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 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
  • C10L1/232—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 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
• • 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
  • C10L1/22—Organic compounds containing nitrogen
• • 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
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/221—Organic compounds containing nitrogen compounds of uncertain formula; reaction products where mixtures of compounds are obtained
• • 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
  • C10L1/22—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
  • C10L1/2493—Organic compounds containing sulfur, selenium and/or tellurium compounds of uncertain formula; reactions of organic compounds (hydrocarbons, acids, esters) with sulfur or sulfur containing 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
  • C10L1/26—Organic compounds containing phosphorus
  • C10L1/2691—Compounds of uncertain formula; reaction of organic compounds (hydrocarbons acids, esters) with Px Sy, Px Sy Halz or sulfur and phosphorus containing 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
  • C10L1/30—Organic compounds compounds not mentioned before (complexes)
  • C10L1/301—Organic compounds compounds not mentioned before (complexes) derived from metals
  • C10L1/303—Organic compounds compounds not mentioned before (complexes) derived from metals boron 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
  • C10L10/00—Use of additives to fuels or fires for particular purposes
  • C10L10/02—Use of additives to fuels or fires for particular purposes for reducing smoke development
• • 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
  • C10L10/12—Use of additives to fuels or fires for particular purposes for improving the cetane number
• • 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
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/23—Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites
  • C10L1/231—Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites nitro compounds; nitrates; nitrites
• • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
  • F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
  • F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
  • F02B3/00—Engines characterised by air compression and subsequent fuel addition
  • F02B3/06—Engines characterised by air compression and subsequent fuel addition with compression ignition

Definitions

• This invention relates to fuel oil compositions, and to additives for use in such compositions. More
• the present invention is based on the observation that certain dispersants, if desired in combination with cetane enhancers, when incorporated in a diesel, heating, or jet fuel, reduce the emission of particulates.
• the present invention provides the use of an ashless oil soluble macrocyclic polyamine dispersant to reduce particulate emission in the combustion of a fuel oil. More
• the present invention accordingly provides the use, as a particulate-reducing additive for, and the use in reducing particulate emission in the combustion of, a fuel oil of an oil soluble compound of the formula:
• R 1 , R 2 and R 3 may be the same or different and are independently hydrogen or a hydrocarbyl substituent having from 2 to 600 carbon atoms, or a keto, halo, hydroxy, nitro, cyano, or alkoxy derivative thereof, provided that at least one of R 1 , R 2 and R 3 is a hydrocarbyl substituent having from 2 to 600 carbon atoms or said derivative thereof, or wherein R 1 and R 2 together form a hydrocarbylene substituent having 4 to 600 carbon atoms or a keto, halo, hydroxy, nitro, cyano or alkoxy derivative thereof, provided that R 1 and R 2 together with the carbon atom which forms the C-R 1 bond with R 1 and the nitrogen atom which forms the N-R 2 bond with R 2 form a ring having at least 5 members, wherein Z represents
• each R 10 which may be the same or different, represents an alkylene group having from 1 to 5 carbon atoms in its chain
• each R 11 which may be the same or different, represents a hydrogen atom or a hydrocarbyl group
• c is from 0 to 6
• d is from 1 to 4
• e is from 1 to 4 , provided that d + e is at most 5
• each R 4 is independently H or an alkyl group having up to 5 carbon atoms
• R 5 is an alkylene group having up to 6 carbon atoms in the chain, optionally substituted by one or more hydrocarbyl groups having up to 10 carbon atoms, an acyl group having from 2 to 10 carbon atoms, or a keto, halo, hydroxy, nitro, cyano or alkoxy derivative of a
• R 6 is a hydrocarbyl substituent having from 2 to 600 carbon atoms or said derivative thereof, a is from 1 to 150, and b is from 0 to 12.
• c when c is zero, there are at least two carbon atoms in the R 10 alkylene chain.
• hydrocarbyl refers to a group having a carbon atom directly attached to the rest of the molecule and having a hydrocarbon or predominantly hydrocarbon character.
• hydrocarbon groups including aliphatic, (e.g., alkyl or alkenyl), alicyclic (e.g., cycloalkyl or cycloalkenyl), aromatic, aliphatic- and alicyclic-substituted aromatic, and aromatic- substituted aliphatic and alicyclic groups.
• Aliphatic groups are advantageously saturated. Examples include methyl, ethyl, propyl, butyl, isobutyl, pentyl, hexyl, octyl, decyl, octadecyl, cyclohexyl, and phenyl.
• hydrocarbyl groups may, as indicated above, contain non-hydrocarbon substituents provided they do not alter the predominantly hydrocarbon character of the group. Examples include keto, halo, hydroxy, nitro, cycano, alkoxy and acyl. If the hydrocarbyl group is substituted, a single (mono) substituent is preferred. Examples of substituted hydrocarbyl groups include 2-hydroxyethyl, 3- hydroxypropyl, 4-hydroxybutyl, 2-ketopropyl, ethoxyethyl, and propoxypropyl. The groups may also or alternatively contain atoms other than carbon in a chain or ring otherwise composed of carbon atoms. Suitable hetero atoms include, for example, nitrogen, oxygen and sulfur.
• hydrocarbylene is used analogously; such a group is attached to the rest of the molecule at least at one end and preferably at both ends through a carbon atom.
• R 7 is hydrogen or a hydrocarbyl substituent having from 1 to 600 carbon atoms
• R 8 is hydrogen or a C 1 to C 12 hydrocarbyl substituent and, if there is more than one R 8 in a compound, they may be the same or different
• R 9 is a hydrocarbylene substituent having from 2 to 600 carbon atoms, two of which carbon atoms are bonded to the ⁇ -carbon atoms of the succinic anhydride based ring
• X 1 represents hydrogen or an alkyl group having from 1 to 12 carbon atoms
• X 2 represents hydrogen, an alkyl group having from 1 to 12 carbon atoms, a hydroxy group, or an alkoxy group, having from 1 to 12 carbon atoms
• X 1 and X 2 may together represent an oxygen or sulphur atom
• Z has the meaning given above
• h is from 1 to 20.
• h represents l.
• R 10 the alkylene chain may have at most 5 carbon atoms, it may be branched, and the length of the branch or branches is not limited.
• R 3 represents a hydrocarbyl substituent, and Z contains a nitrogen atom
• the hydrocarbyl substituent is advantageously linked to the, or a, nitrogen atom.
• the nitrogen-hydrocarbyl linkage may in that case be, e.g., an amide linkage.
• R 12 is a hydrocarbyl substituent having from 2 to 400 carbon atoms
• R 13 is hydrogen or a C 1 to C 12 hydrocarbyl
• R 14 is a hydrocarbylene substituent having from 4 to 400 carbon atoms, two of which carbon atoms are bonded to the ⁇ -carbon atoms of the succinic anhydride based ring, and Z represents -CH 2 CH 2 CH 2 -;
• the invention also provides a method of reducing particulate emission resulting from the combustion of a fuel oil, which comprises mixing a compound of the formula I or II, more especially a compound of the formula III, IV, or V, as defined above, with the fuel oil before burning the fuel oil. Also provided is a method of reducing particulate emission resulting from burning fuel oil, which comprises the combustion of a fuel oil containing an above-mentioned compound.
• a method for the preparation of the macrocyclic polyamines of the formulae above is described, for example, in U.S. Patent No. 4 637 886, the disclosure of which is incorporated by reference herein.
• Formation of the macrocyclic and optionally polymacrocyclic compounds proceeds by the aminolysis of hydrocarbyl succinic anhydride, monocarboxylic acid or polycarboxylic acid, adding the acid or anhydride to the di or polyamide compound, as described in more detail in the above- referenced U.S. Patent.
• the hydrocarbyl and hydrocarbylene substituents R 12 and R 14 are advantageously derived from a polymer based on a major amount of a C 2 to C 5 olefin, for example homo or copolymers of ethylene, propylene, butylene (1- or 2-), pentylene and, especially, isobutylene.
• Polyisobutylene is especially preferred.
• the polymer when it is a copolymer, it may be a copolymer of two or more of the specified monomers, or a copolymer of one or more of the specified monomers with a copolymerizable unsaturated monomer; when the polymer is a copolymer it may be a block or a random copolymer.
• the polymer advantageously has from 5 to 300 carbon atoms, preferably 10 to 200 carbon atoms and most
• Suitable amine reactants are of the formula
• Preferred amines include 1,3-propane diamine; 3,3'-imino- bis-propylamine, N,N'-bis(3-aminopropyl) ethylene diamine; N,N'-bis(3-aminopropyl)-1,3-propane diamine; other suitable amines include ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, pentamethylene hexamine, dipropylene triamine,
• tripropylene tetramine tetrapropylene pentamine and pentapropylene hexamine.
• anhydride to polyamine used in the preferred preparation of the macrocyclic polyamines may vary, for example, from 0.2:1 to 5:1, and is preferably from 0.5:1 to 2:1, and most preferably from 0.5:1 to 1.5:1.
• monocarboxylic acid there may be used an acid of the formula:
• R 15 is hydrogen, or a substituted or unsubstituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, or aryl group.
• acids include formic acid, acetic acid, propionic acid, butyric acid, valeric acid, palmitic acid, stearic acid, cyclohexanecarboxylic acid, 2- methylcyclohexane carboxylic acid, 4-methylcyclohexane carboxylic acid, oleic acid, linoleic acid, linolenic acid, cyclohex-2-eneoic acid, benzoic acid,
• dicarboxylic acid there may be used an acid of the formula:
• t is zero or an integer, including e.g. oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid and suberic acid, or an acid of the formula:
• R 15 is as defined above.
• acids include the alkyl or alkenyl succinic acids, 2-methylbutanedioic acid, 2-ethylpentanedioic acid, 2-n-dodecylbutanedioic acid, 2-n-dodecenylbutanedioic acid, 2-phenylbutanedioic acid, and 2-(p-methylphenyl)butanedioic acid.
• polysubstituted alkyl dicarboxylic acids wherein other R 15 groups as described above may be substituted on the alkyl chain. These other groups may be substituted on the same carbon atom or different atoms.
• examples include 2,2-dimethylbutanedioic acid
• the dicarboxylic acids also include acids of the formula:
• r is an integer of 2 or more.
• examples include maleic acid, fumaric acid, pent-2-enedioic acid, hex-2- enedioic acid; hex-3-enedioic acid, 5-methylhex-2- enedioic acid; 2,3-di-methylpent-2-enedioic acid;
• the dicarboxylic acids also include aromatic amino acids
• dicarboxylic acids e.g. phthalic acid, isophthalic acid, terephthalic acid and substituted phthalic acids of the formula:
• Examples of such acids include 3-methylbenzene-l,2-dicarboxylic acid; 4-phenylbenzene-1,3- dicarboxylic acid; 2-(1-propenyl)benzene-1,4-dicarboxylic acid, and 3,4-dimethylbenzene-1,2-dicarboxylic acid.
• n is from 1 to 6
• u is from 1 to 6
• b is from 0 to 12.
• the polyamine used to derive the hydrocarbyl polyamine is advantageously a compound having from 2 to 12 nitrogen atoms and from 2 to 40 carbon atoms.
• polyamines including alkylene diamines and substituted polyalkylene polyamines.
• the alkylene group contains from 2 to 6 carbon atoms, there being preferably from 2 to 3 carbon atoms between the nitrogen atoms.
• polyamines examples include ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, di(trimethylene) triamine, propylene diamine, dipropylene triamine, tripropylene tetramine, N-methyl ethylene diamine, N-N,-dimethyl ethylene diamine, N- methyl-1,3-diamino propane and N,N-dimethyl-1,3-diamino propane.
• amines include branched chain polyamines and cyclic structures formed by reaction of linear polyamines.
• polyalkylene polyamines those containing from 2 to 12 nitrogen atoms and from 2 to 24 carbon atoms are especially preferred.
• the additive used may be a derivative of the macrocyclic or hydrocarbyl polyamines described above, such derivative being one obtainable by, and preferably one obtained by, post-treatment with, for example, boron oxide, boron oxide hydrate, a boron halide, a boron acid, sulphur, a sulphur chloride, a phosphorus oxide or sulphide, a carboxylic acid or anhydride, an acyl halide, an epoxide, an episulphide or acrylonitrile.
• Methods for carrying out such treatment are well known in the art; for example boration to incorporate 0.1 to 1 atoms of boron for each nitrogen atom may be carried out as described in U.S.
• Patent No. 3 254 025 the disclosure of which is incorporated by reference herein.
• a preferred post-treatment for the formation of an additive is treatment with polyisobutylene succinic anhydride.
• hydrocarbyl polyamine is treated with 10 to 50 mole % of an anhydride formed from a polyisobutylene of molecular weight 900 to 1200, for example by reaction at 120°C for an hour or until the reaction mixture contains no free anhydride.
• the invention provides the use as a particulate-reducing additive for, and the use in reducing particulate emission in the combustion of, a diesel or jet fuel of a post-treated macrocyclic or hydrocarbyl polyamine as defined above, especially one post treated with a polyisobutylene succinic anhydride.
• the additives may be used either alone or in
• the fuel in the fuel is in the range of from 0.0005 to 2, preferably from 0.001 to 0.5, and more preferably from 0.005 to 0.3%, based on the weight of the fuel.
• additives which may be used include, for example, diesel detergents, antifoam additives, antirust additives, and demulsifiers. These other additives may be present in the fuel in a total concentration of 0.001 to 1, preferably 0.005 to 0.2, and most preferably a total concentration of 0.005 to 0.05%, based on the total weight of fuel.
• a specific example of such a combination is the use of a macrocyclic compound with a detergent which is the uncyclized reaction product formed from a hydrocarbyl succinic anhydride and a polyamine.
• the detergent is advantageously present in a concentration of 0.005 to 0.1, preferably 0.005 to 0.5, and most preferably from 0.005 to 0.2%, based on the total weight of the fuel.
• Preferred cetane improvers are organic nitrates
• organic nitrates are nitrate esters containing aliphatic or cycloaliphatic groups with up to 30 carbon atoms, preferably saturated groups, and preferably with up to 12 carbon atoms.
• nitrates there may be mentioned methyl, ethyl, propyl, isopropyl, butyl, amyl, hexyl, heptyl, octyl, iso-octyl, 2-ethylhexyl, nonyl, decyl, allyl, cyclopentyl, cyclohexyl, methylcyclohexyl, cyclododecyl, 2-ethoxyethyl, and 2-(2-ethoxyethoxy) ethyl nitrates.
• the cetane improver is advantageously used at a concentration in the fuel in the range of from 0.0005 to 1, preferably 0.005 to 0.5 and most preferably from 0.01 to 0.2%, based on the weight of the fuel.
• Example A in which all parts and percentages are by weight unless otherwise indicated, illustrate the invention.
• PIBSA polyisobutylene succinic anhydride
• the saponification number indicates that the product has an effective molecular weight of 870.
• the catalyst was an alkylaryl sulphonic acid and the percentage is based on the charge of PIB.
• the IR spectrum of the product had four peaks between 1900 and 1500 wavenumbers at 1772 (w), 1738 (m), 1705 (s) and 1674 (vs) wavenumbers. Such a spectrum is indicative of the presence of a macrocyclic compound. (In contrast the IR spectrum of the uncyclized additives contains only three peaks in the same region of the spectrum. There is a weak absorption at 1771-72
• the IR spectrum of the product has four peaks between 1900 and 1500 wavenumbers at 1771 (w), 1732 (w), 1702 (s) and 1668 (s) wavenumbers.
• Example C The method of Example C was repeated using N,N'-bis- (3-aminopropyl)-ethylenediamine (87g:0.5 moles).
• the IR spectrum of the product has four peaks between 1900 and 1500 wavenumbers at 1772 (w), 1737 (vs), 1701 (vs) and 1669 (vs).
• a batch of PIBSA was synthesized by reacting 960MW PIB with maleic anhydride at high temperature. The resulting material was diluted with solvent 150 base oil to produce a product with a saponification number of 70.7 mg KOH/g. The saponification number indicates that the product has an effective weight of 1584.
• the thermal PIBSA from Example E (500g:0.32 moles) was added to a solution of 1,3-diaminopropane (24g:0.32 moles) in toluene (200 ml) at 25°C.
• the reaction mixture was heated to reflux and then the solvent and water of reaction were removed by distilling to a pot temperature of 170°C.
• the reaction mixture was held at a temperature of 170°C for 7 hours. During this time IR spectra of the product were recorded to monitor the formation of the macrocycle.
• Example F The method used in Example F was repeated using thermal PIBSA from Example E (500g:0.32 moles) and 3,3'- imino-bis-propylamine (42g:0.32 moles).
• the IR spectrum of the product contained four peaks between 1900 and 1500 wavenumbers at ca. 1770 (w), 1730 (m), 1702 (s) and 1670(s).
• Example F The method used in Example F was repeated using thermal PIBSA from Example E (500g:0.32 moles) and N,N'- bis- (3-aminopropyl) ethylene diamine (56g:0.32 moles).
• the IR spectrum of the product contained four peaks between 1900 and 1500 wavenumbers at 1771(w), 1731(m), 1702(vs) and I668(vs).
• Example E The method used in Example E was repeated using thermal PIBSA from Example E (500g:0.32 moles) and N,N'- bis-(3-aminopropyl)-1,3-propylene diamine (61g:0.32 moles).
• the product was a dark viscous oil which
• Example F The method used in Example F was repeated using thermal PIBSA from Example E (500g:0.32 moles) and pentapropylene hexamine (74g:0.32 moles).
• a sample of PIBSA was prepared by reacting a 960MW PIB with maleic anhyride.
• the resulting PIBSA had a saponification number of 96.3 mg KOH/g, so that the effective molecular weight of the PIBSA was 1163.
• the PIBSA (300g:0.26 moles) was added to a refluxing solution of N,N'-bis-(3-aminopropyl) ethylene diamine (44.8g:0.26 moles) in toluene (200 ml).
• the engine used was a 6 cylinder 4 stroke naturally aspirated DI engine with the following
• the fuel used in the tests was a standard UK
• the engine was conditioned prior to testing each additive by running the engine on the test fuel at 75% speed and 75% load for 12 hours.
• Example 1 The engine and fuel of Example 1 were used to determine the effect of additive concentration on
• Table 1 shows the % reduction of particulate between stages 4 and 3 with different concentrations of additive.
• Example K The additive from Example K was tested alone and in combination with a cetane improver.
• the cetane improver was an alkyl nitrate made from a C 8 alcohol.
• the experiments were carried out using the standard ECE R49 thirteen mode test. The tests were run using a VOLVO TD121/122F engine. The fuel used was similar to that used in Example 1.
• the weight of particulate formed in each stage of the test was measured by collecting the particulate on a pre-weighed filter paper.
• the overall amount of particulate from the 13 modes was determined using the standard weighting factors for each mode. The results are shown in Table 4.
• Example L The additive from Example L was tested alone and in combination with the cetane improver used in Example 3 using the standard ECE R49 thirteen mode test in a
• PERKINS PHASER 180 Ti engine The fuel used was similar to that used in Example 1. The weight of particulate formed in each stage of the test was measured as in Example 3. The results are shown in Table 5.

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• 1990
  • 1990-04-12 GB GB909008346A patent/GB9008346D0/en active Pending
• 1991
  • 1991-04-12 DE DE69130287T patent/DE69130287T2/de not_active Expired - Fee Related
  • 1991-04-12 ES ES91908144T patent/ES2121781T3/es not_active Expired - Lifetime
  • 1991-04-12 WO PCT/EP1991/000704 patent/WO1991016408A1/en not_active Ceased
  • 1991-04-12 JP JP91507474A patent/JPH05507099A/ja active Pending
  • 1991-04-12 KR KR1019920702501A patent/KR0163408B1/ko not_active Expired - Fee Related
  • 1991-04-12 CA CA002080496A patent/CA2080496A1/en not_active Abandoned
  • 1991-04-12 AT AT91908144T patent/ATE171719T1/de not_active IP Right Cessation
  • 1991-04-12 EP EP91908144A patent/EP0525052B1/de not_active Expired - Lifetime
  • 1991-04-12 IN IN318DE1991 patent/IN180348B/en unknown

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