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Aminobenzoic Acid Derivatives

a technology of benzoic acid and derivatives, applied in the direction of additives, lubricant compositions, liquid carbonaceous fuels, etc., can solve the problems of incomplete combustion of fuel in devices, less effective use of lubricants, and less effective use of engine oil, so as to boost the tbn

Inactive Publication Date: 2013-10-24
THE LUBRIZOL CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The invention is about adding a specific chemical called an additive to lubricating compositions. This additive can increase the TBN (total base number) of the composition. This can be done by adding the additive to the composition along with another detergent, or by using the additive on its own. The added TBN can improve the performance of the lubricating composition in applications where high TBN is needed.

Problems solved by technology

It is known that lubricants become less effective during their use due to exposure to the operating conditions of the device they are used in, and particularly due to exposure to by-products generated by the operation of the device.
For example, engine oil becomes less effective during its use, in part due to exposure of the oil to acidic and pro-oxidant byproducts.
These byproducts result from the incomplete combustion of fuel in devices such as internal combustion engines, which utilize the oil.
These byproducts lead to deleterious effects in the engine oil, and so, on the engine as well.
These oxidized and acidic hydrocarbons can then go on to cause corrosion, wear and deposit problems.
Basic amine additives are an alternative to ash containing over-based metal detergents, in particular alkyl and aromatic amines However, the addition of basic amine additives can lead to additional detrimental effects.
However, such amines are believed to cause dehydrofluorination in fluoroelastomeric seals materials, such as Viton seals.
Seal degradation leads to seal failure, such as seal leaks, which harms engine performance and also can cause engine damage.
Generally, the base content, or total base number (TBN), of a lubricant can only be boosted modestly by such a basic amine before seals degradation becomes a significant issue, limiting the amount of TBN that can be provided by such additives.

Method used

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  • Aminobenzoic Acid Derivatives
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Examples

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specific embodiment

[0059]The invention will be further illustrated by the following examples, which sets forth particularly advantageous embodiments. While the examples are provided to illustrate the invention, they are not intended to limit it.

example 1-a

[0060]Synthesis of 4-(dimethylamino)benzoic acid decyl ester. A one-liter, four-necked, round-bottom flask, equipped with an overhead stirrer, sub-surface gas inlet tube, thermowell, Dean-Stark trap, and Friedrick's condenser, is charged with 316.3 grams (2.00 moles) of 1-decanol and 30 grams of solid Amberlyst-15 catalyst. The flask is purged with nitrogen and warmed to 120 degrees C. before 165 grams (1.00 mole) of 4-(dimethylamino)benzoic acid is added portion-wise over 10 minutes. Evolved water is condensed in the Dean-Stark trap. The mixture is stirred at 150 degrees C. for 6 hours and filtered hot using 50 grams of Fax-5 to remove any particulates. The filtrate is reheated to 150 degrees C. for 1 hr under vacuum (<40mmHg) to remove excess alcohol. The mixture is cooled to yield the desired product, in the form of a brown liquid.

example 1-b

[0061]Synthesis of 4-(dimethylamino)benzoic acid decyl ester. A one-liter, four-necked, round-bottom flask, equipped with an overhead stirrer, sub-surface gas inlet tube, thermowell, and Friedrick's condenser, is charged with 200.0 grams (1.26 moles) of 1-decanol and 3.34 grams (24.3 mmoles) of solid potassium carbonate. The flask is purged with nitrogen and warmed to 120 degrees C. before 179 grams (1.00 mole) of 4-(dimethylamino)benzoic acid methyl ester is added portion-wise over 10 minutes. The mixture is stirred at 150 degrees C. for 6 hours and filtered hot using 50 grams of Fax-5 to remove any particulates. The filtrate is reheated to 150 degrees C. for 1 hr under vacuum (<40mmHg) to remove excess alcohol. The mixture is cooled to yield the desired product, in the form of a brown liquid.

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Abstract

This invention relates to N-alkylated anthranilic acid derivative and their use in lubricants, such as engine oils, as TBN boosters. The invention particularly relates to compositions that deliver an ash-free base to a lubricant in the form of a basic amine additive, without adversely impacting seal compatibility and / or degradation, and methods thereof.

Description

FIELD OF THE INVENTION[0001]The invention relates to aminobenzoic acid derivatives, such N-alkylated anthranilic acid derivatives and similar materials, and their use in lubricants, such as engine oils. The invention particularly relates to delivering a basic amine to a lubricant while reducing and / or limiting detrimental effects commonly associated with basic amine additive containing lubricants, such as poor seal compatibility.BACKGROUND OF THE INVENTION[0002]It is known that lubricants become less effective during their use due to exposure to the operating conditions of the device they are used in, and particularly due to exposure to by-products generated by the operation of the device. For example, engine oil becomes less effective during its use, in part due to exposure of the oil to acidic and pro-oxidant byproducts. These byproducts result from the incomplete combustion of fuel in devices such as internal combustion engines, which utilize the oil. These byproducts lead to del...

Claims

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Application Information

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IPC IPC(8): C10M133/12
CPCC10M133/12C10M133/14C10M133/24C10M135/12C10M135/14C10M2215/06C10M2215/16C10M2219/06C10M2219/062C10M2223/045C10N2030/36C10N2030/40C10N2030/43C10N2030/42C10N2030/45C10N2030/52C10N2040/25C10N2010/04
Inventor IVANCIC, DANIELLE N.MOSIER, PATRICK E.DELBRIDGE, EWAN E.FRIEND, CHRISTOPHER L.
Owner THE LUBRIZOL CORP
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