EP0580587A4 - Additifs diminuant l'emission de fumee pour melange deux temps carburant/lubrifiant. - Google Patents

Additifs diminuant l'emission de fumee pour melange deux temps carburant/lubrifiant.

Info

Publication number
EP0580587A4
EP0580587A4 EP92903743A EP92903743A EP0580587A4 EP 0580587 A4 EP0580587 A4 EP 0580587A4 EP 92903743 A EP92903743 A EP 92903743A EP 92903743 A EP92903743 A EP 92903743A EP 0580587 A4 EP0580587 A4 EP 0580587A4
Authority
EP
European Patent Office
Prior art keywords
mixture
carbon atoms
amine
oil
fuel
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP92903743A
Other languages
German (de)
English (en)
Other versions
EP0580587A1 (fr
EP0580587B1 (fr
Inventor
Jacob Joseph Habeeb
Christopher John May
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ExxonMobil Technology and Engineering Co
Original Assignee
Exxon Research and Engineering Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US07/634,984 external-priority patent/US5108462A/en
Application filed by Exxon Research and Engineering Co filed Critical Exxon Research and Engineering Co
Publication of EP0580587A1 publication Critical patent/EP0580587A1/fr
Publication of EP0580587A4 publication Critical patent/EP0580587A4/fr
Application granted granted Critical
Publication of EP0580587B1 publication Critical patent/EP0580587B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • 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, 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
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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
    • C10L1/224—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
    • C10L1/24—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, 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
    • C10L1/26—Organic compounds containing phosphorus
    • C10L1/2608—Organic compounds containing phosphorus containing a phosphorus-carbon bond
    • C10L1/2625—Organic compounds containing phosphorus containing a phosphorus-carbon bond amine salts
    • C—CHEMISTRY; METALLURGY
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    • C10L1/00—Liquid carbonaceous fuels
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    • C10L1/14—Organic compounds
    • C10L1/26—Organic compounds containing phosphorus
    • C10L1/2633—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond)
    • C10L1/2658—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond) amine salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/16—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/12—Thio-acids; Thiocyanates; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/12—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M135/14—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond
    • C10M135/18—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond thiocarbamic type, e.g. containing the groups
    • 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
    • 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
    • C10L1/188—Carboxylic acids; metal salts thereof
    • C10L1/1881—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
    • C10L1/1883—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom polycarboxylic acid
    • 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
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    • C10L1/14—Organic compounds
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    • C10L1/188—Carboxylic acids; metal salts thereof
    • C10L1/189—Carboxylic acids; metal salts thereof having at least one carboxyl 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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    • C10L1/14—Organic compounds
    • C10L1/20—Organic compounds containing halogen
    • C10L1/201—Organic compounds containing halogen aliphatic 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, 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
    • C10L1/30—Organic compounds compounds not mentioned before (complexes)
    • C10L1/305—Organic compounds compounds not mentioned before (complexes) organo-metallic compounds (containing a metal to carbon bond)
    • C10L1/306—Organic compounds compounds not mentioned before (complexes) organo-metallic compounds (containing a metal to carbon bond) organo Pb compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/044—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms having cycloaliphatic groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08—Amides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08—Amides
    • C10M2215/082—Amides containing hydroxyl groups; Alkoxylated derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/26—Amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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    • C10M2215/28—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • C10M2219/066—Thiocarbamic type compounds
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/047—Thioderivatives not containing metallic elements
    • C—CHEMISTRY; METALLURGY
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
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    • C10N2040/25—Internal-combustion engines
    • C10N2040/251—Alcohol fueled engines
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    • C10N2040/255—Gasoline engines
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/26—Two-strokes or two-cycle engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/28—Rotary engines
    • 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
    • F02B75/00—Other engines
    • F02B75/02—Engines characterised by their cycles, e.g. six-stroke
    • F02B2075/022—Engines characterised by their cycles, e.g. six-stroke having less than six strokes per cycle
    • F02B2075/025—Engines characterised by their cycles, e.g. six-stroke having less than six strokes per cycle two

Definitions

  • This invention relates to a lubricant-fuel mixture for two-cycle internal combustion engines in which the mixture has reduced smoke emission due to the presence of an amine salt and/or amide of a derivative of benzoic acid or thiobenzoic acid, a hydrocarbyl substi ⁇ tuted amine salt of a derivative of phosphoric acid, or certain quaternary ammonium hydroxides.
  • Amine salts of certain benzoic acid derivatives have been used as extreme pressure (EP) agents for water-based metal cutting fluids (see for example, Japanese Patent No. 55023132).
  • Substituted benzoic acids have also been used as EP agents in water-based fluids (see for example, U.S. Patent 4,569,776).
  • U.S. Patent No. 4,434,066 discloses a water based hydraulic fluid containing a combination of a hydroxyl-substituted aromatic acid component and a nitroaromatic compound component.
  • U.S. Patent No. 4,012,331 discloses a lubricating oil composition comprising a sulfur compound prepared by reacting a trithiolan compound with a thiol compound in the presence of a base.
  • U.S. Patents 4,787,916 and 4,902,437 together with the patents disclosed therein, describe the use of quaternary ammonium hydroxides in fuels and in lubricating oils, respectively.
  • this invention concerns a two-cycle engine lubricant-fuel mixture that comprises
  • Ri, R2, R3, R4 and R5 are selected from hydrogen; a hydro ⁇ carbyl group containing from 1 to 24 carbon atoms; a hydroxy group; and an oxygen-containing hydrocarbyl group containing from 1 to 24 carbon atoms and at least one of the radicals Ri, R2, R3, R4 or R5 is a hydrocarbyl group containing from 1 to 24 carbon atoms;
  • X is oxygen or sulfur and R6 and R7 are selected from hydrogen and a hydrocarbyl group containing from 1 to 28 carbon atoms; or
  • Rs is a hydrocarbon radical or a hydroxy terminated radical having from 1 to 24 carbon atoms
  • Rg is a hydrocarbon radical having from 1 to 24 carbon atoms
  • Rio and RJJ are hydro ⁇ carbon radicals having from 4 to 24 carbon atoms.
  • this invention concerns a method for reducing smoke emission from a two-cycle internal combustion engine by operating the engine with the lubricant-fuel mixture described above.
  • the two-cycle engine lubricant-fuel mixture of this invention requires a lubricating oil basestock, a distillate fuel, and one of the following: an amine salt and/or amide of a derivative of benzoic acid or dithiobenzoic acid, an amine salt of a phosphoric acid derivative, or a particular class of quaternary ammonium hydroxides.
  • a lubricating oil basestock e.g., a distillate fuel, and one of the following: an amine salt and/or amide of a derivative of benzoic acid or dithiobenzoic acid, an amine salt of a phosphoric acid derivative, or a particular class of quaternary ammonium hydroxides.
  • other lubricant and distil ⁇ late fuel additives may be present in the mixture as well.
  • the lubricating oil basestock can be derived from natural lubricating oils, synthetic lubricating oils, or mixtures thereof. In general. the lubricating oil basestock will have a kinematic viscosity ranging from about 5 to about 10,000 cSt at 40 ⁇ C, although typical applications will require an oil having a viscosity ranging from about 10 to about 1,000 cSt at 40 ⁇ C.
  • Natural lubricating oils include animal oils, vegetable oils (e.g., castor oil and lard oil), petroleum oils, mineral oils, and oils derived from coal or shale.
  • Synthetic oils include hydrocarbon oils and halo-substituted hydrocarbon oils such as polymerized and interpolymerized olefins (e.g.. polybutylenes, polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, poly(l-hexenes), poly(l-octenes), poly(l- decenes), etc., and mixtures thereof); alkylbenzenes (e.g.. dodecyl- benzenes, tetradecylbenzenes, dinonylbenzenes, di(2-ethylhexyl)ben ⁇ zene, etc.); polyphenyls (e.g...).
  • polymerized and interpolymerized olefins e.g. polybutylenes, polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, poly(l-
  • Synthetic lubricating oils also include alkylene oxide polymers, interpolymers, copolymers and derivatives thereof wherein the terminal hydroxyl groups have been modified by esterification, etherification, etc.
  • This class of synthetic oils is exemplified by polyoxyalkylene polymers prepared by polymerization of ethylene oxide or propylene oxide; the alky!
  • polyoxyalkylene polymers e.g., methyl-polyisopropylene glycol ether having an average molecular weight of 1000, diphenyl ether of polyethylene glycol having a molecular weight of 500-1000, diethyl ether of polypropylene glycol having a molecular weight of 1000-1500
  • mono- and polycarboxylic esters thereof e.g., the acetic acid esters, mixed C3-C8 fatty acid esters, and C13 oxo acid diester of tetraethylene glycol.
  • Another suitable class of synthetic lubricating oils com ⁇ prises the esters of dicarboxylic acids (e.g.., phthalic acid, succinic acid, alky! succinic acids and alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebasic acid, fumaric acid, adipic acid, linoleic acid di er, malonic acid, alkylmalonic acids, alkenyl malonic acids, etc.) with a variety of alcohols (e.g., butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, di ⁇ ethylene glycol monoether, propylene glycol, etc.).
  • dicarboxylic acids e.g., phthalic acid, succinic acid, alky! succinic acids and alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebasic acid, fuma
  • esters include dibutyl adipate, di (2-ethylhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, the 2-ethylhexyl diester of linoleic acid dimer, and the complex ester formed by reacting one mole of sebacic acid with two moles of tetra- ethylene glycol and two moles of 2-ethylhexanoic acid, and the like,
  • Esters useful as synthetic oils also include those made from C5 to C12 onocarboxylic acids and polyols and polyol ethers such as neopentyl glycol, trimethylolpropane, pentaerythritol, dipentaeryl- thritol, tripentaerythr tol, and the like.
  • Sil con-based oils (such as the polyalkyl-, polyaryl-, polyalkoxy-, or polyaryloxy-siloxane oils and silicate oils) comprise another useful class of synthetic lubricating oils. These oils include tetraethyl silicate, tetraisopropyl silicate, tetra-(2-ethyl- hexyl) silicate, tetra-(4-methyl-2-ethylhexyl) silicate, tetra(p-tert- butylphenyl) silicate, hexa-(4-methyl-2-pentoxy)-disiloxane, poly(methyl)-siloxanes and poly(methylphenyl) siloxanes, and the like- Other synthetic lubricating oils include liquid esters of phosphorus- containing acids (e.g., tricresyl phosphate, trioctyl phosphate, diethyl ester of decylphosphonic acid),
  • the lubricating oil may be derived from unrefined, refined, rerefined oils, or mixtures thereof.
  • Unrefined oils are obtained directly from a natural source or synthetic source (e.g., coal, shale, or tar sands bitumen) without further purification or treatment.
  • Examples of unrefined oils include a shale oil obtained directly from a retorting operation, a petroleum oil obtained directly from distil ⁇ lation, or an ester oil obtained directly from an esterification process, each of which is then used without further treatment.
  • Refined oils are similar to the unrefined oils except that refined oils have been treated in one or more purification steps to improve one or more properties.
  • Suitable purification techniques include distillation, hydrotreating, dewaxing, solvent extraction, acid or base extraction, filtration, and percolation, all of which are known to those skilled in the art.
  • Rerefined oils are obtained by treating refined 3 in processes similar to those used to obtain the refined oils.
  • 1 -e rerefined oils are also known as reclaimed or reprocessed oils and often are additionally processed by techniques for removal of spent additives and oil breakdown products.
  • additives known in the art may be added to the lubricating base oil.
  • additives include dispersants, anti- wear agents, antioxidants, corrosion inhibitors, detergents, pour point depressants, extreme pressure additives, viscosity index improvers, friction modifiers, and the like. These additives are typically disclosed, for example, in "Lubricant Additives” by C. V. Smalhear and R. Kennedy Smith, 1967, pp. 1-11 and in U.S. Patent 4,105,571, the disclosures of which are incorporated herein by refer ⁇ ence.
  • distillate fuels used in two-cycle engines are well known to those skilled in the art and usually contain a major portion of a normally liquid fuel such as hydrocarbonaceous petroleum distil ⁇ late fuel (e.g., motor gasoline as defined by ASTM Specification D-439-73).
  • a normally liquid fuel such as hydrocarbonaceous petroleum distil ⁇ late fuel (e.g., motor gasoline as defined by ASTM Specification D-439-73).
  • Such fuels can also contain non-hydrocarbonaceous mate ⁇ rials such as alcohols, ethers, organo-nitro compounds and the like (e.g. ethanol, ethanol , diethyl ether, methyl ethyl ether, nitro- ethane), are also within the scope of this invention as are liquid fuels derived from vegetable or mineral sources such as corn, alfalfa, shale, and coal.
  • gasoline that is, a mixture of hydrocarbons having an ASTM boiling point of 60 ⁇ C at the 10% distillation point to about 205'C at the 90% distillation point.
  • Two-cycle fuels may also contain other additives which are well known to those skilled in the art. These can include anti-knock agents such as tetra-alkyl lead compounds, lead scavengers such as halo-alkanes (e.g., eihylene dichloride and ethylene dibro ide), dyes, cetane improvers, anti-oxidants such as 2,6-di-tertiary-butyl-4- methylphenol, rust inhibitors such as alkylated succinic acids and anhydrides, bacteriostatic agents, gum inhibitors, metal deactivators, demulsifiers, upper cylinder lubricants, anti-icing agents, and the like.
  • This invention is useful with lead-free as well as lead con ⁇ taining fuels.
  • the lubricant-fuel mixture of this invention will also contain a hydrocarbyl substituted amine salt and/or amide of an oil- soluble benzoic acid or thiobenzoic acid derivative, an amine salt of a phosphoric acid derivative, or a particular class of quaternary ammonium hydroxides.
  • hydrocarbyl substituted amine salt and/or amide (prefer ⁇ ably an amine salt) of an oil-soluble benzoic acid or thiobenzoic acid derivative has the formula
  • R5 wherein X is oxygen or sulfur, preferably sulfur, and Ri, R2, R3, R4 and R5 are selected from hydrogen; a hydrocarbyl group containing from 1 to 24 carbon atoms, preferably an alkyl group containing from 1 to 18 carbon atoms; a hydroxy group, i.e., -OH; and an oxygen-containing hydrocarbyl group containing from 1 to 24 carbon atoms and at least one of the radicals Ri, R2, R3, R4 or R5 is a hydrocarbyl, preferably an alkyl group, containing from 1 to 24, preferably from 1 to 18 carbon atoms, most preferably from 1 to 6 carbon atoms.
  • benzoic or dit iobenzoic acid derivatives include 4-hydroxy 3,5 ditertiary butyl dithiobenzoic acid; 4-hydroxy 3,5 ditertiary butyl benzoic acid; 3,5 dimethyl dithioben ⁇ zoic acid; 4-hydroxy 3,5 dimethyl dithiobenzoic acid and the like.
  • the oil soluble additive is formed in a conventional manner by mixing substantially equi olar amounts of the benzoic acid deriva ⁇ tive and a hydrocarbyl substituted amine at temperatures generally in the range of 20 ⁇ C - lOO'C.
  • the hydrocarbyl groups of the amine include groups which may be straight or branched chain, saturated or unsaturated, aliphatic, cycloaliphatic, aryl, alkaryl, etc. Said hydrocarbyl groups may contain other groups, or atoms, e.g. hydroxy groups, carbonyl groups, ester groups, or oxygen, or sulfur, or chlorine atoms, etc. These hydrocarbyl groups will usually be long chain, e.g. * C12 to C40, e.g. C14 to C24. However, some short chains, e.g. Ci to Cn may be in ⁇ cluded as long as the total numbers of carbons is sufficient for solubility.
  • the resulting compound should contain a sufficient hydrocarbon content so as to be oil-soluble.
  • the number of carbon atoms necessary to confer oil solubility will vary with the degree of polarity of the compound.
  • the compound will preferably also have at least one straight chain alkyl segment extending from the compound containing 8 to 40, e.g. 12 to 30 carbon atoms.
  • the amines may be primary, secondary, tertiary or quater ⁇ nary, but preferably are secondary. If amides are to be made, then primary or secondary amines will be used.
  • Examples of primary amines include n-dodecyl amine, n- tridecyl amine, C13 Oxo amine, coco amine, tallow amine, behenyl amine, etc.
  • Examples of secondary amines include methyl-lauryl amine, dodecyl-octyl amine, coco-methyl amine, tallow-methylamine, methyl- n-octyl amine, methyl-n-dodecyl amine, methyl-behenyl amine, ditallow amine etc.
  • tertiary amines examples include coco-diethyl amine, cyclohexyl-diethyl amine, coco-dimethyl amine, tri-n-octyl amine, di-methyl-dodecyl amine, methyl-ethyl-coco amine, methyl-cetyl stearyl amine, etc.
  • Amine mixtures may also be used and many amines derived from natural materials are mixtures.
  • the preferred amines include the long straight chain alkyl amines containing from 8 to 40, preferably from 12 to 24, carbon atoms. Naturally occurring amines, which are gener ⁇ ally mixtures, are preferred.
  • Examples include coco amines derived from coconut oil which is a mixture of primary amines with straight chain alkyl groups ranging from C ⁇ to Cis- Another example is di tallow amine, derived from hydrogenated tallow acids, which amine is a mixture of C14 to Ci8 straight chain alkyl groups. Ditallow amine is particularly preferred.
  • hydrocarbyl substituted amine salt of an oil-soluble phosphoric acid derivative has the formula
  • X is oxygen or sulfur, preferably sulfur
  • R5 and R7 are selected from hydrogen and a hydrocarbyl group containing from 1 to 28 carbon atoms, preferably an alkyl group containing from 4 to 12 carbon atoms.
  • at least one of the radicals R_ or R7 is a hydro ⁇ carbyl group, preferably an alkyl group, containing from 3 to 18 carbon atoms.
  • the phosphoric acid derivative include dioctyldithiophosphoric acid; dihexyldithiophosphoric acid; dibutyl- dithiophosphoric acid; didodecylphenyldithiophosphoric acid; dioctyl- phosphoric acid; butylhexyldithiophosphoric acid; butyloctyldithi0- phosphoric acid; and the like.
  • the phosphoric acid derivative may be formed in a conven ⁇ tional manner by mixing substantially equimolar amounts of the phos ⁇ p oric acid derivative and a hydrocarbyl substituted amine at tempera ⁇ tures generally in the range of 15 to 100°C.
  • the hydrocarbyl substi ⁇ tuted amines include those described with respect to the preparation of the aforedescribed second component.
  • the preferred amines include - li ⁇ the long straight chain al amines containing from 8 to 40, prefer ⁇ ably from 12 to 18, carbon atoms. Naturally occurring amines, which are generally mixtures, are preferred.
  • coco amines derived from coconut oil which is a mixture of primary amines with straight chain alkyl groups ranging from Cs to Cjs-
  • tallow amine derived from hydrogenated tallow acids, which amine is a mixture of C14 to Ci8 straight chain alkyl groups. Tallow amine is particularly preferred.
  • the oil-soluble quaternary ammonium hydroxide has the formula
  • R ⁇ is a hydrocarbon radical (or group) or a hydroxy terminated radical (or group) having from 1 to 24 carbon atoms
  • Rg is a hydrocar ⁇ bon radical having from 1 to 24 (preferably from 4 to 24) carbon atoms
  • Rio and RJJ are hydrocarbon radicals having from 4 to 24 carbon atoms.
  • the hydrocarbon radicals (R ⁇ , Rg, Rio, and R ⁇ ) can be alkyl groups, unsaturated paraffin groups, cyclic hydrocarbon groups, aryl groups, arylalkyl groups or mixtures thereof. In addition, said groups can be normal, branched, substituted groups or mixtures there ⁇ of.
  • the hydrocarbon radicals may also contain other atoms such as nitrogen, oxygen, or sulfur; e.g., in the form of an alcohol, an amine, a ketone, a sulfide, a thiosulfide, and other functionalities.
  • Quaternary ammonium hydroxides in which the hydrocarbon radical is octyl, dodecyl, decyl, octadecyl, capryl radicals, or their mixtures are preferred.
  • Preferred quaternary ammonium hydroxides are dimethyl dioctadecyl ammonium hydroxide, tetraoctyl ammonium hydroxide, tricaprylmethyl ammonium hydroxide, or mixtures thereof. Tetraoctyl ammonium hydroxide, tricapryl ethyl ammonium hydroxide, or mixtures thereof are especially preferred, with tricaprylmethyl ammonium hydroxide being most preferred.
  • quaternary ammonium hydroxides described hereinabove can be readily prepared from their corresponding commercially available quaternary ammonium salt, such as a halide.
  • a quaternary ammonium chloride may be contacted with an anion exchange resin such that the chloride is exchanged to produce the corresponding quaternary ammonium hydroxide.
  • Oil-soluble means that the additive is soluble in the mixture at ambient temperatures, e.g., at least to the extent of about 5 wt.% additive in the mixture at 25 ⁇ C.
  • two-cycle engine lubricating oils are often added directly to the fuel to form a mixture of oil and fuel which is then introduced into the engine cylinder.
  • Such lubricant-fuel blends generally contain per 1 part of oil about 20-250 parts fuel, typically they contain 1 part oil to about 30-100 parts fuel.
  • the amount of additive in the mixture can vary broadly depending on the lubricant-fuel mixture ratio. Accordingly, only an amount effective in reducing the smoke of the mixture need be added. In practice, however, the amount of additive added will range from about 0.1 to about 5 wt.%, preferably from about 0.5 to about 1 wt.%, based on weight of lubricant in the lubricant-fuel mixture.
  • the mixture comprised a commercially available two-cycle engine lubricating oil and a commercially avail ⁇ able unleaded gasoline having an RON of 91 and an oil to fuel ratio of 1 to 33.
  • the samples tested were the lubricant-fuel mixture without additives, the mixture with a conventional smoke reducing additive (barium sulfonate), and the mixture with dihydrogenated tallow amine:4-hydroxy-3,5-ditert-butyldithiobenzoate (DTA.-DTB).

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Combustion & Propulsion (AREA)
  • Lubricants (AREA)

Abstract

Mélange carburant/lubrifiant contenant un sel aminé et/ou un amide de dérivé d'acide benzoïque ou thiobenzoïque, un sel aminé d'un dérivé d'acide phosphorique ou certains hydroxydes d'ammonium quaternaire, efficace pour diminuer les émissions de fumée pendant le fonctionnement d'un moteur à combustion interne à deux temps.
EP92903743A 1990-12-27 1991-12-18 Additifs pour melanges carburant/lubrifiant diminuant les emissions de fumees des moteurs deux temps Expired - Lifetime EP0580587B1 (fr)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US63483590A 1990-12-27 1990-12-27
US63483690A 1990-12-27 1990-12-27
US634835 1990-12-27
US634836 1990-12-27
US07/634,984 US5108462A (en) 1990-12-27 1990-12-27 Smoke reducing additive for two-cycle engine lubricant-fuel mixture
US634984 1990-12-27
PCT/US1991/009599 WO1992012224A1 (fr) 1990-12-27 1991-12-18 Additifs diminuant l'emission de fumee pour melange deux temps carburant/lubrifiant

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US5352374A (en) * 1993-02-22 1994-10-04 Exxon Research & Engineering Co. Lubricant composition containing alkoxylated amine salt of a dihydrocarbyldithiophosphoric acid (law024)
DE69403322T2 (de) * 1993-02-22 1997-10-16 Exxon Research Engineering Co Schmierstoffzusammensetzung die alkoxylierten aminsalze aus säuren enthält
GB9621261D0 (en) 1996-10-11 1996-11-27 Exxon Chemical Patents Inc Lubricity additives for fuel oil compositions
GB9621263D0 (en) * 1996-10-11 1996-11-27 Exxon Chemical Patents Inc Lubricity additives for fuel oil compositions

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US3035905A (en) * 1958-02-04 1962-05-22 Union Oil Co Internal combustion engine fuel
BE777944R (fr) * 1972-01-12 1972-05-02 Du Pont Additif a fonctions multiples pour essence d'auto et essences qui en
US4002437A (en) * 1975-02-27 1977-01-11 S.A. Texaco Belgium N.V. Diesel fuel composition
US3951829A (en) * 1975-05-05 1976-04-20 Cities Service Company Two-cycle and rotary combustion engine lubricant
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EP0580587A1 (fr) 1994-02-02
EP0580587B1 (fr) 1997-05-21
CA2097326A1 (fr) 1992-06-28
JPH06507650A (ja) 1994-09-01
WO1992012224A1 (fr) 1992-07-23

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