Note: Descriptions are shown in the official language in which they were submitted.
CA 02400946 2002-08-20
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FUEL, ADDITIVE
This invention relates to novel fuel compositions which comprise novel
surfactant
compositions and to methods of preparation the fuels compositions and
surfactants.
International Patent Applicatioxi No WO 98/17745 describes a surfactant
composition
which comprises,
25% v/v of a diethanolamide,
SO% v/v of an ethoxylated alcohol, and
25% v/v of a fourteen carbon chain fatty acid with seven ethoxylate groups.
WO '745 especially describes fuel compositions comprising, ihte~ alia, an
additive
made up of a fatty acid diethanolamide, an .alcohol ethoxylate and an
ethoxylate of a
fatty acid, the degree of ethoxyiation being selected so that a Iong term
stable fuel
composition is formed.
Specifically, WO '745 teaches the use of lauric acid and lauric
diethanolamide.
Co-pending International Patent Application No WO 99/20715 to Pure Energy
Corporation describes similar surfactant compositions in which the fatty acid
used
has a hydrocarbon chain length of from C~ to Cis.
Furthermore, US Patent No 6,017,369 describes a diesel fuel composition
comprising, ihtef° alia, diesel, ethanol and a fatty acid having a
carbon chain length of
from C9 to Cis.
Whilst such additives provide significant reductions in emissions and may be
useable
at low concentrations, they suffer from the disadvantage that, for example,
lauric acid
has a relatively high melting point of between 44 and 46°C. Thus, at
room
temperature, lauric acid is waxy and difficult to formulate.
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CA 02400946 2002-08-20
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We have now surprisingly found a novel surfactant fuel additive which
overcomes or
mitigates the problems of known prior art composition.
Thus according to the invention we provide a fuel additive composition
comprising
an alkanolamide, an alkoxylated alcohol and an alkoxylated CI8-C22 fatty acid
or a
derivative thereof in which the degree of alkoxylation of the fatty acid is
from 0.5 to
5 mots of alkoxylate to l mol of oleic acid.
0 The alkanolamide is preferably an ethanolamide and more preferably a
diethanolamide. Especially preferred are the diethanolamides and particularly
the
super diethanolamides. By the term super diethanolamide we mean a
diethanolamide
in which. the nitrogen is substituted by an alkyl substituent e.g. alkyl CS to
CZO,
preferably C8 to C18, more preferably Cio to G18. The most preferred
diethanolamide
has a CI8 alkyl substituent i.e. oleic diethanolamide.
There are three commercial routes to alkanolamides;
Acid + alkanolamine = alkanolamide + water
Plant or animal oil (triglyceride) + alkanolamine = alkanolamide + glycerol
Methyl ester + alkanolamine = alkanolamide + methanol
These are listed in order of increasing product quality. The route via the
acid often
uses an excess of alkanolamine to produce a product higher in .amide than is
obtainable from the acid if a stoichiometric ratio is used; these products are
sometimes referred to as Kritchevsicy amides. The products derived from
reaction of
substantially stoichiometric proportions _ of an alkanolamide with a fatty
acid ester,
typically a methyl or glyceryl ester, are referred to as super~amides.
The alkoxylated alcohol is preferably an ethoxylated alcohol. It is essential
that the
ethoxylated alcohol is an oil soluble alcohol. Therefore, alkanols are
preferred and
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these may be primary, secondary or tertiary alkanols and especially primary
alkanols.
As the oil solubility of the alcohol may vary with the , carbon chain length
of the
ethoxylated alkanol, the alkanol is preferably a CS to C22 alkanol, more
preferably CS
to C15 alkanol. The ethoxylatad alcohol may comprise a mixture of alkanols.
However, it is preferred that in such mixhires one alkanol will predominate.
Thus,
the most preferred alkanol is predominantly a C9 to C11 alkanol. In addition
the
degree of ethoxylation of the alcohol may .be .varied and the oil solubility
will,
generally, decrease with the increase in the degree of ethoxylation. It is
preferred that
the ethoxylate to alcohol ratio is greater than 2. More preferably, the
ethoxylate to
alcohol ratio is from between 1 and 10, preferably between 1 and 5, more
preferably
between , 1 and 3 and especially between 2 and 3. A commercially available
ethoxylated alcohol is especially preferred in which the ethoxylate to alcohol
ratio is
2.75. Such an alcohol ethoxylate is available~as NEOI~OL 91/2.5.
The fatty acid ethoxylate may comprise the free acid, an ester, a mixture of
esters or a
mixture of the acid and one or more esters. When a fatty acid ester ethoxylate
is
used, the ester is preferably an alkyl oleate, preferably a C1 to C1o alkyl
oleate, such
as ethyl oleate and especially methyl oleate. The fatty acid derivative is
preferentially
an ester which may comprise any conventionally known ester moiety, however,
preferably the ester is an alkyl ester. The alkyl group may be a primary,
secondary or
tertiary alkyl group. However, the preferred ester group is a straight chain
alkyl
group, the alkyl chain being from CI to Clo. The methyl ester is especially
preferred.
The fatty acid group may' be any known Cl8 to C2~ fatty acid but oleic acid
(C~8) is
preferred.
Alkyl ester fatty acid ethoxylate may be manufactured using conventional
methods
known peg se. However, current technology only permits ethoxylation of a fatty
acid
ester by the PEG/fatty acid route where, in a~ fatty acid of the general
formula
RCOORI, Rl is methyl.
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We have now found that such ethoxylated fatty acid esters may be manufactured
by
esterification of a fatty acid with a methoxy polyethylene glycol (PEG) or any
other
alcohol ethoxylate, for example, a C9 or C11 alcohol ethoxylate.
Such novel processes can produce ethoxylated fatty acid esters of the general
formula;
RCO[CHZCHZO]nORI T
wherein R is an alkyl C8 to Czo group;
RI is an alkyl, C1 to Clo; and
n is an integer from 1 to 10.
Alternatively, ethoxylated fatty acids of formula I may be manufactured by
esterification of RCOOH with Rl [OCHZCH2]"OH, wherein R, R1 and n have the
meanings defined above.
However, in addition, the alcohol ethoxylate might be, for example, an
alkylphenol
ethoxylate.
The degree of alkoxylation, e.g., ethoxylation, propyloxylation or a mixture
thereof,
is chosen to optimise performance in the blend with the other two selected
surfactants
and may be from 0.5 to 5 but more preferably from 0.5 to 2.5. Tt is especially
preferred that the alkoxylation comprises etlioxylation. A suitable product
within this
range would be, for example that deri ved from the addition ~ of 1 mol of
ethylene
oxide to 1 mol of oleic acid, or a derivative thereof.
The fatty acid ethoxylate, e.g. oleic acid ethoxylate, rnay be derived from a
variety of
feedstocks, readily available worldwide. However, in a preferred embodiment of
the
invention the fatty acid eth.oxylate may be produced by ethoxylation or
esterification
of acids derived from animal fats e.g. beef tallow or vegetable oils, such as
soya, etc.
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Thus the oleic acid precursor may be predominantly, e.g. from 65-70% v/v,
fatty
acid, e.g. oleic acid, but may also contain linoleic acid, e.g., 10-12% v/v,
and may
also include'small amounts of stearic, palmitic and/or myristic acids.
The ratio of the fatty acid alkoxylate, e.g. oleic acid allcoxylate to the
allcanolamide
may vary slightly, but is preferably l :lv/v.
The additive of the invention may be added to any known hydrocarbon fuel, e.g.
diesel, petrol or alcohol, such as ethanol, which may or may not contain
water. The
invention is seen to particularly good effect when added to fuels based on low
fraction oils.
The preferred additive of this invention is a non-ionic surfactant and
preferably a
blend of surfactants. It is a preferred feature of this invention that the
surfactants be
selected by their nature and concentration that the additive (as well as any
water or
other non-fuel liquid present) be solubilised within the fuel. For this
purpose it is
convenient to have regard to the hydrophilic-lipophilic balance (HLB) of the
surfactant, the value being calculated according to the expression.
HLB = rnol. wt of hydrophilic chain x 20
total mol. wt
The values will depend on the length of the hydrophilic chain, typically an
ethoxylate
chain. The length of the chain will increase the extent of solubilisation
because of a
greater ability to solubilise.
As with the compositions described in W098/17745, a blend of surfactants is
preferred, preferably by selecting one appropriate to the fuel.
The invention has the ability to unify the HLB requirements of any liquid fuel
which
in turn allows for one dose to be used in any fuel from CS carbon chains up.
The
benefit being the amount of treatment directly related to the co-solvency
ability.
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Preferably the ethoxylate of the oleic acid makes up about 25% by volume of
the
additive and further preferably the alcohol ethoxylate comprises 50% by volume
of
the additive.
An additive of the invention may be added to a hydrocarbon fuel, eg diesel,
petrol or
alcohol, such as ethanol which may or may not be contaminated with water.
Alternatively the hydrocarbon fuel may be a blend of a petroleum based fuel
such as
diesel or petrol, with an.alcohol such.as ethanol. The invention is seen to
particularly
good effect when added to synthetic fuels based on low fraction oils.
The hydrocarbon fuel may comprise any known hydrocarbon fuel or mixtures
thereof, therefore such fuels include but shall not be limited to diesel,
e.g., petroleum
diesel, gasoline, aviation fuel, alcohol, etc.
In one embodiment of the fuel composition of the invention the hydrocarbon
fuel is a
petroleum diesel fuel. Such fuels may generally be obtained from the
distillation of
petroleum and its efficiency can be measured by the cetane number. Suitable
diesel
fuels for use in accordance with the invention generally have a cetane number
of
from 35 to 60, preferably from 40 to 50. The amount of diesel fuel blended to
form
the fuel composition of the invention may be from 60 % v/v to 95 % v/v, based
on
the total volume of the fuel consumption.
In a further feature of the invention the hydrocarbon fael, such a diesel or
gasoline
may include an amount of an oxygenator, e.g. alcohol, an alkanol, such as
ethanol.
When an alcohol is present the amount of alcohol may vary depending, i~tey~
alia,
upon the nature of the fuel, but may in an amount of from 1 to 50% v/v,
preferably 5
to 20% v/v.
For fuels, ethanol may be produced from fossil fuel feedstoclcs or by
fermentation of
sugars derived from grains or other biomass materials. Therefore, ethanol
suitable
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for use in accordance with the fuel compositions of the invention may be fuel
grade
ethanol derived from yeast or bacterial fermentation of starch-based sugars.
Such
starch-based sugars may be extracted from corn, sugarcane, tapioca and sugar
beet.
Alternatively, fuel grade ethanol may be produced via known dilute andlor
concentrated acid and/or enzymatic hydrolysis of a particular biomass
material, for
example, from waste industrial sources including, cellulosic portions of
municipal
solid waste, waste paper, paper sludge, saw dust. Biomass may also be
collected
from agricultural residues including, for example, rice husks and paper-mill
sludge.
A suitable fuel grade ethanol .for use in accordance with the invention may
contain
none or only contaminant levels of water. Alternatively, a suitable fuel grade
ethanol
for use in accordance with the invention may contain higher amounts of water,
up to
5% w/w (hydrous ethanol).
Use of ethanol in combination with a diesel fuel has previously posed problems
wherein the ethanol/diesel fuel mixture would undesirably sepaxate into two
distinct
phases, especially when water is present, and render the resultant mixture
unsuitable
for use as a combustible fuel. The use of the fuel additives of the invention
permits
hydrous ethanol to be blended satisfactorily with conventional diesel fuel
without
forming two phases. The use of fuel grade ethanol blended in accordance with
the
invention imparts desirable combustion characteristics to the overall fuel
composition; such as improved fuel stability, lower smoke and particulate
matter,
lower CO and NOx emissions, improved antiknock characteristics, and/or
improved
anti-freeze characteristics.
In another aspect the invention provides a fuel composition comprising a light
weight
fraction and a surfactant fuel additive as hereinbefore described.
The presence of the additive of the invention ensures that the fuel
composition forms
a consistent ''stable homogenous composition and creates a monolayer
simultaneously
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a result of which leads to a better more complete burn which reduces pollution
and
increases miles per gallon.
As a result a blended fuel, particularly alcohol based, is able to combust
more
precisely with a cooler charge to reduce the iron-formates present from the
aldehyde
peracids and peroxide reactions normally attributable to engine degradation.
Thus we further provide a fuel composition comprising a fuel and a hydrocarbon
fuel
additive as herein before described.
The concentration of the additive in such fuel compositions can be very low,
typically
of the order of 0.5 - 50:1000 v/v, preferably from about 1:1000. to 30:1000
v/v and
most preferably from 1 to 3:100 v/v. There appears to be no technical or
economic
benefit in adding more unless a co-solvent dual action is reduired, when the
priority
will be dosage against performance. However, the additive to fuel ratio may
vary
depending upon, inter alia, the nature of the fuel. Thus, for example, when
the fuel
is a hydrous ethanol/diesel blend, the additive to fuel ratio may be as much
as 5%
v/v, e.g. from 0.1 to S% v/v, more preferably from 1 to 3% v/v. Alternatively,
when
the fuel is an anhydrous ethanol/diesel blend the additive to fuel ratio may
be as
much as 3% v/v, e.g. from 0.1 to 3% v/v. The amount of ethanol present in the
diesellethanol blends of the invention may be from S to 25% v/v, preferably
from 7 to
10% v/v and especially 7.7% v/v. When the athanol in the blend is hydrous
ethanol,
the amount of water present may be from ~l to 6°'°v/v based, as
a percentage of the
ethanol.
Alternatively, when the fuel is gasoline or a gasoline/ethariol blend, then
the additive
to fuel ratio may be as much as 5% v/v, from 0.1 to S% v/v, preferably up to
3% v/v,
e.g. 0.1 to 3% v/v, more preferably from 1 to 3% v/v. The amount of ethanol
present
in the gasoline/ethanol blends of the invention may be from 1 to 25% vlv,
preferably
S to 25% v/v, more preferably from 7 to 10% v/v and especially 7.7% v/v. When
the
fuel is a hydrous ethanol/gasoline blend, the additive to fuel ratio may be as
much as
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WO 01/62877 PCT/GBO1/00777
5% v/v. Alternatively, when the fuel is an anhydrous ethanol/gasoline blend
the
additive to fuel ratio may be as much as 3% v/v.
The presence .of the additive of the invention ensures that the fuel
composition forms
a consistent stable homogenous composition and creates a mon~layer
simultaneously
a.result of which leads to a better more complete. burn which reduces
pollution and
increases miles, per gallon.
As a result a blended fuel, particularly alcohol based, is able to combust
more
precisely with a cooler charge to reduce the iron-formates present from the
aldehyde
peracids and peroxide reactions normally attributable to engine degradation.
We also provide a method of running an engine adapted to use a hydrocarbon or
an
alcohol based fuel which comprises the use of a fuel composition as
hereinbefore
described.
The use of a fuel additive composition comprising an. oleic acid ethoxylate or
a
derivative thereof is especially advantageous in conjunction with diesel fuel
compositions and especially diesel/alcohol compositions. Thus, according to a
further feature of the invention we provide a fuel composition comprising a
diesel
fuel, an alcohol and a surfactant additive as hereinbefore described.
The alcohol is preferably ethanol. Optionally, the diesel composition of the
invention
may additionally include the use of an alkyl ester of oleic acid e.g. an alkyl
C1 to 6
alcohol or a long chain. fatty alcohol and, optionally a co-solvent of an
alkyl alcohol,
e.g. a C3 to C6 alcohol.
According to a further feature of the invention we provide the use of oleic
acid or a
derivative thereof in the manufacture of a surfactant additive as hereinbefore
described.
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According to a yet further feature of the invention we provide the use of
oleic acid or
a derivative thereof in the manufacture of a fuel composition as hereinbefore
described.
The invention will now be described by way of example only.
Example 1
Emission Tests
Emission tests were carried. out on a fuel composition containing the 95%
diesel 5%
ethanol blend and AAE01.
AAE01 is a surfactant composition comprising 25% v/v of oleic diethanolamide,
50% v/v of NEODOL 91/2.5, and 25%. v/v of oleic acid with one molar equivalent
ethoxylate groups.
1.1 Test engine
General features of the test engine are given in Table 1.
Table 1. Gea~e~al features of the test eyzgine.
Malce, model VOLVO DlEIIQA-285
Number of cylinders and 6, in-line
lay-out
Displacement 9.6 dm'
Injection pump electrically controlled mechanical
in-line pump
Maximum power output 210kW at 2000 1/min
Maximum torque 1200 Nm at 1450 llmin
Compression ratio 20:1 .
Combustion system direct injection, turbocharged,
intercooled
Emission level Euro II
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1.2 Test equipment and procedures
All equipment used for measuring the, regulated emissions (Co, Hc, Nox and
particulates) conform with the specifications for measurement system given in
Annex
4 of ECE Regulation No 49/02.
A hydraulic dynamometer by Zollner and a "PUMA Test Assistant" control system
by AVL were used for running and controlling the test engine. Regulated
gaseous
emissions were measured with analysis system by BOO Instrument AB.
Particulates
were collected using AVL Mini Dilution Tunnel 474. Particulate filters used
were
Pallflex TXH120WW QJ 70 mm filters.
Test procedure was 13 mode test according to ECE Regulation No. 49/02. The
maximum power output obtained with each fuel was used to set dynamometer load
setting.
The tests were carried out at normal test temperature.
FTIR measurement, formaldehyde from heavy-duty en ine
In the heavy-duty engine tests, a number of unregulated compounds, including
formaldehyde, were measured using a Fourier Transformation Infra-Red (FTIR)
system (SESAM II Fast, manufactured by Siemens AG, FRG). More than 20 exhaust
components can be measaured with this system, at a one second time interval.
1.3 Test results
The maximum power obtained with Dl fuel wasa 210 kW at 2000 rpm and
~0 maximum torque 1200 Nm at 1450 rpm. Power loss with fuel D2 was below 1%
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when compared to D1 fuel. Power losses with fuels D3 and D4 when compared to
D 1 fuel were 5 and 7% respectively.
Results of the emission tests according to the ECE R49 13-mode test for heavy-
duty
tests axe given in Table 2. One test with each fuel was carried. out.
Increase in HC emission was observed for fuels D3 and~D4 when compared to fuel
Dl.
NOX emission seemed to be slightly lower with fuels D2, D3 and D4 than with
fuel
Dl. However, the change lower than 5% cannot be regarded as very significant
due
to uncertainty of the measurement method.
Particulate matter emission was about 11 % lower witih D2 fuel than with D 1
fuel.
D3 fuel resulted 20% and D4 fuel 27% lower particulate emission than D1 fuel.
Also
black smoke (Bosch smoke) seemed to° be lower with fuels D2, D3 and D4
when
compared to D 1 fuel.
Table 2. Results of the emissions tests according to ECE R49 test procedure
with the VOLVO DHIOA-2~5 engine
Fuel CO HC NOx ParticulatesCOZ Fuel Bosch
~ cons.
(g/kWh)(g/kWh)(g/kWh)(g/kWh) (g/lcWh)(g/lcWh)smolce*
D1 (Base) 0.51 0.15 6.3 0.105 688 230 0.50
D2 (Base 0.51 0.15 6.2 0.093 693 231 0.48
+
2% AAE01)
D3 (Base 0:51 0.20 6.1 0.084 696 233 0.41
+
2% AAE01
+
2% H20)
D4 (Base 0.51 0.20 6.0 0.076 698 235 0.40
+
1 % AAE01
+
5% MTBE)
* average value without weighting factors
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The reults of FTIR measurements are shown in Table 3. The most components
measured from the exhaust gases of Volvo DH10A-285 engine were below the
detection limit of FTIR equipment. Formaldehyde emission seemed to be slightly
higher with D3 fuel than with D2 fuel. The difference resulted from the high
load
modes 6 and 8. The emission of n-octane was higher with D3 fuel than with D2
fuel,
which is in accordance with the results of regulated emissions shown in Table
2.
Table 3. Results of the FTIR measurmenets from ECE R49 test with the
IrOLVO DHlOA.-285 engine.
Fuel N20 NHz CH20' CH4 BNZ NC8
(mg/kWh)(mg/kWh)(mg/kWh) (mglkWh)(mg/Kwh)(mg/kWh)
D2 bd bd 24 , bd bd 97
D3 bd bd 35 BD BD 120
bd = below detection limited
Example 2
Light-duty emission tests
2.1 Pest vehicle
The general features of the petrol fuelled vehicle that was used in the
emission tests
are shown in Table 4.
Table 4. Genet~al featm°es of the test vehicle
2S
Make, model Ford Mondeo 1.6 BFP/270
Model year 1998 '
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Odometer reading 29 100 km
Transmission manual, 5
Number of cylinders and 4
Iay-out
Displacaement 1.6dm
Maximum power output 66 kW
The absolute emission level obtained with FTIR equipment may vary
significantly
from the level obtained with traditional measurement technologies. ~ However,
FTIR
technology can be used for comparison of 'the results with different fuels.
Due to
very Iow Ievel hydrocarbon emissions from diesel engines, the most compounds
that
can be measured with FTIR equipment are beloe the detection limit. When diesel
engines are considered, FTIR is most suitable to monitor the formaldehyde
emission.
Examples of the compounds that were recorded during these measurements were as
l.0 follows:
formaldehyde
(CHZO)
nitrogen diaxide
(NOz)
nitrous oxide
(N20)
ammonium (NH3)
methane (CI-I4)
ethyne (C~H~)
ethene (C2H40
propene (C,H6)
benzene (ENZ)
~0 n-octane (NC8)
1,3-butadiene
(C4H6)
Test equipment and brocedures
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All equipment usd for exhaust dilution and collection, as well as
concentration
analysis of the gaseous regulated emissions, conform with the specificatioins
of the
Amendment 91/441/EEC of Directive 70/220/EEC.
A DC type chassis dynamometer manufactured by Froude Consine and an emission
measaurement system by Pierburg GmbH (FRG) were used.
Tests were conducted at normal test temperature (+23°C). The
vehicle was
preconditi.on.ed with running three times the FUDC part of the test, and
soaked at the
test temperature for 12 to 16 hours before the test.
The chassis dynamaometer settings used for vehicle are presented in Table 5.
Table S. Chassis dynamometer settings
Inertia 1360 kg
Fo 7
Fi 0
Fz 0.06
The gaseous regulated emissions were divided into three sub-cycles. The first
part
included the first two individual sub-cycles of urban cycle, ECE15 (marked as
Phase
1), the second phase was the ,rest of the ECE1 S cycle. (marked as Phase 2),
and the
third pa~.-t was the extra urban portion (marled as Phase 3) of the current
European
test cycle (marked as 91/441/EEC).
The results of the test were compared by Sekab with results obtained from
similar
tests carried out by a AB Svensk Biprovning Motocenter (Swedish Engine and MOT
test centre) on several fuel compositions including Swedish Mkl diesel,
generally
regarded as the cleanest diesel available in Europe.
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The comparisons shown on the Bi07/EthanoZlDiesel Emission Test Results are
evidence to a dramatic reduction in all measured emissions including, -20%
CO2, -
30%NOX and -70% particulates.
Five months after the original tests VTT took the sample of fuel they had been
keeping and ran a cetane test on it, the result of which is enclosed. As noted
in this
test the sample had remained clear and stable for this period and no
deterioration was
evident.
Results
AAE01/Ethanol/Diesel Blends
Emission Test Results
CO HC Nox C02 Particulates
g/kWh glkWh g/kWh g/kWh g/kWh
Mkl 0.61 0.47 6.95 1085 0.2'
Mk2 0.61 0.5 7.14 1053 0.21
RME 0.49 0.09 8.99 1053 0.21
Mlcl +5%RME 0.62 0.44 7.16 1054 0.2
Mlc2 +30%RME 0.58 0.33 7.8 1068 0.19
AAE01 Diesohol 0.55 0.21, 4.9 863.6 0.056
AAE01 diesohol compared with Mkl diesel
CO HC Nox C02 Particulates
glkWh g/kWh g/kWh g/kWh g/kWh
Mkl Diesel 0.61 0.47 6.95 1085 0.2
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AAEOI Diesohol 0.55 0.21 4.9 863.6 0.056
Reductions ~ 10% S5% . 29% 20% 72%
Fuel Specifications
Mkl - Scandinavian environmental class 1 diesel fuel
Mk2 - Scandinavian environmental class 2 diesel fuel
RME - Rapeseed Methyl Ester
AAE01 - 4.25-94.5% Mkl diesel + 5% Ethanol (90% grade) + 0.5-0.75% AAE01 (all
by volume)
All testing carried out on a Volvo Euro II low emission engine.
20
30
17
