Fuel compositions

Details Fuel compositions Fuel compositions

1997-10-09

2001-11-06

Medley, Margaret (Department: 1714)

Fuel and related compositions

Liquid fuels

Organic nitrogen compound containing

C044S443000, C554S064000, C544S168000, C564S201000, C564S203000, C564S204000

Reexamination Certificate

active

06312481

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to the use of monoamide-containing polyether alcohol compounds as additives in fuel compositions and the use of these compounds to decrease intake valve deposits, control octane requirement increase, and reduce octane requirement. The present invention further relates to a class of monoamide-containing polyether alcohol compounds.
2. Background
The octane requirement increase effect exhibited by internal combustion engines, e.g., spark ignition engines, is well known in the art. This effect may be described as the tendency for an initially new or relatively clean engine to require higher octane quality fuel as operating time accumulates, and is coincidental with the formation of deposits in the region of the combustion chamber of the engine.
During the initial operation of a new or clean engine, a gradual increase in octane requirement, i.e., fuel octane number required for knock-free operation, is observed with an increasing build up of combustion chamber deposits until a stable or equilibrium octane requirement level is reached. This level appears to correspond to a point in time when the quantity of deposit accumulation on the combustion chamber and valve surfaces no longer increases but remains relatively constant. This so-called “equilibrium value” is normally reached between 3,000 and 20,000 miles or corresponding hours of operation. The actual equilibrium value of this increase can vary with engine design and even with individual engines of the same design; however, in almost all cases, the increase appears to be significant, with octane requirement increase values ranging from about 2 to about 10 research octane numbers being commonly observed in modern engines.
The accumulation of deposits on the intake valves of internal combustion engines also presents problems. The accumulation of such deposits is characterized by overall poor driveability including hard starting, stalls, and stumbles during acceleration and rough engine idle.
Many additives are known which can be added to hydrocarbon fuels to prevent or reduce deposit formation, or remove or modify formed deposits, in the combustion chamber and on adjacent surfaces such as intake valves, ports, and spark plugs, which in turn causes a decrease in octane requirement.
Continued improvements in the design of internal combustion engines, e.g., fuel injection and carburetor engines, bring changes to the environment of such engines thereby creating a continuing need for new additives to control the problem of inlet system deposits and to improve driveability which can be related to deposits.
It would be an advantage to have fuel compositions which would reduce the formation of deposits and modify existing deposits that are related to octane requirement increase and poor driveability in modern engines which burn hydrocarbon fuels.
SUMMARY OF THE INVENTION
The present invention is directed to the use of monoamide-containing polyether alcohol compounds as additives in fuel compositions comprising a major amount of a mixture of hydrocarbons in the gasoline boiling range and a minor amount of one or more monoamide-containing polyether alcohol compounds of the formula:
wherein R
1
, R
2
and R
3
are each independently selected from the group consisting of hydrogen, hydrocarbyl of 1 to 100 carbon atoms, substituted hydrocarbyl of 1 to 100 carbon atoms and polyoxyalkylene alcohol of 2 to 200 carbon atoms or R
2
and R
3
taken together form a heterocyclic group of 2 to 100 carbon atoms or a substituted heterocyclic group of 2 to 100 carbon atoms and the weight average molecular weight of the additive compound is greater than about 600 with the proviso that at least one of R
1
, R
2
or R
3
must be polyoxyalkylene alcohol.
The invention is also directed to the use of these monoamide-containing polyether alcohol compounds for decreasing intake valve deposits, controlling octane requirement increases and reducing octane requirement. The present invention is further directed to a class of monoamide-containing polyether alcohol compounds.
DESCRIPTION OF THE PREFERRED EMBODIMENTS COMPOUNDS
The compounds of the present invention, broadly expressed as monoamide-containing alkoxylates, are a new class of additives useful for hydrocarbon fuels, e.g., fuels in the gasoline boiling range, for preventing deposits in engines, controlling octane requirement increases and reducing octane requirement, while also decomposing during combustion to environmentally acceptable products. The compounds produce very little residue and are miscible with carriers and other detergents. Non-limiting illustrative embodiments of the compounds useful as additives in the instant invention include those of Formula I:
In Formula I, R
1
, R
2
and R
3
are each independently selected from the group consisting of hydrogen, hydrocarbyl of 1 to 100 carbon atoms, substituted hydrocarbyl of 1 to 100 carbon atoms and polyoxyalkylene alcohol of 2 to 200 carbon atoms or R
2
and R
3
taken together form a heterocyclic group of 2 to 100 carbon atoms or a substituted heterocyclic group of 2 to 100 carbon atoms with the proviso that at least one of R
1
, R
2
and R
3
must be polyoxyalkylene alcohol. When one or more of R
1
, R
2
or R
3
are polyoxyalkylene alcohol, they are preferably independently selected from polyoxyalkylene alcohol of Formula II:
wherein x is from 1 to 50 and each R
4
is independently selected from the group consisting of hydrocarbyl of 2 to 100 carbon atoms and substituted hydrocarbyl of 2 to 100 carbon atoms.
As used herein, the term “hydrocarbyl” represents a radical formed by the removal of one or more hydrogen atoms from a carbon atom of a hydrocarbon (not necessarily the same carbon atom). Useful hydrocarbyls are aliphatic, aromatic, substituted, unsubstituted, acyclic or cyclic. Preferably, the hydrocarbyls are aryl, alkyl, alkenyl or cycloalkyl and are straight-chain or branched-chain. Representative hydrocarbyls include methyl, ethyl, butyl, pentyl, methylpentyl, hexenyl, ethylhexyl, dimethylhexyl, octamethylene, octenylene, cyclooctylene, methylcyclooctylene, dimethylcyclooctyl, isooctyl, dodecyl, hexadecenyl, octyl, eicosyl, hexacosyl, triacontyl and phenylethyl. As noted, the hydrocarbyls utilized may be substituted. As used herein the term “substituted hydrocarbyl” refers to any “hydrocarbyls” which contain a functional group such as carbonyl, carboxyl, nitro, amino, hydroxy (e.g. hydroxyethyl), oxy, cyano, sulfonyl, and sulfoxyl. The majority of the atoms, other than hydrogen, in substituted hydrocarbyls are carbon, with the heteroatoms (i.e., oxygen, nitrogen, sulfur) representing only a minority, 33% or less, of the total non-hydrogen atoms present.
When either R
1
, R
2
or R
3
are hydrocarbyl or substituted hydrocarbyl they will preferably be hydrocarbyl or substituted hydrocarbyl of 1 to 50 carbon atoms, more preferably hydrocarbyl or substituted hydrocarbyl of 1 to 20 carbon atoms. Particularily preferred embodiments of the present invention are those in which when either R
1
, R
2
or R
3
are hydrocarbyl, they are independently selected from alkyl of 1 to 20 carbon atoms and cycloalkyl of 4 to 20 carbon atoms, preferably alkyl of 1 to 10 carbon atoms and cycloalkyl of 4 to 10 carbon atoms. When either R
1
, R
2
or R
3
are hydrocarbyl of a relatively high number of carbon atoms, i.e., greater than about 50 carbon atoms, each will be represented by polymeric hydrocarbyls derived from polyisobutylene, polybutene, polypropylene or polyalpha olefin.
In addition, R
2
and R
3
taken together with the nitrogen atom to which they are connected can form a heterocyclic group of 4 to 100 carbon atoms or a substituted heterocyclic group which contains 4 to 100 carbon atoms. Preferably R
2
and R
3
taken together form a heterocyclic group which contains 4 to 50 carbon atoms and even more preferably of 4 to 20 carbon atoms.
As used herein, the term “heterocyclic group” refers to any cyclic group comprising both a nitrogen atom and carbon atoms which ma

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