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Functionalized Maleated Fatty Acids as Non Acidic Fluid Additives

Inactive Publication Date: 2012-03-01
BAKER HUGHES INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0007]There is provided, in one non-limiting form, a method of improving the lubricity of a hydrocarbon fuel that involves adding to the hydrocarbon fuel an effective amount of functionalized maleated fatty acid that is an ester, imide and / or amide to improve the lubricity thereof. The functionalized maleated fatty acid is made by a process including reacting an unsaturated fatty acid with an unsaturated compound selected from the group consisting of an unsaturated anhydride, a maleimide, and mixtures thereof. The unsaturated compound may be substituted with a linear or branched alkyl group. This first step gives a maleated fatty acid. Subsequently, the maleated fatty acid is reacted with a multifunctional reactant selected from the group consisting of a polyol, an alkanolamine, an alkylene oxide and mixtures thereof. This gives a functionalized maleated fatty acid that has an acid number less than 10. The functionalized maleated fatty acid may optionally have one of the structures (I) through (IX) shown below.
[0008]In addition to, or alternative to the above-noted method for improving the lubricity of a hydrocarbon fuel, it is expected that the functionalized maleated fatty acid may also improve the lubricity of a lubricant, e.g. a motor oil; a transmission fluid, e.g. in an automotive automatic transmission, and in an alcohol, e.g. in methanol and / or ethanol when used as a fuel. Further, it is expected that the functionalized maleated fatty acid may also reduce the corrosivity of these fluids with respect to metals that they come into contact with, as well as to reduce the corrosivity of hydrocarbon fuels.

Problems solved by technology

The problem is general to diesel fuels, kerosene and gasolines, however, most of the studies have concentrated on the first two hydrocarbon fuels.
Unfortunately, many commercially available fatty acids and fatty acid blends tend to freeze or form crystals at lower temperatures common during winter weather.
The freezing or formation of crystals makes handling of the additives, and particularly their injection into fuel, difficult.
However, addition of a solvent may increase cost and preparation complexity.
Some of the fatty acids, fatty acid ammonium salts and fatty acid amides presently used may have the disadvantage of solidifying on storage at low temperatures.
Often even at room temperature, crystalline fractions may separate and cause handling problems.
Diluting the additives with organic solvents only partly solves the problem, since fractions may still crystallize out from solutions or the solution may gel and solidify.

Method used

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  • Functionalized Maleated Fatty Acids as Non Acidic Fluid Additives
  • Functionalized Maleated Fatty Acids as Non Acidic Fluid Additives
  • Functionalized Maleated Fatty Acids as Non Acidic Fluid Additives

Examples

Experimental program
Comparison scheme
Effect test

examples 1-5

Preparation of Functionalized Maleated Fatty Acid Products

example 1

[0029]The preparation of maleated fatty acid: In a typical reaction, oleic acid (100 g) and maleic anhydride (25 g) were charged into a 250 ml 3-neck flask under nitrogen. The mixture was heated sequentially up to 240° C. for 30 hrs until the reaction was completed. The reaction was monitored by FT-infrared spectroscopy (FT-IR) as is known to those skilled in the art. The final product was diluted by aromatic solvent to a concentration of 90% active and marked as Example 1.

[0030]Above is a representative structure of Example 1 material.

example 2

[0031]Oleic acid (100.1 g) and maleic anhydride (25.3 g) were mixed in a 3-neck flask. The mixture was heated sequentially up to 240° C. until the reaction is completed as monitored by FT-IR. The reaction mixture was first cooled to room temperature, and then ethanolamine (38.0 g) was added drop-wise while stirring. After the addition was completed, the reaction temperature was first set at 80° C., and then raised to 180° C. sequentially in 2 hours. The reaction process was monitored by FT-IR and acid number analysis. A second batch of ethanolamine (6.0 g) was added after 8 hrs reaction time. The reaction was stopped when the acid number is below 3. The final product was diluted with aromatic solvent to a concentration of 80% active and marked as Example 2.

[0032]Above is a representative structure of Example 2.

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Abstract

Maleated fatty acids that are functionalized with materials such as polyols, alkanolamines and / or alkylene oxides have been discovered to improve the properties of various fluids. In a non-limiting example, functionalized maleated fatty acids having acid numbers less than 10 may improve the lubricity of fuels and lubricants, such as hydrocarbon fuels and lubricants, when added thereto.

Description

TECHNICAL FIELD[0001]The present invention relates to methods and compositions for improving the properties of various fluids, and more particularly relates, in one non-limiting embodiment, to methods and compositions for hydrocarbon fuel lubricity additives made from maleic anhydride and fatty acids.TECHNICAL BACKGROUND[0002]It is well known that in many internal combustion engines the fuel is also the lubricant for the fuel system components, such as fuel pumps and injectors. Many studies of fuels with poor lubricity have been conducted in an effort to understand fuel compositions that have poor lubricity and to correlate lab test methods with actual field use. The problem is general to diesel fuels, kerosene and gasolines, however, most of the studies have concentrated on the first two hydrocarbon fuels.[0003]Previous work has shown that saturated, monomeric and dimeric, fatty acids of from 12 to 54 carbon atoms used individually give excellent performance as fuel lubricity aids ...

Claims

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Application Information

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IPC IPC(8): C10L1/19C10M129/70C10M133/16C10L1/224
CPCC10L1/1905C10N2240/10C10L1/224C10L10/04C10L10/08C10M129/72C10M133/16C10M2207/282C10M2207/283C10M2207/289C10M2215/08C10M2215/082C10M2215/086C10N2220/021C10N2230/06C10N2230/12C10N2240/04C10L1/191C10N2020/04C10N2030/06C10N2030/12C10N2040/04C10N2040/25
Inventor YANG, JIANZHONGBIGGERSTAFF, PAUL J.WEERS, JERRY J.
Owner BAKER HUGHES INC
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