• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    The invention relates to a lubricating additive for fuels which comprises an imidazoline. The additive is prepared by reacting an optionally substituted organic acid with an optionally substituted polyamine. Field of application: Use of this additive in fuel compositions comprising a fuel and the additive, to reduce wear in an engine.
    公开号:BE1018136A3
    申请号:E2007/0076
    申请日:2007-02-20
    公开日:2010-06-01
    发明作者:Scott D Schwab；Joshua J Bennett
    申请人:Afton Chemical Corp；
    IPC主号:
    专利说明:

    Productivity additives for fuels, and fuel compositions containing them
    The present disclosure relates to a lubricating additive for fuels, comprising an imidazoline. The fuel lubricity additive to be useful for improving the lubricity of fuels and reducing wear in internal combustion engines.
    In order to reduce pollution and conserve energy, automobiles are constantly upgraded to be able to travel greater mileage for a given amount of gasoline. This effort is a result, at least in part, of government regulations to force automobile manufacturers to achieve prescribed mileage based on a given amount of gasoline. In an attempt to achieve the mileage required, one way is to reduce the dimensions of a number of automobiles. However, there are limits to this approach beyond which automobiles can no longer be suitable for an average family. Another way to improve mileage for a given amount of fuel is to reduce engine wear that can be attributed in part to friction in the engine. This memo relates to fuel lubricity additives for petrol and diesel fuels, as well as methods for reducing engine wear.
    It is known to use imidazoline derivatives in fuels to modify engine performance, for example as detergents and anti-corrosion agents, and to minimize fuel vaporization. The U.S. Patent No. 3,036,902 discloses certain imidazoline derivatives which are useful for reducing the icing frequency of carburetors. The derivatives are combined with an alkanol to form a deicing composition. There is no mention, among others, additives of lubricity.
    The U.S. Patent No. 6,562,086 discloses a lubricity additive for diesel fuels and fuels for spark ignition engines containing an alkanolamide of a fatty acid, an alkanolamide of a modified fatty acid for one of their mixtures. The preparation of alkanolamides as additives for lubricity is known. However, alkanolamides can not be as effective in reducing engine wear as the fuel lubricity additives herein.
    According to the present invention, there is provided a lubricating additive for fuels, comprising an imidazoline corresponding to the following formula:
    wherein R may be selected from linear, aromatic, branched and cyclic, saturated and unsaturated hydrocarbyl groups, which may be unsubstituted or substituted with at least one of hydroxyl, nitro, amino and cyano; R 'may be independently selected from hydrogen, hydroxyl, nitro, amino and cyano, and linear, aromatic, branched and cyclic, saturated and unsaturated hydrocarbyl groups; A may be selected from SH, OH and NY2, and Y may be independently selected from hydrogen, linear, aromatic, branched and cyclic, saturated and unsaturated hydrocarbyl groups, each of which may be unsubstituted or substituted, with at least one of the hydroxyl, nitro, amino and cyano groups. The term "amino" herein refers to any mono-, di-, tri- and polyamines and mixtures thereof.
    In another aspect of this specification, there is provided a fuel lubricity additive comprising imidazoline, wherein the imidazoline additive can be prepared by a process comprising reacting a compound of formula (I):
    (D
    with a compound of formula (II):
    (H) giving an imidazoline of formula (III):
    (III) wherein R may be selected from linear, aromatic, branched and cyclic, saturated and unsaturated hydrocarbyl groups, which may be unsubstituted or substituted with at least one of hydroxyl, nitro, amino and cyano; R 'may be independently selected from hydrogen, hydroxyl, nitro, amino and cyano groups and linear, aromatic, branched and cyclic, saturated and unsaturated hydrocarbyl groups; A may be selected from SH, OH and NY2 and Y may be independently selected from hydrogen, linear, aromatic, branched and cyclic, saturated and unsaturated hydrocarbyl groups, each of which may be unsubstituted or substituted with at least one one of the hydroxyl, nitro, amino and cyano groups.
    It should be understood that the foregoing description and the following description are merely illustrative and explanatory and do not limit the invention as claimed.
    The tables herein illustrate aspects of the invention and, together with the description, serve to explain the principles of the invention.
    The interest in lubricity additives for gasoline and diesel fuel has increased. This interest was stimulated by the new requirements imposed on the lubricating power of diesel fuel (maximum ASTM wearing hight diameter of 520 μm using a high frequency reciprocating frame (HFRR)) and the need for additives for gasoline that improve fuel economy. The imidazoline derivatives disclosed herein can be effective in reducing the friction and wear resulting from the combustion of fuels, including gasoline, diesel fuel and biodiesel fuel.
    The imidazolines useful as additives for lubricity for fuels can be represented by the following general formula:
    (III) wherein R may be selected from linear, aromatic, branched and cyclic, saturated and unsaturated hydrocarbyl groups, which may be further substituted with at least one of hydroxyl, nitro, amino and cyano; R 'may be independently selected from hydrogen, hydroxyl, nitro, amino and cyano groups and linear, aromatic, branched and cyclic, saturated and unsaturated hydrocarbyl groups; A may be selected from SH, OH and NY2 groups; and Y may be independently selected from hydrogen, linear, aromatic, branched and cyclic, saturated and unsaturated hydrocarbyl groups, each of which may be unsubstituted or substituted with at least one of hydroxyl, nitro, amino and cyano groups.
    The imidazolines of formula (III) can be obtained by reacting a suitable organic acid with a polyamine, such as a diamine or a triamine, each of which may be substituted with other groups such as, for example, hydroxyl groups. The reaction may include removing water molecules between the acid and the amine. The reaction can be represented by the following equation:
    Acids that are useful in the preparation of imidazolines include those that are capable of reacting with a polyamine to form an imidazoline, such as those represented by the following formula (I):
    Wherein R may be selected from linear, aromatic, branched and cyclic, saturated and unsaturated hydrocarbyl groups, each unsubstituted or substituted with at least one of hydroxyl, nitro, amino and cyano groups. Suitable acids for the purposes of this specification include optionally substituted monocarboxylic acids having up to about 25 carbon atoms. Non-limiting examples include unsaturated organic acids such as 9,10-decylenic acid, octenoic acid, oleic acid, linoleic acid, and the like. Other suitable acids include isoolic acid, isostearic acid, and tall oil fatty acid (e.g., commercial mixtures consisting primarily of oleic acids and linoleic acids, stearic acid, and other acids). known to those skilled in the art) and naphthenic acid.
    Suitable polyamines include those that form an imidazoline by reaction with an organic acid. In some aspects of this specification, the polyamines may be represented by formula (II):
    R 'may be independently selected from hydrogen, hydroxyl, nitro, amino and cyano groups and linear, aromatic, branched and cyclic, saturated and unsaturated hydrocarbyl groups; A may be selected from SH, OH and NY2 groups; and Y may be independently selected from hydrogen, linear, aromatic, branched and cyclic, saturated and unsaturated hydrocarbyl groups, each of which may be unsubstituted or substituted with at least one of hydroxyl, nitro, amino and cyano groups. Non-limiting examples of polyamines suitable for the purpose of this specification include hydroxyethylethylenediamine, ethylene diamine, aminoethylethanolamine, diethylenetriamine, hydroxyethyl diethylenetriamine, and the like.
    The fuel lubricity additives described herein comprise at least one imidazoline derivative and, optionally, at least one solvent or co-solvent, for example to facilitate handling and mixing of the compound. Suitable solvents include alcohols (eg methanol, ethanol, isopropanol, 2-ethyl hexanol, ketones (acetone, methyl ethyl ketone), esters (t-butyl acetate) and ethers). (e.g., tert-butyl methyl ether) Aromatic hydrocarbons may also be useful solvents, an example being Aromatic 100-150 Suitable nonlimiting examples of aromatic hydrocarbons include benzene, toluene and / or xylene and aromatic solvents of higher molecular weight.
    In one aspect of the disclosure, the solvent is a commercial mixture of aromatic compounds. The molar ratio of acid to amine is generally from 1: 2 to 3: 1 in one embodiment, and from 1: 2 to 2: 1 in another embodiment. Particularly useful amine to amine ratios are from 1: 1 to 2: 1.
    The present disclosure relates to fuel compositions comprising a fuel in a major amount, and the fuel lubricity additive described herein in a small amount. Suitable fuels include, by way of non-limiting example, diesel fuel, biodiesel fuel, gasoline emulsions, diesel fuel emulsions, gasoline-alcohol mixtures, diesel-alcohol fuel blends, gasoline and their mixtures. The fuel lubricity additive can be used in a concentration that gives the fuel the desired degree of lubricity. A useful range may range, for example, from about 0.00285 to about 14.25 kilograms per cubic meter (kg / m3), for example from 0.01425 to 5.7, or 0.01425 to 1.425 kg / m3. . The fuel additive may be added to gasoline or diesel fuel at the refinery or at any stage of the subsequent storage, transportation (eg pipeline), or distribution ( for example by service stations). It can be produced in the form of an additive for gasoline or diesel fuel after marketing, and put on free sale in a package for a user, who then introduces it directly into a fuel tank.
    The diesel fuel may comprise any of the various hydrocarbon mixtures that can be used as diesel fuels and thus includes residual distillate fuels and fuel oils, residual fuel oil mixtures with distillates, gas oils, and the like. oils, a recycling product from cracking operations and mixtures of straight-run distillates and cracking distillates. Biodiesel fuel has long been known as a replacement for diesel fuel and can be obtained, for example, by subjecting oil obtained from oil seeds to various filtration and extraction techniques well known to man of the art. art.
    The fuel compositions described herein may contain at least one additional ingredient, in addition to the fuel and the fuel lubricity additive. For example, the fuel compositions may comprise at least one additive consisting of dispersants, detergents, oxygenates, antioxidants, vehicle fluids, metal deactivators, dyes, labels, reducing agents, and the like. pour point, corrosion inhibitors, biocides, cetane improvers, antistatic additives, stabilizers, antifoaming agents, friction reducing agents, demulsifiers, antifoggants, anti-icing additives, anti-knock additives, valve seat anti-removal additives, additional lubricity additives and combustion improvers. Oxygen compounds herein may include, for example, and not limited to, methanol, ethanol, esters, ethers, combustion improvers and antiknock agents. A particularly useful agent herein is the additional antiknock ingredient methylcyclopentadienyl manganese tricarbonyl, for example, at a level of 20 to 200 milligrams per liter of fuel.
    Examples
    Several compounds have been prepared with different starting materials using the following reaction schemes:
    where R represents an aromatic, branched or linear alkyl group, saturated or unsaturated, and A represents OH or NH2. The compounds produced according to the reaction scheme A are known as additives suitable for modifying the lubricating power of gasoline and diesel fuel and, thus, have been compared with the fuel lubricity additives of the invention, produced according to the scheme. B.
    The synthesized substances have been tested in the High Frequency Reciprocating Frame (HFRR) for their ability to reduce friction and wear in gasoline and diesel fuel. The HFRR apparatus and the procedure used are described as follows: a steel ball is attached to a swing arm assembly and is coupled to a disk steel sample in the sample cell of the HFRR device. The sample cell contains 2 ml of the tested fluid and the sample is kept in a bath at a temperature of 60 ° C for diesel fuel, but 25 ° C for gasoline. A load of 200 g is applied to the ball / disc interface by dead weight. The ball assembly is oscillated in a path of 1 mm at a frequency of 50 Hz. These conditions ensure that a film of fluid does not accumulate between the ball and the disc. After a prescribed period (eg 75 minutes), the steel ball assembly is removed. The wear, and therefore the lubricity of the fuel, is determined by measuring the average diameter of the wear scar on the ball, resulting from the oscillating contact with the disc. The smaller the wear scar, the greater the lubricating power of the fuel. A low coefficient of friction and a small wear scar are proof of a good lubricating effect.
    Table 1 compares the HFRR performance in essence of a number of additives produced using both reaction schemes. The substances produced from the identical starting acids of the inventive scheme B consistently showed performance exceeding that of the comparative non-fatness additives for fuels produced using scheme A. The coefficient of friction values in Tables 1 and 2 are shown by an average during the total test of 75 minutes.
    Table 1
    * Coefficient of friction = F / P, where F represents the measured friction force and P represents the applied load Isoolic acid = Century 1164 isoolic acid from Arizona Chemical Company
    Isostearic acid = Century 1105 isostearic acid from Arizona Chemical Company
    Nap acid = Merrichem Company's naphthenic acid DEA = Diethanolamine AEEA = Aminoethyl-ethanolamine DETA = Diethylenetriamine
    Gl = essence without additive, of Sunoco G2 = essence without additive, of Citgo
    Fuels 1 and 2 are gasolines without conventional additives to E.O.A.
    The results in Table 1 demonstrate that the fuel lubricity additives of the invention can substantially improve the lubricity of a fuel, as compared to the lubricity additives for lubricants prepared by Scheme A.
    The HFRR test was again performed using an ultra-low sulfur diesel fuel obtained from an EUS refinery, instead of gasoline. Table 2 shows that the superior performance achieved by means of the fuel lubricity additives obtained in Scheme B extend to diesel fuel.
    Table 2
    * Coefficient of friction = F / P, where F represents the measured friction force and P represents the applied load ÜLSD1 - Ultra-low sulfur diesel fuel, from Conoco Phillips
    Isostearic acid = Century 1105 isostearic acid from Arizona Chemical Company TOFA = Tall oil fatty acid from Arizona Chemical Company DEA = diethanolamine AEEA = Aminoethyl-ethanolamine DETA = Diethylenetriamine
    Table 2 shows the diameters of the wear scars obtained by incorporation into the diesel fuel of the samples 1 to 3 not forming part of the present invention, and contains embodiments of the samples 4 to 7 of the present invention.
    Other aspects of this specification will become apparent to those skilled in the art by considering the description and practice of the invention described herein. It is believed that the description and examples are merely illustrative, the exact scope and spirit of the invention being indicated by the following claims.
    权利要求:
    Claims (46)
    [1]
    A lubricating additive for fuels, characterized in that it comprises an imidazoline corresponding to the following formula: embedded image in which:

    [2]
    2. Fuel lubricity additive according to claim 1, characterized in that R is selected from hydrocarbyl groups having 10 to 20 carbon atoms, and A represents an amino group.
    [3]
    3. Additive of lubricity for fuels according to claim 1, characterized in that R 'represents a hydrogen atom and A represents an NH 2 group.
    [4]
    4. Fuel additive according to claim 1, characterized in that A is selected from -SH, -OH and -NY2 groups.
    [5]
    5. Productivity additive for fuels, comprising an imidazoline, characterized in that said imidazoline is prepared by a process comprising the reaction of a compound of formula (I):

    [6]
    6. fuel lubricity additive according to claim 5, characterized in that R is selected from hydrocarbyl groups having 10 to 20 carbon atoms.
    [7]
    7. Additive of lubricity for fuels according to claim 5, characterized in that R 'represents a hydrogen atom.
    [8]
    A fuel lubricity additive according to claim 5, characterized in that A is selected from -SH, -OH and -NH 2 groups.
    [9]
    9. Fuel additive according to claim 5, characterized in that the compounds (I) and (II) are reacted together in a molar ratio of 1: 2 to 2: 1.
    [10]
    10. fuel lubricity additive according to claim 5, characterized in that the compounds (I) and (II) are reacted together in a molar ratio of 0.8: 1 to 1: 0.8.
    [11]
    Fuel additive according to Claim 5, characterized in that the fuel is a diesel fuel.
    [12]
    Fuel additive according to Claim 5, characterized in that the fuel is a biodiesel fuel.
    [13]
    Fuel additive according to Claim 5, characterized in that the fuel is petrol.
    [14]
    14. Fuel additive according to Claim 5, characterized in that R is chosen from linear alkenyl groups.
    [15]
    15. Additive of lubricity for fuels according to claim 5, characterized in that the compound of formula (I) is selected from 9,10-decylenic acid, octenoic acid, linoleic acid, naphthenic acid and the tall oil fatty acid.
    [16]
    16. Fuel additive for fuel according to claim 5, characterized in that the compound of formula (II) is selected from ethylenediamine, aminoethylethanolamine and diethylenetriamine.
    [17]
    17. Fuel additive for fuel according to claim 5, characterized in that the compound of formula (I) is isostearic acid and the compound of formula (II) is aminoethylethanolamine.
    [18]
    18. Fuel additive according to claim 5, characterized in that the compound of formula (I) is naphthenic acid and the compound of formula (II) is aminoethylethanolamine.
    [19]
    19. Fuel additive for fuels according to claim 5, characterized in that the compound of formula (I) is isostearic acid and the compound of formula (II) is diethylenetriamine.
    [20]
    20. Fuel additive for fuel according to claim 5, characterized in that the compound of formula (I) is a tall oil fatty acid and the compound of formula (II) is diethylenetriamine.
    [21]
    21. Fuel additive for fuel according to claim 5, characterized in that the compound of formula (I) is isostearic acid and the compound of formula (II) is diethylenetriamine.
    [22]
    22. Fuel additive for fuel according to claim 5, characterized in that the compound of formula (I) is a tall oil fatty acid and the compound of formula (II) is aminoethylethanolamine.
    [23]
    23. Fuel additive for fuel according to claim 5, characterized in that said imidazoline is prepared under batch process conditions.
    [24]
    24. Fuel additive according to claim 5, characterized in that said imidazoline is prepared under continuous process conditions.
    [25]
    25. Fuel composition, characterized in that it comprises: (A) a fuel in a dominant amount; and (B) a fuel lubricity additive according to claim 1 in a small amount.
    [26]
    26. Fuel composition according to claim 25, characterized in that the fuel is gasoline or a gasoline-alcohol mixture.
    [27]
    Fuel composition according to Claim 25, characterized in that the fuel is a diesel fuel or a diesel-alcohol fuel mixture.
    [28]
    28. Fuel composition according to claim 25, characterized in that the fuel is a biodiesel fuel.
    [29]
    29. Fuel composition according to claim 25, characterized in that the fuel comprises an emulsion of diesel fuel and water or ethanol.
    [30]
    30. Fuel composition according to claim 25, characterized in that it further comprises at least one of the agents consisting of dispersants, detergents, oxygenates, antioxidants, vehicle fluids, metal deactivators, dyes, labels, pour point depressants, corrosion inhibitors, biocides, cetane improvers, antistatic additives, stabilizers, antifoam agents, friction reducing agents, demulsifiers, antifoggants, anti-icing additives, anti-knock additives, valve seat anti-removal additives, additional lubricity additives and combustion improvers.
    [31]
    Antiwear composition comprising the fuel lubricity additive according to claim 1, characterized in that said fuel lubricity additive is present in an amount sufficient to reduce wear in an internal combustion engine.
    [32]
    A friction modifying composition comprising the fuel lubricity additive of claim 1 characterized in that said fuel lubricity additive is present in a fuel in an amount sufficient to modify the friction of the fuel.
    [33]
    33. Process for improving the lubricating power of a fuel composition in an engine, characterized in that it comprises the operation of said engine with a fuel comprising a fuel lubricity additive according to claim 1.
    [34]
    A process for improving the lubricity of a fuel composition in an engine, characterized in that it comprises operating said engine with a fuel composition according to claim 25.
    [35]
    35. The process according to claim 34, characterized in that said fuel composition comprises gasoline.
    [36]
    36. Process according to claim 34, characterized in that said fuel composition comprises a diesel fuel.
    [37]
    37. The process of claim 34, characterized in that said fuel composition comprises a biodiesel fuel.
    [38]
    A method for improving the fuel economy of an internal combustion engine comprising using as a fuel in the internal combustion engine the fuel composition according to claim 25, characterized in that the lubricity additive for fuels is present in an amount sufficient to improve the fuel economy of the internal combustion engine using the fuel composition, in comparison with the engine operating in the same manner and using the same fuel except that the fuel is free of the additive of lubricity for fuels.
    [39]
    39. A process according to claim 38, characterized in that the fuel lubricity additive is present in the fuel composition in an amount of 0.07125 to 0.4275 kg / m3.
    [40]
    40. Process according to claim 38, characterized in that the fuel lubricity additive is present in the fuel composition in an amount of 0.114 to 0.171 kg / m3.
    [41]
    A method for reducing wear in an internal combustion engine comprising using as the fuel for the internal combustion engine the fuel composition of claim 25, characterized in that the fuel lubricity additive is present in an amount sufficient to reduce wear in an internal combustion engine operating using the fuel composition, as compared to wear in the engine operating in the same manner and using the same fuel except that the fuel is free of fuel. additive of lubricity for fuels.
    [42]
    42. Process according to claim 41, characterized in that the fuel lubricity additive is present in the fuel composition in an amount of 0.07125 to 0.4275 kg / m3.
    [43]
    43. Process according to claim 41, characterized in that the fuel lubricity additive is present in the fuel composition in an amount of 0.114 to 0.171 kg / m3.
    [44]
    A process for effecting a process modification in an internal combustion engine comprising using as a fuel for the internal combustion engine the fuel composition of claim 25, characterized in that the fuel lubricity additive is present in an amount sufficient to reduce wear in an internal combustion engine operating using the fuel composition, in comparison with wear in the engine operating in the same manner and using the same fuel except that the fuel has no fuel. the lubricity additive for fuels.
    [45]
    45. A process according to claim 44, characterized in that the fuel lubricity additive is present in the fuel composition in an amount of 0.07125 to 0.4275 kg / m3.
    [46]
    46. A process according to claim 44, characterized in that the fuel lubricity additive is present in the fuel composition in an amount of 0.114 to 0.171 kg / m3.
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    US20070193110A1|2007-08-23|
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    法律状态:
    2010-08-31| RE| Patent lapsed|Effective date: 20100228 |
    优先权:
    申请号 | 申请日 | 专利标题
    US35802406|2006-02-21|
    US11/358,024|US20070193110A1|2006-02-21|2006-02-21|Fuel lubricity additives|
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