CA1133012A - Amides from aralkyl acids and polyamines as lubricant additives - Google Patents

Amides from aralkyl acids and polyamines as lubricant additives

Info

Publication number
CA1133012A
CA1133012A CA343,000A CA343000A CA1133012A CA 1133012 A CA1133012 A CA 1133012A CA 343000 A CA343000 A CA 343000A CA 1133012 A CA1133012 A CA 1133012A
Authority
CA
Canada
Prior art keywords
compound
fuel
lubricant
acid
detergent additive
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.)
Expired
Application number
CA343,000A
Other languages
French (fr)
Inventor
Sidney Schiff
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.)
Phillips Petroleum Co
Original Assignee
Phillips Petroleum 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
Application filed by Phillips Petroleum Co filed Critical Phillips Petroleum Co
Application granted granted Critical
Publication of CA1133012A publication Critical patent/CA1133012A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/222Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224Amides; Imides carboxylic acid amides, imides
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/16Amides; Imides
    • FMECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02BINTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
    • F02B61/00Adaptations of engines for driving vehicles or for driving propellers; Combinations of engines with gearing
    • F02B61/04Adaptations of engines for driving vehicles or for driving propellers; Combinations of engines with gearing for driving propellers
    • F02B61/045Adaptations of engines for driving vehicles or for driving propellers; Combinations of engines with gearing for driving propellers for marine engines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/26Amines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/25Internal-combustion engines
    • C10N2040/255Gasoline engines
    • C10N2040/26Two-strokes or two-cycle engines
    • FMECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02BINTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
    • F02B75/00Other engines
    • F02B75/02Engines characterised by their cycles, e.g. six-stroke
    • F02B2075/022Engines characterised by their cycles, e.g. six-stroke having less than six strokes per cycle
    • F02B2075/025Engines characterised by their cycles, e.g. six-stroke having less than six strokes per cycle two
    • FMECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02BINTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
    • F02B77/00Component parts, details or accessories, not otherwise provided for
    • F02B77/04Cleaning of, preventing corrosion or erosion in, or preventing unwanted deposits in, combustion engines

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Mechanical Engineering (AREA)
  • General Engineering & Computer Science (AREA)
  • Combustion & Propulsion (AREA)
  • Ocean & Marine Engineering (AREA)
  • Lubricants (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Abstract of the Disclosure Aralkyl acid and polyamine are reacted to produce amide that is a detergent lubricant and fuel additive that is particularly effective to keep two-cycle engines clean.

Description

1~33V12 AMIDES FROM ARALRYL ACIDS AND
POLYAMINES AS LUBRICANT ADDITIVES
Background of the Invention This invention relates to additives for hydrocarbons suitable for use in an internal combustion engine. In one of its aspects, this invention relates to detergent additives for lubricants and hydrocarbon fuels.
It is common practice to add detergent compounds, detergent compositions, or detergent packages, i.e., a mixture of detergent compositions along with other additives, to lubricant and fuel compositions to prevent the deposition of solid materials on engine surfaces which come into contact with the lubricant or fuel compositions.
The deposits formed in the engine interfere with the proper circulation of the lubricant and fuel compositions and also act as abrasives which can aggravate the wearing of engine parts.
It has also been found that some detergent additives that have been employed in lubricant and fuel compositions actually contribute to the formation of deposits in modern engines. It is, therefore, always of interest when compounds or compositions that provide improved detergent additive properties are discovered.
It is, therefore, an object of this invention to provide a detergent additive for internal combustion engine fuels and lubricants.
It is another object of this invention to provide a method for retarding the depositing of solid materials on the surfaces of internal combustion engines. It is still another object of this invention to provide detergent fuel compositions and detergent lubricating compositions for internal combustion engines.

1~330~2 Other aspects, objects and the various advantages of this invention will become apparent upon reading the specification and the appended claims.
Statement_of the Invention In accordance with this invention, detergent additives for lubricants and fuels for use in internal combustion engines is provided.
The detergent additive is those amides made by reaction between aralkyl acids and polyamines. The detergent lubricant and fuel additives are particularly effective to keep two-cycle, outboard engines clean.
In one of its embodiments, this invention provides a fuel or lubricant composition for use in internal combustion engines. The composition is a mixture of a fuel or lubricant with a detergent additive amide, produced as described above.
In still another embodiment of the invention a method is provided for maintaining the cleanliness of an internal combustion engine by the addition to the hydrocarbon fuel or lubricant for the engine of a detergent additive amide produced as described above.
Aralkyl acids that are suitable for use to synthesize the additive are those acids that can be prepared by alkylation of an aromatic hydrocarbon such as benzene, toluene, xylenes, or the like with an unsaturated fatty acid such as the mono-unsaturated acids lauroleic, myristoleic, palmitoleic, oleic, gadoleic, and the like, or with poly-unsaturated fatty acids such as linoleic, linolenic, or moroctic acids--Cl~ acids having two, three, and four double bonds, respectively. The aralkyl radical R of the acids (RCOON) can contain from about 11-41 carbon atoms; preferably it will contain 17-29 carbon atoms. Examples of suitable aralkyl acids are diphenyllauric acid, triphenylpalmitic acid, phenyl stearic acid, and the like in which at least one aromatic radical is combined in the original fatty acid.
Polyamines that are suitable for use can be represented by the formula NH2(CH2CH2NH) H in which x is an integer between two and six.
Examples are diethylenetriamine, triethylenetetramine, and tetraethylenepentamine. ~specially preferred is the latter amine in which x is four.
The ratio in which aralkyl acid and polyamine are combined for reaction is about 0.2-1.0 moles of acid per equivalent of nitrogen.
Preferably the ratio is between about 0.4-0.8 moles of acid per equivalent of nitrogen.

3 276g5 Production of amides by reaction between aralkyl acids and polyamines is accompanied by the liberation of water, and is facilitated by the use of temperatures above the normal boiling point of water. Reaction can be effected without using a solvent by operating under conditions in which water vapor is removed from the reactants with the aid of a stream of gas, preferably inert, such as nitrogen or argon. Alternatively the reaction can be effected in a solvent such as a hydrocarbon that permits operation under reflux at a temperature of about 100-200C. Since one mole of water is produced per mole of amide, measurement of evolved water provides a convenient method to follow the extent of the reaction.
In addition to being effective to maintain the cleanliness of an outboard engine during extended operation, the additive of this invention is useful to prevent or reduce the formation of harmful carburetor and fuel intake system deposits when admixed with the fuel of any internal combustion engines. For this application the additive is used at a concentration of about 1-250 pounds per thousand barrels of fuel.
The additive is also useful with lubricant stocks, particularly solvent refined, paraffinic stock having a viscosity index of 100 or above and a viscosity at 210F of about 39 to about 100 Saybolt Universal seconds (SUS), preferably about 45 to about 75 SUS. Other additives commonly used to formulate lubricants, such as viscosity index improvers, antioxidants, and the like can be used in formulation with the additive of this invention without destroying the effectiveness of the additives.
The following example illustrates the preparation of an amide that is subsequently shown to possess good detergent properties when incorporated into the lubricant for a two-cycle outboard engine.
Example Amide was prepared by combining 2238 g (6.0 moles) of phenylstearic acid ~as commercially available from Armak Co.) and 378 g (2.0 moles) of tetraethylenepentamine in a flask fitted with a stirrer, a water-cooled reflux condenser, a Barrett water trap, and a heating mantle. After addition of 835 ml of xylene the mixture was heated to boiling and maintained at reflux for 3.2 hours during which interva] 125 ml (6.9 moles) of water was collected. Water in excess of the expected 6.0 moles was presumably present as an impurity in the reactants. Solvent was ~lW012 removed from the product by distillation at 132C kettle temperature at 7 torr pressure.
The solvent-free additive was incorporated into a lubricating oil blend at a concentration of 10.1 volume percent. The resulting mixture was combined with gasoline in the volume ratio 1:50, respectively, and tested for 100 hours in a 25 horsepower Johnson two-cycle outboard engine at wide open throttle (about 4800-4900 rpm~ except for five minutes of idling at hourly intervals. The additive was evaluated by the Piston Varnish Test, a rating system developed by the Coordinating Research Council (CRC) that indicates the relative amount of varnish deposit on a piston. In this system a rating of 10 designates a clean piston and zero designates a very dirty one. This system is used by the Boating Industry Association to certify two-cycle lubricants for service TC-W. A satisfactory additive should produce a Piston Varnish rating of at least 9Ø The additive made and evaluated as described in this example received a 9.7 rating.

Claims (9)

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:
1. A compound useful as a detergent additive for lubricants and fuels prepared by reacting (1) aralkyl acid chosen from among the group consisting of diphenyllauric acid, triphenylpalmitic acid and phenyl stearic acid and (2) polyamine represented by the formula NH2(CH2CH2NH)xH in which x is an integer between 2 and 6 to produce an amide, said aralkyl acid having been prepared by alkylation of an aromatic hydrocarbon with an unsaturated fatty acid.
2. A compound of claim 1 in which x is 4.
3. A compound of claim 2 in which the aralkyl acid is phenylstearic acid and the polyamine is tetraethylenepentamine.
4. A composition comprising a lubricating oil and the compound of claim 1, said compound of claim 1 present in an amount effective as a lubricating oil detergent additive.
5. A composition comprising a hydrocarbon suitable as fuel in an internal combustion engine and a compound of claim 1, said compound of claim 1 present in an amount effective as a fuel detergent additive.
6. A composition comprising a lubricating oil and a compound of claim 3, said compound of claim 3 present in an amount effective as a lubricating oil detergent additive.
7. A composition comprising a hydrocarbon suitable as fuel in an internal combustion engine and a compound of claim 3, said compound of claim 3 present in an amount effective as a fuel detergent additive.
8. A method for maintaining the cleanliness of an internal combustion engine comprising the addition of a detergent additive of claim 1 to the hydrocarbon fuel or lubricant for the engine, said detergent being added in an amount effective to reduce engine deposits and using said hydrocarbon fuel or lubricant with detergent additive as fuel or lubricant in an internal combustion engine.
9. A method for maintaining the cleanliness of an internal combustion engine comprising the addition of a detergent additive of claim 3 to the hydrocarbon fuel or lubricant for the engine, said detergent being added in an amount effective to reduce engine deposits and using said hydrocarbon fuel or lubricant with detergent additive as fuel or lubricant in an internal combustion engine.
CA343,000A 1979-03-20 1980-01-03 Amides from aralkyl acids and polyamines as lubricant additives Expired CA1133012A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US2224579A 1979-03-20 1979-03-20
US22,245 1979-03-20

Publications (1)

Publication Number Publication Date
CA1133012A true CA1133012A (en) 1982-10-05

Family

ID=21808611

Family Applications (1)

Application Number Title Priority Date Filing Date
CA343,000A Expired CA1133012A (en) 1979-03-20 1980-01-03 Amides from aralkyl acids and polyamines as lubricant additives

Country Status (7)

Country Link
EP (1) EP0016972A1 (en)
JP (1) JPS55125200A (en)
AU (1) AU518067B2 (en)
BR (1) BR8001135A (en)
CA (1) CA1133012A (en)
ES (1) ES8102724A1 (en)
NO (1) NO800790L (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4737160A (en) * 1984-11-02 1988-04-12 Phillips Petroleum Company Reaction products of amido-amine and epoxide useful as fuel additives
US4746328A (en) * 1985-07-19 1988-05-24 Kao Corporation Stabilized fuel oil containing a dispersant
KR870008997A (en) * 1986-03-27 1987-10-22 앤 에이취. 제이콥슨 Antifouling fuel composition

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3429674A (en) * 1962-02-02 1969-02-25 Lubrizol Corp Oil-soluble nitrogen composition

Also Published As

Publication number Publication date
AU5519080A (en) 1980-10-09
EP0016972A1 (en) 1980-10-15
BR8001135A (en) 1980-11-04
JPS55125200A (en) 1980-09-26
AU518067B2 (en) 1981-09-10
ES489558A0 (en) 1981-02-16
NO800790L (en) 1980-09-22
ES8102724A1 (en) 1981-02-16

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MKEX Expiry

Effective date: 19991005