CA1133012A - Amides from aralkyl acids and polyamines as lubricant additives - Google Patents
Amides from aralkyl acids and polyamines as lubricant additivesInfo
- 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
Links
- 150000001408 amides Chemical class 0.000 title claims abstract description 11
- 125000003710 aryl alkyl group Chemical group 0.000 title claims abstract description 10
- 229920000768 polyamine Polymers 0.000 title claims abstract description 9
- 239000003879 lubricant additive Substances 0.000 title abstract description 4
- 239000003599 detergent Substances 0.000 claims abstract description 28
- 239000002253 acid Substances 0.000 claims abstract description 13
- 239000000654 additive Substances 0.000 claims description 29
- 239000000446 fuel Substances 0.000 claims description 25
- 230000000996 additive effect Effects 0.000 claims description 23
- 239000000314 lubricant Substances 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- 238000002485 combustion reaction Methods 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- 150000002430 hydrocarbons Chemical class 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- 239000010687 lubricating oil Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- MKJHXLKVZNDNDB-UHFFFAOYSA-N 2-phenyloctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(C(O)=O)C1=CC=CC=C1 MKJHXLKVZNDNDB-UHFFFAOYSA-N 0.000 claims description 4
- 230000003749 cleanliness Effects 0.000 claims description 4
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical group NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 3
- PIXVEISBEBXHNH-UHFFFAOYSA-N 16,16,16-triphenylhexadecanoic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(CCCCCCCCCCCCCCC(=O)O)C1=CC=CC=C1 PIXVEISBEBXHNH-UHFFFAOYSA-N 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 2
- 239000002816 fuel additive Substances 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- RNAMYOYQYRYFQY-UHFFFAOYSA-N 2-(4,4-difluoropiperidin-1-yl)-6-methoxy-n-(1-propan-2-ylpiperidin-4-yl)-7-(3-pyrrolidin-1-ylpropoxy)quinazolin-4-amine Chemical compound N1=C(N2CCC(F)(F)CC2)N=C2C=C(OCCCN3CCCC3)C(OC)=CC2=C1NC1CCN(C(C)C)CC1 RNAMYOYQYRYFQY-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000003082 abrasive agent Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
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
- 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
- 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
-
- 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
- F02B61/00—Adaptations of engines for driving vehicles or for driving propellers; Combinations of engines with gearing
- F02B61/04—Adaptations of engines for driving vehicles or for driving propellers; Combinations of engines with gearing for driving propellers
- F02B61/045—Adaptations of engines for driving vehicles or for driving propellers; Combinations of engines with gearing for driving propellers for marine engines
-
- 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
- C10M2215/26—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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
-
- 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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
-
- 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
- C10N2040/26—Two-strokes or two-cycle 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
-
- 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
- F02B77/00—Component parts, details or accessories, not otherwise provided for
- F02B77/04—Cleaning 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.
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)
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.
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)
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3429674A (en) * | 1962-02-02 | 1969-02-25 | Lubrizol Corp | Oil-soluble nitrogen composition |
-
1980
- 1980-01-03 CA CA343,000A patent/CA1133012A/en not_active Expired
- 1980-02-04 AU AU55190/80A patent/AU518067B2/en not_active Ceased
- 1980-02-25 JP JP2262880A patent/JPS55125200A/en active Pending
- 1980-02-27 BR BR8001135A patent/BR8001135A/en unknown
- 1980-03-01 EP EP80101023A patent/EP0016972A1/en not_active Withdrawn
- 1980-03-14 ES ES489558A patent/ES8102724A1/en not_active Expired
- 1980-03-19 NO NO800790A patent/NO800790L/en unknown
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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