Note: Descriptions are shown in the official language in which they were submitted.
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FUEL ADDITIVE AND FUEL COMPOSITION CONTAINING THE SAME
The present invention relates to a fuel additive containing an alkylene-oxide-
adducted hydrocarbyl amide. In a further aspect the present invention relates
to
the use of the fuel additive in a hydrocarbon-based fuel, such as gasoline
fuel or
diesel fuel, to enhance the acceleration response and the driving performance
of
internal combustion engines, such as gasoline or diesel engines.
BACKGROUND OF THE INVENTION
In order to increase engine output power and acceleration response of spark
ignition engines in automobiles, various types of oxygen-containing additives
for
hydrocarbon-based fuel have been investigated. These hydrocarbon-based
fuels include alcohol (e.g. methanol and ethanol), ether (e.g. methyl-t-butyl
ether), and ketone (e.g. acetone). In addition, the use of additives, such as
hydrazine or nitro compounds (for example nitromethane including nitropropane
and nitroparaffin, or nitrobenzene) have been examined for automobile racing.
However, the problem with using such additives is that they often have an
adverse effect on the durability of the engine and its components.
It is also known that organometallic compounds (e.g. tetraethyl lead or
similar
lead alkyls:ferrocene, methyl cyclopentadienyl manganese tricarbonyl ), as
well
as aromatic amine compounds (e.g. aniline, monomethyl aniline, or dimethyl
aniline) can be used as anti-knocking agents. However, it has been confirmed
that these compounds dramatically reduce the operating efficiency of three-way
catalysts due to catalyst poisoning.
Japanese Patent Application Number (Kokai) 58-104996 (con-esponding to US
Patent Number 4,409,000) describes the use of an alkyl amine or ethylene-
oxide-adducted alkenyl amine as an additive in automobile fuel to clean
carburetors and engines.
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According to European Patent Number 0869163 A1 it is possible to reduce
friction in gasoline engines by adding N,N-bis(hydroxyalkyl) alkyl amine to
gasoline.
According to PCT Patent Publication 2001-502374 (WO-98/17746), solubility in
water as well as the engine performance can be improved by adding fatty acid
diethanol amide, fatfi; acid ethoxylate and alcohol ethoxylate to a liquid
fuel such
as gasoline or diesel fuel.
SUMMARY OF THE INVENTION
The present invention relates to a fuel additive containing an alkylene-oxide-
adducted hydrocarbyl amide. In a further aspect the present invention relates
to
the use of the fuel additive in a hydrocarbon-based fuel, such as gasoline
fuel or
diesel fuel, to enhance the acceleration response and the driving performance
of
internal combustion engines, such as gasoline or diesel engines.
In its broadest aspect, the present invention relates to a fuel additive
comprising
an alkylene-oxide-adducted hydrocarbyl amide having from 3 to 50 moles of
alkylene oxide per mole of hydrocarbyl amide.
In another aspect, the present invention relates to a fuel composition
comprising
a major amount of a hydrocarbon boiling in the gasoline or diesel range and,
from 10 to 10,000 ppm weight per weight of fuel, of the fuel additive of the
Present invention.
In still another aspect, the present invention relates to a method of
operating an
automobile engine with the fuel composition of the present invention.
In a further aspect, the present invention relates to a method of improving
the
acceleration performance of a gasoline automobile engine comprising additizing
the fuel additive of the present invention to a gasoline and operating the
engine
with the additized gasoline.
Among other factors, the present invention is based on the discovery that
certain
alkylene-oxide-adducted hydrocarbyl amides are surprisingly useful for
improving
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CA 02390822 2002-06-17
the acceleration response and the driving performance of internal comp ustion
engines when used as fuel additives in hydrocarbon-based fuels, such as
gasoline fuel or diesel fuel.
DETAILED DESCRIPTION OF THE INVENTION
As stated above, the present invention relates to a fuel additive containing
an
alkylene-oxide-adducted hydrocarbyl amide and its use as a fuel additive in a
hydrocarbon-based fuel, such as gasoline fuel or diesel fuel.
Prior to discussing the present invention in detail, the following terms will
have
the following meanings unless expressly stated to the contrary.
Definitions
The term "hydrocarbyl" refers to an organic radical primarily composed of
carbon
and hydrogen which may be aliphatic, alicyclic, aromatic or combinations
thereof,
e.g., aralkyl or alkaryl. Such hydrocarbyl groups may also contain aliphatic
unsaturation, i.e., ole>'inic or acetylenic unsaturation, and may contain
minor
amounts of heteroatoms, such as oxygen or nitrogen, or halogens, such as
chlorine. When used in conjunction with carboxylic fatty acids, hydrocarbyl
will
also include olefinic unsaturation.
The term °alkyl" refers to both straight- and branched-chain alkyl
groups.
The term "lower alkyl" refers to alkyl groups having 1 to about 6 carbon atoms
and includes primary, secondary and tertiary alkyl groups. Typical lower alkyl
groups include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-
butyl,
t-butyl, n-pentyl, n-hexyl and the like.
The term ualkenyl" refers to an alkyl group with unsaturation.
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The term °alkylene oxide" refers to a compound having the formula:
O
R~ C H CH R2
wherein R~ and R2 are eacE r independently hydrogen or lower alkyl having from
1
to 6 carbon atoms.
The term "fuel" or "hydrocarbon-based fuel" refers to normally liquid
hydrocarbons having boiling points in the range of gasoline and diesel fuels.
In its broadest aspect, the present invention involves a fuel additive
comprising
an alkylene-oxide-adducted hydrocarbyl amide having from 3 to 50 moles,
preferably from 3 to 20 moles, more preferably from 4 to 15 moles, of alkylene
oxide per mole of hydrocarbyl amide.
The alkylene-oxide-adducted hydrocarbyl amide of the present invention is
derived from an alkyl amide having from 4 to 75, preferably from 8 to 22,
carbon
atoms or alkenyl amide with at least one or two points of unsaturation having
from 4 to 75, preferably from 8 to 22, carbon atoms. Examples of desirable
alkyl
amides suitable for the present invention include, but are not limited to,
octyl
amide (capryl amide), nonyl amide, decyl amide (caprin amide), undecyl amide
dodecyl amide (lauryl amide), tridecyl amide, teradecyl amide (myristyl
amide),
pentadecyl amide, hexadecyl amide (palmityl amide), heptadecyl amide,
octadecyl amide (stearyl amide), nonadecyl amide, eicosyl amide (alkyl amide),
or docosyl amide (behenyl amide). Examples of desirable alkenyl amides
include, but are not limited to, palmitoolein amide, oleyl amide, isooleyl
amide,,
elaidyl amide, linolyl amide, linoleyl amide. Preferably, the alkyl or alkenyl
amide
is a coconut oil fatty acid amide.
The alkylene oxide adducted to the hydrocarbyl amide of the present invention
is
derived from an alkylene group having from 2 to 5 carbon atoms. Preferably,
the
alkylene oxide is selected from the group consisting of ethylene oxide,
propylene
oxide, butylene oxide, and pentylene oxide. Ethylene oxide and propylene oxide
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CA 02390822 2002-06-17
are particularly preferred. In addition, mixtures of alkylene oxides are
desirable
in which, for example, a mixture of ethylene oxide and propylene oxide may be
used to form the alkylene-oxide-adducted hydrocarbyl amide of the present
invention. A respective molar ratio of from 1:5 to 5:1 may be used in the case
of
a mixture of ethylene oxide and propylene oxide.
A desirable number of moles of the alkylene oxide to be adducted to the
hydrocarbyl amide will be in the range of from 3 to 50 moles of alkylene oxide
per 1 mole of hydrocarbyl amide. More preferably, the range of from 3 to 20
moles is particularly desirable. Most preferably, the range of from 4 to 15
moles
is most preferable as a molar range of the additive.
Preferably, the alkylene-oxide adducted hydrocarbon amide is derived from an
alkylene-oxide-adduction reaction involving a coconut oil fatty acid amide
with
ethylene oxide and propylene oxide. However, the alkylene-oxide adducted
hydrocarbyl amides useful as fuel additives in the present invention can be
also
a mixed product wherein various types and different moles of alkylene oxide
and
can be adducted to various types of hydrocarbyl amides.
The present invention provides for a method of operating gasoline engine
automobiles wherein an automobile equipped with a gasoline engine is operated
with the fuel composition of the present invention. The method of operating
gasoline engine automobiles is preferred when the amount of alkylene oxide is
from 3 to 20 moles per mole of hydrocarbyl amide and the alkylene oxide is
selected from the group consisting of ethylene oxide, propylene oxide,
butylene
oxide, pentylene oxide, or mixtures thereof.
The present invention further provides for a method of improving the driving
and
acceleration performance of internal combustion engines, such as a gasoline or
diesel engines in automobiles, by using the fuel additive described herein.
The fuel additive of the present invention improves acceleration performance
of
internal combustion engines when the fuel additive is added to a low boiling
point
hydrocarbon-based fuel like gasoline, and the driving performance is also
improved when the additive is added to other hydrocarbon-based fuel like a
diesel fuel, alcohol fuel or ether fuel. The method of improving acceleration
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CA 02390822 2002-06-17
performance in gasoline engine automobiles is preferred when the amount of
alkylene oxide is from 3 to 20 moles per mole of hydrocarbyl amide and the
alkylene oxide is selected from the group consisting of ethylene oxide,
propylene
oxide, butylene oxide, pentylene oxide, or mixtures thereof.
The amount of fuel additive of the present invention added in a hydrocarbon-
based fuel will typically be in a range of from 10 to 10,000 ppm weight per
weight
(active component ratio). More preferably, the desired range is from 10 to
5,000
ppm weight per weight, while a range of from 10 to 1,000 ppm weight per weight
is most preferable.
The fuel additive of the present invention is normally supplied as an organic
solvent solution with an effective fuel additive content of at least 30 weight
%,
based on the amount of the fuel additive and organic solvent solution.
Although no particular limitations are imposed on the method used to add a
fuel
additive of the present invention to a hydrocarbon-based fuel, a concentrated
fuel additive product may be prepared which contained at least 30 weight % of
the active component. This product can be added according to any selected
method including adding it into the fuel tank of a fuel station or into the
fuel tank
of a passenger car.
The fuel additive of the present invention can also be combined with one, two,
or
more other additives publicly known to be used in hydrocarbon-based fuels.
Such additives include, but are not limited to, deposit control additives such
as
detergents or dispersants, corrosion inhibitors, oxidation inhibitors, metal
deactivators, corrosion inhibitors, demulsifiers, static electricity
preventing
agents, anti-coagulation agents, anti-knock agents, oxygenates, flow
improvers,
pour point depressants, cetane improvers and auxiliary-solution agents.
EXAMPLES
The invention will be further illustrated by the following examples, which set
forth
particularly advantageous method embodiments. While the examples are
Provided to illustrate the present invention, they are not intended to limit
it. The
present invention has been described with reference to specific embodiments
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CA 02390822 2002-06-17
and it is intended to cover those various changes and substitutions than nay
be
made by those skilled in the art without departing from the spirit and scope
of the
appended claims.
Example 1
A Toyota Camry 1800cc, 5MT (Type E-SV40, provided with Knock Sensor, type
4S-FE engine), mounted on a chassis dynamometer, was operated at a constant
speed of 20 km/hr. The acceleration measurement was initiated by fully opening
the throttle and measuring the amount of time required for the vehicle speed
to
reach 110 kmlhr with the transmission locked in fourth gear. This measurement
was repeated 10 times using the same fuel and the median value obtained from
these 10 measurements was determined as the acceleration time period. In
addition, in order to minimize the influence of ambient conditions
(temperature,
pressure, etc.) on engine performance, the entire test procedure was executed
within a single day.
The gasoline used have the following specifications: density (at 15°C):
0.7389
g/cm3, Reid vapor pressure: 60.5 Kpa, octane number: 90.2 (RON), 82.3 (MON),
aromatics (volume %): 29.9, olefin (volume %): 15.6, 10% distillation
temperature
(°C): 50.0, 50% distillation temperature (°C): 92.0, 90%
distillation temperature
(°C): 169.5. The fuel composition was adjusted by adding 100mg/L of 5
moles of
oleyl amide-ethylene oxide (fuel additive) to this gasoline.
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Gasoline containing the above described fuel additive and gasoline without the
fuel additive (same as the above) were then tested in accordance with the test
procedures described herein above. Table 1 shows the results.
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Table 1
Test Fuel Oil Acceleration Time Period (20 -110km/hours)
Gasoline with No Additive24.91 seconds
(Comparative Example)
Fuel Composition 24.69 seconds
containing Additive
From the different acceleration time periods shown in Table 1, it is clear
that the
acceleration performance was improved by the fuel additive of the present
invention. Although the difference in the acceleration time period indicated
in
Table 1 is not dramatic (less than 1 %) with the fuel additive of the present
invention, this is a distinct difference, particularly in case of cars needing
to attain
a high speed, such as racing cars, etc. Furthermore, in addition to the
importance of acceleration for racing cars, even a small improvement in
acceleration performance can be very important for passenger cars driving on
public roads where it may be necessary to suddenly accelerate in order to
avoid
an accident, etc., as a result of a sudden event.
Example 2
The test was carried out as described in Example 1, using four moles of
propylene oxide adducted coconut oil fatty acid di-ethanol amide (fuel
additive)
was added at a concentration of 100 mg/L to this gasoline in order to prepare
a
fuel composition containing the fuel additive.
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Gasoline containing the above described fuel additive and gasoline witty;, ~t
the
fuel additive (same as the above) were then tested in the acceleration
evaluation
test in accordance with the test procedures described in Example 1. Table 2
shows the results of the test.
Table 2
Test Fuel Oil Acceleration Time Period (20 -110km/hours)
Gasoline with No Additive24.51 seconds
(Comparative Example)
Fuel Composition 24.38 seconds
containing Additive
As shown by the results in Table 2, the acceleration performance was clearly
improved when the fuel additive of the present invention was employed in the
fuel.
Example 3
The test was carried out as described in Example 1, using ten moles of
propylene oxide adducted coconut oil fatty acid di-ethanol amide (fuel
additive)
was added to provide a concentration of 100 mg/L in this gasoline in order to
prepare a fuel composition containing the fuel additive.
Gasoline containing the above described fuel additive and gasoline without
fuel
additive (same as the above) were then tested in accordance with the test
procedures described previously. Table 3 shows the results of the test.
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Table 3
Test Fuel Oil Acceleration Time Period (20 -110kmlhours)
Gasoline with No Additive24.85 seconds
(Comparative Example)
Fuel Composition 24.74 seconds
containing Additive
As shown by the results in Table 3, the acceleration performance was clearly
improved when the fuel additive of the present invention was employed in the
fuel.
Example 4
The test was carried out as described in Example 1 except the gasoline used
had the following specifications: density 9 at 15°C: 0.7303 g/cm3, Reid
vapor
pressure: 60.2Kpa, octane number: 92.1 (RON), aromatics (volume %): 23.19,
olefin (volume %) 19, 10% distillation temperature (°C): 54.3, 50%
distillation
temperature (°C): 86.2, 90% distillation temperature (°C): 158.1
and using four
moles of propylene oxide and two moles of ethylene oxide adducted coconut oil
fatty acid di-ett~anol amide (fuel additive) were added to provide a
concentration
of 100 mglL in this gasoline.
Gasoline containing the above described fuel additive and gasoline without
fuel
additive (same as the above) were then tested in accordance with the test
pi.,o~ures described previously. Table 4 shows the results of the test.
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Table 4.
Test Fuel Oil Acceleration Time Period (20 -110km/hours)
Gasoline with No Additive23.96 seconds
(Comparative Example)
Fuel Composition 23.75 seconds
containing Additive
As shown by the results in Table 4, the acceleration performance was clearly
improved when the fuel additive of the present invention was employed in the
fuel.
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