. Ltd., UK). It was chosen as an elastomer which is typical of those used in modern diesel fuel systems and which, although less susceptible to seal swell than some other elastomer materials, is able to highlight significant changes in swell properties.
- n-butyl levulinate, n-pentyl levulinate and 2-hexyl levulinate produced substantially less seal swell (i.e. % volume change) than ethyl levulinate, and that the change in hardness with n-butyl levulinate, n-pentyl levulinate and 2-hexyl levulinate was substantially less than with ethyl levulinate and not significantly different from conventional Fuel D.
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Claims (9)
- Kraftstoffzusammensetzung, umfassend einen Gasölbasiskraftstoff und ein Alkyllävulinat in einer Konzentration von mindestens 1 Vol.-% und von bis zu 12 Vol.-%, wobei das Alkyllävulinat ein C4-8 Alkyllävulinat ist und wobei die Phasentrennungstemperatur des Kraftstoffs unter - 10°C liegt.
- Kraftstoffzusammensetzung nach Anspruch 1, wobei die Phasentrennungstemperatur unter -20°C liegt.
- Kraftstoffzusammensetzung nach Anspruch 2, wobei die Phasentrennungstemperatur unter -30°C liegt
- Kraftstoffzusammensetzung nach einem der Ansprüche 1 bis 3, wobei das Alkyllävulinat wahlweise n-Butyllävulinat, n-Pentyllävulinat oder 2-Hexyllävulinat ist.
- Kraftstoffzusammensetzung nach Anspruch 4, wobei das Alkyllävulinat n-Pentyllävulinat ist.
- Verwendung einer Kraftstoffzusammensetzung nach einem der Ansprüche 1 bis 5 zur Gewährleistung einer Phasentrennungstemperatur der Kraftstoffzusammensetzung unter -10°C.
- Verfahren zum Betreiben eines Selbstzündungsmotors und/oder eines Fahrzeugs, welches durch einen solchen Motor angetrieben wird, welches Verfahren ein Einbringen einer Kraftstoffzusammensetzung nach einem der Ansprüche 1 bis 5 in einen Brennraum des beinhaltet.
- Verfahren zum Betreiben einer mit einem Brenner ausgestatteten Heizeinrichtung, umfassend ein Versorgen dieses Brenners mit einer Kraftstoffzusammensetzung nach einem der Ansprüche 1 bis 5.
- Verfahren zur Herstellung einer Kraftstoffzusammensetzung nach Anspruch 1, welches Verfahren ein Mischen eines Ölgasbasiskraftstoffs und eines C4-8 Alkyllävulinats in einer Konzentration von mindestens 1 Vol.-% und von bis zu 12 Vol.-% auf Basis der endgültigen Zusammensetzung beinhaltet.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP04818157A EP1685217B1 (de) | 2003-11-10 | 2004-11-08 | Brennstoffzusammensetzungen mit einem lävulinsäure-c4-c8-alkylester |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP03257073 | 2003-11-10 | ||
PCT/EP2004/052845 WO2005044960A1 (en) | 2003-11-10 | 2004-11-08 | Fuel compositions comprising a c4-c8 alkyl levulinate |
EP04818157A EP1685217B1 (de) | 2003-11-10 | 2004-11-08 | Brennstoffzusammensetzungen mit einem lävulinsäure-c4-c8-alkylester |
Publications (2)
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EP1685217A1 EP1685217A1 (de) | 2006-08-02 |
EP1685217B1 true EP1685217B1 (de) | 2012-12-12 |
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EP04818157A Not-in-force EP1685217B1 (de) | 2003-11-10 | 2004-11-08 | Brennstoffzusammensetzungen mit einem lävulinsäure-c4-c8-alkylester |
Country Status (9)
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US (1) | US20050144835A1 (de) |
EP (1) | EP1685217B1 (de) |
JP (1) | JP5132937B2 (de) |
CN (1) | CN1886488A (de) |
BR (1) | BRPI0416356A (de) |
CA (1) | CA2545170C (de) |
NO (1) | NO20062725L (de) |
WO (1) | WO2005044960A1 (de) |
ZA (1) | ZA200603455B (de) |
Families Citing this family (12)
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EP1732876A1 (de) * | 2004-03-24 | 2006-12-20 | E.I.Du pont de nemours and company | Herstellung von levulinsäureestern aus alpha-angelicalacton und -alkoholen |
AU2006274057A1 (en) * | 2005-07-25 | 2007-02-01 | Shell Internationale Research Maatschappij B.V. | Fuel compositions |
CA2616082A1 (en) * | 2005-07-25 | 2007-02-01 | Shell Internationale Research Maatschappij B.V. | Fuel compositions |
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 |
EP2304001B1 (de) * | 2008-07-02 | 2019-08-07 | Shell International Research Maatschappij B.V. | Flüssigkraftstoffzusammensetzungen |
WO2010106536A1 (en) * | 2009-03-16 | 2010-09-23 | Ben-Gurion University Of The Negev Research And Development Authority | Diesel fuel from vegetable and animal oils blended with alkyl levulinates |
US20100313467A1 (en) * | 2009-06-16 | 2010-12-16 | Meadwestvaco Corporation | Diesel fuel compositions containing levulinate ester |
CN102796573B (zh) * | 2012-07-24 | 2014-09-17 | 北京金骄生物质化工有限公司 | 一种低凝生物柴油混合燃料及其制备方法 |
WO2015091091A1 (en) | 2013-12-19 | 2015-06-25 | Basf Se | Cosmetic composition |
CN107667163B (zh) * | 2015-02-10 | 2020-04-17 | 阿凡田知识中心有限公司 | 含有腐殖质的燃料组合物 |
ES2901300T3 (es) | 2016-07-08 | 2022-03-22 | Basf Se | Agentes solubilizantes para filtros uv en formulaciones cosméticas |
CN107841350A (zh) * | 2016-09-18 | 2018-03-27 | 北京特生物化工有限公司 | 一种生物基酯类微乳化柴油及其制备方法 |
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US3563715A (en) * | 1958-07-15 | 1971-02-16 | Chevron Res | Motor fuels |
US3879176A (en) * | 1970-12-11 | 1975-04-22 | Nippon Oil Co Ltd | Liquefied petroleum gas compositions |
US4208190A (en) * | 1979-02-09 | 1980-06-17 | Ethyl Corporation | Diesel fuels having anti-wear properties |
US5290325A (en) * | 1990-02-28 | 1994-03-01 | Union Oil Company Of California | Hydrocarbon fuel composition containing alpha-ketocarboxylate additive |
US5490864A (en) * | 1991-08-02 | 1996-02-13 | Texaco Inc. | Anti-wear lubricity additive for low-sulfur content diesel fuels |
DE4308053C2 (de) * | 1993-03-13 | 1997-05-15 | Veba Oel Ag | Flüssige unverbleite Kraftstoffe |
US5378348A (en) * | 1993-07-22 | 1995-01-03 | Exxon Research And Engineering Company | Distillate fuel production from Fischer-Tropsch wax |
US5484462A (en) * | 1994-09-21 | 1996-01-16 | Texaco Inc. | Low sulfur diesel fuel composition with anti-wear properties |
US5888376A (en) * | 1996-08-23 | 1999-03-30 | Exxon Research And Engineering Co. | Conversion of fischer-tropsch light oil to jet fuel by countercurrent processing |
US5766274A (en) * | 1997-02-07 | 1998-06-16 | Exxon Research And Engineering Company | Synthetic jet fuel and process for its production |
US6475252B1 (en) * | 1998-09-17 | 2002-11-05 | University Of Dayton | Stabilizing additive for the prevention of oxidation and peroxide formation |
US6204426B1 (en) * | 1999-12-29 | 2001-03-20 | Chevron U.S.A. Inc. | Process for producing a highly paraffinic diesel fuel having a high iso-paraffin to normal paraffin mole ratio |
GB0111679D0 (en) * | 2001-05-12 | 2001-07-04 | Aae Tech Int Ltd | Fuel composition |
GB2387175A (en) * | 2002-03-13 | 2003-10-08 | Shell Int Research | Oxidised fuel formulations |
US7153996B2 (en) * | 2002-04-01 | 2006-12-26 | E.I. Du Pont De Nemours And Company | Preparation of levulinic acid esters and formic acid esters from biomass and olefins |
MY140297A (en) * | 2002-10-18 | 2009-12-31 | Shell Int Research | A fuel composition comprising a base fuel, a fischer-tropsch derived gas oil and an oxygenate |
-
2004
- 2004-11-08 WO PCT/EP2004/052845 patent/WO2005044960A1/en active Search and Examination
- 2004-11-08 EP EP04818157A patent/EP1685217B1/de not_active Not-in-force
- 2004-11-08 CN CNA2004800353084A patent/CN1886488A/zh active Pending
- 2004-11-08 CA CA2545170A patent/CA2545170C/en not_active Expired - Fee Related
- 2004-11-08 BR BRPI0416356-7A patent/BRPI0416356A/pt not_active IP Right Cessation
- 2004-11-08 JP JP2006538850A patent/JP5132937B2/ja not_active Expired - Fee Related
- 2004-11-10 US US10/985,613 patent/US20050144835A1/en not_active Abandoned
-
2006
- 2006-05-02 ZA ZA200603455A patent/ZA200603455B/xx unknown
- 2006-06-12 NO NO20062725A patent/NO20062725L/no not_active Application Discontinuation
Also Published As
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AU2004287631A1 (en) | 2005-05-19 |
CA2545170A1 (en) | 2005-05-19 |
US20050144835A1 (en) | 2005-07-07 |
JP5132937B2 (ja) | 2013-01-30 |
NO20062725L (no) | 2006-06-12 |
ZA200603455B (en) | 2007-08-29 |
WO2005044960A1 (en) | 2005-05-19 |
CA2545170C (en) | 2013-10-22 |
BRPI0416356A (pt) | 2007-03-13 |
EP1685217A1 (de) | 2006-08-02 |
CN1886488A (zh) | 2006-12-27 |
JP2007510787A (ja) | 2007-04-26 |
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