Fuel and related compositions – Liquid fuels – Organic nitrogen compound containing
Reexamination Certificate
1999-11-24
2003-02-04
Toomer, Cephia D. (Department: 1714)
Fuel and related compositions
Liquid fuels
Organic nitrogen compound containing
C508S542000, C556S026000, C564S367000, C564S368000
Reexamination Certificate
active
06514297
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to improved detergents for use in hydrocarbon fuels. In particular, the present invention is directed to an improved detergent useful in the prevention of iron complexes in hydrocarbon fuel.
Hydrocarbon fuels generally contain numerous deposit-forming substances. When used in internal combustion engines, deposits tend to form on and around constricted areas of the engine in contact with the fuel. In diesel engines, deposits tend to accumulate in the fuel injection system, thereby hampering good performance of the engine. In automobile engines, deposits can build up on engine intake valves leading to progressive restriction of gaseous fuel mixture flow into the combustion chamber and also to valve sticking. It is common practice, therefore, to incorporate a detergent in the fuel composition for the purpose of inhibiting the formation, and facilitating the removal, of engine deposits, thereby improving engine performance. Certain Mannich condensation products, obtained by reacting hydrocarbon-substituted phenols, aldehydes and amines, are known as detergents for fuels. These have an advantage over polyisobutene amine detergents in that they are substantially chlorine free.
U.S. Pat. No. 4,117,011 discloses Mannich condensation products obtained by reacting hydrocarbon-substituted phenols, aldehydes, amines and alkylene oxides as dispersants/detergents for lubricating oils and hydrocarbon fuels. Preferred reactants include polyisobutene-substituted phenols, formaldehyde, and alkylene polyamines such as diethylene triamine which, in one process, are combined in a Mannich condensation reaction before being reacted with a polyalkylene oxide.
CA-A-2089833 and EP-A-647700 both disclose fuel compositions containing detergent additives which comprise Mannich reaction products of a polyisobutene-substituted phenol, an amine and an aldehyde, the amine preferably being an alkylene polyamine such as diethylene triamine, triethylene tetramine and the like. Although ethylene diamine is mentioned in EP-A-647700 as a possible amine, no compounds employing it are disclosed, and it is not amongst the preferred amines; nor is there any mention in either of these documents of the nature of the polyisobutene employed.
U.S. Pat. No. 5,876,468 is directed to the discovery that Mannich condensation products of particular polyisobutene-substituted phenols, an aldehyde and ethylene diamine are especially good detergents in fuels, and significantly better than those described in the above-mentioned prior art. The present invention is directed to an improvement in detergents suitable for use with hydrocarbon fuels, especially detergents of the type disclosed in the U.S. Pat. No. 5,876,468.
SUMMARY OF THE INVENTION
It is the primary object of the present invention to provide a novel detergent for use in hydrocarbon fuels.
It is another object of the present invention to provide a process for preventing the formation of iron complexes in hydrocarbon fuels utilizing the novel detergent.
It is a further object of the present invention to provide a process for the manufacture of the novel detergent of the present invention.
Additional objects and advantages of the present invention will be set forth in part in the description which follows and, in part, will be obvious from the description or may be learned by the practice of the invention. The objects and advantages of the invention may be realized and attained by means of the instrumentalities and combinations particularly pointed out in the appended claims.
To achieve the foregoing objects and in accordance with the purpose of the invention as embodied and broadly described herein, the improved detergent of the present invention comprises a composition comprising the reaction product of (1) the Mannich reaction product of a polyisobutene-substituted phenol, an aldehyde, and an amine; and (2) a compound selected from the group consisting of alkylbenzene sulfonic acids, alkylnapthalene sulfonic acids, acetylacetone and mixtures thereof.
In a preferred enbodiment of the present invention the alkyl group is selected form the range of C
6
to C
18
, more preferably C
8
to C
14
, and especially preferred being C
10
to C
4
.
In another preferred embodiment of the aspect of the present invention, the polyisobutene from which the substituted phenol is derived is selected to contain terminal olefinic double bonds of the vinylidene type, preferably greater than 50%, especially preferred being greater than 70%.
In a further preferred embodiment of this aspect of the present invention, the amine is selected to be an alkylene polyamine, preferably ethylene diamine, diethylene diamine, triethylene diamine, especially preferred being ethylene diamine.
In a still further preferred embodiment of this aspect of the present invention, the compound is added in the range of greater than 0 to 1000 ppm, preferably 20 to 100 ppm, especially preferred being 40 to 80 ppm
Another aspect of the present invention comprises a fuel composition comprising a major amount of hydrocarbon fuel including 10 to 1000 ppm of the above-described detergent mixture.
A still further aspect of the present invention comprises a method of preventing the formation of iron complexes in a fuel comprising a major amount of a hydrocarbon fuel and a Mannich reaction product of a polyisobutene-substituted phenol where the polyisobutene from which the polyisobutene substituted phenol is derived contains at least 50% terminal double bonds of the vinylidene type comprising adding about 3.0 to 20 ppb of the compound to said fuel, preferably about 3 to 16 ppb.
Reference will now be made in detail to the present preferred embodiment of the invention.
DETAILED DESCRIPTION OF THE INVENTION
The following description of the present invention will primarily be directed to the use of polyisobutene (PiBs) having at least 70% of the terminal olefinic double bonds which are of the vinylidene type. However, it should be understood that other PiBs having less than 70% vinylidene type terminal olefinic double bonds may be utilized in the composition of the present invention. For example, PiB's having 50% or less terminal olefinic double bonds which are of the vinylidene type may be suitable in the practice of the invention.
PiBs in which at least 70% of the terminal olefinic double bonds are of the vinylidene type are commonly known as “high reactive” polyisobutenes, as distinct from “low reactive” PiBs (having a lower proportion of vinylidene terminal double bonds which are commonly used. Examples of “high reactive” polyisobutenes include Ultravis® marketed by BP Chemicals and Glissopal® marketed by BASF. The composition of the invention is particularly useful when the Mannich reaction product is formed from the reaction of ethylene diamine, formaldehyde and a PiB substituted phenol in which the PiB is highly reactive. The combination of the Mannich reaction product with or without the alkylbenzenesulfonic acid and/or aklylnapthalenesulfonic acid and/or acetylacetone provide surprisingly superior performance to known fuel detergents based on Mannich chemistry. However, the presence of the alkylbenzenesulfonic acid and/or aklylnapthalenesulfonic acid and/or acetylacetone provide the additional advantage of preventing the formation of iron complexes where the detergent is brought into contact with mild steel containers. This additional advantage substantially eliminates the need for storing the detergent of the present invention in stainless steel or plastic containers, thereby enabling the material to be stored in conventional steel-based containers.
Preferably, the PiB has a number average molecular weight of from 700 to 2300, particularly from 750 to 1500, especially preferred being from 900 to 1300. The aldehyde is preferably a (C
1
-C
6
) aldehyde, most preferably formaldehyde.
As mentioned above, the composition of the invention is made by admixing one component comprising a Mannich reaction product and a second component selected from the group consisting of
McAtee Rodney J.
Moreton David John
Esposito Michael F.
Laferty Samuel B.
Munson Jeffrey F.
The Lubrizol Corporation
Toomer Cephia D.
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