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US20030150153A1 - Method - Google Patents

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Publication number
US20030150153A1
US20030150153A1 US10/286,530 US28653002A US2003150153A1 US 20030150153 A1 US20030150153 A1 US 20030150153A1 US 28653002 A US28653002 A US 28653002A US 2003150153 A1 US2003150153 A1 US 2003150153A1
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Prior art keywords
invention according
fuel
composition
acid
antioxidant
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US10/286,530
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English (en)
Inventor
Cyrus Henry
David Pinch
Andrea Sneddon
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Innospec Ltd
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Individual
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Priority claimed from GB0126396A external-priority patent/GB0126396D0/en
Priority claimed from GB0204114A external-priority patent/GB0204114D0/en
Application filed by Individual filed Critical Individual
Priority to US10/286,530 priority Critical patent/US20030150153A1/en
Assigned to THE ASSOCIATED OCTEL COMPANY LIMITED reassignment THE ASSOCIATED OCTEL COMPANY LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HENRY, CYRUS PERSHING, JR., PINCH, DAVID LEONARD, SNEDDON, ANDREA
Publication of US20030150153A1 publication Critical patent/US20030150153A1/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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • 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
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    • 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
    • C10L1/1855—Cyclic ethers, e.g. epoxides, lactides, lactones
    • C—CHEMISTRY; METALLURGY
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    • C10L1/00—Liquid carbonaceous fuels
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    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10L1/223—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • 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
    • C—CHEMISTRY; METALLURGY
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    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—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
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    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
    • C10L1/2406—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides
    • C10L1/2412—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides sulfur bond to an aromatic radical
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
    • C10L1/2425—Thiocarbonic acids and derivatives thereof, e.g. xanthates; Thiocarbamic acids or derivatives thereof, e.g. dithio-carbamates; Thiurams
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/26—Organic compounds containing phosphorus
    • C10L1/2608—Organic compounds containing phosphorus containing a phosphorus-carbon bond
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/26—Organic compounds containing phosphorus
    • C10L1/2608—Organic compounds containing phosphorus containing a phosphorus-carbon bond
    • C10L1/2616—Organic compounds containing phosphorus containing a phosphorus-carbon bond sulfur 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/26—Organic compounds containing phosphorus
    • C10L1/2633—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond)
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/26—Organic compounds containing phosphorus
    • C10L1/2633—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond)
    • C10L1/2641—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond) oxygen bonds only
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/26—Organic compounds containing phosphorus
    • C10L1/2633—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond)
    • C10L1/265—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond) oxygen and/or sulfur bonds

Definitions

  • the present invention relates to a composition comprising a high temperature antioxidant 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.
  • hydrocarbon jet fuels are known to be subject to deterioration when in contact with oxygen, either on standing in air or during pre-combustion heating. Such deterioration is thought to be due to the presence in the fuel of constituents which undergo oxidative changes resulting in the formation of non-volatile resinous substances.
  • the high temperatures and oxygen-rich atmospheres in aircraft and engine fuel system components encourage the degradation of the fuel resulting in particulate and deposit formation.
  • GB 2261441 teaches a fuel composition in the gasoline boiling range containing a polyoxyalkylene compound and the reaction product of a polyamine and a hydrocarbyl succinic acylating agent.
  • U.S. Pat. No. 5,601,624 discloses a fuel composition comprising a fuel and a minor amount of a multifunctional additive such as a dispersant, corrosion inhibitor or antioxidant.
  • the additive is the reaction product of an oxygenated amine with a dicarbonyl compound and a hydrocarbyl or hydrocarbylene amine. e.g. a polyetheramine, glyoxal and a succinimide.
  • U.S. Pat. No. 5,990,056 relates to a lubricant composition
  • a lubricant composition comprising an organo substituted benzophenone and at least one co-additive such as a lubricant antioxidant, a lubricant dispersant, or an antiwear additive.
  • the compound is thought to act as a lubricant base or blend stock, a solubility enhancer or a deposit reducing agent.
  • GB 923190 teaches a synergistic antioxidant mix for use in organic material.
  • the mix comprises a phosphite ester and a methylene bis phenol.
  • the use in jet fuel, kerosene, and fuel oil is disclosed.
  • GB 791526 discloses dimethyl-(phenyl)-phosphates (e.g. dimethyl-(tolyl)-phosphate).
  • fuels including jet fuels often contain additives such as antioxidants, deposit inhibiting compounds, metal deactivators, corrosion inhibitors and lubricity improvers. It would be apparent to one skilled in the art that synergistic combinations of any of these additives would be desirable.
  • Antioxidant additives are used not only in fuel but also in a range of other substances such as lubricants, plastics and food products.
  • the present invention alleviates the problems of the prior art.
  • the present invention relates to the provision of combinations, in particular synergistic combinations, of antioxidants and deposit inhibiting compounds.
  • the present invention provides a method for inhibiting deposit formation in a fuel at a temperature of from 100 to 335° C., the method comprising combining with the fuel a composition comprising: (i) high temperature antioxidant; and (ii) a deposit inhibiting compound.
  • high temperature antioxidant it is meant an antioxidant which may prevent oxidation in a fuel at high temperature.
  • an antioxidant which provides improved antioxidant performance when measured in accordance with the High Temperature Antioxidant Protocol below.
  • the present invention provides a composition comprising (i) a phosphorus-containing antioxidant; and (ii) a deposit inhibiting compound
  • the present invention provides a fuel composition
  • a fuel composition comprising (a) a fuel (b) a composition as defined herein.
  • the present invention provides a use of a composition as defined herein for
  • the present invention provides a composition comprising (i) a phosphorus-containing antioxidant; and (ii) a deposit inhibiting compound, in an amount or a ratio to produce an antioxidant and/or deposit inhibitory synergistic effect.
  • a phosphorus-containing antioxidant such as di-dodecyl hydrogen phosphonate
  • a deposit inhibiting compound such as 2300 ButA Mannich
  • the oxidation products or deposited material may block filters and reduce the efficiency of an engine in which the fuel is combusted.
  • the combination of products which form the present composition act in a synergistic manner to prevent or inhibit oxidation and/or deposition of material.
  • compositions of the present invention an anti-oxidant and/or deposit inhibitory effect may be observed, for example by study using Hot Liquid Process Simulator (HLPS).
  • HLPS Hot Liquid Process Simulator
  • the anti-oxidant and/or deposit inhibitory effect is greater than one would expect from the anti-oxidant and/or deposit inhibitory effect of each of the composition components, i.e. the combination of components provides a synergistic effect.
  • the present invention provides a method for inhibiting deposit formation in a fuel at a temperature of from 100 to 335° C., the method comprising combining with the fuel a composition comprising: (i) high temperature antioxidant; and (ii) a deposit inhibiting compound.
  • the high temperature antioxidant of the present invention is a phosphorus-containing antioxidant.
  • the phosphorus-containing antioxidant is an organophosphorus-containing antioxidant.
  • organophosphorus-containing anti-oxidant it is meant a compound comprising at least P and C and may optionally comprise one or more other suitable atoms. Examples of such atoms may include hydrogen, sulphur and oxygen.
  • organophosphorus-containing anti-oxidant it is meant a compound containing a C—P bond and/or a C—O—P bond and/or a C—S—P bond.
  • the phosphorus-containing antioxidant is or is derived from an organophosphorus acid.
  • the organophosphorus acid is selected from phosphorus acid, phosphonous acid, phosphinous acid, phosphoric acid, phosphonic acid or phosphinic acid.
  • the phosphorus-containing antioxidant is or is derived from an ester of an organophosphorus acid.
  • the organophosphorus acid is selected from phosphorus acid, phosphonous acid, phosphinous acid, phosphoric acid, phosphonic acid or phosphinic acid.
  • the phosphorus-containing antioxidant is an ester of an organophosphorus acid. More preferably the phosphorus-containing antioxidant is an ester of an organophosphorus acid selected from phosphorus acid, phosphonous acid, phosphinous acid, phosphoric acid, phosphonic acid or phosphinic acid.
  • the phosphorus-containing antioxidant is or is an ester of a phosphonic acid.
  • the phosphorus-containing antioxidant is an ester of a phosphonic acid.
  • the phosphorus-containing antioxidant contains a trivalent or pentavalent phosphorus.
  • the phosphorus-containing antioxidant is a compound of Formula l:
  • R 1 , R 2 and R 3 are independently selected from H and hydrocarbyl; and X, Y, and Z are independently selected from O and S.
  • the phosphorus-containing antioxidant is a compound of Formula II:
  • R 1 , R 2 and R 3 are independently selected from H and hydrocarbyl; and X, Y, and Z are independently selected from O and S.
  • 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.
  • At least one of X, Y or Z is O.
  • At least one of Y and Z is O.
  • X is S or O
  • Y is O
  • Z is O.
  • the antioxidant of the present invention is of the formula
  • each of X, Y and Z is O.
  • the antioxidant of the present invention is of the formula
  • R 1 , R 2 and R 3 are as defined above.
  • At least one of X, Y or Z is O and wherein at least one of X, Y or Z is S.
  • the antioxidant of the present invention is of the formula
  • R 1 , R 2 and R 3 are independently selected from H and hydrocarbyl.
  • R 1 is selected from H and hydrocarbon.
  • R 1 is selected from H and C 1-30 hydrocarbyl, such as C 1-20 hydrocarbyl, C 1-15 hydrocarbyl, C 1-10 hydrocarbyl, C 1 , C 2 , C 3 , or C 4 hydrocarbyl.
  • R 1 is selected from H and C 1-30 hydrocarbon, such as C 1-20 hydrocarbon, C 1-15 hydrocarbon, C 1-10 hydrocarbon, C 1 , C 2 , C 3 , or C 4 hydrocarbon.
  • R 1 is selected from H and C 1-30 alkyl, such as C 1-20 alkyl, C 1-15 alkyl, C 1-10 alkyl, C 1 , C 2 , C 3 , or C 4 alkyl.
  • R 1 is selected from H and C 1-10 alkyl, for example C 1 , C 2 , C 3 , or C 4 alkyl.
  • R 1 is H.
  • R 1 is selected from
  • H and C 1-100 hydrocarbyl such as C 1-50 hydrocarbyl, C 1-30 hydrocarbyl, C 1-25 hydrocarbyl, C 1-20 hydrocarbyl, C 1-15 hydrocarbyl, C 1-12 hydrocarbyl, C 5-25 hydrocarbyl, C 8-20 hydrocarbyl, C 10-15 hydrocarbyl, C 10 , C 11 , C 12 , C 13 , or C 14 hydrocarbyl.
  • H and C 1-100 hydrocarbon such as C 1-50 hydrocarbon, C 1-30 hydrocarbon, C 1-25 hydrocarbon, C 1-20 hydrocarbon, C 1-15 hydrocarbon, C 1-12 hydrocarbon, C 5-25 hydrocarbon, C 8-20 hydrocarbon, C 10-15 hydrocarbon, C 10 , C 11 , C 12 , C 13 , or C 14 hydrocarbon.
  • H and C 1-100 alkyl such as C 1-50 alkyl, C 1-30 alkyl, C 1-25 alkyl, C 1-20 alkyl, C 1-15 alkyl, C 1-12 alkyl, C 5-25 alkyl, C 8-20 alkyl, C 10-15 alkyl, C 10 , C 11 , C 12 , C 13 , or C 14 alkyl.
  • H and C 1-100 straight chain alkyl such as C 1-50 alkyl, C 1-30 alkyl, C 1-25 alkyl, C 1-20 alkyl, C 1-15 alkyl, C 1-12 alkyl, C 5-25 alkyl, C 8-20 alkyl, C 10-15 alkyl, C 10 , C 11 , C 12 , C 13 , or C 14 alkyl.
  • R 2 and R 3 are independently selected from H and hydrocarbon groups.
  • R 2 and R 3 are independently selected from H and C 1-100 hydrocarbyl, such as C 1-50 hydrocarbyl, C 1-30 hydrocarbyl, C 1-25 hydrocarbyl, C 1-20 hydrocarbyl, C 1-15 hydrocarbyl, C 1-12 hydrocarbyl, C 5-25 hydrocarbyl, C 8-20 hydrocarbyl, C 10-15 hydrocarbyl, C 10 , C 11 , C 12 , C 13 , or C 14 hydrocarbyl.
  • R 2 and R 3 are independently selected from H and C 1-100 hydrocarbon, such as C 1-50 hydrocarbon, C 1-30 hydrocarbon, C 1-25 hydrocarbon, C 1-20 hydrocarbon, C 1-15 hydrocarbon, C 1-12 hydrocarbon, C 5-25 hydrocarbon, C 8-20 hydrocarbon, C 10-15 hydrocarbon, C 10 , C 11 , C 12 , C 13 , or C 14 hydrocarbon.
  • R 2 and R 3 are independently selected from H and C 1-100 alkyl, such as C 1-50 alkyl, C 1-30 alkyl, C 1-25 alkyl, C 1-20 alkyl, C 1-15 alkyl, C 1-12 alkyl, C 5-25 alkyl, C 8-20 alkyl, C 10-15 alkyl, C 10 , C 11 , C 12 , C 13 , or C 14 alkyl.
  • R 2 and R 3 are independently selected from H and C 1-100 straight chain alkyl, such as C 1-50 alkyl, C 1-30 alkyl, C 1-25 alkyl, C 1-20 alkyl, C 1-15 alkyl, C 1-12 alkyl, C 5-25 alkyl, C 8-20 alkyl, C 10-15 alkyl, C 10 , C 11 , C 12 , C 13 , or C 14 alkyl.
  • the antioxidant is of the formula
  • n and m are independently selected from 1 to 15, preferably 5 to 15, preferably 7 to 13, preferably 8 to 12, preferably 9, 10 or 11.
  • the antioxidant is of the formula
  • This compound is commonly known as di-dodecyl hydrogen phosphonate.
  • the antioxidant is of the formula
  • This compound is commonly known as tridodecylphosphite.
  • the deposit inhibiting compound is of Formula II
  • Polymer is a polymeric hydrocarbyl group; wherein Q is an optional ring system; and wherein R is a group selected from H and hydrocarbyl.
  • R is a hydrocarbyl group it is free of a carboxylic acid group (—COOH).
  • R is a hydrocarbyl group it is free of a hydroxyl group (—OH).
  • R is selected from H and a nitrogenous hydrocarbyl group.
  • 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.
  • 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 4 to 10 members, preferably 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 carbon and one nitrogen.
  • Q is selected from a ring system of the formula
  • A is C or N and n is an integer from 1 to 5.
  • Q is selected from a ring system of the formula
  • A is C or N, i.e. n is 1 or 2.
  • 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.
  • Q together with R contains no greater than 2 nitrogens.
  • Q together with R contains only 2 nitrogens and wherein each of the nitrogens is a member of a heterocyclic ring.
  • Q together with R contains no greater than 1 nitrogen.
  • Q together with R contains no greater than 1 basic nitrogen.
  • Polymer is a hydrocarbyl group having from 10 to 200 carbons.
  • Polymer is a branched or straight chain alkyl group, preferably a branched alkyl group.
  • Preferably Polymer has a molecular weight of from 700 to 2500, preferably 1000 to 2300, preferably approximately 1000 or approximately 2300.
  • Polymer is polyisobutene (PIB).
  • PIB polyisobutene
  • Conventional PIBs and so-called “high-reactivity” PIBs 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.
  • Polymer is polyisobutene having a molecular weight of from 700 to 2500, preferably 1000 to 2300, preferably approximately 1000 or approximately 2300.
  • the deposit inhibiting compound is selected from compounds of the formulae
  • PIB polyisobutene
  • the deposit inhibiting compound is selected from compounds of the formulae
  • PIB polyisobutene having a molecular weight of approximately 2300
  • PIB polyisobutene having a molecular weight of approximately 1000
  • PIB polyisobutene having a molecular weight of approximately 1000
  • the deposit inhibiting compound is provided in the composition to provide a fuel treat rate of 1-500 mg/l active concentration, preferably 50-300 mg/l, preferably 50-150 mg/l, preferably 75-125 mg/l, preferably approximately 100 mg/l.
  • the antioxidant is provided in the composition to provide a fuel treat rate of 1-100 mg/l active concentration, preferably 5-80 mg/l, preferably 5-50 mg/l preferably 5-20 mg/l , preferably 7-15 mg/l, preferably 10-13 mg/l.
  • the composition further comprises a metal deactivator.
  • a metal deactivator is N,N′-disalicylidene 1,2-propanediamine or N,N′-disalicylidene 1,2-cyclohexyldiamine.
  • the metal deactivator is provided in the composition to provide a fuel treat rate of 1-50 mg/l active concentration, preferably 1-30 mg/l, preferably 1-20 mg/l, preferably 1-10 mg/l, preferably 1-5 mg/l, preferably approximately 2 mg/l.
  • the composition further comprises a further antioxidant.
  • a possible further antioxidant is BHT (2,6-di-t-butyl-4-methyl phenol) or other aviation approved hindered phenol antioxidants.
  • the additional antioxidants may be added in order to protect fuel from the build up peroxides on storage.
  • the further antioxidant is provided in the composition to provide a fuel treat rate 0-100 mg/l, preferably 5-80 mg/l, preferably 10-50 mg/l, preferably 10-30 mg/l, preferably approximately 25 mg/l.
  • the present invention provides a fuel composition
  • a fuel composition comprising (a) a fuel (b) a composition comprising (i) a phosphorus-containing antioxidant; and (ii) a deposit inhibiting compound
  • the fuel is an aviation turbine fuel.
  • the fuel is JP-8 aviation fuel.
  • the deposit inhibiting compound may be present in the composition in amount of at least 1 mg/l or at least 5 mg/l, such as 1 to 1000, 5 to 1000 for example 5 to 500, 5 to 200 or 10 to 100 mg/l active ingredient 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 AI (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 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 hydrogen processed 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 dissipaters such as Stadis®, especially in amounts each of 1-2000 ppm.
  • 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 dissipaters such as Stadis®, especially in amounts each of 1-2000 ppm.
  • 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.
  • FIG. 1 shows HLPS apparatus.
  • Scope 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. 1 The basic principles of the HLPS are shown in FIG. 1.
  • 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.).
  • a heated test section @335° C.
  • a pressure transducer cell measures the rate of pressure drop (in mmHg min-1).
  • 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
  • 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
  • a high temperature antioxidant candidate is formulated in a composition comprising the high temperature antioxidant candidate, 2300 ButA Mannich (a deposit inhibiting compound) and N,N′-disalicylidene 1,2-propanediamine (an MDA).
  • the composition is dosed into at least three test fuels at a treat rate for each fuel of
  • the currently approved stabiliser package SpecAid 8Q462 (available from Shell Aviation as AeroShell Performance Additive 101) is dosed into the same base fuels at a treat rate 256 mg/l for each fuel. Each dosed fuel is subjected to HPLS testing in accordance with the above Protocol.
  • the pressure drop recorded for the candidate composition in a given fuel is compared to pressure drop recorded for SpecAid 8Q462 in the same fuel.
  • a candidate is considered to “pass” if for each fuel the pressure drop recorded for the candidate composition is no greater than 2 mmHg more than the pressure drop recorded for SpecAid 8Q462.
  • the carbon deposit weight of each fuel containing the candidate composition and the carbon deposit weight of each fuel containing SpecAid 8Q462 is recorded.
  • the carbon deposit weight for the candidate composition is averaged across the number of fuels tested.
  • the carbon deposit weight for SpecAid 8Q462 is averaged across the number of fuels tested.
  • a candidate is considered to “pass” if the average carbon deposit weight for the candidate composition is less than, equal to or no greater than 10 mg more than the average carbon deposit weight for the SpecAid 8Q462.
  • a candidate which “passes” in respect of both pressure drop and carbon deposit weight constitutes a “high temperature antioxidant” within the scope of the present invention.
  • the at least three test fuels may be selected from Shell HT, POSF 3684 (USAF B), Phillips HT, Sunoco, Shell Merox, USAF A, BP Air Merox, Marathon HT, and Phillips Merox.
  • the candidate composition is dosed into POSF 3684 (USAF B), Phillips HT, Sunoco, Shell Merox, USAF A, BP Air Merox, and Phillips Merox.
  • the candidate composition is dosed into Shell HT, POSF 3684 (USAF B), Phillips HT, Sunoco, Shell Merox, USAF A, BP Air Merox, Marathon HT, and Phillips Merox.
  • 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.
  • HLPS testing was performed and data collected. Results given are surface carbon deposit weight ( ⁇ gcm ⁇ 2 ) and filter blockage, ⁇ P, (mmHg/min). A result of 0/300 means that no blockage has occurred over the 300 minutes of the test, a result of 300/101 means that the filter has completely blocked in 101 minutes.
  • antioxidants/antioxidant compositions were used in the Examples AO1 2,6-di-t-butyl-4-methyl phenol AO2 Octadecyl-3-(3′,5′-di-t-butyl-4′-hydroxyphenyl) propionate AO3 Methylene bis (dibutylthiocarbamate) AO4 2,2′thiodiethyl bis-(3,5-di-t-butyl-4-hydroxyphenyl) propionate AO5 commercially available alkylated phenol AO6 3,5-bis-(1,1-dimethyl-ethyl)-4-hydroxybenzenepropanoic ester of C 14-15 alcohol AO7 “synergistic blend of an aminic and a phenolic antioxidant” AO8 di-dodecyl hydrogen phosphonate AO9 SpecAid 8Q462 AO10 dioleyl hydrogenophosphite AO11 tridodecylphos
  • Shell HT POSF 3684 (USAF B) Carbon Carbon Composition ⁇ gcm ⁇ 2 ⁇ P ⁇ gcm ⁇ 2 ⁇ P Basefuel 39 300/230 125 300/45 Basefuel + detergent 38 0/300 90.5 12/300 Basefuel + MDA 62 0/300 24 300/101 Basefuel, detergent + MDA 39 0/300 29.5 5/300 Basefuel, detergent, MDA + AO1 (25 mg/l) 41.5 0/300 27 0/300 Basefuel, detergent, MDA + AO2 (60.3 mg/l) 18 0/300 32 1/300 Basefuel, detergent, MDA + AO3 (50 mg/l) 66 0/300 32 4/300 Basefuel, detergent, MDA + AO4 (45 mg/l) 60 0/300 34 0/300 Basefuel, detergent, MDA + AO5 (25 mg/l) 19 300/270 19 9/300 Basefuel, detergent, MDA + AO6 (60 mg/l) 47 6/300 32 6/300 Base
  • Example 1 The preferred anti-oxidant of Example 1, namely AO8, was combined with three different detergents. The results were compared against the fuel, MDA, detergent and anti-oxidant alone or in various combinations.
  • the HLPS data are given below.
  • HLPS results for package based on AO8 in different fuels are also given.
  • HPLS results for basefuel and SpecAid 8Q462 at a treat rate 256 mg/l are also given.

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WO2012009224A1 (fr) * 2010-07-16 2012-01-19 Petroleum Analyzer Company, Lp Auto-amorçage et rinçage d'un appareil permettant de déterminer la stabilité thermique de fluides
US8246244B2 (en) 2010-07-16 2012-08-21 Petroleum Analyzer Company Lp Containers used in determining the thermal stability of fuels
US8262283B2 (en) 2010-07-16 2012-09-11 Petroleum Analyzer Company, Lp Apparatus and method for determining the thermal stability of fluids
US9028675B2 (en) 2011-07-07 2015-05-12 Exxonmobil Research And Engineering Company Method for increasing thermal stability of a fuel composition using a solid phosphoric acid catalyst
US10081773B2 (en) 2011-07-12 2018-09-25 Total Marketing Services Additive compositions that improve the stability and the engine performances of diesel fuels

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CN1953956B (zh) * 2004-05-19 2010-12-22 通用电气公司 多烯基琥珀酰亚胺在丙烯酸制备中的用途
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US10081773B2 (en) 2011-07-12 2018-09-25 Total Marketing Services Additive compositions that improve the stability and the engine performances of diesel fuels
US10538714B2 (en) 2011-07-12 2020-01-21 Total Marketing Services Additive compositions that improve the stability and the engine performances of diesel fuels

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