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
  • C10L1/185—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, 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
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
  • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
  • C10G2300/20—Characteristics of the feedstock or the products
  • C10G2300/30—Physical properties of feedstocks or products
  • C10G2300/301—Boiling range
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
  • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
  • C10G2300/20—Characteristics of the feedstock or the products
  • C10G2300/30—Physical properties of feedstocks or products
  • C10G2300/308—Gravity, density, e.g. API
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
  • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
  • C10G2400/08—Jet fuel
• • 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
  • C10L2200/00—Components of fuel compositions
  • C10L2200/04—Organic compounds
  • C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
  • C10L2200/043—Kerosene, jet fuel
• • 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
  • C10L2270/00—Specifically adapted fuels
  • C10L2270/04—Specifically adapted fuels for turbines, planes, power generation

Definitions

• the present invention relates to the field of fuels, specifically aviation fuels for use in jet engines.
• Jet aviation fuel is a complex mixture of hydrocarbons, varying according to production locale and feedstock, all complying with common specifications.
• bio-ethanol which do not live up to current engine technology as ethanol is hygroscopic, cannot form homogenous mixtures with jet aviation fuel and that lastly have an energy density that is approximately 70% of current jet aviation fuel.
• Other fuel types are bio-Diesel, made by the transesterification of fatty materials be that from plants or from animal sources.
• the long chain esters composing bio-Diesel are only partially compatible with current use in jet aviation, not only due to unfavourable physical properties, but also due to the fact that ester hydrolysis can lead to clogging of fuel lines due to precipitation of fatty acids.
• fatty acids are surface active agents, and can thus act as surfactants in situations where this in decidedly unwanted.
• current regulations limit the allowed content of fatty acid esters to less than 5 ppm in fuel pipeline systems—used in e.g. larger airports.
• ethers as fuel additives is not unknown in transportation fuels. Methyl-tert-butyl ether has seen extensive application as an anti-knock additive to petrol since its introduction in the seventies. Ethers have been prepared by a variety of routes, such as condensation of alcohols in the presence of catalysts such as concentrated sulphuric acid, ferric chloride and acid zeolites (Kirk-Othmer Encyclopedia of Chemical Technology, ISBN 9780471238966 vol. 10 p 567-583). A new route for the preparation of dibutyl ether has been disclosed in patent application US20100204522, utilizing an ionic liquid reaction medium. The document describes the industrial utility of dibutyl ether: “Ethers, such as the dialkyl ethers produced by the processes hereof, are useful as solvents, plasticizers and as additives in transportation fuels such as gasoline, diesel fuel and jet fuel.”
• EP1218472 (U.S. Pat. No. 7,014,668) teaches the use of a complex mixture of different organic compounds, with different oxygen containing functionalities for a fuel replacement for both diesel- and jet-fuel. Specifically the document discloses that one should use a mixture containing “A total of at least four different oxygen-containing functional groups are present in at least two different oxygen-containing organic compounds.”, thus excluding systems derived from less complex compounds or mixtures.
• US2009013591A1 teaches the use of more complex glycol ethers, also containing hydroxy functionalities, either as glycol or glycerol ethers, for improvement of vapour pressure and cetane value of the blended fuel of the invention.
• the document teaches the use of the additives in the replacement of conventional de-icing additives, either in full or in part.
• CN101423781 teaches the application of mixtures containing substituted ethers as fuel additives, specifying the use of a complex mixture containing terpene, 2-propanone, alkylene glycol ethers, dibasic methyl ester, nonyl phenol ethoxylate, and 0-15% mineral oil.
• the additives serve to eliminate deposit formation.
• JP10316979A teaches the use of ethers, including aromatic and benzylic ethers for increasing engine power in internal combustion gasoline engines.
• the ethers are characterized by all being methyl ethers, and further in that the long chain of the ether is 5-6C alkyl, phenyl or benzyl; the aliphatic ethers of the document being examples of known anti-knock additives for gasoline. Further the document teaches possibility of adding further 0-30% of an aromatic compound, other than an ether, presumably in order to further enhance the octane number of the gasoline fuel of the invention.
• alkyl-ethers either as pure compounds or in mixtures with variation of the chain-length of the substituted ethers allows for a simpler fuel formulation, where the ethers can be obtained directly from alcohols of biological origin. Furthermore a formulation based on ethers, or ethers in conjunction with conventional fuel components will be simpler in relation to fuel infrastructure, as only interaction of one type of functional group with said infrastructure (pumps, gaskets, fuellines etc.) will have to be investigated. Furthermore the ethers have the advantage of very low ability to solubilise water, thus reducing problems with water absorbtion. Lastly the ethers are fully miscible with conventional fuel components in all proportions.
• the present invention relates to a jet aviation fuel comprising one or more aliphatic ether compound having the general formula (I):
• R1 and R2 individually are selected from aliphatic carbon chains.
• the invention relates to containers and aerial vehicles comprising said jet aviation fuel.
• the present invention discloses ethers that can be used directly in jet aviation fuel applications, or in jet aviation fuel applications when admixed with conventional jet aviation fuel, or in jet aviation fuel application when admixed with conventional hydrocarbon fuel, where the ensuing product conforms to jet aviation fuel specification.
• conventional hydrocarbon fuel is intended a fuel distillate that does not conform to jet aviation fuel standards.
• Ethers are hydrolytically robust, non-hygroscopic and exhibit physical chemical properties that are compatible with specifications for jet aviation fuel. Not only the melting point but also the boiling point of the fuel can be controlled by choice of chain lengths or proportion of different ethers in the fuel.
• the ethers can find application in mixtures with standard jet aviation fuel, or the ethers can be used to change the physical properties of fuel, not conforming to standards in the pure state, so that said fuel can fit within jet aviation specifications.
• the variation in boiling point follows the number of carbon atoms whereas, surprisingly, the melting point does not, allowing for synthesis of low-melting ethers with high boiling point.
• the family of compounds disclosed can be varied to allow for specific combinations of melting point and vapour pressure (boiling point).
• the invention relates to these variations in physical properties, by variation of the number of carbon atoms, and the degree of branching in the aliphatic chains utilized.
• composite properties can be obtained by following the routes disclosed in the following, pertaining specifically to the pure ethers—composite properties can be obtained by blending of aliphatic ethers with different structures, or by admixing of aliphatic ethers or the mixture thereof with jet fuel, or by admixture of aliphatic ethers or mixtures thereof with hydrocarbon fuel not specified to jet aviation regulations, but where the fuel mixture obtained does conform to jet aviation fuel specification.
• the overall boiling point of the fuel can be optimized for a specific application by controlling the overall number of carbon atoms in the aliphatic ether.
• the melting point of the aliphatic ethers, and thus the low-temperature properties can be modified by selecting the chain-length and branching of the aliphatic chains.
• Examples according to the invention being, but not limited to; Dipentyl ether with ten carbon atoms MP ⁇ 69° C., Iso-pentyl octyl ether with thirteen carbon atoms MP ⁇ 56.5° C., 1-Methyl-propyl)-octyl ether with twelve carbon atoms MP ⁇ 54° C., Methyl octyl ether with nine carbon atoms MP ⁇ 52.5° C.
• the melting point surprisingly does not follow the number of carbon atoms, and indeed in the examples given Methyl octyl ether with nine carbon atoms exhibit a melting point of ⁇ 52.5° C., while Iso-pentyl octyl ether with thirteen carbon atoms exhibit a melting point of ⁇ 56.5° C.
• the longer chain of the ether can, following the same rules, have four, five, six, seven, eight, nine, eleven, twelve, thirteen or fourteen carbon atoms, and said chain can be either un-branched as in e.g. Dipentyl ether or branched as in Iso-pentyl octyl ether.
• the aliphatic ethers can be symmetrical such as Dipentyl ether or unsymmetrical such as Methyl octyl ether.
• the aliphatic ethers may be used as an jet aviation fuel in the pure form as single compounds, or they may be used as a mixture of different ethers of the type disclosed.
• the aliphatic ether or mixtures of aliphatic ethers may be used as an jet aviation fuel (100%) or they may be used in mixtures such as, but not limited to, 50%, 25%, 10% or until 5% of the aliphatic ether or mixtures of aliphatic ethers, admixed with conventional jet aviation fuel.
• the aliphatic ether or mixtures of aliphatic ethers may be used as a jet aviation fuel in mixtures such as, but not limited to, 50%, 25%, 10% or until 5% of the aliphatic ether or mixtures of aliphatic ethers, admixed with conventional hydrocarbon fuel where the fuel obtained conforms to jet aviation fuel standards even when the conventional hydrocarbon fuel admixed does not.
• the present invention relates to a jet aviation fuel comprising one or more aliphatic ether compounds having the general formula (I):
• R1 and R2 individually are selected from aliphatic carbon chains.
• the total number of carbon atoms of the aliphatic ether compound is at least 6.
• the total number of carbon atoms of the aliphatic ether compound is at least 7.
• the total number of carbon atoms of the aliphatic ether compound is at least 8.
• the total number of carbon atoms of the aliphatic ether compound is at least 9.
• the total number of carbon atoms of the aliphatic ether compound is at least 10.
• the total number of carbon atoms of the aliphatic ether compound is at least 11.
• the total number of carbon atoms of the aliphatic ether compound is at least 13.
• the aliphatic carbon chain of formula I comprising the lowest number of carbon atoms comprises at least one carbon atom. In one embodiment the aliphatic carbon chain comprising the lowest number of carbon atoms is R1. In another embodiment the aliphatic carbon chain comprising the lowest number of carbon atoms is R2.
• the carbon chain of formula (I) comprising the lowest number of carbon atoms comprises at least two carbon atoms.
• the carbon chain of formula (I) comprising the lowest number of carbon atoms comprises at least three carbon atoms.
• R1 and R2 of formula (I) comprises the same number of carbon atoms.
• R1 and R2 are both un-branched.
• R1 is branched while R2 is un-branched.
• R2 is branched while R1 is un-branched.
• the one or more aliphatic ether compounds are two, three, four, five, six, seven, eight, nine, ten, eleven, twelve or more different aliphatic ether compounds, wherein the two, three, four, five, six, seven, eight, nine, ten, eleven, twelve or more different aliphatic ether compounds individually are as defined herein above.
• the one or more aliphatic ether compounds are 13 or more different aliphatic ether compounds, such as 14 or more different aliphatic ether compounds, for example 15 or more different aliphatic ether compounds, such as 16 or more different aliphatic ether compounds, for example 17 or more different aliphatic ether compounds, such as 18 or more different aliphatic ether compounds, for example 19 or more different aliphatic ether compounds, such as at least 20 or more different aliphatic ether compounds, and wherein said different aliphatic ether compounds individually are as defined herein above.
• the one or more aliphatic ether compound is selected from the group consisting of Propyl butyl ether, Diisopentyl ether, Propyl pentyl ether, Isopropyl pentyl ether, Butyl pentyl ether, Pentyl ether, Methyl hexyl ether, Ethyl hexyl ether, Propyl hexyl ether, Isopropyl hexyl ether, Butyl hexyl ether, (1-Methylpropyl) hexyl ether, Pentyl hexyl ether, Hexyl ether, Methyl heptyl ether, Ethyl heptyl ether, Propyl heptyl ether, Butyl heptyl ether, Pentyl heptyl ether, Isoamyl heptyl ether, Methyl butyl
• the one or more aliphatic ether compound is selected from the group consisting of aliphatic ether compounds having a boiling point between 115° C. and 300° C., preferably between 200° C. and 300° C.
• the one or more aliphatic ether compound is selected from the group consisting of aliphatic ether compounds having a density of between 0.71 and 0.82 g/cm 3 .
• the jet aviation fuel as defined herein above contains a 50% admixture of conventional jet aviation fuel.
• the jet aviation fuel consists entirely of one or more aliphatic ether compounds wherein said different aliphatic ether compounds are as defined herein above.
• the jet aviation fuel as defined herein above contains at least a 55% admixture of conventional jet aviation fuel, such as at least a 60% admixture of conventional jet aviation fuel, for example at least a 65% admixture of conventional jet aviation fuel.
• the jet aviation fuel of the present invention contains a 75% admixture of conventional jet aviation fuel, such as at least a 80% admixture of conventional jet aviation fuel, for example at least a 85% admixture of conventional jet aviation fuel, such as at least a 87% admixture of conventional jet aviation fuel,
• the jet aviation fuel as defined herein above contains a 90% admixture of conventional jet aviation fuel, such as at least a 91% admixture of conventional jet aviation fuel, for example at least a 92% admixture of conventional jet aviation fuel, such as at least a 93% admixture of conventional jet aviation fuel, for example at least a 94% admixture of conventional jet aviation fuel, such as at least a 95% admixture of conventional jet aviation fuel, for example at least a 96% admixture of conventional jet aviation fuel, such as at least a 97% admixture of conventional jet aviation fuel, for example at least a 98% admixture of conventional jet aviation fuel, such as at least a 99% admixture of conventional jet aviation fuel.
• conventional jet aviation fuel such as at least a 91% admixture of conventional jet aviation fuel, for example at least a 92% admixture of conventional jet aviation fuel, such as at least a 93% admixture of conventional jet aviation fuel, for example at least a 94%
• the jet aviation fuel as defined herein above contains an at least 50% admixture of a conventional hydrocarbon fuel, and wherein the fuel mixture thus obtained conforms to jet aviation fuel standards.
• the jet aviation fuel as defined herein above contains an at least 55% admixture of a conventional hydrocarbon fuel, and wherein the fuel mixture thus obtained conforms to jet aviation fuel standards.
• the jet aviation fuel as defined herein above contains an at least 60% admixture of a conventional hydrocarbon fuel, and wherein the fuel mixture thus obtained conforms to jet aviation fuel standards.
• the jet aviation fuel as defined herein above contains an at least 65% admixture of a conventional hydrocarbon fuel, and wherein the fuel mixture thus obtained conforms to jet aviation fuel standards.
• the jet aviation fuel as defined herein above contains an at least 70% admixture of a conventional hydrocarbon fuel, and wherein the fuel mixture thus obtained conforms to jet aviation fuel standards.
• the jet aviation fuel as defined herein above an at least 75% admixture of a conventional hydrocarbon fuel, and wherein the fuel mixture thus obtained conforms to jet aviation fuel standards.
• the jet aviation fuel as defined herein above contains an at least 80% admixture of a conventional hydrocarbon fuel, and wherein the fuel mixture thus obtained conforms to jet aviation fuel standards.
• the jet aviation fuel as defined herein above contains an at least 85% admixture of a conventional hydrocarbon fuel, and wherein the fuel mixture thus obtained conforms to jet aviation fuel standards.
• the jet aviation fuel as defined herein above contains an at least 90% admixture of a conventional hydrocarbon fuel, and wherein the fuel mixture thus obtained conforms to jet aviation fuel standards.
• the jet aviation fuel as defined herein above contains an at least 95% admixture of a conventional hydrocarbon fuel, and wherein the fuel mixture thus obtained conforms to jet aviation fuel standards.
• the jet aviation fuel as defined herein above is not for use for increasing the engine power in internal combustion gasoline engines.
• R1 is not methyl, when R2 is C5 or C6 alkyl, phenyl or benzyl.
• R2 is not methyl, when R1 is C5 or C6 alkyl, phenyl or benzyl.
• the present invention relates to the use of the jet aviation fuel as defined herein above in a jet engine.
• said jet engine is selected from the group consisting of turbojet engine, turboprop jet engine, turbofan jet engine, and turboshaft jet engine.
• the present invention relates to a container comprising the jet aviation fuel as defined herein above.
• the present invention relates to an aerial vehicle comprising the container defined herein above.
• the present invention concerns an aerial vehicle comprising the jet aviation fuel as defined herein above.
• Jet aviation fuel compositions vary widely according to geographical variation and intended application.
• the requirements for fuel used for long distance flying such as e.g. transatlantic crossings poses stricter limits as to low temperature performance as compared to less demanding application.
• Table 2 are shown pertinent parameters for some of the commonly used jet-fuel specifications:
• Methyl heptyl ether 10% Methyl octyl ether 40% (1-Methylpropyl) octyl ether 40% Isopentyl octyl ether 10%
• a jet aviation fuel based on aliphatic ethers where the fuel consist of one or more compounds according to the invention, a mixture of compounds according to the invention, a mixture of the pure or mixed aliphatic ethers admixed with conventional jet aviation fuel, or a mixture of said ethers with conventional hydrocarbon fuel, giving a product conforming to a jet aviation fuel standard.

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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)

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• 2011
  • 2011-05-30 WO PCT/DK2011/000053 patent/WO2011150924A1/en active Application Filing
  • 2011-05-30 US US13/700,787 patent/US20130074398A1/en not_active Abandoned
  • 2011-05-30 EP EP11789277.8A patent/EP2576736A4/de not_active Withdrawn

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