CN101024787A - Fuel lubricity additives - Google Patents

Fuel lubricity additives Download PDF

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Publication number
CN101024787A
CN101024787A CNA2007100058708A CN200710005870A CN101024787A CN 101024787 A CN101024787 A CN 101024787A CN A2007100058708 A CNA2007100058708 A CN A2007100058708A CN 200710005870 A CN200710005870 A CN 200710005870A CN 101024787 A CN101024787 A CN 101024787A
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fuel
lubricity additives
scheme
amino
unsaturated
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Chinese (zh)
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S·D·施沃布
J·J·贝内特
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Afton Chemical Corp
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Afton Chemical Corp
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    • 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
    • C10L1/2406—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides
    • 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
    • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, 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
    • C10L1/2406—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides
    • C10L1/2418—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides containing a carboxylic substituted; derivatives thereof, e.g. esters
    • 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
    • C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
    • 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

Abstract

A fuel lubricity additive is disclosed comprising an imidazoline. The fuel lubricity additive may be prepared by reacting an optionally substituted organic acid with an optionally substituted polyamine. Fuel compositions are also disclosed, comprising a fuel and the fuel lubricity additive. Processes for reducing wear in an engine, for example an internal combustion engine, using the fuel lubricity additive are disclosed.

Description

Fuel lubricity additives
Technical field
Present disclosure relates to the fuel lubricity additives that comprises tetrahydroglyoxaline.This fuel lubricity additives can be used for improving the oilness of fuel and the wearing and tearing in the reduction oil engine.
Background technology
Pollute and conserve energy, the constantly gasoline mileage of design vehicle for reducing to be improved.This effect to small part is the result of the government specifications of issuing for the gasoline mileage of forcing the automaker to reach regulation.In the effort that meets the requirements of mileage, the size decreases of many automobiles.Yet, in this method, there is the limit, surpass this limit vehicle and can not hold a typical family.The another kind of mode of improving the fuel mileage is to reduce the engine scuffing that part is attributable to engine friction.Present disclosure relates to the fuel lubricity additives that is used for gasoline and diesel oil fuel, and the method that reduces engine scuffing.
The known imidazolidine derivatives that uses in fuel to be improving motor performance, as washing composition, sanitas with minimize carburretion.United States Patent (USP) 3,036,902 disclose the imidazolidine derivatives that is used to reduce the carburetor generation.This derivative is combined with alkanol to form anti-freeze composition.The disclosure that does not wherein have oiliness additive.
United States Patent (USP) 6,562,086 discloses diesel oil fuel and spark ignition fuel lubricity auxiliary agent, the alkanolamide of the alkanolamide of this assistant packet fatty acids, modified fat acid or its mixture.Preparation as the alkanolamide of oiliness additive is known.Yet, such alkanolamide can not be as the fuel lubricity additives of present disclosure effective reduction engine scuffing.
Summary of the invention
According to present disclosure, provide the fuel lubricity additives of the tetrahydroglyoxaline that comprises following formula:
Figure A20071000587000041
Wherein R can be selected from saturated and unsaturated, linear, aromatics, branching and cyclic hydrocarbon group, and it can be unsubstituted or by at least one replacement of hydroxyl, nitro, amino and cyano group; R ' can be independently selected from hydrogen, hydroxyl, nitro, amino, cyano group and saturated and unsaturated, linear, aromatics, branching and cyclic hydrocarbon group; A can be selected from SH, OH and NY 2Group; Can be independently selected from hydrogen and saturated and unsaturated, linear, aromatics, branching and cyclic hydrocarbon group with Y, wherein each can be unsubstituted or by at least one replacement of hydroxyl, nitro, amino and cyano group." amino " herein represent any monobasic-, binary-, ternary-and polyamine and its mixture.
According to present disclosure on the other hand, provide the fuel lubricity additives that comprises tetrahydroglyoxaline, wherein this tetrahydroglyoxaline can be prepared by the method that comprises the steps: the compound that makes formula (I):
Compound reaction with formula (II):
To obtain the tetrahydroglyoxaline of formula (HI):
Figure A20071000587000053
Wherein R can be selected from saturated and unsaturated, linear, aromatics, branching and cyclic hydrocarbon group, and it can be unsubstituted or by at least one replacement of hydroxyl, nitro, amino and cyano group; R ' can be independently selected from hydrogen, hydroxyl, nitro, amino, cyano group and saturated and unsaturated, linear, aromatics, branching and cyclic hydrocarbon group; A can be selected from SH, OH and NY 2Group; Can be independently selected from hydrogen and saturated and unsaturated, linear, aromatics, branching and cyclic hydrocarbon group with Y, wherein each can be unsubstituted or by at least one replacement of hydroxyl, nitro, amino and cyano group.
It only is exemplary and indicative should understanding above and following description, not the present invention of requirement for restriction protection.
Table herein illustrates all respects of the present invention, and is used from explanation principle of the present invention with description one.
Embodiment
Interest to the oiliness additive that is used for gasoline and diesel oil fuel is increasing always.This is subjected to the new demand of diesel oil fuel oilness (is used high-frequency reciprocating device (HighFrequency Reciprocating Rig, the maximum 520 μ m wear scar diameters of ASTM HFRR)) and the demand of the gasoline dope that improves fuel economy is driven.Imidazolinium compounds described herein can effectively reduce the friction and wear from fuel combustion, and this fuel comprises gasoline, diesel oil and biodiesel fuel.
Following embodiment is disclosed at this.
1. 1 kinds of fuel lubricity additives of scheme comprise the tetrahydroglyoxaline of following formula:
Figure A20071000587000061
Wherein:
That R is selected from is saturated and unsaturated, linear, aromatics, branching and cyclic hydrocarbon group, and it is unsubstituted or by at least one replacement of hydroxyl, nitro, amino and cyano group;
R ' is independently selected from hydrogen, hydroxyl, nitro, amino, cyano group and saturated and unsaturated, linear, aromatics, branching and cyclic hydrocarbon group;
A is selected from SH, OH and NY 2Group; With
Y is independently selected from hydrogen and saturated and unsaturated, linear, aromatics, branching and cyclic hydrocarbon group, and it is unsubstituted or by at least one replacement of hydroxyl, nitro, amino and cyano group.
Scheme 2. is according to the fuel lubricity additives of scheme 1, and wherein to be selected from the alkyl and the A that contain 10-20 carbon atom be amino to R.
Scheme 3. is according to the fuel lubricity additives of scheme 1, and wherein R ' is that hydrogen and A are NH 2
Scheme 4. is according to the fuel lubricity additives of scheme 1, wherein A be selected from-SH ,-OH and-NY 2Group.
5. 1 kinds of fuel lubricity additives that comprise tetrahydroglyoxaline of scheme, wherein this tetrahydroglyoxaline is prepared by the method that comprises the steps: the compound that makes formula (I):
Figure A20071000587000071
Compound reaction with formula (II):
Figure A20071000587000072
To obtain the tetrahydroglyoxaline of formula (IH):
Wherein:
That R is selected from is saturated and unsaturated, linear, aromatics, branching and cyclic hydrocarbon group, and is unsubstituted or by at least one replacement of hydroxyl, nitro, amino and cyano group;
R ' is independently selected from hydrogen, hydroxyl, nitro, amino, cyano group and saturated and unsaturated, linear, aromatics, branching and cyclic hydrocarbon group;
A is selected from-SH, OH and NY 2Group; With
Y is independently selected from hydrogen and saturated and unsaturated, linear, aromatics, branching and cyclic hydrocarbon group, and its each be unsubstituted or by at least one replacement of hydroxyl, nitro, amino and cyano group.
Scheme 6. is according to the fuel lubricity additives of scheme 5, and wherein R is selected from the alkyl that contains 10-20 carbon atom.
Scheme 7. is according to the fuel lubricity additives of scheme 5, and wherein R ' is a hydrogen.
Scheme 8. is according to the fuel lubricity additives of scheme 5, wherein A be selected from-SH ,-OH and-NH 2Group.
Scheme 9. is according to the fuel lubricity additives of scheme 5, wherein compound (I) and (II) with 1: 2-2: 1 mol ratio one reacts.
Scheme 10. is according to the fuel lubricity additives of scheme 5, wherein compound (I) and (II) with 0.8: 1-1: 0.8 mol ratio one reacts.
Scheme 11. is according to the fuel lubricity additives of scheme 5, and wherein fuel is diesel oil fuel.
Scheme 12. is according to the fuel lubricity additives of scheme 5, and wherein fuel is biodiesel fuel.
Scheme 13. is according to the fuel lubricity additives of scheme 5, and wherein fuel is gasoline.
Scheme 14. is according to the fuel lubricity additives of scheme 5, and wherein R is selected from linear thiazolinyl.
Scheme 15. is according to the fuel lubricity additives of scheme 5, and the compound of its Chinese style (I) is selected from 9,10-decylenic acid, octylenic acid, linolic acid, naphthenic acid and ready denier oil acid.
Scheme 16. is according to the fuel lubricity additives of scheme 5, and the compound of its Chinese style (II) is selected from quadrol, amino ethyl ethanolamine and diethylenetriamine.
Scheme 17. is according to the fuel lubricity additives of scheme 5, and the compound of its Chinese style (I) is that the compound of Unimac 5680 and formula (II) is an amino ethyl ethanolamine.
Scheme 18. is according to the fuel lubricity additives of scheme 5, and the compound of its Chinese style (I) is that the compound of naphthenic acid and formula (II) is an amino ethyl ethanolamine.
Scheme 19. is according to the fuel lubricity additives of scheme 5, and the compound of its Chinese style (I) is that the compound of Unimac 5680 and formula (II) is a diethylenetriamine.
Scheme 20. is according to the fuel lubricity additives of scheme 5, and the compound of its Chinese style (I) is that the compound of ready denier oil acid and formula (II) is a diethylenetriamine.
Scheme 21. is according to the fuel lubricity additives of scheme 5, and the compound of its Chinese style (I) is that the compound of Unimac 5680 and formula (II) is a diethylenetriamine.
Scheme 22. is according to the fuel lubricity additives of scheme 5, and the compound of its Chinese style (I) is that the compound of ready denier oil acid and formula (II) is an amino ethyl ethanolamine.
Scheme 23. is according to the fuel lubricity additives of scheme 5, and wherein said tetrahydroglyoxaline prepares under the batch technology condition.
Scheme 24. is according to the fuel lubricity additives of scheme 5, and wherein said tetrahydroglyoxaline prepares under the continuous processing condition.
25. 1 kinds of fuel compositions of scheme comprise:
(A) fuel of main quantity; With
(B) a spot of fuel lubricity additives according to scheme 1.
Scheme 26. is according to the fuel composition of scheme 25, and wherein fuel is gasoline or gasoline-pure blend.
Scheme 27. is according to the fuel composition of scheme 25, and wherein fuel is diesel oil fuel or diesel oil fuel-pure blend.
Scheme 28. is according to the fuel composition of scheme 25, and wherein fuel is biodiesel fuel.
Scheme 29. is according to the fuel composition of scheme 25, and wherein fuel comprises diesel oil fuel and water or alcoholic acid emulsion.
Scheme 30. further comprises at least a following material according to the fuel composition of scheme 25: dispersion agent, washing composition, oxygenation agent (oxygenates), oxidation inhibitor, carrier fluid, metal passivator, dyestuff, marking agent, pour point reducer, inhibiter, sterilant, cetane improving agent, anti static additive, stablizer, antifoams, viscosity depressant, emulsion splitter, antifogging agent, anti-icing agent, antiknock dope, anti-valve seat are return additive, other oiliness additive and combustion improving agent.
31. 1 kinds of anti-wear compositions of scheme comprise the fuel lubricity additives according to scheme 1, and wherein the quantity of this fuel lubricity additives existence is enough to reduce the wearing and tearing in the oil engine.
The friction of 32. 1 kinds of schemes improves compositions, comprises the fuel lubricity additives according to scheme 1, and wherein the quantity that exists in fuel of this fuel lubricity additives is enough to improve the friction of fuel.
33. 1 kinds of methods of improving the oilness of fuel composition in the engine of scheme comprise and adopt this engine of fuel handling that comprises according to the fuel lubricity additives of scheme 1.
34. 1 kinds of methods of improving the oilness of fuel composition in the engine of scheme comprise that employing operates this engine according to the fuel composition of scheme 25.
Scheme 35. is according to the method for scheme 34, and wherein said fuel composition comprises gasoline.
Scheme 36. is according to the method for scheme 34, and wherein said fuel composition comprises diesel oil fuel.
Scheme 37. is according to the method for scheme 34, and wherein said fuel composition comprises biodiesel fuel.
38. 1 kinds of methods of improving the automotive fuel economy of scheme, comprise use according to the fuel composition of scheme 25 as the fuel in the oil engine, wherein with adopt same way as and use the engine that does not have the equal fuel of fuel lubricity additives in the fuel just and operate to compare, the quantity that fuel lubricity additives exists is enough to improve the fuel economy of the oil engine of the described fuel composition of use.
Scheme 39. is according to the method for scheme 38, and wherein the quantity that exists in fuel composition of fuel lubricity additives is 25-150ptb.
Scheme 40. is according to the method for scheme 38, and wherein the quantity that exists in fuel composition of fuel lubricity additives is 40-60ptb.
41. 1 kinds of methods that reduce to wear and tear in the oil engine of scheme, comprise the fuel of the fuel composition of operational version 25 as oil engine, wherein with adopt same way as and use the engine that does not have the equal fuel of fuel lubricity additives in the fuel just and operate to compare, the quantity that fuel lubricity additives exists is enough to reduce the wearing and tearing of using in the oil engine that described fuel composition operates.
Scheme 42. is according to the method for scheme 41, and wherein the quantity that exists in fuel composition of fuel lubricity additives is 25-150ptb.
Scheme 43. is according to the method for scheme 41, and wherein the quantity that exists in fuel composition of fuel lubricity additives is 40-60ptb.
Scheme provides the improved method of friction in the oil engine for 44. 1 kinds, comprise the fuel of the fuel composition of operational version 25 as oil engine, wherein with adopt same way as and use the engine that does not have the equal fuel of fuel lubricity additives in the fuel just and operate to compare, the quantity that fuel lubricity additives exists is enough to improve the fuel friction of using in the oil engine that described fuel composition operates.
Scheme 45. is according to the method for scheme 44, and wherein the quantity that exists in fuel composition of fuel lubricity additives is 25-150ptb.
Scheme 46. is according to the method for scheme 44, and wherein the quantity that exists in fuel composition of fuel lubricity additives is 40-60ptb.
Tetrahydroglyoxaline as fuel lubricity additives can be expressed from the next:
Figure A20071000587000101
Wherein R can be selected from saturated and unsaturated, linear, aromatics, branching and cyclic hydrocarbon group, and it can be by at least one further replacement of hydroxyl, nitro, amino and cyano group; R ' can be independently selected from hydrogen, hydroxyl, nitro, amino, cyano group and saturated and unsaturated, linear, aromatics, branching and cyclic hydrocarbon group; A can be selected from SH, OH and NY 2Group; Can be independently selected from hydrogen and saturated and unsaturated, linear, aromatics, branching and cyclic hydrocarbon group with Y, its each can be unsubstituted or by at least one replacement of hydroxyl, nitro, amino and cyano group.
The tetrahydroglyoxaline of formula (IH) can be by making appropriate organic and polyamine, as diamine or tertiary amine prepared in reaction, its each can be by other group, for example hydroxyl replaces.Reaction can be included in and eliminate two molecular waters between acid and the amine.Reaction can be represented by following reaction formula:
The acid that is used to prepare tetrahydroglyoxaline comprise can with the polyamine reaction to form those of tetrahydroglyoxaline, for example by those of following formula (I) expression:
Wherein R is selected from saturated and unsaturated, linear, aromatics, branching and cyclic hydrocarbon group, and its each be unsubstituted or by at least one replacement of hydroxyl, nitro, amino and cyano group.The monocarboxylic acid that comprises the optional replacement that contains about at the most 25 carbon atoms for the appropriate acid of present disclosure purpose.Non-limitative example comprises unsaturated organic acid as 9,10-decylenic acid, octylenic acid, oleic acid, linolic acid etc.Other suitable acid comprises isooleic acid, Unimac 5680 and ready denier oil acid (for example being mainly the commercial mixture of oleic acid and linolic acid, stearic acid and other material well known by persons skilled in the art) and naphthenic acid.
When being included in organic acid reaction, suitable polyamine forms those of tetrahydroglyoxaline.According to some aspect of present disclosure, polyamine can be represented by formula (II):
Figure A20071000587000113
R ' can be independently selected from hydrogen, hydroxyl, nitro, amino, cyano group and saturated and unsaturated, linear, aromatics, branching and cyclic hydrocarbon group; A can be selected from SH, OH and NY 2Group; Can be independently selected from hydrogen and saturated and unsaturated, linear, aromatics, branching and cyclic hydrocarbon group with Y, its each can be unsubstituted or by at least one replacement of hydroxyl, nitro, amino and cyano group.The non-limitative example that is suitable for the polyamine of present disclosure purpose comprises hydroxyethylethylene diamine, quadrol, amino ethyl ethanolamine, diethylenetriamine, hydroxyethyl diethylenetriamine etc.
Fuel lubricity additives disclosed herein comprises that at least a imidazolinium compounds and at least a solvent of choosing wantonly or solubility promoter are to be used for for example promoting the processing and the blend of compound.Suitable solvent comprises alcohol (as methyl alcohol, ethanol, Virahol, 2-Ethylhexyl Alcohol), ketone (acetone, methylethylketone), ester (tert.-butyl acetate) and ether (as methyl tertiary butyl ether).Aromatic hydrocarbons also can be useful solvent, as Aromatic 100-150.The suitable non-limitative example of aromatic hydrocarbon comprises benzene, toluene and/or dimethylbenzene and high-molecular weight aromatic solvent more.
According to an aspect of present disclosure, solvent is the commercial blend of aromatic substances.Acid is 1 with the mol ratio of amine in one embodiment: 2-3: 1 and be 1 in another embodiment: 2-2: 1.Useful especially is 1: 1-2: 1 acid and amine ratio.
Present disclosure also relates to fuel composition, and said composition comprises fuel and a spot of fuel lubricity additives disclosed herein of main quantity.By non-limitative example, suitable fuel comprises diesel oil fuel, biodiesel fuel, gasoline emulsion, diesel oil emulsion, gasoline-pure blend, diesel oil-pure blend, gasoline and composition thereof.Fuel lubricity additives can think that fuel provides the concentration of required oilness to use.Useful scope can be about 5000 pounds of for example about 1-per thousand barrels (ptb), for example 5-2000ptb, or 5-500ptb.Fuel lubricity additives can be stored subsequently at refinery or any, the transportation (as pipeline) or (as the pumping plant) stage of conveying join in gasoline or the diesel oil fuel.It can be fabricated to back market gasoline or diesel-dope and be sold to the user through sales counter with packing material, and the user directly joins it in the tanks then.
Diesel oil fuel can comprise any various mixtures that can be used as the hydrocarbon of diesel oil fuel, therefore and comprise overhead product and residual fuel oil, the blend of residual fuel oil and overhead product, gas oil, the cycle stock of operating from cracking and the blend of straight run and cracked distillate.Biofuel is called as the alternate diesel oil fuel for a long time always and can for example experiences various filtration known to a person of ordinary skill in the art and abstraction technique acquisition by making from the oil of oily seed acquisition.
Fuel composition disclosed herein can comprise at least a other composition except that fuel and fuel lubricity additives.For example, fuel composition can comprise at least a following material: dispersion agent, washing composition, oxygenation agent, oxidation inhibitor, carrier fluid, metal passivator, dyestuff, marking agent, pour point reducer, inhibiter, sterilant, cetane improving agent, anti static additive, stablizer, antifoams, viscosity depressant, emulsion splitter, antifogging agent, anti-icing agent, antiknock dope, anti-valve seat are return additive, other oiliness additive and combustion improving agent.The oxygenation agent can be for example and comprise methyl alcohol, ethanol, ester, ether, fuel modification agent and antiknock material without limitation at this.Useful especially at this is other antiknock component methyl cyclopentadienyl tricarbonyl manganese, for example with the level of every liter of fuel of 20-200 milligram.
Embodiment
Adopt different beginning materials to use following reaction scheme to prepare several compounds:
Figure A20071000587000131
Wherein R is that saturated or unsaturated, aromatics, branching or linear alkyl and A are OH or NH 2The compound of producing according to reaction scheme A is known as the additive that is suitable for improving gasoline and diesel oil fuel oilness, and therefore compares with the fuel lubricity additives of producing according to option b of the present invention.
The test synthetic materials reduces the ability of friction and wear in gasoline and the diesel oil fuel in high-frequency reciprocating device (HFRR).HFRR equipment and the method used are as described below: steel ball is connected on the oscillating arms assembly and with the HFRR sample pool in steel disk sample coupling.Sample pool comprises the fuel of 2ml test, and sample is remained in the bath, for diesel oil under 60 ℃ temperature, and for gasoline under 25 ℃ temperature.With statical load 200 loads that restrain are applied to ball/dish interface.With ball component on the 1mm path with 50 hertz rate oscillation.These conditions guarantee not accumulation between ball and dish of fluid film.At specific time (for example 75 minutes) afterwards, take out steel ball component.Evaluate wearing and tearing and fuel lubricity therefore by the average abrasion scar diameter of measuring on the ball that contacts from vibration with dish.The wear scar that obtains is more little, and the oilness of fuel is big more.Low-friction coefficient and low wear scar are the proofs of good lubrication effect.
The HFRR performance of many additives in gasoline that table 1 relatively uses two kinds of reaction scheme to produce.The material that uses the present invention program B to produce by identical starting acid as one man surpasses the contrast fuel lubricity additives that operational version A produces.The friction co-efficient value that provides in table 1 and 2 is the mean value in test in whole 75-minute.
Table 1
The HFRR of test oiliness additive in gasoline
Fuel Additive chemistry Reaction scheme Processing rate (PTB) Frictional coefficient * Wear scar (um)
G1 -- -- -- 0.299 485
G1 Unimac 5680/DEA A 50 0.219 365
G1 Isooleic acid/DEA A 50 0.237 445
G1 Isooleic acid/DEA A 50 0.235 430
G1 Naphthenic acid/DEA A 50 0.276 515
G1 Isooleic acid/DEA A 100 0.200 342.5
G1 Unimac 5680/AEEA B 50 0.216 370
G1 Naphthenic acid/AEEA B 50 0.235 370
G1 Unimac 5680/DETA B 50 0.213 325
G2 -- -- -- 0.434 780
G2 Unimac 5680/DEA A 100 0.236 438
G2 Unimac 5680/AEEA B 100 0.223 325
G2 Unimac 5680/AEEA B 50 0.254 400
*Frictional coefficient=F/P, wherein F is that frictional force and the P that measures is the load that applies
Isooleic acid=Century 1164 isooleic acid are from Arizona Chemical Company
Unimac 5680=Century 1105 Unimac 5680s are from Arizona Chemical CompanyNap Acid=naphthenic acid, from Merrichem Company
The DEA=diethanolamine
The AEEA=amino ethyl ethanolamine
The DETA=diethylenetriamine
The G1=natural petrol is from Sunoco
The G2=natural petrol is from Citgo
Fuel 1 and 2 is typical U.S. natural petrols.
Result in the table 1 shows, compares with the fuel lubricity additives that is prepared by option A, and fuel lubricity additives of the present invention can significantly improve the oilness of fuel.
The ultra-low-sulphur diesel fuel gasoline replacing that use obtains from the U.S. refinery carries out the HFRR test once more.Table 2 shows that the excellent properties from the option b fuel lubricity additives extends to diesel oil fuel.
Table 2
The HFRR of test oiliness additive in diesel oil fuel
Fuel Additive chemistry Reaction scheme Processing rate (PTB) Frictional coefficient * Wear scar (um)
ULSD1 Basic fuel-additive-free -- -- 0.391 637.5
ULSD1 TOFA -- 100 0.230 435
ULSD1 TOFA/DEA A 100 0.213 380
ULSD1 Unimac 5680/AEEA B 100 0.230 417
ULSD1 TOFA/DETA B 100 0.253 480
ULSD1 TOFA/AEEA B 100 0.244 460
*Frictional coefficient=F/P, wherein F is that frictional force and the P that measures is the load that applies
ULSD1=ultra-low-sulphur diesel fuel is from Conoco Phillips
Unimac 5680=Century 1105 Unimac 5680s are from Arizona Chemical Company
The TOFA=ready denier oil acid is from Arizona Chemical Company
The DEA=diethanolamine
The AEEA=amino ethyl ethanolamine
The DETA=diethylenetriamine
Table 2 shows, non-sample 1-3 of the present invention is incorporated into wear scar diameter that obtains in the diesel oil fuel and the embodiment that comprises sample 4-7 of the present invention.
Consider specification sheets of the present invention disclosed herein and enforcement, the others of present disclosure are obvious to those skilled in the art.Wish only to think that specification sheets and embodiment only are exemplary that true model circle of the present invention and spirit are by following claim indication.

Claims (10)

1. fuel lubricity additives comprises the tetrahydroglyoxaline of following formula:
Wherein:
That R is selected from is saturated and unsaturated, linear, aromatics, branching and cyclic hydrocarbon group, and it is unsubstituted or by at least one replacement of hydroxyl, nitro, amino and cyano group;
R ' is independently selected from hydrogen, hydroxyl, nitro, amino, cyano group and saturated and unsaturated, linear, aromatics, branching and cyclic hydrocarbon group;
A is selected from SH, OH and NY 2Group; With
Y is independently selected from hydrogen and saturated and unsaturated, linear, aromatics, branching and cyclic hydrocarbon group, and it is unsubstituted or by at least one replacement of hydroxyl, nitro, amino and cyano group.
2. according to the fuel lubricity additives of claim 1, wherein to be selected from the alkyl and the A that contain 10-20 carbon atom be amino to R.
3. according to the fuel lubricity additives of claim 1, wherein R ' is that hydrogen and A are NH 2
4. according to the fuel lubricity additives of claim 1, wherein A be selected from-SH ,-OH and-NY 2Group.
5. fuel lubricity additives that comprises tetrahydroglyoxaline, wherein this tetrahydroglyoxaline is by the method preparation that comprises the steps: the compound that makes formula (I):
Figure A2007100058700002C2
Compound reaction with formula (II):
Figure A2007100058700002C3
To obtain the tetrahydroglyoxaline of formula (III):
Figure A2007100058700003C1
Wherein:
That R is selected from is saturated and unsaturated, linear, aromatics, branching and cyclic hydrocarbon group, and is unsubstituted or by at least one replacement of hydroxyl, nitro, amino and cyano group;
R ' is independently selected from hydrogen, hydroxyl, nitro, amino, cyano group and saturated and unsaturated, linear, aromatics, branching and cyclic hydrocarbon group;
A is selected from-SH, OH and NY 2Group; With
Y is independently selected from hydrogen and saturated and unsaturated, linear, aromatics, branching and cyclic hydrocarbon group, and its each be unsubstituted or by at least one replacement of hydroxyl, nitro, amino and cyano group.
6. according to the fuel lubricity additives of claim 5, the compound of its Chinese style (I) is selected from 9,10-decylenic acid, octylenic acid, linolic acid, naphthenic acid and ready denier oil acid.
7. according to the fuel lubricity additives of claim 5, the compound of its Chinese style (II) is selected from quadrol, amino ethyl ethanolamine and diethylenetriamine.
8. a fuel composition comprises
(A) fuel of main quantity; With
(B) a spot of fuel lubricity additives according to claim 1.
9. method of improving the automotive fuel economy, comprise that use fuel composition according to Claim 8 is as the fuel in the oil engine, wherein with adopt same way as and use the engine that does not have the equal fuel of fuel lubricity additives in the fuel just and operate to compare, the quantity that fuel lubricity additives exists is enough to improve the fuel economy of the oil engine of the described fuel composition of use.
10. method that reduces to wear and tear in the oil engine, comprise the fuel composition that uses claim 8 fuel as oil engine, wherein with adopt same way as and use the engine that does not have the equal fuel of fuel lubricity additives in the fuel just and operate to compare, the quantity that fuel lubricity additives exists is enough to reduce the wearing and tearing of using in the oil engine that described fuel composition operates.
CNA2007100058708A 2006-02-21 2007-02-25 Fuel lubricity additives Pending CN101024787A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101423782B (en) * 2007-11-02 2013-01-09 上海焦化有限公司 Dimethyl ether fuel lubricant
CN114364771A (en) * 2019-06-28 2022-04-15 道达尔能源销售服务公司 Lubricant composition for preventing corrosion and/or fretting corrosion of metal components in engines

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BRPI0718271A2 (en) * 2006-10-18 2013-11-12 Lean Flame Inc GAS AND FUEL PREMIXER FOR USE IN COMBINATION WITH THE ENERGY RELEASE / CONVERSION DEVICE
GR1006805B (en) * 2009-02-26 2010-06-16 Dorivale Holdings Limited, Biodiesel containing non-phenolic additives and thereby possesing enhanced oxidative stability and low acid number.
GB0909351D0 (en) * 2009-06-01 2009-07-15 Innospec Ltd Improvements in efficiency
WO2011031278A1 (en) 2009-09-13 2011-03-17 Lean Flame, Inc. Inlet premixer for combustion apparatus
US11390821B2 (en) * 2019-01-31 2022-07-19 Afton Chemical Corporation Fuel additive mixture providing rapid injector clean-up in high pressure gasoline engines
EP4092099A1 (en) * 2021-05-20 2022-11-23 TUNAP GmbH & Co. KG Bioactive additive for fuel and uses thereof, fuel composition and method
WO2023183460A1 (en) 2022-03-23 2023-09-28 Innospec Fuel Specialities Llc Compositions, methods and uses

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3036902A (en) * 1958-03-03 1962-05-29 Standard Oil Co Motor fuel composition
US3527583A (en) * 1966-04-25 1970-09-08 Gulf Research Development Co Motor fuel multipurpose agents
US3615291A (en) * 1966-04-25 1971-10-26 Gulf Research Development Co Ethoxylated or propoxylated 1,2,4- or 1,2,5-trisubstituted imidazolines and lecithin mixtures and reaction products thereof
US3582295A (en) * 1967-04-07 1971-06-01 Ethyl Corp Gasoline anti-icing
US3644393A (en) * 1969-08-29 1972-02-22 Gulf Research Development Co Lecithin mixtures and reaction products of 1 2-disubstituted imidazoline
US4247300A (en) * 1978-04-27 1981-01-27 Phillips Petroleum Company Imidazoline fuel detergents
US4292046A (en) * 1979-08-10 1981-09-29 Mobil Oil Corporation Detergent compositions
US4273665A (en) * 1979-10-09 1981-06-16 Mobil Oil Corporation Friction reducing additives and compositions thereof
US4298486A (en) * 1979-11-23 1981-11-03 Mobil Oil Corporation Friction reducing additives and compositions thereof
US4518782A (en) * 1981-08-10 1985-05-21 Texaco Inc. Fuel compositions containing N-alkyl glycyl imidazoline
US4536311A (en) * 1983-12-27 1985-08-20 Mobil Oil Corporation Multipurpose antirust and friction reducing additives and compositions thereof
US4511367A (en) * 1984-06-13 1985-04-16 Ethyl Corporation Corrosion inhibitors for alcohol containing motor fuel
CA1263913A (en) * 1984-06-13 1989-12-19 Gordon G. Knapp Corrosion inhibitors for alcohol-based fuels
US4797134A (en) * 1987-08-27 1989-01-10 Wynn Oil Company Additive composition, for gasoline
GB2239258A (en) * 1989-12-22 1991-06-26 Ethyl Petroleum Additives Ltd Diesel fuel compositions containing a manganese tricarbonyl
US5024677A (en) * 1990-06-11 1991-06-18 Nalco Chemical Company Corrosion inhibitor for alcohol and gasohol fuels
US5833721A (en) * 1993-08-03 1998-11-10 Exxon Chemical Patents Inc Additive for hydrocarbon oils
US6562086B1 (en) * 1997-06-26 2003-05-13 Baker Hughes Inc. Fatty acid amide lubricity aids and related methods for improvement of lubricity of fuels
JP4383660B2 (en) * 1998-01-13 2009-12-16 ベイカー ヒューズ インコーポレイテッド Compositions and methods for improving the lubricity of fuels
US20030056431A1 (en) * 2001-09-14 2003-03-27 Schwab Scott D. Deposit control additives for direct injection gasoline engines

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101423782B (en) * 2007-11-02 2013-01-09 上海焦化有限公司 Dimethyl ether fuel lubricant
CN114364771A (en) * 2019-06-28 2022-04-15 道达尔能源销售服务公司 Lubricant composition for preventing corrosion and/or fretting corrosion of metal components in engines

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