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  • C10L10/00—Use of additives to fuels or fires for particular purposes
  • C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
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  • C10L1/00—Liquid carbonaceous fuels
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  • 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
  • C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/14—Organic compounds
  • C10L1/16—Hydrocarbons
  • C10L1/1625—Hydrocarbons macromolecular compounds
  • C10L1/1633—Hydrocarbons macromolecular compounds homo- or copolymers obtained by reactions only involving carbon-to carbon unsaturated bonds
  • C10L1/1641—Hydrocarbons macromolecular compounds homo- or copolymers obtained by reactions only involving carbon-to carbon unsaturated bonds from compounds containing aliphatic monomers
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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
  • C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
  • C10L1/1824—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms mono-hydroxy
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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/192—Macromolecular compounds
  • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
  • C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters
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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
  • C10L1/2227—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond urea; derivatives thereof; urethane
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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/224—Amides; Imides carboxylic acid amides, imides
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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/228—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles
  • C10L1/2283—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles containing one or more carbon to nitrogen double bonds, e.g. guanidine, hydrazone, semi-carbazone, azomethine
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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/14—Organic compounds
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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/234—Macromolecular compounds
  • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
  • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
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  • C10L1/234—Macromolecular compounds
  • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
  • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
  • C10L1/2387—Polyoxyalkyleneamines (poly)oxyalkylene amines and derivatives thereof (substituted by a macromolecular group containing 30C)
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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/14—Organic compounds
  • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
  • C10L1/2431—Organic compounds containing sulfur, selenium and/or tellurium sulfur bond to oxygen, e.g. sulfones, sulfoxides
  • C10L1/2437—Sulfonic acids; Derivatives thereof, e.g. sulfonamides, sulfosuccinic acid esters

Definitions

• This invention relates to methods for using friction reduction agents in engine fuels.
• this invention relates to methods for reducing friction in the operation of an internal combustion engine using ethoxylated amines.
• U.S Patent No. 4,086,172 discloses a lubricating oil additive composition which is stated to impart improved oxidation properties to crankcase lubricants comprising an antioxidant and certain oil-soluble hydroxy amines.
• ETHOMEEN 18-12TM which has the formula C 18 H 37 N-(CH 2 CH 2 OH) 2 .
• U.S. Patent No. 4,129,508 discloses a lubricant and fuel composition comprising one or more reaction products of a hydrocarbon-substituted succinic acid or anhydride with one or more polyalkylene glycols or monoethers thereof, one or more organic basic metal salts, and one or more alkoxylated amines.
• the alkoxylated amines include commercially available ETHOMEENTM products, including ETHOMEEN C/12TM. Friihauf states that lubricant and fuel compositions containing these additives possess improved demulsifier properties.
• U.S. Patent No. 4,231,883 discloses lubricating oils and engine fuels containing an hydroxyalkyl amine compounds as additives.
• An example of such an additive is N,N-bis(2-hydroxyethyl)-n-dodecylamine. It is stated that lubricating oils formulated for the crankcase of an internal combustion engine and comprising these additives reduce engine friction and improve fuel mileage. It is further stated that a useful concentration of the additive in the crankcase oil is 0.05 to 3 weight percent.
• U.S. Patent No. 4,409,000 (LeSuer), now Re. 32,174, discloses a combination of hydroxy amines and hydrocarbon-soluble carboxylic dispersants as engine and carburetor detergents for liquid fuels.
• One of the preferred hydroxy amines is ETHOMEEN C/12TM. It is disclosed that such additives inhibit the formation of unwanted deposits in the carburetor and engine.
• U.S. Patent No. 4,836,829 discloses a gasoline additive comprising a mixture of certain hydroxy amines and certain demulsifying agents that are the to be useful for reducing and/or preventing fouling in a multi-port, electronically controlled fuel injection system for an intemal combustion engine.
• Preferred additive mixtures also include an amine oxide as a second anti-fouling agent.
• a preferred hydroxy amine is bis(2-hydroxy ethyl) cocoamine.
• the concentration of the antifouling agent in the fuel is typically from 2 to 200 ppm, preferably 40 to 120 ppm, based on the total weight of the fuel composition.
• friction reducing additives are generally added to lubricating fuel oils, not engine fuels. We have found, however, that it is possible to reduce engine friction by delivering a friction reducing agent to the engine in the form of a friction reducing additive in the gasoline used to fuel the engine. By doing so, increased power and fuel economy may be obtained.
• the present invention provides a method for reducing friction in the operation of an internal combustion engine by delivering to the internal combustion engine a fuel comprising gasoline and a friction-reducing additive.
• the friction-reducing additive comprises a mixture of an effective amount of N,N-bis(hydroxyalkyl)alkylamine and at least one detergent.
• the detergent preferably is a polyalkeneamines, a polyetheramine or a Mannich base-type condensation products.
• the gasoline preferably comprises at least certain minimum amounts of N,N-bis(hydroxyalkyl)-alkylamine, that being at least 7 g.hl. -1 (grams per hectoliter) (at least 25 ptb - pounds per thousand barrels) of gasoline.
• the total amount of N,N-bis(hydroxyalkyl)-alkylamine and detergent should preferably be at least 28.5 g.hl. -1 (100 ptb).
• Gasoline fuels containing less than these minimum required amounts of the above mentioned ingredients do not adequately reduce engine friction and/or improve gasoline mileage.
• the preferred gasolines comprise a mixture of at least 11.4 g.hl. -1 (40 ptb) of N,N-bis(hydroxyethyl)-dodecylamine as the effective friction reducing agent and at least 28.5 g.hl. -1 (100 ptb) of detergent.
• the N,N-bis(hydroxyalkyl)-alkylamine typically has short chain (C 2 -C 4 ) hydroxyalkyl groups and a long chain (C 8 -C 18 ) alkyl group.
• a preferred compound of this type is bis(2-hydroxy ethyl)cocoamine (also known as bis-ethoxylated cocoamine).
• the compounds used as the effective friction reducing agents have the following structure: in which R 1 is a hydrocarbyl group having from 8 to 18 carbon atoms and n is an integer from 2 to 4.
• the preferred N,N-bis(hydroxyethyl) n-dodecylamine is usually derived from coconut fatty acid so that the R 1 substituent generally ranges from C 8 to C 18 , with C 12 and C 14 groups predominanting, mostly straight chain.
• the preferred friction reducing agent is available commercially as ETHOMEEN C/12TM from Akzo Nobel, of Chicago, Illinois. Altematively, it may be prepared using any of the methods for preparing ethoxylated amines which are well known in the art. Generally, ethoxylated amines may be prepared by the reaction of the appropriate hydrocarbyl amine with ethylene oxide, often catalyzed, to form the corresponding ethoxylated amine.
• the concentration of the hydroxyalkyl alkylamine (HAAA) additive in the gasoline is usually at least 7 g.hl. -1 (25 ptd), preferably at least 11.4 g.hl. -1 (40 ptb), more preferably at least 14.25 g. hl. -1 (50 ptb), and even more preferably at least 17.1 g. hl. -1 (60 ptb). More than 28.5 g. hl. -1 (100 ptb) is usually not required for effective friction reduction.
• the other preferred component of the fuel additive is at least one detergent which is typically a polyalkeneamine, a polyetheramine or a Mannich base, all of which are conventional materials.
• these detergents reduce and/or prevent deposits which have a tendency to form in carburetors, fuel injectors, intake valves, and intake ports, thereby improving engine performance.
• Such detergent agents also improve fuel economy and reduce intemal combustion engine exhaust emissions.
• the preferred polyalkeneamine detergents are selected from the group consisting of polymeric 1-amines, including polyisobutylene-amine. High vinylic content polyisobutylene-amines are most preferred. Suitable polyisobutylene-amines are described in U.S patent 5,004,478 (Vogel et al.), 5,112,364 (Rath et al.), and DE 3942860. Preferred polyisobutylene-amines have a weight average molecular weight of 500 to 2000.
• polyalkeneamines are available from normal commercial sources or may be prepared by the amination of high vinylic content polyolefins having a weight average molecular weight of from 500 to 3,000 or greater, using conventional methods.
• Polyisobutylene amines are generally prepared by chlorination or hydroformylation of reactive polyisobutylene and subsequent amination with ammonia, hydrocarbyl amine, hydrocarbyl diamine, hydrocarbyl polyamine, alkoxylated hydrocarbyl amines, or mixtures thereof.
• Ammonia ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, piperazines, hexamethylenediamine, hydroxyalkyl ethylenediamines, hydroxyalkyl triethylenetetraamines, and the like can be incorporated into the polyalkeneamines.
• Such amines can be prepared by the chlorination or halogenation of appropriate polymeric olefins, and subsequently converted into corresponding polyalkene derivatives using these or other known methods of manufacture.
• Altemative preferred detergent agents are the Mannich base condensation products.
• the Mannich base detergents are condensation products of hydrocarbyl phenols, aldehyes, and amines.
• formaldehyde or another aldehyde
• ammonia or with salts of primary or secondary amines, or with amides
• a compound containing an active hydrogen or with salts of primary or secondary amines, or with amides
• the Mannich base reaction of hydrocarbyl phenols, aldehydes, and amines are generally prepared by the alkylation of phenol or phenolics with hydrocarbyl groups having from 10 to 150 or more carbon atoms.
• long chain olefins or polymeric olefins such as polypropylene, polyisobutylene, or mixed polymerized or oligomerized olefins can be used in the phenol alkylation step.
• the substituted phenol is then reacted with a carbonyl source and an amine.
• Carbonyl sources include aldehydes such as formaldehyde, acetaldehyde, propanal, butanal, 2-ethylhexanal and the like.
• aromatic aldehydes may be used to provide a carbonyl source.
• benzaldehyde, vanillin, salicylaldehyde and cinnamaldehyde may be used.
• Dicarbonyl compounds such as glyoxyls as well as carbonyl generating sources such as paraformaldehyde can also be used in some aspects of the invention.
• Amines useful in preparation of the Mannich base condensation product include primary or secondary amines.
• Fatty amines, hydroxyl-containing amines, polyamines such di-, tri-, tetra-, and pentamines or polymeric amines can be used in some aspects of this invention.
• linear and cyclic C 2 -C 6 alkylene di-, tri-, tetra, and pentamines, polyamines, and their substituted polyfunctional derivatives can be used.
• Subtituted derivatives, as used herein, refer to substitution with substituents such as halo, hydroxy, alkoxy, nitro, thio, carbalkoxy and alklythio substituents.
• Amines suitable for use in the Mannich base reaction also include ethylene diamines, diethylene triamines, triethylene tetramines, tetraethyleneamine pentamines, propylene diamines, propylene triamines, ethylene triamines, ethylene tetramines, ethylene pentamines, hexamethylene diamines, and the like. Amines containing from 2 to 30 or more carbon atoms are preferred.
• polyetheramines may be used instead of the polyamines decribed above but generally they are less preferred.
• Typical polyether primary amines include those of the formula R17-O(C2H3(R18)O)[n]C3H6NH[2] where R17 is an alkyl-substituted phenyl group containing 14 to 26 carbon atoms, C6 to C30 alkyl group or C7 to C30 aralkyl group, n is an integer ranging from 2 to 10 and R18 is independently hydrogen or methyl.
• R17 is an alkyl-substituted phenyl group containing 14 to 26 carbon atoms, C6 to C30 alkyl group or C7 to C30 aralkyl group, n is an integer ranging from 2 to 10 and R18 is independently hydrogen or methyl.
• These alkyl-substituted phenol-derived polyetheramines are sold by Texaco Chemical Co. under the trademark Surfonamine.
• Surfonamine MNPA-380TM nonylphenyl-1EO-2PO-NH2
• Surfonamine MNPA-510TM nonylphenyl-4EO-2PO-NH2
• Surfonamine MNPA-750TM nonylphenyl-9.5EO-2PO-NH2
• Surfonamine MNPA-860TM nonylphenyl-12EO-2PO-NH2
• 5,112,364 gasoline-engine fuels which contain small amounts of a polyetheramine is prepared by reductive amination of a phenol-initiated or alkylphenol-initiated polyether alcohol with ammonia or a primary amine
• European Patent Application Publication No. 310,875 fuels for spark ignition engines containing a polyetheramine additive prepared by first propoxylating and/or butoxylating an alkanol or primary or secondary alkylmonoamine and then aminating the resulting polyether with ammonia or a primary aliphatic amine).
• the present invention can be used with gasoline fuels intended for use in spark ignition internal combustion engines.
• gasoline fuels include oxygenated gasolines, reformulated gasolines and gasohols.
• the total amount of HAAA, e.g., ETHOMEEN C/12TM and detergent is preferably is at least 28.5 g.hl. -1 (100 ptb), more preferably at least 42.75 g.hl. -1 (150 ptb), and even more preferably between 48.45 to 57 g.hl. -1 (170 to 200 ptb).
• the total amount of HAAA plus detergent ranges from 28.5 to 85.5 g.hl.
• the amount of detergent is typically from 2.85 to 5.7 g.hl. -1 (10 to 200 ptb, and usually 20 to 42.75 g. hl. -1 (70 to 150 ptb).
• HAAA or detergent can be used.
• the ratio of detergent to HAAA can vary from 10:1 to 1:10, with ratios of from 5:1 to 1:5 being preferred.
• the ratio of detergent to HAAA ranges from 1:1 to 5:1.
• the ratio of detergent to HAAA is 2-3:1.
• additives which are useful in practicing the method of this invention further comprise at least one demulsifier selected from the group consisting of acylated polyglycols; alkyl aryl sulfonates; polyglycols; fatty acid alkylamine reaction products; oxyalkylated alkylphenol (formaldehyde) resins; and oxyalkylated alkylphenolic (formaldehyde) resins and polyoxyalkylene glycol.
• demulsifier selected from the group consisting of acylated polyglycols; alkyl aryl sulfonates; polyglycols; fatty acid alkylamine reaction products; oxyalkylated alkylphenol (formaldehyde) resins; and oxyalkylated alkylphenolic (formaldehyde) resins and polyoxyalkylene glycol.
• a preferred demulsifier is oxyalkylated alkylphenolic (formaldehyde) resins, with or without polyoxyalkylene glycol.
• Suitable demulsifiers which are available commercially include the following materials: Tolad T-284TM (solution of acylated polyglycols in aromatic hydrocarbons), Tolad T-286TM (alkyl aryl sulfonates, polyglycols, oxyalkylated alkylphenol-formaldehyde resins in aromatic hydrocarbons and isopropyl alcohol), Tolad T-326TM (oxyalkylated alkylphenol-formaldehyde resins and polyglycols in aromatic naphtha), Tolad T-500 TM(oxyalkylated alkylphenol-formaldehyde resins in aromatic hydrocarbons and alkanols), Tolad T-292TM (oxyalkylated alkylphenol formaldehyde resins in aromatic hydrocarbons and isoprop
• Suitable carrier fluids include propylene glycol-based polyethers and butylene glycol-based polyethers, aromatic and aliphatic esters, polyalkylenes, and mineral oils.
• a gasoline blend suitable for use in intemal combustion engines is prepared by admixing approximately 14.25 g.hl. -1 (50 ptb) of bis(2-hydroxyethyl) cocoamine and approximately 20 g. hl. -1 (70 ptb) of a polymeric 900 MW polyisobutyleneamine (consisting of primarily more than 70% of terminal amine groups.)
• a gasoline blend suitable for use in an internal combustion engine is prepared by admixing approximately 14.25 g. hl. -1 (50 ptb) of bis(2-hydroxyethyl)cocoamine and approximately 20 g.hl. -1 (70 ptb) of a Mannich base reaction product of polyisobutenyl (approximately 900 MW) alkylated phenol, formaldehyde, and triethylene tetramine based ethylene amines.
• a carboxylate dispersant was prepared according to the generalized teaching of U.S. patent No. 4,409,000.
• a polyisobutylene (having a MW of 900) was reacted with maleic anhydride to form a polyisobutenyl succinic anhydride.
• This hydrocarbyl succinic anhydride was then reacted with tetraethylene pentamine to form a polyisobutenyl succinimide detergent.
• An equal weight mixture of bis(2-hydroxyethyl)cocoamine and succinimide detergent was prepared by blending at approximately 75° C.
• Example 1 Thermogravimetric analysis was performed by heating the sample at 20° C/min in air flowing at 100 ml/min using a TA thermogravimetric analyzer. The percent residue remaining at 325° C, 425° C, and 525° C was recorded. Little or no residue is most desirable.
• the products of this invention show exceptional cleanliness and high temperature decomposition, when compared to Comparative Example A at a various high temperatures.

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• 1998
  • 1998-04-02 EP EP98302599A patent/EP0869163A1/de not_active Withdrawn

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