US20030000131A1 - Composition - Google Patents

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Publication number
US20030000131A1
US20030000131A1 US10/105,921 US10592102A US2003000131A1 US 20030000131 A1 US20030000131 A1 US 20030000131A1 US 10592102 A US10592102 A US 10592102A US 2003000131 A1 US2003000131 A1 US 2003000131A1
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Prior art keywords
fuel
composition according
group
nitrogens
fuels
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US10/105,921
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Inventor
Cyrus Henry
David Pinch
Andrea Sneddon
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Associated Octel Co Ltd
Octel America Inc
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Associated Octel Co Ltd
Octel America Inc
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Priority claimed from GB0118648A external-priority patent/GB0118648D0/en
Application filed by Associated Octel Co Ltd, Octel America Inc filed Critical Associated Octel Co Ltd
Priority to US10/105,921 priority Critical patent/US20030000131A1/en
Assigned to OCTEL AMERICA, INC., ASSOCIATED OCTEL COMPANY LIMITED, THE reassignment OCTEL AMERICA, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HENRY, CYRUS PERSHING, JR., PINCH, DAVID LEONARD, SNEDDON, ANDREA
Publication of US20030000131A1 publication Critical patent/US20030000131A1/en
Abandoned legal-status Critical Current

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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
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • 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
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
    • 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
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224—Amides; Imides carboxylic acid amides, imides
    • 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
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • 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
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • 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
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
    • 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
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
    • C10L1/2387—Polyoxyalkyleneamines (poly)oxyalkylene amines and derivatives thereof (substituted by a macromolecular group containing 30C)
    • 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
    • C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
    • 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
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
    • C10L1/1832—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom mono-hydroxy
    • 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
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/228—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles
    • C10L1/2283—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles containing one or more carbon to nitrogen double bonds, e.g. guanidine, hydrazone, semi-carbazone, azomethine

Definitions

  • the present invention relates to a composition comprising an aviation fuel and a deposit inhibiting compound.
  • turbine combustion fuel oils i.e. jet fuels such as JP-4, JP-5, JP-7, JP-8, Jet A, Jet A-1 and Jet B are ordinarily middle boiling distillates, such as kerosene or combinations of naphtha and kerosene.
  • military grade JP-4 for instance, is used in military aircraft and is a blend of naphtha and kerosene.
  • military grades JP-7 and JP-8 are primarily highly refined kerosenes, as are Jet A and Jet A-1, which are used for commercial aircraft.
  • Civil grades of jet fuel are defined in ASTM D1655, DefStan 91-91, and other similar specifications.
  • jet fuel are produced from a variety of sources including crude oil, oil sands, oil shales, Fischer Tropsch processes and gas to liquid processes.
  • Refinery processing includes fuels produced by straight distillation, sometimes processed by chemical sweetening, or hydrogen processing including hydrocracking operations, and may contain ⁇ 1 to 3000 ppm sulphur.
  • Turbine combustion fuel oils often contain additives such as antioxidants, metal deactivators, corrosion inhibitors and lubricity improvers. These additives are often necessary in these fuel oils to meet defined performance and storage requirements.
  • Turbine combustion fuel oils are used in integrated aircraft thermal management systems to cool aircraft subsystems and the engine lubricating oil.
  • the turbine combustion fuel oil is circulated in the airframe to match heat loads with available heat sink.
  • these thermal stresses raise bulk fuel temperatures to as high as 425° F. at the inlet to the mainburner fuel nozzles and above 500° F. inside the fuel nozzle passages.
  • skin temperatures up to 1100° F. are experienced. In future aircraft, these temperatures are expected to be 100° F. higher.
  • WO-A-99/25793 discloses compounds which are taught to be thermal stabilising additives for fuels comprising kerosene and jet fuels.
  • the compounds are oil soluble macromolecules and comprise a hydroxy-carboxylic acid functionality.
  • compounds of WO-A-99/25793 are of the formula
  • Y 1 and Y 2 are divalent bridging groups, which may be the same or different;
  • R 3 is hydrogen, a hydrocarbyl or a hetero-substituted hydrocarbyl group ; each of R 1 , R 2 and R 4 , which may be the same or different, is hydroxyl hydrogen, hydrocarbyl or hetero-substituted hydrocarbyl, with the proviso that at least one of R 1 , R 2 , R 4 is hydroxyl, and m+n is 4 to 20, m is 1-8 and n is at least 3.
  • U.S. Pat. No. 5,621,154 similarly relates to methods for cleaning and inhibiting deposit formation on jet engine surfaces such as fuel intake and combustion components during the combustion of turbine combustion fuel oils.
  • PATPA polyalkenylthiophosphonic acid
  • the derivatives of polyalkenylthiophosphonic acid are prepared in accordance with U.S. Pat. No. 3,281,359.
  • Compounds in accordance with the teaching of U.S. Pat. No. 5,621,154 have found some success and have been used by the United States Air Force (USAF) for the purposes disclosed.
  • the present invention alleviates the problems of the prior art.
  • the present invention provides a composition comprising (i) an aviation fuel; and (ii) a deposit inhibiting compound of the formula I
  • P is a polymeric hydrocarbyl group; in which Q is an optional ring system; in which R is a group selected from H and hydrocarbyl; wherein if R is a hydrocarbyl group it is free of a carboxylic acid group (—COOH); wherein Q together with R contains no greater than 2 nitrogens; and wherein when Q together with R contains 2 nitrogens each of the nitrogens is a member of a heterocyclic ring.
  • the present invention provides use of a deposit inhibiting compound as defined herein for
  • the present invention provides a method for inhibiting deposition formation in a fuel, preferably an aviation fuel, at an elevated temperature, the method comprising combining with the fuel a deposit inhibiting compound of the formula I
  • P is a polymeric hydrocarbyl group; in which Q is an optional ring system; in which R is a group selected from H and hydrocarbyl; wherein if R is a hydrocarbyl group it is free of a carboxylic acid group (—COOH); wherein Q together with R contains no greater than 2 nitrogens; and wherein when Q together with R contains 2 nitrogens each of the nitrogens is a member of a heterocyclic ring.
  • the compounds of the present invention act in aviation fuels to inhibit deposition of material from aviation fuels at elevated temperatures which, when present, may block filters and reduce the efficiency of an engine in which the fuel is combusted.
  • the present compounds which contain a limited number of nitrogens, do not de-activate the coalescing media in coalescers to the extent of compounds of, for example, U.S. Pat. No. 5,621,154 when present in a aviation fuel.
  • the present compounds provide effective compounds and compositions which do not require special handling, for use in aviation fuels in which water absorption is to be avoided, such as in jet fuels.
  • the tendency of detergents to deactivate a coalescer is commonly measured using the Micro Separometer rating (MSEP) test procedure.
  • the compounds of the present invention are the formula P-Q-R.
  • R is a selected from H and hydrocarbyl with the proviso that if R is a hydrocarbyl group it is free of a carboxylic acid group (—COOH).
  • Q together with R contains no greater than 2 nitrogens.
  • each of the nitrogens is a member of a heterocyclic ring.
  • the compounds of the invention are useful because limiting the number of basic nitrogens limits the polarity of the compounds.
  • the compounds thereby retain deposit inhibitory properties whilst have a reduced tendency (either alone or together with other co-additives such as corrosion inhibitors and lubricity improvers) to be absorbed onto the surface of coalescing media, for example fibreglass, in a coalescer.
  • the deposit inhibitory properties of the present compounds of the invention are particularly surprising as the art has previously taught that reduction of the number of nitrogens in a detergent reduces the detergency of that compound.
  • Q together with R contains no greater than 1 nitrogen.
  • R is a group selected from H and hydrocarbyl; wherein if R is a hydrocarbyl group it is free of a carboxylic acid group (—COOH).
  • hydrocarbyl group it is meant a group comprising at least C and H and may optionally comprise one or more other suitable substituents.
  • substituents may include halo-, alkoxy-, nitro-, a hydrocarbon group, an N-acyl group, a cyclic group etc.
  • a combination of substituents may form a cyclic group.
  • the hydrocarbyl group comprises more than one C then those carbons need not necessarily be linked to each other. For example, at least two of the carbons may be linked via a suitable element or group.
  • the hydrocarbyl group may contain hetero atoms. Suitable hetero atoms will be apparent to those skilled in the art and include, for instance, sulphur, nitrogen and oxygen.
  • the hydrocarbyl group is a hydrocarbon group.
  • hydrocarbon means any one of an alkyl group, an alkenyl group, an alkynyl group, an acyl group, which groups may be linear, branched or cyclic, or an aryl group.
  • the term hydrocarbon also includes those groups but wherein they have been optionally substituted. If the hydrocarbon is a branched structure having substituent(s) thereon, then the substitution may be on either the hydrocarbon backbone or on the branch; alternatively the substitutions may be on the hydrocarbon backbone and on the branch.
  • the hydrocarbon group contains from 1 to 10, preferably from 2 to 8, preferably 2 to 6, for example 2, 4 or 6 carbon atoms.
  • the hydrocarbon group is a straight chain.
  • R is a nitrogenous hydrocarbyl group.
  • nitrogenous hydrocarbyl group means a group comprising at least C, H and N and may optionally comprise one or more other suitable substituents. Examples of such substituents may include halo-, alkoxy-, an alkyl group, a cyclic group etc. In addition to the possibility of the substituents being a cyclic group, a combination of substituents may form a cyclic group. If the nitrogenous hydrocarbyl group comprises more than one C then those carbons need not necessarily be linked to each other. For example, at least two of the carbons may be linked via a suitable element or group. Thus, the nitrogenous hydrocarbyl group may contain hetero atoms. Suitable hetero atoms will be apparent to those skilled in the art and include, for instance, sulphur.
  • the nitrogenous hydrocarbyl group is a nitrogenous hydrocarbon group.
  • nitrogenous hydrocarbon group means a group containing only C, H and N (with the proviso of course that Q together with R contains no greater than 2 nitrogen) including primary, secondary and tertiary amines, which group may be linear, branched or cyclic.
  • nitrogenous hydrocarbon group also includes groups which have been optionally substituted. If the nitrogenous hydrocarbon group is a branched structure having substituent(s) thereon, then the substitution may be on either the hydrocarbon backbone or on the branch; alternatively the substitutions may be on the hydrocarbon backbone and on the branch.
  • the combined total of nitrogen and carbon atoms in the nitrogenous hydrocarbon group is from 1 to 10, preferably from 2 to 8, preferably 2 to 6, for example 2, 4 or 6.
  • the nitrogenous hydrocarbon group is a straight chain.
  • R is a hydrocarbyl group it is free of a hydroxyl group (—OH).
  • Q is an optional ring system. In one aspect the optional ring system Q is present.
  • Q is substituted.
  • Q is substituted with one or more groups selected from ⁇ O and —OH.
  • Q is an aromatic ring.
  • Q has from 4 to 10 members, preferably from 4 to 6 members, preferably 5 or 6 members.
  • Q may be heterocyclic ring or may contain only carbon.
  • the ring may be a hydrocarbyl ring.
  • hydrocarbyl ring it is meant a cyclic group comprising at least C and H and may optionally comprise one or more other suitable ring members. Suitable ring members will be apparent to those skilled in the art and include, for instance, sulphur, and nitrogen.
  • Q is a carbon ring or a heterocyclic ring containing only carbon and one nitrogen.
  • Q is selected from a ring system of the formula
  • Z is C or N and n is an integer from 1 to 5.
  • Q is selected from a ring system of the formula
  • Q contains an imide group, namely a group of the formula
  • Q is a ring system of the formula
  • Q is a hydrocarbon ring substituted with at least one alcohol group.
  • the hydrocarbon ring may be aromatic and in a preferred aspect is a six membered aromatic ring.
  • Q is a ring system of the formula
  • Q together with R is a Mannich group or is derived from or derivable from a Mannich reaction.
  • the ring Q contains a nitrogen
  • group R is attached to ring Q via the nitrogen.
  • the nitrogen of group Q may be substituted by group R.
  • P may be a C 10 -C 200 hydrocarbyl group, preferably a C 10 -C 200 hydrocarbon group.
  • P is preferably a C 30 -C 80 group.
  • P is a branched or straight chain alkyl group. In one aspect P is a branched alkyl group.
  • P is a polyalkenyl group.
  • the polyalkenyl is a C 2 to C 6 alkenyl group, more preferably a C 4 alkenyl group.
  • P is polyisobutene (PIB).
  • PlBs and so-called “high-reactivity” PlBs are suitable for use in the invention.
  • High reactivity in this context is defined as a PIB wherein at least 50%, preferably 70% or more, of the terminal olefinic double bonds are of the vinylidene type, for example the GLISSOPAL compounds available from BASF.
  • P has a molecular weight of 200 to 2500, for example approximately 2300, including from 1000 to 2500, from 1500 to 2500, from 2000 to 2500, from 200 to 2000, and from 700 to 1300.
  • P is polyisobutene having a molecular weight of from 1000 to 2500, from 1500 to 2500, or from 2000 to 2500.
  • the deposit inhibiting compound is selected from compounds of the formulae
  • PIB is polyisobutene.
  • PIB is polyisobutene having a molecular weight of from 1000 to 2500, from 1500 to 2500, or from 2000 to 2500.
  • the deposit inhibiting compound may be present in the composition in amount of at least 1 ppm or at least 5 ppm, such as 1 to 1000, 5 to 1000 for example 5 to 500, 5 to 200 or 10 to 100 ppm based on the weight of the composition e.g. the fuel composition.
  • the additive may be mixed with the jet or other fuel composition in the form of a concentrate in solution, e.g. in an aliphatic aromatic hydrocarbon in 20-80% w/w solution, or it may be added as such to give a solution in the fuel.
  • the composition can comprise jet fuel.
  • the composition can comprise kerosene, in particular in jet fuel.
  • the main component of the jet fuel itself is usually a middle boiling distillate boiling point in the range 150-300° C. at atmospheric pressure and the fuel is usually kerosene which may be mixed with gasoline (naphtha) and optionally light petroleum distillate as in mixtures of gasoline and kerosene.
  • the jet fuel may comprise mixtures of gasoline and light petroleum distillate, e.g. in weight amounts of 20-80:80-20 such as 50-75:50-25 which weight amounts may also be used for mixtures of gasoline and kerosene.
  • the jet fuels for military use are designated JP-4 to 8 e.g.
  • JP-4 as 65% gasoline/35% light petroleum distillate (according to US Mil. Spec. (MIL 5624G)), JP-5, similar to JP-4 but of higher flash point, JP-7, a high flash point special kerosene for advanced supersonic aircraft and JP-8, a kerosene similar to Jet Al (according to MIL 83133C).
  • Jet fuel for civilian use is usually a kerosene type fuel and designated Jet A or Jet AI.
  • the jet fuel may have a boiling point of 66-343° C. or 66-316° C. (150-650° F. e.g. 150-600° F.), initial boiling point of 149-221° C., e.g. 204 C.
  • Jet fuel for turbojet use may boil at 93-260° C. (200-500° F.) (ASTM D1655-006). Further details on aviation fuels may be obtained from “Handbook of Aviation Fuel Properties”, Co-ordinating Research Council Inc., CRC Report No. 530 (Society of Automotive Engineers Inc., Warrendale, Pa., USA, 1983) and on US military fuels, from “Military Specification for Aviation Turbine Fuels”, MIL-T-5624P.
  • the jet fuel may be the straight run kerosene optionally with added gasoline (naphtha), but frequently has been purified to reduce its content of components contributing to or encouraging formation of coloured products and/or precipitates.
  • the fuels may be purified to reduce their mercaptan content e.g. Merox fuels and copper sweetened fuels or to reduce their sulphur content e.g. hydrogen treated fuels or Merifined fuels.
  • Merox fuels are made by oxidation of the mercaptans and have a low mercaptan S content (e.g. less than 0.005% wt S) such as 0.0001-0.005% but a higher disulphide S content (e.g. at most 0.4% or at most 0.3% wt S such as 0.05-0.25 e.g. 0.1-2%); their aromatic (e.g.
  • Hydrogen processed jet fuels are ones in which the original fuel has been hydrogenated to remove at least some of sulphur compounds e.g. thiols and under severe conditions to saturate the aromatics and olefins; hydrofined jet fuels have very low sulphur contents (e.g. less than 0.01% S by weight).
  • Merifined fuels are fuels that have been extracted with an organic extractant to reduce or remove their contents of sulphur compounds and/or phenols.
  • the jet fuel may also contain metals, either following contact with metal pipes or carried over from the crude oil, oil sands, shale oil or other sources; examples of such metals are copper, nickel, iron and chromium usually in amounts of less than 1 ppm e.g. each in 10-150 ppb amounts. Merox, straight run and hydrofined fuels are preferred and may be used in JP-4-8 jet fuels.
  • the fuel comprising kerosene may also be a fuel for combustion especially for non motive purposes, e.g. power generation, steam generation, and heating, especially for use in buildings and for cooking, e.g. as described above.
  • the fuel is particularly suitable for the devices e.g. boilers and slow cookers as described above in which there is localised preheating of the fuel before it is combusted.
  • Such fuels are known as burning kerosene and may have the same physical properties as the kerosene based jet fuels described above, e.g. straight run kerosene, or kerosene modified to reduce its content of at least one of aromatics, olefins and sulphur compounds, as described above.
  • the fuel may also contain metals as described above.
  • the fuel compositions of the invention contains the deposit inhibiting compound and may also contain at least one conventional additive e.g. for jet fuels or burning fuels such as an antioxidant, corrosion inhibitor, lubricity improvers, metal deactivators (MDA), leak detection additives, “special purpose” additives such as drag reducing agents, anti-icing additives and static dissipators such as Stadis®, especially in amounts each of 1-2000 ppm.
  • the deposit inhibiting compounds may be present in the composition especially with a dispersant; the dispersant is in particular one known for use in fuels e.g. automotive burning or aviation fuels.
  • Such dispersants usually have a polymeric carbon backbone with pendant groups containing nitrogen, which may be primary, secondary or tertiary, in cyclic or acyclic systems, and especially in amine, amide or imide groupings, in particular cyclic imide groups.
  • the dispersants may also contain 1-5 polymer chains which are bridged by the nitrogen containing groups. Examples of such dispersants are the reaction products of polyisobutene succinic anhydride (PIBSA) and polyamines.
  • PIBSA polyisobutene succinic anhydride
  • Such dispersants are known compounds for dispersing particles in non aqueous systems e.g. hydrocarbon systems.
  • the weight ratio of deposit inhibiting compound to dispersant may be 99:1 to 10:90, especially 30:70 to 70:30.
  • the additives and the fuel composition are preferably substantially ashless.
  • the use or method of the present invention is typically performed when the fuel or fuel composition is at a temperature of no greater than 1100° F.
  • the fuel or fuel composition is typically at a temperature of 325 to 425° F. during use.
  • the use or method of the present invention is preferably performed when the fuel or fuel composition is at a temperature of from 100 to 335° C.
  • the present invention may be applicable to a broad range of fuels, not only aviation fuels.
  • a composition comprising (i) a fuel; and (ii) a deposit inhibiting compound of the formula I P-Q-R (I), in which P is a polymeric hydrocarbyl group, in which Q is an optional ring system; in which R is a group selected from H and hydrocarbyl; wherein if R is a hydrocarbyl group it is free of a carboxylic acid group (—COOH); wherein Q together with R contains no greater than 2 nitrogens; and wherein when Q together with R contains 2 nitrogens each of the nitrogens is a member of a heterocyclic ring.
  • FIG. 1 shows compounds not in accordance with the present invention.
  • FIG. 2 shows compounds in accordance with the present invention.
  • FIG. 3 shows ICOT apparatus.
  • FIG. 4 shows HLPS apparatus.
  • Scope The ICOT is used to investigate the effectiveness of additives in jet fuel. This is carried out by stressing base and additized fuels at constant temperature with a controlled volume of air flowing though the sample. On cooling the fuels are filtered, the thermal stability measured by the weight of solid on a filter.
  • Apparatus See ASTM Method D4871-88 for description of apparatus.
  • the filter to be used is a 0.7 to 1 ⁇ m glass micro-fibre filter.
  • a furnace anneals the glass inlet tubes and the test cell at 600° C. Filtration is done under suction using an appropriate funnel.
  • Base fuels fuels not containing additives
  • Additized fuels base fuels that have been treated with additive package containing
  • Preparation Clean glassware must be used for each experiment.
  • the cleaning of the glass inlet tubes and the test cells is done by annealing in a furnace at 600° C. then allowing cooling in air.
  • the condensers are washed out with acetone with a small brush and wiped to ensure that no fuel residues are present, then allowed to dry in air.
  • Sites 1-5 are used for test fuel samples. Place 100 mls of test fuel in each cell by carefully releasing the condenser and inserting a glass funnel.
  • test cell For each sample pre-weigh a 0.7-1 ⁇ m glass micro-fibre filter. Place the test cells in a ultrasonic bath for 3 minutes to release any deposit adhered to the sides of the cell, then filter the fuel under vacuum. Rinse the test cell rinsed with heptane or 2-2-4 trimethylpentane and also filter..
  • HLPS is a self-contained testing apparatus designed to test the thermal properties of base and additised jet fuels. The test involves the flow of the test fuel over a heated test surface (@ 335° C.) under high pressure (500 psi).
  • FIG. 4 The basic principles of the HLPS are shown in FIG. 4. As shown in FIG. 4, 1 litre of test fuel is pressurised in a stainless steel reservoir to 500 psi. The fuel is then pumped via a pre-filter over a heated test section (@335° C). As deposition occurs on both the tube and in the fuel bulk the bulk deposit is measured as a filter drop change across a 17 micron filter. A pressure transducer cell measures the rate of pressure drop (in mmHg min-1). Finally the spent fuel is returned to the top of the reservoir, separated by an appropriate seal.
  • Apparatus is a modular version of the equipment set up as defined in ASTM D-3241.
  • the test section must be of stainless steel 316 and free from grease.
  • the filter to be used must be of 17 micron mesh as supplied by Alcor.
  • Base fuels are fuels free of additives
  • Additized fuels are base fuels containing 100 mg/l (active ingredient) of detergent/dispersant alone.
  • test fuel transfers to a 2 litre beaker. Aerate using the glass bubbler attachment for a minimum of 6 minutes. Test run must be initiated within 1 hour of aeration.
  • HEATER TUBE TEMP. CONTROL is set to 335 deg. C. Switch on HEATER. Red indicator light will come on. Needle will then rise to the vertical. Heater power is controlled by using the POWER CONTROL dial. A typical setting for this procedure is 82 +/ ⁇ 10 volts.
  • Filter blockage Record the change in differential pressure during the run. Results are quoted in mmHg min-1, e.g. 300/45, 0/300. The first figure is the change in differential pressure in mmHg the latter the time in minutes
  • Carbon deposit weight Record the value according to method no. JP8003/01 in ⁇ gcm ⁇ 2.
  • MSEP testing is carried out in a fuel dosed with
  • the dosed fuel makes up a standard military basefuel package for purposes of MSEP evaluation.
  • the detergent/dispersant has been added to this at treat rate of 50 mg/l (active ingredient).
  • the tests are carried out using a modified MSEP cell supplied as MCELL by Emcee Electronics Inc.
  • the MSEP test was otherwise performed in accordance with ASTM Designation D3948-93. Details of this D3948-93 are given in Appendix I.
  • PIB chloride (153 g, chlorine content 4.89% m/m) was placed in a stirred reactor with butylamine (61.6 g) and Shellsol (50 ml. The reactor contents were heated to reflux for 19.5 hours. Crystalline solid could be seen in the solution as the reaction proceeded. The reaction was allowed to cool and an excess of aqueous sodium carbonate was mixed with the reactor contents. After separation the organics were washed with water and dried over sodium sulphate. The unreacted butylamine was removed under reduced pressure leaving the 190 g product plus solvent.
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US8628594B1 (en) 2009-12-01 2014-01-14 George W. Braly High octane unleaded aviation fuel
US10260016B2 (en) 2009-12-01 2019-04-16 George W. Braly High octane unleaded aviation gasoline
US10364399B2 (en) 2017-08-28 2019-07-30 General Aviation Modifications, Inc. High octane unleaded aviation fuel
US10377959B2 (en) 2017-08-28 2019-08-13 General Aviation Modifications, Inc. High octane unleaded aviation fuel
US10550347B2 (en) 2009-12-01 2020-02-04 General Aviation Modifications, Inc. High octane unleaded aviation gasoline
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US8628594B1 (en) 2009-12-01 2014-01-14 George W. Braly High octane unleaded aviation fuel
US10260016B2 (en) 2009-12-01 2019-04-16 George W. Braly High octane unleaded aviation gasoline
US10550347B2 (en) 2009-12-01 2020-02-04 General Aviation Modifications, Inc. High octane unleaded aviation gasoline
US11098259B2 (en) 2009-12-01 2021-08-24 General Aviation Modifications, Inc. High octane unleaded aviation gasoline
US11674100B2 (en) 2009-12-01 2023-06-13 General Aviation Modifications, Inc. High octane unleaded aviation gasoline
US8324437B2 (en) 2010-07-28 2012-12-04 Chevron U.S.A. Inc. High octane aviation fuel composition
US20200102514A1 (en) * 2017-03-30 2020-04-02 Palox Limited Method for improving the emulsification performance of nonionic alkoxylated surfactants
US11124722B2 (en) * 2017-03-30 2021-09-21 Palox Limited Method for improving the emulsification performance of nonionic alkoxylated surfactants
US10364399B2 (en) 2017-08-28 2019-07-30 General Aviation Modifications, Inc. High octane unleaded aviation fuel
US10377959B2 (en) 2017-08-28 2019-08-13 General Aviation Modifications, Inc. High octane unleaded aviation fuel

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